Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
COC(=O)CCS(=O)(=O)N1CC=C(c2ccc3nc(OC4CCN(c5nc(C(C)C)no5)CC4)sc3c2)CC1
InChiKey
QXIHLDOPXPICQQ-UHFFFAOYSA-N
Route Signature
9c6ddba5ca97f073240c4b67a898ec909c0fc5516fdf4290f969c76b734971f5
Synthesis route with 6 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_43eab34896d177ba57bd9e40",
"signature": "9c6ddba5ca97f073240c4b67a898ec909c0fc5516fdf4290f969c76b734971f5",
"contentHash": "7294beb9026372cf6e354a53b811af4dbd45a1d366354dfd78d08edcda1a8d1b",
"length": 6,
"isConvergent": false
},
"target": {
"id": "sa_f2bc1a40ef4e0054af5b8793",
"benchmarkSetId": "f925e688d731a0ad4e3aa6a505df094f6d3ca64ce3facc312bc5f64731921b33",
"targetId": "n5-00255",
"moleculeId": "sa_30a7ed8b6e89e80daf95c02c",
"smiles": "COC(=O)CCS(=O)(=O)N1CC=C(c2ccc3nc(OC4CCN(c5nc(C(C)C)no5)CC4)sc3c2)CC1",
"routeLength": 6,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_30a7ed8b6e89e80daf95c02c",
"inchikey": "QXIHLDOPXPICQQ-UHFFFAOYSA-N",
"smiles": "COC(=O)CCS(=O)(=O)N1CC=C(c2ccc3nc(OC4CCN(c5nc(C(C)C)no5)CC4)sc3c2)CC1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 2
},
"rootNode": {
"id": "3722",
"routeId": "sa_43eab34896d177ba57bd9e40",
"moleculeId": "sa_30a7ed8b6e89e80daf95c02c",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_30a7ed8b6e89e80daf95c02c",
"inchikey": "QXIHLDOPXPICQQ-UHFFFAOYSA-N",
"smiles": "COC(=O)CCS(=O)(=O)N1CC=C(c2ccc3nc(OC4CCN(c5nc(C(C)C)no5)CC4)sc3c2)CC1"
},
"smiles": "COC(=O)CCS(=O)(=O)N1CC=C(c2ccc3nc(OC4CCN(c5nc(C(C)C)no5)CC4)sc3c2)CC1",
"reactionStepId": "sa_7401ad0b9dc2a0f4223e44b0",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130053345A1;0528;1337541\",\"rsmi\":\"Cl[S:7]([CH2:6][CH2:5][C:3]([O:2][CH3:1])=[O:4])(=[O:8])=[O:9].[NH:10]1[CH2:11][CH:12]=[C:13]([c:14]2[cH:15][c:16]3[c:17]([cH:18][cH:19]2)[n:20][c:21]([O:22][CH:23]2[CH2:24][CH2:25][N:26]([c:27]4[n:28][c:29]([CH:30]([CH3:31])[CH3:32])[n:33][o:34]4)[CH2:35][CH2:36]2)[s:37]3)[CH2:38][CH2:39]1>CCN(CC)CC.ClCCl>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][S:7](=[O:8])(=[O:9])[N:10]1[CH2:11][CH:12]=[C:13]([c:14]2[cH:15][c:16]3[c:17]([cH:18][cH:19]2)[n:20][c:21]([O:22][CH:23]2[CH2:24][CH2:25][N:26]([c:27]4[n:28][c:29]([CH:30]([CH3:31])[CH3:32])[n:33][o:34]4)[CH2:35][CH2:36]2)[s:37]3)[CH2:38][CH2:39]1\"},\"mapped_reaction_smiles\":\"Cl[S:7]([CH2:6][CH2:5][C:3]([O:2][CH3:1])=[O:4])(=[O:8])=[O:9].[NH:10]1[CH2:11][CH:12]=[C:13]([c:14]2[cH:15][c:16]3[c:17]([cH:18][cH:19]2)[n:20][c:21]([O:22][CH:23]2[CH2:24][CH2:25][N:26]([c:27]4[n:28][c:29]([CH:30]([CH3:31])[CH3:32])[n:33][o:34]4)[CH2:35][CH2:36]2)[s:37]3)[CH2:38][CH2:39]1>CCN(CC)CC.ClCCl>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][S:7](=[O:8])(=[O:9])[N:10]1[CH2:11][CH:12]=[C:13]([c:14]2[cH:15][c:16]3[c:17]([cH:18][cH:19]2)[n:20][c:21]([O:22][CH:23]2[CH2:24][CH2:25][N:26]([c:27]4[n:28][c:29]([CH:30]([CH3:31])[CH3:32])[n:33][o:34]4)[CH2:35][CH2:36]2)[s:37]3)[CH2:38][CH2:39]1\"}",
"reactionStep": {
"id": "sa_7401ad0b9dc2a0f4223e44b0",
"reactionHash": "7814fcd73c6c9fda1dd341f4f5194dfedb3b9d0f2879e1b973fade0d4511f0c0"
},
"children": [
{
"id": "3723",
"routeId": "sa_43eab34896d177ba57bd9e40",
"moleculeId": "sa_45ac7d4ad51a1323ed724a7c",
"parentId": "3722",
"isLeaf": true,
"molecule": {
"id": "sa_45ac7d4ad51a1323ed724a7c",
"inchikey": "LWJZGJNMJBUUMC-UHFFFAOYSA-N",
"smiles": "COC(=O)CCS(=O)(=O)Cl"
},
"smiles": "COC(=O)CCS(=O)(=O)Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "3724",
"routeId": "sa_43eab34896d177ba57bd9e40",
"moleculeId": "sa_973584466640f46b751c9625",
"parentId": "3722",
"isLeaf": false,
"molecule": {
"id": "sa_973584466640f46b751c9625",
"inchikey": "QVXPKIOOAOTRHX-UHFFFAOYSA-N",
"smiles": "CC(C)c1noc(N2CCC(Oc3nc4ccc(C5=CCNCC5)cc4s3)CC2)n1"
},
"smiles": "CC(C)c1noc(N2CCC(Oc3nc4ccc(C5=CCNCC5)cc4s3)CC2)n1",
"reactionStepId": "sa_8f2d0a180f5ec1304bb64f0a",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130053345A1;0524;1337539\",\"rsmi\":\"CC(C)(C)OC(=O)[N:22]1[CH2:21][CH:20]=[C:19]([c:18]2[cH:17][c:16]3[c:15]([n:14][c:13]([O:12][CH:11]4[CH2:10][CH2:9][N:8]([c:7]5[o:6][n:5][c:4]([CH:2]([CH3:1])[CH3:3])[n:30]5)[CH2:29][CH2:28]4)[s:27]3)[cH:26][cH:25]2)[CH2:24][CH2:23]1>ClCCl.O=C(O)C(F)(F)F>[CH3:1][CH:2]([CH3:3])[c:4]1[n:5][o:6][c:7]([N:8]2[CH2:9][CH2:10][CH:11]([O:12][c:13]3[n:14][c:15]4[c:16]([cH:17][c:18]([C:19]5=[CH:20][CH2:21][NH:22][CH2:23][CH2:24]5)[cH:25][cH:26]4)[s:27]3)[CH2:28][CH2:29]2)[n:30]1\"},\"mapped_reaction_smiles\":\"CC(C)(C)OC(=O)[N:22]1[CH2:21][CH:20]=[C:19]([c:18]2[cH:17][c:16]3[c:15]([n:14][c:13]([O:12][CH:11]4[CH2:10][CH2:9][N:8]([c:7]5[o:6][n:5][c:4]([CH:2]([CH3:1])[CH3:3])[n:30]5)[CH2:29][CH2:28]4)[s:27]3)[cH:26][cH:25]2)[CH2:24][CH2:23]1>ClCCl.O=C(O)C(F)(F)F>[CH3:1][CH:2]([CH3:3])[c:4]1[n:5][o:6][c:7]([N:8]2[CH2:9][CH2:10][CH:11]([O:12][c:13]3[n:14][c:15]4[c:16]([cH:17][c:18]([C:19]5=[CH:20][CH2:21][NH:22][CH2:23][CH2:24]5)[cH:25][cH:26]4)[s:27]3)[CH2:28][CH2:29]2)[n:30]1\"}",
"reactionStep": {
"id": "sa_8f2d0a180f5ec1304bb64f0a",
"reactionHash": "0d78af158546c2341217ab77c5628a4c1067c747e9d67a6249f8656999302ca6"
},
"children": [
{
"id": "3725",
"routeId": "sa_43eab34896d177ba57bd9e40",
"moleculeId": "sa_13be7c307ef1578d99d58b3c",
"parentId": "3724",
"isLeaf": false,
"molecule": {
"id": "sa_13be7c307ef1578d99d58b3c",
"inchikey": "FLUICOIEXKPSKA-UHFFFAOYSA-N",
"smiles": "CC(C)c1noc(N2CCC(Oc3nc4ccc(C5=CCN(C(=O)OC(C)(C)C)CC5)cc4s3)CC2)n1"
},
"smiles": "CC(C)c1noc(N2CCC(Oc3nc4ccc(C5=CCN(C(=O)OC(C)(C)C)CC5)cc4s3)CC2)n1",
"reactionStepId": "sa_5b25d15d8afb3ba58b7141ba",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130053345A1;0522;1337538\",\"rsmi\":\"Br[c:18]1[cH:17][c:16]2[c:15]([n:14][c:13]([O:12][CH:11]3[CH2:10][CH2:9][N:8]([c:7]4[o:6][n:5][c:4]([CH:2]([CH3:1])[CH3:3])[n:37]4)[CH2:36][CH2:35]3)[s:34]2)[cH:33][cH:32]1.CC1(C)OB([C:19]2=[CH:20][CH2:21][N:22]([C:23](=[O:24])[O:25][C:26]([CH3:27])([CH3:28])[CH3:29])[CH2:30][CH2:31]2)OC1(C)C>C1COCCO1.O.O=C(O)O.[K+].[K+].c1ccc([PH](c2ccccc2)(c2ccccc2)[Pd]([PH](c2ccccc2)(c2ccccc2)c2ccccc2)([PH](c2ccccc2)(c2ccccc2)c2ccccc2)[PH](c2ccccc2)(c2ccccc2)c2ccccc2)cc1>[CH3:1][CH:2]([CH3:3])[c:4]1[n:5][o:6][c:7]([N:8]2[CH2:9][CH2:10][CH:11]([O:12][c:13]3[n:14][c:15]4[c:16]([cH:17][c:18]([C:19]5=[CH:20][CH2:21][N:22]([C:23](=[O:24])[O:25][C:26]([CH3:27])([CH3:28])[CH3:29])[CH2:30][CH2:31]5)[cH:32][cH:33]4)[s:34]3)[CH2:35][CH2:36]2)[n:37]1\"},\"mapped_reaction_smiles\":\"Br[c:18]1[cH:17][c:16]2[c:15]([n:14][c:13]([O:12][CH:11]3[CH2:10][CH2:9][N:8]([c:7]4[o:6][n:5][c:4]([CH:2]([CH3:1])[CH3:3])[n:37]4)[CH2:36][CH2:35]3)[s:34]2)[cH:33][cH:32]1.CC1(C)OB([C:19]2=[CH:20][CH2:21][N:22]([C:23](=[O:24])[O:25][C:26]([CH3:27])([CH3:28])[CH3:29])[CH2:30][CH2:31]2)OC1(C)C>C1COCCO1.O.O=C(O)O.[K+].[K+].c1ccc([PH](c2ccccc2)(c2ccccc2)[Pd]([PH](c2ccccc2)(c2ccccc2)c2ccccc2)([PH](c2ccccc2)(c2ccccc2)c2ccccc2)[PH](c2ccccc2)(c2ccccc2)c2ccccc2)cc1>[CH3:1][CH:2]([CH3:3])[c:4]1[n:5][o:6][c:7]([N:8]2[CH2:9][CH2:10][CH:11]([O:12][c:13]3[n:14][c:15]4[c:16]([cH:17][c:18]([C:19]5=[CH:20][CH2:21][N:22]([C:23](=[O:24])[O:25][C:26]([CH3:27])([CH3:28])[CH3:29])[CH2:30][CH2:31]5)[cH:32][cH:33]4)[s:34]3)[CH2:35][CH2:36]2)[n:37]1\"}",
"reactionStep": {
"id": "sa_5b25d15d8afb3ba58b7141ba",
"reactionHash": "1dc60c02683358f2ce4e68cdce500fd0c958cb224918b211eb78df9bf998f77d"
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"children": [
{
"id": "3726",
"routeId": "sa_43eab34896d177ba57bd9e40",
"moleculeId": "sa_356dc388b0c8aecba726dc02",
"parentId": "3725",
"isLeaf": true,
"molecule": {
"id": "sa_356dc388b0c8aecba726dc02",
"inchikey": "VVDCRJGWILREQH-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)N1CC=C(B2OC(C)(C)C(C)(C)O2)CC1"
},
"smiles": "CC(C)(C)OC(=O)N1CC=C(B2OC(C)(C)C(C)(C)O2)CC1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "3727",
"routeId": "sa_43eab34896d177ba57bd9e40",
"moleculeId": "sa_b7968fd6a160856b2767dfe9",
"parentId": "3725",
"isLeaf": false,
"molecule": {
"id": "sa_b7968fd6a160856b2767dfe9",
"inchikey": "XHKTUUFPESCORE-UHFFFAOYSA-N",
"smiles": "CC(C)c1noc(N2CCC(Oc3nc4ccc(Br)cc4s3)CC2)n1"
},
"smiles": "CC(C)c1noc(N2CCC(Oc3nc4ccc(Br)cc4s3)CC2)n1",
"reactionStepId": "sa_88c2eedc379a88496576ad7e",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130053345A1;0520;1337537\",\"rsmi\":\"Cl[c:13]1[n:14][c:15]2[c:16]([cH:17][c:18]([Br:19])[cH:20][cH:21]2)[s:22]1.[CH3:1][CH:2]([CH3:3])[c:4]1[n:5][o:6][c:7]([N:8]2[CH2:9][CH2:10][CH:11]([OH:12])[CH2:23][CH2:24]2)[n:25]1>C1CCOC1.O.[HH].[Na+]>[CH3:1][CH:2]([CH3:3])[c:4]1[n:5][o:6][c:7]([N:8]2[CH2:9][CH2:10][CH:11]([O:12][c:13]3[n:14][c:15]4[c:16]([cH:17][c:18]([Br:19])[cH:20][cH:21]4)[s:22]3)[CH2:23][CH2:24]2)[n:25]1\"},\"mapped_reaction_smiles\":\"Cl[c:13]1[n:14][c:15]2[c:16]([cH:17][c:18]([Br:19])[cH:20][cH:21]2)[s:22]1.[CH3:1][CH:2]([CH3:3])[c:4]1[n:5][o:6][c:7]([N:8]2[CH2:9][CH2:10][CH:11]([OH:12])[CH2:23][CH2:24]2)[n:25]1>C1CCOC1.O.[HH].[Na+]>[CH3:1][CH:2]([CH3:3])[c:4]1[n:5][o:6][c:7]([N:8]2[CH2:9][CH2:10][CH:11]([O:12][c:13]3[n:14][c:15]4[c:16]([cH:17][c:18]([Br:19])[cH:20][cH:21]4)[s:22]3)[CH2:23][CH2:24]2)[n:25]1\"}",
"reactionStep": {
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"reactionHash": "9dfb3970030161a3cfa3a70c53bf7a62e1990a4f6ec47d0bb0efe427e7df57d8"
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"children": [
{
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"moleculeId": "sa_ef3fe1c317e96c955f32c3f7",
"parentId": "3727",
"isLeaf": true,
"molecule": {
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"inchikey": "IJQSMNIZBBEBKI-UHFFFAOYSA-N",
"smiles": "Clc1nc2ccc(Br)cc2s1"
},
"smiles": "Clc1nc2ccc(Br)cc2s1",
"reactionStepId": null,
"template": null,
"metadata": null,
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},
{
"id": "3729",
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"moleculeId": "sa_f72bff9ef034bb12a4950a7b",
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"molecule": {
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"inchikey": "SNAOGTUJDXPNEK-UHFFFAOYSA-N",
"smiles": "CC(C)c1noc(N2CCC(O)CC2)n1"
},
"smiles": "CC(C)c1noc(N2CCC(O)CC2)n1",
"reactionStepId": "sa_57ddde2a28eba749a7522448",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130053345A1;0518;1337536\",\"rsmi\":\"N#[C:7][N:8]1[CH2:9][CH2:10][CH:11]([OH:12])[CH2:13][CH2:14]1.[CH3:1][CH:2]([CH3:3])[C:4]([NH:5][OH:6])=[NH:15]>CCO.CCOC(C)=O.Cl.Cl.Cl.[Zn+2]>[CH3:1][CH:2]([CH3:3])[c:4]1[n:5][o:6][c:7]([N:8]2[CH2:9][CH2:10][CH:11]([OH:12])[CH2:13][CH2:14]2)[n:15]1\"},\"mapped_reaction_smiles\":\"N#[C:7][N:8]1[CH2:9][CH2:10][CH:11]([OH:12])[CH2:13][CH2:14]1.[CH3:1][CH:2]([CH3:3])[C:4]([NH:5][OH:6])=[NH:15]>CCO.CCOC(C)=O.Cl.Cl.Cl.[Zn+2]>[CH3:1][CH:2]([CH3:3])[c:4]1[n:5][o:6][c:7]([N:8]2[CH2:9][CH2:10][CH:11]([OH:12])[CH2:13][CH2:14]2)[n:15]1\"}",
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"children": [
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"molecule": {
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"inchikey": "JHRDEHLFNLLCQS-UHFFFAOYSA-N",
"smiles": "CC(C)C(N)=NO"
},
"smiles": "CC(C)C(=N)NO",
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{
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"smiles": "N#CN1CCC(O)CC1",
"reactionStepId": "sa_9cfd82795e0578db685de000",
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"metadata": "{\"annotations\":{\"ID\":\"US20130053345A1;0516;1337535\",\"rsmi\":\"Br[C:2]#[N:1].[NH:3]1[CH2:4][CH2:5][CH:6]([OH:7])[CH2:8][CH2:9]1>ClCCl.O.O=C(O)O.O=C(O)O.O=S(=O)(O)O.[Mg+2].[Na+].[Na+].[Na+]>[N:1]#[C:2][N:3]1[CH2:4][CH2:5][CH:6]([OH:7])[CH2:8][CH2:9]1\"},\"mapped_reaction_smiles\":\"Br[C:2]#[N:1].[NH:3]1[CH2:4][CH2:5][CH:6]([OH:7])[CH2:8][CH2:9]1>ClCCl.O.O=C(O)O.O=C(O)O.O=S(=O)(O)O.[Mg+2].[Na+].[Na+].[Na+]>[N:1]#[C:2][N:3]1[CH2:4][CH2:5][CH:6]([OH:7])[CH2:8][CH2:9]1\"}",
"reactionStep": {
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"children": [
{
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"smiles": "N#CBr"
},
"smiles": "N#CBr",
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},
{
"id": "3733",
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"molecule": {
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}
]
}
]
}
]
}
]
}
]
}
]
}
}