Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CN(c1ccc(-c2ccc(-n3ccc(N)n3)cc2O)nn1)C1CC(C)(C)NC(C)(C)C1
InChiKey
IUQMBINWIGHFMS-UHFFFAOYSA-N
Route Signature
2fc9d6f3c33c2fd2d86af95bbddd7147f1473500649074257ffc443454d59373
Synthesis route with 5 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_dd522ef0fce1daa7403c9ffa",
"signature": "2fc9d6f3c33c2fd2d86af95bbddd7147f1473500649074257ffc443454d59373",
"contentHash": "755d0c64dd93f807cd8bfbb00432d62cd25d79c96b144c777d621e2a6b7019ce",
"length": 5,
"isConvergent": true
},
"target": {
"id": "sa_24c2d9994e73f34cb590eacc",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-00380",
"moleculeId": "sa_aab589a95eeb0ae51c210442",
"smiles": "CN(c1ccc(-c2ccc(-n3ccc(N)n3)cc2O)nn1)C1CC(C)(C)NC(C)(C)C1",
"routeLength": 5,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_aab589a95eeb0ae51c210442",
"inchikey": "IUQMBINWIGHFMS-UHFFFAOYSA-N",
"smiles": "CN(c1ccc(-c2ccc(-n3ccc(N)n3)cc2O)nn1)C1CC(C)(C)NC(C)(C)C1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "728",
"routeId": "sa_dd522ef0fce1daa7403c9ffa",
"moleculeId": "sa_aab589a95eeb0ae51c210442",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_aab589a95eeb0ae51c210442",
"inchikey": "IUQMBINWIGHFMS-UHFFFAOYSA-N",
"smiles": "CN(c1ccc(-c2ccc(-n3ccc(N)n3)cc2O)nn1)C1CC(C)(C)NC(C)(C)C1"
},
"smiles": "CN(c1ccc(-c2ccc(-n3ccc(N)n3)cc2O)nn1)C1CC(C)(C)NC(C)(C)C1",
"reactionStepId": "sa_5c800deb6bb4234c7fe4b49e",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08729263B2;0499;1461625\",\"rsmi\":\"C[O:9][c:8]1[c:7](-[c:6]2[cH:5][cH:4][c:3]([N:2]([CH3:1])[CH:22]3[CH2:23][C:24]([CH3:25])([CH3:26])[NH:27][C:28]([CH3:29])([CH3:30])[CH2:31]3)[n:21][n:20]2)[cH:19][cH:18][c:11](-[n:12]2[cH:13][cH:14][c:15]([NH2:16])[n:17]2)[cH:10]1>CN1CCCC1=O.Cl.O=C(O)O.Sc1ccccc1.[K+].[K+]>[CH3:1][N:2]([c:3]1[cH:4][cH:5][c:6](-[c:7]2[c:8]([OH:9])[cH:10][c:11](-[n:12]3[cH:13][cH:14][c:15]([NH2:16])[n:17]3)[cH:18][cH:19]2)[n:20][n:21]1)[CH:22]1[CH2:23][C:24]([CH3:25])([CH3:26])[NH:27][C:28]([CH3:29])([CH3:30])[CH2:31]1\"},\"mapped_reaction_smiles\":\"C[O:9][c:8]1[c:7](-[c:6]2[cH:5][cH:4][c:3]([N:2]([CH3:1])[CH:22]3[CH2:23][C:24]([CH3:25])([CH3:26])[NH:27][C:28]([CH3:29])([CH3:30])[CH2:31]3)[n:21][n:20]2)[cH:19][cH:18][c:11](-[n:12]2[cH:13][cH:14][c:15]([NH2:16])[n:17]2)[cH:10]1>CN1CCCC1=O.Cl.O=C(O)O.Sc1ccccc1.[K+].[K+]>[CH3:1][N:2]([c:3]1[cH:4][cH:5][c:6](-[c:7]2[c:8]([OH:9])[cH:10][c:11](-[n:12]3[cH:13][cH:14][c:15]([NH2:16])[n:17]3)[cH:18][cH:19]2)[n:20][n:21]1)[CH:22]1[CH2:23][C:24]([CH3:25])([CH3:26])[NH:27][C:28]([CH3:29])([CH3:30])[CH2:31]1\"}",
"reactionStep": {
"id": "sa_5c800deb6bb4234c7fe4b49e",
"reactionHash": "8abe8102736215489c642631f63b50e9e6b5f81a385c84d3ec26c25036575168"
},
"children": [
{
"id": "729",
"routeId": "sa_dd522ef0fce1daa7403c9ffa",
"moleculeId": "sa_fde9a895d257516e4ef83216",
"parentId": "728",
"isLeaf": false,
"molecule": {
"id": "sa_fde9a895d257516e4ef83216",
"inchikey": "JCSGLZXJNZIEBY-UHFFFAOYSA-N",
"smiles": "COc1cc(-n2ccc(N)n2)ccc1-c1ccc(N(C)C2CC(C)(C)NC(C)(C)C2)nn1"
},
"smiles": "COc1cc(-n2ccc(N)n2)ccc1-c1ccc(N(C)C2CC(C)(C)NC(C)(C)C2)nn1",
"reactionStepId": "sa_543285553ea670d142364b29",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08729263B2;0498;1461624\",\"rsmi\":\"CC1(C)OB([c:4]2[c:3]([O:2][CH3:1])[cH:32][c:25](-[n:26]3[cH:27][cH:28][c:29]([NH2:30])[n:31]3)[cH:24][cH:23]2)OC1(C)C.Cl[c:5]1[cH:6][cH:7][c:8]([N:9]([CH3:10])[CH:11]2[CH2:12][C:13]([CH3:14])([CH3:15])[NH:16][C:17]([CH3:18])([CH3:19])[CH2:20]2)[n:21][n:22]1>C1COCCO1.CCOCC.O.O=C(O)O.[Na+].c1ccc([PH](c2ccccc2)(c2ccccc2)[Pd]([PH](c2ccccc2)(c2ccccc2)c2ccccc2)([PH](c2ccccc2)(c2ccccc2)c2ccccc2)[PH](c2ccccc2)(c2ccccc2)c2ccccc2)cc1>[CH3:1][O:2][c:3]1[c:4](-[c:5]2[cH:6][cH:7][c:8]([N:9]([CH3:10])[CH:11]3[CH2:12][C:13]([CH3:14])([CH3:15])[NH:16][C:17]([CH3:18])([CH3:19])[CH2:20]3)[n:21][n:22]2)[cH:23][cH:24][c:25](-[n:26]2[cH:27][cH:28][c:29]([NH2:30])[n:31]2)[cH:32]1\"},\"mapped_reaction_smiles\":\"CC1(C)OB([c:4]2[c:3]([O:2][CH3:1])[cH:32][c:25](-[n:26]3[cH:27][cH:28][c:29]([NH2:30])[n:31]3)[cH:24][cH:23]2)OC1(C)C.Cl[c:5]1[cH:6][cH:7][c:8]([N:9]([CH3:10])[CH:11]2[CH2:12][C:13]([CH3:14])([CH3:15])[NH:16][C:17]([CH3:18])([CH3:19])[CH2:20]2)[n:21][n:22]1>C1COCCO1.CCOCC.O.O=C(O)O.[Na+].c1ccc([PH](c2ccccc2)(c2ccccc2)[Pd]([PH](c2ccccc2)(c2ccccc2)c2ccccc2)([PH](c2ccccc2)(c2ccccc2)c2ccccc2)[PH](c2ccccc2)(c2ccccc2)c2ccccc2)cc1>[CH3:1][O:2][c:3]1[c:4](-[c:5]2[cH:6][cH:7][c:8]([N:9]([CH3:10])[CH:11]3[CH2:12][C:13]([CH3:14])([CH3:15])[NH:16][C:17]([CH3:18])([CH3:19])[CH2:20]3)[n:21][n:22]2)[cH:23][cH:24][c:25](-[n:26]2[cH:27][cH:28][c:29]([NH2:30])[n:31]2)[cH:32]1\"}",
"reactionStep": {
"id": "sa_543285553ea670d142364b29",
"reactionHash": "8e1126b37e09cbb1df6979d99a08d324e8fd6913b038097fb01fa8032d2dd3a2"
},
"children": [
{
"id": "730",
"routeId": "sa_dd522ef0fce1daa7403c9ffa",
"moleculeId": "sa_6ddea1b44d4816035780540c",
"parentId": "729",
"isLeaf": false,
"molecule": {
"id": "sa_6ddea1b44d4816035780540c",
"inchikey": "LHJDDHAMFMZGDH-UHFFFAOYSA-N",
"smiles": "COc1cc(-n2ccc(N)n2)ccc1B1OC(C)(C)C(C)(C)O1"
},
"smiles": "COc1cc(-n2ccc(N)n2)ccc1B1OC(C)(C)C(C)(C)O1",
"reactionStepId": "sa_1b2190fec623450cc843ca27",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08729263B2;0497;1461623\",\"rsmi\":\"Br[c:4]1[c:3]([O:2][CH3:1])[cH:23][c:16](-[n:17]2[cH:18][cH:19][c:20]([NH2:21])[n:22]2)[cH:15][cH:14]1.CC1(C)OB([B:5]2[O:6][C:7]([CH3:8])([CH3:9])[C:10]([CH3:11])([CH3:12])[O:13]2)OC1(C)C>C1COCCO1.CC(=O)O.Cl[Pd]Cl.[Fe+2].[Fe+2].[K+]>[CH3:1][O:2][c:3]1[c:4]([B:5]2[O:6][C:7]([CH3:8])([CH3:9])[C:10]([CH3:11])([CH3:12])[O:13]2)[cH:14][cH:15][c:16](-[n:17]2[cH:18][cH:19][c:20]([NH2:21])[n:22]2)[cH:23]1\"},\"mapped_reaction_smiles\":\"Br[c:4]1[c:3]([O:2][CH3:1])[cH:23][c:16](-[n:17]2[cH:18][cH:19][c:20]([NH2:21])[n:22]2)[cH:15][cH:14]1.CC1(C)OB([B:5]2[O:6][C:7]([CH3:8])([CH3:9])[C:10]([CH3:11])([CH3:12])[O:13]2)OC1(C)C>C1COCCO1.CC(=O)O.Cl[Pd]Cl.[Fe+2].[Fe+2].[K+]>[CH3:1][O:2][c:3]1[c:4]([B:5]2[O:6][C:7]([CH3:8])([CH3:9])[C:10]([CH3:11])([CH3:12])[O:13]2)[cH:14][cH:15][c:16](-[n:17]2[cH:18][cH:19][c:20]([NH2:21])[n:22]2)[cH:23]1\"}",
"reactionStep": {
"id": "sa_1b2190fec623450cc843ca27",
"reactionHash": "598b3132386850dfbb55e5df139d35b8a2da1715ac226d6a75647365d61236ce"
},
"children": [
{
"id": "731",
"routeId": "sa_dd522ef0fce1daa7403c9ffa",
"moleculeId": "sa_e6c301388ac142801d4af5a2",
"parentId": "730",
"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,
"reactionStep": null,
"children": []
},
{
"id": "732",
"routeId": "sa_dd522ef0fce1daa7403c9ffa",
"moleculeId": "sa_ae4534ebefa609dcb4d55ab4",
"parentId": "730",
"isLeaf": false,
"molecule": {
"id": "sa_ae4534ebefa609dcb4d55ab4",
"inchikey": "JTXRERWJFTZFSO-UHFFFAOYSA-N",
"smiles": "COc1cc(-n2ccc(N)n2)ccc1Br"
},
"smiles": "COc1cc(-n2ccc(N)n2)ccc1Br",
"reactionStepId": "sa_6056f6cdf0d66991b5bf5736",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08729263B2;0496;1461622\",\"rsmi\":\"O=[N+:13]([O-])[c:12]1[cH:11][cH:10][n:9](-[c:8]2[cH:7][cH:6][c:4]([Br:5])[c:3]([O:2][CH3:1])[cH:15]2)[n:14]1>CC(=O)O.Cc1ccccc1.ClCCl.[Zn]>[CH3:1][O:2][c:3]1[c:4]([Br:5])[cH:6][cH:7][c:8](-[n:9]2[cH:10][cH:11][c:12]([NH2:13])[n:14]2)[cH:15]1\"},\"mapped_reaction_smiles\":\"O=[N+:13]([O-])[c:12]1[cH:11][cH:10][n:9](-[c:8]2[cH:7][cH:6][c:4]([Br:5])[c:3]([O:2][CH3:1])[cH:15]2)[n:14]1>CC(=O)O.Cc1ccccc1.ClCCl.[Zn]>[CH3:1][O:2][c:3]1[c:4]([Br:5])[cH:6][cH:7][c:8](-[n:9]2[cH:10][cH:11][c:12]([NH2:13])[n:14]2)[cH:15]1\"}",
"reactionStep": {
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"reactionHash": "7d0055ca912c5ed50deb74facb03bf45c3eea2ee9c5c2c7cbf19cb5a762947e8"
},
"children": [
{
"id": "733",
"routeId": "sa_dd522ef0fce1daa7403c9ffa",
"moleculeId": "sa_f70c492db1566b76361442e4",
"parentId": "732",
"isLeaf": false,
"molecule": {
"id": "sa_f70c492db1566b76361442e4",
"inchikey": "CLIITJGOZJCJKU-UHFFFAOYSA-N",
"smiles": "COc1cc(-n2ccc([N+](=O)[O-])n2)ccc1Br"
},
"smiles": "COc1cc(-n2ccc([N+](=O)[O-])n2)ccc1Br",
"reactionStepId": "sa_9ff5b5815ea174362b0985d9",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08729263B2;0495;1461621\",\"rsmi\":\"I[c:8]1[cH:7][cH:6][c:4]([Br:5])[c:3]([O:2][CH3:1])[cH:17]1.[nH:9]1[cH:10][cH:11][c:12]([N+:13](=[O:14])[O-:15])[n:16]1>CN(C)C=O.O=C(O)O.ON=Cc1ccccc1O.[Cs+].[Cs+]>[CH3:1][O:2][c:3]1[c:4]([Br:5])[cH:6][cH:7][c:8](-[n:9]2[cH:10][cH:11][c:12]([N+:13](=[O:14])[O-:15])[n:16]2)[cH:17]1\"},\"mapped_reaction_smiles\":\"I[c:8]1[cH:7][cH:6][c:4]([Br:5])[c:3]([O:2][CH3:1])[cH:17]1.[nH:9]1[cH:10][cH:11][c:12]([N+:13](=[O:14])[O-:15])[n:16]1>CN(C)C=O.O=C(O)O.ON=Cc1ccccc1O.[Cs+].[Cs+]>[CH3:1][O:2][c:3]1[c:4]([Br:5])[cH:6][cH:7][c:8](-[n:9]2[cH:10][cH:11][c:12]([N+:13](=[O:14])[O-:15])[n:16]2)[cH:17]1\"}",
"reactionStep": {
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"reactionHash": "c3dec0e7023e1a8ac41236c32c7627ef1b574ba1c47fff82aa5090e4588f1a99"
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"children": [
{
"id": "734",
"routeId": "sa_dd522ef0fce1daa7403c9ffa",
"moleculeId": "sa_9645a8ce1f4cb446b963c841",
"parentId": "733",
"isLeaf": true,
"molecule": {
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"inchikey": "MZRUFMBFIKGOAL-UHFFFAOYSA-N",
"smiles": "O=[N+]([O-])c1cc[nH]n1"
},
"smiles": "O=[N+]([O-])c1cc[nH]n1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "735",
"routeId": "sa_dd522ef0fce1daa7403c9ffa",
"moleculeId": "sa_6fe4b5e2be01027158a3b5a4",
"parentId": "733",
"isLeaf": true,
"molecule": {
"id": "sa_6fe4b5e2be01027158a3b5a4",
"inchikey": "PIPWNWZBTWYPJB-UHFFFAOYSA-N",
"smiles": "COc1cc(I)ccc1Br"
},
"smiles": "COc1cc(I)ccc1Br",
"reactionStepId": null,
"template": null,
"metadata": null,
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"children": []
}
]
}
]
}
]
},
{
"id": "736",
"routeId": "sa_dd522ef0fce1daa7403c9ffa",
"moleculeId": "sa_5252f53dbf6176116c4a7521",
"parentId": "729",
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"molecule": {
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"inchikey": "VIFJLLKYDCECIX-UHFFFAOYSA-N",
"smiles": "CN(c1ccc(Cl)nn1)C1CC(C)(C)NC(C)(C)C1"
},
"smiles": "CN(c1ccc(Cl)nn1)C1CC(C)(C)NC(C)(C)C1",
"reactionStepId": "sa_9338fee84c2a7925c1c46552",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08729263B2;0372;1461578\",\"rsmi\":\"Cl[c:3]1[cH:4][cH:5][c:6]([Cl:7])[n:8][n:9]1.[CH3:1][NH:2][CH:10]1[CH2:11][C:12]([CH3:13])([CH3:14])[NH:15][C:16]([CH3:17])([CH3:18])[CH2:19]1>CCCCO>[CH3:1][N:2]([c:3]1[cH:4][cH:5][c:6]([Cl:7])[n:8][n:9]1)[CH:10]1[CH2:11][C:12]([CH3:13])([CH3:14])[NH:15][C:16]([CH3:17])([CH3:18])[CH2:19]1\"},\"mapped_reaction_smiles\":\"Cl[c:3]1[cH:4][cH:5][c:6]([Cl:7])[n:8][n:9]1.[CH3:1][NH:2][CH:10]1[CH2:11][C:12]([CH3:13])([CH3:14])[NH:15][C:16]([CH3:17])([CH3:18])[CH2:19]1>CCCCO>[CH3:1][N:2]([c:3]1[cH:4][cH:5][c:6]([Cl:7])[n:8][n:9]1)[CH:10]1[CH2:11][C:12]([CH3:13])([CH3:14])[NH:15][C:16]([CH3:17])([CH3:18])[CH2:19]1\"}",
"reactionStep": {
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"children": [
{
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"molecule": {
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"inchikey": "GMIARZNQLSJFCP-UHFFFAOYSA-N",
"smiles": "CNC1CC(C)(C)NC(C)(C)C1"
},
"smiles": "CNC1CC(C)(C)NC(C)(C)C1",
"reactionStepId": null,
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"metadata": null,
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},
{
"id": "738",
"routeId": "sa_dd522ef0fce1daa7403c9ffa",
"moleculeId": "sa_d426f4f999390ebabedeebdb",
"parentId": "736",
"isLeaf": true,
"molecule": {
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"inchikey": "GUSWJGOYDXFJSI-UHFFFAOYSA-N",
"smiles": "Clc1ccc(Cl)nn1"
},
"smiles": "Clc1ccc(Cl)nn1",
"reactionStepId": null,
"template": null,
"metadata": null,
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"children": []
}
]
}
]
}
]
}
}