Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CCN1c2ncc(CCOc3ccc(-c4cc(C(=O)O)on4)cc3C)cc2C(=O)N(C)c2cccnc21
InChiKey
WVITWHHNKGAMLB-UHFFFAOYSA-N
Route Signature
1c30aaa31ffeefe7db6ebbe5e0e5eff88aca5f5fc475e86d5f7d6386ca04e9d1
Synthesis route with 6 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_d65cc208e7b8eafd3fde9768",
"signature": "1c30aaa31ffeefe7db6ebbe5e0e5eff88aca5f5fc475e86d5f7d6386ca04e9d1",
"contentHash": "30255064ddb70637bf9861e31b9f63126d6ed157c2f761d083f5b5c9f823794c",
"length": 6,
"isConvergent": false
},
"target": {
"id": "sa_30de176db0d4f1368fad9f20",
"benchmarkSetId": "61e696668b63e77d7c2a29c0821768e1c383de8313852d6e995224859494442e",
"targetId": "n5-00666",
"moleculeId": "sa_cae8fc5bf71204761ec13561",
"smiles": "CCN1c2ncc(CCOc3ccc(-c4cc(C(=O)O)on4)cc3C)cc2C(=O)N(C)c2cccnc21",
"routeLength": 6,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_cae8fc5bf71204761ec13561",
"inchikey": "WVITWHHNKGAMLB-UHFFFAOYSA-N",
"smiles": "CCN1c2ncc(CCOc3ccc(-c4cc(C(=O)O)on4)cc3C)cc2C(=O)N(C)c2cccnc21"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "13656",
"routeId": "sa_d65cc208e7b8eafd3fde9768",
"moleculeId": "sa_cae8fc5bf71204761ec13561",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_cae8fc5bf71204761ec13561",
"inchikey": "WVITWHHNKGAMLB-UHFFFAOYSA-N",
"smiles": "CCN1c2ncc(CCOc3ccc(-c4cc(C(=O)O)on4)cc3C)cc2C(=O)N(C)c2cccnc21"
},
"smiles": "CCN1c2ncc(CCOc3ccc(-c4cc(C(=O)O)on4)cc3C)cc2C(=O)N(C)c2cccnc21",
"reactionStepId": "sa_0841370ace0d34099f11e204",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20040006071A1;0186;122611\",\"rsmi\":\"CC[O:22][C:20]([c:19]1[o:18][n:17][c:16](-[c:15]2[cH:14][c:12]([CH3:13])[c:11]([O:10][CH2:9][CH2:8][c:7]3[cH:6][c:5]4[c:4]([n:27][cH:26]3)[N:3]([CH2:2][CH3:1])[c:33]3[c:32]([cH:37][cH:36][cH:35][n:34]3)[N:30]([CH3:31])[C:28]4=[O:29])[cH:25][cH:24]2)[cH:23]1)=[O:21]>C1CCOC1.CO.[Na+].O>[CH3:1][CH2:2][N:3]1[c:4]2[c:5]([cH:6][c:7]([CH2:8][CH2:9][O:10][c:11]3[c:12]([CH3:13])[cH:14][c:15](-[c:16]4[n:17][o:18][c:19]([C:20](=[O:21])[OH:22])[cH:23]4)[cH:24][cH:25]3)[cH:26][n:27]2)[C:28](=[O:29])[N:30]([CH3:31])[c:32]2[c:33]1[n:34][cH:35][cH:36][cH:37]2\"},\"mapped_reaction_smiles\":\"CC[O:22][C:20]([c:19]1[o:18][n:17][c:16](-[c:15]2[cH:14][c:12]([CH3:13])[c:11]([O:10][CH2:9][CH2:8][c:7]3[cH:6][c:5]4[c:4]([n:27][cH:26]3)[N:3]([CH2:2][CH3:1])[c:33]3[c:32]([cH:37][cH:36][cH:35][n:34]3)[N:30]([CH3:31])[C:28]4=[O:29])[cH:25][cH:24]2)[cH:23]1)=[O:21]>C1CCOC1.CO.[Na+].O>[CH3:1][CH2:2][N:3]1[c:4]2[c:5]([cH:6][c:7]([CH2:8][CH2:9][O:10][c:11]3[c:12]([CH3:13])[cH:14][c:15](-[c:16]4[n:17][o:18][c:19]([C:20](=[O:21])[OH:22])[cH:23]4)[cH:24][cH:25]3)[cH:26][n:27]2)[C:28](=[O:29])[N:30]([CH3:31])[c:32]2[c:33]1[n:34][cH:35][cH:36][cH:37]2\"}",
"reactionStep": {
"id": "sa_0841370ace0d34099f11e204",
"reactionHash": "9b7765b3627ad5f3bf12c84268e7589224598833661726145e5af7004dd9582c"
},
"children": [
{
"id": "13657",
"routeId": "sa_d65cc208e7b8eafd3fde9768",
"moleculeId": "sa_8ad30a5ab0067badfd8c1fc6",
"parentId": "13656",
"isLeaf": false,
"molecule": {
"id": "sa_8ad30a5ab0067badfd8c1fc6",
"inchikey": "GQPGCYZJKOHJDT-UHFFFAOYSA-N",
"smiles": "CCOC(=O)c1cc(-c2ccc(OCCc3cnc4c(c3)C(=O)N(C)c3cccnc3N4CC)c(C)c2)no1"
},
"smiles": "CCOC(=O)c1cc(-c2ccc(OCCc3cnc4c(c3)C(=O)N(C)c3cccnc3N4CC)c(C)c2)no1",
"reactionStepId": "sa_0cba36cd7fb2d127e289e1fd",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20040006071A1;0184;122610\",\"rsmi\":\"O[CH2:15][CH2:16][c:17]1[cH:18][c:19]2[c:20]([n:21][cH:22]1)[N:23]([CH2:24][CH3:25])[c:26]1[c:27]([cH:28][cH:29][cH:30][n:31]1)[N:32]([CH3:33])[C:34]2=[O:35].[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8](-[c:9]2[cH:10][c:11]([CH3:12])[c:13]([OH:14])[cH:36][cH:37]2)[n:38][o:39]1>C1CCOC1.CCOC(=O)/N=N/C(=O)OCC.c1ccc(P(c2ccccc2)c2ccccc2)cc1>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8](-[c:9]2[cH:10][c:11]([CH3:12])[c:13]([O:14][CH2:15][CH2:16][c:17]3[cH:18][c:19]4[c:20]([n:21][cH:22]3)[N:23]([CH2:24][CH3:25])[c:26]3[c:27]([cH:28][cH:29][cH:30][n:31]3)[N:32]([CH3:33])[C:34]4=[O:35])[cH:36][cH:37]2)[n:38][o:39]1\"},\"mapped_reaction_smiles\":\"O[CH2:15][CH2:16][c:17]1[cH:18][c:19]2[c:20]([n:21][cH:22]1)[N:23]([CH2:24][CH3:25])[c:26]1[c:27]([cH:28][cH:29][cH:30][n:31]1)[N:32]([CH3:33])[C:34]2=[O:35].[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8](-[c:9]2[cH:10][c:11]([CH3:12])[c:13]([OH:14])[cH:36][cH:37]2)[n:38][o:39]1>C1CCOC1.CCOC(=O)/N=N/C(=O)OCC.c1ccc(P(c2ccccc2)c2ccccc2)cc1>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8](-[c:9]2[cH:10][c:11]([CH3:12])[c:13]([O:14][CH2:15][CH2:16][c:17]3[cH:18][c:19]4[c:20]([n:21][cH:22]3)[N:23]([CH2:24][CH3:25])[c:26]3[c:27]([cH:28][cH:29][cH:30][n:31]3)[N:32]([CH3:33])[C:34]4=[O:35])[cH:36][cH:37]2)[n:38][o:39]1\"}",
"reactionStep": {
"id": "sa_0cba36cd7fb2d127e289e1fd",
"reactionHash": "abaeb983e80d5c9f40e5c285f7a780f51b3dc5f76509fbc4cd8e61ef17ca5645"
},
"children": [
{
"id": "13658",
"routeId": "sa_d65cc208e7b8eafd3fde9768",
"moleculeId": "sa_cad5e3f4d3630075adbfd20c",
"parentId": "13657",
"isLeaf": true,
"molecule": {
"id": "sa_cad5e3f4d3630075adbfd20c",
"inchikey": "LSDLBGOYTYAGQC-UHFFFAOYSA-N",
"smiles": "CCN1c2ncc(CCO)cc2C(=O)N(C)c2cccnc21"
},
"smiles": "CCN1c2ncc(CCO)cc2C(=O)N(C)c2cccnc21",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "13659",
"routeId": "sa_d65cc208e7b8eafd3fde9768",
"moleculeId": "sa_77a09004d82f3491787cf933",
"parentId": "13657",
"isLeaf": false,
"molecule": {
"id": "sa_77a09004d82f3491787cf933",
"inchikey": "MZTFQHKIUKWTHJ-UHFFFAOYSA-N",
"smiles": "CCOC(=O)c1cc(-c2ccc(O)c(C)c2)no1"
},
"smiles": "CCOC(=O)c1cc(-c2ccc(O)c(C)c2)no1",
"reactionStepId": "sa_80b365874b03dd8ae253609a",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20040006071A1;0182;122609\",\"rsmi\":\"COC[O:14][c:13]1[c:11]([CH3:12])[cH:10][c:9](-[c:8]2[cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[o:18][n:17]2)[cH:16][cH:15]1>C1CCOC1.CCOC(C)=O.Cl>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8](-[c:9]2[cH:10][c:11]([CH3:12])[c:13]([OH:14])[cH:15][cH:16]2)[n:17][o:18]1\"},\"mapped_reaction_smiles\":\"COC[O:14][c:13]1[c:11]([CH3:12])[cH:10][c:9](-[c:8]2[cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[o:18][n:17]2)[cH:16][cH:15]1>C1CCOC1.CCOC(C)=O.Cl>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8](-[c:9]2[cH:10][c:11]([CH3:12])[c:13]([OH:14])[cH:15][cH:16]2)[n:17][o:18]1\"}",
"reactionStep": {
"id": "sa_80b365874b03dd8ae253609a",
"reactionHash": "c48873410ce3e208a35acd5b8e9db8399600e96ff90c26cd49e1f667b3270c0b"
},
"children": [
{
"id": "13660",
"routeId": "sa_d65cc208e7b8eafd3fde9768",
"moleculeId": "sa_fef907696dcdda3dac9f050c",
"parentId": "13659",
"isLeaf": false,
"molecule": {
"id": "sa_fef907696dcdda3dac9f050c",
"inchikey": "LMTFMERJFTUJPE-UHFFFAOYSA-N",
"smiles": "CCOC(=O)c1cc(-c2ccc(OCOC)c(C)c2)no1"
},
"smiles": "CCOC(=O)c1cc(-c2ccc(OCOC)c(C)c2)no1",
"reactionStepId": "sa_c93015be45b3c4d7a13c75b3",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20040006071A1;0180;122608\",\"rsmi\":\"[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]#[CH:7].[CH:8]([c:9]1[cH:10][c:11]([CH3:12])[c:13]([O:14][CH2:15][O:16][CH3:17])[cH:18][cH:19]1)=[N:20][OH:21]>C1CCOC1.CCOC(C)=O.O.[Na+].OCl>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8](-[c:9]2[cH:10][c:11]([CH3:12])[c:13]([O:14][CH2:15][O:16][CH3:17])[cH:18][cH:19]2)[n:20][o:21]1\"},\"mapped_reaction_smiles\":\"[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]#[CH:7].[CH:8]([c:9]1[cH:10][c:11]([CH3:12])[c:13]([O:14][CH2:15][O:16][CH3:17])[cH:18][cH:19]1)=[N:20][OH:21]>C1CCOC1.CCOC(C)=O.O.[Na+].OCl>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8](-[c:9]2[cH:10][c:11]([CH3:12])[c:13]([O:14][CH2:15][O:16][CH3:17])[cH:18][cH:19]2)[n:20][o:21]1\"}",
"reactionStep": {
"id": "sa_c93015be45b3c4d7a13c75b3",
"reactionHash": "e5c1b425cca05e13ae269b54eb2ae30aa13677c013ee5911d5da06e5c515586a"
},
"children": [
{
"id": "13661",
"routeId": "sa_d65cc208e7b8eafd3fde9768",
"moleculeId": "sa_a7f13113b4be59456f104a9b",
"parentId": "13660",
"isLeaf": true,
"molecule": {
"id": "sa_a7f13113b4be59456f104a9b",
"inchikey": "FMVJYQGSRWVMQV-UHFFFAOYSA-N",
"smiles": "C#CC(=O)OCC"
},
"smiles": "C#CC(=O)OCC",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "13662",
"routeId": "sa_d65cc208e7b8eafd3fde9768",
"moleculeId": "sa_d385cfddd578e8c6a6b59199",
"parentId": "13660",
"isLeaf": false,
"molecule": {
"id": "sa_d385cfddd578e8c6a6b59199",
"inchikey": "QTPUQIPDECAPGQ-UHFFFAOYSA-N",
"smiles": "COCOc1ccc(C=NO)cc1C"
},
"smiles": "COCOc1ccc(C=NO)cc1C",
"reactionStepId": "sa_2ceba5e41c8bc76aa62ac572",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20040006071A1;0178;122607\",\"rsmi\":\"O=[CH:10][c:9]1[cH:8][c:6]([CH3:7])[c:5]([O:4][CH2:3][O:2][CH3:1])[cH:14][cH:13]1.[NH2:11][OH:12]>C1COCCO1.CCN(CC)CC.CCOC(C)=O.Cl>[CH3:1][O:2][CH2:3][O:4][c:5]1[c:6]([CH3:7])[cH:8][c:9]([CH:10]=[N:11][OH:12])[cH:13][cH:14]1\"},\"mapped_reaction_smiles\":\"O=[CH:10][c:9]1[cH:8][c:6]([CH3:7])[c:5]([O:4][CH2:3][O:2][CH3:1])[cH:14][cH:13]1.[NH2:11][OH:12]>C1COCCO1.CCN(CC)CC.CCOC(C)=O.Cl>[CH3:1][O:2][CH2:3][O:4][c:5]1[c:6]([CH3:7])[cH:8][c:9]([CH:10]=[N:11][OH:12])[cH:13][cH:14]1\"}",
"reactionStep": {
"id": "sa_2ceba5e41c8bc76aa62ac572",
"reactionHash": "8513c0fbfc3c57819c67b49a745d94f5cca5ccb8f268832a7ee0b21c09f36f4a"
},
"children": [
{
"id": "13663",
"routeId": "sa_d65cc208e7b8eafd3fde9768",
"moleculeId": "sa_04a18e3f07bde82ca29399ee",
"parentId": "13662",
"isLeaf": true,
"molecule": {
"id": "sa_04a18e3f07bde82ca29399ee",
"inchikey": "AVXURJPOCDRRFD-UHFFFAOYSA-N",
"smiles": "NO"
},
"smiles": "NO",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "13664",
"routeId": "sa_d65cc208e7b8eafd3fde9768",
"moleculeId": "sa_1fd92606122cddb32058f9ee",
"parentId": "13662",
"isLeaf": false,
"molecule": {
"id": "sa_1fd92606122cddb32058f9ee",
"inchikey": "YISNRQDIZMPVJB-UHFFFAOYSA-N",
"smiles": "COCOc1ccc(C=O)cc1C"
},
"smiles": "COCOc1ccc(C=O)cc1C",
"reactionStepId": "sa_8ed8f1ca4be6459871ac265c",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20040006071A1;0176;122606\",\"rsmi\":\"Cl[CH2:3][O:2][CH3:1].[OH:4][c:5]1[c:6]([CH3:7])[cH:8][c:9]([CH:10]=[O:11])[cH:12][cH:13]1>CCN(CC)CC.CCOC(C)=O.ClCCl>[CH3:1][O:2][CH2:3][O:4][c:5]1[c:6]([CH3:7])[cH:8][c:9]([CH:10]=[O:11])[cH:12][cH:13]1\"},\"mapped_reaction_smiles\":\"Cl[CH2:3][O:2][CH3:1].[OH:4][c:5]1[c:6]([CH3:7])[cH:8][c:9]([CH:10]=[O:11])[cH:12][cH:13]1>CCN(CC)CC.CCOC(C)=O.ClCCl>[CH3:1][O:2][CH2:3][O:4][c:5]1[c:6]([CH3:7])[cH:8][c:9]([CH:10]=[O:11])[cH:12][cH:13]1\"}",
"reactionStep": {
"id": "sa_8ed8f1ca4be6459871ac265c",
"reactionHash": "6affced1ec21829ee41e4ae034f48543e01608fb02dbadd79807ac8ea1c6de9d"
},
"children": [
{
"id": "13665",
"routeId": "sa_d65cc208e7b8eafd3fde9768",
"moleculeId": "sa_54d48885d9bdcc0f731e6f6a",
"parentId": "13664",
"isLeaf": true,
"molecule": {
"id": "sa_54d48885d9bdcc0f731e6f6a",
"inchikey": "BAKYASSDAXQKKY-UHFFFAOYSA-N",
"smiles": "Cc1cc(C=O)ccc1O"
},
"smiles": "Cc1cc(C=O)ccc1O",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "13666",
"routeId": "sa_d65cc208e7b8eafd3fde9768",
"moleculeId": "sa_3b491e3532b8289adf4ebe71",
"parentId": "13664",
"isLeaf": true,
"molecule": {
"id": "sa_3b491e3532b8289adf4ebe71",
"inchikey": "XJUZRXYOEPSWMB-UHFFFAOYSA-N",
"smiles": "COCCl"
},
"smiles": "COCCl",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
]
}
]
}
]
}
]
}
}