Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CCOC(=O)c1ncc(Nc2nccc(N3C[C@H]4CC[C@@H](C3)N4C(=O)OC(C)(C)C)n2)cc1C
InChiKey
QWHMLKAMDHDWBM-HDICACEKSA-N
Route Signature
2d6a14cc1b1e5bc74dd65f9a667dd02ce7287c1e5c2e20801e362f4a4942fbb1
Synthesis route with 3 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_8b117285de708a834e12125c",
"signature": "2d6a14cc1b1e5bc74dd65f9a667dd02ce7287c1e5c2e20801e362f4a4942fbb1",
"contentHash": "58ec4cc4533b16a956095b1b8349814d292bd05303f35ceb35b22bd64e1f2be3",
"length": 3,
"isConvergent": true
},
"target": {
"id": "sa_b33fca50b8e3ec6e788c83ff",
"benchmarkSetId": "7390a9c2522b1c81605e80a42a8de7c7ad9a5797d028633b54904bc78f091bb8",
"targetId": "n5-01194",
"moleculeId": "sa_53d527e7f114a0a15dbfb9b0",
"smiles": "CCOC(=O)c1ncc(Nc2nccc(N3C[C@H]4CC[C@@H](C3)N4C(=O)OC(C)(C)C)n2)cc1C",
"routeLength": 3,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_53d527e7f114a0a15dbfb9b0",
"inchikey": "QWHMLKAMDHDWBM-HDICACEKSA-N",
"smiles": "CCOC(=O)c1ncc(Nc2nccc(N3C[C@H]4CC[C@@H](C3)N4C(=O)OC(C)(C)C)n2)cc1C"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 2
},
"rootNode": {
"id": "1317",
"routeId": "sa_8b117285de708a834e12125c",
"moleculeId": "sa_53d527e7f114a0a15dbfb9b0",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_53d527e7f114a0a15dbfb9b0",
"inchikey": "QWHMLKAMDHDWBM-HDICACEKSA-N",
"smiles": "CCOC(=O)c1ncc(Nc2nccc(N3C[C@H]4CC[C@@H](C3)N4C(=O)OC(C)(C)C)n2)cc1C"
},
"smiles": "CCOC(=O)c1ncc(Nc2nccc(N3C[C@H]4CC[C@@H](C3)N4C(=O)OC(C)(C)C)n2)cc1C",
"reactionStepId": "sa_08857c40636ce12b2c046668",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160052930A1;0601;1843548\",\"rsmi\":\"Cl[c:12]1[n:13][cH:14][cH:15][c:16]([N:17]2[CH2:18][C@H:19]3[CH2:20][CH2:21][C@@H:22]([CH2:23]2)[N:24]3[C:25](=[O:26])[O:27][C:28]([CH3:29])([CH3:30])[CH3:31])[n:32]1.[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7]([CH3:8])[cH:9][c:10]([NH2:11])[cH:33][n:34]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7]([CH3:8])[cH:9][c:10]([NH:11][c:12]2[n:13][cH:14][cH:15][c:16]([N:17]3[CH2:18][C@@H:19]4[CH2:20][CH2:21][C@H:22]([CH2:23]3)[N:24]4[C:25](=[O:26])[O:27][C:28]([CH3:29])([CH3:30])[CH3:31])[n:32]2)[cH:33][n:34]1\"},\"mapped_reaction_smiles\":\"Cl[c:12]1[n:13][cH:14][cH:15][c:16]([N:17]2[CH2:18][C@H:19]3[CH2:20][CH2:21][C@@H:22]([CH2:23]2)[N:24]3[C:25](=[O:26])[O:27][C:28]([CH3:29])([CH3:30])[CH3:31])[n:32]1.[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7]([CH3:8])[cH:9][c:10]([NH2:11])[cH:33][n:34]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7]([CH3:8])[cH:9][c:10]([NH:11][c:12]2[n:13][cH:14][cH:15][c:16]([N:17]3[CH2:18][C@@H:19]4[CH2:20][CH2:21][C@H:22]([CH2:23]3)[N:24]4[C:25](=[O:26])[O:27][C:28]([CH3:29])([CH3:30])[CH3:31])[n:32]2)[cH:33][n:34]1\"}",
"reactionStep": {
"id": "sa_08857c40636ce12b2c046668",
"reactionHash": "3db6e6b893e6d7ef62750a187bef749434c6d1930fef80b715009063aaa61061"
},
"children": [
{
"id": "1318",
"routeId": "sa_8b117285de708a834e12125c",
"moleculeId": "sa_20d7f29cf5918533197804a7",
"parentId": "1317",
"isLeaf": false,
"molecule": {
"id": "sa_20d7f29cf5918533197804a7",
"inchikey": "LILIXCUOLXPXGC-UHFFFAOYSA-N",
"smiles": "CCOC(=O)c1ncc(N)cc1C"
},
"smiles": "CCOC(=O)c1ncc(N)cc1C",
"reactionStepId": "sa_b7ced0d3016df712d2d20bf8",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160052930A1;0612;1843552\",\"rsmi\":\"O=[N+:10]([O-])[c:9]1[cH:8][n:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:12]([CH3:13])[cH:11]1>CCO.[Pd]>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[n:7][cH:8][c:9]([NH2:10])[cH:11][c:12]1[CH3:13]\"},\"mapped_reaction_smiles\":\"O=[N+:10]([O-])[c:9]1[cH:8][n:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:12]([CH3:13])[cH:11]1>CCO.[Pd]>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[n:7][cH:8][c:9]([NH2:10])[cH:11][c:12]1[CH3:13]\"}",
"reactionStep": {
"id": "sa_b7ced0d3016df712d2d20bf8",
"reactionHash": "1b6ff1d1e3c2cf534003cd5d1d5d68f9805a867fb35041edf2c47c7b03ec262d"
},
"children": [
{
"id": "1319",
"routeId": "sa_8b117285de708a834e12125c",
"moleculeId": "sa_4ef9c55da75492973d504ffc",
"parentId": "1318",
"isLeaf": false,
"molecule": {
"id": "sa_4ef9c55da75492973d504ffc",
"inchikey": "NFNYNFQPOYCXBK-UHFFFAOYSA-N",
"smiles": "CCOC(=O)c1ncc([N+](=O)[O-])cc1C"
},
"smiles": "CCOC(=O)c1ncc([N+](=O)[O-])cc1C",
"reactionStepId": "sa_4f68e3f1417c253ccb1e0487",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160052930A1;0624;1843557\",\"rsmi\":\"N#[C:4][c:6]1[n:7][cH:8][c:9]([N+:10](=[O:11])[O-:12])[cH:13][c:14]1[CH3:15].O=S(O)(O)=[O:5].[CH3:1][CH2:2][OH:3]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[n:7][cH:8][c:9]([N+:10](=[O:11])[O-:12])[cH:13][c:14]1[CH3:15]\"},\"mapped_reaction_smiles\":\"N#[C:4][c:6]1[n:7][cH:8][c:9]([N+:10](=[O:11])[O-:12])[cH:13][c:14]1[CH3:15].O=S(O)(O)=[O:5].[CH3:1][CH2:2][OH:3]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[n:7][cH:8][c:9]([N+:10](=[O:11])[O-:12])[cH:13][c:14]1[CH3:15]\"}",
"reactionStep": {
"id": "sa_4f68e3f1417c253ccb1e0487",
"reactionHash": "5a30a1db4be3522d896179ad38976dbe938287ea92d23ae561fdbe611a9adc2d"
},
"children": [
{
"id": "1320",
"routeId": "sa_8b117285de708a834e12125c",
"moleculeId": "sa_2e85fbc9615fcd55ba592779",
"parentId": "1319",
"isLeaf": true,
"molecule": {
"id": "sa_2e85fbc9615fcd55ba592779",
"inchikey": "KMSQJNWARXZFII-UHFFFAOYSA-N",
"smiles": "Cc1cc([N+](=O)[O-])cnc1C#N"
},
"smiles": "Cc1cc([N+](=O)[O-])cnc1C#N",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "1321",
"routeId": "sa_8b117285de708a834e12125c",
"moleculeId": "sa_afaca116b303dc7d01346819",
"parentId": "1319",
"isLeaf": true,
"molecule": {
"id": "sa_afaca116b303dc7d01346819",
"inchikey": "LFQSCWFLJHTTHZ-UHFFFAOYSA-N",
"smiles": "CCO"
},
"smiles": "CCO",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "1322",
"routeId": "sa_8b117285de708a834e12125c",
"moleculeId": "sa_a538ca410f1833f7a9788be8",
"parentId": "1319",
"isLeaf": true,
"molecule": {
"id": "sa_a538ca410f1833f7a9788be8",
"inchikey": "QAOWNCQODCNURD-UHFFFAOYSA-N",
"smiles": "O=S(=O)(O)O"
},
"smiles": "O=S(=O)(O)O",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
},
{
"id": "1323",
"routeId": "sa_8b117285de708a834e12125c",
"moleculeId": "sa_04d7528b87661ba86340e7b6",
"parentId": "1317",
"isLeaf": false,
"molecule": {
"id": "sa_04d7528b87661ba86340e7b6",
"inchikey": "OECIBZZKIXVOKZ-PHIMTYICSA-N",
"smiles": "CC(C)(C)OC(=O)N1[C@@H]2CC[C@H]1CN(c1ccnc(Cl)n1)C2"
},
"smiles": "CC(C)(C)OC(=O)N1[C@@H]2CC[C@H]1CN(c1ccnc(Cl)n1)C2",
"reactionStepId": "sa_134b8ad95311699117bba252",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160052930A1;0602;1843549\",\"rsmi\":\"Cl[c:15]1[n:16][c:17]([Cl:18])[n:19][cH:20][cH:21]1.[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[C@H:9]2[CH2:10][CH2:11][C@@H:12]1[CH2:13][NH:14][CH2:22]2>CO>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[C@H:9]2[CH2:10][CH2:11][C@@H:12]1[CH2:13][N:14]([c:15]1[n:16][c:17]([Cl:18])[n:19][cH:20][cH:21]1)[CH2:22]2\"},\"mapped_reaction_smiles\":\"Cl[c:15]1[n:16][c:17]([Cl:18])[n:19][cH:20][cH:21]1.[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[C@H:9]2[CH2:10][CH2:11][C@@H:12]1[CH2:13][NH:14][CH2:22]2>CO>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[C@H:9]2[CH2:10][CH2:11][C@@H:12]1[CH2:13][N:14]([c:15]1[n:16][c:17]([Cl:18])[n:19][cH:20][cH:21]1)[CH2:22]2\"}",
"reactionStep": {
"id": "sa_134b8ad95311699117bba252",
"reactionHash": "d4e966070a52afe40aa4faef06a8415b1731b5fe546731214654ccb6637447db"
},
"children": [
{
"id": "1324",
"routeId": "sa_8b117285de708a834e12125c",
"moleculeId": "sa_aeda22e5315bd455d285f564",
"parentId": "1323",
"isLeaf": true,
"molecule": {
"id": "sa_aeda22e5315bd455d285f564",
"inchikey": "BTTNYQZNBZNDOR-UHFFFAOYSA-N",
"smiles": "Clc1ccnc(Cl)n1"
},
"smiles": "Clc1ccnc(Cl)n1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "1325",
"routeId": "sa_8b117285de708a834e12125c",
"moleculeId": "sa_da78da5b285096c22487617a",
"parentId": "1323",
"isLeaf": false,
"molecule": {
"id": "sa_da78da5b285096c22487617a",
"inchikey": "HNINFCBLGHCFOJ-DTORHVGOSA-N",
"smiles": "CC(C)(C)OC(=O)N1[C@@H]2CC[C@H]1CNC2"
},
"smiles": "CC(C)(C)OC(=O)N1[C@@H]2CC[C@H]1CNC2",
"reactionStepId": "sa_f5a2f03bd8c5a14d0e9e4000",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160052930A1;0605;1843550\",\"rsmi\":\"c1ccc(C[N:14]2[CH2:13][C@@H:12]3[N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[C@@H:9]([CH2:10][CH2:11]3)[CH2:15]2)cc1>CO.[Pd]>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[C@H:9]2[CH2:10][CH2:11][C@@H:12]1[CH2:13][NH:14][CH2:15]2\"},\"mapped_reaction_smiles\":\"c1ccc(C[N:14]2[CH2:13][C@@H:12]3[N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[C@@H:9]([CH2:10][CH2:11]3)[CH2:15]2)cc1>CO.[Pd]>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[C@H:9]2[CH2:10][CH2:11][C@@H:12]1[CH2:13][NH:14][CH2:15]2\"}",
"reactionStep": {
"id": "sa_f5a2f03bd8c5a14d0e9e4000",
"reactionHash": "ea1089c91ef3cfaf7fe5a1d116f480238f73bd64bdd02cf5e9c42e756d7ab1fc"
},
"children": [
{
"id": "1326",
"routeId": "sa_8b117285de708a834e12125c",
"moleculeId": "sa_6a5c444b0fb5ab9a0ef40a04",
"parentId": "1325",
"isLeaf": true,
"molecule": {
"id": "sa_6a5c444b0fb5ab9a0ef40a04",
"inchikey": "IOPMFGUNMBWHIS-IYBDPMFKSA-N",
"smiles": "CC(C)(C)OC(=O)N1[C@@H]2CC[C@H]1CN(Cc1ccccc1)C2"
},
"smiles": "CC(C)(C)OC(=O)N1[C@@H]2CC[C@H]1CN(Cc1ccccc1)C2",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
]
}
}