Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CSc1ccc(CNCc2ccc(C3=NOC(O)(C(F)(F)F)C3)cc2)cc1
InChiKey
HNRNNYRSFNSBFD-UHFFFAOYSA-N
Route Signature
6e563627a7977b4beb16cc270700c7946a2e41438d4c6ada03af45701f45e653
Synthesis route with 6 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_2d2223e2c9c337e3baa6aea6",
"signature": "6e563627a7977b4beb16cc270700c7946a2e41438d4c6ada03af45701f45e653",
"contentHash": "e77b695bbc45cb07b7f9f7082b5c905472156dae2675fbba218b5e5f9fab4fbb",
"length": 6,
"isConvergent": false
},
"target": {
"id": "sa_bd710cb592af09dc7517ebd6",
"benchmarkSetId": "61e696668b63e77d7c2a29c0821768e1c383de8313852d6e995224859494442e",
"targetId": "n5-00418",
"moleculeId": "sa_be0d5865216f21eec46dcdae",
"smiles": "CSc1ccc(CNCc2ccc(C3=NOC(O)(C(F)(F)F)C3)cc2)cc1",
"routeLength": 6,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_be0d5865216f21eec46dcdae",
"inchikey": "HNRNNYRSFNSBFD-UHFFFAOYSA-N",
"smiles": "CSc1ccc(CNCc2ccc(C3=NOC(O)(C(F)(F)F)C3)cc2)cc1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "4246",
"routeId": "sa_2d2223e2c9c337e3baa6aea6",
"moleculeId": "sa_be0d5865216f21eec46dcdae",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_be0d5865216f21eec46dcdae",
"inchikey": "HNRNNYRSFNSBFD-UHFFFAOYSA-N",
"smiles": "CSc1ccc(CNCc2ccc(C3=NOC(O)(C(F)(F)F)C3)cc2)cc1"
},
"smiles": "CSc1ccc(CNCc2ccc(C3=NOC(O)(C(F)(F)F)C3)cc2)cc1",
"reactionStepId": "sa_42778d1d59d926b2f0b13c1f",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20080027059A1;0243;541555\",\"rsmi\":\"O=[CH:7][c:6]1[cH:5][cH:4][c:3]([S:2][CH3:1])[cH:27][cH:26]1.[NH2:8][CH2:9][c:10]1[cH:11][cH:12][c:13]([C:14]2=[N:15][O:16][C:17]([OH:18])([C:19]([F:20])([F:21])[F:22])[CH2:23]2)[cH:24][cH:25]1>CC(=O)OB(OC(C)=O)OC(C)=O.ClC(Cl)Cl.[Na+]>[CH3:1][S:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][NH:8][CH2:9][c:10]2[cH:11][cH:12][c:13]([C:14]3=[N:15][O:16][C:17]([OH:18])([C:19]([F:20])([F:21])[F:22])[CH2:23]3)[cH:24][cH:25]2)[cH:26][cH:27]1\"},\"mapped_reaction_smiles\":\"O=[CH:7][c:6]1[cH:5][cH:4][c:3]([S:2][CH3:1])[cH:27][cH:26]1.[NH2:8][CH2:9][c:10]1[cH:11][cH:12][c:13]([C:14]2=[N:15][O:16][C:17]([OH:18])([C:19]([F:20])([F:21])[F:22])[CH2:23]2)[cH:24][cH:25]1>CC(=O)OB(OC(C)=O)OC(C)=O.ClC(Cl)Cl.[Na+]>[CH3:1][S:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][NH:8][CH2:9][c:10]2[cH:11][cH:12][c:13]([C:14]3=[N:15][O:16][C:17]([OH:18])([C:19]([F:20])([F:21])[F:22])[CH2:23]3)[cH:24][cH:25]2)[cH:26][cH:27]1\"}",
"reactionStep": {
"id": "sa_42778d1d59d926b2f0b13c1f",
"reactionHash": "df268ebb5f1cff7a88c51d02c33d0098b62602a82ae924ba2bcc43b9dc778444"
},
"children": [
{
"id": "4247",
"routeId": "sa_2d2223e2c9c337e3baa6aea6",
"moleculeId": "sa_d30a232da245ffefb1789a6c",
"parentId": "4246",
"isLeaf": true,
"molecule": {
"id": "sa_d30a232da245ffefb1789a6c",
"inchikey": "QRVYABWJVXXOTN-UHFFFAOYSA-N",
"smiles": "CSc1ccc(C=O)cc1"
},
"smiles": "CSc1ccc(C=O)cc1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "4248",
"routeId": "sa_2d2223e2c9c337e3baa6aea6",
"moleculeId": "sa_2fe493e18ed5dd05208ccc9a",
"parentId": "4246",
"isLeaf": false,
"molecule": {
"id": "sa_2fe493e18ed5dd05208ccc9a",
"inchikey": "YGQKDCBOTGPUET-UHFFFAOYSA-N",
"smiles": "NCc1ccc(C2=NOC(O)(C(F)(F)F)C2)cc1"
},
"smiles": "NCc1ccc(C2=NOC(O)(C(F)(F)F)C2)cc1",
"reactionStepId": "sa_99f03c9ae79f516e267badf6",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20080027059A1;0229;541554\",\"rsmi\":\"[N-]=[N+]=[N:1][CH2:2][c:3]1[cH:4][cH:5][c:6]([C:7]2=[N:8][O:9][C:10]([OH:11])([C:12]([F:13])([F:14])[F:15])[CH2:16]2)[cH:17][cH:18]1>C1CCOC1.O.c1ccc(P(c2ccccc2)c2ccccc2)cc1>[NH2:1][CH2:2][c:3]1[cH:4][cH:5][c:6]([C:7]2=[N:8][O:9][C:10]([OH:11])([C:12]([F:13])([F:14])[F:15])[CH2:16]2)[cH:17][cH:18]1\"},\"mapped_reaction_smiles\":\"[N-]=[N+]=[N:1][CH2:2][c:3]1[cH:4][cH:5][c:6]([C:7]2=[N:8][O:9][C:10]([OH:11])([C:12]([F:13])([F:14])[F:15])[CH2:16]2)[cH:17][cH:18]1>C1CCOC1.O.c1ccc(P(c2ccccc2)c2ccccc2)cc1>[NH2:1][CH2:2][c:3]1[cH:4][cH:5][c:6]([C:7]2=[N:8][O:9][C:10]([OH:11])([C:12]([F:13])([F:14])[F:15])[CH2:16]2)[cH:17][cH:18]1\"}",
"reactionStep": {
"id": "sa_99f03c9ae79f516e267badf6",
"reactionHash": "6a66b3ba61c53813f0cf2f235f3b3134c9a05c51b3d1bceb7af257bac1ce4182"
},
"children": [
{
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"moleculeId": "sa_804dc8e607abce3e3c1e0bbb",
"parentId": "4248",
"isLeaf": false,
"molecule": {
"id": "sa_804dc8e607abce3e3c1e0bbb",
"inchikey": "YNQTXCJLLJXMAN-UHFFFAOYSA-N",
"smiles": "[N-]=[N+]=NCc1ccc(C2=NOC(O)(C(F)(F)F)C2)cc1"
},
"smiles": "[N-]=[N+]=NCc1ccc(C2=NOC(O)(C(F)(F)F)C2)cc1",
"reactionStepId": "sa_71f0d2da2ae97ef7a3a02e08",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20080027059A1;0214;541552\",\"rsmi\":\"O=[C:9]([c:8]1[cH:7][cH:6][c:5]([CH2:4][N:3]=[N+:2]=[N-:1])[cH:20][cH:19]1)[CH2:18][C:12](=[O:13])[C:14]([F:15])([F:16])[F:17].[NH2:10][OH:11]>CCO.Cl.O.[Na+].O>[N-:1]=[N+:2]=[N:3][CH2:4][c:5]1[cH:6][cH:7][c:8]([C:9]2=[N:10][O:11][C:12]([OH:13])([C:14]([F:15])([F:16])[F:17])[CH2:18]2)[cH:19][cH:20]1\"},\"mapped_reaction_smiles\":\"O=[C:9]([c:8]1[cH:7][cH:6][c:5]([CH2:4][N:3]=[N+:2]=[N-:1])[cH:20][cH:19]1)[CH2:18][C:12](=[O:13])[C:14]([F:15])([F:16])[F:17].[NH2:10][OH:11]>CCO.Cl.O.[Na+].O>[N-:1]=[N+:2]=[N:3][CH2:4][c:5]1[cH:6][cH:7][c:8]([C:9]2=[N:10][O:11][C:12]([OH:13])([C:14]([F:15])([F:16])[F:17])[CH2:18]2)[cH:19][cH:20]1\"}",
"reactionStep": {
"id": "sa_71f0d2da2ae97ef7a3a02e08",
"reactionHash": "22ec634a766ca0e3b0c883c295a147884c4c5cb0f1e2bb8340c8e1e472f37d7b"
},
"children": [
{
"id": "4250",
"routeId": "sa_2d2223e2c9c337e3baa6aea6",
"moleculeId": "sa_04a18e3f07bde82ca29399ee",
"parentId": "4249",
"isLeaf": true,
"molecule": {
"id": "sa_04a18e3f07bde82ca29399ee",
"inchikey": "AVXURJPOCDRRFD-UHFFFAOYSA-N",
"smiles": "NO"
},
"smiles": "NO",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "4251",
"routeId": "sa_2d2223e2c9c337e3baa6aea6",
"moleculeId": "sa_232ae7b55cdde5a9d2a70eef",
"parentId": "4249",
"isLeaf": false,
"molecule": {
"id": "sa_232ae7b55cdde5a9d2a70eef",
"inchikey": "HUIRZAIQNPLLJM-UHFFFAOYSA-N",
"smiles": "[N-]=[N+]=NCc1ccc(C(=O)CC(=O)C(F)(F)F)cc1"
},
"smiles": "[N-]=[N+]=NCc1ccc(C(=O)CC(=O)C(F)(F)F)cc1",
"reactionStepId": "sa_bfee9faa31dd905226c9172f",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20080027059A1;0199;541551\",\"rsmi\":\"CCO[C:12](=[O:13])[C:14]([F:15])([F:16])[F:17].[N-:1]=[N+:2]=[N:3][CH2:4][c:5]1[cH:6][cH:7][c:8]([C:9](=[O:10])[CH3:11])[cH:18][cH:19]1>CCO.[Na]>[N-:1]=[N+:2]=[N:3][CH2:4][c:5]1[cH:6][cH:7][c:8]([C:9](=[O:10])[CH2:11][C:12](=[O:13])[C:14]([F:15])([F:16])[F:17])[cH:18][cH:19]1\"},\"mapped_reaction_smiles\":\"CCO[C:12](=[O:13])[C:14]([F:15])([F:16])[F:17].[N-:1]=[N+:2]=[N:3][CH2:4][c:5]1[cH:6][cH:7][c:8]([C:9](=[O:10])[CH3:11])[cH:18][cH:19]1>CCO.[Na]>[N-:1]=[N+:2]=[N:3][CH2:4][c:5]1[cH:6][cH:7][c:8]([C:9](=[O:10])[CH2:11][C:12](=[O:13])[C:14]([F:15])([F:16])[F:17])[cH:18][cH:19]1\"}",
"reactionStep": {
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"reactionHash": "a039a5ef3ef6d0adc48e9b74ef1678943b397b39d43f253714b2579c51db463b"
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"children": [
{
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"routeId": "sa_2d2223e2c9c337e3baa6aea6",
"moleculeId": "sa_176f4fa669406a502f25dc59",
"parentId": "4251",
"isLeaf": false,
"molecule": {
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"inchikey": "IIKMOGOALQUZKA-UHFFFAOYSA-N",
"smiles": "CC(=O)c1ccc(CN=[N+]=[N-])cc1"
},
"smiles": "CC(=O)c1ccc(CN=[N+]=[N-])cc1",
"reactionStepId": "sa_35bcfc5912cf8b4e0cc49a63",
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"metadata": "{\"annotations\":{\"ID\":\"US20080027059A1;0193;541550\",\"rsmi\":\"Br[CH2:8][c:7]1[cH:6][cH:5][c:4]([C:2]([CH3:1])=[O:3])[cH:13][cH:12]1.[N-:9]=[N+:10]=[N-:11]>CN(C)C=O.O.[Na+]>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]([CH2:8][N:9]=[N+:10]=[N-:11])[cH:12][cH:13]1\"},\"mapped_reaction_smiles\":\"Br[CH2:8][c:7]1[cH:6][cH:5][c:4]([C:2]([CH3:1])=[O:3])[cH:13][cH:12]1.[N-:9]=[N+:10]=[N-:11]>CN(C)C=O.O.[Na+]>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]([CH2:8][N:9]=[N+:10]=[N-:11])[cH:12][cH:13]1\"}",
"reactionStep": {
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"reactionHash": "ad10c16f7e7f015706ac8e1d05b84e47172f12d70c66e62664481eaa088321a1"
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"children": [
{
"id": "4253",
"routeId": "sa_2d2223e2c9c337e3baa6aea6",
"moleculeId": "sa_233dd97bc59654cf138312c4",
"parentId": "4252",
"isLeaf": false,
"molecule": {
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"inchikey": "HARITLZHGNEHDS-UHFFFAOYSA-N",
"smiles": "CC(=O)c1ccc(CBr)cc1"
},
"smiles": "CC(=O)c1ccc(CBr)cc1",
"reactionStepId": "sa_e6398d42f407416a5df24142",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20080027059A1;0187;541549\",\"rsmi\":\"O=C1CCC(=O)N1[Br:9].[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]([CH3:8])[cH:10][cH:11]1>CC(C)(C#N)N=NC(C)(C)C#N.CCCC[n+]1ccn(C)c1.F[PH](F)(F)(F)(F)F>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]([CH2:8][Br:9])[cH:10][cH:11]1\"},\"mapped_reaction_smiles\":\"O=C1CCC(=O)N1[Br:9].[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]([CH3:8])[cH:10][cH:11]1>CC(C)(C#N)N=NC(C)(C)C#N.CCCC[n+]1ccn(C)c1.F[PH](F)(F)(F)(F)F>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]([CH2:8][Br:9])[cH:10][cH:11]1\"}",
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"children": [
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"parentId": "4253",
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"molecule": {
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"smiles": "CC(=O)c1ccc(C)cc1"
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"smiles": "CC(=O)c1ccc(C)cc1",
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{
"id": "4255",
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"molecule": {
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"inchikey": "PCLIMKBDDGJMGD-UHFFFAOYSA-N",
"smiles": "O=C1CCC(=O)N1Br"
},
"smiles": "O=C1CCC(=O)N1Br",
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{
"id": "4256",
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"molecule": {
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{
"id": "4257",
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"molecule": {
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"smiles": "CCOC(=O)C(F)(F)F"
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]
}
]
}
}