Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CCN1CCN(c2ccc(N3C[C@H](CN=[N+]=[N-])OC3=O)cc2F)CC1=O
InChiKey
GCTCRGASVUQZAI-LBPRGKRZSA-N
Route Signature
14a209d81860c2893fbdd4898e04f3fdb982a5886b3e29e25735043a3119f6f9
Synthesis route with 6 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_1224b48eabc0be7add267450",
"signature": "14a209d81860c2893fbdd4898e04f3fdb982a5886b3e29e25735043a3119f6f9",
"contentHash": "8224c9904f327c39e4b50fae2f045229775b65d2f2eba0a3cb934f39476648c7",
"length": 6,
"isConvergent": false
},
"target": {
"id": "sa_f0926cfc6a24be8962a47080",
"benchmarkSetId": "61e696668b63e77d7c2a29c0821768e1c383de8313852d6e995224859494442e",
"targetId": "n5-01173",
"moleculeId": "sa_d4dd33bb798db510606781aa",
"smiles": "CCN1CCN(c2ccc(N3C[C@H](CN=[N+]=[N-])OC3=O)cc2F)CC1=O",
"routeLength": 6,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_d4dd33bb798db510606781aa",
"inchikey": "GCTCRGASVUQZAI-LBPRGKRZSA-N",
"smiles": "CCN1CCN(c2ccc(N3C[C@H](CN=[N+]=[N-])OC3=O)cc2F)CC1=O"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "14132",
"routeId": "sa_1224b48eabc0be7add267450",
"moleculeId": "sa_d4dd33bb798db510606781aa",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_d4dd33bb798db510606781aa",
"inchikey": "GCTCRGASVUQZAI-LBPRGKRZSA-N",
"smiles": "CCN1CCN(c2ccc(N3C[C@H](CN=[N+]=[N-])OC3=O)cc2F)CC1=O"
},
"smiles": "CCN1CCN(c2ccc(N3C[C@H](CN=[N+]=[N-])OC3=O)cc2F)CC1=O",
"reactionStepId": "sa_0685282dfaf9161b96112ca7",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US06069145;;473947\",\"rsmi\":\"CS(=O)(=O)O[CH2:15][C@H:14]1[CH2:13][N:12]([c:11]2[cH:10][c:8]([F:9])[c:7]([N:6]3[CH2:5][CH2:4][N:3]([CH2:2][CH3:1])[C:25](=[O:26])[CH2:24]3)[cH:23][cH:22]2)[C:20](=[O:21])[O:19]1.[N-:16]=[N+:17]=[N-:18]>CN(C)C=O.[Na+]>[CH3:1][CH2:2][N:3]1[CH2:4][CH2:5][N:6]([c:7]2[c:8]([F:9])[cH:10][c:11]([N:12]3[CH2:13][C@H:14]([CH2:15][N:16]=[N+:17]=[N-:18])[O:19][C:20]3=[O:21])[cH:22][cH:23]2)[CH2:24][C:25]1=[O:26]\"},\"mapped_reaction_smiles\":\"CS(=O)(=O)O[CH2:15][C@H:14]1[CH2:13][N:12]([c:11]2[cH:10][c:8]([F:9])[c:7]([N:6]3[CH2:5][CH2:4][N:3]([CH2:2][CH3:1])[C:25](=[O:26])[CH2:24]3)[cH:23][cH:22]2)[C:20](=[O:21])[O:19]1.[N-:16]=[N+:17]=[N-:18]>CN(C)C=O.[Na+]>[CH3:1][CH2:2][N:3]1[CH2:4][CH2:5][N:6]([c:7]2[c:8]([F:9])[cH:10][c:11]([N:12]3[CH2:13][C@H:14]([CH2:15][N:16]=[N+:17]=[N-:18])[O:19][C:20]3=[O:21])[cH:22][cH:23]2)[CH2:24][C:25]1=[O:26]\"}",
"reactionStep": {
"id": "sa_0685282dfaf9161b96112ca7",
"reactionHash": "d2570bae10b5ecc30309c8b5865faf74a2ca0f82e97f4156e28e325d68d9e0a9"
},
"children": [
{
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"routeId": "sa_1224b48eabc0be7add267450",
"moleculeId": "sa_9be744c05edb6b19644016d9",
"parentId": "14132",
"isLeaf": false,
"molecule": {
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"inchikey": "FBOBVEHZXVRRGZ-CYBMUJFWSA-N",
"smiles": "CCN1CCN(c2ccc(N3C[C@H](COS(C)(=O)=O)OC3=O)cc2F)CC1=O"
},
"smiles": "CCN1CCN(c2ccc(N3C[C@H](COS(C)(=O)=O)OC3=O)cc2F)CC1=O",
"reactionStepId": "sa_2247fe7921f9968d0c2686de",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US06069145;;473946\",\"rsmi\":\"Cl[S:17]([CH3:18])(=[O:19])=[O:20].[CH3:1][CH2:2][N:3]1[CH2:4][CH2:5][N:6]([c:7]2[c:8]([F:9])[cH:10][c:11]([N:12]3[CH2:13][C@H:14]([CH2:15][OH:16])[O:21][C:22]3=[O:23])[cH:24][cH:25]2)[CH2:26][C:27]1=[O:28]>CCN(CC)CC.c1ccncc1>[CH3:1][CH2:2][N:3]1[CH2:4][CH2:5][N:6]([c:7]2[c:8]([F:9])[cH:10][c:11]([N:12]3[CH2:13][C@H:14]([CH2:15][O:16][S:17]([CH3:18])(=[O:19])=[O:20])[O:21][C:22]3=[O:23])[cH:24][cH:25]2)[CH2:26][C:27]1=[O:28]\"},\"mapped_reaction_smiles\":\"Cl[S:17]([CH3:18])(=[O:19])=[O:20].[CH3:1][CH2:2][N:3]1[CH2:4][CH2:5][N:6]([c:7]2[c:8]([F:9])[cH:10][c:11]([N:12]3[CH2:13][C@H:14]([CH2:15][OH:16])[O:21][C:22]3=[O:23])[cH:24][cH:25]2)[CH2:26][C:27]1=[O:28]>CCN(CC)CC.c1ccncc1>[CH3:1][CH2:2][N:3]1[CH2:4][CH2:5][N:6]([c:7]2[c:8]([F:9])[cH:10][c:11]([N:12]3[CH2:13][C@H:14]([CH2:15][O:16][S:17]([CH3:18])(=[O:19])=[O:20])[O:21][C:22]3=[O:23])[cH:24][cH:25]2)[CH2:26][C:27]1=[O:28]\"}",
"reactionStep": {
"id": "sa_2247fe7921f9968d0c2686de",
"reactionHash": "5c60360053d3b8492a0b548b1796078db2ab7d372de76a8f9d18bb45e852489d"
},
"children": [
{
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"routeId": "sa_1224b48eabc0be7add267450",
"moleculeId": "sa_d2a31ea58046b00856f61ca5",
"parentId": "14133",
"isLeaf": true,
"molecule": {
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"inchikey": "QARBMVPHQWIHKH-UHFFFAOYSA-N",
"smiles": "CS(=O)(=O)Cl"
},
"smiles": "CS(=O)(=O)Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "14135",
"routeId": "sa_1224b48eabc0be7add267450",
"moleculeId": "sa_8f089c3b0190da9850c3015e",
"parentId": "14133",
"isLeaf": false,
"molecule": {
"id": "sa_8f089c3b0190da9850c3015e",
"inchikey": "XLPHNFVKPCDTQP-GFCCVEGCSA-N",
"smiles": "CCN1CCN(c2ccc(N3C[C@H](CO)OC3=O)cc2F)CC1=O"
},
"smiles": "CCN1CCN(c2ccc(N3C[C@H](CO)OC3=O)cc2F)CC1=O",
"reactionStepId": "sa_ac2c592e3dffffa2d3758e13",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US06069145;;473945\",\"rsmi\":\"CCCC(=O)[O:16][CH2:15][C@H:14]1[CH2:13][O:17]1.c1ccc(CO[C:18]([NH:12][c:11]2[cH:10][c:8]([F:9])[c:7]([N:6]3[CH2:5][CH2:4][N:3]([CH2:2][CH3:1])[C:23](=[O:24])[CH2:22]3)[cH:21][cH:20]2)=[O:19])cc1>C1CCOC1.CCOC(C)=O.CN1CCCN(C)C1=O.O=C(O)O.[Li]CCCC.[Na+]>[CH3:1][CH2:2][N:3]1[CH2:4][CH2:5][N:6]([c:7]2[c:8]([F:9])[cH:10][c:11]([N:12]3[CH2:13][C@H:14]([CH2:15][OH:16])[O:17][C:18]3=[O:19])[cH:20][cH:21]2)[CH2:22][C:23]1=[O:24]\"},\"mapped_reaction_smiles\":\"CCCC(=O)[O:16][CH2:15][C@H:14]1[CH2:13][O:17]1.c1ccc(CO[C:18]([NH:12][c:11]2[cH:10][c:8]([F:9])[c:7]([N:6]3[CH2:5][CH2:4][N:3]([CH2:2][CH3:1])[C:23](=[O:24])[CH2:22]3)[cH:21][cH:20]2)=[O:19])cc1>C1CCOC1.CCOC(C)=O.CN1CCCN(C)C1=O.O=C(O)O.[Li]CCCC.[Na+]>[CH3:1][CH2:2][N:3]1[CH2:4][CH2:5][N:6]([c:7]2[c:8]([F:9])[cH:10][c:11]([N:12]3[CH2:13][C@H:14]([CH2:15][OH:16])[O:17][C:18]3=[O:19])[cH:20][cH:21]2)[CH2:22][C:23]1=[O:24]\"}",
"reactionStep": {
"id": "sa_ac2c592e3dffffa2d3758e13",
"reactionHash": "f7c9edeba15fb404579fcd6b19709685f8860ee3115f665356eff327f002f05b"
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"children": [
{
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"routeId": "sa_1224b48eabc0be7add267450",
"moleculeId": "sa_1d1c1fd4128dc9b4ebfa5535",
"parentId": "14135",
"isLeaf": false,
"molecule": {
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"inchikey": "XFXCWCRXLFPXER-UHFFFAOYSA-N",
"smiles": "CCN1CCN(c2ccc(NC(=O)OCc3ccccc3)cc2F)CC1=O"
},
"smiles": "CCN1CCN(c2ccc(NC(=O)OCc3ccccc3)cc2F)CC1=O",
"reactionStepId": "sa_1ab1b7c08f43dbbb04793448",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US06069145;;473944\",\"rsmi\":\"Cl[C:13](=[O:14])[O:15][CH2:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1.[CH3:1][CH2:2][N:3]1[CH2:4][CH2:5][N:6]([c:7]2[c:8]([F:9])[cH:10][c:11]([NH2:12])[cH:23][cH:24]2)[CH2:25][C:26]1=[O:27]>ClCCl.c1ccncc1>[CH3:1][CH2:2][N:3]1[CH2:4][CH2:5][N:6]([c:7]2[c:8]([F:9])[cH:10][c:11]([NH:12][C:13](=[O:14])[O:15][CH2:16][c:17]3[cH:18][cH:19][cH:20][cH:21][cH:22]3)[cH:23][cH:24]2)[CH2:25][C:26]1=[O:27]\"},\"mapped_reaction_smiles\":\"Cl[C:13](=[O:14])[O:15][CH2:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1.[CH3:1][CH2:2][N:3]1[CH2:4][CH2:5][N:6]([c:7]2[c:8]([F:9])[cH:10][c:11]([NH2:12])[cH:23][cH:24]2)[CH2:25][C:26]1=[O:27]>ClCCl.c1ccncc1>[CH3:1][CH2:2][N:3]1[CH2:4][CH2:5][N:6]([c:7]2[c:8]([F:9])[cH:10][c:11]([NH:12][C:13](=[O:14])[O:15][CH2:16][c:17]3[cH:18][cH:19][cH:20][cH:21][cH:22]3)[cH:23][cH:24]2)[CH2:25][C:26]1=[O:27]\"}",
"reactionStep": {
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"children": [
{
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"molecule": {
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"smiles": "CCN1CCN(c2ccc(N)cc2F)CC1=O"
},
"smiles": "CCN1CCN(c2ccc(N)cc2F)CC1=O",
"reactionStepId": "sa_928722a8ff0d84c51f28e289",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US06069145;;473943\",\"rsmi\":\"O=[N+:12]([O-])[c:11]1[cH:10][c:8]([F:9])[c:7]([N:6]2[CH2:5][CH2:4][N:3]([CH2:2][CH3:1])[C:16](=[O:17])[CH2:15]2)[cH:14][cH:13]1>CCOC(C)=O>[CH3:1][CH2:2][N:3]1[CH2:4][CH2:5][N:6]([c:7]2[c:8]([F:9])[cH:10][c:11]([NH2:12])[cH:13][cH:14]2)[CH2:15][C:16]1=[O:17]\"},\"mapped_reaction_smiles\":\"O=[N+:12]([O-])[c:11]1[cH:10][c:8]([F:9])[c:7]([N:6]2[CH2:5][CH2:4][N:3]([CH2:2][CH3:1])[C:16](=[O:17])[CH2:15]2)[cH:14][cH:13]1>CCOC(C)=O>[CH3:1][CH2:2][N:3]1[CH2:4][CH2:5][N:6]([c:7]2[c:8]([F:9])[cH:10][c:11]([NH2:12])[cH:13][cH:14]2)[CH2:15][C:16]1=[O:17]\"}",
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"children": [
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"molecule": {
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"smiles": "CCN1CCN(c2ccc([N+](=O)[O-])cc2F)CC1=O",
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"metadata": "{\"annotations\":{\"ID\":\"US06069145;;473942\",\"rsmi\":\"F[c:7]1[c:8]([F:9])[cH:10][c:11]([N+:12](=[O:13])[O-:14])[cH:15][cH:16]1.[CH3:1][CH2:2][N:3]1[CH2:4][CH2:5][NH:6][CH2:17][C:18]1=[O:19]>CC#N.CCN(C(C)C)C(C)C.CCN(C(C)C)C(C)C.O=C(O)C(F)(F)F>[CH3:1][CH2:2][N:3]1[CH2:4][CH2:5][N:6]([c:7]2[c:8]([F:9])[cH:10][c:11]([N+:12](=[O:13])[O-:14])[cH:15][cH:16]2)[CH2:17][C:18]1=[O:19]\"},\"mapped_reaction_smiles\":\"F[c:7]1[c:8]([F:9])[cH:10][c:11]([N+:12](=[O:13])[O-:14])[cH:15][cH:16]1.[CH3:1][CH2:2][N:3]1[CH2:4][CH2:5][NH:6][CH2:17][C:18]1=[O:19]>CC#N.CCN(C(C)C)C(C)C.CCN(C(C)C)C(C)C.O=C(O)C(F)(F)F>[CH3:1][CH2:2][N:3]1[CH2:4][CH2:5][N:6]([c:7]2[c:8]([F:9])[cH:10][c:11]([N+:12](=[O:13])[O-:14])[cH:15][cH:16]2)[CH2:17][C:18]1=[O:19]\"}",
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"smiles": "O=[N+]([O-])c1ccc(F)c(F)c1",
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{
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{
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{
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{
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"smiles": "[N]N=[N-]"
},
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}
]
}
}