Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
Nc1ccc(N2CCCCC2)cc1-c1cc(Oc2cccc(C(F)(F)F)c2)ncn1
InChiKey
HCRVPPQATMJHIF-UHFFFAOYSA-N
Route Signature
c95a95b81ab3fe979b8be95f9efa291798d8a19af77538003c8c22567c0bb774
Synthesis route with 5 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_8414d3b06e7eb900e847e5fd",
"signature": "c95a95b81ab3fe979b8be95f9efa291798d8a19af77538003c8c22567c0bb774",
"contentHash": "82e1958e7f8abad599af3ac9db04d7e68ac894e769904a99174984e19746f7c0",
"length": 5,
"isConvergent": false
},
"target": {
"id": "sa_abd40aff0c9de71a8070eaa1",
"benchmarkSetId": "61e696668b63e77d7c2a29c0821768e1c383de8313852d6e995224859494442e",
"targetId": "n5-00722",
"moleculeId": "sa_00ecc5bcf660523068e7fbb8",
"smiles": "Nc1ccc(N2CCCCC2)cc1-c1cc(Oc2cccc(C(F)(F)F)c2)ncn1",
"routeLength": 5,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_00ecc5bcf660523068e7fbb8",
"inchikey": "HCRVPPQATMJHIF-UHFFFAOYSA-N",
"smiles": "Nc1ccc(N2CCCCC2)cc1-c1cc(Oc2cccc(C(F)(F)F)c2)ncn1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "13739",
"routeId": "sa_8414d3b06e7eb900e847e5fd",
"moleculeId": "sa_00ecc5bcf660523068e7fbb8",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_00ecc5bcf660523068e7fbb8",
"inchikey": "HCRVPPQATMJHIF-UHFFFAOYSA-N",
"smiles": "Nc1ccc(N2CCCCC2)cc1-c1cc(Oc2cccc(C(F)(F)F)c2)ncn1"
},
"smiles": "Nc1ccc(N2CCCCC2)cc1-c1cc(Oc2cccc(C(F)(F)F)c2)ncn1",
"reactionStepId": "sa_b9b1c325f5446bcc2947a65d",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08916569B2;0326;1557042\",\"rsmi\":\"O=[N+:1]([O-])[c:2]1[c:3](-[c:4]2[n:5][cH:6][n:7][c:8]([O:9][c:10]3[cH:11][c:12]([C:13]([F:14])([F:15])[F:16])[cH:17][cH:18][cH:19]3)[cH:20]2)[cH:21][c:22]([N:23]2[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]2)[cH:29][cH:30]1>CCOC(C)=O.CO.[Pd]>[NH2:1][c:2]1[c:3](-[c:4]2[n:5][cH:6][n:7][c:8]([O:9][c:10]3[cH:11][c:12]([C:13]([F:14])([F:15])[F:16])[cH:17][cH:18][cH:19]3)[cH:20]2)[cH:21][c:22]([N:23]2[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]2)[cH:29][cH:30]1\"},\"mapped_reaction_smiles\":\"O=[N+:1]([O-])[c:2]1[c:3](-[c:4]2[n:5][cH:6][n:7][c:8]([O:9][c:10]3[cH:11][c:12]([C:13]([F:14])([F:15])[F:16])[cH:17][cH:18][cH:19]3)[cH:20]2)[cH:21][c:22]([N:23]2[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]2)[cH:29][cH:30]1>CCOC(C)=O.CO.[Pd]>[NH2:1][c:2]1[c:3](-[c:4]2[n:5][cH:6][n:7][c:8]([O:9][c:10]3[cH:11][c:12]([C:13]([F:14])([F:15])[F:16])[cH:17][cH:18][cH:19]3)[cH:20]2)[cH:21][c:22]([N:23]2[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]2)[cH:29][cH:30]1\"}",
"reactionStep": {
"id": "sa_b9b1c325f5446bcc2947a65d",
"reactionHash": "27ef176e4a73aed65a0ce25d65a5fb856a5f0f81c236ec8e448cb848cd400dda"
},
"children": [
{
"id": "13740",
"routeId": "sa_8414d3b06e7eb900e847e5fd",
"moleculeId": "sa_81b4668a19dd00123f878787",
"parentId": "13739",
"isLeaf": false,
"molecule": {
"id": "sa_81b4668a19dd00123f878787",
"inchikey": "CLTSVKVSIXWULE-UHFFFAOYSA-N",
"smiles": "O=[N+]([O-])c1ccc(N2CCCCC2)cc1-c1cc(Oc2cccc(C(F)(F)F)c2)ncn1"
},
"smiles": "O=[N+]([O-])c1ccc(N2CCCCC2)cc1-c1cc(Oc2cccc(C(F)(F)F)c2)ncn1",
"reactionStepId": "sa_5137970acbfff0d30e297b57",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08916569B2;0325;1557041\",\"rsmi\":\"Cl[c:10]1[n:9][cH:8][n:7][c:6](-[c:5]2[c:4]([N+:2](=[O:1])[O-:3])[cH:32][cH:31][c:24]([N:25]3[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]3)[cH:23]2)[cH:22]1.[OH:11][c:12]1[cH:13][c:14]([C:15]([F:16])([F:17])[F:18])[cH:19][cH:20][cH:21]1>CN(C)C=O.O=C(O)O.[K+].[K+]>[O:1]=[N+:2]([O-:3])[c:4]1[c:5](-[c:6]2[n:7][cH:8][n:9][c:10]([O:11][c:12]3[cH:13][c:14]([C:15]([F:16])([F:17])[F:18])[cH:19][cH:20][cH:21]3)[cH:22]2)[cH:23][c:24]([N:25]2[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]2)[cH:31][cH:32]1\"},\"mapped_reaction_smiles\":\"Cl[c:10]1[n:9][cH:8][n:7][c:6](-[c:5]2[c:4]([N+:2](=[O:1])[O-:3])[cH:32][cH:31][c:24]([N:25]3[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]3)[cH:23]2)[cH:22]1.[OH:11][c:12]1[cH:13][c:14]([C:15]([F:16])([F:17])[F:18])[cH:19][cH:20][cH:21]1>CN(C)C=O.O=C(O)O.[K+].[K+]>[O:1]=[N+:2]([O-:3])[c:4]1[c:5](-[c:6]2[n:7][cH:8][n:9][c:10]([O:11][c:12]3[cH:13][c:14]([C:15]([F:16])([F:17])[F:18])[cH:19][cH:20][cH:21]3)[cH:22]2)[cH:23][c:24]([N:25]2[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]2)[cH:31][cH:32]1\"}",
"reactionStep": {
"id": "sa_5137970acbfff0d30e297b57",
"reactionHash": "2c6831ce46733850b5a20f73af26a63d2187d2872972048322a1759a18cce14a"
},
"children": [
{
"id": "13741",
"routeId": "sa_8414d3b06e7eb900e847e5fd",
"moleculeId": "sa_b84c6189c56aa7c3d36227c8",
"parentId": "13740",
"isLeaf": false,
"molecule": {
"id": "sa_b84c6189c56aa7c3d36227c8",
"inchikey": "HGKIGMYVUWNGRQ-UHFFFAOYSA-N",
"smiles": "O=[N+]([O-])c1ccc(N2CCCCC2)cc1-c1cc(Cl)ncn1"
},
"smiles": "O=[N+]([O-])c1ccc(N2CCCCC2)cc1-c1cc(Cl)ncn1",
"reactionStepId": "sa_905a279c3b4eb7179c1f0257",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08916569B2;0299;1557032\",\"rsmi\":\"CC1(C)OB([c:5]2[c:4]([N+:2](=[O:1])[O-:3])[cH:22][cH:21][c:14]([N:15]3[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]3)[cH:13]2)OC1(C)C.Cl[c:6]1[cH:7][c:8]([Cl:9])[n:10][cH:11][n:12]1>C1COCCO1.Cl[Pd](Cl)([PH](c1ccccc1)(c1ccccc1)c1ccccc1)[PH](c1ccccc1)(c1ccccc1)c1ccccc1.O.O=P(O)(O)O.[K+].[K+].[K+].c1ccc([As](c2ccccc2)c2ccccc2)cc1>[O:1]=[N+:2]([O-:3])[c:4]1[c:5](-[c:6]2[cH:7][c:8]([Cl:9])[n:10][cH:11][n:12]2)[cH:13][c:14]([N:15]2[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]2)[cH:21][cH:22]1\"},\"mapped_reaction_smiles\":\"CC1(C)OB([c:5]2[c:4]([N+:2](=[O:1])[O-:3])[cH:22][cH:21][c:14]([N:15]3[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]3)[cH:13]2)OC1(C)C.Cl[c:6]1[cH:7][c:8]([Cl:9])[n:10][cH:11][n:12]1>C1COCCO1.Cl[Pd](Cl)([PH](c1ccccc1)(c1ccccc1)c1ccccc1)[PH](c1ccccc1)(c1ccccc1)c1ccccc1.O.O=P(O)(O)O.[K+].[K+].[K+].c1ccc([As](c2ccccc2)c2ccccc2)cc1>[O:1]=[N+:2]([O-:3])[c:4]1[c:5](-[c:6]2[cH:7][c:8]([Cl:9])[n:10][cH:11][n:12]2)[cH:13][c:14]([N:15]2[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]2)[cH:21][cH:22]1\"}",
"reactionStep": {
"id": "sa_905a279c3b4eb7179c1f0257",
"reactionHash": "d4c2297fa3140b5d6ac4445fa2b006bf097c4fbaac0f59c0db7f9859d8395422"
},
"children": [
{
"id": "13742",
"routeId": "sa_8414d3b06e7eb900e847e5fd",
"moleculeId": "sa_7ea6d525159f20d1bb52d777",
"parentId": "13741",
"isLeaf": false,
"molecule": {
"id": "sa_7ea6d525159f20d1bb52d777",
"inchikey": "ATOXGVCTPWNKTK-UHFFFAOYSA-N",
"smiles": "CC1(C)OB(c2cc(N3CCCCC3)ccc2[N+](=O)[O-])OC1(C)C"
},
"smiles": "CC1(C)OB(c2cc(N3CCCCC3)ccc2[N+](=O)[O-])OC1(C)C",
"reactionStepId": "sa_80e8976807c83d0a56b38cd6",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08916569B2;0279;1557021\",\"rsmi\":\"Br[c:6]1[c:7]([N+:8](=[O:9])[O-:10])[cH:11][cH:12][c:13]([N:14]2[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]2)[cH:20]1.CC1(C)OB([B:5]2[O:4][C:2]([CH3:1])([CH3:3])[C:22]([CH3:23])([CH3:24])[O:21]2)OC1(C)C>CC(=O)O.CS(C)=O.Cl[Pd]Cl.[Fe+2].[K+]>[CH3:1][C:2]1([CH3:3])[O:4][B:5]([c:6]2[c:7]([N+:8](=[O:9])[O-:10])[cH:11][cH:12][c:13]([N:14]3[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]3)[cH:20]2)[O:21][C:22]1([CH3:23])[CH3:24]\"},\"mapped_reaction_smiles\":\"Br[c:6]1[c:7]([N+:8](=[O:9])[O-:10])[cH:11][cH:12][c:13]([N:14]2[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]2)[cH:20]1.CC1(C)OB([B:5]2[O:4][C:2]([CH3:1])([CH3:3])[C:22]([CH3:23])([CH3:24])[O:21]2)OC1(C)C>CC(=O)O.CS(C)=O.Cl[Pd]Cl.[Fe+2].[K+]>[CH3:1][C:2]1([CH3:3])[O:4][B:5]([c:6]2[c:7]([N+:8](=[O:9])[O-:10])[cH:11][cH:12][c:13]([N:14]3[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]3)[cH:20]2)[O:21][C:22]1([CH3:23])[CH3:24]\"}",
"reactionStep": {
"id": "sa_80e8976807c83d0a56b38cd6",
"reactionHash": "aa0ba27d58abcc7440df6ad36f4790483c17af0058b8ce213d28048019fc7e3e"
},
"children": [
{
"id": "13743",
"routeId": "sa_8414d3b06e7eb900e847e5fd",
"moleculeId": "sa_8b6bb60ea37a04c336145afa",
"parentId": "13742",
"isLeaf": false,
"molecule": {
"id": "sa_8b6bb60ea37a04c336145afa",
"inchikey": "IFPALIOJOQUXQY-UHFFFAOYSA-N",
"smiles": "O=[N+]([O-])c1ccc(N2CCCCC2)cc1Br"
},
"smiles": "O=[N+]([O-])c1ccc(N2CCCCC2)cc1Br",
"reactionStepId": "sa_9887a9ec9918fc100bb81b29",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08916569B2;0278;1557020\",\"rsmi\":\"F[c:8]1[cH:7][c:5]([Br:6])[c:4]([N+:2](=[O:1])[O-:3])[cH:16][cH:15]1.[NH:9]1[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]1>CN(C)C=O.O=C(O)O.[K+].[K+]>[O:1]=[N+:2]([O-:3])[c:4]1[c:5]([Br:6])[cH:7][c:8]([N:9]2[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]2)[cH:15][cH:16]1\"},\"mapped_reaction_smiles\":\"F[c:8]1[cH:7][c:5]([Br:6])[c:4]([N+:2](=[O:1])[O-:3])[cH:16][cH:15]1.[NH:9]1[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]1>CN(C)C=O.O=C(O)O.[K+].[K+]>[O:1]=[N+:2]([O-:3])[c:4]1[c:5]([Br:6])[cH:7][c:8]([N:9]2[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]2)[cH:15][cH:16]1\"}",
"reactionStep": {
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"reactionHash": "85c78bfcfc864df7e73e7d9184ed0ebfc90944014de343e8c37f9b6b9af0f83b"
},
"children": [
{
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"routeId": "sa_8414d3b06e7eb900e847e5fd",
"moleculeId": "sa_60b03dbd902de8f42159b182",
"parentId": "13743",
"isLeaf": true,
"molecule": {
"id": "sa_60b03dbd902de8f42159b182",
"inchikey": "NQRYJNQNLNOLGT-UHFFFAOYSA-N",
"smiles": "C1CCNCC1"
},
"smiles": "C1CCNCC1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "13745",
"routeId": "sa_8414d3b06e7eb900e847e5fd",
"moleculeId": "sa_00f13ce0aa60a53df3808b4e",
"parentId": "13743",
"isLeaf": true,
"molecule": {
"id": "sa_00f13ce0aa60a53df3808b4e",
"inchikey": "VGYVBEJDXIPSDL-UHFFFAOYSA-N",
"smiles": "O=[N+]([O-])c1ccc(F)cc1Br"
},
"smiles": "O=[N+]([O-])c1ccc(F)cc1Br",
"reactionStepId": null,
"template": null,
"metadata": null,
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}
]
},
{
"id": "13746",
"routeId": "sa_8414d3b06e7eb900e847e5fd",
"moleculeId": "sa_e6c301388ac142801d4af5a2",
"parentId": "13742",
"isLeaf": true,
"molecule": {
"id": "sa_e6c301388ac142801d4af5a2",
"inchikey": "IPWKHHSGDUIRAH-UHFFFAOYSA-N",
"smiles": "CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C"
},
"smiles": "CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C",
"reactionStepId": null,
"template": null,
"metadata": null,
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"children": []
}
]
},
{
"id": "13747",
"routeId": "sa_8414d3b06e7eb900e847e5fd",
"moleculeId": "sa_db8aea1103296dc9b89dfb68",
"parentId": "13741",
"isLeaf": true,
"molecule": {
"id": "sa_db8aea1103296dc9b89dfb68",
"inchikey": "XJPZKYIHCLDXST-UHFFFAOYSA-N",
"smiles": "Clc1cc(Cl)ncn1"
},
"smiles": "Clc1cc(Cl)ncn1",
"reactionStepId": null,
"template": null,
"metadata": null,
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}
]
},
{
"id": "13748",
"routeId": "sa_8414d3b06e7eb900e847e5fd",
"moleculeId": "sa_f958ecea5b547e7ad4183276",
"parentId": "13740",
"isLeaf": true,
"molecule": {
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"inchikey": "UGEJOEBBMPOJMT-UHFFFAOYSA-N",
"smiles": "Oc1cccc(C(F)(F)F)c1"
},
"smiles": "Oc1cccc(C(F)(F)F)c1",
"reactionStepId": null,
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}
]
}
]
}
}