Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CN(c1cccc2cc(C3=NCC(C)(CCOS(C)(=O)=O)S3)[nH]c12)S(=O)(=O)c1cccs1
InChiKey
XCMNENLIVLHLMH-UHFFFAOYSA-N
Route Signature
9538e829ea4565d9c35d96f7cd00056da430e995d3cb040b2ee1e9548e0b3fa2
Synthesis route with 4 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_42dce7d0267dc2a59debf00a",
"signature": "9538e829ea4565d9c35d96f7cd00056da430e995d3cb040b2ee1e9548e0b3fa2",
"contentHash": "67ade5d09a62c3be016c2ddfa4c7686bd183b61ee81103eeb28d74a7c26aa46f",
"length": 4,
"isConvergent": true
},
"target": {
"id": "sa_701f2966040e3bbb739d61ce",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-01664",
"moleculeId": "sa_4e15eabcd1e80e237a4c9079",
"smiles": "CN(c1cccc2cc(C3=NCC(C)(CCOS(C)(=O)=O)S3)[nH]c12)S(=O)(=O)c1cccs1",
"routeLength": 4,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_4e15eabcd1e80e237a4c9079",
"inchikey": "XCMNENLIVLHLMH-UHFFFAOYSA-N",
"smiles": "CN(c1cccc2cc(C3=NCC(C)(CCOS(C)(=O)=O)S3)[nH]c12)S(=O)(=O)c1cccs1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "10366",
"routeId": "sa_42dce7d0267dc2a59debf00a",
"moleculeId": "sa_4e15eabcd1e80e237a4c9079",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_4e15eabcd1e80e237a4c9079",
"inchikey": "XCMNENLIVLHLMH-UHFFFAOYSA-N",
"smiles": "CN(c1cccc2cc(C3=NCC(C)(CCOS(C)(=O)=O)S3)[nH]c12)S(=O)(=O)c1cccs1"
},
"smiles": "CN(c1cccc2cc(C3=NCC(C)(CCOS(C)(=O)=O)S3)[nH]c12)S(=O)(=O)c1cccs1",
"reactionStepId": "sa_9882993c75efb4fe7b445ed5",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100144702A1;2947;895049\",\"rsmi\":\"Cl[S:15]([CH3:16])(=[O:17])=[O:18].[CH3:1][N:2]([c:3]1[c:4]2[nH:5][c:6]([C:7]3=[N:8][CH2:9][C:10]([CH3:11])([CH2:12][CH2:13][OH:14])[S:19]3)[cH:20][c:21]2[cH:22][cH:23][cH:24]1)[S:25](=[O:26])(=[O:27])[c:28]1[cH:29][cH:30][cH:31][s:32]1>C1CCOC1.CCN(CC)CC.O>[CH3:1][N:2]([c:3]1[c:4]2[nH:5][c:6]([C:7]3=[N:8][CH2:9][C:10]([CH3:11])([CH2:12][CH2:13][O:14][S:15]([CH3:16])(=[O:17])=[O:18])[S:19]3)[cH:20][c:21]2[cH:22][cH:23][cH:24]1)[S:25](=[O:26])(=[O:27])[c:28]1[cH:29][cH:30][cH:31][s:32]1\"},\"mapped_reaction_smiles\":\"Cl[S:15]([CH3:16])(=[O:17])=[O:18].[CH3:1][N:2]([c:3]1[c:4]2[nH:5][c:6]([C:7]3=[N:8][CH2:9][C:10]([CH3:11])([CH2:12][CH2:13][OH:14])[S:19]3)[cH:20][c:21]2[cH:22][cH:23][cH:24]1)[S:25](=[O:26])(=[O:27])[c:28]1[cH:29][cH:30][cH:31][s:32]1>C1CCOC1.CCN(CC)CC.O>[CH3:1][N:2]([c:3]1[c:4]2[nH:5][c:6]([C:7]3=[N:8][CH2:9][C:10]([CH3:11])([CH2:12][CH2:13][O:14][S:15]([CH3:16])(=[O:17])=[O:18])[S:19]3)[cH:20][c:21]2[cH:22][cH:23][cH:24]1)[S:25](=[O:26])(=[O:27])[c:28]1[cH:29][cH:30][cH:31][s:32]1\"}",
"reactionStep": {
"id": "sa_9882993c75efb4fe7b445ed5",
"reactionHash": "45d43550d4a951a55f972eb44f2d5dc314b3b01b8f2485a831dc7fb7d23d1c4e"
},
"children": [
{
"id": "10367",
"routeId": "sa_42dce7d0267dc2a59debf00a",
"moleculeId": "sa_bc8f22ca33b620728f63f968",
"parentId": "10366",
"isLeaf": false,
"molecule": {
"id": "sa_bc8f22ca33b620728f63f968",
"inchikey": "KTEOQIISSNNSHK-UHFFFAOYSA-N",
"smiles": "CN(c1cccc2cc(C3=NCC(C)(CCO)S3)[nH]c12)S(=O)(=O)c1cccs1"
},
"smiles": "CN(c1cccc2cc(C3=NCC(C)(CCO)S3)[nH]c12)S(=O)(=O)c1cccs1",
"reactionStepId": "sa_62feb484b96c3d0fd3160423",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100144702A1;2340;894895\",\"rsmi\":\"O=[C:7]([c:6]1[nH:5][c:4]2[c:3]([N:2]([CH3:1])[S:21](=[O:22])(=[O:23])[c:24]3[cH:25][cH:26][cH:27][s:28]3)[cH:20][cH:19][cH:18][c:17]2[cH:16]1)[NH:8][CH2:9][C:10]([CH3:11])([CH2:12][CH2:13][OH:14])[S:15]Cc1ccccc1>CC#N.O=C(O)O.O=P(c1ccccc1)(c1ccccc1)c1ccccc1.O=S(=O)(OS(=O)(=O)C(F)(F)F)C(F)(F)F.[Na+]>[CH3:1][N:2]([c:3]1[c:4]2[nH:5][c:6]([C:7]3=[N:8][CH2:9][C:10]([CH3:11])([CH2:12][CH2:13][OH:14])[S:15]3)[cH:16][c:17]2[cH:18][cH:19][cH:20]1)[S:21](=[O:22])(=[O:23])[c:24]1[cH:25][cH:26][cH:27][s:28]1\"},\"mapped_reaction_smiles\":\"O=[C:7]([c:6]1[nH:5][c:4]2[c:3]([N:2]([CH3:1])[S:21](=[O:22])(=[O:23])[c:24]3[cH:25][cH:26][cH:27][s:28]3)[cH:20][cH:19][cH:18][c:17]2[cH:16]1)[NH:8][CH2:9][C:10]([CH3:11])([CH2:12][CH2:13][OH:14])[S:15]Cc1ccccc1>CC#N.O=C(O)O.O=P(c1ccccc1)(c1ccccc1)c1ccccc1.O=S(=O)(OS(=O)(=O)C(F)(F)F)C(F)(F)F.[Na+]>[CH3:1][N:2]([c:3]1[c:4]2[nH:5][c:6]([C:7]3=[N:8][CH2:9][C:10]([CH3:11])([CH2:12][CH2:13][OH:14])[S:15]3)[cH:16][c:17]2[cH:18][cH:19][cH:20]1)[S:21](=[O:22])(=[O:23])[c:24]1[cH:25][cH:26][cH:27][s:28]1\"}",
"reactionStep": {
"id": "sa_62feb484b96c3d0fd3160423",
"reactionHash": "2a4827503d59cb7fecb78e0fd0f75196587d5646774e6e4def02c1b723ae37a4"
},
"children": [
{
"id": "10368",
"routeId": "sa_42dce7d0267dc2a59debf00a",
"moleculeId": "sa_2be818cc9eec5aee6d52c05e",
"parentId": "10367",
"isLeaf": false,
"molecule": {
"id": "sa_2be818cc9eec5aee6d52c05e",
"inchikey": "MOCMGXIPMROLCL-UHFFFAOYSA-N",
"smiles": "CN(c1cccc2cc(C(=O)NCC(C)(CCO)SCc3ccccc3)[nH]c12)S(=O)(=O)c1cccs1"
},
"smiles": "CN(c1cccc2cc(C(=O)NCC(C)(CCO)SCc3ccccc3)[nH]c12)S(=O)(=O)c1cccs1",
"reactionStepId": "sa_3266baf00c11955526e2cd08",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100144702A1;1409;894848\",\"rsmi\":\"O[C:7]([c:6]1[nH:5][c:4]2[c:3]([N:2]([CH3:1])[S:29](=[O:30])(=[O:31])[c:32]3[cH:33][cH:34][cH:35][s:36]3)[cH:28][cH:27][cH:26][c:25]2[cH:24]1)=[O:8].[NH2:9][CH2:10][C:11]([CH3:12])([CH2:13][CH2:14][OH:15])[S:16][CH2:17][c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1>CCN=C=NCCCN(C)C.CN(C)C=O.Cl.O.On1nnc2ccccc21>[CH3:1][N:2]([c:3]1[c:4]2[nH:5][c:6]([C:7](=[O:8])[NH:9][CH2:10][C:11]([CH3:12])([CH2:13][CH2:14][OH:15])[S:16][CH2:17][c:18]3[cH:19][cH:20][cH:21][cH:22][cH:23]3)[cH:24][c:25]2[cH:26][cH:27][cH:28]1)[S:29](=[O:30])(=[O:31])[c:32]1[cH:33][cH:34][cH:35][s:36]1\"},\"mapped_reaction_smiles\":\"O[C:7]([c:6]1[nH:5][c:4]2[c:3]([N:2]([CH3:1])[S:29](=[O:30])(=[O:31])[c:32]3[cH:33][cH:34][cH:35][s:36]3)[cH:28][cH:27][cH:26][c:25]2[cH:24]1)=[O:8].[NH2:9][CH2:10][C:11]([CH3:12])([CH2:13][CH2:14][OH:15])[S:16][CH2:17][c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1>CCN=C=NCCCN(C)C.CN(C)C=O.Cl.O.On1nnc2ccccc21>[CH3:1][N:2]([c:3]1[c:4]2[nH:5][c:6]([C:7](=[O:8])[NH:9][CH2:10][C:11]([CH3:12])([CH2:13][CH2:14][OH:15])[S:16][CH2:17][c:18]3[cH:19][cH:20][cH:21][cH:22][cH:23]3)[cH:24][c:25]2[cH:26][cH:27][cH:28]1)[S:29](=[O:30])(=[O:31])[c:32]1[cH:33][cH:34][cH:35][s:36]1\"}",
"reactionStep": {
"id": "sa_3266baf00c11955526e2cd08",
"reactionHash": "b70f717c3c962700d054fbac739db4ff4026c4f0aa8ae794e88f028554a8e2a6"
},
"children": [
{
"id": "10369",
"routeId": "sa_42dce7d0267dc2a59debf00a",
"moleculeId": "sa_7d49691ade6f3529387019e6",
"parentId": "10368",
"isLeaf": false,
"molecule": {
"id": "sa_7d49691ade6f3529387019e6",
"inchikey": "JVUQAAUCBJMCCL-UHFFFAOYSA-N",
"smiles": "CN(c1cccc2cc(C(=O)O)[nH]c12)S(=O)(=O)c1cccs1"
},
"smiles": "CN(c1cccc2cc(C(=O)O)[nH]c12)S(=O)(=O)c1cccs1",
"reactionStepId": "sa_bb2fafdd1ab14bd35d9f1a20",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100144702A1;1346;894831\",\"rsmi\":\"CC[O:9][C:7]([c:6]1[nH:5][c:4]2[c:3]([N:2]([CH3:1])[S:15](=[O:16])(=[O:17])[c:18]3[cH:19][cH:20][cH:21][s:22]3)[cH:14][cH:13][cH:12][c:11]2[cH:10]1)=[O:8]>C1CCOC1.CO.[Na+].O>[CH3:1][N:2]([c:3]1[c:4]2[nH:5][c:6]([C:7](=[O:8])[OH:9])[cH:10][c:11]2[cH:12][cH:13][cH:14]1)[S:15](=[O:16])(=[O:17])[c:18]1[cH:19][cH:20][cH:21][s:22]1\"},\"mapped_reaction_smiles\":\"CC[O:9][C:7]([c:6]1[nH:5][c:4]2[c:3]([N:2]([CH3:1])[S:15](=[O:16])(=[O:17])[c:18]3[cH:19][cH:20][cH:21][s:22]3)[cH:14][cH:13][cH:12][c:11]2[cH:10]1)=[O:8]>C1CCOC1.CO.[Na+].O>[CH3:1][N:2]([c:3]1[c:4]2[nH:5][c:6]([C:7](=[O:8])[OH:9])[cH:10][c:11]2[cH:12][cH:13][cH:14]1)[S:15](=[O:16])(=[O:17])[c:18]1[cH:19][cH:20][cH:21][s:22]1\"}",
"reactionStep": {
"id": "sa_bb2fafdd1ab14bd35d9f1a20",
"reactionHash": "af28a3415361c9e7a0a71cfa2e92212116dae29b520238eedf6dabda60e029f5"
},
"children": [
{
"id": "10370",
"routeId": "sa_42dce7d0267dc2a59debf00a",
"moleculeId": "sa_12f0343bd22cba2c566b7619",
"parentId": "10369",
"isLeaf": true,
"molecule": {
"id": "sa_12f0343bd22cba2c566b7619",
"inchikey": "PRWKOKDZZPWRTP-UHFFFAOYSA-N",
"smiles": "CCOC(=O)c1cc2cccc(N(C)S(=O)(=O)c3cccs3)c2[nH]1"
},
"smiles": "CCOC(=O)c1cc2cccc(N(C)S(=O)(=O)c3cccs3)c2[nH]1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "10371",
"routeId": "sa_42dce7d0267dc2a59debf00a",
"moleculeId": "sa_7aa004fdecd5e3c097ad388d",
"parentId": "10368",
"isLeaf": false,
"molecule": {
"id": "sa_7aa004fdecd5e3c097ad388d",
"inchikey": "NNXZHSDGAVBCEU-UHFFFAOYSA-N",
"smiles": "CC(CN)(CCO)SCc1ccccc1"
},
"smiles": "CC(CN)(CCO)SCc1ccccc1",
"reactionStepId": "sa_453d65f4cba211b5d235bdd6",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100144702A1;1406;894847\",\"rsmi\":\"O=[N+:4]([O-])[CH2:3][C:2]([CH3:1])([CH2:5][CH2:6][OH:7])[S:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1>C1CCOC1.CCO.O.[Al+3].[HH].[HH].[HH].[HH].[Li+]>[CH3:1][C:2]([CH2:3][NH2:4])([CH2:5][CH2:6][OH:7])[S:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1\"},\"mapped_reaction_smiles\":\"O=[N+:4]([O-])[CH2:3][C:2]([CH3:1])([CH2:5][CH2:6][OH:7])[S:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1>C1CCOC1.CCO.O.[Al+3].[HH].[HH].[HH].[HH].[Li+]>[CH3:1][C:2]([CH2:3][NH2:4])([CH2:5][CH2:6][OH:7])[S:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1\"}",
"reactionStep": {
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"reactionHash": "e16da396357e27b866cb83bd5394320fd5ca8df21be96b201c9b17f8848d6926"
},
"children": [
{
"id": "10372",
"routeId": "sa_42dce7d0267dc2a59debf00a",
"moleculeId": "sa_7ffe0483f1db07f6831bf948",
"parentId": "10371",
"isLeaf": true,
"molecule": {
"id": "sa_7ffe0483f1db07f6831bf948",
"inchikey": "AKYDRALIEYDLKR-UHFFFAOYSA-N",
"smiles": "CC(CCO)(C[N+](=O)[O-])SCc1ccccc1"
},
"smiles": "CC(CCO)(C[N+](=O)[O-])SCc1ccccc1",
"reactionStepId": null,
"template": null,
"metadata": null,
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"children": []
}
]
}
]
}
]
},
{
"id": "10373",
"routeId": "sa_42dce7d0267dc2a59debf00a",
"moleculeId": "sa_d2a31ea58046b00856f61ca5",
"parentId": "10366",
"isLeaf": true,
"molecule": {
"id": "sa_d2a31ea58046b00856f61ca5",
"inchikey": "QARBMVPHQWIHKH-UHFFFAOYSA-N",
"smiles": "CS(=O)(=O)Cl"
},
"smiles": "CS(=O)(=O)Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
}