Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CN(Cc1cc2ccccc2n1C)C(=O)/C=C/c1ccc(N2C(=O)c3ccccc3C2=O)nc1
InChiKey
GIHWREOVDNTGSD-WYMLVPIESA-N
Route Signature
5d66d5632f20dc17228a844fcae5e026a4cdfa25c73e1cd37187fd92a11b072c
Synthesis route with 5 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_7a7229e164de53373423803e",
"signature": "5d66d5632f20dc17228a844fcae5e026a4cdfa25c73e1cd37187fd92a11b072c",
"contentHash": "c93ea2e4f52d4f042adf628d8f40717f4cae9d3148d996d864d092264c96381b",
"length": 5,
"isConvergent": true
},
"target": {
"id": "sa_5d4b70a548d9bedc3830198e",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-00598",
"moleculeId": "sa_6e69b915efee849f66cba311",
"smiles": "CN(Cc1cc2ccccc2n1C)C(=O)/C=C/c1ccc(N2C(=O)c3ccccc3C2=O)nc1",
"routeLength": 5,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_6e69b915efee849f66cba311",
"inchikey": "GIHWREOVDNTGSD-WYMLVPIESA-N",
"smiles": "CN(Cc1cc2ccccc2n1C)C(=O)/C=C/c1ccc(N2C(=O)c3ccccc3C2=O)nc1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "9587",
"routeId": "sa_7a7229e164de53373423803e",
"moleculeId": "sa_6e69b915efee849f66cba311",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_6e69b915efee849f66cba311",
"inchikey": "GIHWREOVDNTGSD-WYMLVPIESA-N",
"smiles": "CN(Cc1cc2ccccc2n1C)C(=O)/C=C/c1ccc(N2C(=O)c3ccccc3C2=O)nc1"
},
"smiles": "CN(Cc1cc2ccccc2n1C)C(=O)/C=C/c1ccc(N2C(=O)c3ccccc3C2=O)nc1",
"reactionStepId": "sa_c0e1fe2dfd669d3ed030171d",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20090275572A1;0288;786138\",\"rsmi\":\"O1[C:23](=[O:24])[c:25]2[cH:26][cH:27][cH:28][cH:29][c:30]2[C:31]1=[O:32].[CH3:1][N:2]([CH2:3][c:4]1[cH:5][c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[n:12]1[CH3:13])[C:14](=[O:15])/[CH:16]=[CH:17]/[c:18]1[cH:19][cH:20][c:21]([NH2:22])[n:33][cH:34]1>C1CCOC1.O=C(O)O.[Na+]>[CH3:1][N:2]([CH2:3][c:4]1[cH:5][c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[n:12]1[CH3:13])[C:14](=[O:15])/[CH:16]=[CH:17]/[c:18]1[cH:19][cH:20][c:21]([N:22]2[C:23](=[O:24])[c:25]3[cH:26][cH:27][cH:28][cH:29][c:30]3[C:31]2=[O:32])[n:33][cH:34]1\"},\"mapped_reaction_smiles\":\"O1[C:23](=[O:24])[c:25]2[cH:26][cH:27][cH:28][cH:29][c:30]2[C:31]1=[O:32].[CH3:1][N:2]([CH2:3][c:4]1[cH:5][c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[n:12]1[CH3:13])[C:14](=[O:15])/[CH:16]=[CH:17]/[c:18]1[cH:19][cH:20][c:21]([NH2:22])[n:33][cH:34]1>C1CCOC1.O=C(O)O.[Na+]>[CH3:1][N:2]([CH2:3][c:4]1[cH:5][c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[n:12]1[CH3:13])[C:14](=[O:15])/[CH:16]=[CH:17]/[c:18]1[cH:19][cH:20][c:21]([N:22]2[C:23](=[O:24])[c:25]3[cH:26][cH:27][cH:28][cH:29][c:30]3[C:31]2=[O:32])[n:33][cH:34]1\"}",
"reactionStep": {
"id": "sa_c0e1fe2dfd669d3ed030171d",
"reactionHash": "5eff9571fa604e06a8833ab8553c374bd032ed2af090979b3c67df614dfee7f3"
},
"children": [
{
"id": "9588",
"routeId": "sa_7a7229e164de53373423803e",
"moleculeId": "sa_18ddba5ba049450524799e82",
"parentId": "9587",
"isLeaf": false,
"molecule": {
"id": "sa_18ddba5ba049450524799e82",
"inchikey": "AKFPMLBVLWZSQX-CSKARUKUSA-N",
"smiles": "CN(Cc1cc2ccccc2n1C)C(=O)/C=C/c1ccc(N)nc1"
},
"smiles": "CN(Cc1cc2ccccc2n1C)C(=O)/C=C/c1ccc(N)nc1",
"reactionStepId": "sa_333d059252e5a60309bef75d",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20090275572A1;0241;786120\",\"rsmi\":\"O[C:14](=[O:15])/[CH:16]=[CH:17]/[c:18]1[cH:19][cH:20][c:21]([NH2:22])[n:23][cH:24]1.[CH3:1][NH:2][CH2:3][c:4]1[cH:5][c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[n:12]1[CH3:13]>CCN(CC)CC.CN(C)C=O.ClCCCl.O.On1nnc2ccccc21>[CH3:1][N:2]([CH2:3][c:4]1[cH:5][c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[n:12]1[CH3:13])[C:14](=[O:15])/[CH:16]=[CH:17]/[c:18]1[cH:19][cH:20][c:21]([NH2:22])[n:23][cH:24]1\"},\"mapped_reaction_smiles\":\"O[C:14](=[O:15])/[CH:16]=[CH:17]/[c:18]1[cH:19][cH:20][c:21]([NH2:22])[n:23][cH:24]1.[CH3:1][NH:2][CH2:3][c:4]1[cH:5][c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[n:12]1[CH3:13]>CCN(CC)CC.CN(C)C=O.ClCCCl.O.On1nnc2ccccc21>[CH3:1][N:2]([CH2:3][c:4]1[cH:5][c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[n:12]1[CH3:13])[C:14](=[O:15])/[CH:16]=[CH:17]/[c:18]1[cH:19][cH:20][c:21]([NH2:22])[n:23][cH:24]1\"}",
"reactionStep": {
"id": "sa_333d059252e5a60309bef75d",
"reactionHash": "e686241dc5306d867c6bb7656814f918e37d842b6f9f794c2e6f7d96a5ea5ba2"
},
"children": [
{
"id": "9589",
"routeId": "sa_7a7229e164de53373423803e",
"moleculeId": "sa_da21b23ef43b385af75dfc90",
"parentId": "9588",
"isLeaf": false,
"molecule": {
"id": "sa_da21b23ef43b385af75dfc90",
"inchikey": "BMINWSYCLTUQSH-UHFFFAOYSA-N",
"smiles": "CNCc1cc2ccccc2n1C"
},
"smiles": "CNCc1cc2ccccc2n1C",
"reactionStepId": "sa_ff3dab987dc788171bf8f94d",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20090275572A1;0092;786043\",\"rsmi\":\"O=[C:3]([NH:2][CH3:1])[c:4]1[cH:5][c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[n:12]1[CH3:13]>C1CCOC1.[Al+3].[HH].[HH].[HH].[HH].[Li+]>[CH3:1][NH:2][CH2:3][c:4]1[cH:5][c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[n:12]1[CH3:13]\"},\"mapped_reaction_smiles\":\"O=[C:3]([NH:2][CH3:1])[c:4]1[cH:5][c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[n:12]1[CH3:13]>C1CCOC1.[Al+3].[HH].[HH].[HH].[HH].[Li+]>[CH3:1][NH:2][CH2:3][c:4]1[cH:5][c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[n:12]1[CH3:13]\"}",
"reactionStep": {
"id": "sa_ff3dab987dc788171bf8f94d",
"reactionHash": "05f8762efd29304d2a0cc420d71556594e60d760bd6be89220dad733537ac421"
},
"children": [
{
"id": "9590",
"routeId": "sa_7a7229e164de53373423803e",
"moleculeId": "sa_8dfa6b6fd7aa343804a3acc3",
"parentId": "9589",
"isLeaf": false,
"molecule": {
"id": "sa_8dfa6b6fd7aa343804a3acc3",
"inchikey": "MIEPSGVCFRDTDU-UHFFFAOYSA-N",
"smiles": "CNC(=O)c1cc2ccccc2n1C"
},
"smiles": "CNC(=O)c1cc2ccccc2n1C",
"reactionStepId": "sa_b5008b2fe7163e91df044c7f",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20090275572A1;0091;786042\",\"rsmi\":\"CCO[C:3](=[O:4])[c:5]1[cH:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[n:13]1[CH3:14].[CH3:1][NH2:2]>CO>[CH3:1][NH:2][C:3](=[O:4])[c:5]1[cH:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[n:13]1[CH3:14]\"},\"mapped_reaction_smiles\":\"CCO[C:3](=[O:4])[c:5]1[cH:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[n:13]1[CH3:14].[CH3:1][NH2:2]>CO>[CH3:1][NH:2][C:3](=[O:4])[c:5]1[cH:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[n:13]1[CH3:14]\"}",
"reactionStep": {
"id": "sa_b5008b2fe7163e91df044c7f",
"reactionHash": "6e9ead54e35e2dbeb7950ea205a45c4fca24fecf77d7537ef2cb6289da1e880c"
},
"children": [
{
"id": "9591",
"routeId": "sa_7a7229e164de53373423803e",
"moleculeId": "sa_e00cdbb7fb9d3ecf114a19d3",
"parentId": "9590",
"isLeaf": true,
"molecule": {
"id": "sa_e00cdbb7fb9d3ecf114a19d3",
"inchikey": "BAVYZALUXZFZLV-UHFFFAOYSA-N",
"smiles": "CN"
},
"smiles": "CN",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "9592",
"routeId": "sa_7a7229e164de53373423803e",
"moleculeId": "sa_2ead340295f56117cd1a0fd3",
"parentId": "9590",
"isLeaf": false,
"molecule": {
"id": "sa_2ead340295f56117cd1a0fd3",
"inchikey": "FRLLPWADCHCBBY-UHFFFAOYSA-N",
"smiles": "CCOC(=O)c1cc2ccccc2n1C"
},
"smiles": "CCOC(=O)c1cc2ccccc2n1C",
"reactionStepId": "sa_d4cc9b1b9ed8d8e49e1d1e01",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20090275572A1;0090;786041\",\"rsmi\":\"I[CH3:15].[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[nH:14]1>CN(C)C=O.[HH].[Na+]>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[n:14]1[CH3:15]\"},\"mapped_reaction_smiles\":\"I[CH3:15].[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[nH:14]1>CN(C)C=O.[HH].[Na+]>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[n:14]1[CH3:15]\"}",
"reactionStep": {
"id": "sa_d4cc9b1b9ed8d8e49e1d1e01",
"reactionHash": "4d90a75e163ff6143839825c3fdc8b072a79d156382c97e83e53343e5e97dfe6"
},
"children": [
{
"id": "9593",
"routeId": "sa_7a7229e164de53373423803e",
"moleculeId": "sa_82fdccf7d1cc329c9db73f21",
"parentId": "9592",
"isLeaf": true,
"molecule": {
"id": "sa_82fdccf7d1cc329c9db73f21",
"inchikey": "INQOMBQAUSQDDS-UHFFFAOYSA-N",
"smiles": "CI"
},
"smiles": "CI",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "9594",
"routeId": "sa_7a7229e164de53373423803e",
"moleculeId": "sa_7168d19360d8cc6a724fa7ae",
"parentId": "9592",
"isLeaf": true,
"molecule": {
"id": "sa_7168d19360d8cc6a724fa7ae",
"inchikey": "QQXQAEWRSVZPJM-UHFFFAOYSA-N",
"smiles": "CCOC(=O)c1cc2ccccc2[nH]1"
},
"smiles": "CCOC(=O)c1cc2ccccc2[nH]1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
]
},
{
"id": "9595",
"routeId": "sa_7a7229e164de53373423803e",
"moleculeId": "sa_11df66cea1ba8c7c92407eb5",
"parentId": "9588",
"isLeaf": false,
"molecule": {
"id": "sa_11df66cea1ba8c7c92407eb5",
"inchikey": "RKTFOZFRTWRSLT-DUXPYHPUSA-N",
"smiles": "Nc1ccc(/C=C/C(=O)O)cn1"
},
"smiles": "Nc1ccc(/C=C/C(=O)O)cn1",
"reactionStepId": "sa_105172c47faa5fc2aaeb08f9",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20090275572A1;0094;786045\",\"rsmi\":\"c1ccc(C[O:10][C:8](/[CH:7]=[CH:6]/[c:5]2[cH:4][cH:3][c:2]([NH2:1])[n:12][cH:11]2)=[O:9])cc1>CO.[Na+].O>[NH2:1][c:2]1[cH:3][cH:4][c:5](/[CH:6]=[CH:7]/[C:8](=[O:9])[OH:10])[cH:11][n:12]1\"},\"mapped_reaction_smiles\":\"c1ccc(C[O:10][C:8](/[CH:7]=[CH:6]/[c:5]2[cH:4][cH:3][c:2]([NH2:1])[n:12][cH:11]2)=[O:9])cc1>CO.[Na+].O>[NH2:1][c:2]1[cH:3][cH:4][c:5](/[CH:6]=[CH:7]/[C:8](=[O:9])[OH:10])[cH:11][n:12]1\"}",
"reactionStep": {
"id": "sa_105172c47faa5fc2aaeb08f9",
"reactionHash": "6e3c701a78aa4da70a2a82fc18dc164402c270dea172fac1436bdc00be4d5758"
},
"children": [
{
"id": "9596",
"routeId": "sa_7a7229e164de53373423803e",
"moleculeId": "sa_55b6aa432fc892c34192c74c",
"parentId": "9595",
"isLeaf": true,
"molecule": {
"id": "sa_55b6aa432fc892c34192c74c",
"inchikey": "RPGACVPVPGPLHQ-VQHVLOKHSA-N",
"smiles": "Nc1ccc(/C=C/C(=O)OCc2ccccc2)cn1"
},
"smiles": "Nc1ccc(/C=C/C(=O)OCc2ccccc2)cn1",
"reactionStepId": null,
"template": null,
"metadata": null,
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}
]
}
]
},
{
"id": "9597",
"routeId": "sa_7a7229e164de53373423803e",
"moleculeId": "sa_df231fc07b563e3b0046b16e",
"parentId": "9587",
"isLeaf": true,
"molecule": {
"id": "sa_df231fc07b563e3b0046b16e",
"inchikey": "LGRFSURHDFAFJT-UHFFFAOYSA-N",
"smiles": "O=C1OC(=O)c2ccccc21"
},
"smiles": "O=C1OC(=O)c2ccccc21",
"reactionStepId": null,
"template": null,
"metadata": null,
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"children": []
}
]
}
}