Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CC(C)(C)C(=O)NCc1ccc(Cl)c(C(=O)Nc2cccc3c(Oc4cccc(C(F)(F)F)c4)ncnc23)c1F
InChiKey
IIDIEZNVEIKWOP-UHFFFAOYSA-N
Route Signature
9f6fbfd4f2c51031df4b9b874a237ac19311b239ed457d5110d22c701f166653
Synthesis route with 4 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_f30d8e6765c3c160db12300e",
"signature": "9f6fbfd4f2c51031df4b9b874a237ac19311b239ed457d5110d22c701f166653",
"contentHash": "cf628411884815f2733d69d208ac90cb2423acc98da9f9fb2f3caabdaabb7f1a",
"length": 4,
"isConvergent": true
},
"target": {
"id": "sa_10d80c216e37bb57c668d8b6",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-01092",
"moleculeId": "sa_1c055981a15314b9b31fcd12",
"smiles": "CC(C)(C)C(=O)NCc1ccc(Cl)c(C(=O)Nc2cccc3c(Oc4cccc(C(F)(F)F)c4)ncnc23)c1F",
"routeLength": 4,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_1c055981a15314b9b31fcd12",
"inchikey": "IIDIEZNVEIKWOP-UHFFFAOYSA-N",
"smiles": "CC(C)(C)C(=O)NCc1ccc(Cl)c(C(=O)Nc2cccc3c(Oc4cccc(C(F)(F)F)c4)ncnc23)c1F"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "9938",
"routeId": "sa_f30d8e6765c3c160db12300e",
"moleculeId": "sa_1c055981a15314b9b31fcd12",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_1c055981a15314b9b31fcd12",
"inchikey": "IIDIEZNVEIKWOP-UHFFFAOYSA-N",
"smiles": "CC(C)(C)C(=O)NCc1ccc(Cl)c(C(=O)Nc2cccc3c(Oc4cccc(C(F)(F)F)c4)ncnc23)c1F"
},
"smiles": "CC(C)(C)C(=O)NCc1ccc(Cl)c(C(=O)Nc2cccc3c(Oc4cccc(C(F)(F)F)c4)ncnc23)c1F",
"reactionStepId": "sa_9b228f94ce1458fcea88d266",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130210844A1;0593;1407929\",\"rsmi\":\"O[C:15]([c:14]1[c:12]([Cl:13])[cH:11][cH:10][c:9]([CH2:8][NH:7][C:5]([C:2]([CH3:1])([CH3:3])[CH3:4])=[O:6])[c:39]1[F:40])=[O:16].[NH2:17][c:18]1[c:19]2[n:20][cH:21][n:22][c:23]([O:24][c:25]3[cH:26][c:27]([C:28]([F:29])([F:30])[F:31])[cH:32][cH:33][cH:34]3)[c:35]2[cH:36][cH:37][cH:38]1>CCN(C(C)C)C(C)C.CN(C)C=O.ClCCl.O=C(Cl)C(=O)Cl>[CH3:1][C:2]([CH3:3])([CH3:4])[C:5](=[O:6])[NH:7][CH2:8][c:9]1[cH:10][cH:11][c:12]([Cl:13])[c:14]([C:15](=[O:16])[NH:17][c:18]2[c:19]3[n:20][cH:21][n:22][c:23]([O:24][c:25]4[cH:26][c:27]([C:28]([F:29])([F:30])[F:31])[cH:32][cH:33][cH:34]4)[c:35]3[cH:36][cH:37][cH:38]2)[c:39]1[F:40]\"},\"mapped_reaction_smiles\":\"O[C:15]([c:14]1[c:12]([Cl:13])[cH:11][cH:10][c:9]([CH2:8][NH:7][C:5]([C:2]([CH3:1])([CH3:3])[CH3:4])=[O:6])[c:39]1[F:40])=[O:16].[NH2:17][c:18]1[c:19]2[n:20][cH:21][n:22][c:23]([O:24][c:25]3[cH:26][c:27]([C:28]([F:29])([F:30])[F:31])[cH:32][cH:33][cH:34]3)[c:35]2[cH:36][cH:37][cH:38]1>CCN(C(C)C)C(C)C.CN(C)C=O.ClCCl.O=C(Cl)C(=O)Cl>[CH3:1][C:2]([CH3:3])([CH3:4])[C:5](=[O:6])[NH:7][CH2:8][c:9]1[cH:10][cH:11][c:12]([Cl:13])[c:14]([C:15](=[O:16])[NH:17][c:18]2[c:19]3[n:20][cH:21][n:22][c:23]([O:24][c:25]4[cH:26][c:27]([C:28]([F:29])([F:30])[F:31])[cH:32][cH:33][cH:34]4)[c:35]3[cH:36][cH:37][cH:38]2)[c:39]1[F:40]\"}",
"reactionStep": {
"id": "sa_9b228f94ce1458fcea88d266",
"reactionHash": "5218a244ee4ef4dca9cb705456f93be4eadd4713992626dc511361083a35be40"
},
"children": [
{
"id": "9939",
"routeId": "sa_f30d8e6765c3c160db12300e",
"moleculeId": "sa_ce04a7f190744f33d1405e25",
"parentId": "9938",
"isLeaf": false,
"molecule": {
"id": "sa_ce04a7f190744f33d1405e25",
"inchikey": "NVYPAQULEJLDRB-UHFFFAOYSA-N",
"smiles": "CC(C)(C)C(=O)NCc1ccc(Cl)c(C(=O)O)c1F"
},
"smiles": "CC(C)(C)C(=O)NCc1ccc(Cl)c(C(=O)O)c1F",
"reactionStepId": "sa_8573a46b369d5cd61363bbc2",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130210844A1;0275;1407830\",\"rsmi\":\"CC[O:17][C:15]([c:14]1[c:12]([Cl:13])[cH:11][cH:10][c:9]([CH2:8][NH:7][C:5]([C:2]([CH3:1])([CH3:3])[CH3:4])=[O:6])[c:18]1[F:19])=[O:16]>C1CCOC1.CO.O.O=C(O)CC(O)(CC(=O)O)C(=O)O.[Na+].O>[CH3:1][C:2]([CH3:3])([CH3:4])[C:5](=[O:6])[NH:7][CH2:8][c:9]1[cH:10][cH:11][c:12]([Cl:13])[c:14]([C:15](=[O:16])[OH:17])[c:18]1[F:19]\"},\"mapped_reaction_smiles\":\"CC[O:17][C:15]([c:14]1[c:12]([Cl:13])[cH:11][cH:10][c:9]([CH2:8][NH:7][C:5]([C:2]([CH3:1])([CH3:3])[CH3:4])=[O:6])[c:18]1[F:19])=[O:16]>C1CCOC1.CO.O.O=C(O)CC(O)(CC(=O)O)C(=O)O.[Na+].O>[CH3:1][C:2]([CH3:3])([CH3:4])[C:5](=[O:6])[NH:7][CH2:8][c:9]1[cH:10][cH:11][c:12]([Cl:13])[c:14]([C:15](=[O:16])[OH:17])[c:18]1[F:19]\"}",
"reactionStep": {
"id": "sa_8573a46b369d5cd61363bbc2",
"reactionHash": "c3a02cc211a202ff82ad4dc9db41dd25978a0f23ff44aaff2143dad1c2f87593"
},
"children": [
{
"id": "9940",
"routeId": "sa_f30d8e6765c3c160db12300e",
"moleculeId": "sa_0bb89bb6865a2ec5f3cb5a6b",
"parentId": "9939",
"isLeaf": false,
"molecule": {
"id": "sa_0bb89bb6865a2ec5f3cb5a6b",
"inchikey": "PDELEDHLMMAVHQ-UHFFFAOYSA-N",
"smiles": "CCOC(=O)c1c(Cl)ccc(CNC(=O)C(C)(C)C)c1F"
},
"smiles": "CCOC(=O)c1c(Cl)ccc(CNC(=O)C(C)(C)C)c1F",
"reactionStepId": "sa_1f17437548a68afb686c87b9",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130210844A1;0274;1407829\",\"rsmi\":\"Cl[C:12](=[O:13])[C:14]([CH3:15])([CH3:16])[CH3:17].[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7]([F:8])[c:9]([CH2:10][NH2:11])[cH:18][cH:19][c:20]1[Cl:21]>C1CCOC1.CCN(CC)CC.CCOC(C)=O>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7]([F:8])[c:9]([CH2:10][NH:11][C:12](=[O:13])[C:14]([CH3:15])([CH3:16])[CH3:17])[cH:18][cH:19][c:20]1[Cl:21]\"},\"mapped_reaction_smiles\":\"Cl[C:12](=[O:13])[C:14]([CH3:15])([CH3:16])[CH3:17].[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7]([F:8])[c:9]([CH2:10][NH2:11])[cH:18][cH:19][c:20]1[Cl:21]>C1CCOC1.CCN(CC)CC.CCOC(C)=O>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7]([F:8])[c:9]([CH2:10][NH:11][C:12](=[O:13])[C:14]([CH3:15])([CH3:16])[CH3:17])[cH:18][cH:19][c:20]1[Cl:21]\"}",
"reactionStep": {
"id": "sa_1f17437548a68afb686c87b9",
"reactionHash": "9ccae5757dc863481e98659b45d484bec89960b3047c54d8ca12d10982526947"
},
"children": [
{
"id": "9941",
"routeId": "sa_f30d8e6765c3c160db12300e",
"moleculeId": "sa_38976d19d9d1312f3c89539c",
"parentId": "9940",
"isLeaf": true,
"molecule": {
"id": "sa_38976d19d9d1312f3c89539c",
"inchikey": "HSQXWMNADXUWFI-UHFFFAOYSA-N",
"smiles": "CCOC(=O)c1c(Cl)ccc(CN)c1F"
},
"smiles": "CCOC(=O)c1c(Cl)ccc(CN)c1F",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "9942",
"routeId": "sa_f30d8e6765c3c160db12300e",
"moleculeId": "sa_c4a4e8fc10f9a494534f9123",
"parentId": "9940",
"isLeaf": true,
"molecule": {
"id": "sa_c4a4e8fc10f9a494534f9123",
"inchikey": "JVSFQJZRHXAUGT-UHFFFAOYSA-N",
"smiles": "CC(C)(C)C(=O)Cl"
},
"smiles": "CC(C)(C)C(=O)Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
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}
]
}
]
},
{
"id": "9943",
"routeId": "sa_f30d8e6765c3c160db12300e",
"moleculeId": "sa_416bb0b36458d8e982fbb472",
"parentId": "9938",
"isLeaf": false,
"molecule": {
"id": "sa_416bb0b36458d8e982fbb472",
"inchikey": "QXBOSYYKRMIROP-UHFFFAOYSA-N",
"smiles": "Nc1cccc2c(Oc3cccc(C(F)(F)F)c3)ncnc12"
},
"smiles": "Nc1cccc2c(Oc3cccc(C(F)(F)F)c3)ncnc12",
"reactionStepId": "sa_3c115df2ce3557782b56061a",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130210844A1;0319;1407849\",\"rsmi\":\"O=[N+:1]([O-])[c:2]1[c:3]2[n:4][cH:5][n:6][c:7]([O:8][c:9]3[cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[cH:16][cH:17][cH:18]3)[c:19]2[cH:20][cH:21][cH:22]1>CCOC(C)=O.[Pd]>[NH2:1][c:2]1[c:3]2[n:4][cH:5][n:6][c:7]([O:8][c:9]3[cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[cH:16][cH:17][cH:18]3)[c:19]2[cH:20][cH:21][cH:22]1\"},\"mapped_reaction_smiles\":\"O=[N+:1]([O-])[c:2]1[c:3]2[n:4][cH:5][n:6][c:7]([O:8][c:9]3[cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[cH:16][cH:17][cH:18]3)[c:19]2[cH:20][cH:21][cH:22]1>CCOC(C)=O.[Pd]>[NH2:1][c:2]1[c:3]2[n:4][cH:5][n:6][c:7]([O:8][c:9]3[cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[cH:16][cH:17][cH:18]3)[c:19]2[cH:20][cH:21][cH:22]1\"}",
"reactionStep": {
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"reactionHash": "49e110fb8dad83cf3813a84bf74aebca3b5d2a577b6f40110356952a6aff5c39"
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"children": [
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"moleculeId": "sa_0fbc0f7f727ae9b0ec9a03e7",
"parentId": "9943",
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"molecule": {
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"inchikey": "KHTAPGZXIJYWKJ-UHFFFAOYSA-N",
"smiles": "O=[N+]([O-])c1cccc2c(Oc3cccc(C(F)(F)F)c3)ncnc12"
},
"smiles": "O=[N+]([O-])c1cccc2c(Oc3cccc(C(F)(F)F)c3)ncnc12",
"reactionStepId": "sa_086b13aed68c36604af69e9a",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130210844A1;0318;1407848\",\"rsmi\":\"Cl[c:9]1[n:8][cH:7][n:6][c:5]2[c:4]([N+:2](=[O:1])[O-:3])[cH:24][cH:23][cH:22][c:21]21.[OH:10][c:11]1[cH:12][c:13]([C:14]([F:15])([F:16])[F:17])[cH:18][cH:19][cH:20]1>C1CCOC1.[HH].[Na+]>[O:1]=[N+:2]([O-:3])[c:4]1[c:5]2[n:6][cH:7][n:8][c:9]([O:10][c:11]3[cH:12][c:13]([C:14]([F:15])([F:16])[F:17])[cH:18][cH:19][cH:20]3)[c:21]2[cH:22][cH:23][cH:24]1\"},\"mapped_reaction_smiles\":\"Cl[c:9]1[n:8][cH:7][n:6][c:5]2[c:4]([N+:2](=[O:1])[O-:3])[cH:24][cH:23][cH:22][c:21]21.[OH:10][c:11]1[cH:12][c:13]([C:14]([F:15])([F:16])[F:17])[cH:18][cH:19][cH:20]1>C1CCOC1.[HH].[Na+]>[O:1]=[N+:2]([O-:3])[c:4]1[c:5]2[n:6][cH:7][n:8][c:9]([O:10][c:11]3[cH:12][c:13]([C:14]([F:15])([F:16])[F:17])[cH:18][cH:19][cH:20]3)[c:21]2[cH:22][cH:23][cH:24]1\"}",
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"molecule": {
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"inchikey": "UGEJOEBBMPOJMT-UHFFFAOYSA-N",
"smiles": "Oc1cccc(C(F)(F)F)c1"
},
"smiles": "Oc1cccc(C(F)(F)F)c1",
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{
"id": "9946",
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"molecule": {
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"inchikey": "YNIKQCKETYIRTH-UHFFFAOYSA-N",
"smiles": "O=[N+]([O-])c1cccc2c(Cl)ncnc12"
},
"smiles": "O=[N+]([O-])c1cccc2c(Cl)ncnc12",
"reactionStepId": "sa_511af5a11e285371b9d82dc3",
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"metadata": "{\"annotations\":{\"ID\":\"US20130210844A1;0312;1407845\",\"rsmi\":\"O=P(Cl)(Cl)[Cl:10].O=[c:9]1[nH:8][cH:7][n:6][c:5]2[c:4]([N+:2](=[O:1])[O-:3])[cH:14][cH:13][cH:12][c:11]21>ClP(Cl)(Cl)(Cl)Cl>[O:1]=[N+:2]([O-:3])[c:4]1[c:5]2[n:6][cH:7][n:8][c:9]([Cl:10])[c:11]2[cH:12][cH:13][cH:14]1\"},\"mapped_reaction_smiles\":\"O=P(Cl)(Cl)[Cl:10].O=[c:9]1[nH:8][cH:7][n:6][c:5]2[c:4]([N+:2](=[O:1])[O-:3])[cH:14][cH:13][cH:12][c:11]21>ClP(Cl)(Cl)(Cl)Cl>[O:1]=[N+:2]([O-:3])[c:4]1[c:5]2[n:6][cH:7][n:8][c:9]([Cl:10])[c:11]2[cH:12][cH:13][cH:14]1\"}",
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"molecule": {
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{
"id": "9948",
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"smiles": "O=P(Cl)(Cl)Cl"
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}
]
}
]
}
]
}
]
}
}