ro2_qooh_5memring.ipynb

{
 "cells": [
  {
   "cell_type": "code",
   "execution_count": 1,
   "metadata": {},
   "outputs": [],
   "source": [
    "from rdkit.Chem import AllChem\n",
    "from rdkit.Chem import rdChemReactions\n",
    "from rdkit import Chem\n",
    "from rdkit.Chem import Draw, AllChem\n",
    "from rdkit.Chem.Descriptors import NumRadicalElectrons\n",
    "from IPython.display import Image, display\n",
    "from enum_rxns import *"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 2,
   "metadata": {
    "scrolled": true
   },
   "outputs": [],
   "source": [
    "import pandas as pd\n",
    "rxn_sma = '[O:1]-[O:2]-[C:3]-[C:4]-[H:5]>>[H:5]-[O:1]-[O:2]-[C:3]-[C:4]'\n",
    "reactants = [['[O]OC(OC)C'],['[O]OCCOC'], #methoxy, no methyl\n",
    "             ['[O]OC(C)(OC)C'],['[O]OCC(C)OC'], #methoxy, one methyl, at same carbon\n",
    "             ['[O]OC(CC)OC'],['[O]OC(C)COC'], #methoxy, one methyl, at different carbons\n",
    "             ['[O]OC(OC)(C)CC'],['[O]OC(OC)C(C)C'], \n",
    "             ['[O]OC(C)C(C)OC'],['[O]OC(C)(C)COC'], #methoxy, two methyls\n",
    "             ['[O]OC(C)(OC)C(C)C'],['[O]OC(C)(C)C(C)OC']] #methoxy, three methyls\n",
    "\n",
    "Images = []\n",
    "rxn_smiles_all = []\n",
    "rxn_types_all = []\n",
    "for i, reactant in enumerate(reactants):\n",
    "    possible_products = run_rxn(rxn_sma, reactant)\n",
    "    #print(possible_products)\n",
    "\n",
    "    for j, prod in enumerate(possible_products):\n",
    "        rxn_smiles = '.'.join(reactant)+'>>'+'.'.join(prod)\n",
    "        rxn_type = get_rxn_type(rxn_smiles)\n",
    "        #print(rxn_smiles, rxn_type)\n",
    "        rxn_smiles_all.append(rxn_smiles)\n",
    "        rxn_types_all.append(rxn_type)\n",
    "        #png = visualize_rxn(rxn_smiles, 'test'+str(i)+str(j)+'.png')\n",
    "        #Images.append(Image(filename = 'test'+str(i)+str(j)+'.png'))\n",
    "        #IPython.display.Image(png)\n",
    "        \n",
    "df = pd.DataFrame(list(map(list, zip(*[rxn_smiles_all, rxn_types_all]))), columns = ['rxn_smiles', 'rxn_type'])\n",
    "df['R'] = [ x.split('>>')[0] for x in df.rxn_smiles]\n",
    "df['P'] = [ x.split('>>')[1] for x in df.rxn_smiles]\n",
    "df['rxn_type'] += '_5mem'"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 3,
   "metadata": {},
   "outputs": [
    {
     "data": {
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       "    }\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>rxn_smiles</th>\n",
       "      <th>rxn_type</th>\n",
       "      <th>R</th>\n",
       "      <th>P</th>\n",
       "    </tr>\n",
       "  </thead>\n",
       "  <tbody>\n",
       "    <tr>\n",
       "      <th>0</th>\n",
       "      <td>[O]OC(OC)C&gt;&gt;[CH2]C(OC)OO</td>\n",
       "      <td>2a-1_5mem</td>\n",
       "      <td>[O]OC(OC)C</td>\n",
       "      <td>[CH2]C(OC)OO</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>1</th>\n",
       "      <td>[O]OCCOC&gt;&gt;CO[CH]COO</td>\n",
       "      <td>1-2a_5mem</td>\n",
       "      <td>[O]OCCOC</td>\n",
       "      <td>CO[CH]COO</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>2</th>\n",
       "      <td>[O]OC(C)(OC)C&gt;&gt;[CH2]C(C)(OC)OO</td>\n",
       "      <td>3a-1_5mem</td>\n",
       "      <td>[O]OC(C)(OC)C</td>\n",
       "      <td>[CH2]C(C)(OC)OO</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>3</th>\n",
       "      <td>[O]OCC(C)OC&gt;&gt;CO[C](C)COO</td>\n",
       "      <td>1-3a_5mem</td>\n",
       "      <td>[O]OCC(C)OC</td>\n",
       "      <td>CO[C](C)COO</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>4</th>\n",
       "      <td>[O]OC(CC)OC&gt;&gt;C[CH]C(OC)OO</td>\n",
       "      <td>2a-2_5mem</td>\n",
       "      <td>[O]OC(CC)OC</td>\n",
       "      <td>C[CH]C(OC)OO</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>5</th>\n",
       "      <td>[O]OC(C)COC&gt;&gt;CO[CH]C(C)OO</td>\n",
       "      <td>2-2a_5mem</td>\n",
       "      <td>[O]OC(C)COC</td>\n",
       "      <td>CO[CH]C(C)OO</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>6</th>\n",
       "      <td>[O]OC(C)COC&gt;&gt;[CH2]C(COC)OO</td>\n",
       "      <td>2-1_5mem</td>\n",
       "      <td>[O]OC(C)COC</td>\n",
       "      <td>[CH2]C(COC)OO</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>7</th>\n",
       "      <td>[O]OC(OC)(C)CC&gt;&gt;C[CH]C(C)(OC)OO</td>\n",
       "      <td>3a-2_5mem</td>\n",
       "      <td>[O]OC(OC)(C)CC</td>\n",
       "      <td>C[CH]C(C)(OC)OO</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>8</th>\n",
       "      <td>[O]OC(OC)(C)CC&gt;&gt;[CH2]C(CC)(OC)OO</td>\n",
       "      <td>3a-1_5mem</td>\n",
       "      <td>[O]OC(OC)(C)CC</td>\n",
       "      <td>[CH2]C(CC)(OC)OO</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>9</th>\n",
       "      <td>[O]OC(OC)C(C)C&gt;&gt;COC(OO)[C](C)C</td>\n",
       "      <td>2a-3_5mem</td>\n",
       "      <td>[O]OC(OC)C(C)C</td>\n",
       "      <td>COC(OO)[C](C)C</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>10</th>\n",
       "      <td>[O]OC(C)C(C)OC&gt;&gt;[CH2]C(OO)C(C)OC</td>\n",
       "      <td>2-1_5mem</td>\n",
       "      <td>[O]OC(C)C(C)OC</td>\n",
       "      <td>[CH2]C(OO)C(C)OC</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>11</th>\n",
       "      <td>[O]OC(C)C(C)OC&gt;&gt;CO[C](C)C(C)OO</td>\n",
       "      <td>2-3a_5mem</td>\n",
       "      <td>[O]OC(C)C(C)OC</td>\n",
       "      <td>CO[C](C)C(C)OO</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>12</th>\n",
       "      <td>[O]OC(C)(C)COC&gt;&gt;CO[CH]C(C)(C)OO</td>\n",
       "      <td>3-2a_5mem</td>\n",
       "      <td>[O]OC(C)(C)COC</td>\n",
       "      <td>CO[CH]C(C)(C)OO</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>13</th>\n",
       "      <td>[O]OC(C)(C)COC&gt;&gt;[CH2]C(C)(COC)OO</td>\n",
       "      <td>3-1_5mem</td>\n",
       "      <td>[O]OC(C)(C)COC</td>\n",
       "      <td>[CH2]C(C)(COC)OO</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>14</th>\n",
       "      <td>[O]OC(C)(OC)C(C)C&gt;&gt;[CH2]C(OC)(OO)C(C)C</td>\n",
       "      <td>3a-1_5mem</td>\n",
       "      <td>[O]OC(C)(OC)C(C)C</td>\n",
       "      <td>[CH2]C(OC)(OO)C(C)C</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>15</th>\n",
       "      <td>[O]OC(C)(OC)C(C)C&gt;&gt;COC(C)(OO)[C](C)C</td>\n",
       "      <td>3a-3_5mem</td>\n",
       "      <td>[O]OC(C)(OC)C(C)C</td>\n",
       "      <td>COC(C)(OO)[C](C)C</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>16</th>\n",
       "      <td>[O]OC(C)(C)C(C)OC&gt;&gt;CO[C](C)C(C)(C)OO</td>\n",
       "      <td>3-3a_5mem</td>\n",
       "      <td>[O]OC(C)(C)C(C)OC</td>\n",
       "      <td>CO[C](C)C(C)(C)OO</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>17</th>\n",
       "      <td>[O]OC(C)(C)C(C)OC&gt;&gt;[CH2]C(C)(OO)C(C)OC</td>\n",
       "      <td>3-1_5mem</td>\n",
       "      <td>[O]OC(C)(C)C(C)OC</td>\n",
       "      <td>[CH2]C(C)(OO)C(C)OC</td>\n",
       "    </tr>\n",
       "  </tbody>\n",
       "</table>\n",
       "</div>"
      ],
      "text/plain": [
       "                                rxn_smiles   rxn_type                  R  \\\n",
       "0                 [O]OC(OC)C>>[CH2]C(OC)OO  2a-1_5mem         [O]OC(OC)C   \n",
       "1                      [O]OCCOC>>CO[CH]COO  1-2a_5mem           [O]OCCOC   \n",
       "2           [O]OC(C)(OC)C>>[CH2]C(C)(OC)OO  3a-1_5mem      [O]OC(C)(OC)C   \n",
       "3                 [O]OCC(C)OC>>CO[C](C)COO  1-3a_5mem        [O]OCC(C)OC   \n",
       "4                [O]OC(CC)OC>>C[CH]C(OC)OO  2a-2_5mem        [O]OC(CC)OC   \n",
       "5                [O]OC(C)COC>>CO[CH]C(C)OO  2-2a_5mem        [O]OC(C)COC   \n",
       "6               [O]OC(C)COC>>[CH2]C(COC)OO   2-1_5mem        [O]OC(C)COC   \n",
       "7          [O]OC(OC)(C)CC>>C[CH]C(C)(OC)OO  3a-2_5mem     [O]OC(OC)(C)CC   \n",
       "8         [O]OC(OC)(C)CC>>[CH2]C(CC)(OC)OO  3a-1_5mem     [O]OC(OC)(C)CC   \n",
       "9           [O]OC(OC)C(C)C>>COC(OO)[C](C)C  2a-3_5mem     [O]OC(OC)C(C)C   \n",
       "10        [O]OC(C)C(C)OC>>[CH2]C(OO)C(C)OC   2-1_5mem     [O]OC(C)C(C)OC   \n",
       "11          [O]OC(C)C(C)OC>>CO[C](C)C(C)OO  2-3a_5mem     [O]OC(C)C(C)OC   \n",
       "12         [O]OC(C)(C)COC>>CO[CH]C(C)(C)OO  3-2a_5mem     [O]OC(C)(C)COC   \n",
       "13        [O]OC(C)(C)COC>>[CH2]C(C)(COC)OO   3-1_5mem     [O]OC(C)(C)COC   \n",
       "14  [O]OC(C)(OC)C(C)C>>[CH2]C(OC)(OO)C(C)C  3a-1_5mem  [O]OC(C)(OC)C(C)C   \n",
       "15    [O]OC(C)(OC)C(C)C>>COC(C)(OO)[C](C)C  3a-3_5mem  [O]OC(C)(OC)C(C)C   \n",
       "16    [O]OC(C)(C)C(C)OC>>CO[C](C)C(C)(C)OO  3-3a_5mem  [O]OC(C)(C)C(C)OC   \n",
       "17  [O]OC(C)(C)C(C)OC>>[CH2]C(C)(OO)C(C)OC   3-1_5mem  [O]OC(C)(C)C(C)OC   \n",
       "\n",
       "                      P  \n",
       "0          [CH2]C(OC)OO  \n",
       "1             CO[CH]COO  \n",
       "2       [CH2]C(C)(OC)OO  \n",
       "3           CO[C](C)COO  \n",
       "4          C[CH]C(OC)OO  \n",
       "5          CO[CH]C(C)OO  \n",
       "6         [CH2]C(COC)OO  \n",
       "7       C[CH]C(C)(OC)OO  \n",
       "8      [CH2]C(CC)(OC)OO  \n",
       "9        COC(OO)[C](C)C  \n",
       "10     [CH2]C(OO)C(C)OC  \n",
       "11       CO[C](C)C(C)OO  \n",
       "12      CO[CH]C(C)(C)OO  \n",
       "13     [CH2]C(C)(COC)OO  \n",
       "14  [CH2]C(OC)(OO)C(C)C  \n",
       "15    COC(C)(OO)[C](C)C  \n",
       "16    CO[C](C)C(C)(C)OO  \n",
       "17  [CH2]C(C)(OO)C(C)OC  "
      ]
     },
     "execution_count": 3,
     "metadata": {},
     "output_type": "execute_result"
    }
   ],
   "source": [
    "df"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 4,
   "metadata": {},
   "outputs": [
    {
     "name": "stdout",
     "output_type": "stream",
     "text": [
      "Counter({'3a-1': 3, '2-1': 2, '3-1': 2, '2a-1': 1, '1-2a': 1, '1-3a': 1, '2a-2': 1, '2-2a': 1, '3a-2': 1, '2a-3': 1, '2-3a': 1, '3-2a': 1, '3a-3': 1, '3-3a': 1})\n",
      "Counter({'[O]OC(C)COC': 2, '[O]OC(OC)(C)CC': 2, '[O]OC(C)C(C)OC': 2, '[O]OC(C)(C)COC': 2, '[O]OC(C)(OC)C(C)C': 2, '[O]OC(C)(C)C(C)OC': 2, '[O]OC(OC)C': 1, '[O]OCCOC': 1, '[O]OC(C)(OC)C': 1, '[O]OCC(C)OC': 1, '[O]OC(CC)OC': 1, '[O]OC(OC)C(C)C': 1})\n",
      "14\n",
      "18\n",
      "0\n"
     ]
    }
   ],
   "source": [
    "from collections import Counter\n",
    "rxn_type_counter = Counter(rxn_types_all)\n",
    "reactant_counter = Counter([x.split('>>')[0] for x in rxn_smiles_all])\n",
    "print(rxn_type_counter)\n",
    "print(reactant_counter)\n",
    "print(len(Counter(rxn_types_all).keys()))\n",
    "print(len(rxn_smiles_all))\n",
    "# Sometimes >1 reactions are generated per each rxn_type from run_rxn \n",
    "#due to some unexpected hydrogen transfers from methyl substituents\n",
    "isDel = []\n",
    "for _, row in df.iterrows():\n",
    "    if rxn_type_counter[row['rxn_type']] > 1 and reactant_counter[row['rxn_smiles'].split('>>')[0]] > 1:\n",
    "        isDel.append(True)\n",
    "    else:\n",
    "        isDel.append(False)\n",
    "print(isDel.count(True))\n",
    "df['isDel'] = isDel"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 5,
   "metadata": {},
   "outputs": [],
   "source": [
    "#display(*Images)"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 6,
   "metadata": {},
   "outputs": [
    {
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       "<table border=\"1\" class=\"dataframe\">\n",
       "  <thead>\n",
       "    <tr style=\"text-align: right;\">\n",
       "      <th></th>\n",
       "      <th>rxn_smiles</th>\n",
       "      <th>rxn_type</th>\n",
       "      <th>R</th>\n",
       "      <th>P</th>\n",
       "      <th>isDel</th>\n",
       "    </tr>\n",
       "  </thead>\n",
       "  <tbody>\n",
       "    <tr>\n",
       "      <th>0</th>\n",
       "      <td>[O]OC(OC)C&gt;&gt;[CH2]C(OC)OO</td>\n",
       "      <td>2a-1_5mem</td>\n",
       "      <td>[O]OC(OC)C</td>\n",
       "      <td>[CH2]C(OC)OO</td>\n",
       "      <td>False</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>1</th>\n",
       "      <td>[O]OCCOC&gt;&gt;CO[CH]COO</td>\n",
       "      <td>1-2a_5mem</td>\n",
       "      <td>[O]OCCOC</td>\n",
       "      <td>CO[CH]COO</td>\n",
       "      <td>False</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>2</th>\n",
       "      <td>[O]OC(C)(OC)C&gt;&gt;[CH2]C(C)(OC)OO</td>\n",
       "      <td>3a-1_5mem</td>\n",
       "      <td>[O]OC(C)(OC)C</td>\n",
       "      <td>[CH2]C(C)(OC)OO</td>\n",
       "      <td>False</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>3</th>\n",
       "      <td>[O]OCC(C)OC&gt;&gt;CO[C](C)COO</td>\n",
       "      <td>1-3a_5mem</td>\n",
       "      <td>[O]OCC(C)OC</td>\n",
       "      <td>CO[C](C)COO</td>\n",
       "      <td>False</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>4</th>\n",
       "      <td>[O]OC(CC)OC&gt;&gt;C[CH]C(OC)OO</td>\n",
       "      <td>2a-2_5mem</td>\n",
       "      <td>[O]OC(CC)OC</td>\n",
       "      <td>C[CH]C(OC)OO</td>\n",
       "      <td>False</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>5</th>\n",
       "      <td>[O]OC(C)COC&gt;&gt;CO[CH]C(C)OO</td>\n",
       "      <td>2-2a_5mem</td>\n",
       "      <td>[O]OC(C)COC</td>\n",
       "      <td>CO[CH]C(C)OO</td>\n",
       "      <td>False</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>6</th>\n",
       "      <td>[O]OC(C)COC&gt;&gt;[CH2]C(COC)OO</td>\n",
       "      <td>2-1_5mem</td>\n",
       "      <td>[O]OC(C)COC</td>\n",
       "      <td>[CH2]C(COC)OO</td>\n",
       "      <td>False</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>7</th>\n",
       "      <td>[O]OC(OC)(C)CC&gt;&gt;C[CH]C(C)(OC)OO</td>\n",
       "      <td>3a-2_5mem</td>\n",
       "      <td>[O]OC(OC)(C)CC</td>\n",
       "      <td>C[CH]C(C)(OC)OO</td>\n",
       "      <td>False</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>8</th>\n",
       "      <td>[O]OC(OC)(C)CC&gt;&gt;[CH2]C(CC)(OC)OO</td>\n",
       "      <td>3a-1_5mem</td>\n",
       "      <td>[O]OC(OC)(C)CC</td>\n",
       "      <td>[CH2]C(CC)(OC)OO</td>\n",
       "      <td>False</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>9</th>\n",
       "      <td>[O]OC(OC)C(C)C&gt;&gt;COC(OO)[C](C)C</td>\n",
       "      <td>2a-3_5mem</td>\n",
       "      <td>[O]OC(OC)C(C)C</td>\n",
       "      <td>COC(OO)[C](C)C</td>\n",
       "      <td>False</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>10</th>\n",
       "      <td>[O]OC(C)C(C)OC&gt;&gt;[CH2]C(OO)C(C)OC</td>\n",
       "      <td>2-1_5mem</td>\n",
       "      <td>[O]OC(C)C(C)OC</td>\n",
       "      <td>[CH2]C(OO)C(C)OC</td>\n",
       "      <td>False</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>11</th>\n",
       "      <td>[O]OC(C)C(C)OC&gt;&gt;CO[C](C)C(C)OO</td>\n",
       "      <td>2-3a_5mem</td>\n",
       "      <td>[O]OC(C)C(C)OC</td>\n",
       "      <td>CO[C](C)C(C)OO</td>\n",
       "      <td>False</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>12</th>\n",
       "      <td>[O]OC(C)(C)COC&gt;&gt;CO[CH]C(C)(C)OO</td>\n",
       "      <td>3-2a_5mem</td>\n",
       "      <td>[O]OC(C)(C)COC</td>\n",
       "      <td>CO[CH]C(C)(C)OO</td>\n",
       "      <td>False</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>13</th>\n",
       "      <td>[O]OC(C)(C)COC&gt;&gt;[CH2]C(C)(COC)OO</td>\n",
       "      <td>3-1_5mem</td>\n",
       "      <td>[O]OC(C)(C)COC</td>\n",
       "      <td>[CH2]C(C)(COC)OO</td>\n",
       "      <td>False</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>14</th>\n",
       "      <td>[O]OC(C)(OC)C(C)C&gt;&gt;[CH2]C(OC)(OO)C(C)C</td>\n",
       "      <td>3a-1_5mem</td>\n",
       "      <td>[O]OC(C)(OC)C(C)C</td>\n",
       "      <td>[CH2]C(OC)(OO)C(C)C</td>\n",
       "      <td>False</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>15</th>\n",
       "      <td>[O]OC(C)(OC)C(C)C&gt;&gt;COC(C)(OO)[C](C)C</td>\n",
       "      <td>3a-3_5mem</td>\n",
       "      <td>[O]OC(C)(OC)C(C)C</td>\n",
       "      <td>COC(C)(OO)[C](C)C</td>\n",
       "      <td>False</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>16</th>\n",
       "      <td>[O]OC(C)(C)C(C)OC&gt;&gt;CO[C](C)C(C)(C)OO</td>\n",
       "      <td>3-3a_5mem</td>\n",
       "      <td>[O]OC(C)(C)C(C)OC</td>\n",
       "      <td>CO[C](C)C(C)(C)OO</td>\n",
       "      <td>False</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>17</th>\n",
       "      <td>[O]OC(C)(C)C(C)OC&gt;&gt;[CH2]C(C)(OO)C(C)OC</td>\n",
       "      <td>3-1_5mem</td>\n",
       "      <td>[O]OC(C)(C)C(C)OC</td>\n",
       "      <td>[CH2]C(C)(OO)C(C)OC</td>\n",
       "      <td>False</td>\n",
       "    </tr>\n",
       "  </tbody>\n",
       "</table>\n",
       "</div>"
      ],
      "text/plain": [
       "                                rxn_smiles   rxn_type                  R  \\\n",
       "0                 [O]OC(OC)C>>[CH2]C(OC)OO  2a-1_5mem         [O]OC(OC)C   \n",
       "1                      [O]OCCOC>>CO[CH]COO  1-2a_5mem           [O]OCCOC   \n",
       "2           [O]OC(C)(OC)C>>[CH2]C(C)(OC)OO  3a-1_5mem      [O]OC(C)(OC)C   \n",
       "3                 [O]OCC(C)OC>>CO[C](C)COO  1-3a_5mem        [O]OCC(C)OC   \n",
       "4                [O]OC(CC)OC>>C[CH]C(OC)OO  2a-2_5mem        [O]OC(CC)OC   \n",
       "5                [O]OC(C)COC>>CO[CH]C(C)OO  2-2a_5mem        [O]OC(C)COC   \n",
       "6               [O]OC(C)COC>>[CH2]C(COC)OO   2-1_5mem        [O]OC(C)COC   \n",
       "7          [O]OC(OC)(C)CC>>C[CH]C(C)(OC)OO  3a-2_5mem     [O]OC(OC)(C)CC   \n",
       "8         [O]OC(OC)(C)CC>>[CH2]C(CC)(OC)OO  3a-1_5mem     [O]OC(OC)(C)CC   \n",
       "9           [O]OC(OC)C(C)C>>COC(OO)[C](C)C  2a-3_5mem     [O]OC(OC)C(C)C   \n",
       "10        [O]OC(C)C(C)OC>>[CH2]C(OO)C(C)OC   2-1_5mem     [O]OC(C)C(C)OC   \n",
       "11          [O]OC(C)C(C)OC>>CO[C](C)C(C)OO  2-3a_5mem     [O]OC(C)C(C)OC   \n",
       "12         [O]OC(C)(C)COC>>CO[CH]C(C)(C)OO  3-2a_5mem     [O]OC(C)(C)COC   \n",
       "13        [O]OC(C)(C)COC>>[CH2]C(C)(COC)OO   3-1_5mem     [O]OC(C)(C)COC   \n",
       "14  [O]OC(C)(OC)C(C)C>>[CH2]C(OC)(OO)C(C)C  3a-1_5mem  [O]OC(C)(OC)C(C)C   \n",
       "15    [O]OC(C)(OC)C(C)C>>COC(C)(OO)[C](C)C  3a-3_5mem  [O]OC(C)(OC)C(C)C   \n",
       "16    [O]OC(C)(C)C(C)OC>>CO[C](C)C(C)(C)OO  3-3a_5mem  [O]OC(C)(C)C(C)OC   \n",
       "17  [O]OC(C)(C)C(C)OC>>[CH2]C(C)(OO)C(C)OC   3-1_5mem  [O]OC(C)(C)C(C)OC   \n",
       "\n",
       "                      P  isDel  \n",
       "0          [CH2]C(OC)OO  False  \n",
       "1             CO[CH]COO  False  \n",
       "2       [CH2]C(C)(OC)OO  False  \n",
       "3           CO[C](C)COO  False  \n",
       "4          C[CH]C(OC)OO  False  \n",
       "5          CO[CH]C(C)OO  False  \n",
       "6         [CH2]C(COC)OO  False  \n",
       "7       C[CH]C(C)(OC)OO  False  \n",
       "8      [CH2]C(CC)(OC)OO  False  \n",
       "9        COC(OO)[C](C)C  False  \n",
       "10     [CH2]C(OO)C(C)OC  False  \n",
       "11       CO[C](C)C(C)OO  False  \n",
       "12      CO[CH]C(C)(C)OO  False  \n",
       "13     [CH2]C(C)(COC)OO  False  \n",
       "14  [CH2]C(OC)(OO)C(C)C  False  \n",
       "15    COC(C)(OO)[C](C)C  False  \n",
       "16    CO[C](C)C(C)(C)OO  False  \n",
       "17  [CH2]C(C)(OO)C(C)OC  False  "
      ]
     },
     "execution_count": 6,
     "metadata": {},
     "output_type": "execute_result"
    }
   ],
   "source": [
    "df[~df.isDel]"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 7,
   "metadata": {},
   "outputs": [
    {
     "data": {
      "text/plain": [
       "14"
      ]
     },
     "execution_count": 7,
     "metadata": {},
     "output_type": "execute_result"
    }
   ],
   "source": [
    "len(df[~df.isDel].rxn_type.unique())"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 8,
   "metadata": {},
   "outputs": [],
   "source": [
    "df[~df.isDel].to_csv('ro2_qooh_5mem.csv', index = False)"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 9,
   "metadata": {},
   "outputs": [
    {
     "data": {
      "text/plain": [
       "'[O]OC(OC)C.[O]OCCOC.[O]OC(C)(OC)C.[O]OCC(C)OC.[O]OC(CC)OC.[O]OC(C)COC.[O]OC(OC)(C)CC.[O]OC(OC)C(C)C.[O]OC(C)C(C)OC.[O]OC(C)(C)COC.[O]OC(C)(OC)C(C)C.[O]OC(C)(C)C(C)OC'"
      ]
     },
     "execution_count": 9,
     "metadata": {},
     "output_type": "execute_result"
    }
   ],
   "source": [
    "reactants = [['[O]OC(OC)C'],['[O]OCCOC'], #methoxy, no methyl\n",
    "             ['[O]OC(C)(OC)C'],['[O]OCC(C)OC'], #methoxy, one methyl, at same carbon\n",
    "             ['[O]OC(CC)OC'],['[O]OC(C)COC'], #methoxy, one methyl, at different carbons\n",
    "             ['[O]OC(OC)(C)CC'],['[O]OC(OC)C(C)C'], \n",
    "             ['[O]OC(C)C(C)OC'],['[O]OC(C)(C)COC'], #methoxy, two methyls\n",
    "             ['[O]OC(C)(OC)C(C)C'],['[O]OC(C)(C)C(C)OC']]\n",
    "reactants = [x[0] for x in reactants]\n",
    "'.'.join(reactants)"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": null,
   "metadata": {},
   "outputs": [],
   "source": []
  }
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