{
 "cells": [
  {
   "cell_type": "markdown",
   "id": "028c89f1",
   "metadata": {},
   "source": [
    "## ILThermoPy CookBook"
   ]
  },
  {
   "cell_type": "markdown",
   "id": "8ed61a27",
   "metadata": {},
   "source": [
    "ILThermo 2.0 is the biggest curated database, containing a wide varieties of experimental data on ionic liquids. This cookbook shows how this database can be accessed in automatic mode via the ILThermoPy package."
   ]
  },
  {
   "cell_type": "markdown",
   "id": "7f0c95a7",
   "metadata": {},
   "source": [
    "### Basic search"
   ]
  },
  {
   "cell_type": "markdown",
   "id": "76be0d30",
   "metadata": {},
   "source": [
    "Functionality of ILThermo 2.0 allows one to search experimental data on ionic liquids by the name/CAS RN/chemical formula of compounds, number of components, measured property, and parameters of the source article (for more details see the description of the `ilt.Search` function):"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 1,
   "id": "07feac03",
   "metadata": {},
   "outputs": [
    {
     "name": "stdout",
     "output_type": "stream",
     "text": [
      "Help on function Search in module ilthermopy.search:\n",
      "\n",
      "Search(compound: Optional[str] = None, n_compounds: Literal[None, 1, 2, 3] = None, prop: Optional[str] = None, prop_key: Optional[str] = None, year: Optional[int] = None, author: Optional[str] = None, keywords: Optional[str] = None) -> pandas.core.frame.DataFrame\n",
      "    Runs ILThermo search and returns results as a dataframe\n",
      "    \n",
      "    Arguments:\n",
      "        compound: chemical formula, CAS registry number, or name (part or full)\n",
      "        n_compounds: number of mixture compounds\n",
      "        prop: name of physico-chemical property, only used if prop_key is not specified\n",
      "        prop_key: key of physico-chemical property (view available via GetPropertyList)\n",
      "        year: publication year\n",
      "        author: author's last name\n",
      "        keywords: keywords presumably specified in paper's title\n",
      "    \n",
      "    Returns:\n",
      "        dataframe containing main info on found entries\n",
      "\n"
     ]
    }
   ],
   "source": [
    "import ilthermopy as ilt\n",
    "\n",
    "help(ilt.Search)"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 2,
   "id": "98a87aa8",
   "metadata": {},
   "outputs": [
    {
     "data": {
      "text/html": [
       "<div>\n",
       "<style scoped>\n",
       "    .dataframe tbody tr th:only-of-type {\n",
       "        vertical-align: middle;\n",
       "    }\n",
       "\n",
       "    .dataframe tbody tr th {\n",
       "        vertical-align: top;\n",
       "    }\n",
       "\n",
       "    .dataframe thead th {\n",
       "        text-align: right;\n",
       "    }\n",
       "</style>\n",
       "<table border=\"1\" class=\"dataframe\">\n",
       "  <thead>\n",
       "    <tr style=\"text-align: right;\">\n",
       "      <th></th>\n",
       "      <th>id</th>\n",
       "      <th>reference</th>\n",
       "      <th>property</th>\n",
       "      <th>phases</th>\n",
       "      <th>num_phases</th>\n",
       "      <th>num_components</th>\n",
       "      <th>num_data_points</th>\n",
       "      <th>cmp1</th>\n",
       "      <th>cmp1_id</th>\n",
       "      <th>cmp1_smiles</th>\n",
       "      <th>cmp2</th>\n",
       "      <th>cmp2_id</th>\n",
       "      <th>cmp2_smiles</th>\n",
       "      <th>cmp3</th>\n",
       "      <th>cmp3_id</th>\n",
       "      <th>cmp3_smiles</th>\n",
       "    </tr>\n",
       "  </thead>\n",
       "  <tbody>\n",
       "    <tr>\n",
       "      <th>0</th>\n",
       "      <td>vffQK</td>\n",
       "      <td>Kabo et al. (2004)</td>\n",
       "      <td>Heat capacity at constant pressure</td>\n",
       "      <td>Liquid</td>\n",
       "      <td>1</td>\n",
       "      <td>1</td>\n",
       "      <td>1528</td>\n",
       "      <td>1-butyl-3-methylimidazolium hexafluorophosphate</td>\n",
       "      <td>ABChJv</td>\n",
       "      <td>CCCC[n+]1ccn(C)c1.F[P-](F)(F)(F)(F)F</td>\n",
       "      <td>None</td>\n",
       "      <td>None</td>\n",
       "      <td>None</td>\n",
       "      <td>None</td>\n",
       "      <td>None</td>\n",
       "      <td>None</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>1</th>\n",
       "      <td>aNLkc</td>\n",
       "      <td>Kabo et al. (2004)</td>\n",
       "      <td>Heat capacity at vapor saturation pressure</td>\n",
       "      <td>Crystal;Gas</td>\n",
       "      <td>2</td>\n",
       "      <td>1</td>\n",
       "      <td>137</td>\n",
       "      <td>1-butyl-3-methylimidazolium hexafluorophosphate</td>\n",
       "      <td>ABChJv</td>\n",
       "      <td>CCCC[n+]1ccn(C)c1.F[P-](F)(F)(F)(F)F</td>\n",
       "      <td>None</td>\n",
       "      <td>None</td>\n",
       "      <td>None</td>\n",
       "      <td>None</td>\n",
       "      <td>None</td>\n",
       "      <td>None</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>2</th>\n",
       "      <td>bNHLG</td>\n",
       "      <td>Kabo et al. (2004)</td>\n",
       "      <td>Heat capacity at vapor saturation pressure</td>\n",
       "      <td>Glass;Gas</td>\n",
       "      <td>2</td>\n",
       "      <td>1</td>\n",
       "      <td>111</td>\n",
       "      <td>1-butyl-3-methylimidazolium hexafluorophosphate</td>\n",
       "      <td>ABChJv</td>\n",
       "      <td>CCCC[n+]1ccn(C)c1.F[P-](F)(F)(F)(F)F</td>\n",
       "      <td>None</td>\n",
       "      <td>None</td>\n",
       "      <td>None</td>\n",
       "      <td>None</td>\n",
       "      <td>None</td>\n",
       "      <td>None</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>3</th>\n",
       "      <td>HzjQF</td>\n",
       "      <td>Sun et al. (2004)</td>\n",
       "      <td>Heat capacity at constant pressure</td>\n",
       "      <td>Crystal</td>\n",
       "      <td>1</td>\n",
       "      <td>1</td>\n",
       "      <td>111</td>\n",
       "      <td>4,6-dimethyl-N-phenylpyrimidin-2-amine dodecan...</td>\n",
       "      <td>ABYrQW</td>\n",
       "      <td>CCCCCCCCCCCC(=O)[O-].Cc1cc(C)nc(Nc2ccccc2)[nH+]1</td>\n",
       "      <td>None</td>\n",
       "      <td>None</td>\n",
       "      <td>None</td>\n",
       "      <td>None</td>\n",
       "      <td>None</td>\n",
       "      <td>None</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>4</th>\n",
       "      <td>sBpKf</td>\n",
       "      <td>Kabo et al. (2004)</td>\n",
       "      <td>Heat capacity at vapor saturation pressure</td>\n",
       "      <td>Liquid;Gas</td>\n",
       "      <td>2</td>\n",
       "      <td>1</td>\n",
       "      <td>42</td>\n",
       "      <td>1-butyl-3-methylimidazolium hexafluorophosphate</td>\n",
       "      <td>ABChJv</td>\n",
       "      <td>CCCC[n+]1ccn(C)c1.F[P-](F)(F)(F)(F)F</td>\n",
       "      <td>None</td>\n",
       "      <td>None</td>\n",
       "      <td>None</td>\n",
       "      <td>None</td>\n",
       "      <td>None</td>\n",
       "      <td>None</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>...</th>\n",
       "      <td>...</td>\n",
       "      <td>...</td>\n",
       "      <td>...</td>\n",
       "      <td>...</td>\n",
       "      <td>...</td>\n",
       "      <td>...</td>\n",
       "      <td>...</td>\n",
       "      <td>...</td>\n",
       "      <td>...</td>\n",
       "      <td>...</td>\n",
       "      <td>...</td>\n",
       "      <td>...</td>\n",
       "      <td>...</td>\n",
       "      <td>...</td>\n",
       "      <td>...</td>\n",
       "      <td>...</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>272</th>\n",
       "      <td>CymfL</td>\n",
       "      <td>Zhao et al. (2004b)</td>\n",
       "      <td>Viscosity</td>\n",
       "      <td>Liquid</td>\n",
       "      <td>1</td>\n",
       "      <td>1</td>\n",
       "      <td>1</td>\n",
       "      <td>1-(4-cyanobutyl)-3-methylimidazolium tetrafluo...</td>\n",
       "      <td>AAwOgS</td>\n",
       "      <td>Cn1cc[n+](CCCCC#N)c1.F[B-](F)(F)F</td>\n",
       "      <td>None</td>\n",
       "      <td>None</td>\n",
       "      <td>None</td>\n",
       "      <td>None</td>\n",
       "      <td>None</td>\n",
       "      <td>None</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>273</th>\n",
       "      <td>onFYh</td>\n",
       "      <td>Zhao et al. (2004b)</td>\n",
       "      <td>Density</td>\n",
       "      <td>Liquid</td>\n",
       "      <td>1</td>\n",
       "      <td>1</td>\n",
       "      <td>1</td>\n",
       "      <td>1-butyl-3-methylimidazolium hexafluorophosphate</td>\n",
       "      <td>ABChJv</td>\n",
       "      <td>CCCC[n+]1ccn(C)c1.F[P-](F)(F)(F)(F)F</td>\n",
       "      <td>None</td>\n",
       "      <td>None</td>\n",
       "      <td>None</td>\n",
       "      <td>None</td>\n",
       "      <td>None</td>\n",
       "      <td>None</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>274</th>\n",
       "      <td>NaZFE</td>\n",
       "      <td>Zhao et al. (2004b)</td>\n",
       "      <td>Viscosity</td>\n",
       "      <td>Liquid</td>\n",
       "      <td>1</td>\n",
       "      <td>1</td>\n",
       "      <td>1</td>\n",
       "      <td>1-butyl-3-methylimidazolium hexafluorophosphate</td>\n",
       "      <td>ABChJv</td>\n",
       "      <td>CCCC[n+]1ccn(C)c1.F[P-](F)(F)(F)(F)F</td>\n",
       "      <td>None</td>\n",
       "      <td>None</td>\n",
       "      <td>None</td>\n",
       "      <td>None</td>\n",
       "      <td>None</td>\n",
       "      <td>None</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>275</th>\n",
       "      <td>YbIco</td>\n",
       "      <td>Zhao et al. (2004b)</td>\n",
       "      <td>Density</td>\n",
       "      <td>Liquid</td>\n",
       "      <td>1</td>\n",
       "      <td>1</td>\n",
       "      <td>1</td>\n",
       "      <td>1-butyl-3-methylimidazolium tetrafluoroborate</td>\n",
       "      <td>AArYBF</td>\n",
       "      <td>CCCC[n+]1ccn(C)c1.F[B-](F)(F)F</td>\n",
       "      <td>None</td>\n",
       "      <td>None</td>\n",
       "      <td>None</td>\n",
       "      <td>None</td>\n",
       "      <td>None</td>\n",
       "      <td>None</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>276</th>\n",
       "      <td>HwTsD</td>\n",
       "      <td>Zhao et al. (2004b)</td>\n",
       "      <td>Equilibrium temperature</td>\n",
       "      <td>Crystal;Liquid</td>\n",
       "      <td>2</td>\n",
       "      <td>1</td>\n",
       "      <td>1</td>\n",
       "      <td>3-(3-cyanopropyl)-1-methylimidazolium chloride</td>\n",
       "      <td>AAjkls</td>\n",
       "      <td>CCCC[n+]1cccc(C)c1.[Cl-]</td>\n",
       "      <td>None</td>\n",
       "      <td>None</td>\n",
       "      <td>None</td>\n",
       "      <td>None</td>\n",
       "      <td>None</td>\n",
       "      <td>None</td>\n",
       "    </tr>\n",
       "  </tbody>\n",
       "</table>\n",
       "<p>277 rows × 16 columns</p>\n",
       "</div>"
      ],
      "text/plain": [
       "        id            reference                                    property  \\\n",
       "0    vffQK   Kabo et al. (2004)          Heat capacity at constant pressure   \n",
       "1    aNLkc   Kabo et al. (2004)  Heat capacity at vapor saturation pressure   \n",
       "2    bNHLG   Kabo et al. (2004)  Heat capacity at vapor saturation pressure   \n",
       "3    HzjQF    Sun et al. (2004)          Heat capacity at constant pressure   \n",
       "4    sBpKf   Kabo et al. (2004)  Heat capacity at vapor saturation pressure   \n",
       "..     ...                  ...                                         ...   \n",
       "272  CymfL  Zhao et al. (2004b)                                   Viscosity   \n",
       "273  onFYh  Zhao et al. (2004b)                                     Density   \n",
       "274  NaZFE  Zhao et al. (2004b)                                   Viscosity   \n",
       "275  YbIco  Zhao et al. (2004b)                                     Density   \n",
       "276  HwTsD  Zhao et al. (2004b)                     Equilibrium temperature   \n",
       "\n",
       "             phases  num_phases  num_components  num_data_points  \\\n",
       "0            Liquid           1               1             1528   \n",
       "1       Crystal;Gas           2               1              137   \n",
       "2         Glass;Gas           2               1              111   \n",
       "3           Crystal           1               1              111   \n",
       "4        Liquid;Gas           2               1               42   \n",
       "..              ...         ...             ...              ...   \n",
       "272          Liquid           1               1                1   \n",
       "273          Liquid           1               1                1   \n",
       "274          Liquid           1               1                1   \n",
       "275          Liquid           1               1                1   \n",
       "276  Crystal;Liquid           2               1                1   \n",
       "\n",
       "                                                  cmp1 cmp1_id  \\\n",
       "0      1-butyl-3-methylimidazolium hexafluorophosphate  ABChJv   \n",
       "1      1-butyl-3-methylimidazolium hexafluorophosphate  ABChJv   \n",
       "2      1-butyl-3-methylimidazolium hexafluorophosphate  ABChJv   \n",
       "3    4,6-dimethyl-N-phenylpyrimidin-2-amine dodecan...  ABYrQW   \n",
       "4      1-butyl-3-methylimidazolium hexafluorophosphate  ABChJv   \n",
       "..                                                 ...     ...   \n",
       "272  1-(4-cyanobutyl)-3-methylimidazolium tetrafluo...  AAwOgS   \n",
       "273    1-butyl-3-methylimidazolium hexafluorophosphate  ABChJv   \n",
       "274    1-butyl-3-methylimidazolium hexafluorophosphate  ABChJv   \n",
       "275      1-butyl-3-methylimidazolium tetrafluoroborate  AArYBF   \n",
       "276     3-(3-cyanopropyl)-1-methylimidazolium chloride  AAjkls   \n",
       "\n",
       "                                          cmp1_smiles  cmp2 cmp2_id  \\\n",
       "0                CCCC[n+]1ccn(C)c1.F[P-](F)(F)(F)(F)F  None    None   \n",
       "1                CCCC[n+]1ccn(C)c1.F[P-](F)(F)(F)(F)F  None    None   \n",
       "2                CCCC[n+]1ccn(C)c1.F[P-](F)(F)(F)(F)F  None    None   \n",
       "3    CCCCCCCCCCCC(=O)[O-].Cc1cc(C)nc(Nc2ccccc2)[nH+]1  None    None   \n",
       "4                CCCC[n+]1ccn(C)c1.F[P-](F)(F)(F)(F)F  None    None   \n",
       "..                                                ...   ...     ...   \n",
       "272                 Cn1cc[n+](CCCCC#N)c1.F[B-](F)(F)F  None    None   \n",
       "273              CCCC[n+]1ccn(C)c1.F[P-](F)(F)(F)(F)F  None    None   \n",
       "274              CCCC[n+]1ccn(C)c1.F[P-](F)(F)(F)(F)F  None    None   \n",
       "275                    CCCC[n+]1ccn(C)c1.F[B-](F)(F)F  None    None   \n",
       "276                          CCCC[n+]1cccc(C)c1.[Cl-]  None    None   \n",
       "\n",
       "    cmp2_smiles  cmp3 cmp3_id cmp3_smiles  \n",
       "0          None  None    None        None  \n",
       "1          None  None    None        None  \n",
       "2          None  None    None        None  \n",
       "3          None  None    None        None  \n",
       "4          None  None    None        None  \n",
       "..          ...   ...     ...         ...  \n",
       "272        None  None    None        None  \n",
       "273        None  None    None        None  \n",
       "274        None  None    None        None  \n",
       "275        None  None    None        None  \n",
       "276        None  None    None        None  \n",
       "\n",
       "[277 rows x 16 columns]"
      ]
     },
     "execution_count": 2,
     "metadata": {},
     "output_type": "execute_result"
    }
   ],
   "source": [
    "# search individual compounds published in 2004\n",
    "df = ilt.Search(n_compounds = 1, year = 2004)\n",
    "df"
   ]
  },
  {
   "cell_type": "markdown",
   "id": "4ff9b20e",
   "metadata": {},
   "source": [
    "Output dataframe contains main information for each found entry, namely:\n",
    "\n",
    "- **id**: ILThermo entry ID, can be used to retrieve data via `ilt.GetEntry` function;\n",
    "\n",
    "- **reference**: short notation of the source paper;\n",
    "\n",
    "- **property**: measured property;\n",
    "\n",
    "- **phases**: semicolon-separated list of the system's phases;\n",
    "\n",
    "- **num_phases**, **num_components**, **num_data_points**: number of system's components and phases, and number of measured data points;\n",
    "- **cmp**, **cmp_id**, **cmp_smiles**: compound name, ILThermo compound ID, and SMILES (all enumerated for compounds #1 - #3)."
   ]
  },
  {
   "cell_type": "markdown",
   "id": "0906b42c",
   "metadata": {},
   "source": [
    "### Properties"
   ]
  },
  {
   "cell_type": "markdown",
   "id": "2c293b87",
   "metadata": {},
   "source": [
    "To search by property, one need either property name or ILThermo property ID. Since they are internal parameters of the ILThermo 2.0 web interface, they must be obtained via the `ilt.ShowPropertyList` function:"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 3,
   "id": "a45524a6",
   "metadata": {},
   "outputs": [
    {
     "name": "stdout",
     "output_type": "stream",
     "text": [
      "\n",
      "# Activity, fugacity, and osmotic properties\n",
      "BPpY: Activity\n",
      "VjHv: Osmotic coefficient\n",
      "\n",
      "# Composition at phase equilibrium\n",
      "dNip: Composition at phase equilibrium\n",
      "MbEq: Eutectic composition\n",
      "lIUh: Henry's Law constant\n",
      "eCTp: Ostwald coefficient\n",
      "neae: Tieline\n",
      "WbZo: Upper consolute composition\n",
      "\n",
      "# Critical properties\n",
      "BPNz: Critical pressure\n",
      "rDNz: Critical temperature\n",
      "qpSz: Lower consolute temperature\n",
      "MvMG: Upper consolute pressure\n",
      "bRXE: Upper consolute temperature\n",
      "\n",
      "# Excess, partial, and apparent energetic properties\n",
      "cpbY: Apparent enthalpy\n",
      "teHk: Apparent molar heat capacity\n",
      "rTYh: Enthalpy of dilution\n",
      "aeiA: Enthalpy of mixing of a binary solvent with component\n",
      "VTiT: Enthalpy of solution\n",
      "brzp: Excess enthalpy\n",
      "Sqxi: Partial molar enthalpy\n",
      "mFmK: Partial molar heat capacity\n",
      "\n",
      "# Heat capacity and derived properties\n",
      "tnYd: Enthalpy\n",
      "kthO: Enthalpy function {H(T)-H(0)}/T\n",
      "qdUt: Entropy\n",
      "IZSt: Heat capacity at constant pressure\n",
      "KvgF: Heat capacity at constant volume\n",
      "zJIE: Heat capacity at vapor saturation pressure\n",
      "\n",
      "# Phase transition properties\n",
      "CXUw: Enthalpy of transition or fusion\n",
      "iaOF: Enthalpy of vaporization or sublimation\n",
      "SwyC: Equilibrium pressure\n",
      "ghKa: Equilibrium temperature\n",
      "lnrs: Eutectic temperature\n",
      "LUaF: Monotectic temperature\n",
      "NmYB: Normal melting temperature\n",
      "\n",
      "# Refraction, surface tension, and speed of sound\n",
      "YQDr: Interfacial tension\n",
      "bNnk: Refractive index\n",
      "imdq: Relative permittivity\n",
      "NlQd: Speed of sound\n",
      "ETUw: Surface tension liquid-gas\n",
      "\n",
      "# Transport properties\n",
      "HooV: Binary diffusion coefficient\n",
      "Ylwl: Electrical conductivity\n",
      "jjnq: Self diffusion coefficient\n",
      "pAFI: Thermal conductivity\n",
      "KTcm: Thermal diffusivity\n",
      "vBeU: Tracer diffusion coefficient\n",
      "PusA: Viscosity\n",
      "\n",
      "# Vapor pressure, boiling temperature, and azeotropic T & P\n",
      "hkog: Normal boiling temperature\n",
      "HwfJ: Vapor or sublimation pressure\n",
      "\n",
      "# Volumetric properties\n",
      "WxCH: Adiabatic compressibility\n",
      "zNjL: Apparent molar volume\n",
      "JkYu: Density\n",
      "psRu: Excess volume\n",
      "hXfd: Isobaric coefficient of volume expansion\n",
      "Bvon: Isothermal compressibility\n",
      "LNxL: Partial molar volume\n",
      "\n",
      "\n"
     ]
    }
   ],
   "source": [
    "ilt.ShowPropertyList()"
   ]
  },
  {
   "cell_type": "markdown",
   "id": "861ea5ab",
   "metadata": {},
   "source": [
    "If your old code raises `ValueError` during the property search, this indicates that the property ID and/or property name have changed in ILThermo 2.0 after update(s). In this case, simply correct the value to the actual one."
   ]
  },
  {
   "cell_type": "markdown",
   "id": "429cf440-b051-4570-93b9-20f1d992b931",
   "metadata": {},
   "source": [
    "Another way around this issue is to use `ilt.PropertyList` object:"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 4,
   "id": "df2fb84d-93a5-4231-bea3-ffaca2c1d872",
   "metadata": {},
   "outputs": [
    {
     "name": "stdout",
     "output_type": "stream",
     "text": [
      "Help on PropertyList in module ilthermopy.data_structs object:\n",
      "\n",
      "class PropertyList(builtins.object)\n",
      " |  Contains info on available physico-chemical properties and their API keys\n",
      " |  \n",
      " |  Attributes:\n",
      " |      properties (dict): two-level organized dictionary, interconnecting property\n",
      " |          types, properties, and their API keys\n",
      " |      key2prop (dict): maps API keys to property names\n",
      " |      prop2key (dict): maps property names to their API keys\n",
      " |  \n",
      " |  Methods defined here:\n",
      " |  \n",
      " |  Show(self) -> None\n",
      " |      Prints list of properties available in ILThermo 2.0 database\n",
      " |      formatted as api_key: property_name\n",
      " |  \n",
      " |  __init__(self)\n",
      " |      Initialize self.  See help(type(self)) for accurate signature.\n",
      " |  \n",
      " |  ----------------------------------------------------------------------\n",
      " |  Data descriptors defined here:\n",
      " |  \n",
      " |  __dict__\n",
      " |      dictionary for instance variables (if defined)\n",
      " |  \n",
      " |  __weakref__\n",
      " |      list of weak references to the object (if defined)\n",
      "\n"
     ]
    }
   ],
   "source": [
    "plist = ilt.PropertyList()\n",
    "help(plist)"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 5,
   "id": "7e719c37-5cfa-4d0c-8644-fc1a59351d04",
   "metadata": {},
   "outputs": [
    {
     "name": "stdout",
     "output_type": "stream",
     "text": [
      "BPpY\n"
     ]
    }
   ],
   "source": [
    "prop_name = 'Activity'\n",
    "prop_key = plist.prop2key.get(prop_name, None)\n",
    "print(prop_key)"
   ]
  },
  {
   "cell_type": "markdown",
   "id": "b9756ec9-ec97-4292-8182-43000bf15672",
   "metadata": {},
   "source": [
    "However, in most cases you do not need this functionality since the `ilt.Search` function supports the `prop` argument."
   ]
  },
  {
   "cell_type": "markdown",
   "id": "2c1a3612",
   "metadata": {},
   "source": [
    "### Retrieving data"
   ]
  },
  {
   "cell_type": "markdown",
   "id": "8be8c167",
   "metadata": {},
   "source": [
    "To load data on the found entries use the `ilt.GetEntry` function, which takes entry ID as input:"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 6,
   "id": "2ee7cb2d",
   "metadata": {},
   "outputs": [
    {
     "data": {
      "text/plain": [
       "Entry(id='srPOo', ref=Reference(full='Rebelo, L. P. N.; Najdanovic-Visak, V.; Visak, Z. P.; Nunes da Ponte, M.; Szydlowski, J.; Cerdeirina, C. A.; Troncoso, J.; Romani, L.; Esperanca, J. M. S. S.; Guedes, H. J. R.; de Sousa, H. C. (2004) Green Chem. 6(8), 369-381.'), property='Excess volume', property_type='Volumetric properties', phases=['Liquid'], components=[Compound(id='AADYJk', name='water', smiles='O'), Compound(id='AArYBF', name='1-butyl-3-methylimidazolium tetrafluoroborate', smiles='CCCC[n+]1ccn(C)c1.F[B-](F)(F)F')], num_data_points=185)"
      ]
     },
     "execution_count": 6,
     "metadata": {},
     "output_type": "execute_result"
    }
   ],
   "source": [
    "# random search\n",
    "df = ilt.Search(n_compounds = 2, year = 2004)\n",
    "# downloading first 10 entries\n",
    "data = [ilt.GetEntry(idx) for idx in df.id.iloc[:10]]\n",
    "# get first entry\n",
    "entry = data[0]\n",
    "entry"
   ]
  },
  {
   "cell_type": "markdown",
   "id": "8162f47b",
   "metadata": {},
   "source": [
    "Entry object contains detailed information on the data entry, including:\n",
    "\n",
    "- **id**: data entry ID;\n",
    "- **ref**: reference to the source article;\n",
    "- **property**, **property_type**: measured property and its type;\n",
    "- **phases**: list of system's phases;\n",
    "- **components**: list of system's components;\n",
    "- **num_phases**, **num_components**, **num_data_points**: number of system's components and phases, and number of measured data points; \n",
    "- **expmeth**: experimental method used to obtain the physchemical data;\n",
    "- **solvent**: solvent used in the experiment;\n",
    "- **constraints**: list of experimental constraints;\n",
    "- **data**: dataframe containing measured data;\n",
    "- **header**: full column names to the **data**, containing info on the measured property, measurement units, component, and phase;\n",
    "- **footnotes**: notes to the **data**;\n",
    "- **response**: original response."
   ]
  },
  {
   "cell_type": "markdown",
   "id": "a9baf06f",
   "metadata": {},
   "source": [
    "Let's illustrate the main attributes. Reference contains reference itself and the article's title:"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 7,
   "id": "5be53c65",
   "metadata": {},
   "outputs": [
    {
     "data": {
      "text/plain": [
       "('Rebelo, L. P. N.; Najdanovic-Visak, V.; Visak, Z. P.; Nunes da Ponte, M.; Szydlowski, J.; Cerdeirina, C. A.; Troncoso, J.; Romani, L.; Esperanca, J. M. S. S.; Guedes, H. J. R.; de Sousa, H. C. (2004) Green Chem. 6(8), 369-381.',\n",
       " 'A detailed thermodynamic analysis of [C4mim][BF4] + water as a case study to model ionic liquid aqueous solutions')"
      ]
     },
     "execution_count": 7,
     "metadata": {},
     "output_type": "execute_result"
    }
   ],
   "source": [
    "entry.ref.full, entry.ref.title"
   ]
  },
  {
   "cell_type": "markdown",
   "id": "4ace6e5e",
   "metadata": {},
   "source": [
    "Each component is a Compound object and contains the following fields:\n",
    "\n",
    "- **id**: compound id;\n",
    "- **name**: compound name;\n",
    "- **formula**: chemical formula;\n",
    "- **smiles**: compound SMILES;\n",
    "- **smiles_error**: if compounds SMILES was not retrieved, this field describes the reason;\n",
    "- **sample**: dictionary containing info on compound's source, purity, etc.;\n",
    "- **mw**: molar weight of the compound, g/mol."
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 8,
   "id": "74f539ac",
   "metadata": {},
   "outputs": [
    {
     "data": {
      "text/plain": [
       "('AADYJk',\n",
       " 'water',\n",
       " 'H2 O',\n",
       " 'O',\n",
       " None,\n",
       " {'Source': 'commercial source',\n",
       "  'Purification': 'estimated by the compiler',\n",
       "  'Purity': '99.8 mass %(fractional distillation)'},\n",
       " 18.02)"
      ]
     },
     "execution_count": 8,
     "metadata": {},
     "output_type": "execute_result"
    }
   ],
   "source": [
    "cmp1 = entry.components[0]\n",
    "cmp1.id, cmp1.name, cmp1.formula, cmp1.smiles, cmp1.smiles_error, cmp1.sample, cmp1.mw"
   ]
  },
  {
   "cell_type": "markdown",
   "id": "e9d089a6",
   "metadata": {},
   "source": [
    "**data** field contains dataframe with measured physchemical data. Its columns has short names V1, V2, V3, etc. for all variables. If for some variable the measurement error was provided, the corresponding column will be `d` concatanated to the column name of the original value, e.g. `V1` and `dV1`:"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 9,
   "id": "3c8aac5f",
   "metadata": {},
   "outputs": [
    {
     "data": {
      "text/html": [
       "<div>\n",
       "<style scoped>\n",
       "    .dataframe tbody tr th:only-of-type {\n",
       "        vertical-align: middle;\n",
       "    }\n",
       "\n",
       "    .dataframe tbody tr th {\n",
       "        vertical-align: top;\n",
       "    }\n",
       "\n",
       "    .dataframe thead th {\n",
       "        text-align: right;\n",
       "    }\n",
       "</style>\n",
       "<table border=\"1\" class=\"dataframe\">\n",
       "  <thead>\n",
       "    <tr style=\"text-align: right;\">\n",
       "      <th></th>\n",
       "      <th>V1</th>\n",
       "      <th>V2</th>\n",
       "      <th>V3</th>\n",
       "      <th>V4</th>\n",
       "      <th>dV4</th>\n",
       "    </tr>\n",
       "  </thead>\n",
       "  <tbody>\n",
       "    <tr>\n",
       "      <th>0</th>\n",
       "      <td>100.0</td>\n",
       "      <td>0.0040</td>\n",
       "      <td>278.15</td>\n",
       "      <td>-3.600000e-08</td>\n",
       "      <td>1.000000e-08</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>1</th>\n",
       "      <td>100.0</td>\n",
       "      <td>0.0040</td>\n",
       "      <td>283.15</td>\n",
       "      <td>-3.350000e-08</td>\n",
       "      <td>1.000000e-08</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>2</th>\n",
       "      <td>100.0</td>\n",
       "      <td>0.0040</td>\n",
       "      <td>288.15</td>\n",
       "      <td>-3.070000e-08</td>\n",
       "      <td>1.000000e-08</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>3</th>\n",
       "      <td>100.0</td>\n",
       "      <td>0.0040</td>\n",
       "      <td>293.15</td>\n",
       "      <td>-2.830000e-08</td>\n",
       "      <td>1.000000e-08</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>4</th>\n",
       "      <td>100.0</td>\n",
       "      <td>0.0040</td>\n",
       "      <td>298.15</td>\n",
       "      <td>-2.580000e-08</td>\n",
       "      <td>1.000000e-08</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>...</th>\n",
       "      <td>...</td>\n",
       "      <td>...</td>\n",
       "      <td>...</td>\n",
       "      <td>...</td>\n",
       "      <td>...</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>180</th>\n",
       "      <td>60000.0</td>\n",
       "      <td>0.5905</td>\n",
       "      <td>298.15</td>\n",
       "      <td>4.620000e-07</td>\n",
       "      <td>1.100000e-08</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>181</th>\n",
       "      <td>60000.0</td>\n",
       "      <td>0.5905</td>\n",
       "      <td>303.15</td>\n",
       "      <td>4.550000e-07</td>\n",
       "      <td>1.100000e-08</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>182</th>\n",
       "      <td>60000.0</td>\n",
       "      <td>0.5905</td>\n",
       "      <td>313.15</td>\n",
       "      <td>4.510000e-07</td>\n",
       "      <td>1.100000e-08</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>183</th>\n",
       "      <td>60000.0</td>\n",
       "      <td>0.5905</td>\n",
       "      <td>323.15</td>\n",
       "      <td>5.420000e-07</td>\n",
       "      <td>1.200000e-08</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>184</th>\n",
       "      <td>60000.0</td>\n",
       "      <td>0.5905</td>\n",
       "      <td>333.15</td>\n",
       "      <td>5.830000e-07</td>\n",
       "      <td>1.200000e-08</td>\n",
       "    </tr>\n",
       "  </tbody>\n",
       "</table>\n",
       "<p>185 rows × 5 columns</p>\n",
       "</div>"
      ],
      "text/plain": [
       "          V1      V2      V3            V4           dV4\n",
       "0      100.0  0.0040  278.15 -3.600000e-08  1.000000e-08\n",
       "1      100.0  0.0040  283.15 -3.350000e-08  1.000000e-08\n",
       "2      100.0  0.0040  288.15 -3.070000e-08  1.000000e-08\n",
       "3      100.0  0.0040  293.15 -2.830000e-08  1.000000e-08\n",
       "4      100.0  0.0040  298.15 -2.580000e-08  1.000000e-08\n",
       "..       ...     ...     ...           ...           ...\n",
       "180  60000.0  0.5905  298.15  4.620000e-07  1.100000e-08\n",
       "181  60000.0  0.5905  303.15  4.550000e-07  1.100000e-08\n",
       "182  60000.0  0.5905  313.15  4.510000e-07  1.100000e-08\n",
       "183  60000.0  0.5905  323.15  5.420000e-07  1.200000e-08\n",
       "184  60000.0  0.5905  333.15  5.830000e-07  1.200000e-08\n",
       "\n",
       "[185 rows x 5 columns]"
      ]
     },
     "execution_count": 9,
     "metadata": {},
     "output_type": "execute_result"
    }
   ],
   "source": [
    "entry.data"
   ]
  },
  {
   "cell_type": "markdown",
   "id": "a6b8edd0",
   "metadata": {},
   "source": [
    "**header** field contains full names of the corresponding columns, including measured property, its measurement unit, and optionally compound and phase:"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 10,
   "id": "82ea9814",
   "metadata": {},
   "outputs": [
    {
     "data": {
      "text/plain": [
       "{'V1': 'Pressure, kPa',\n",
       " 'V2': 'Mole fraction of 1-butyl-3-methylimidazolium tetrafluoroborate => Liquid',\n",
       " 'V3': 'Temperature, K',\n",
       " 'V4': 'Excess volume, m<SUP>3</SUP>/mol => Liquid',\n",
       " 'dV4': 'Error of excess volume, m<SUP>3</SUP>/mol => Liquid'}"
      ]
     },
     "execution_count": 10,
     "metadata": {},
     "output_type": "execute_result"
    }
   ],
   "source": [
    "entry.header"
   ]
  },
  {
   "cell_type": "markdown",
   "id": "903dde67",
   "metadata": {},
   "source": [
    "Combining data entries formatted in this way is possible, albeit difficult. However, that is a problem of a particular database, and such a task is beyound the scope of this API."
   ]
  },
  {
   "cell_type": "markdown",
   "id": "7debecad",
   "metadata": {},
   "source": [
    "### Substructure search"
   ]
  },
  {
   "cell_type": "markdown",
   "id": "86843285",
   "metadata": {},
   "source": [
    "#### Update status"
   ]
  },
  {
   "cell_type": "markdown",
   "id": "5cd3aa75",
   "metadata": {},
   "source": [
    "Structural information of the ILThermo compounds is a crucial part of `ilthermopy`. This information is stored in a table format, linking together ILThermo compound ID, compound name, and verified SMILES string. `ilthermopy` usually uses compound IDs to retrieve SMILES, however each update of the ILThermo 2.0 database changes all compound IDs. In this case `ilthermopy` still can retrieve SMILES using compound name, however, that is not a full-proof way and some SMILES can be missing.\n",
    "\n",
    "Therefore, it is a good idea to check if `ilthermopy` is up-to-date before you start exploring ILThermo database:"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 11,
   "id": "90eeeedb",
   "metadata": {},
   "outputs": [
    {
     "name": "stdout",
     "output_type": "stream",
     "text": [
      "ILThermo 2.0 database was last updated on June 04, 2024\n",
      "ilthermopy package was last updated on May 03, 2025\n",
      "\n",
      "ilthermopy package is up-to-date\n"
     ]
    }
   ],
   "source": [
    "ilt.CheckLastUpdate()"
   ]
  },
  {
   "cell_type": "markdown",
   "id": "df0c632b",
   "metadata": {},
   "source": [
    "#### Substructure search"
   ]
  },
  {
   "cell_type": "markdown",
   "id": "a0afe696",
   "metadata": {},
   "source": [
    "The easiest way to search by substructure is to filter all available compounds, and than filter the search output by compound IDs or compound names (if ilthermopy is not up-to-date). Imagine that we want to get all entries containing guanidinium cation. In this case we start with loading preliminary info on all abailable ILThermo entries:"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 12,
   "id": "7192e320",
   "metadata": {},
   "outputs": [
    {
     "data": {
      "text/html": [
       "<div>\n",
       "<style scoped>\n",
       "    .dataframe tbody tr th:only-of-type {\n",
       "        vertical-align: middle;\n",
       "    }\n",
       "\n",
       "    .dataframe tbody tr th {\n",
       "        vertical-align: top;\n",
       "    }\n",
       "\n",
       "    .dataframe thead th {\n",
       "        text-align: right;\n",
       "    }\n",
       "</style>\n",
       "<table border=\"1\" class=\"dataframe\">\n",
       "  <thead>\n",
       "    <tr style=\"text-align: right;\">\n",
       "      <th></th>\n",
       "      <th>id</th>\n",
       "      <th>reference</th>\n",
       "      <th>property</th>\n",
       "      <th>phases</th>\n",
       "      <th>num_phases</th>\n",
       "      <th>num_components</th>\n",
       "      <th>num_data_points</th>\n",
       "      <th>cmp1</th>\n",
       "      <th>cmp1_id</th>\n",
       "      <th>cmp1_smiles</th>\n",
       "      <th>cmp2</th>\n",
       "      <th>cmp2_id</th>\n",
       "      <th>cmp2_smiles</th>\n",
       "      <th>cmp3</th>\n",
       "      <th>cmp3_id</th>\n",
       "      <th>cmp3_smiles</th>\n",
       "    </tr>\n",
       "  </thead>\n",
       "  <tbody>\n",
       "    <tr>\n",
       "      <th>0</th>\n",
       "      <td>vffQK</td>\n",
       "      <td>Kabo et al. (2004)</td>\n",
       "      <td>Heat capacity at constant pressure</td>\n",
       "      <td>Liquid</td>\n",
       "      <td>1</td>\n",
       "      <td>1</td>\n",
       "      <td>1528</td>\n",
       "      <td>1-butyl-3-methylimidazolium hexafluorophosphate</td>\n",
       "      <td>ABChJv</td>\n",
       "      <td>CCCC[n+]1ccn(C)c1.F[P-](F)(F)(F)(F)F</td>\n",
       "      <td>None</td>\n",
       "      <td>None</td>\n",
       "      <td>None</td>\n",
       "      <td>None</td>\n",
       "      <td>None</td>\n",
       "      <td>None</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>1</th>\n",
       "      <td>cFdQS</td>\n",
       "      <td>Strechan et al. (2008a)</td>\n",
       "      <td>Heat capacity at vapor saturation pressure</td>\n",
       "      <td>Crystal 2;Gas</td>\n",
       "      <td>2</td>\n",
       "      <td>1</td>\n",
       "      <td>613</td>\n",
       "      <td>1-butyl-3-methylimidazolium trifluoroacetate</td>\n",
       "      <td>AAwaEi</td>\n",
       "      <td>CCCC[n+]1ccn(C)c1.O=C([O-])C(F)(F)F</td>\n",
       "      <td>None</td>\n",
       "      <td>None</td>\n",
       "      <td>None</td>\n",
       "      <td>None</td>\n",
       "      <td>None</td>\n",
       "      <td>None</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>2</th>\n",
       "      <td>eOKLZ</td>\n",
       "      <td>Safarov et al. (2021b)</td>\n",
       "      <td>Viscosity</td>\n",
       "      <td>Liquid</td>\n",
       "      <td>1</td>\n",
       "      <td>1</td>\n",
       "      <td>500</td>\n",
       "      <td>1-ethyl-3-methylimidazolium dicyanamide</td>\n",
       "      <td>AAiEIE</td>\n",
       "      <td>CC[n+]1ccn(C)c1.N#C[N-]C#N</td>\n",
       "      <td>None</td>\n",
       "      <td>None</td>\n",
       "      <td>None</td>\n",
       "      <td>None</td>\n",
       "      <td>None</td>\n",
       "      <td>None</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>3</th>\n",
       "      <td>UkHsx</td>\n",
       "      <td>Polikhronidi et al. (2014)</td>\n",
       "      <td>Heat capacity at constant pressure</td>\n",
       "      <td>Liquid</td>\n",
       "      <td>1</td>\n",
       "      <td>1</td>\n",
       "      <td>422</td>\n",
       "      <td>1-hexyl-3-methylimidazolium bis[(trifluorometh...</td>\n",
       "      <td>ABiCtA</td>\n",
       "      <td>CCCCCC[n+]1ccn(C)c1.O=S(=O)([N-]S(=O)(=O)C(F)(...</td>\n",
       "      <td>None</td>\n",
       "      <td>None</td>\n",
       "      <td>None</td>\n",
       "      <td>None</td>\n",
       "      <td>None</td>\n",
       "      <td>None</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>4</th>\n",
       "      <td>BvazU</td>\n",
       "      <td>Safarov et al. (2018c)</td>\n",
       "      <td>Viscosity</td>\n",
       "      <td>Liquid</td>\n",
       "      <td>1</td>\n",
       "      <td>1</td>\n",
       "      <td>394</td>\n",
       "      <td>1-octyl-3-methylimidazolium hexafluorophosphate</td>\n",
       "      <td>ABNWoR</td>\n",
       "      <td>CCCCCCCC[n+]1ccn(C)c1.F[P-](F)(F)(F)(F)F</td>\n",
       "      <td>None</td>\n",
       "      <td>None</td>\n",
       "      <td>None</td>\n",
       "      <td>None</td>\n",
       "      <td>None</td>\n",
       "      <td>None</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>...</th>\n",
       "      <td>...</td>\n",
       "      <td>...</td>\n",
       "      <td>...</td>\n",
       "      <td>...</td>\n",
       "      <td>...</td>\n",
       "      <td>...</td>\n",
       "      <td>...</td>\n",
       "      <td>...</td>\n",
       "      <td>...</td>\n",
       "      <td>...</td>\n",
       "      <td>...</td>\n",
       "      <td>...</td>\n",
       "      <td>...</td>\n",
       "      <td>...</td>\n",
       "      <td>...</td>\n",
       "      <td>...</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>54204</th>\n",
       "      <td>kxodn</td>\n",
       "      <td>Zhao et al. (2010a)</td>\n",
       "      <td>Composition at phase equilibrium</td>\n",
       "      <td>Liquid;Gas</td>\n",
       "      <td>2</td>\n",
       "      <td>3</td>\n",
       "      <td>1</td>\n",
       "      <td>carbon dioxide</td>\n",
       "      <td>AAIYzl</td>\n",
       "      <td>O=C=O</td>\n",
       "      <td>water</td>\n",
       "      <td>AADYJk</td>\n",
       "      <td>O</td>\n",
       "      <td>2-hydroxy-N-(2-hydroxyethyl)-N-methylethanamin...</td>\n",
       "      <td>AAdwMT</td>\n",
       "      <td>C[NH+](CCO)CCO.[Cl-]</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>54205</th>\n",
       "      <td>WDULW</td>\n",
       "      <td>Zhao et al. (2010a)</td>\n",
       "      <td>Composition at phase equilibrium</td>\n",
       "      <td>Liquid;Gas</td>\n",
       "      <td>2</td>\n",
       "      <td>3</td>\n",
       "      <td>1</td>\n",
       "      <td>carbon dioxide</td>\n",
       "      <td>AAIYzl</td>\n",
       "      <td>O=C=O</td>\n",
       "      <td>water</td>\n",
       "      <td>AADYJk</td>\n",
       "      <td>O</td>\n",
       "      <td>2-hydroxy-N-(2-hydroxyethyl)-N-methylethanamin...</td>\n",
       "      <td>AAnpCD</td>\n",
       "      <td>C[NH+](CCO)CCO.F[B-](F)(F)F</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>54206</th>\n",
       "      <td>trauR</td>\n",
       "      <td>Zhao et al. (2010a)</td>\n",
       "      <td>Composition at phase equilibrium</td>\n",
       "      <td>Liquid;Gas</td>\n",
       "      <td>2</td>\n",
       "      <td>3</td>\n",
       "      <td>1</td>\n",
       "      <td>carbon dioxide</td>\n",
       "      <td>AAIYzl</td>\n",
       "      <td>O=C=O</td>\n",
       "      <td>water</td>\n",
       "      <td>AADYJk</td>\n",
       "      <td>O</td>\n",
       "      <td>2-hydroxyethanaminium tetrafluoroborate</td>\n",
       "      <td>AAcgPC</td>\n",
       "      <td>F[B-](F)(F)F.[NH3+]CCO</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>54207</th>\n",
       "      <td>YtOdr</td>\n",
       "      <td>Zhao et al. (2010a)</td>\n",
       "      <td>Composition at phase equilibrium</td>\n",
       "      <td>Liquid;Gas</td>\n",
       "      <td>2</td>\n",
       "      <td>3</td>\n",
       "      <td>1</td>\n",
       "      <td>carbon dioxide</td>\n",
       "      <td>AAIYzl</td>\n",
       "      <td>O=C=O</td>\n",
       "      <td>water</td>\n",
       "      <td>AADYJk</td>\n",
       "      <td>O</td>\n",
       "      <td>1-butyl-3-methylimidazolium tetrafluoroborate</td>\n",
       "      <td>AArYBF</td>\n",
       "      <td>CCCC[n+]1ccn(C)c1.F[B-](F)(F)F</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>54208</th>\n",
       "      <td>xKyGC</td>\n",
       "      <td>Zhao et al. (2010a)</td>\n",
       "      <td>Composition at phase equilibrium</td>\n",
       "      <td>Liquid;Gas</td>\n",
       "      <td>2</td>\n",
       "      <td>3</td>\n",
       "      <td>1</td>\n",
       "      <td>triethanolamine</td>\n",
       "      <td>AAcjhv</td>\n",
       "      <td>OCCN(CCO)CCO</td>\n",
       "      <td>carbon dioxide</td>\n",
       "      <td>AAIYzl</td>\n",
       "      <td>O=C=O</td>\n",
       "      <td>1-butyl-3-methylimidazolium tetrafluoroborate</td>\n",
       "      <td>AArYBF</td>\n",
       "      <td>CCCC[n+]1ccn(C)c1.F[B-](F)(F)F</td>\n",
       "    </tr>\n",
       "  </tbody>\n",
       "</table>\n",
       "<p>54209 rows × 16 columns</p>\n",
       "</div>"
      ],
      "text/plain": [
       "          id                   reference  \\\n",
       "0      vffQK          Kabo et al. (2004)   \n",
       "1      cFdQS     Strechan et al. (2008a)   \n",
       "2      eOKLZ      Safarov et al. (2021b)   \n",
       "3      UkHsx  Polikhronidi et al. (2014)   \n",
       "4      BvazU      Safarov et al. (2018c)   \n",
       "...      ...                         ...   \n",
       "54204  kxodn         Zhao et al. (2010a)   \n",
       "54205  WDULW         Zhao et al. (2010a)   \n",
       "54206  trauR         Zhao et al. (2010a)   \n",
       "54207  YtOdr         Zhao et al. (2010a)   \n",
       "54208  xKyGC         Zhao et al. (2010a)   \n",
       "\n",
       "                                         property         phases  num_phases  \\\n",
       "0              Heat capacity at constant pressure         Liquid           1   \n",
       "1      Heat capacity at vapor saturation pressure  Crystal 2;Gas           2   \n",
       "2                                       Viscosity         Liquid           1   \n",
       "3              Heat capacity at constant pressure         Liquid           1   \n",
       "4                                       Viscosity         Liquid           1   \n",
       "...                                           ...            ...         ...   \n",
       "54204            Composition at phase equilibrium     Liquid;Gas           2   \n",
       "54205            Composition at phase equilibrium     Liquid;Gas           2   \n",
       "54206            Composition at phase equilibrium     Liquid;Gas           2   \n",
       "54207            Composition at phase equilibrium     Liquid;Gas           2   \n",
       "54208            Composition at phase equilibrium     Liquid;Gas           2   \n",
       "\n",
       "       num_components  num_data_points  \\\n",
       "0                   1             1528   \n",
       "1                   1              613   \n",
       "2                   1              500   \n",
       "3                   1              422   \n",
       "4                   1              394   \n",
       "...               ...              ...   \n",
       "54204               3                1   \n",
       "54205               3                1   \n",
       "54206               3                1   \n",
       "54207               3                1   \n",
       "54208               3                1   \n",
       "\n",
       "                                                    cmp1 cmp1_id  \\\n",
       "0        1-butyl-3-methylimidazolium hexafluorophosphate  ABChJv   \n",
       "1           1-butyl-3-methylimidazolium trifluoroacetate  AAwaEi   \n",
       "2                1-ethyl-3-methylimidazolium dicyanamide  AAiEIE   \n",
       "3      1-hexyl-3-methylimidazolium bis[(trifluorometh...  ABiCtA   \n",
       "4        1-octyl-3-methylimidazolium hexafluorophosphate  ABNWoR   \n",
       "...                                                  ...     ...   \n",
       "54204                                     carbon dioxide  AAIYzl   \n",
       "54205                                     carbon dioxide  AAIYzl   \n",
       "54206                                     carbon dioxide  AAIYzl   \n",
       "54207                                     carbon dioxide  AAIYzl   \n",
       "54208                                    triethanolamine  AAcjhv   \n",
       "\n",
       "                                             cmp1_smiles            cmp2  \\\n",
       "0                   CCCC[n+]1ccn(C)c1.F[P-](F)(F)(F)(F)F            None   \n",
       "1                    CCCC[n+]1ccn(C)c1.O=C([O-])C(F)(F)F            None   \n",
       "2                             CC[n+]1ccn(C)c1.N#C[N-]C#N            None   \n",
       "3      CCCCCC[n+]1ccn(C)c1.O=S(=O)([N-]S(=O)(=O)C(F)(...            None   \n",
       "4               CCCCCCCC[n+]1ccn(C)c1.F[P-](F)(F)(F)(F)F            None   \n",
       "...                                                  ...             ...   \n",
       "54204                                              O=C=O           water   \n",
       "54205                                              O=C=O           water   \n",
       "54206                                              O=C=O           water   \n",
       "54207                                              O=C=O           water   \n",
       "54208                                       OCCN(CCO)CCO  carbon dioxide   \n",
       "\n",
       "      cmp2_id cmp2_smiles                                               cmp3  \\\n",
       "0        None        None                                               None   \n",
       "1        None        None                                               None   \n",
       "2        None        None                                               None   \n",
       "3        None        None                                               None   \n",
       "4        None        None                                               None   \n",
       "...       ...         ...                                                ...   \n",
       "54204  AADYJk           O  2-hydroxy-N-(2-hydroxyethyl)-N-methylethanamin...   \n",
       "54205  AADYJk           O  2-hydroxy-N-(2-hydroxyethyl)-N-methylethanamin...   \n",
       "54206  AADYJk           O            2-hydroxyethanaminium tetrafluoroborate   \n",
       "54207  AADYJk           O      1-butyl-3-methylimidazolium tetrafluoroborate   \n",
       "54208  AAIYzl       O=C=O      1-butyl-3-methylimidazolium tetrafluoroborate   \n",
       "\n",
       "      cmp3_id                     cmp3_smiles  \n",
       "0        None                            None  \n",
       "1        None                            None  \n",
       "2        None                            None  \n",
       "3        None                            None  \n",
       "4        None                            None  \n",
       "...       ...                             ...  \n",
       "54204  AAdwMT            C[NH+](CCO)CCO.[Cl-]  \n",
       "54205  AAnpCD     C[NH+](CCO)CCO.F[B-](F)(F)F  \n",
       "54206  AAcgPC          F[B-](F)(F)F.[NH3+]CCO  \n",
       "54207  AArYBF  CCCC[n+]1ccn(C)c1.F[B-](F)(F)F  \n",
       "54208  AArYBF  CCCC[n+]1ccn(C)c1.F[B-](F)(F)F  \n",
       "\n",
       "[54209 rows x 16 columns]"
      ]
     },
     "execution_count": 12,
     "metadata": {},
     "output_type": "execute_result"
    }
   ],
   "source": [
    "df = ilt.GetAllEntries()\n",
    "df"
   ]
  },
  {
   "cell_type": "markdown",
   "id": "971f1b3b",
   "metadata": {},
   "source": [
    "Next we get pre-stored list of all ILThermo compounds:"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 13,
   "id": "eaf23ad7",
   "metadata": {},
   "outputs": [
    {
     "data": {
      "text/html": [
       "<div>\n",
       "<style scoped>\n",
       "    .dataframe tbody tr th:only-of-type {\n",
       "        vertical-align: middle;\n",
       "    }\n",
       "\n",
       "    .dataframe tbody tr th {\n",
       "        vertical-align: top;\n",
       "    }\n",
       "\n",
       "    .dataframe thead th {\n",
       "        text-align: right;\n",
       "    }\n",
       "</style>\n",
       "<table border=\"1\" class=\"dataframe\">\n",
       "  <thead>\n",
       "    <tr style=\"text-align: right;\">\n",
       "      <th></th>\n",
       "      <th>id</th>\n",
       "      <th>name</th>\n",
       "      <th>smiles</th>\n",
       "    </tr>\n",
       "  </thead>\n",
       "  <tbody>\n",
       "    <tr>\n",
       "      <th>0</th>\n",
       "      <td>AAAUum</td>\n",
       "      <td>hydrogen (normal)</td>\n",
       "      <td>[HH]</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>1</th>\n",
       "      <td>AAAomx</td>\n",
       "      <td>helium</td>\n",
       "      <td>[He]</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>2</th>\n",
       "      <td>AADEIK</td>\n",
       "      <td>methane</td>\n",
       "      <td>C</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>3</th>\n",
       "      <td>AADOkx</td>\n",
       "      <td>ammonia</td>\n",
       "      <td>N</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>4</th>\n",
       "      <td>AADYJk</td>\n",
       "      <td>water</td>\n",
       "      <td>O</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>...</th>\n",
       "      <td>...</td>\n",
       "      <td>...</td>\n",
       "      <td>...</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>4110</th>\n",
       "      <td>AFHNfv</td>\n",
       "      <td>1,3-bis(3-((3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,...</td>\n",
       "      <td>FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F...</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>4111</th>\n",
       "      <td>AFSFfi</td>\n",
       "      <td>3,3',3''-((propane-1,2,3-triyltris(oxy))tris(m...</td>\n",
       "      <td>O=S(=O)([N-]S(=O)(=O)C(F)(F)F)C(F)(F)F.O=S(=O)...</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>4112</th>\n",
       "      <td>AFmxJi</td>\n",
       "      <td>3,3',3''-((propane-1,2,3-triyltris(oxy))tris(m...</td>\n",
       "      <td>CCCCCCCC[n+]1ccn(COCC(COCn2cc[n+](CCCCCCCC)c2C...</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>4113</th>\n",
       "      <td>AGbVrm</td>\n",
       "      <td>1,1'-(ethane-1,2-diyl)bis(3-(3-((3,3,4,4,5,5,6...</td>\n",
       "      <td>FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F...</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>4114</th>\n",
       "      <td>AGwzVJ</td>\n",
       "      <td>1,1'-(decane-1,10-diyl)bis(3-(3-((3,3,4,4,5,5,...</td>\n",
       "      <td>FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F...</td>\n",
       "    </tr>\n",
       "  </tbody>\n",
       "</table>\n",
       "<p>4115 rows × 3 columns</p>\n",
       "</div>"
      ],
      "text/plain": [
       "          id                                               name  \\\n",
       "0     AAAUum                                  hydrogen (normal)   \n",
       "1     AAAomx                                             helium   \n",
       "2     AADEIK                                            methane   \n",
       "3     AADOkx                                            ammonia   \n",
       "4     AADYJk                                              water   \n",
       "...      ...                                                ...   \n",
       "4110  AFHNfv  1,3-bis(3-((3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,...   \n",
       "4111  AFSFfi  3,3',3''-((propane-1,2,3-triyltris(oxy))tris(m...   \n",
       "4112  AFmxJi  3,3',3''-((propane-1,2,3-triyltris(oxy))tris(m...   \n",
       "4113  AGbVrm  1,1'-(ethane-1,2-diyl)bis(3-(3-((3,3,4,4,5,5,6...   \n",
       "4114  AGwzVJ  1,1'-(decane-1,10-diyl)bis(3-(3-((3,3,4,4,5,5,...   \n",
       "\n",
       "                                                 smiles  \n",
       "0                                                  [HH]  \n",
       "1                                                  [He]  \n",
       "2                                                     C  \n",
       "3                                                     N  \n",
       "4                                                     O  \n",
       "...                                                 ...  \n",
       "4110  FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F...  \n",
       "4111  O=S(=O)([N-]S(=O)(=O)C(F)(F)F)C(F)(F)F.O=S(=O)...  \n",
       "4112  CCCCCCCC[n+]1ccn(COCC(COCn2cc[n+](CCCCCCCC)c2C...  \n",
       "4113  FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F...  \n",
       "4114  FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F...  \n",
       "\n",
       "[4115 rows x 3 columns]"
      ]
     },
     "execution_count": 13,
     "metadata": {},
     "output_type": "execute_result"
    }
   ],
   "source": [
    "cmps = ilt.GetSavedCompounds().data\n",
    "cmps"
   ]
  },
  {
   "cell_type": "markdown",
   "id": "18f6eb6b",
   "metadata": {},
   "source": [
    "And filter them with RDKit package using a substucture search:"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 14,
   "id": "698399f4",
   "metadata": {},
   "outputs": [
    {
     "data": {
      "text/html": [
       "<div>\n",
       "<style scoped>\n",
       "    .dataframe tbody tr th:only-of-type {\n",
       "        vertical-align: middle;\n",
       "    }\n",
       "\n",
       "    .dataframe tbody tr th {\n",
       "        vertical-align: top;\n",
       "    }\n",
       "\n",
       "    .dataframe thead th {\n",
       "        text-align: right;\n",
       "    }\n",
       "</style>\n",
       "<table border=\"1\" class=\"dataframe\">\n",
       "  <thead>\n",
       "    <tr style=\"text-align: right;\">\n",
       "      <th></th>\n",
       "      <th>id</th>\n",
       "      <th>name</th>\n",
       "      <th>smiles</th>\n",
       "    </tr>\n",
       "  </thead>\n",
       "  <tbody>\n",
       "    <tr>\n",
       "      <th>595</th>\n",
       "      <td>AAavNv</td>\n",
       "      <td>Guanidinium bromide</td>\n",
       "      <td>NC(N)=[NH2+].[Br-]</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>1159</th>\n",
       "      <td>AAoLEA</td>\n",
       "      <td>guanidinium trifluoromethanesulfonate</td>\n",
       "      <td>NC(N)=[NH2+].O=S(=O)([O-])C(F)(F)F</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>1243</th>\n",
       "      <td>AApejX</td>\n",
       "      <td>guanidinium sulfate</td>\n",
       "      <td>NC(N)=[NH2+].NC(N)=[NH2+].O=S(=O)([O-])[O-]</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>2728</th>\n",
       "      <td>ABUxBz</td>\n",
       "      <td>guanidinium tetraphenylborate</td>\n",
       "      <td>NC(N)=[NH2+].c1ccc([B-](c2ccccc2)(c2ccccc2)c2c...</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>3923</th>\n",
       "      <td>ACTsEp</td>\n",
       "      <td>guanidinium bis(bis(perfluoroethyl)phosphoryl)...</td>\n",
       "      <td>NC(N)=[NH2+].O=P([N-]P(=O)(C(F)(F)C(F)(F)F)C(F...</td>\n",
       "    </tr>\n",
       "  </tbody>\n",
       "</table>\n",
       "</div>"
      ],
      "text/plain": [
       "          id                                               name  \\\n",
       "595   AAavNv                                Guanidinium bromide   \n",
       "1159  AAoLEA              guanidinium trifluoromethanesulfonate   \n",
       "1243  AApejX                                guanidinium sulfate   \n",
       "2728  ABUxBz                      guanidinium tetraphenylborate   \n",
       "3923  ACTsEp  guanidinium bis(bis(perfluoroethyl)phosphoryl)...   \n",
       "\n",
       "                                                 smiles  \n",
       "595                                  NC(N)=[NH2+].[Br-]  \n",
       "1159                 NC(N)=[NH2+].O=S(=O)([O-])C(F)(F)F  \n",
       "1243        NC(N)=[NH2+].NC(N)=[NH2+].O=S(=O)([O-])[O-]  \n",
       "2728  NC(N)=[NH2+].c1ccc([B-](c2ccccc2)(c2ccccc2)c2c...  \n",
       "3923  NC(N)=[NH2+].O=P([N-]P(=O)(C(F)(F)C(F)(F)F)C(F...  "
      ]
     },
     "execution_count": 14,
     "metadata": {},
     "output_type": "execute_result"
    }
   ],
   "source": [
    "from rdkit import Chem\n",
    "from rdkit import RDLogger\n",
    "RDLogger.DisableLog('rdApp.*') # hides warnings\n",
    "\n",
    "mols = [Chem.MolFromSmiles(smi) for smi in cmps.smiles]\n",
    "pat = Chem.MolFromSmarts('[NX3;H2]~[CX3](~[NX3;H2])~[NX3;H2]')\n",
    "cmps = cmps.loc[[m.HasSubstructMatch(pat) for m in mols]]\n",
    "cmps"
   ]
  },
  {
   "cell_type": "markdown",
   "id": "b8c47fe8",
   "metadata": {},
   "source": [
    "Now we can use obtained compound IDs to filter the search data:"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 15,
   "id": "6e3b2c96",
   "metadata": {},
   "outputs": [
    {
     "data": {
      "text/html": [
       "<div>\n",
       "<style scoped>\n",
       "    .dataframe tbody tr th:only-of-type {\n",
       "        vertical-align: middle;\n",
       "    }\n",
       "\n",
       "    .dataframe tbody tr th {\n",
       "        vertical-align: top;\n",
       "    }\n",
       "\n",
       "    .dataframe thead th {\n",
       "        text-align: right;\n",
       "    }\n",
       "</style>\n",
       "<table border=\"1\" class=\"dataframe\">\n",
       "  <thead>\n",
       "    <tr style=\"text-align: right;\">\n",
       "      <th></th>\n",
       "      <th>id</th>\n",
       "      <th>reference</th>\n",
       "      <th>property</th>\n",
       "      <th>phases</th>\n",
       "      <th>num_phases</th>\n",
       "      <th>num_components</th>\n",
       "      <th>num_data_points</th>\n",
       "      <th>cmp1</th>\n",
       "      <th>cmp1_id</th>\n",
       "      <th>cmp1_smiles</th>\n",
       "      <th>cmp2</th>\n",
       "      <th>cmp2_id</th>\n",
       "      <th>cmp2_smiles</th>\n",
       "      <th>cmp3</th>\n",
       "      <th>cmp3_id</th>\n",
       "      <th>cmp3_smiles</th>\n",
       "    </tr>\n",
       "  </thead>\n",
       "  <tbody>\n",
       "    <tr>\n",
       "      <th>22465</th>\n",
       "      <td>FTOEm</td>\n",
       "      <td>Kumar (2007)</td>\n",
       "      <td>Osmotic coefficient</td>\n",
       "      <td>Liquid;Gas</td>\n",
       "      <td>2</td>\n",
       "      <td>2</td>\n",
       "      <td>28</td>\n",
       "      <td>tetramethylammonium chloride</td>\n",
       "      <td>AAVDUE</td>\n",
       "      <td>C[N+](C)(C)C.[Cl-]</td>\n",
       "      <td>guanidinium sulfate</td>\n",
       "      <td>AApejX</td>\n",
       "      <td>NC(N)=[NH2+].NC(N)=[NH2+].O=S(=O)([O-])[O-]</td>\n",
       "      <td>None</td>\n",
       "      <td>None</td>\n",
       "      <td>None</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>22503</th>\n",
       "      <td>eBeqe</td>\n",
       "      <td>Sairi et al. (2015)</td>\n",
       "      <td>Viscosity</td>\n",
       "      <td>Liquid</td>\n",
       "      <td>1</td>\n",
       "      <td>2</td>\n",
       "      <td>28</td>\n",
       "      <td>water</td>\n",
       "      <td>AADYJk</td>\n",
       "      <td>O</td>\n",
       "      <td>guanidinium trifluoromethanesulfonate</td>\n",
       "      <td>AAoLEA</td>\n",
       "      <td>NC(N)=[NH2+].O=S(=O)([O-])C(F)(F)F</td>\n",
       "      <td>None</td>\n",
       "      <td>None</td>\n",
       "      <td>None</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>23959</th>\n",
       "      <td>KDBmV</td>\n",
       "      <td>Sairi et al. (2015)</td>\n",
       "      <td>Density</td>\n",
       "      <td>Liquid</td>\n",
       "      <td>1</td>\n",
       "      <td>2</td>\n",
       "      <td>18</td>\n",
       "      <td>water</td>\n",
       "      <td>AADYJk</td>\n",
       "      <td>O</td>\n",
       "      <td>guanidinium trifluoromethanesulfonate</td>\n",
       "      <td>AAoLEA</td>\n",
       "      <td>NC(N)=[NH2+].O=S(=O)([O-])C(F)(F)F</td>\n",
       "      <td>None</td>\n",
       "      <td>None</td>\n",
       "      <td>None</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>24985</th>\n",
       "      <td>vQDiO</td>\n",
       "      <td>Kumar (2001)</td>\n",
       "      <td>Density</td>\n",
       "      <td>Liquid</td>\n",
       "      <td>1</td>\n",
       "      <td>2</td>\n",
       "      <td>14</td>\n",
       "      <td>water</td>\n",
       "      <td>AADYJk</td>\n",
       "      <td>O</td>\n",
       "      <td>Guanidinium bromide</td>\n",
       "      <td>AAavNv</td>\n",
       "      <td>NC(N)=[NH2+].[Br-]</td>\n",
       "      <td>None</td>\n",
       "      <td>None</td>\n",
       "      <td>None</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>24986</th>\n",
       "      <td>MNutD</td>\n",
       "      <td>Kumar (2001)</td>\n",
       "      <td>Speed of sound</td>\n",
       "      <td>Liquid</td>\n",
       "      <td>1</td>\n",
       "      <td>2</td>\n",
       "      <td>14</td>\n",
       "      <td>water</td>\n",
       "      <td>AADYJk</td>\n",
       "      <td>O</td>\n",
       "      <td>Guanidinium bromide</td>\n",
       "      <td>AAavNv</td>\n",
       "      <td>NC(N)=[NH2+].[Br-]</td>\n",
       "      <td>None</td>\n",
       "      <td>None</td>\n",
       "      <td>None</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>25429</th>\n",
       "      <td>jASaU</td>\n",
       "      <td>Kumar (2001)</td>\n",
       "      <td>Speed of sound</td>\n",
       "      <td>Liquid</td>\n",
       "      <td>1</td>\n",
       "      <td>2</td>\n",
       "      <td>13</td>\n",
       "      <td>guanidinium sulfate</td>\n",
       "      <td>AApejX</td>\n",
       "      <td>NC(N)=[NH2+].NC(N)=[NH2+].O=S(=O)([O-])[O-]</td>\n",
       "      <td>water</td>\n",
       "      <td>AADYJk</td>\n",
       "      <td>O</td>\n",
       "      <td>None</td>\n",
       "      <td>None</td>\n",
       "      <td>None</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>25430</th>\n",
       "      <td>kKajm</td>\n",
       "      <td>Kumar (2001)</td>\n",
       "      <td>Density</td>\n",
       "      <td>Liquid</td>\n",
       "      <td>1</td>\n",
       "      <td>2</td>\n",
       "      <td>13</td>\n",
       "      <td>guanidinium sulfate</td>\n",
       "      <td>AApejX</td>\n",
       "      <td>NC(N)=[NH2+].NC(N)=[NH2+].O=S(=O)([O-])[O-]</td>\n",
       "      <td>water</td>\n",
       "      <td>AADYJk</td>\n",
       "      <td>O</td>\n",
       "      <td>None</td>\n",
       "      <td>None</td>\n",
       "      <td>None</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>45701</th>\n",
       "      <td>MhEvz</td>\n",
       "      <td>Ondo and Dohnal (2014)</td>\n",
       "      <td>Composition at phase equilibrium</td>\n",
       "      <td>Liquid;Crystal of intercomponent compound 1</td>\n",
       "      <td>2</td>\n",
       "      <td>2</td>\n",
       "      <td>1</td>\n",
       "      <td>water</td>\n",
       "      <td>AADYJk</td>\n",
       "      <td>O</td>\n",
       "      <td>guanidinium tetraphenylborate</td>\n",
       "      <td>ABUxBz</td>\n",
       "      <td>NC(N)=[NH2+].c1ccc([B-](c2ccccc2)(c2ccccc2)c2c...</td>\n",
       "      <td>None</td>\n",
       "      <td>None</td>\n",
       "      <td>None</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>45702</th>\n",
       "      <td>BVhqX</td>\n",
       "      <td>Ondo and Dohnal (2014)</td>\n",
       "      <td>Composition at phase equilibrium</td>\n",
       "      <td>Liquid;Crystal of pure component 2</td>\n",
       "      <td>2</td>\n",
       "      <td>2</td>\n",
       "      <td>1</td>\n",
       "      <td>water</td>\n",
       "      <td>AADYJk</td>\n",
       "      <td>O</td>\n",
       "      <td>guanidinium bis(bis(perfluoroethyl)phosphoryl)...</td>\n",
       "      <td>ACTsEp</td>\n",
       "      <td>NC(N)=[NH2+].O=P([N-]P(=O)(C(F)(F)C(F)(F)F)C(F...</td>\n",
       "      <td>None</td>\n",
       "      <td>None</td>\n",
       "      <td>None</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>45709</th>\n",
       "      <td>hRmeZ</td>\n",
       "      <td>Ondo and Dohnal (2014)</td>\n",
       "      <td>Apparent enthalpy</td>\n",
       "      <td>Liquid</td>\n",
       "      <td>1</td>\n",
       "      <td>2</td>\n",
       "      <td>1</td>\n",
       "      <td>water</td>\n",
       "      <td>AADYJk</td>\n",
       "      <td>O</td>\n",
       "      <td>guanidinium tetraphenylborate</td>\n",
       "      <td>ABUxBz</td>\n",
       "      <td>NC(N)=[NH2+].c1ccc([B-](c2ccccc2)(c2ccccc2)c2c...</td>\n",
       "      <td>None</td>\n",
       "      <td>None</td>\n",
       "      <td>None</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>45710</th>\n",
       "      <td>arrKj</td>\n",
       "      <td>Ondo and Dohnal (2014)</td>\n",
       "      <td>Apparent enthalpy</td>\n",
       "      <td>Liquid</td>\n",
       "      <td>1</td>\n",
       "      <td>2</td>\n",
       "      <td>1</td>\n",
       "      <td>water</td>\n",
       "      <td>AADYJk</td>\n",
       "      <td>O</td>\n",
       "      <td>guanidinium bis(bis(perfluoroethyl)phosphoryl)...</td>\n",
       "      <td>ACTsEp</td>\n",
       "      <td>NC(N)=[NH2+].O=P([N-]P(=O)(C(F)(F)C(F)(F)F)C(F...</td>\n",
       "      <td>None</td>\n",
       "      <td>None</td>\n",
       "      <td>None</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>47776</th>\n",
       "      <td>aWGeF</td>\n",
       "      <td>Sairi et al. (2015)</td>\n",
       "      <td>Density</td>\n",
       "      <td>Liquid</td>\n",
       "      <td>1</td>\n",
       "      <td>3</td>\n",
       "      <td>81</td>\n",
       "      <td>N-methyldiethanolamine</td>\n",
       "      <td>AAWveB</td>\n",
       "      <td>CN(CCO)CCO</td>\n",
       "      <td>water</td>\n",
       "      <td>AADYJk</td>\n",
       "      <td>O</td>\n",
       "      <td>guanidinium trifluoromethanesulfonate</td>\n",
       "      <td>AAoLEA</td>\n",
       "      <td>NC(N)=[NH2+].O=S(=O)([O-])C(F)(F)F</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>48534</th>\n",
       "      <td>woUWv</td>\n",
       "      <td>Sairi et al. (2015)</td>\n",
       "      <td>Viscosity</td>\n",
       "      <td>Liquid</td>\n",
       "      <td>1</td>\n",
       "      <td>3</td>\n",
       "      <td>48</td>\n",
       "      <td>N-methyldiethanolamine</td>\n",
       "      <td>AAWveB</td>\n",
       "      <td>CN(CCO)CCO</td>\n",
       "      <td>water</td>\n",
       "      <td>AADYJk</td>\n",
       "      <td>O</td>\n",
       "      <td>guanidinium trifluoromethanesulfonate</td>\n",
       "      <td>AAoLEA</td>\n",
       "      <td>NC(N)=[NH2+].O=S(=O)([O-])C(F)(F)F</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>50285</th>\n",
       "      <td>zoJjS</td>\n",
       "      <td>Sairi et al. (2011)</td>\n",
       "      <td>Composition at phase equilibrium</td>\n",
       "      <td>Liquid;Gas</td>\n",
       "      <td>2</td>\n",
       "      <td>3</td>\n",
       "      <td>18</td>\n",
       "      <td>carbon dioxide</td>\n",
       "      <td>AAIYzl</td>\n",
       "      <td>O=C=O</td>\n",
       "      <td>water</td>\n",
       "      <td>AADYJk</td>\n",
       "      <td>O</td>\n",
       "      <td>guanidinium trifluoromethanesulfonate</td>\n",
       "      <td>AAoLEA</td>\n",
       "      <td>NC(N)=[NH2+].O=S(=O)([O-])C(F)(F)F</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>52324</th>\n",
       "      <td>tmQgx</td>\n",
       "      <td>Sairi et al. (2015)</td>\n",
       "      <td>Composition at phase equilibrium</td>\n",
       "      <td>Liquid;Gas</td>\n",
       "      <td>2</td>\n",
       "      <td>3</td>\n",
       "      <td>6</td>\n",
       "      <td>carbon dioxide</td>\n",
       "      <td>AAIYzl</td>\n",
       "      <td>O=C=O</td>\n",
       "      <td>water</td>\n",
       "      <td>AADYJk</td>\n",
       "      <td>O</td>\n",
       "      <td>guanidinium trifluoromethanesulfonate</td>\n",
       "      <td>AAoLEA</td>\n",
       "      <td>NC(N)=[NH2+].O=S(=O)([O-])C(F)(F)F</td>\n",
       "    </tr>\n",
       "  </tbody>\n",
       "</table>\n",
       "</div>"
      ],
      "text/plain": [
       "          id               reference                          property  \\\n",
       "22465  FTOEm            Kumar (2007)               Osmotic coefficient   \n",
       "22503  eBeqe     Sairi et al. (2015)                         Viscosity   \n",
       "23959  KDBmV     Sairi et al. (2015)                           Density   \n",
       "24985  vQDiO            Kumar (2001)                           Density   \n",
       "24986  MNutD            Kumar (2001)                    Speed of sound   \n",
       "25429  jASaU            Kumar (2001)                    Speed of sound   \n",
       "25430  kKajm            Kumar (2001)                           Density   \n",
       "45701  MhEvz  Ondo and Dohnal (2014)  Composition at phase equilibrium   \n",
       "45702  BVhqX  Ondo and Dohnal (2014)  Composition at phase equilibrium   \n",
       "45709  hRmeZ  Ondo and Dohnal (2014)                 Apparent enthalpy   \n",
       "45710  arrKj  Ondo and Dohnal (2014)                 Apparent enthalpy   \n",
       "47776  aWGeF     Sairi et al. (2015)                           Density   \n",
       "48534  woUWv     Sairi et al. (2015)                         Viscosity   \n",
       "50285  zoJjS     Sairi et al. (2011)  Composition at phase equilibrium   \n",
       "52324  tmQgx     Sairi et al. (2015)  Composition at phase equilibrium   \n",
       "\n",
       "                                            phases  num_phases  \\\n",
       "22465                                   Liquid;Gas           2   \n",
       "22503                                       Liquid           1   \n",
       "23959                                       Liquid           1   \n",
       "24985                                       Liquid           1   \n",
       "24986                                       Liquid           1   \n",
       "25429                                       Liquid           1   \n",
       "25430                                       Liquid           1   \n",
       "45701  Liquid;Crystal of intercomponent compound 1           2   \n",
       "45702           Liquid;Crystal of pure component 2           2   \n",
       "45709                                       Liquid           1   \n",
       "45710                                       Liquid           1   \n",
       "47776                                       Liquid           1   \n",
       "48534                                       Liquid           1   \n",
       "50285                                   Liquid;Gas           2   \n",
       "52324                                   Liquid;Gas           2   \n",
       "\n",
       "       num_components  num_data_points                          cmp1 cmp1_id  \\\n",
       "22465               2               28  tetramethylammonium chloride  AAVDUE   \n",
       "22503               2               28                         water  AADYJk   \n",
       "23959               2               18                         water  AADYJk   \n",
       "24985               2               14                         water  AADYJk   \n",
       "24986               2               14                         water  AADYJk   \n",
       "25429               2               13           guanidinium sulfate  AApejX   \n",
       "25430               2               13           guanidinium sulfate  AApejX   \n",
       "45701               2                1                         water  AADYJk   \n",
       "45702               2                1                         water  AADYJk   \n",
       "45709               2                1                         water  AADYJk   \n",
       "45710               2                1                         water  AADYJk   \n",
       "47776               3               81        N-methyldiethanolamine  AAWveB   \n",
       "48534               3               48        N-methyldiethanolamine  AAWveB   \n",
       "50285               3               18                carbon dioxide  AAIYzl   \n",
       "52324               3                6                carbon dioxide  AAIYzl   \n",
       "\n",
       "                                       cmp1_smiles  \\\n",
       "22465                           C[N+](C)(C)C.[Cl-]   \n",
       "22503                                            O   \n",
       "23959                                            O   \n",
       "24985                                            O   \n",
       "24986                                            O   \n",
       "25429  NC(N)=[NH2+].NC(N)=[NH2+].O=S(=O)([O-])[O-]   \n",
       "25430  NC(N)=[NH2+].NC(N)=[NH2+].O=S(=O)([O-])[O-]   \n",
       "45701                                            O   \n",
       "45702                                            O   \n",
       "45709                                            O   \n",
       "45710                                            O   \n",
       "47776                                   CN(CCO)CCO   \n",
       "48534                                   CN(CCO)CCO   \n",
       "50285                                        O=C=O   \n",
       "52324                                        O=C=O   \n",
       "\n",
       "                                                    cmp2 cmp2_id  \\\n",
       "22465                                guanidinium sulfate  AApejX   \n",
       "22503              guanidinium trifluoromethanesulfonate  AAoLEA   \n",
       "23959              guanidinium trifluoromethanesulfonate  AAoLEA   \n",
       "24985                                Guanidinium bromide  AAavNv   \n",
       "24986                                Guanidinium bromide  AAavNv   \n",
       "25429                                              water  AADYJk   \n",
       "25430                                              water  AADYJk   \n",
       "45701                      guanidinium tetraphenylborate  ABUxBz   \n",
       "45702  guanidinium bis(bis(perfluoroethyl)phosphoryl)...  ACTsEp   \n",
       "45709                      guanidinium tetraphenylborate  ABUxBz   \n",
       "45710  guanidinium bis(bis(perfluoroethyl)phosphoryl)...  ACTsEp   \n",
       "47776                                              water  AADYJk   \n",
       "48534                                              water  AADYJk   \n",
       "50285                                              water  AADYJk   \n",
       "52324                                              water  AADYJk   \n",
       "\n",
       "                                             cmp2_smiles  \\\n",
       "22465        NC(N)=[NH2+].NC(N)=[NH2+].O=S(=O)([O-])[O-]   \n",
       "22503                 NC(N)=[NH2+].O=S(=O)([O-])C(F)(F)F   \n",
       "23959                 NC(N)=[NH2+].O=S(=O)([O-])C(F)(F)F   \n",
       "24985                                 NC(N)=[NH2+].[Br-]   \n",
       "24986                                 NC(N)=[NH2+].[Br-]   \n",
       "25429                                                  O   \n",
       "25430                                                  O   \n",
       "45701  NC(N)=[NH2+].c1ccc([B-](c2ccccc2)(c2ccccc2)c2c...   \n",
       "45702  NC(N)=[NH2+].O=P([N-]P(=O)(C(F)(F)C(F)(F)F)C(F...   \n",
       "45709  NC(N)=[NH2+].c1ccc([B-](c2ccccc2)(c2ccccc2)c2c...   \n",
       "45710  NC(N)=[NH2+].O=P([N-]P(=O)(C(F)(F)C(F)(F)F)C(F...   \n",
       "47776                                                  O   \n",
       "48534                                                  O   \n",
       "50285                                                  O   \n",
       "52324                                                  O   \n",
       "\n",
       "                                        cmp3 cmp3_id  \\\n",
       "22465                                   None    None   \n",
       "22503                                   None    None   \n",
       "23959                                   None    None   \n",
       "24985                                   None    None   \n",
       "24986                                   None    None   \n",
       "25429                                   None    None   \n",
       "25430                                   None    None   \n",
       "45701                                   None    None   \n",
       "45702                                   None    None   \n",
       "45709                                   None    None   \n",
       "45710                                   None    None   \n",
       "47776  guanidinium trifluoromethanesulfonate  AAoLEA   \n",
       "48534  guanidinium trifluoromethanesulfonate  AAoLEA   \n",
       "50285  guanidinium trifluoromethanesulfonate  AAoLEA   \n",
       "52324  guanidinium trifluoromethanesulfonate  AAoLEA   \n",
       "\n",
       "                              cmp3_smiles  \n",
       "22465                                None  \n",
       "22503                                None  \n",
       "23959                                None  \n",
       "24985                                None  \n",
       "24986                                None  \n",
       "25429                                None  \n",
       "25430                                None  \n",
       "45701                                None  \n",
       "45702                                None  \n",
       "45709                                None  \n",
       "45710                                None  \n",
       "47776  NC(N)=[NH2+].O=S(=O)([O-])C(F)(F)F  \n",
       "48534  NC(N)=[NH2+].O=S(=O)([O-])C(F)(F)F  \n",
       "50285  NC(N)=[NH2+].O=S(=O)([O-])C(F)(F)F  \n",
       "52324  NC(N)=[NH2+].O=S(=O)([O-])C(F)(F)F  "
      ]
     },
     "execution_count": 15,
     "metadata": {},
     "output_type": "execute_result"
    }
   ],
   "source": [
    "sub = df.loc[df.cmp1_id.isin(cmps.id) | df.cmp2_id.isin(cmps.id) | df.cmp3_id.isin(cmps.id)]\n",
    "sub"
   ]
  },
  {
   "cell_type": "markdown",
   "id": "3fbd37f4",
   "metadata": {},
   "source": [
    "#### Resonance"
   ]
  },
  {
   "cell_type": "markdown",
   "id": "70324663",
   "metadata": {},
   "source": [
    "Sometimes, substructure search will not work as expected unless resonance was considered. This can be demonstrated on non-symmetrical imidazolium cations:"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 16,
   "id": "8f656185",
   "metadata": {},
   "outputs": [
    {
     "data": {
      "image/png": "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",
      "text/plain": [
       "<rdkit.Chem.rdchem.Mol at 0x2c7974ff840>"
      ]
     },
     "execution_count": 16,
     "metadata": {},
     "output_type": "execute_result"
    }
   ],
   "source": [
    "mol1 = Chem.MolFromSmiles('C[n+]1cc[n](CC)c1')\n",
    "mol2 = Chem.MolFromSmiles('C[n]1cc[n+](CC)c1')\n",
    "mol1"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 17,
   "id": "b120a4e7",
   "metadata": {},
   "outputs": [
    {
     "data": {
      "image/png": "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",
      "text/plain": [
       "<rdkit.Chem.rdchem.Mol at 0x2c7974ffd80>"
      ]
     },
     "execution_count": 17,
     "metadata": {},
     "output_type": "execute_result"
    }
   ],
   "source": [
    "mol2"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 18,
   "id": "057d7a33",
   "metadata": {},
   "outputs": [
    {
     "data": {
      "text/plain": [
       "False"
      ]
     },
     "execution_count": 18,
     "metadata": {},
     "output_type": "execute_result"
    }
   ],
   "source": [
    "mol1.HasSubstructMatch(mol2)"
   ]
  },
  {
   "cell_type": "markdown",
   "id": "e7d146ca",
   "metadata": {},
   "source": [
    "Despite the fact that both molecules are equivalent, their graph representation is not, and current SMILES normalization (as implemented in RDKit) does not change that:"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 19,
   "id": "a7e380ec",
   "metadata": {},
   "outputs": [
    {
     "data": {
      "text/plain": [
       "('CCn1cc[n+](C)c1', 'CC[n+]1ccn(C)c1')"
      ]
     },
     "execution_count": 19,
     "metadata": {},
     "output_type": "execute_result"
    }
   ],
   "source": [
    "Chem.MolToSmiles(mol1), Chem.MolToSmiles(mol2)"
   ]
  },
  {
   "cell_type": "markdown",
   "id": "c5f3eafb",
   "metadata": {},
   "source": [
    "This problem can be adressed in two ways:\n",
    "\n",
    "1. choosing SMARTS for the substructure search more accurately, e.g. ignoring atomic charges (see Daylight manuals on SMARTS for some ideas: [1](https://www.daylight.com/dayhtml/doc/theory/theory.smarts.html), [2](https://www.daylight.com/dayhtml_tutorials/languages/smarts/smarts_examples.html));\n",
    "\n",
    "2. considering resonance via `ResonanceMolSupplier` class."
   ]
  }
 ],
 "metadata": {
  "kernelspec": {
   "display_name": "Python 3 (ipykernel)",
   "language": "python",
   "name": "python3"
  },
  "language_info": {
   "codemirror_mode": {
    "name": "ipython",
    "version": 3
   },
   "file_extension": ".py",
   "mimetype": "text/x-python",
   "name": "python",
   "nbconvert_exporter": "python",
   "pygments_lexer": "ipython3",
   "version": "3.10.14"
  }
 },
 "nbformat": 4,
 "nbformat_minor": 5
}