Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
O=C(NCC(=O)N1CCN(C(=O)c2ccccc2C(F)(F)F)CC1)c1ccc(-c2ccccc2)nc1
InChiKey
YHMKRCRJQPGZDJ-UHFFFAOYSA-N
Route Signature
5d3a3e2794614aa2b38ba6ddbefbc159e054e87e70872bb4e91964bd5bf0ef4e
Synthesis route with 5 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_b2291dadbc562f887fc8991b",
"signature": "5d3a3e2794614aa2b38ba6ddbefbc159e054e87e70872bb4e91964bd5bf0ef4e",
"contentHash": "ba8540b1695ad9b7265effc7f86cd5f5dd9a6a1e0fb308f534697484d6cf3f2a",
"length": 5,
"isConvergent": true
},
"target": {
"id": "sa_c99e0010c10b688a21cc378b",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-01467",
"moleculeId": "sa_058e6a014b43d98423f700a6",
"smiles": "O=C(NCC(=O)N1CCN(C(=O)c2ccccc2C(F)(F)F)CC1)c1ccc(-c2ccccc2)nc1",
"routeLength": 5,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_058e6a014b43d98423f700a6",
"inchikey": "YHMKRCRJQPGZDJ-UHFFFAOYSA-N",
"smiles": "O=C(NCC(=O)N1CCN(C(=O)c2ccccc2C(F)(F)F)CC1)c1ccc(-c2ccccc2)nc1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "10210",
"routeId": "sa_b2291dadbc562f887fc8991b",
"moleculeId": "sa_058e6a014b43d98423f700a6",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_058e6a014b43d98423f700a6",
"inchikey": "YHMKRCRJQPGZDJ-UHFFFAOYSA-N",
"smiles": "O=C(NCC(=O)N1CCN(C(=O)c2ccccc2C(F)(F)F)CC1)c1ccc(-c2ccccc2)nc1"
},
"smiles": "O=C(NCC(=O)N1CCN(C(=O)c2ccccc2C(F)(F)F)CC1)c1ccc(-c2ccccc2)nc1",
"reactionStepId": "sa_4a3c2b53565c2c8dbb3d5c98",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20110046134A1;0820;1019959\",\"rsmi\":\"O[C:2](=[O:1])[c:25]1[cH:26][n:27][c:28](-[c:29]2[cH:30][cH:31][cH:32][cH:33][cH:34]2)[cH:35][cH:36]1.[NH2:3][CH2:4][C:5](=[O:6])[N:7]1[CH2:8][CH2:9][N:10]([C:11](=[O:12])[c:13]2[c:14]([C:15]([F:16])([F:17])[F:18])[cH:19][cH:20][cH:21][cH:22]2)[CH2:23][CH2:24]1>CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C.CN(C)C=O.Cl.O.O=C(O)C(F)(F)F.On1nnc2ccccc21>[O:1]=[C:2]([NH:3][CH2:4][C:5](=[O:6])[N:7]1[CH2:8][CH2:9][N:10]([C:11](=[O:12])[c:13]2[c:14]([C:15]([F:16])([F:17])[F:18])[cH:19][cH:20][cH:21][cH:22]2)[CH2:23][CH2:24]1)[c:25]1[cH:26][n:27][c:28](-[c:29]2[cH:30][cH:31][cH:32][cH:33][cH:34]2)[cH:35][cH:36]1\"},\"mapped_reaction_smiles\":\"O[C:2](=[O:1])[c:25]1[cH:26][n:27][c:28](-[c:29]2[cH:30][cH:31][cH:32][cH:33][cH:34]2)[cH:35][cH:36]1.[NH2:3][CH2:4][C:5](=[O:6])[N:7]1[CH2:8][CH2:9][N:10]([C:11](=[O:12])[c:13]2[c:14]([C:15]([F:16])([F:17])[F:18])[cH:19][cH:20][cH:21][cH:22]2)[CH2:23][CH2:24]1>CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C.CN(C)C=O.Cl.O.O=C(O)C(F)(F)F.On1nnc2ccccc21>[O:1]=[C:2]([NH:3][CH2:4][C:5](=[O:6])[N:7]1[CH2:8][CH2:9][N:10]([C:11](=[O:12])[c:13]2[c:14]([C:15]([F:16])([F:17])[F:18])[cH:19][cH:20][cH:21][cH:22]2)[CH2:23][CH2:24]1)[c:25]1[cH:26][n:27][c:28](-[c:29]2[cH:30][cH:31][cH:32][cH:33][cH:34]2)[cH:35][cH:36]1\"}",
"reactionStep": {
"id": "sa_4a3c2b53565c2c8dbb3d5c98",
"reactionHash": "347dc0ab8d48962e05244a379be595ca5d3b72c85d58cd03816daaf5eaa824cf"
},
"children": [
{
"id": "10211",
"routeId": "sa_b2291dadbc562f887fc8991b",
"moleculeId": "sa_9d9f825d78ab2f7d7361052e",
"parentId": "10210",
"isLeaf": false,
"molecule": {
"id": "sa_9d9f825d78ab2f7d7361052e",
"inchikey": "DLFLQXUYRFIFOK-UHFFFAOYSA-N",
"smiles": "O=C(O)c1ccc(-c2ccccc2)nc1"
},
"smiles": "O=C(O)c1ccc(-c2ccccc2)nc1",
"reactionStepId": "sa_92870a8e3782a9304c5dc6f6",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20110046134A1;0818;1019958\",\"rsmi\":\"CC[O:3][C:2](=[O:1])[c:4]1[cH:5][n:6][c:7](-[c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[cH:14][cH:15]1>C1CCOC1.CO.O.[Li+].O>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][n:6][c:7](-[c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[cH:14][cH:15]1\"},\"mapped_reaction_smiles\":\"CC[O:3][C:2](=[O:1])[c:4]1[cH:5][n:6][c:7](-[c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[cH:14][cH:15]1>C1CCOC1.CO.O.[Li+].O>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][n:6][c:7](-[c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[cH:14][cH:15]1\"}",
"reactionStep": {
"id": "sa_92870a8e3782a9304c5dc6f6",
"reactionHash": "6525bc0c6a75c85a675974edf0128a19220f866b3357a3e01284ffe96ca05825"
},
"children": [
{
"id": "10212",
"routeId": "sa_b2291dadbc562f887fc8991b",
"moleculeId": "sa_821ba7003c49624bd462700c",
"parentId": "10211",
"isLeaf": true,
"molecule": {
"id": "sa_821ba7003c49624bd462700c",
"inchikey": "IKHQUQSZIPLOLJ-UHFFFAOYSA-N",
"smiles": "CCOC(=O)c1ccc(-c2ccccc2)nc1"
},
"smiles": "CCOC(=O)c1ccc(-c2ccccc2)nc1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "10213",
"routeId": "sa_b2291dadbc562f887fc8991b",
"moleculeId": "sa_f182c4e207c11fb47f52258b",
"parentId": "10210",
"isLeaf": false,
"molecule": {
"id": "sa_f182c4e207c11fb47f52258b",
"inchikey": "JRIXDMMDGMDEBG-UHFFFAOYSA-N",
"smiles": "NCC(=O)N1CCN(C(=O)c2ccccc2C(F)(F)F)CC1"
},
"smiles": "NCC(=O)N1CCN(C(=O)c2ccccc2C(F)(F)F)CC1",
"reactionStepId": "sa_d86d2a4ece8c6cbca45ebc94",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20110046134A1;0598;1019861\",\"rsmi\":\"CC(C)(C)OC(=O)[NH:1][CH2:2][C:3](=[O:4])[N:5]1[CH2:6][CH2:7][N:8]([C:9](=[O:10])[c:11]2[c:12]([C:13]([F:14])([F:15])[F:16])[cH:17][cH:18][cH:19][cH:20]2)[CH2:21][CH2:22]1>ClCCl.O=C(O)C(F)(F)F>[NH2:1][CH2:2][C:3](=[O:4])[N:5]1[CH2:6][CH2:7][N:8]([C:9](=[O:10])[c:11]2[c:12]([C:13]([F:14])([F:15])[F:16])[cH:17][cH:18][cH:19][cH:20]2)[CH2:21][CH2:22]1\"},\"mapped_reaction_smiles\":\"CC(C)(C)OC(=O)[NH:1][CH2:2][C:3](=[O:4])[N:5]1[CH2:6][CH2:7][N:8]([C:9](=[O:10])[c:11]2[c:12]([C:13]([F:14])([F:15])[F:16])[cH:17][cH:18][cH:19][cH:20]2)[CH2:21][CH2:22]1>ClCCl.O=C(O)C(F)(F)F>[NH2:1][CH2:2][C:3](=[O:4])[N:5]1[CH2:6][CH2:7][N:8]([C:9](=[O:10])[c:11]2[c:12]([C:13]([F:14])([F:15])[F:16])[cH:17][cH:18][cH:19][cH:20]2)[CH2:21][CH2:22]1\"}",
"reactionStep": {
"id": "sa_d86d2a4ece8c6cbca45ebc94",
"reactionHash": "e2d2b1f6da2bd956751e0fcc7b8e314ddd0ec9e1d9b0f9440c8e40a3232ef330"
},
"children": [
{
"id": "10214",
"routeId": "sa_b2291dadbc562f887fc8991b",
"moleculeId": "sa_3bd62e825285da91a2c73c91",
"parentId": "10213",
"isLeaf": false,
"molecule": {
"id": "sa_3bd62e825285da91a2c73c91",
"inchikey": "BQJJJXIMVMPTKN-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)NCC(=O)N1CCN(C(=O)c2ccccc2C(F)(F)F)CC1"
},
"smiles": "CC(C)(C)OC(=O)NCC(=O)N1CCN(C(=O)c2ccccc2C(F)(F)F)CC1",
"reactionStepId": "sa_f02f0b6530ada1aa01a40509",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20110046134A1;0596;1019860\",\"rsmi\":\"O[C:10]([CH2:9][NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])=[O:11].[NH:12]1[CH2:13][CH2:14][N:15]([C:16](=[O:17])[c:18]2[c:19]([C:20]([F:21])([F:22])[F:23])[cH:24][cH:25][cH:26][cH:27]2)[CH2:28][CH2:29]1>CCCCCC.CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C.CN(C)C=O.Cl.O.On1nnc2ccccc21>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][C:10](=[O:11])[N:12]1[CH2:13][CH2:14][N:15]([C:16](=[O:17])[c:18]2[c:19]([C:20]([F:21])([F:22])[F:23])[cH:24][cH:25][cH:26][cH:27]2)[CH2:28][CH2:29]1\"},\"mapped_reaction_smiles\":\"O[C:10]([CH2:9][NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])=[O:11].[NH:12]1[CH2:13][CH2:14][N:15]([C:16](=[O:17])[c:18]2[c:19]([C:20]([F:21])([F:22])[F:23])[cH:24][cH:25][cH:26][cH:27]2)[CH2:28][CH2:29]1>CCCCCC.CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C.CN(C)C=O.Cl.O.On1nnc2ccccc21>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][C:10](=[O:11])[N:12]1[CH2:13][CH2:14][N:15]([C:16](=[O:17])[c:18]2[c:19]([C:20]([F:21])([F:22])[F:23])[cH:24][cH:25][cH:26][cH:27]2)[CH2:28][CH2:29]1\"}",
"reactionStep": {
"id": "sa_f02f0b6530ada1aa01a40509",
"reactionHash": "ad2617562fd51290f2d938456fcb5b3009a3c84e3dfca933f7acbde4e7d260f7"
},
"children": [
{
"id": "10215",
"routeId": "sa_b2291dadbc562f887fc8991b",
"moleculeId": "sa_3145e652aca055303532b7c1",
"parentId": "10214",
"isLeaf": false,
"molecule": {
"id": "sa_3145e652aca055303532b7c1",
"inchikey": "VDWDAGOWIJYIGH-UHFFFAOYSA-N",
"smiles": "O=C(c1ccccc1C(F)(F)F)N1CCNCC1"
},
"smiles": "O=C(c1ccccc1C(F)(F)F)N1CCNCC1",
"reactionStepId": "sa_488e1c9589bdfead2c0022d5",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20110046134A1;0592;1019858\",\"rsmi\":\"c1ccc(C[N:16]2[CH2:15][CH2:14][N:13]([C:2](=[O:1])[c:3]3[c:4]([C:5]([F:6])([F:7])[F:8])[cH:9][cH:10][cH:11][cH:12]3)[CH2:18][CH2:17]2)cc1>CO.O=CO.N.[Pd]>[O:1]=[C:2]([c:3]1[c:4]([C:5]([F:6])([F:7])[F:8])[cH:9][cH:10][cH:11][cH:12]1)[N:13]1[CH2:14][CH2:15][NH:16][CH2:17][CH2:18]1\"},\"mapped_reaction_smiles\":\"c1ccc(C[N:16]2[CH2:15][CH2:14][N:13]([C:2](=[O:1])[c:3]3[c:4]([C:5]([F:6])([F:7])[F:8])[cH:9][cH:10][cH:11][cH:12]3)[CH2:18][CH2:17]2)cc1>CO.O=CO.N.[Pd]>[O:1]=[C:2]([c:3]1[c:4]([C:5]([F:6])([F:7])[F:8])[cH:9][cH:10][cH:11][cH:12]1)[N:13]1[CH2:14][CH2:15][NH:16][CH2:17][CH2:18]1\"}",
"reactionStep": {
"id": "sa_488e1c9589bdfead2c0022d5",
"reactionHash": "86032c2b83aec664dc3e7cfd3d00a79c9eb1bbd0f9a1ef006a9f9735eddd3ab9"
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"children": [
{
"id": "10216",
"routeId": "sa_b2291dadbc562f887fc8991b",
"moleculeId": "sa_8fce2322ea3c5747121cec21",
"parentId": "10215",
"isLeaf": false,
"molecule": {
"id": "sa_8fce2322ea3c5747121cec21",
"inchikey": "UOJHYVAKORDOHD-UHFFFAOYSA-N",
"smiles": "O=C(c1ccccc1C(F)(F)F)N1CCN(Cc2ccccc2)CC1"
},
"smiles": "O=C(c1ccccc1C(F)(F)F)N1CCN(Cc2ccccc2)CC1",
"reactionStepId": "sa_0d827fe30d383246856a71f9",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20110046134A1;0590;1019857\",\"rsmi\":\"O[C:2](=[O:1])[c:3]1[c:4]([C:5]([F:6])([F:7])[F:8])[cH:9][cH:10][cH:11][cH:12]1.[NH:13]1[CH2:14][CH2:15][N:16]([CH2:17][c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)[CH2:24][CH2:25]1>CCCCCC.CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C.CN(C)C=O.O.On1nnc2ccccc21>[O:1]=[C:2]([c:3]1[c:4]([C:5]([F:6])([F:7])[F:8])[cH:9][cH:10][cH:11][cH:12]1)[N:13]1[CH2:14][CH2:15][N:16]([CH2:17][c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)[CH2:24][CH2:25]1\"},\"mapped_reaction_smiles\":\"O[C:2](=[O:1])[c:3]1[c:4]([C:5]([F:6])([F:7])[F:8])[cH:9][cH:10][cH:11][cH:12]1.[NH:13]1[CH2:14][CH2:15][N:16]([CH2:17][c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)[CH2:24][CH2:25]1>CCCCCC.CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C.CN(C)C=O.O.On1nnc2ccccc21>[O:1]=[C:2]([c:3]1[c:4]([C:5]([F:6])([F:7])[F:8])[cH:9][cH:10][cH:11][cH:12]1)[N:13]1[CH2:14][CH2:15][N:16]([CH2:17][c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)[CH2:24][CH2:25]1\"}",
"reactionStep": {
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"reactionHash": "b62660f457ddd45771eba14841cbd56082adbaad272181559353b353d7f12654"
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"children": [
{
"id": "10217",
"routeId": "sa_b2291dadbc562f887fc8991b",
"moleculeId": "sa_cd06f02fa75558355030e8a1",
"parentId": "10216",
"isLeaf": true,
"molecule": {
"id": "sa_cd06f02fa75558355030e8a1",
"inchikey": "FBRJYBGLCHWYOE-UHFFFAOYSA-N",
"smiles": "O=C(O)c1ccccc1C(F)(F)F"
},
"smiles": "O=C(O)c1ccccc1C(F)(F)F",
"reactionStepId": null,
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},
{
"id": "10218",
"routeId": "sa_b2291dadbc562f887fc8991b",
"moleculeId": "sa_09e36465fb6a137e9dd00b2f",
"parentId": "10216",
"isLeaf": true,
"molecule": {
"id": "sa_09e36465fb6a137e9dd00b2f",
"inchikey": "IQXXEPZFOOTTBA-UHFFFAOYSA-N",
"smiles": "c1ccc(CN2CCNCC2)cc1"
},
"smiles": "c1ccc(CN2CCNCC2)cc1",
"reactionStepId": null,
"template": null,
"metadata": null,
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}
]
}
]
},
{
"id": "10219",
"routeId": "sa_b2291dadbc562f887fc8991b",
"moleculeId": "sa_120396023e7c65601e80380d",
"parentId": "10214",
"isLeaf": true,
"molecule": {
"id": "sa_120396023e7c65601e80380d",
"inchikey": "VRPJIFMKZZEXLR-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(O)=NCC(=O)O"
},
"smiles": "CC(C)(C)OC(=O)NCC(=O)O",
"reactionStepId": null,
"template": null,
"metadata": null,
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"children": []
}
]
}
]
}
]
}
}