Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
C[C@@H]1CN(c2ccc(Nc3cc(Br)cn(C)c3=O)nc2)CCN1C
InChiKey
NOENKIAZRYIWGJ-GFCCVEGCSA-N
Route Signature
65b7ed5cba4316d48974747daaac7b896438635d1cacdb0a8688cf25ff39a082
Synthesis route with 5 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_3c4c66efd762e70df80ff25b",
"signature": "65b7ed5cba4316d48974747daaac7b896438635d1cacdb0a8688cf25ff39a082",
"contentHash": "0ed2e1907a3aaffa6ffbeac64c818f6867d0c67df55f75668579f925703d4a89",
"length": 5,
"isConvergent": false
},
"target": {
"id": "sa_8d4d90ab5723be2ddae13e2e",
"benchmarkSetId": "61e696668b63e77d7c2a29c0821768e1c383de8313852d6e995224859494442e",
"targetId": "n5-04000",
"moleculeId": "sa_c3760e93bacdaf68075289ca",
"smiles": "C[C@@H]1CN(c2ccc(Nc3cc(Br)cn(C)c3=O)nc2)CCN1C",
"routeLength": 5,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_c3760e93bacdaf68075289ca",
"inchikey": "NOENKIAZRYIWGJ-GFCCVEGCSA-N",
"smiles": "C[C@@H]1CN(c2ccc(Nc3cc(Br)cn(C)c3=O)nc2)CCN1C"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "15332",
"routeId": "sa_3c4c66efd762e70df80ff25b",
"moleculeId": "sa_c3760e93bacdaf68075289ca",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_c3760e93bacdaf68075289ca",
"inchikey": "NOENKIAZRYIWGJ-GFCCVEGCSA-N",
"smiles": "C[C@@H]1CN(c2ccc(Nc3cc(Br)cn(C)c3=O)nc2)CCN1C"
},
"smiles": "C[C@@H]1CN(c2ccc(Nc3cc(Br)cn(C)c3=O)nc2)CCN1C",
"reactionStepId": "sa_007a7643e5ff6f4e157d49e2",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130116245A1;0275;1364827\",\"rsmi\":\"O=[CH2:24].[CH3:1][C@@H:2]1[CH2:3][N:4]([c:5]2[cH:6][n:7][c:8]([NH:9][c:10]3[cH:11][c:12]([Br:13])[cH:14][n:15]([CH3:16])[c:17]3=[O:18])[cH:19][cH:20]2)[CH2:21][CH2:22][NH:23]1>CC(=O)O.CC(=O)OB(OC(C)=O)OC(C)=O.CO.O.[Na+]>[CH3:1][C@@H:2]1[CH2:3][N:4]([c:5]2[cH:6][n:7][c:8]([NH:9][c:10]3[cH:11][c:12]([Br:13])[cH:14][n:15]([CH3:16])[c:17]3=[O:18])[cH:19][cH:20]2)[CH2:21][CH2:22][N:23]1[CH3:24]\"},\"mapped_reaction_smiles\":\"O=[CH2:24].[CH3:1][C@@H:2]1[CH2:3][N:4]([c:5]2[cH:6][n:7][c:8]([NH:9][c:10]3[cH:11][c:12]([Br:13])[cH:14][n:15]([CH3:16])[c:17]3=[O:18])[cH:19][cH:20]2)[CH2:21][CH2:22][NH:23]1>CC(=O)O.CC(=O)OB(OC(C)=O)OC(C)=O.CO.O.[Na+]>[CH3:1][C@@H:2]1[CH2:3][N:4]([c:5]2[cH:6][n:7][c:8]([NH:9][c:10]3[cH:11][c:12]([Br:13])[cH:14][n:15]([CH3:16])[c:17]3=[O:18])[cH:19][cH:20]2)[CH2:21][CH2:22][N:23]1[CH3:24]\"}",
"reactionStep": {
"id": "sa_007a7643e5ff6f4e157d49e2",
"reactionHash": "2c093a5bd860e228625216d64ff9bee25ddeeac25c13dc1096e8245ca42b2ae0"
},
"children": [
{
"id": "15333",
"routeId": "sa_3c4c66efd762e70df80ff25b",
"moleculeId": "sa_4d617ea62afddd9f73a9bcc9",
"parentId": "15332",
"isLeaf": false,
"molecule": {
"id": "sa_4d617ea62afddd9f73a9bcc9",
"inchikey": "MLXUKGZFJKPPPG-LLVKDONJSA-N",
"smiles": "C[C@@H]1CN(c2ccc(Nc3cc(Br)cn(C)c3=O)nc2)CCN1"
},
"smiles": "C[C@@H]1CN(c2ccc(Nc3cc(Br)cn(C)c3=O)nc2)CCN1",
"reactionStepId": "sa_a1f3504070d3795b92249854",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130116245A1;0274;1364826\",\"rsmi\":\"CC(C)(C)OC(=O)[N:23]1[C@H:2]([CH3:1])[CH2:3][N:4]([c:5]2[cH:6][n:7][c:8]([NH:9][c:10]3[cH:11][c:12]([Br:13])[cH:14][n:15]([CH3:16])[c:17]3=[O:18])[cH:19][cH:20]2)[CH2:21][CH2:22]1>ClCCl.O=C(O)C(F)(F)F.[Na+].O>[CH3:1][C@@H:2]1[CH2:3][N:4]([c:5]2[cH:6][n:7][c:8]([NH:9][c:10]3[cH:11][c:12]([Br:13])[cH:14][n:15]([CH3:16])[c:17]3=[O:18])[cH:19][cH:20]2)[CH2:21][CH2:22][NH:23]1\"},\"mapped_reaction_smiles\":\"CC(C)(C)OC(=O)[N:23]1[C@H:2]([CH3:1])[CH2:3][N:4]([c:5]2[cH:6][n:7][c:8]([NH:9][c:10]3[cH:11][c:12]([Br:13])[cH:14][n:15]([CH3:16])[c:17]3=[O:18])[cH:19][cH:20]2)[CH2:21][CH2:22]1>ClCCl.O=C(O)C(F)(F)F.[Na+].O>[CH3:1][C@@H:2]1[CH2:3][N:4]([c:5]2[cH:6][n:7][c:8]([NH:9][c:10]3[cH:11][c:12]([Br:13])[cH:14][n:15]([CH3:16])[c:17]3=[O:18])[cH:19][cH:20]2)[CH2:21][CH2:22][NH:23]1\"}",
"reactionStep": {
"id": "sa_a1f3504070d3795b92249854",
"reactionHash": "ae3e6549e8bc5ca4796b8ef2b9a8cbb92617597c34a5354db63fbacdb11c6450"
},
"children": [
{
"id": "15334",
"routeId": "sa_3c4c66efd762e70df80ff25b",
"moleculeId": "sa_5dbf3179a0404b2ece2b3831",
"parentId": "15333",
"isLeaf": false,
"molecule": {
"id": "sa_5dbf3179a0404b2ece2b3831",
"inchikey": "HFRFOIBEYUFDLG-CQSZACIVSA-N",
"smiles": "C[C@@H]1CN(c2ccc(Nc3cc(Br)cn(C)c3=O)nc2)CCN1C(=O)OC(C)(C)C"
},
"smiles": "C[C@@H]1CN(c2ccc(Nc3cc(Br)cn(C)c3=O)nc2)CCN1C(=O)OC(C)(C)C",
"reactionStepId": "sa_6ca91ebc7bafd2846b969c7f",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130116245A1;0273;1364825\",\"rsmi\":\"Br[c:10]1[cH:11][c:12]([Br:13])[cH:14][n:15]([CH3:16])[c:17]1=[O:18].[CH3:1][C@@H:2]1[CH2:3][N:4]([c:5]2[cH:6][cH:7][c:8]([NH2:9])[n:19][cH:20]2)[CH2:21][CH2:22][N:23]1[C:24](=[O:25])[O:26][C:27]([CH3:28])([CH3:29])[CH3:30]>C1COCCO1.CC1(C)c2cccc(P(c3ccccc3)c3ccccc3)c2Oc2c(P(c3ccccc3)c3ccccc3)cccc21.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(O)O.[Cs+].[Cs+].[Pd].[Pd]>[CH3:1][C@@H:2]1[CH2:3][N:4]([c:5]2[cH:6][cH:7][c:8]([NH:9][c:10]3[cH:11][c:12]([Br:13])[cH:14][n:15]([CH3:16])[c:17]3=[O:18])[n:19][cH:20]2)[CH2:21][CH2:22][N:23]1[C:24](=[O:25])[O:26][C:27]([CH3:28])([CH3:29])[CH3:30]\"},\"mapped_reaction_smiles\":\"Br[c:10]1[cH:11][c:12]([Br:13])[cH:14][n:15]([CH3:16])[c:17]1=[O:18].[CH3:1][C@@H:2]1[CH2:3][N:4]([c:5]2[cH:6][cH:7][c:8]([NH2:9])[n:19][cH:20]2)[CH2:21][CH2:22][N:23]1[C:24](=[O:25])[O:26][C:27]([CH3:28])([CH3:29])[CH3:30]>C1COCCO1.CC1(C)c2cccc(P(c3ccccc3)c3ccccc3)c2Oc2c(P(c3ccccc3)c3ccccc3)cccc21.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(O)O.[Cs+].[Cs+].[Pd].[Pd]>[CH3:1][C@@H:2]1[CH2:3][N:4]([c:5]2[cH:6][cH:7][c:8]([NH:9][c:10]3[cH:11][c:12]([Br:13])[cH:14][n:15]([CH3:16])[c:17]3=[O:18])[n:19][cH:20]2)[CH2:21][CH2:22][N:23]1[C:24](=[O:25])[O:26][C:27]([CH3:28])([CH3:29])[CH3:30]\"}",
"reactionStep": {
"id": "sa_6ca91ebc7bafd2846b969c7f",
"reactionHash": "b5aefd215612910d54280cb064b8241706e32e5087ed3ab1bcd808351355158a"
},
"children": [
{
"id": "15335",
"routeId": "sa_3c4c66efd762e70df80ff25b",
"moleculeId": "sa_0da4787b25c92654c400a908",
"parentId": "15334",
"isLeaf": true,
"molecule": {
"id": "sa_0da4787b25c92654c400a908",
"inchikey": "AOJAJTJZSBVNPU-UHFFFAOYSA-N",
"smiles": "Cn1cc(Br)cc(Br)c1=O"
},
"smiles": "Cn1cc(Br)cc(Br)c1=O",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "15336",
"routeId": "sa_3c4c66efd762e70df80ff25b",
"moleculeId": "sa_2191c0f5bd90d002d8e1f0fc",
"parentId": "15334",
"isLeaf": false,
"molecule": {
"id": "sa_2191c0f5bd90d002d8e1f0fc",
"inchikey": "QPHUAFJMBHMUMT-LLVKDONJSA-N",
"smiles": "C[C@@H]1CN(c2ccc(N)nc2)CCN1C(=O)OC(C)(C)C"
},
"smiles": "C[C@@H]1CN(c2ccc(N)nc2)CCN1C(=O)OC(C)(C)C",
"reactionStepId": "sa_a636aec0c659f8ea2b8bb222",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130116245A1;0272;1364824\",\"rsmi\":\"O=[N+:9]([O-])[c:8]1[cH:7][cH:6][c:5]([N:4]2[CH2:3][C@@H:2]([CH3:1])[N:14]([C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21])[CH2:13][CH2:12]2)[cH:11][n:10]1>C.CO.[H][H].[Pd]>[CH3:1][C@@H:2]1[CH2:3][N:4]([c:5]2[cH:6][cH:7][c:8]([NH2:9])[n:10][cH:11]2)[CH2:12][CH2:13][N:14]1[C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21]\"},\"mapped_reaction_smiles\":\"O=[N+:9]([O-])[c:8]1[cH:7][cH:6][c:5]([N:4]2[CH2:3][C@@H:2]([CH3:1])[N:14]([C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21])[CH2:13][CH2:12]2)[cH:11][n:10]1>C.CO.[H][H].[Pd]>[CH3:1][C@@H:2]1[CH2:3][N:4]([c:5]2[cH:6][cH:7][c:8]([NH2:9])[n:10][cH:11]2)[CH2:12][CH2:13][N:14]1[C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21]\"}",
"reactionStep": {
"id": "sa_a636aec0c659f8ea2b8bb222",
"reactionHash": "428bc3ff58ca1c64be6ba137fbe61e0273825a387c267c569ad5a29038704a70"
},
"children": [
{
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"routeId": "sa_3c4c66efd762e70df80ff25b",
"moleculeId": "sa_0f79c5ff63de6f20c25e8111",
"parentId": "15336",
"isLeaf": false,
"molecule": {
"id": "sa_0f79c5ff63de6f20c25e8111",
"inchikey": "XONXLUBFVDTACE-LLVKDONJSA-N",
"smiles": "C[C@@H]1CN(c2ccc([N+](=O)[O-])nc2)CCN1C(=O)OC(C)(C)C"
},
"smiles": "C[C@@H]1CN(c2ccc([N+](=O)[O-])nc2)CCN1C(=O)OC(C)(C)C",
"reactionStepId": "sa_1b7dca2ae193b526e6e10884",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130116245A1;0271;1364823\",\"rsmi\":\"Br[c:5]1[cH:6][cH:7][c:8]([N+:9](=[O:10])[O-:11])[n:12][cH:13]1.[CH3:1][C@@H:2]1[CH2:3][NH:4][CH2:14][CH2:15][N:16]1[C:17](=[O:18])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23]>CS(C)=O.O=C(O)O.[K+].[K+]>[CH3:1][C@@H:2]1[CH2:3][N:4]([c:5]2[cH:6][cH:7][c:8]([N+:9](=[O:10])[O-:11])[n:12][cH:13]2)[CH2:14][CH2:15][N:16]1[C:17](=[O:18])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23]\"},\"mapped_reaction_smiles\":\"Br[c:5]1[cH:6][cH:7][c:8]([N+:9](=[O:10])[O-:11])[n:12][cH:13]1.[CH3:1][C@@H:2]1[CH2:3][NH:4][CH2:14][CH2:15][N:16]1[C:17](=[O:18])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23]>CS(C)=O.O=C(O)O.[K+].[K+]>[CH3:1][C@@H:2]1[CH2:3][N:4]([c:5]2[cH:6][cH:7][c:8]([N+:9](=[O:10])[O-:11])[n:12][cH:13]2)[CH2:14][CH2:15][N:16]1[C:17](=[O:18])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23]\"}",
"reactionStep": {
"id": "sa_1b7dca2ae193b526e6e10884",
"reactionHash": "367eae402285ecf22b66851f236ae2d42eecca24e60afd5d37b1ce080cefabc7"
},
"children": [
{
"id": "15338",
"routeId": "sa_3c4c66efd762e70df80ff25b",
"moleculeId": "sa_34d3d65ad37c90ce30aa5a69",
"parentId": "15337",
"isLeaf": true,
"molecule": {
"id": "sa_34d3d65ad37c90ce30aa5a69",
"inchikey": "ATXXLNCPVSUCNK-UHFFFAOYSA-N",
"smiles": "O=[N+]([O-])c1ccc(Br)cn1"
},
"smiles": "O=[N+]([O-])c1ccc(Br)cn1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "15339",
"routeId": "sa_3c4c66efd762e70df80ff25b",
"moleculeId": "sa_a1c984761aa2331ef3e2c17a",
"parentId": "15337",
"isLeaf": true,
"molecule": {
"id": "sa_a1c984761aa2331ef3e2c17a",
"inchikey": "DATRVIMZZZVHMP-MRVPVSSYSA-N",
"smiles": "C[C@@H]1CNCCN1C(=O)OC(C)(C)C"
},
"smiles": "C[C@@H]1CNCCN1C(=O)OC(C)(C)C",
"reactionStepId": null,
"template": null,
"metadata": null,
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}
]
}
]
}
]
}
]
},
{
"id": "15340",
"routeId": "sa_3c4c66efd762e70df80ff25b",
"moleculeId": "sa_fa48b0311f9ecb906b2132fe",
"parentId": "15332",
"isLeaf": true,
"molecule": {
"id": "sa_fa48b0311f9ecb906b2132fe",
"inchikey": "WSFSSNUMVMOOMR-UHFFFAOYSA-N",
"smiles": "C=O"
},
"smiles": "C=O",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
}