Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CC(=O)Nc1nc2cnc(N(c3cccc(NC(=O)c4cccc(C(C)(C)C#N)c4)c3)C3CC3)nc2s1
InChiKey
FVXIOHFRFNYHPK-UHFFFAOYSA-N
Route Signature
1e63a3785fe59ac1aabd0f77331be5c4e7afda4c4687bb596797b5693727c8a1
Synthesis route with 5 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_c8926f40211c16c1f4b203da",
"signature": "1e63a3785fe59ac1aabd0f77331be5c4e7afda4c4687bb596797b5693727c8a1",
"contentHash": "79d751a88fc8d7a4985af15858a9505e54a0dd6b37f93a152ac031fabdc378ac",
"length": 5,
"isConvergent": true
},
"target": {
"id": "sa_5898dc4d48fe13ff1e8e2207",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-01036",
"moleculeId": "sa_654ad29c48a07c7a9bf66d09",
"smiles": "CC(=O)Nc1nc2cnc(N(c3cccc(NC(=O)c4cccc(C(C)(C)C#N)c4)c3)C3CC3)nc2s1",
"routeLength": 5,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_654ad29c48a07c7a9bf66d09",
"inchikey": "FVXIOHFRFNYHPK-UHFFFAOYSA-N",
"smiles": "CC(=O)Nc1nc2cnc(N(c3cccc(NC(=O)c4cccc(C(C)(C)C#N)c4)c3)C3CC3)nc2s1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "9908",
"routeId": "sa_c8926f40211c16c1f4b203da",
"moleculeId": "sa_654ad29c48a07c7a9bf66d09",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_654ad29c48a07c7a9bf66d09",
"inchikey": "FVXIOHFRFNYHPK-UHFFFAOYSA-N",
"smiles": "CC(=O)Nc1nc2cnc(N(c3cccc(NC(=O)c4cccc(C(C)(C)C#N)c4)c3)C3CC3)nc2s1"
},
"smiles": "CC(=O)Nc1nc2cnc(N(c3cccc(NC(=O)c4cccc(C(C)(C)C#N)c4)c3)C3CC3)nc2s1",
"reactionStepId": "sa_ce3fe55ebe4fede1d0c366f1",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08344135B2;2145;1268780\",\"rsmi\":\"O[C:18](=[O:19])[c:20]1[cH:21][c:22]([C:23]([CH3:24])([CH3:25])[C:26]#[N:27])[cH:28][cH:29][cH:30]1.[CH3:1][C:2](=[O:3])[NH:4][c:5]1[n:6][c:7]2[c:8]([n:9][c:10]([N:11]([c:12]3[cH:13][cH:14][cH:15][c:16]([NH2:17])[cH:31]3)[CH:32]3[CH2:33][CH2:34]3)[n:35][cH:36]2)[s:37]1>CN(C)C(On1nnc2cccnc21)=[N+](C)C.F[PH](F)(F)(F)(F)F.O=C(O)O.[Na+].c1ccncc1>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[n:6][c:7]2[c:8]([n:9][c:10]([N:11]([c:12]3[cH:13][cH:14][cH:15][c:16]([NH:17][C:18](=[O:19])[c:20]4[cH:21][c:22]([C:23]([CH3:24])([CH3:25])[C:26]#[N:27])[cH:28][cH:29][cH:30]4)[cH:31]3)[CH:32]3[CH2:33][CH2:34]3)[n:35][cH:36]2)[s:37]1\"},\"mapped_reaction_smiles\":\"O[C:18](=[O:19])[c:20]1[cH:21][c:22]([C:23]([CH3:24])([CH3:25])[C:26]#[N:27])[cH:28][cH:29][cH:30]1.[CH3:1][C:2](=[O:3])[NH:4][c:5]1[n:6][c:7]2[c:8]([n:9][c:10]([N:11]([c:12]3[cH:13][cH:14][cH:15][c:16]([NH2:17])[cH:31]3)[CH:32]3[CH2:33][CH2:34]3)[n:35][cH:36]2)[s:37]1>CN(C)C(On1nnc2cccnc21)=[N+](C)C.F[PH](F)(F)(F)(F)F.O=C(O)O.[Na+].c1ccncc1>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[n:6][c:7]2[c:8]([n:9][c:10]([N:11]([c:12]3[cH:13][cH:14][cH:15][c:16]([NH:17][C:18](=[O:19])[c:20]4[cH:21][c:22]([C:23]([CH3:24])([CH3:25])[C:26]#[N:27])[cH:28][cH:29][cH:30]4)[cH:31]3)[CH:32]3[CH2:33][CH2:34]3)[n:35][cH:36]2)[s:37]1\"}",
"reactionStep": {
"id": "sa_ce3fe55ebe4fede1d0c366f1",
"reactionHash": "8983456045e7ca0da7b5917c21b48b6a9ac18308ce3b911edacfc8e6ec6cf0c4"
},
"children": [
{
"id": "9909",
"routeId": "sa_c8926f40211c16c1f4b203da",
"moleculeId": "sa_cdcd94fd3d30257d933047e5",
"parentId": "9908",
"isLeaf": false,
"molecule": {
"id": "sa_cdcd94fd3d30257d933047e5",
"inchikey": "CZKMOHAJFKFOBK-UHFFFAOYSA-N",
"smiles": "CC(=O)Nc1nc2cnc(N(c3cccc(N)c3)C3CC3)nc2s1"
},
"smiles": "CC(=O)Nc1nc2cnc(N(c3cccc(N)c3)C3CC3)nc2s1",
"reactionStepId": "sa_dff5819d8cc9f62fffed8f4b",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08344135B2;2143;1268779\",\"rsmi\":\"CC(C)(C)OC(=O)[NH:15][c:14]1[cH:13][c:12]([N:11]([c:10]2[n:9][c:8]3[c:7]([n:6][c:5]([NH:4][C:2]([CH3:1])=[O:3])[s:24]3)[cH:23][n:22]2)[CH:19]2[CH2:20][CH2:21]2)[cH:18][cH:17][cH:16]1>COc1ccccc1.O=C(O)C(F)(F)F>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[n:6][c:7]2[c:8]([n:9][c:10]([N:11]([c:12]3[cH:13][c:14]([NH2:15])[cH:16][cH:17][cH:18]3)[CH:19]3[CH2:20][CH2:21]3)[n:22][cH:23]2)[s:24]1\"},\"mapped_reaction_smiles\":\"CC(C)(C)OC(=O)[NH:15][c:14]1[cH:13][c:12]([N:11]([c:10]2[n:9][c:8]3[c:7]([n:6][c:5]([NH:4][C:2]([CH3:1])=[O:3])[s:24]3)[cH:23][n:22]2)[CH:19]2[CH2:20][CH2:21]2)[cH:18][cH:17][cH:16]1>COc1ccccc1.O=C(O)C(F)(F)F>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[n:6][c:7]2[c:8]([n:9][c:10]([N:11]([c:12]3[cH:13][c:14]([NH2:15])[cH:16][cH:17][cH:18]3)[CH:19]3[CH2:20][CH2:21]3)[n:22][cH:23]2)[s:24]1\"}",
"reactionStep": {
"id": "sa_dff5819d8cc9f62fffed8f4b",
"reactionHash": "e931122d9af2bd280804287bb699ad151dfedb786bd739a91b9aabf9deeadeb9"
},
"children": [
{
"id": "9910",
"routeId": "sa_c8926f40211c16c1f4b203da",
"moleculeId": "sa_2d35b5781543ac1999c66daf",
"parentId": "9909",
"isLeaf": false,
"molecule": {
"id": "sa_2d35b5781543ac1999c66daf",
"inchikey": "YJUJZKIAPBUICU-UHFFFAOYSA-N",
"smiles": "CC(=O)Nc1nc2cnc(N(c3cccc(NC(=O)OC(C)(C)C)c3)C3CC3)nc2s1"
},
"smiles": "CC(=O)Nc1nc2cnc(N(c3cccc(NC(=O)OC(C)(C)C)c3)C3CC3)nc2s1",
"reactionStepId": "sa_27ff31a1fa71a84e0dcf5e82",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08344135B2;2142;1268778\",\"rsmi\":\"Cl[C:2]([CH3:1])=[O:3].[NH2:4][c:5]1[n:6][c:7]2[c:8]([n:9][c:10]([N:11]([c:12]3[cH:13][cH:14][cH:15][c:16]([NH:17][C:18](=[O:19])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])[cH:25]3)[CH:26]3[CH2:27][CH2:28]3)[n:29][cH:30]2)[s:31]1>O.c1ccncc1>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[n:6][c:7]2[c:8]([n:9][c:10]([N:11]([c:12]3[cH:13][cH:14][cH:15][c:16]([NH:17][C:18](=[O:19])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])[cH:25]3)[CH:26]3[CH2:27][CH2:28]3)[n:29][cH:30]2)[s:31]1\"},\"mapped_reaction_smiles\":\"Cl[C:2]([CH3:1])=[O:3].[NH2:4][c:5]1[n:6][c:7]2[c:8]([n:9][c:10]([N:11]([c:12]3[cH:13][cH:14][cH:15][c:16]([NH:17][C:18](=[O:19])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])[cH:25]3)[CH:26]3[CH2:27][CH2:28]3)[n:29][cH:30]2)[s:31]1>O.c1ccncc1>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[n:6][c:7]2[c:8]([n:9][c:10]([N:11]([c:12]3[cH:13][cH:14][cH:15][c:16]([NH:17][C:18](=[O:19])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])[cH:25]3)[CH:26]3[CH2:27][CH2:28]3)[n:29][cH:30]2)[s:31]1\"}",
"reactionStep": {
"id": "sa_27ff31a1fa71a84e0dcf5e82",
"reactionHash": "61a76f8073e5e22a2ce6efe319a1c9244ee2e244fca3c0867944948675fdf503"
},
"children": [
{
"id": "9911",
"routeId": "sa_c8926f40211c16c1f4b203da",
"moleculeId": "sa_170bb03cc6b70732d8cf8f53",
"parentId": "9910",
"isLeaf": false,
"molecule": {
"id": "sa_170bb03cc6b70732d8cf8f53",
"inchikey": "PXLIAHGKRQFUTM-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)Nc1cccc(N(c2ncc3nc(N)sc3n2)C2CC2)c1"
},
"smiles": "CC(C)(C)OC(=O)Nc1cccc(N(c2ncc3nc(N)sc3n2)C2CC2)c1",
"reactionStepId": "sa_b3b7495ea6f0e3bafdc8e374",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08344135B2;2140;1268777\",\"rsmi\":\"O=[N+:19]([O-])[c:16]1[c:15]([S:22][C:20]#[N:21])[n:14][c:13]([N:12]([c:11]2[cH:10][c:9]([NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[cH:28][cH:27][cH:26]2)[CH:23]2[CH2:24][CH2:25]2)[n:18][cH:17]1>CCO.CN1CCCC1=O.O.[Ca+2].Cl.Cl>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][c:9]1[cH:10][c:11]([N:12]([c:13]2[n:14][c:15]3[c:16]([cH:17][n:18]2)[n:19][c:20]([NH2:21])[s:22]3)[CH:23]2[CH2:24][CH2:25]2)[cH:26][cH:27][cH:28]1\"},\"mapped_reaction_smiles\":\"O=[N+:19]([O-])[c:16]1[c:15]([S:22][C:20]#[N:21])[n:14][c:13]([N:12]([c:11]2[cH:10][c:9]([NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[cH:28][cH:27][cH:26]2)[CH:23]2[CH2:24][CH2:25]2)[n:18][cH:17]1>CCO.CN1CCCC1=O.O.[Ca+2].Cl.Cl>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][c:9]1[cH:10][c:11]([N:12]([c:13]2[n:14][c:15]3[c:16]([cH:17][n:18]2)[n:19][c:20]([NH2:21])[s:22]3)[CH:23]2[CH2:24][CH2:25]2)[cH:26][cH:27][cH:28]1\"}",
"reactionStep": {
"id": "sa_b3b7495ea6f0e3bafdc8e374",
"reactionHash": "0c982cf9343fe8e6c2e41da3568bc0fdf0cf008b75b86c7b386b8c9c3e5efd8a"
},
"children": [
{
"id": "9912",
"routeId": "sa_c8926f40211c16c1f4b203da",
"moleculeId": "sa_ebac75d5b0a076396ef82430",
"parentId": "9911",
"isLeaf": false,
"molecule": {
"id": "sa_ebac75d5b0a076396ef82430",
"inchikey": "LRLBJJQPNXGABQ-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)Nc1cccc(N(c2ncc([N+](=O)[O-])c(SC#N)n2)C2CC2)c1"
},
"smiles": "CC(C)(C)OC(=O)Nc1cccc(N(c2ncc([N+](=O)[O-])c(SC#N)n2)C2CC2)c1",
"reactionStepId": "sa_8216d8aa6a349bac32b847d5",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08344135B2;2139;1268776\",\"rsmi\":\"Cl[c:13]1[n:14][cH:15][c:16]([N+:17](=[O:18])[O-:19])[c:20]([S:21][C:22]#[N:23])[n:24]1.[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][c:9]1[cH:10][c:11]([NH:12][CH:25]2[CH2:26][CH2:27]2)[cH:28][cH:29][cH:30]1>C1CCOC1.CCN(C(C)C)C(C)C.O>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][c:9]1[cH:10][c:11]([N:12]([c:13]2[n:14][cH:15][c:16]([N+:17](=[O:18])[O-:19])[c:20]([S:21][C:22]#[N:23])[n:24]2)[CH:25]2[CH2:26][CH2:27]2)[cH:28][cH:29][cH:30]1\"},\"mapped_reaction_smiles\":\"Cl[c:13]1[n:14][cH:15][c:16]([N+:17](=[O:18])[O-:19])[c:20]([S:21][C:22]#[N:23])[n:24]1.[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][c:9]1[cH:10][c:11]([NH:12][CH:25]2[CH2:26][CH2:27]2)[cH:28][cH:29][cH:30]1>C1CCOC1.CCN(C(C)C)C(C)C.O>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][c:9]1[cH:10][c:11]([N:12]([c:13]2[n:14][cH:15][c:16]([N+:17](=[O:18])[O-:19])[c:20]([S:21][C:22]#[N:23])[n:24]2)[CH:25]2[CH2:26][CH2:27]2)[cH:28][cH:29][cH:30]1\"}",
"reactionStep": {
"id": "sa_8216d8aa6a349bac32b847d5",
"reactionHash": "920f6c98199b614d65101b6a176ba5d5322b9b1c89ccf3ff47b2c2e3a3eeb821"
},
"children": [
{
"id": "9913",
"routeId": "sa_c8926f40211c16c1f4b203da",
"moleculeId": "sa_6fb58abdfa3b9bab4bf2268d",
"parentId": "9912",
"isLeaf": true,
"molecule": {
"id": "sa_6fb58abdfa3b9bab4bf2268d",
"inchikey": "GVMBHKFNIKBISV-UHFFFAOYSA-N",
"smiles": "N#CSc1nc(Cl)ncc1[N+](=O)[O-]"
},
"smiles": "N#CSc1nc(Cl)ncc1[N+](=O)[O-]",
"reactionStepId": null,
"template": null,
"metadata": null,
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"children": []
},
{
"id": "9914",
"routeId": "sa_c8926f40211c16c1f4b203da",
"moleculeId": "sa_6266348b166659a9cdf2be2a",
"parentId": "9912",
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"molecule": {
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"inchikey": "KNNXZIPGTDBWOJ-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)Nc1cccc(NC2CC2)c1"
},
"smiles": "CC(C)(C)OC(=O)Nc1cccc(NC2CC2)c1",
"reactionStepId": null,
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}
]
}
]
},
{
"id": "9915",
"routeId": "sa_c8926f40211c16c1f4b203da",
"moleculeId": "sa_7992c61d309177eaaf95fc6b",
"parentId": "9910",
"isLeaf": true,
"molecule": {
"id": "sa_7992c61d309177eaaf95fc6b",
"inchikey": "WETWJCDKMRHUPV-UHFFFAOYSA-N",
"smiles": "CC(=O)Cl"
},
"smiles": "CC(=O)Cl",
"reactionStepId": null,
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}
]
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]
},
{
"id": "9916",
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"moleculeId": "sa_2a4610d98e84cd618aec9dd6",
"parentId": "9908",
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"molecule": {
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"inchikey": "VSCTXXVTZNQKAX-UHFFFAOYSA-N",
"smiles": "CC(C)(C#N)c1cccc(C(=O)O)c1"
},
"smiles": "CC(C)(C#N)c1cccc(C(=O)O)c1",
"reactionStepId": "sa_10defba268795e94eac5e9ba",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08344135B2;1044;1268430\",\"rsmi\":\"C[O:13][C:11]([c:10]1[cH:9][cH:8][cH:7][c:6]([C:2]([CH3:1])([CH3:3])[C:4]#[N:5])[cH:14]1)=[O:12]>C1CCOC1.CO.O>[CH3:1][C:2]([CH3:3])([C:4]#[N:5])[c:6]1[cH:7][cH:8][cH:9][c:10]([C:11](=[O:12])[OH:13])[cH:14]1\"},\"mapped_reaction_smiles\":\"C[O:13][C:11]([c:10]1[cH:9][cH:8][cH:7][c:6]([C:2]([CH3:1])([CH3:3])[C:4]#[N:5])[cH:14]1)=[O:12]>C1CCOC1.CO.O>[CH3:1][C:2]([CH3:3])([C:4]#[N:5])[c:6]1[cH:7][cH:8][cH:9][c:10]([C:11](=[O:12])[OH:13])[cH:14]1\"}",
"reactionStep": {
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"reactionHash": "f426377396cd496890414db07c18c532babb499bbfdb07a4f5784e825e77f97a"
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"children": [
{
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"moleculeId": "sa_a4ad521eb59fd45d37659a51",
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"molecule": {
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"inchikey": "FKRJEXVTBGQAMO-UHFFFAOYSA-N",
"smiles": "COC(=O)c1cccc(C(C)(C)C#N)c1"
},
"smiles": "COC(=O)c1cccc(C(C)(C)C#N)c1",
"reactionStepId": null,
"template": null,
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}
]
}
]
}
}