Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
C[C@H](CO)Oc1cc(Oc2ccc(C(=O)N3CCC3)cc2F)cc(C(=O)Nc2ccn(C)n2)c1
InChiKey
AKRUGLJLNYJWFQ-OAHLLOKOSA-N
Route Signature
39f81393b6216f0cc3c3bf4a471478f80392cee76b3b5e1c3cdda8d1ab325ec8
Synthesis route with 5 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_3971bdd3725a88369ee26939",
"signature": "39f81393b6216f0cc3c3bf4a471478f80392cee76b3b5e1c3cdda8d1ab325ec8",
"contentHash": "62640c2eac01eebd242d0b7adf3cb1f8501d08707afb1dd12491df649b69d218",
"length": 5,
"isConvergent": true
},
"target": {
"id": "sa_a729b49c0a744493d5d67777",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-01434",
"moleculeId": "sa_92cf15226cd1993695ff3446",
"smiles": "C[C@H](CO)Oc1cc(Oc2ccc(C(=O)N3CCC3)cc2F)cc(C(=O)Nc2ccn(C)n2)c1",
"routeLength": 5,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_92cf15226cd1993695ff3446",
"inchikey": "AKRUGLJLNYJWFQ-OAHLLOKOSA-N",
"smiles": "C[C@H](CO)Oc1cc(Oc2ccc(C(=O)N3CCC3)cc2F)cc(C(=O)Nc2ccn(C)n2)c1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "10190",
"routeId": "sa_3971bdd3725a88369ee26939",
"moleculeId": "sa_92cf15226cd1993695ff3446",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_92cf15226cd1993695ff3446",
"inchikey": "AKRUGLJLNYJWFQ-OAHLLOKOSA-N",
"smiles": "C[C@H](CO)Oc1cc(Oc2ccc(C(=O)N3CCC3)cc2F)cc(C(=O)Nc2ccn(C)n2)c1"
},
"smiles": "C[C@H](CO)Oc1cc(Oc2ccc(C(=O)N3CCC3)cc2F)cc(C(=O)Nc2ccn(C)n2)c1",
"reactionStepId": "sa_f25ada8a7291d044d22f4712",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20080015203A1;0909;538438\",\"rsmi\":\"F[c:21]1[c:22]([F:23])[cH:24][c:25]([C:26](=[O:27])[N:28]2[CH2:29][CH2:30][CH2:31]2)[cH:32][cH:33]1.[CH3:1][C@H:2]([CH2:3][OH:4])[O:5][c:6]1[cH:7][c:8]([C:9](=[O:10])[NH:11][c:12]2[n:13][n:14]([CH3:15])[cH:16][cH:17]2)[cH:18][c:19]([OH:20])[cH:34]1>CC(=O)N(C)C.CC(C)(C)[Si](C)(C)Cl.CN(C)C=O.O.O=C(O)O.[Cs+].[Cs+].c1c[nH]cn1>[CH3:1][C@H:2]([CH2:3][OH:4])[O:5][c:6]1[cH:7][c:8]([C:9](=[O:10])[NH:11][c:12]2[n:13][n:14]([CH3:15])[cH:16][cH:17]2)[cH:18][c:19]([O:20][c:21]2[c:22]([F:23])[cH:24][c:25]([C:26](=[O:27])[N:28]3[CH2:29][CH2:30][CH2:31]3)[cH:32][cH:33]2)[cH:34]1\"},\"mapped_reaction_smiles\":\"F[c:21]1[c:22]([F:23])[cH:24][c:25]([C:26](=[O:27])[N:28]2[CH2:29][CH2:30][CH2:31]2)[cH:32][cH:33]1.[CH3:1][C@H:2]([CH2:3][OH:4])[O:5][c:6]1[cH:7][c:8]([C:9](=[O:10])[NH:11][c:12]2[n:13][n:14]([CH3:15])[cH:16][cH:17]2)[cH:18][c:19]([OH:20])[cH:34]1>CC(=O)N(C)C.CC(C)(C)[Si](C)(C)Cl.CN(C)C=O.O.O=C(O)O.[Cs+].[Cs+].c1c[nH]cn1>[CH3:1][C@H:2]([CH2:3][OH:4])[O:5][c:6]1[cH:7][c:8]([C:9](=[O:10])[NH:11][c:12]2[n:13][n:14]([CH3:15])[cH:16][cH:17]2)[cH:18][c:19]([O:20][c:21]2[c:22]([F:23])[cH:24][c:25]([C:26](=[O:27])[N:28]3[CH2:29][CH2:30][CH2:31]3)[cH:32][cH:33]2)[cH:34]1\"}",
"reactionStep": {
"id": "sa_f25ada8a7291d044d22f4712",
"reactionHash": "a4ad8f619f110d7a1fa69aadd6caf2460c04fb518b6cd6a75c20387f91f64f31"
},
"children": [
{
"id": "10191",
"routeId": "sa_3971bdd3725a88369ee26939",
"moleculeId": "sa_647c610acfe0149fda815aef",
"parentId": "10190",
"isLeaf": false,
"molecule": {
"id": "sa_647c610acfe0149fda815aef",
"inchikey": "BOXIOUFIIIWMMF-UHFFFAOYSA-N",
"smiles": "O=C(c1ccc(F)c(F)c1)N1CCC1"
},
"smiles": "O=C(c1ccc(F)c(F)c1)N1CCC1",
"reactionStepId": "sa_2f66ba1e3a823ffe711a4ebc",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20080015203A1;0683;538382\",\"rsmi\":\"O[C:2](=[O:1])[c:3]1[cH:4][c:5]([F:6])[c:7]([F:8])[cH:9][cH:10]1.[NH:11]1[CH2:12][CH2:13][CH2:14]1>CCN(CC)CC.CN(C)C=O.Cl.ClCCl.O=C(Cl)C(=O)Cl>[O:1]=[C:2]([c:3]1[cH:4][c:5]([F:6])[c:7]([F:8])[cH:9][cH:10]1)[N:11]1[CH2:12][CH2:13][CH2:14]1\"},\"mapped_reaction_smiles\":\"O[C:2](=[O:1])[c:3]1[cH:4][c:5]([F:6])[c:7]([F:8])[cH:9][cH:10]1.[NH:11]1[CH2:12][CH2:13][CH2:14]1>CCN(CC)CC.CN(C)C=O.Cl.ClCCl.O=C(Cl)C(=O)Cl>[O:1]=[C:2]([c:3]1[cH:4][c:5]([F:6])[c:7]([F:8])[cH:9][cH:10]1)[N:11]1[CH2:12][CH2:13][CH2:14]1\"}",
"reactionStep": {
"id": "sa_2f66ba1e3a823ffe711a4ebc",
"reactionHash": "867c31bd65f23a8869df9c9d1bfcfb69fd47f5ac5597272f6de7ad6022c81f47"
},
"children": [
{
"id": "10192",
"routeId": "sa_3971bdd3725a88369ee26939",
"moleculeId": "sa_b8df632b26246916e13badf8",
"parentId": "10191",
"isLeaf": true,
"molecule": {
"id": "sa_b8df632b26246916e13badf8",
"inchikey": "FPENCTDAQQQKNY-UHFFFAOYSA-N",
"smiles": "O=C(O)c1ccc(F)c(F)c1"
},
"smiles": "O=C(O)c1ccc(F)c(F)c1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "10193",
"routeId": "sa_3971bdd3725a88369ee26939",
"moleculeId": "sa_3edf2a7ec025f1195f3401ef",
"parentId": "10191",
"isLeaf": true,
"molecule": {
"id": "sa_3edf2a7ec025f1195f3401ef",
"inchikey": "HONIICLYMWZJFZ-UHFFFAOYSA-N",
"smiles": "C1CNC1"
},
"smiles": "C1CNC1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "10194",
"routeId": "sa_3971bdd3725a88369ee26939",
"moleculeId": "sa_c20c3973b865a592c5157d3f",
"parentId": "10190",
"isLeaf": false,
"molecule": {
"id": "sa_c20c3973b865a592c5157d3f",
"inchikey": "ZXOMVPKFUTWYBJ-SECBINFHSA-N",
"smiles": "C[C@H](CO)Oc1cc(O)cc(C(=O)Nc2ccn(C)n2)c1"
},
"smiles": "C[C@H](CO)Oc1cc(O)cc(C(=O)Nc2ccn(C)n2)c1",
"reactionStepId": "sa_d4ae2c92d36c0d3e33370bc8",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20080015203A1;0913;538439\",\"rsmi\":\"C[O:4][CH2:3][C@@H:2]([CH3:1])[O:5][c:6]1[cH:7][c:8]([C:9](=[O:10])[NH:11][c:12]2[n:13][n:14]([CH3:15])[cH:16][cH:17]2)[cH:18][c:19]([OH:20])[cH:21]1>CC#N.CO.C[Si](C)(C)I.O=C(O)O.O=S(O)(O)=S.[K+].[K+].[Na+].[Na+]>[CH3:1][C@H:2]([CH2:3][OH:4])[O:5][c:6]1[cH:7][c:8]([C:9](=[O:10])[NH:11][c:12]2[n:13][n:14]([CH3:15])[cH:16][cH:17]2)[cH:18][c:19]([OH:20])[cH:21]1\"},\"mapped_reaction_smiles\":\"C[O:4][CH2:3][C@@H:2]([CH3:1])[O:5][c:6]1[cH:7][c:8]([C:9](=[O:10])[NH:11][c:12]2[n:13][n:14]([CH3:15])[cH:16][cH:17]2)[cH:18][c:19]([OH:20])[cH:21]1>CC#N.CO.C[Si](C)(C)I.O=C(O)O.O=S(O)(O)=S.[K+].[K+].[Na+].[Na+]>[CH3:1][C@H:2]([CH2:3][OH:4])[O:5][c:6]1[cH:7][c:8]([C:9](=[O:10])[NH:11][c:12]2[n:13][n:14]([CH3:15])[cH:16][cH:17]2)[cH:18][c:19]([OH:20])[cH:21]1\"}",
"reactionStep": {
"id": "sa_d4ae2c92d36c0d3e33370bc8",
"reactionHash": "e5c4d1e60262225bdb39f02f613527a23b048bafab367665510bcaba959b0a2f"
},
"children": [
{
"id": "10195",
"routeId": "sa_3971bdd3725a88369ee26939",
"moleculeId": "sa_01ed6657656aa815a1e52a46",
"parentId": "10194",
"isLeaf": false,
"molecule": {
"id": "sa_01ed6657656aa815a1e52a46",
"inchikey": "QHHJDJYERISQPI-SNVBAGLBSA-N",
"smiles": "COC[C@@H](C)Oc1cc(O)cc(C(=O)Nc2ccn(C)n2)c1"
},
"smiles": "COC[C@@H](C)Oc1cc(O)cc(C(=O)Nc2ccn(C)n2)c1",
"reactionStepId": "sa_b04855a0de461d27a3afbba7",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20080015203A1;0916;538440\",\"rsmi\":\"c1ccc(C[O:21][c:20]2[cH:19][c:9]([C:10](=[O:11])[NH:12][c:13]3[n:14][n:15]([CH3:16])[cH:17][cH:18]3)[cH:8][c:7]([O:6][C@@H:4]([CH2:3][O:2][CH3:1])[CH3:5])[cH:22]2)cc1>CCO>[CH3:1][O:2][CH2:3][C@@H:4]([CH3:5])[O:6][c:7]1[cH:8][c:9]([C:10](=[O:11])[NH:12][c:13]2[n:14][n:15]([CH3:16])[cH:17][cH:18]2)[cH:19][c:20]([OH:21])[cH:22]1\"},\"mapped_reaction_smiles\":\"c1ccc(C[O:21][c:20]2[cH:19][c:9]([C:10](=[O:11])[NH:12][c:13]3[n:14][n:15]([CH3:16])[cH:17][cH:18]3)[cH:8][c:7]([O:6][C@@H:4]([CH2:3][O:2][CH3:1])[CH3:5])[cH:22]2)cc1>CCO>[CH3:1][O:2][CH2:3][C@@H:4]([CH3:5])[O:6][c:7]1[cH:8][c:9]([C:10](=[O:11])[NH:12][c:13]2[n:14][n:15]([CH3:16])[cH:17][cH:18]2)[cH:19][c:20]([OH:21])[cH:22]1\"}",
"reactionStep": {
"id": "sa_b04855a0de461d27a3afbba7",
"reactionHash": "bb1bbba8506f888b7accf64fe763c19883f0bfc709408b60e75df98bb55e51b6"
},
"children": [
{
"id": "10196",
"routeId": "sa_3971bdd3725a88369ee26939",
"moleculeId": "sa_cf43d08f1cc4d610cd29c200",
"parentId": "10195",
"isLeaf": false,
"molecule": {
"id": "sa_cf43d08f1cc4d610cd29c200",
"inchikey": "DMOUIAJRDYZNLY-MRXNPFEDSA-N",
"smiles": "COC[C@@H](C)Oc1cc(OCc2ccccc2)cc(C(=O)Nc2ccn(C)n2)c1"
},
"smiles": "COC[C@@H](C)Oc1cc(OCc2ccccc2)cc(C(=O)Nc2ccn(C)n2)c1",
"reactionStepId": "sa_031413af3a231f7657c193ca",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20080015203A1;0919;538441\",\"rsmi\":\"O[C:10]([c:9]1[cH:8][c:7]([O:6][C@@H:4]([CH2:3][O:2][CH3:1])[CH3:5])[cH:29][c:20]([O:21][CH2:22][c:23]2[cH:24][cH:25][cH:26][cH:27][cH:28]2)[cH:19]1)=[O:11].[NH2:12][c:13]1[n:14][n:15]([CH3:16])[cH:17][cH:18]1>CCN(CC)CC.CN(C)C=O.ClCCl.O=C(Cl)C(=O)Cl>[CH3:1][O:2][CH2:3][C@@H:4]([CH3:5])[O:6][c:7]1[cH:8][c:9]([C:10](=[O:11])[NH:12][c:13]2[n:14][n:15]([CH3:16])[cH:17][cH:18]2)[cH:19][c:20]([O:21][CH2:22][c:23]2[cH:24][cH:25][cH:26][cH:27][cH:28]2)[cH:29]1\"},\"mapped_reaction_smiles\":\"O[C:10]([c:9]1[cH:8][c:7]([O:6][C@@H:4]([CH2:3][O:2][CH3:1])[CH3:5])[cH:29][c:20]([O:21][CH2:22][c:23]2[cH:24][cH:25][cH:26][cH:27][cH:28]2)[cH:19]1)=[O:11].[NH2:12][c:13]1[n:14][n:15]([CH3:16])[cH:17][cH:18]1>CCN(CC)CC.CN(C)C=O.ClCCl.O=C(Cl)C(=O)Cl>[CH3:1][O:2][CH2:3][C@@H:4]([CH3:5])[O:6][c:7]1[cH:8][c:9]([C:10](=[O:11])[NH:12][c:13]2[n:14][n:15]([CH3:16])[cH:17][cH:18]2)[cH:19][c:20]([O:21][CH2:22][c:23]2[cH:24][cH:25][cH:26][cH:27][cH:28]2)[cH:29]1\"}",
"reactionStep": {
"id": "sa_031413af3a231f7657c193ca",
"reactionHash": "6fe64fecde90cfba3638cbd6ed8c4a075696300aad42f6b640dd021bcc6edea5"
},
"children": [
{
"id": "10197",
"routeId": "sa_3971bdd3725a88369ee26939",
"moleculeId": "sa_71ddea59cef81e455053db1d",
"parentId": "10196",
"isLeaf": true,
"molecule": {
"id": "sa_71ddea59cef81e455053db1d",
"inchikey": "MOGQNVSKBCVIPW-UHFFFAOYSA-N",
"smiles": "Cn1ccc(=N)[nH]1"
},
"smiles": "Cn1ccc(N)n1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "10198",
"routeId": "sa_3971bdd3725a88369ee26939",
"moleculeId": "sa_f4774a3caf1a63a3a155e8b8",
"parentId": "10196",
"isLeaf": false,
"molecule": {
"id": "sa_f4774a3caf1a63a3a155e8b8",
"inchikey": "PJIAOAQBXXYLRX-CYBMUJFWSA-N",
"smiles": "COC[C@@H](C)Oc1cc(OCc2ccccc2)cc(C(=O)O)c1"
},
"smiles": "COC[C@@H](C)Oc1cc(OCc2ccccc2)cc(C(=O)O)c1",
"reactionStepId": "sa_bbc88350c3fc764e9d17e81f",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20080015203A1;0921;538442\",\"rsmi\":\"C[O:12][C:10]([c:9]1[cH:8][c:7]([O:6][C@@H:4]([CH2:3][O:2][CH3:1])[CH3:5])[cH:23][c:14]([O:15][CH2:16][c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[cH:13]1)=[O:11]>C1CCOC1.O.O.[Li+].O>[CH3:1][O:2][CH2:3][C@@H:4]([CH3:5])[O:6][c:7]1[cH:8][c:9]([C:10](=[O:11])[OH:12])[cH:13][c:14]([O:15][CH2:16][c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[cH:23]1\"},\"mapped_reaction_smiles\":\"C[O:12][C:10]([c:9]1[cH:8][c:7]([O:6][C@@H:4]([CH2:3][O:2][CH3:1])[CH3:5])[cH:23][c:14]([O:15][CH2:16][c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[cH:13]1)=[O:11]>C1CCOC1.O.O.[Li+].O>[CH3:1][O:2][CH2:3][C@@H:4]([CH3:5])[O:6][c:7]1[cH:8][c:9]([C:10](=[O:11])[OH:12])[cH:13][c:14]([O:15][CH2:16][c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[cH:23]1\"}",
"reactionStep": {
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"reactionHash": "25e3413fbdb5dd237857975079db1f4d6d09f2f7ec1b5a25656129bad635f216"
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"children": [
{
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"molecule": {
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"smiles": "COC[C@@H](C)Oc1cc(OCc2ccccc2)cc(C(=O)OC)c1"
},
"smiles": "COC[C@@H](C)Oc1cc(OCc2ccccc2)cc(C(=O)OC)c1",
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}
]
}
]
}
]
}
]
}
]
}
}