Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
COc1cc(Nc2nc3c(s2)CC(O)CC3c2ccc(F)cc2)ccc1-n1cnc(Cl)c1
InChiKey
ISBVQXLOOBKUBH-UHFFFAOYSA-N
Route Signature
f33fa8b97e53568704d64d0898d0ffde74a39cd1eecaa2cfc809711828d11e2c
Synthesis route with 7 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_6b51f82090175c05ac9bf7a8",
"signature": "f33fa8b97e53568704d64d0898d0ffde74a39cd1eecaa2cfc809711828d11e2c",
"contentHash": "b6d0eb4164344158bb190f1ce87d929dfab9dce22a993ef12baa43a96282bd12",
"length": 7,
"isConvergent": false
},
"target": {
"id": "sa_e79d58d6a4ba836d7325882a",
"benchmarkSetId": "61e696668b63e77d7c2a29c0821768e1c383de8313852d6e995224859494442e",
"targetId": "n5-00324",
"moleculeId": "sa_1cf7513966e88d2e13a9abd7",
"smiles": "COc1cc(Nc2nc3c(s2)CC(O)CC3c2ccc(F)cc2)ccc1-n1cnc(Cl)c1",
"routeLength": 7,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_1cf7513966e88d2e13a9abd7",
"inchikey": "ISBVQXLOOBKUBH-UHFFFAOYSA-N",
"smiles": "COc1cc(Nc2nc3c(s2)CC(O)CC3c2ccc(F)cc2)ccc1-n1cnc(Cl)c1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "13060",
"routeId": "sa_6b51f82090175c05ac9bf7a8",
"moleculeId": "sa_1cf7513966e88d2e13a9abd7",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_1cf7513966e88d2e13a9abd7",
"inchikey": "ISBVQXLOOBKUBH-UHFFFAOYSA-N",
"smiles": "COc1cc(Nc2nc3c(s2)CC(O)CC3c2ccc(F)cc2)ccc1-n1cnc(Cl)c1"
},
"smiles": "COc1cc(Nc2nc3c(s2)CC(O)CC3c2ccc(F)cc2)ccc1-n1cnc(Cl)c1",
"reactionStepId": "sa_3119a6a299ea80f98c1b362a",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08349880B2;0546;1271357\",\"rsmi\":\"[CH3:1][O:2][c:3]1[c:4](-[n:5]2[cH:6][n:7][c:8]([Cl:9])[cH:10]2)[cH:11][cH:12][c:13]([NH:14][c:15]2[n:16][c:17]3[c:18]([s:31]2)[CH2:19][C:20](=[O:21])[CH2:22][CH:23]3[c:24]2[cH:25][cH:26][c:27]([F:28])[cH:29][cH:30]2)[cH:32]1>CO.B.[Na+]>[CH3:1][O:2][c:3]1[c:4](-[n:5]2[cH:6][n:7][c:8]([Cl:9])[cH:10]2)[cH:11][cH:12][c:13]([NH:14][c:15]2[n:16][c:17]3[c:18]([s:31]2)[CH2:19][CH:20]([OH:21])[CH2:22][CH:23]3[c:24]2[cH:25][cH:26][c:27]([F:28])[cH:29][cH:30]2)[cH:32]1\"},\"mapped_reaction_smiles\":\"[CH3:1][O:2][c:3]1[c:4](-[n:5]2[cH:6][n:7][c:8]([Cl:9])[cH:10]2)[cH:11][cH:12][c:13]([NH:14][c:15]2[n:16][c:17]3[c:18]([s:31]2)[CH2:19][C:20](=[O:21])[CH2:22][CH:23]3[c:24]2[cH:25][cH:26][c:27]([F:28])[cH:29][cH:30]2)[cH:32]1>CO.B.[Na+]>[CH3:1][O:2][c:3]1[c:4](-[n:5]2[cH:6][n:7][c:8]([Cl:9])[cH:10]2)[cH:11][cH:12][c:13]([NH:14][c:15]2[n:16][c:17]3[c:18]([s:31]2)[CH2:19][CH:20]([OH:21])[CH2:22][CH:23]3[c:24]2[cH:25][cH:26][c:27]([F:28])[cH:29][cH:30]2)[cH:32]1\"}",
"reactionStep": {
"id": "sa_3119a6a299ea80f98c1b362a",
"reactionHash": "1a80a4b6bda94c7d84ff16d8f89438dfad05614d4f50959af459117b5dc55a33"
},
"children": [
{
"id": "13061",
"routeId": "sa_6b51f82090175c05ac9bf7a8",
"moleculeId": "sa_dbc09a9a3dadb6e1159e7f82",
"parentId": "13060",
"isLeaf": false,
"molecule": {
"id": "sa_dbc09a9a3dadb6e1159e7f82",
"inchikey": "PWQALHLQPZRKGS-UHFFFAOYSA-N",
"smiles": "COc1cc(Nc2nc3c(s2)CC(=O)CC3c2ccc(F)cc2)ccc1-n1cnc(Cl)c1"
},
"smiles": "COc1cc(Nc2nc3c(s2)CC(=O)CC3c2ccc(F)cc2)ccc1-n1cnc(Cl)c1",
"reactionStepId": "sa_310e6fe7242a25b254cb5969",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08349880B2;0544;1271356\",\"rsmi\":\"C1C[O:21][C:20]2(O1)[CH2:19][c:18]1[c:17]([n:16][c:15]([NH:14][c:13]3[cH:12][cH:11][c:4](-[n:5]4[cH:6][n:7][c:8]([Cl:9])[cH:10]4)[c:3]([O:2][CH3:1])[cH:32]3)[s:31]1)[CH:23]([c:24]1[cH:25][cH:26][c:27]([F:28])[cH:29][cH:30]1)[CH2:22]2>CC(C)=O.Cl>[CH3:1][O:2][c:3]1[c:4](-[n:5]2[cH:6][n:7][c:8]([Cl:9])[cH:10]2)[cH:11][cH:12][c:13]([NH:14][c:15]2[n:16][c:17]3[c:18]([s:31]2)[CH2:19][C:20](=[O:21])[CH2:22][CH:23]3[c:24]2[cH:25][cH:26][c:27]([F:28])[cH:29][cH:30]2)[cH:32]1\"},\"mapped_reaction_smiles\":\"C1C[O:21][C:20]2(O1)[CH2:19][c:18]1[c:17]([n:16][c:15]([NH:14][c:13]3[cH:12][cH:11][c:4](-[n:5]4[cH:6][n:7][c:8]([Cl:9])[cH:10]4)[c:3]([O:2][CH3:1])[cH:32]3)[s:31]1)[CH:23]([c:24]1[cH:25][cH:26][c:27]([F:28])[cH:29][cH:30]1)[CH2:22]2>CC(C)=O.Cl>[CH3:1][O:2][c:3]1[c:4](-[n:5]2[cH:6][n:7][c:8]([Cl:9])[cH:10]2)[cH:11][cH:12][c:13]([NH:14][c:15]2[n:16][c:17]3[c:18]([s:31]2)[CH2:19][C:20](=[O:21])[CH2:22][CH:23]3[c:24]2[cH:25][cH:26][c:27]([F:28])[cH:29][cH:30]2)[cH:32]1\"}",
"reactionStep": {
"id": "sa_310e6fe7242a25b254cb5969",
"reactionHash": "05f88f8b41221e65c9f401c9567e1174fcee9448249ba654f445e89bd53633d1"
},
"children": [
{
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"routeId": "sa_6b51f82090175c05ac9bf7a8",
"moleculeId": "sa_1a280375041105e25cb5866b",
"parentId": "13061",
"isLeaf": false,
"molecule": {
"id": "sa_1a280375041105e25cb5866b",
"inchikey": "KMTPJENVGCZJKH-UHFFFAOYSA-N",
"smiles": "COc1cc(Nc2nc3c(s2)CC2(CC3c3ccc(F)cc3)OCCO2)ccc1-n1cnc(Cl)c1"
},
"smiles": "COc1cc(Nc2nc3c(s2)CC2(CC3c3ccc(F)cc3)OCCO2)ccc1-n1cnc(Cl)c1",
"reactionStepId": "sa_7bb76769541568f1c5007b7f",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08349880B2;0542;1271355\",\"rsmi\":\"O=[C:17]1[CH:18](Br)[CH2:19][C:20]2([CH2:21][CH:22]1[c:23]1[cH:24][cH:25][c:26]([F:27])[cH:28][cH:29]1)[O:30][CH2:31][CH2:32][O:33]2.[CH3:1][O:2][c:3]1[c:4](-[n:5]2[cH:6][n:7][c:8]([Cl:9])[cH:10]2)[cH:11][cH:12][c:13]([NH:14][C:15]([NH2:16])=[S:34])[cH:35]1>CCO.CCOC(C)=O>[CH3:1][O:2][c:3]1[c:4](-[n:5]2[cH:6][n:7][c:8]([Cl:9])[cH:10]2)[cH:11][cH:12][c:13]([NH:14][c:15]2[n:16][c:17]3[c:18]([s:34]2)[CH2:19][C:20]2([CH2:21][CH:22]3[c:23]3[cH:24][cH:25][c:26]([F:27])[cH:28][cH:29]3)[O:30][CH2:31][CH2:32][O:33]2)[cH:35]1\"},\"mapped_reaction_smiles\":\"O=[C:17]1[CH:18](Br)[CH2:19][C:20]2([CH2:21][CH:22]1[c:23]1[cH:24][cH:25][c:26]([F:27])[cH:28][cH:29]1)[O:30][CH2:31][CH2:32][O:33]2.[CH3:1][O:2][c:3]1[c:4](-[n:5]2[cH:6][n:7][c:8]([Cl:9])[cH:10]2)[cH:11][cH:12][c:13]([NH:14][C:15]([NH2:16])=[S:34])[cH:35]1>CCO.CCOC(C)=O>[CH3:1][O:2][c:3]1[c:4](-[n:5]2[cH:6][n:7][c:8]([Cl:9])[cH:10]2)[cH:11][cH:12][c:13]([NH:14][c:15]2[n:16][c:17]3[c:18]([s:34]2)[CH2:19][C:20]2([CH2:21][CH:22]3[c:23]3[cH:24][cH:25][c:26]([F:27])[cH:28][cH:29]3)[O:30][CH2:31][CH2:32][O:33]2)[cH:35]1\"}",
"reactionStep": {
"id": "sa_7bb76769541568f1c5007b7f",
"reactionHash": "d2a382deed0704606f2b15ad68f9d29ede44bae8fba7942b1a8af0a7046ea77d"
},
"children": [
{
"id": "13063",
"routeId": "sa_6b51f82090175c05ac9bf7a8",
"moleculeId": "sa_950db56413f243385ac2ebba",
"parentId": "13062",
"isLeaf": true,
"molecule": {
"id": "sa_950db56413f243385ac2ebba",
"inchikey": "PFCNBNJFKHHSSH-UHFFFAOYSA-N",
"smiles": "O=C1C(Br)CC2(CC1c1ccc(F)cc1)OCCO2"
},
"smiles": "O=C1C(Br)CC2(CC1c1ccc(F)cc1)OCCO2",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "13064",
"routeId": "sa_6b51f82090175c05ac9bf7a8",
"moleculeId": "sa_c200728d8f25e70e353fd46b",
"parentId": "13062",
"isLeaf": false,
"molecule": {
"id": "sa_c200728d8f25e70e353fd46b",
"inchikey": "RTXIHWAOZIMHHE-UHFFFAOYSA-N",
"smiles": "COc1cc(NC(N)=S)ccc1-n1cnc(Cl)c1"
},
"smiles": "COc1cc(NC(N)=S)ccc1-n1cnc(Cl)c1",
"reactionStepId": "sa_1058cc65ed98a74310ec94ca",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08349880B2;0159;1271194\",\"rsmi\":\"[CH3:1][O:2][c:3]1[c:4](-[n:5]2[cH:6][n:7][c:8]([Cl:9])[cH:10]2)[cH:11][cH:12][c:13]([N:14]=[C:15]=[S:17])[cH:18]1.[NH3:16]>>[CH3:1][O:2][c:3]1[c:4](-[n:5]2[cH:6][n:7][c:8]([Cl:9])[cH:10]2)[cH:11][cH:12][c:13]([NH:14][C:15]([NH2:16])=[S:17])[cH:18]1\"},\"mapped_reaction_smiles\":\"[CH3:1][O:2][c:3]1[c:4](-[n:5]2[cH:6][n:7][c:8]([Cl:9])[cH:10]2)[cH:11][cH:12][c:13]([N:14]=[C:15]=[S:17])[cH:18]1.[NH3:16]>>[CH3:1][O:2][c:3]1[c:4](-[n:5]2[cH:6][n:7][c:8]([Cl:9])[cH:10]2)[cH:11][cH:12][c:13]([NH:14][C:15]([NH2:16])=[S:17])[cH:18]1\"}",
"reactionStep": {
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"reactionHash": "bd9c31673ff6dbb02bf3188fcac993110063fc7f7602403f4768248ed56c4371"
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"children": [
{
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"routeId": "sa_6b51f82090175c05ac9bf7a8",
"moleculeId": "sa_11f14902a1805590b4eb443b",
"parentId": "13064",
"isLeaf": false,
"molecule": {
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"inchikey": "JVLDMJKGIJFXOJ-UHFFFAOYSA-N",
"smiles": "COc1cc(N=C=S)ccc1-n1cnc(Cl)c1"
},
"smiles": "COc1cc(N=C=S)ccc1-n1cnc(Cl)c1",
"reactionStepId": "sa_aabdf01741b0e64f8edb47fe",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08349880B2;0158;1271193\",\"rsmi\":\"O=c1ccccn1[C:15](n1ccccc1=O)=[S:16].[CH3:1][O:2][c:3]1[c:4](-[n:5]2[cH:6][n:7][c:8]([Cl:9])[cH:10]2)[cH:11][cH:12][c:13]([NH2:14])[cH:17]1>ClCCl>[CH3:1][O:2][c:3]1[c:4](-[n:5]2[cH:6][n:7][c:8]([Cl:9])[cH:10]2)[cH:11][cH:12][c:13]([N:14]=[C:15]=[S:16])[cH:17]1\"},\"mapped_reaction_smiles\":\"O=c1ccccn1[C:15](n1ccccc1=O)=[S:16].[CH3:1][O:2][c:3]1[c:4](-[n:5]2[cH:6][n:7][c:8]([Cl:9])[cH:10]2)[cH:11][cH:12][c:13]([NH2:14])[cH:17]1>ClCCl>[CH3:1][O:2][c:3]1[c:4](-[n:5]2[cH:6][n:7][c:8]([Cl:9])[cH:10]2)[cH:11][cH:12][c:13]([N:14]=[C:15]=[S:16])[cH:17]1\"}",
"reactionStep": {
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"reactionHash": "2bdad5e31a82d6c40f3e457e9dccdea91ce5093c7cddd3d6a169ad4a12158d9b"
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"children": [
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"molecule": {
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"inchikey": "DJCLJGKHLXTVTR-UHFFFAOYSA-N",
"smiles": "COc1cc(N)ccc1-n1cnc(Cl)c1"
},
"smiles": "COc1cc(N)ccc1-n1cnc(Cl)c1",
"reactionStepId": "sa_cb83030b4ac8ef8dab42ce83",
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"metadata": "{\"annotations\":{\"ID\":\"US08349880B2;0157;1271192\",\"rsmi\":\"O=[N+:14]([O-])[c:13]1[cH:12][cH:11][c:4](-[n:5]2[cH:6][n:7][c:8]([Cl:9])[cH:10]2)[c:3]([O:2][CH3:1])[cH:15]1>CC(=O)O.CCO.O.[Fe].[Na+].O>[CH3:1][O:2][c:3]1[c:4](-[n:5]2[cH:6][n:7][c:8]([Cl:9])[cH:10]2)[cH:11][cH:12][c:13]([NH2:14])[cH:15]1\"},\"mapped_reaction_smiles\":\"O=[N+:14]([O-])[c:13]1[cH:12][cH:11][c:4](-[n:5]2[cH:6][n:7][c:8]([Cl:9])[cH:10]2)[c:3]([O:2][CH3:1])[cH:15]1>CC(=O)O.CCO.O.[Fe].[Na+].O>[CH3:1][O:2][c:3]1[c:4](-[n:5]2[cH:6][n:7][c:8]([Cl:9])[cH:10]2)[cH:11][cH:12][c:13]([NH2:14])[cH:15]1\"}",
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"smiles": "COc1cc([N+](=O)[O-])ccc1-n1cnc(Cl)c1",
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"metadata": "{\"annotations\":{\"ID\":\"US08349880B2;0156;1271191\",\"rsmi\":\"Cl[c:4]1[c:3]([O:2][CH3:1])[cH:17][c:13]([N+:14](=[O:15])[O-:16])[cH:12][cH:11]1.[nH:5]1[cH:6][n:7][c:8]([Cl:9])[cH:10]1>CS(C)=O.O.[K+].O>[CH3:1][O:2][c:3]1[c:4](-[n:5]2[cH:6][n:7][c:8]([Cl:9])[cH:10]2)[cH:11][cH:12][c:13]([N+:14](=[O:15])[O-:16])[cH:17]1\"},\"mapped_reaction_smiles\":\"Cl[c:4]1[c:3]([O:2][CH3:1])[cH:17][c:13]([N+:14](=[O:15])[O-:16])[cH:12][cH:11]1.[nH:5]1[cH:6][n:7][c:8]([Cl:9])[cH:10]1>CS(C)=O.O.[K+].O>[CH3:1][O:2][c:3]1[c:4](-[n:5]2[cH:6][n:7][c:8]([Cl:9])[cH:10]2)[cH:11][cH:12][c:13]([N+:14](=[O:15])[O-:16])[cH:17]1\"}",
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"molecule": {
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"inchikey": "BQRBAXFOPZRMCU-UHFFFAOYSA-N",
"smiles": "Clc1cnc[nH]1"
},
"smiles": "Clc1c[nH]cn1",
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{
"id": "13069",
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"molecule": {
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"inchikey": "JXIJUAWSDBACEB-UHFFFAOYSA-N",
"smiles": "COc1cc([N+](=O)[O-])ccc1Cl"
},
"smiles": "COc1cc([N+](=O)[O-])ccc1Cl",
"reactionStepId": null,
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}
]
}
]
},
{
"id": "13070",
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"molecule": {
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"inchikey": "KXMMNJQMGILZDB-UHFFFAOYSA-N",
"smiles": "O=c1ccccn1C(=S)n1ccccc1=O"
},
"smiles": "O=c1ccccn1C(=S)n1ccccc1=O",
"reactionStepId": null,
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}
]
},
{
"id": "13071",
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"moleculeId": "sa_c9679fdd876f32f86b77fb69",
"parentId": "13064",
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"molecule": {
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"inchikey": "QGZKDVFQNNGYKY-UHFFFAOYSA-N",
"smiles": "N"
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