Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
C#Cc1cc(OCc2c(F)cccc2F)c2nc(C)c(C(=O)O)n2c1
InChiKey
CPIRWXMFXDDKQI-UHFFFAOYSA-N
Route Signature
e93748ece60791c092788b5cd3990f4e351d0c00431438c8724e28838335e85c
Synthesis route with 6 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_9f64e156f8ee4fa671ec36a6",
"signature": "e93748ece60791c092788b5cd3990f4e351d0c00431438c8724e28838335e85c",
"contentHash": "dcca0676e9af0a964be2a505057126fd83ee931c32bb3de73d0764785f5e3837",
"length": 6,
"isConvergent": false
},
"target": {
"id": "sa_489fd3822b2edc95c1c43729",
"benchmarkSetId": "61e696668b63e77d7c2a29c0821768e1c383de8313852d6e995224859494442e",
"targetId": "n5-00342",
"moleculeId": "sa_4f8342bf4b667d18c04b60c6",
"smiles": "C#Cc1cc(OCc2c(F)cccc2F)c2nc(C)c(C(=O)O)n2c1",
"routeLength": 6,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_4f8342bf4b667d18c04b60c6",
"inchikey": "CPIRWXMFXDDKQI-UHFFFAOYSA-N",
"smiles": "C#Cc1cc(OCc2c(F)cccc2F)c2nc(C)c(C(=O)O)n2c1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "13114",
"routeId": "sa_9f64e156f8ee4fa671ec36a6",
"moleculeId": "sa_4f8342bf4b667d18c04b60c6",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_4f8342bf4b667d18c04b60c6",
"inchikey": "CPIRWXMFXDDKQI-UHFFFAOYSA-N",
"smiles": "C#Cc1cc(OCc2c(F)cccc2F)c2nc(C)c(C(=O)O)n2c1"
},
"smiles": "C#Cc1cc(OCc2c(F)cccc2F)c2nc(C)c(C(=O)O)n2c1",
"reactionStepId": "sa_5d4d8a3123d7d656a0e0783b",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140128386A1;1171;1522921\",\"rsmi\":\"CC[O:13][C:11]([c:10]1[n:5]2[cH:4][c:3]([C:2]#[CH:1])[cH:25][c:14]([O:15][CH2:16][c:17]3[c:18]([F:19])[cH:20][cH:21][cH:22][c:23]3[F:24])[c:6]2[n:7][c:8]1[CH3:9])=[O:12]>C1CCOC1.CO.Cl.[Li+].O>[CH:1]#[C:2][c:3]1[cH:4][n:5]2[c:6]([n:7][c:8]([CH3:9])[c:10]2[C:11](=[O:12])[OH:13])[c:14]([O:15][CH2:16][c:17]2[c:18]([F:19])[cH:20][cH:21][cH:22][c:23]2[F:24])[cH:25]1\"},\"mapped_reaction_smiles\":\"CC[O:13][C:11]([c:10]1[n:5]2[cH:4][c:3]([C:2]#[CH:1])[cH:25][c:14]([O:15][CH2:16][c:17]3[c:18]([F:19])[cH:20][cH:21][cH:22][c:23]3[F:24])[c:6]2[n:7][c:8]1[CH3:9])=[O:12]>C1CCOC1.CO.Cl.[Li+].O>[CH:1]#[C:2][c:3]1[cH:4][n:5]2[c:6]([n:7][c:8]([CH3:9])[c:10]2[C:11](=[O:12])[OH:13])[c:14]([O:15][CH2:16][c:17]2[c:18]([F:19])[cH:20][cH:21][cH:22][c:23]2[F:24])[cH:25]1\"}",
"reactionStep": {
"id": "sa_5d4d8a3123d7d656a0e0783b",
"reactionHash": "f33ba8db63af05079d831f144fd18331d5e6d7dd133a9df183c5be9581da565b"
},
"children": [
{
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"routeId": "sa_9f64e156f8ee4fa671ec36a6",
"moleculeId": "sa_3ba344d336665a9f9d6ebf7c",
"parentId": "13114",
"isLeaf": false,
"molecule": {
"id": "sa_3ba344d336665a9f9d6ebf7c",
"inchikey": "NDFMFIMPZHEQCY-UHFFFAOYSA-N",
"smiles": "C#Cc1cc(OCc2c(F)cccc2F)c2nc(C)c(C(=O)OCC)n2c1"
},
"smiles": "C#Cc1cc(OCc2c(F)cccc2F)c2nc(C)c(C(=O)OCC)n2c1",
"reactionStepId": "sa_1f993afea6c44ba1dac1643d",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140128386A1;1166;1522920\",\"rsmi\":\"C[Si](C)(C)[C:1]#[C:2][c:3]1[cH:4][n:5]2[c:6]([n:7][c:8]([CH3:9])[c:10]2[C:11](=[O:12])[O:13][CH2:14][CH3:15])[c:16]([O:17][CH2:18][c:19]2[c:20]([F:21])[cH:22][cH:23][cH:24][c:25]2[F:26])[cH:27]1>CO.O=C(O)O.[K+].[K+]>[CH:1]#[C:2][c:3]1[cH:4][n:5]2[c:6]([n:7][c:8]([CH3:9])[c:10]2[C:11](=[O:12])[O:13][CH2:14][CH3:15])[c:16]([O:17][CH2:18][c:19]2[c:20]([F:21])[cH:22][cH:23][cH:24][c:25]2[F:26])[cH:27]1\"},\"mapped_reaction_smiles\":\"C[Si](C)(C)[C:1]#[C:2][c:3]1[cH:4][n:5]2[c:6]([n:7][c:8]([CH3:9])[c:10]2[C:11](=[O:12])[O:13][CH2:14][CH3:15])[c:16]([O:17][CH2:18][c:19]2[c:20]([F:21])[cH:22][cH:23][cH:24][c:25]2[F:26])[cH:27]1>CO.O=C(O)O.[K+].[K+]>[CH:1]#[C:2][c:3]1[cH:4][n:5]2[c:6]([n:7][c:8]([CH3:9])[c:10]2[C:11](=[O:12])[O:13][CH2:14][CH3:15])[c:16]([O:17][CH2:18][c:19]2[c:20]([F:21])[cH:22][cH:23][cH:24][c:25]2[F:26])[cH:27]1\"}",
"reactionStep": {
"id": "sa_1f993afea6c44ba1dac1643d",
"reactionHash": "136012b3ffcfbf8298d88061b1a96ffd60674a228648459278df62f391a0a8c5"
},
"children": [
{
"id": "13116",
"routeId": "sa_9f64e156f8ee4fa671ec36a6",
"moleculeId": "sa_38dd30eecdc645c1c6edeb6a",
"parentId": "13115",
"isLeaf": false,
"molecule": {
"id": "sa_38dd30eecdc645c1c6edeb6a",
"inchikey": "ZRYOENLXHLVPHN-UHFFFAOYSA-N",
"smiles": "CCOC(=O)c1c(C)nc2c(OCc3c(F)cccc3F)cc(C#C[Si](C)(C)C)cn12"
},
"smiles": "CCOC(=O)c1c(C)nc2c(OCc3c(F)cccc3F)cc(C#C[Si](C)(C)C)cn12",
"reactionStepId": "sa_59ff7199918d4c5082ed274a",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140128386A1;1161;1522919\",\"rsmi\":\"Br[c:23]1[cH:22][c:11]([O:12][CH2:13][c:14]2[c:15]([F:16])[cH:17][cH:18][cH:19][c:20]2[F:21])[c:10]2[n:9][c:7]([CH3:8])[c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[n:31]2[cH:30]1.[CH:24]#[C:25][Si:26]([CH3:27])([CH3:28])[CH3:29]>C1COCCO1.CCN(C(C)C)C(C)C.Cl[Pd](Cl)([PH](c1ccccc1)(c1ccccc1)c1ccccc1)[PH](c1ccccc1)(c1ccccc1)c1ccccc1.[Cu]I>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7]([CH3:8])[n:9][c:10]2[c:11]([O:12][CH2:13][c:14]3[c:15]([F:16])[cH:17][cH:18][cH:19][c:20]3[F:21])[cH:22][c:23]([C:24]#[C:25][Si:26]([CH3:27])([CH3:28])[CH3:29])[cH:30][n:31]12\"},\"mapped_reaction_smiles\":\"Br[c:23]1[cH:22][c:11]([O:12][CH2:13][c:14]2[c:15]([F:16])[cH:17][cH:18][cH:19][c:20]2[F:21])[c:10]2[n:9][c:7]([CH3:8])[c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[n:31]2[cH:30]1.[CH:24]#[C:25][Si:26]([CH3:27])([CH3:28])[CH3:29]>C1COCCO1.CCN(C(C)C)C(C)C.Cl[Pd](Cl)([PH](c1ccccc1)(c1ccccc1)c1ccccc1)[PH](c1ccccc1)(c1ccccc1)c1ccccc1.[Cu]I>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7]([CH3:8])[n:9][c:10]2[c:11]([O:12][CH2:13][c:14]3[c:15]([F:16])[cH:17][cH:18][cH:19][c:20]3[F:21])[cH:22][c:23]([C:24]#[C:25][Si:26]([CH3:27])([CH3:28])[CH3:29])[cH:30][n:31]12\"}",
"reactionStep": {
"id": "sa_59ff7199918d4c5082ed274a",
"reactionHash": "fb7695a633abd664fbf761a02afa1250266450f9fb6516cf522eba05cd37e4fc"
},
"children": [
{
"id": "13117",
"routeId": "sa_9f64e156f8ee4fa671ec36a6",
"moleculeId": "sa_95a9277ba0d873f43bb42b7f",
"parentId": "13116",
"isLeaf": true,
"molecule": {
"id": "sa_95a9277ba0d873f43bb42b7f",
"inchikey": "CWMFRHBXRUITQE-UHFFFAOYSA-N",
"smiles": "C#C[Si](C)(C)C"
},
"smiles": "C#C[Si](C)(C)C",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "13118",
"routeId": "sa_9f64e156f8ee4fa671ec36a6",
"moleculeId": "sa_fb599a77e59bb20ded1a15a1",
"parentId": "13116",
"isLeaf": false,
"molecule": {
"id": "sa_fb599a77e59bb20ded1a15a1",
"inchikey": "DNYGLKLNMOWJIK-UHFFFAOYSA-N",
"smiles": "CCOC(=O)c1c(C)nc2c(OCc3c(F)cccc3F)cc(Br)cn12"
},
"smiles": "CCOC(=O)c1c(C)nc2c(OCc3c(F)cccc3F)cc(Br)cn12",
"reactionStepId": "sa_e1a3457f4713887d5b259d56",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140128386A1;1080;1522904\",\"rsmi\":\"O=[C:7]([CH:6](Cl)[C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH3:8].[NH2:9][c:10]1[c:11]([O:12][CH2:13][c:14]2[c:15]([F:16])[cH:17][cH:18][cH:19][c:20]2[F:21])[cH:22][c:23]([Br:24])[cH:25][n:26]1>CCO>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7]([CH3:8])[n:9][c:10]2[c:11]([O:12][CH2:13][c:14]3[c:15]([F:16])[cH:17][cH:18][cH:19][c:20]3[F:21])[cH:22][c:23]([Br:24])[cH:25][n:26]12\"},\"mapped_reaction_smiles\":\"O=[C:7]([CH:6](Cl)[C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH3:8].[NH2:9][c:10]1[c:11]([O:12][CH2:13][c:14]2[c:15]([F:16])[cH:17][cH:18][cH:19][c:20]2[F:21])[cH:22][c:23]([Br:24])[cH:25][n:26]1>CCO>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7]([CH3:8])[n:9][c:10]2[c:11]([O:12][CH2:13][c:14]3[c:15]([F:16])[cH:17][cH:18][cH:19][c:20]3[F:21])[cH:22][c:23]([Br:24])[cH:25][n:26]12\"}",
"reactionStep": {
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"reactionHash": "353f6a52b1a49db67681afa7903ee0e58d16394439b5144ae9e5cdacfa452934"
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"children": [
{
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"moleculeId": "sa_ae0eb939e3b9533198f770a9",
"parentId": "13118",
"isLeaf": true,
"molecule": {
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"inchikey": "RDULEYWUGKOCMR-UHFFFAOYSA-N",
"smiles": "CCOC(=O)C(Cl)C(C)=O"
},
"smiles": "CCOC(=O)C(Cl)C(C)=O",
"reactionStepId": null,
"template": null,
"metadata": null,
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"children": []
},
{
"id": "13120",
"routeId": "sa_9f64e156f8ee4fa671ec36a6",
"moleculeId": "sa_0fa780aea5bd1ac9a73b816f",
"parentId": "13118",
"isLeaf": false,
"molecule": {
"id": "sa_0fa780aea5bd1ac9a73b816f",
"inchikey": "XPEVQMIXUMMTDD-UHFFFAOYSA-N",
"smiles": "Nc1ncc(Br)cc1OCc1c(F)cccc1F"
},
"smiles": "Nc1ncc(Br)cc1OCc1c(F)cccc1F",
"reactionStepId": "sa_79da9de95834d3b40d4b4769",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140128386A1;1076;1522903\",\"rsmi\":\"Br[Br:6].[NH2:1][c:2]1[n:3][cH:4][cH:5][cH:7][c:8]1[O:9][CH2:10][c:11]1[c:12]([F:13])[cH:14][cH:15][cH:16][c:17]1[F:18]>CC(=O)O.CCOC(C)=O.O=S(=O)(O)O>[NH2:1][c:2]1[n:3][cH:4][c:5]([Br:6])[cH:7][c:8]1[O:9][CH2:10][c:11]1[c:12]([F:13])[cH:14][cH:15][cH:16][c:17]1[F:18]\"},\"mapped_reaction_smiles\":\"Br[Br:6].[NH2:1][c:2]1[n:3][cH:4][cH:5][cH:7][c:8]1[O:9][CH2:10][c:11]1[c:12]([F:13])[cH:14][cH:15][cH:16][c:17]1[F:18]>CC(=O)O.CCOC(C)=O.O=S(=O)(O)O>[NH2:1][c:2]1[n:3][cH:4][c:5]([Br:6])[cH:7][c:8]1[O:9][CH2:10][c:11]1[c:12]([F:13])[cH:14][cH:15][cH:16][c:17]1[F:18]\"}",
"reactionStep": {
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"reactionHash": "1dc18a6577c77dec5bb08e1327f7ec284d6599b9ca6d9a18425d3ea74856c02d"
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"children": [
{
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"moleculeId": "sa_24211e89e565c162ea935f73",
"parentId": "13120",
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"molecule": {
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"inchikey": "GDTBXPJZTBHREO-UHFFFAOYSA-N",
"smiles": "BrBr"
},
"smiles": "BrBr",
"reactionStepId": null,
"template": null,
"metadata": null,
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},
{
"id": "13122",
"routeId": "sa_9f64e156f8ee4fa671ec36a6",
"moleculeId": "sa_02639770adc4bdbe1e8550d6",
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"molecule": {
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"inchikey": "LBZQPIOLPBOVRI-UHFFFAOYSA-N",
"smiles": "Nc1ncccc1OCc1c(F)cccc1F"
},
"smiles": "Nc1ncccc1OCc1c(F)cccc1F",
"reactionStepId": "sa_f7fb4b27dbd7337502843429",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140128386A1;1000;1522888\",\"rsmi\":\"Br[CH2:9][c:10]1[c:11]([F:12])[cH:13][cH:14][cH:15][c:16]1[F:17].[NH2:1][c:2]1[n:3][cH:4][cH:5][cH:6][c:7]1[OH:8]>CO.CO.O.[Na+]>[NH2:1][c:2]1[n:3][cH:4][cH:5][cH:6][c:7]1[O:8][CH2:9][c:10]1[c:11]([F:12])[cH:13][cH:14][cH:15][c:16]1[F:17]\"},\"mapped_reaction_smiles\":\"Br[CH2:9][c:10]1[c:11]([F:12])[cH:13][cH:14][cH:15][c:16]1[F:17].[NH2:1][c:2]1[n:3][cH:4][cH:5][cH:6][c:7]1[OH:8]>CO.CO.O.[Na+]>[NH2:1][c:2]1[n:3][cH:4][cH:5][cH:6][c:7]1[O:8][CH2:9][c:10]1[c:11]([F:12])[cH:13][cH:14][cH:15][c:16]1[F:17]\"}",
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"children": [
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"molecule": {
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"inchikey": "BMTSZVZQNMNPCT-UHFFFAOYSA-N",
"smiles": "Nc1ncccc1O"
},
"smiles": "Nc1ncccc1O",
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{
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"molecule": {
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"inchikey": "LSXJPJGBWSZHTM-UHFFFAOYSA-N",
"smiles": "Fc1cccc(F)c1CBr"
},
"smiles": "Fc1cccc(F)c1CBr",
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}
]
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]
}
]
}
]
}
]
}
]
}
}