Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
COC(=O)c1cc2[nH]c(C)nc2c(F)c1Nc1ccccc1
InChiKey
VORQDDJASUDHDO-UHFFFAOYSA-N
Route Signature
363899e404bcdfca31ae7a8e3e3f2fa94405bf25d2eee154448d9171f1e0a918
Synthesis route with 6 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_5932153736d11258818703b5",
"signature": "363899e404bcdfca31ae7a8e3e3f2fa94405bf25d2eee154448d9171f1e0a918",
"contentHash": "b20559244b1908c04c4ecd19b93c75f4a8474b5a3607bc74f2509b1b6b468c3a",
"length": 6,
"isConvergent": false
},
"target": {
"id": "sa_10d040d325683434355b3c35",
"benchmarkSetId": "61e696668b63e77d7c2a29c0821768e1c383de8313852d6e995224859494442e",
"targetId": "n5-00314",
"moleculeId": "sa_00cbaf4d7ac81d3c08410301",
"smiles": "COC(=O)c1cc2[nH]c(C)nc2c(F)c1Nc1ccccc1",
"routeLength": 6,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_00cbaf4d7ac81d3c08410301",
"inchikey": "VORQDDJASUDHDO-UHFFFAOYSA-N",
"smiles": "COC(=O)c1cc2[nH]c(C)nc2c(F)c1Nc1ccccc1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "3955",
"routeId": "sa_5932153736d11258818703b5",
"moleculeId": "sa_00cbaf4d7ac81d3c08410301",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_00cbaf4d7ac81d3c08410301",
"inchikey": "VORQDDJASUDHDO-UHFFFAOYSA-N",
"smiles": "COC(=O)c1cc2[nH]c(C)nc2c(F)c1Nc1ccccc1"
},
"smiles": "COC(=O)c1cc2[nH]c(C)nc2c(F)c1Nc1ccccc1",
"reactionStepId": "sa_bf19ec65c0620e3e7aa2eaf3",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20110158971A1;0288;1074470\",\"rsmi\":\"CC(=O)C[C:10](=O)[CH3:11].[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([NH2:12])[c:8]([NH2:9])[c:13]([F:14])[c:15]1[NH:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1>CCO.Cl.O=C(O)O.[Na+]>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]2[c:8]([n:9][c:10]([CH3:11])[nH:12]2)[c:13]([F:14])[c:15]1[NH:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1\"},\"mapped_reaction_smiles\":\"CC(=O)C[C:10](=O)[CH3:11].[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([NH2:12])[c:8]([NH2:9])[c:13]([F:14])[c:15]1[NH:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1>CCO.Cl.O=C(O)O.[Na+]>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]2[c:8]([n:9][c:10]([CH3:11])[nH:12]2)[c:13]([F:14])[c:15]1[NH:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1\"}",
"reactionStep": {
"id": "sa_bf19ec65c0620e3e7aa2eaf3",
"reactionHash": "54e67639631e0da00cc606c91fcfb6a567bc7cee15aa11b5d0d6fc46a7764c53"
},
"children": [
{
"id": "3956",
"routeId": "sa_5932153736d11258818703b5",
"moleculeId": "sa_250d03c7cf2b1f9514c2fa60",
"parentId": "3955",
"isLeaf": false,
"molecule": {
"id": "sa_250d03c7cf2b1f9514c2fa60",
"inchikey": "JHIJEIVUKKHRAU-UHFFFAOYSA-N",
"smiles": "COC(=O)c1cc(N)c(N)c(F)c1Nc1ccccc1"
},
"smiles": "COC(=O)c1cc(N)c(N)c(F)c1Nc1ccccc1",
"reactionStepId": "sa_cfa5c48e0696711874df7097",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20110158971A1;0287;1074469\",\"rsmi\":\"O=[N+:19]([O-])[c:18]1[c:16]([NH2:17])[c:14]([F:15])[c:6]([NH:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:20]1>CCO.O=CO.N.O.O.[Pd+2]>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([NH:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[c:14]([F:15])[c:16]([NH2:17])[c:18]([NH2:19])[cH:20]1\"},\"mapped_reaction_smiles\":\"O=[N+:19]([O-])[c:18]1[c:16]([NH2:17])[c:14]([F:15])[c:6]([NH:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:20]1>CCO.O=CO.N.O.O.[Pd+2]>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([NH:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[c:14]([F:15])[c:16]([NH2:17])[c:18]([NH2:19])[cH:20]1\"}",
"reactionStep": {
"id": "sa_cfa5c48e0696711874df7097",
"reactionHash": "ac698630cf0496c14a3d49fed93ef023d6b67811cf1d3cd0bc8c5651938f0e8e"
},
"children": [
{
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"parentId": "3956",
"isLeaf": false,
"molecule": {
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"inchikey": "JQUIVIJMSGIEPL-UHFFFAOYSA-N",
"smiles": "COC(=O)c1cc([N+](=O)[O-])c(N)c(F)c1Nc1ccccc1"
},
"smiles": "COC(=O)c1cc([N+](=O)[O-])c(N)c(F)c1Nc1ccccc1",
"reactionStepId": "sa_470a2daab701c89e6f60f1b9",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20110158971A1;0132;1074394\",\"rsmi\":\"F[c:6]1[c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:22][c:18]([N+:19](=[O:20])[O-:21])[c:16]([NH2:17])[c:14]1[F:15].[NH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([NH:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[c:14]([F:15])[c:16]([NH2:17])[c:18]([N+:19](=[O:20])[O-:21])[cH:22]1\"},\"mapped_reaction_smiles\":\"F[c:6]1[c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:22][c:18]([N+:19](=[O:20])[O-:21])[c:16]([NH2:17])[c:14]1[F:15].[NH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([NH:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[c:14]([F:15])[c:16]([NH2:17])[c:18]([N+:19](=[O:20])[O-:21])[cH:22]1\"}",
"reactionStep": {
"id": "sa_470a2daab701c89e6f60f1b9",
"reactionHash": "6bfb2e97416312896a6c1fddfad6b3bb4c27d84a858d101073993cd891210a55"
},
"children": [
{
"id": "3958",
"routeId": "sa_5932153736d11258818703b5",
"moleculeId": "sa_938c30d45cd30675586b6c75",
"parentId": "3957",
"isLeaf": false,
"molecule": {
"id": "sa_938c30d45cd30675586b6c75",
"inchikey": "HOJFIOHGPQOQBF-UHFFFAOYSA-N",
"smiles": "COC(=O)c1cc([N+](=O)[O-])c(N)c(F)c1F"
},
"smiles": "COC(=O)c1cc([N+](=O)[O-])c(N)c(F)c1F",
"reactionStepId": "sa_177b133c23ac0c921e1b955f",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20110158971A1;0124;1074388\",\"rsmi\":\"O[CH3:1].[OH:2][C:3](=[O:4])[c:5]1[c:6]([F:7])[c:8]([F:9])[c:10]([NH2:11])[c:12]([N+:13](=[O:14])[O-:15])[cH:16]1>C1CCOC1.C[Si](C)(C)C=[N+]=[N-]>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([F:7])[c:8]([F:9])[c:10]([NH2:11])[c:12]([N+:13](=[O:14])[O-:15])[cH:16]1\"},\"mapped_reaction_smiles\":\"O[CH3:1].[OH:2][C:3](=[O:4])[c:5]1[c:6]([F:7])[c:8]([F:9])[c:10]([NH2:11])[c:12]([N+:13](=[O:14])[O-:15])[cH:16]1>C1CCOC1.C[Si](C)(C)C=[N+]=[N-]>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([F:7])[c:8]([F:9])[c:10]([NH2:11])[c:12]([N+:13](=[O:14])[O-:15])[cH:16]1\"}",
"reactionStep": {
"id": "sa_177b133c23ac0c921e1b955f",
"reactionHash": "104bc811e116f2243cff361e452b5573208dad44673dd3971a528fcefbd4503d"
},
"children": [
{
"id": "3959",
"routeId": "sa_5932153736d11258818703b5",
"moleculeId": "sa_061a3efbe4d30c2cc87d48e7",
"parentId": "3958",
"isLeaf": true,
"molecule": {
"id": "sa_061a3efbe4d30c2cc87d48e7",
"inchikey": "OKKJLVBELUTLKV-UHFFFAOYSA-N",
"smiles": "CO"
},
"smiles": "CO",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "3960",
"routeId": "sa_5932153736d11258818703b5",
"moleculeId": "sa_7104afdf01471b988ff4bffd",
"parentId": "3958",
"isLeaf": false,
"molecule": {
"id": "sa_7104afdf01471b988ff4bffd",
"inchikey": "WXXHOWQPFHXRDY-UHFFFAOYSA-N",
"smiles": "Nc1c([N+](=O)[O-])cc(C(=O)O)c(F)c1F"
},
"smiles": "Nc1c([N+](=O)[O-])cc(C(=O)O)c(F)c1F",
"reactionStepId": "sa_b0802aca59932593db710636",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20110158971A1;0123;1074387\",\"rsmi\":\"F[c:2]1[c:3]([F:4])[c:5]([F:6])[c:7]([C:8](=[O:9])[OH:10])[cH:11][c:12]1[N+:13](=[O:14])[O-:15].[NH3:1]>Cl.O.O>[NH2:1][c:2]1[c:3]([F:4])[c:5]([F:6])[c:7]([C:8](=[O:9])[OH:10])[cH:11][c:12]1[N+:13](=[O:14])[O-:15]\"},\"mapped_reaction_smiles\":\"F[c:2]1[c:3]([F:4])[c:5]([F:6])[c:7]([C:8](=[O:9])[OH:10])[cH:11][c:12]1[N+:13](=[O:14])[O-:15].[NH3:1]>Cl.O.O>[NH2:1][c:2]1[c:3]([F:4])[c:5]([F:6])[c:7]([C:8](=[O:9])[OH:10])[cH:11][c:12]1[N+:13](=[O:14])[O-:15]\"}",
"reactionStep": {
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"reactionHash": "74dfb36ff0fc11b83b80d1989f16da99c3cd9776b2a5af4b2fa6c6e3b76a6b88"
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"children": [
{
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"moleculeId": "sa_b252aed91150aa28d7f5ffee",
"parentId": "3960",
"isLeaf": false,
"molecule": {
"id": "sa_b252aed91150aa28d7f5ffee",
"inchikey": "BCMIOBTWFPSPJJ-UHFFFAOYSA-N",
"smiles": "O=C(O)c1cc([N+](=O)[O-])c(F)c(F)c1F"
},
"smiles": "O=C(O)c1cc([N+](=O)[O-])c(F)c(F)c1F",
"reactionStepId": "sa_05e00f6278eb6717c61b5e6e",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20110158971A1;0122;1074386\",\"rsmi\":\"O[N+:12](=[O:13])[O-:14].[O:1]=[C:2]([OH:3])[c:4]1[c:5]([F:6])[c:7]([F:8])[c:9]([F:10])[cH:11][cH:15]1>O=S(=O)(O)O>[O:1]=[C:2]([OH:3])[c:4]1[c:5]([F:6])[c:7]([F:8])[c:9]([F:10])[c:11]([N+:12](=[O:13])[O-:14])[cH:15]1\"},\"mapped_reaction_smiles\":\"O[N+:12](=[O:13])[O-:14].[O:1]=[C:2]([OH:3])[c:4]1[c:5]([F:6])[c:7]([F:8])[c:9]([F:10])[cH:11][cH:15]1>O=S(=O)(O)O>[O:1]=[C:2]([OH:3])[c:4]1[c:5]([F:6])[c:7]([F:8])[c:9]([F:10])[c:11]([N+:12](=[O:13])[O-:14])[cH:15]1\"}",
"reactionStep": {
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"reactionHash": "7bffd338e0ae3dfab9f603caebea226593961566883a05a3c8e399d6b8dda445"
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"children": [
{
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"routeId": "sa_5932153736d11258818703b5",
"moleculeId": "sa_edac0a7fd043198784a28dd9",
"parentId": "3961",
"isLeaf": true,
"molecule": {
"id": "sa_edac0a7fd043198784a28dd9",
"inchikey": "GRYLNZFGIOXLOG-UHFFFAOYSA-N",
"smiles": "O=[N+]([O-])O"
},
"smiles": "O=[N+]([O-])O",
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"metadata": null,
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},
{
"id": "3963",
"routeId": "sa_5932153736d11258818703b5",
"moleculeId": "sa_fd70c0b48f8faa0dcccb80fc",
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"molecule": {
"id": "sa_fd70c0b48f8faa0dcccb80fc",
"inchikey": "WEPXLRANFJEOFZ-UHFFFAOYSA-N",
"smiles": "O=C(O)c1ccc(F)c(F)c1F"
},
"smiles": "O=C(O)c1ccc(F)c(F)c1F",
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}
]
},
{
"id": "3964",
"routeId": "sa_5932153736d11258818703b5",
"moleculeId": "sa_c9679fdd876f32f86b77fb69",
"parentId": "3960",
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"molecule": {
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"inchikey": "QGZKDVFQNNGYKY-UHFFFAOYSA-N",
"smiles": "N"
},
"smiles": "N",
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}
]
}
]
},
{
"id": "3965",
"routeId": "sa_5932153736d11258818703b5",
"moleculeId": "sa_257ba819b453f9a0e7fa3c07",
"parentId": "3957",
"isLeaf": true,
"molecule": {
"id": "sa_257ba819b453f9a0e7fa3c07",
"inchikey": "PAYRUJLWNCNPSJ-UHFFFAOYSA-N",
"smiles": "Nc1ccccc1"
},
"smiles": "Nc1ccccc1",
"reactionStepId": null,
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}
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]
},
{
"id": "3966",
"routeId": "sa_5932153736d11258818703b5",
"moleculeId": "sa_c916231dbcddaeebcd145de4",
"parentId": "3955",
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"molecule": {
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"inchikey": "YRKCREAYFQTBPV-UHFFFAOYSA-N",
"smiles": "CC(=O)CC(C)=O"
},
"smiles": "CC(=O)CC(C)=O",
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]
}
}