Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CNC(=O)c1c2cc(C3CC3)c(N(CCCO)S(C)(=O)=O)cc2nn1-c1ccc(O)cc1
InChiKey
MHFBKOVCLNXVBK-UHFFFAOYSA-N
Route Signature
c11ba1747d9ba6b6899fdea335dc5d6b1916a5a0d8a2e46dbc6467f557076dbc
Synthesis route with 5 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_cd90775769d40c3cd365c03c",
"signature": "c11ba1747d9ba6b6899fdea335dc5d6b1916a5a0d8a2e46dbc6467f557076dbc",
"contentHash": "610fa86ab72923d94986f2740b0660669ad350cc0e97fc997e37b932363993d5",
"length": 5,
"isConvergent": false
},
"target": {
"id": "sa_7cb72c6fd3594fa840d2c298",
"benchmarkSetId": "61e696668b63e77d7c2a29c0821768e1c383de8313852d6e995224859494442e",
"targetId": "n5-01498",
"moleculeId": "sa_9fc12f444347caab7bef03af",
"smiles": "CNC(=O)c1c2cc(C3CC3)c(N(CCCO)S(C)(=O)=O)cc2nn1-c1ccc(O)cc1",
"routeLength": 5,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_9fc12f444347caab7bef03af",
"inchikey": "MHFBKOVCLNXVBK-UHFFFAOYSA-N",
"smiles": "CNC(=O)c1c2cc(C3CC3)c(N(CCCO)S(C)(=O)=O)cc2nn1-c1ccc(O)cc1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "14385",
"routeId": "sa_cd90775769d40c3cd365c03c",
"moleculeId": "sa_9fc12f444347caab7bef03af",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_9fc12f444347caab7bef03af",
"inchikey": "MHFBKOVCLNXVBK-UHFFFAOYSA-N",
"smiles": "CNC(=O)c1c2cc(C3CC3)c(N(CCCO)S(C)(=O)=O)cc2nn1-c1ccc(O)cc1"
},
"smiles": "CNC(=O)c1c2cc(C3CC3)c(N(CCCO)S(C)(=O)=O)cc2nn1-c1ccc(O)cc1",
"reactionStepId": "sa_8d535a3530bfa6994cd9c732",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20120142686A1;0292;1225436\",\"rsmi\":\"Br[c:29]1[cH:28][cH:27][c:26](-[n:25]2[c:5]([C:3]([NH:2][CH3:1])=[O:4])[c:6]3[cH:7][c:8]([CH:9]4[CH2:10][CH2:11]4)[c:12]([N:13]([CH2:14][CH2:15][CH2:16][OH:17])[S:18]([CH3:19])(=[O:20])=[O:21])[cH:22][c:23]3[n:24]2)[cH:32][cH:31]1.[OH2:30]>C1COCCO1.Cl.O.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.[K+].[Pd].[Pd]>[CH3:1][NH:2][C:3](=[O:4])[c:5]1[c:6]2[cH:7][c:8]([CH:9]3[CH2:10][CH2:11]3)[c:12]([N:13]([CH2:14][CH2:15][CH2:16][OH:17])[S:18]([CH3:19])(=[O:20])=[O:21])[cH:22][c:23]2[n:24][n:25]1-[c:26]1[cH:27][cH:28][c:29]([OH:30])[cH:31][cH:32]1\"},\"mapped_reaction_smiles\":\"Br[c:29]1[cH:28][cH:27][c:26](-[n:25]2[c:5]([C:3]([NH:2][CH3:1])=[O:4])[c:6]3[cH:7][c:8]([CH:9]4[CH2:10][CH2:11]4)[c:12]([N:13]([CH2:14][CH2:15][CH2:16][OH:17])[S:18]([CH3:19])(=[O:20])=[O:21])[cH:22][c:23]3[n:24]2)[cH:32][cH:31]1.[OH2:30]>C1COCCO1.Cl.O.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.[K+].[Pd].[Pd]>[CH3:1][NH:2][C:3](=[O:4])[c:5]1[c:6]2[cH:7][c:8]([CH:9]3[CH2:10][CH2:11]3)[c:12]([N:13]([CH2:14][CH2:15][CH2:16][OH:17])[S:18]([CH3:19])(=[O:20])=[O:21])[cH:22][c:23]2[n:24][n:25]1-[c:26]1[cH:27][cH:28][c:29]([OH:30])[cH:31][cH:32]1\"}",
"reactionStep": {
"id": "sa_8d535a3530bfa6994cd9c732",
"reactionHash": "d05527c3251cdcd908cf4f45db8ba1c210e886488fdfec1eacc7b012387a16f4"
},
"children": [
{
"id": "14386",
"routeId": "sa_cd90775769d40c3cd365c03c",
"moleculeId": "sa_106b35b8a76bbe73829a0a69",
"parentId": "14385",
"isLeaf": true,
"molecule": {
"id": "sa_106b35b8a76bbe73829a0a69",
"inchikey": "XLYOFNOQVPJJNP-UHFFFAOYSA-N",
"smiles": "O"
},
"smiles": "O",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "14387",
"routeId": "sa_cd90775769d40c3cd365c03c",
"moleculeId": "sa_37a6195b2d7dc9d867e819e2",
"parentId": "14385",
"isLeaf": false,
"molecule": {
"id": "sa_37a6195b2d7dc9d867e819e2",
"inchikey": "YKUQIUYIIZRUPH-UHFFFAOYSA-N",
"smiles": "CNC(=O)c1c2cc(C3CC3)c(N(CCCO)S(C)(=O)=O)cc2nn1-c1ccc(Br)cc1"
},
"smiles": "CNC(=O)c1c2cc(C3CC3)c(N(CCCO)S(C)(=O)=O)cc2nn1-c1ccc(Br)cc1",
"reactionStepId": "sa_e4713b7b40dff7c4bd755139",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20120142686A1;0274;1225433\",\"rsmi\":\"Br[CH2:14][CH2:15][CH2:16][OH:17].[CH3:1][NH:2][C:3](=[O:4])[c:5]1[c:6]2[cH:7][c:8]([CH:9]3[CH2:10][CH2:11]3)[c:12]([NH:13][S:18]([CH3:19])(=[O:20])=[O:21])[cH:22][c:23]2[n:24][n:25]1-[c:26]1[cH:27][cH:28][c:29]([Br:30])[cH:31][cH:32]1>CC#N.CCOC(C)=O.O=C(O)O.[K+].[K+]>[CH3:1][NH:2][C:3](=[O:4])[c:5]1[c:6]2[cH:7][c:8]([CH:9]3[CH2:10][CH2:11]3)[c:12]([N:13]([CH2:14][CH2:15][CH2:16][OH:17])[S:18]([CH3:19])(=[O:20])=[O:21])[cH:22][c:23]2[n:24][n:25]1-[c:26]1[cH:27][cH:28][c:29]([Br:30])[cH:31][cH:32]1\"},\"mapped_reaction_smiles\":\"Br[CH2:14][CH2:15][CH2:16][OH:17].[CH3:1][NH:2][C:3](=[O:4])[c:5]1[c:6]2[cH:7][c:8]([CH:9]3[CH2:10][CH2:11]3)[c:12]([NH:13][S:18]([CH3:19])(=[O:20])=[O:21])[cH:22][c:23]2[n:24][n:25]1-[c:26]1[cH:27][cH:28][c:29]([Br:30])[cH:31][cH:32]1>CC#N.CCOC(C)=O.O=C(O)O.[K+].[K+]>[CH3:1][NH:2][C:3](=[O:4])[c:5]1[c:6]2[cH:7][c:8]([CH:9]3[CH2:10][CH2:11]3)[c:12]([N:13]([CH2:14][CH2:15][CH2:16][OH:17])[S:18]([CH3:19])(=[O:20])=[O:21])[cH:22][c:23]2[n:24][n:25]1-[c:26]1[cH:27][cH:28][c:29]([Br:30])[cH:31][cH:32]1\"}",
"reactionStep": {
"id": "sa_e4713b7b40dff7c4bd755139",
"reactionHash": "afd0e1eb229fe979a870687e8a896291bcf8968b9bc9f5981a15c01a8e52681d"
},
"children": [
{
"id": "14388",
"routeId": "sa_cd90775769d40c3cd365c03c",
"moleculeId": "sa_bd92cae57d7cade894ca650a",
"parentId": "14387",
"isLeaf": false,
"molecule": {
"id": "sa_bd92cae57d7cade894ca650a",
"inchikey": "QFMJUNJVFSANCQ-UHFFFAOYSA-N",
"smiles": "CNC(=O)c1c2cc(C3CC3)c(NS(C)(=O)=O)cc2nn1-c1ccc(Br)cc1"
},
"smiles": "CNC(=O)c1c2cc(C3CC3)c(NS(C)(=O)=O)cc2nn1-c1ccc(Br)cc1",
"reactionStepId": "sa_74647630238d01605268cc73",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20120142686A1;0241;1225422\",\"rsmi\":\"Cl[S:14]([CH3:15])(=[O:16])=[O:17].[CH3:1][NH:2][C:3](=[O:4])[c:5]1[c:6]2[cH:7][c:8]([CH:9]3[CH2:10][CH2:11]3)[c:12]([NH2:13])[cH:18][c:19]2[n:20][n:21]1-[c:22]1[cH:23][cH:24][c:25]([Br:26])[cH:27][cH:28]1>CCN(C(C)C)C(C)C.CCO.Cl.ClCCl.[K+].O>[CH3:1][NH:2][C:3](=[O:4])[c:5]1[c:6]2[cH:7][c:8]([CH:9]3[CH2:10][CH2:11]3)[c:12]([NH:13][S:14]([CH3:15])(=[O:16])=[O:17])[cH:18][c:19]2[n:20][n:21]1-[c:22]1[cH:23][cH:24][c:25]([Br:26])[cH:27][cH:28]1\"},\"mapped_reaction_smiles\":\"Cl[S:14]([CH3:15])(=[O:16])=[O:17].[CH3:1][NH:2][C:3](=[O:4])[c:5]1[c:6]2[cH:7][c:8]([CH:9]3[CH2:10][CH2:11]3)[c:12]([NH2:13])[cH:18][c:19]2[n:20][n:21]1-[c:22]1[cH:23][cH:24][c:25]([Br:26])[cH:27][cH:28]1>CCN(C(C)C)C(C)C.CCO.Cl.ClCCl.[K+].O>[CH3:1][NH:2][C:3](=[O:4])[c:5]1[c:6]2[cH:7][c:8]([CH:9]3[CH2:10][CH2:11]3)[c:12]([NH:13][S:14]([CH3:15])(=[O:16])=[O:17])[cH:18][c:19]2[n:20][n:21]1-[c:22]1[cH:23][cH:24][c:25]([Br:26])[cH:27][cH:28]1\"}",
"reactionStep": {
"id": "sa_74647630238d01605268cc73",
"reactionHash": "a419fdf53e798faec666bafc0300a0b4808a0098bf4fde3236d0e16a8002038a"
},
"children": [
{
"id": "14389",
"routeId": "sa_cd90775769d40c3cd365c03c",
"moleculeId": "sa_34d12978add9bdc92d543676",
"parentId": "14388",
"isLeaf": false,
"molecule": {
"id": "sa_34d12978add9bdc92d543676",
"inchikey": "ATYMWMUFMVRUAS-UHFFFAOYSA-N",
"smiles": "CNC(=O)c1c2cc(C3CC3)c(N)cc2nn1-c1ccc(Br)cc1"
},
"smiles": "CNC(=O)c1c2cc(C3CC3)c(N)cc2nn1-c1ccc(Br)cc1",
"reactionStepId": "sa_89f6caf023646b9c39ec1c77",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20120142686A1;0240;1225421\",\"rsmi\":\"O=[N+:13]([O-])[c:12]1[c:8]([CH:9]2[CH2:10][CH2:11]2)[cH:7][c:6]2[c:5]([C:3]([NH:2][CH3:1])=[O:4])[n:17](-[c:18]3[cH:19][cH:20][c:21]([Br:22])[cH:23][cH:24]3)[n:16][c:15]2[cH:14]1>CCO.CO.ClCCl.O.Cl.[Fe].N>[CH3:1][NH:2][C:3](=[O:4])[c:5]1[c:6]2[cH:7][c:8]([CH:9]3[CH2:10][CH2:11]3)[c:12]([NH2:13])[cH:14][c:15]2[n:16][n:17]1-[c:18]1[cH:19][cH:20][c:21]([Br:22])[cH:23][cH:24]1\"},\"mapped_reaction_smiles\":\"O=[N+:13]([O-])[c:12]1[c:8]([CH:9]2[CH2:10][CH2:11]2)[cH:7][c:6]2[c:5]([C:3]([NH:2][CH3:1])=[O:4])[n:17](-[c:18]3[cH:19][cH:20][c:21]([Br:22])[cH:23][cH:24]3)[n:16][c:15]2[cH:14]1>CCO.CO.ClCCl.O.Cl.[Fe].N>[CH3:1][NH:2][C:3](=[O:4])[c:5]1[c:6]2[cH:7][c:8]([CH:9]3[CH2:10][CH2:11]3)[c:12]([NH2:13])[cH:14][c:15]2[n:16][n:17]1-[c:18]1[cH:19][cH:20][c:21]([Br:22])[cH:23][cH:24]1\"}",
"reactionStep": {
"id": "sa_89f6caf023646b9c39ec1c77",
"reactionHash": "27ea2cfc607b84e755e8e56f054c88ee895ca77106a82ff692a947db00e4625e"
},
"children": [
{
"id": "14390",
"routeId": "sa_cd90775769d40c3cd365c03c",
"moleculeId": "sa_02f97cae49c7384c41cf7e2d",
"parentId": "14389",
"isLeaf": false,
"molecule": {
"id": "sa_02f97cae49c7384c41cf7e2d",
"inchikey": "TVMRARIHPAIHNM-UHFFFAOYSA-N",
"smiles": "CNC(=O)c1c2cc(C3CC3)c([N+](=O)[O-])cc2nn1-c1ccc(Br)cc1"
},
"smiles": "CNC(=O)c1c2cc(C3CC3)c([N+](=O)[O-])cc2nn1-c1ccc(Br)cc1",
"reactionStepId": "sa_a1d7ef46518b775c01224d0e",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20120142686A1;0239;1225420\",\"rsmi\":\"O[C:3](=[O:4])[c:5]1[c:6]2[cH:7][c:8]([CH:9]3[CH2:10][CH2:11]3)[c:12]([N+:13](=[O:14])[O-:15])[cH:16][c:17]2[n:18][n:19]1-[c:20]1[cH:21][cH:22][c:23]([Br:24])[cH:25][cH:26]1.[CH3:1][NH2:2]>O=P(Cl)(Cl)Cl.c1ccncc1>[CH3:1][NH:2][C:3](=[O:4])[c:5]1[c:6]2[cH:7][c:8]([CH:9]3[CH2:10][CH2:11]3)[c:12]([N+:13](=[O:14])[O-:15])[cH:16][c:17]2[n:18][n:19]1-[c:20]1[cH:21][cH:22][c:23]([Br:24])[cH:25][cH:26]1\"},\"mapped_reaction_smiles\":\"O[C:3](=[O:4])[c:5]1[c:6]2[cH:7][c:8]([CH:9]3[CH2:10][CH2:11]3)[c:12]([N+:13](=[O:14])[O-:15])[cH:16][c:17]2[n:18][n:19]1-[c:20]1[cH:21][cH:22][c:23]([Br:24])[cH:25][cH:26]1.[CH3:1][NH2:2]>O=P(Cl)(Cl)Cl.c1ccncc1>[CH3:1][NH:2][C:3](=[O:4])[c:5]1[c:6]2[cH:7][c:8]([CH:9]3[CH2:10][CH2:11]3)[c:12]([N+:13](=[O:14])[O-:15])[cH:16][c:17]2[n:18][n:19]1-[c:20]1[cH:21][cH:22][c:23]([Br:24])[cH:25][cH:26]1\"}",
"reactionStep": {
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"reactionHash": "1cbbfcce3af2317916f733dd8a43400feb0b51928b2f9ba3bf564abb4a8d30a6"
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"children": [
{
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"routeId": "sa_cd90775769d40c3cd365c03c",
"moleculeId": "sa_e00cdbb7fb9d3ecf114a19d3",
"parentId": "14390",
"isLeaf": true,
"molecule": {
"id": "sa_e00cdbb7fb9d3ecf114a19d3",
"inchikey": "BAVYZALUXZFZLV-UHFFFAOYSA-N",
"smiles": "CN"
},
"smiles": "CN",
"reactionStepId": null,
"template": null,
"metadata": null,
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"children": []
},
{
"id": "14392",
"routeId": "sa_cd90775769d40c3cd365c03c",
"moleculeId": "sa_8649d6ecaf0522336156a292",
"parentId": "14390",
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"molecule": {
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"inchikey": "PBWOWHPUIDXSNG-UHFFFAOYSA-N",
"smiles": "O=C(O)c1c2cc(C3CC3)c([N+](=O)[O-])cc2nn1-c1ccc(Br)cc1"
},
"smiles": "O=C(O)c1c2cc(C3CC3)c([N+](=O)[O-])cc2nn1-c1ccc(Br)cc1",
"reactionStepId": null,
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}
]
}
]
},
{
"id": "14393",
"routeId": "sa_cd90775769d40c3cd365c03c",
"moleculeId": "sa_d2a31ea58046b00856f61ca5",
"parentId": "14388",
"isLeaf": true,
"molecule": {
"id": "sa_d2a31ea58046b00856f61ca5",
"inchikey": "QARBMVPHQWIHKH-UHFFFAOYSA-N",
"smiles": "CS(=O)(=O)Cl"
},
"smiles": "CS(=O)(=O)Cl",
"reactionStepId": null,
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}
]
},
{
"id": "14394",
"routeId": "sa_cd90775769d40c3cd365c03c",
"moleculeId": "sa_4e0739973446652372900716",
"parentId": "14387",
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"molecule": {
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"inchikey": "RQFUZUMFPRMVDX-UHFFFAOYSA-N",
"smiles": "OCCCBr"
},
"smiles": "OCCCBr",
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"children": []
}
]
}
]
}
}