Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CN1CCNC(CCOc2ccccc2)C1
InChiKey
YPWPJZUEILMWQV-UHFFFAOYSA-N
Route Signature
66bf27301f80aecb3e695226b7e363dfb90513e70ee55e985cc9de768254bf36
Synthesis route with 6 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_3f2f2879abc37a72be8708d4",
"signature": "66bf27301f80aecb3e695226b7e363dfb90513e70ee55e985cc9de768254bf36",
"contentHash": "672a0aa0d15f10cb35e0bb1bb8d4e0a5ee43fa1813333b37dcc3fcd435bec5dd",
"length": 6,
"isConvergent": false
},
"target": {
"id": "sa_17dc671f1650bf2fe71d9e44",
"benchmarkSetId": "61e696668b63e77d7c2a29c0821768e1c383de8313852d6e995224859494442e",
"targetId": "n5-00127",
"moleculeId": "sa_c87561efaef51b1e9c913709",
"smiles": "CN1CCNC(CCOc2ccccc2)C1",
"routeLength": 6,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_c87561efaef51b1e9c913709",
"inchikey": "YPWPJZUEILMWQV-UHFFFAOYSA-N",
"smiles": "CN1CCNC(CCOc2ccccc2)C1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "12479",
"routeId": "sa_3f2f2879abc37a72be8708d4",
"moleculeId": "sa_c87561efaef51b1e9c913709",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_c87561efaef51b1e9c913709",
"inchikey": "YPWPJZUEILMWQV-UHFFFAOYSA-N",
"smiles": "CN1CCNC(CCOc2ccccc2)C1"
},
"smiles": "CN1CCNC(CCOc2ccccc2)C1",
"reactionStepId": "sa_33d94beddc24b85697d90b48",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20070167457A1;0130;475251\",\"rsmi\":\"CO[C:1](=O)[N:2]1[CH2:3][CH2:4][NH:5][CH:6]([CH2:7][CH2:8][O:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[CH2:16]1>C1CCOC1.O.O=S(=O)(O)O.[Al+3].[HH].[HH].[HH].[HH].[Li+].[Na+].[Na+].[Na+].O>[CH3:1][N:2]1[CH2:3][CH2:4][NH:5][CH:6]([CH2:7][CH2:8][O:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[CH2:16]1\"},\"mapped_reaction_smiles\":\"CO[C:1](=O)[N:2]1[CH2:3][CH2:4][NH:5][CH:6]([CH2:7][CH2:8][O:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[CH2:16]1>C1CCOC1.O.O=S(=O)(O)O.[Al+3].[HH].[HH].[HH].[HH].[Li+].[Na+].[Na+].[Na+].O>[CH3:1][N:2]1[CH2:3][CH2:4][NH:5][CH:6]([CH2:7][CH2:8][O:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[CH2:16]1\"}",
"reactionStep": {
"id": "sa_33d94beddc24b85697d90b48",
"reactionHash": "b293428124270e2be3ebb4e3419d423960ce3d1a1dbabf926e7d462fd15f97e0"
},
"children": [
{
"id": "12480",
"routeId": "sa_3f2f2879abc37a72be8708d4",
"moleculeId": "sa_726e8273ff1a4b2b3f177bfa",
"parentId": "12479",
"isLeaf": false,
"molecule": {
"id": "sa_726e8273ff1a4b2b3f177bfa",
"inchikey": "XVABPWSEMLFBSL-UHFFFAOYSA-N",
"smiles": "COC(=O)N1CCNC(CCOc2ccccc2)C1"
},
"smiles": "COC(=O)N1CCNC(CCOc2ccccc2)C1",
"reactionStepId": "sa_deabd099d64033faedf98dcc",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20070167457A1;0129;475250\",\"rsmi\":\"CC(C)(C)OC(=O)[N:8]1[CH2:7][CH2:6][N:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:19][CH:9]1[CH2:10][CH2:11][O:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1>ClCCl.O=C(O)C(F)(F)F>[CH3:1][O:2][C:3](=[O:4])[N:5]1[CH2:6][CH2:7][NH:8][CH:9]([CH2:10][CH2:11][O:12][c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[CH2:19]1\"},\"mapped_reaction_smiles\":\"CC(C)(C)OC(=O)[N:8]1[CH2:7][CH2:6][N:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:19][CH:9]1[CH2:10][CH2:11][O:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1>ClCCl.O=C(O)C(F)(F)F>[CH3:1][O:2][C:3](=[O:4])[N:5]1[CH2:6][CH2:7][NH:8][CH:9]([CH2:10][CH2:11][O:12][c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[CH2:19]1\"}",
"reactionStep": {
"id": "sa_deabd099d64033faedf98dcc",
"reactionHash": "18e3292c8e8718a4c8c8cccc11071ac5634a1e9f9ca9d4c94c0680128ee14193"
},
"children": [
{
"id": "12481",
"routeId": "sa_3f2f2879abc37a72be8708d4",
"moleculeId": "sa_bdbaccc640f43bdff849ee9b",
"parentId": "12480",
"isLeaf": false,
"molecule": {
"id": "sa_bdbaccc640f43bdff849ee9b",
"inchikey": "HVNHXNFAKWQMPH-UHFFFAOYSA-N",
"smiles": "COC(=O)N1CCN(C(=O)OC(C)(C)C)C(CCOc2ccccc2)C1"
},
"smiles": "COC(=O)N1CCN(C(=O)OC(C)(C)C)C(CCOc2ccccc2)C1",
"reactionStepId": "sa_737b8c66eb52ec1e585c5cb1",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20070167457A1;0128;475249\",\"rsmi\":\"O[c:20]1[cH:21][cH:22][cH:23][cH:24][cH:25]1.[CH3:1][O:2][C:3](=[O:4])[N:5]1[CH2:6][CH2:7][N:8]([C:9](=[O:10])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15])[CH:16]([CH2:17][CH2:18][OH:19])[CH2:26]1>CCOC(=O)N=NC(=O)OCC.ClCCl.c1ccc(P(c2ccccc2)c2ccccc2)cc1>[CH3:1][O:2][C:3](=[O:4])[N:5]1[CH2:6][CH2:7][N:8]([C:9](=[O:10])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15])[CH:16]([CH2:17][CH2:18][O:19][c:20]2[cH:21][cH:22][cH:23][cH:24][cH:25]2)[CH2:26]1\"},\"mapped_reaction_smiles\":\"O[c:20]1[cH:21][cH:22][cH:23][cH:24][cH:25]1.[CH3:1][O:2][C:3](=[O:4])[N:5]1[CH2:6][CH2:7][N:8]([C:9](=[O:10])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15])[CH:16]([CH2:17][CH2:18][OH:19])[CH2:26]1>CCOC(=O)N=NC(=O)OCC.ClCCl.c1ccc(P(c2ccccc2)c2ccccc2)cc1>[CH3:1][O:2][C:3](=[O:4])[N:5]1[CH2:6][CH2:7][N:8]([C:9](=[O:10])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15])[CH:16]([CH2:17][CH2:18][O:19][c:20]2[cH:21][cH:22][cH:23][cH:24][cH:25]2)[CH2:26]1\"}",
"reactionStep": {
"id": "sa_737b8c66eb52ec1e585c5cb1",
"reactionHash": "e61fb14f74c7eb30fe3adb1adde2582c877f12d1e8b192a324ebd586ec3637bc"
},
"children": [
{
"id": "12482",
"routeId": "sa_3f2f2879abc37a72be8708d4",
"moleculeId": "sa_508aac1710199fd4ff30a7fe",
"parentId": "12481",
"isLeaf": false,
"molecule": {
"id": "sa_508aac1710199fd4ff30a7fe",
"inchikey": "DIBLMNKAVCVWEO-UHFFFAOYSA-N",
"smiles": "COC(=O)N1CCN(C(=O)OC(C)(C)C)C(CCO)C1"
},
"smiles": "COC(=O)N1CCN(C(=O)OC(C)(C)C)C(CCO)C1",
"reactionStepId": "sa_bd0c25f186b830855b27cc63",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20070167457A1;0127;475248\",\"rsmi\":\"Cl[C:3]([O:2][CH3:1])=[O:4].[NH:5]1[CH2:6][CH2:7][N:8]([C:9](=[O:10])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15])[CH:16]([CH2:17][CH2:18][OH:19])[CH2:20]1>CCN(CC)CC.ClCCl>[CH3:1][O:2][C:3](=[O:4])[N:5]1[CH2:6][CH2:7][N:8]([C:9](=[O:10])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15])[CH:16]([CH2:17][CH2:18][OH:19])[CH2:20]1\"},\"mapped_reaction_smiles\":\"Cl[C:3]([O:2][CH3:1])=[O:4].[NH:5]1[CH2:6][CH2:7][N:8]([C:9](=[O:10])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15])[CH:16]([CH2:17][CH2:18][OH:19])[CH2:20]1>CCN(CC)CC.ClCCl>[CH3:1][O:2][C:3](=[O:4])[N:5]1[CH2:6][CH2:7][N:8]([C:9](=[O:10])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15])[CH:16]([CH2:17][CH2:18][OH:19])[CH2:20]1\"}",
"reactionStep": {
"id": "sa_bd0c25f186b830855b27cc63",
"reactionHash": "d14727a250c221c7350b92bc4897c130be4ddd108dd4f9bec6e7c5fddfc8f461"
},
"children": [
{
"id": "12483",
"routeId": "sa_3f2f2879abc37a72be8708d4",
"moleculeId": "sa_dd6a7947abce6d3661946176",
"parentId": "12482",
"isLeaf": false,
"molecule": {
"id": "sa_dd6a7947abce6d3661946176",
"inchikey": "OOZBHDCFUFVAOH-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)N1CCNCC1CCO"
},
"smiles": "CC(C)(C)OC(=O)N1CCNCC1CCO",
"reactionStepId": "sa_2e48c57cdd49178ff2ee85e7",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20070167457A1;0126;475247\",\"rsmi\":\"c1ccc(C[N:11]2[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH:13]([CH2:14][CH2:15][OH:16])[CH2:12]2)cc1>CCO.[Pd]>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][NH:11][CH2:12][CH:13]1[CH2:14][CH2:15][OH:16]\"},\"mapped_reaction_smiles\":\"c1ccc(C[N:11]2[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH:13]([CH2:14][CH2:15][OH:16])[CH2:12]2)cc1>CCO.[Pd]>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][NH:11][CH2:12][CH:13]1[CH2:14][CH2:15][OH:16]\"}",
"reactionStep": {
"id": "sa_2e48c57cdd49178ff2ee85e7",
"reactionHash": "4f9c2ba3347c410c1040110d08234963a57eeddf1358a8ca012cb6b608861c6d"
},
"children": [
{
"id": "12484",
"routeId": "sa_3f2f2879abc37a72be8708d4",
"moleculeId": "sa_299c86d20dd2962de460c665",
"parentId": "12483",
"isLeaf": false,
"molecule": {
"id": "sa_299c86d20dd2962de460c665",
"inchikey": "YYTFROGXRPOCQX-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)N1CCN(Cc2ccccc2)CC1CCO"
},
"smiles": "CC(C)(C)OC(=O)N1CCN(Cc2ccccc2)CC1CCO",
"reactionStepId": "sa_93f31e93f92861b55eb7f0da",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20070167457A1;0125;475246\",\"rsmi\":\"CC(C)(C)OC(=O)O[C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7].[NH:8]1[CH2:9][CH2:10][N:11]([CH2:12][c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[CH2:19][CH:20]1[CH2:21][CH2:22][OH:23]>ClCCl>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][N:11]([CH2:12][c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[CH2:19][CH:20]1[CH2:21][CH2:22][OH:23]\"},\"mapped_reaction_smiles\":\"CC(C)(C)OC(=O)O[C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7].[NH:8]1[CH2:9][CH2:10][N:11]([CH2:12][c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[CH2:19][CH:20]1[CH2:21][CH2:22][OH:23]>ClCCl>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][N:11]([CH2:12][c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[CH2:19][CH:20]1[CH2:21][CH2:22][OH:23]\"}",
"reactionStep": {
"id": "sa_93f31e93f92861b55eb7f0da",
"reactionHash": "aa266b7fd1cf3d1e3ccd620a53f25f94ad78f164c22db70fc74fdc8ab6737a4e"
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"children": [
{
"id": "12485",
"routeId": "sa_3f2f2879abc37a72be8708d4",
"moleculeId": "sa_b273d4d4546165bca2b249b5",
"parentId": "12484",
"isLeaf": true,
"molecule": {
"id": "sa_b273d4d4546165bca2b249b5",
"inchikey": "DYHSDKLCOJIUFX-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)OC(=O)OC(C)(C)C"
},
"smiles": "CC(C)(C)OC(=O)OC(=O)OC(C)(C)C",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "12486",
"routeId": "sa_3f2f2879abc37a72be8708d4",
"moleculeId": "sa_2607f1ec251b7c49291683e1",
"parentId": "12484",
"isLeaf": true,
"molecule": {
"id": "sa_2607f1ec251b7c49291683e1",
"inchikey": "YIYKZUCYKKNQFH-UHFFFAOYSA-N",
"smiles": "OCCC1CN(Cc2ccccc2)CCN1"
},
"smiles": "OCCC1CN(Cc2ccccc2)CCN1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
},
{
"id": "12487",
"routeId": "sa_3f2f2879abc37a72be8708d4",
"moleculeId": "sa_786c6159be77bb31e43bff8a",
"parentId": "12482",
"isLeaf": true,
"molecule": {
"id": "sa_786c6159be77bb31e43bff8a",
"inchikey": "XMJHPCRAQCTCFT-UHFFFAOYSA-N",
"smiles": "COC(=O)Cl"
},
"smiles": "COC(=O)Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "12488",
"routeId": "sa_3f2f2879abc37a72be8708d4",
"moleculeId": "sa_2a52b4c246b479e8e6f1627e",
"parentId": "12481",
"isLeaf": true,
"molecule": {
"id": "sa_2a52b4c246b479e8e6f1627e",
"inchikey": "ISWSIDIOOBJBQZ-UHFFFAOYSA-N",
"smiles": "Oc1ccccc1"
},
"smiles": "Oc1ccccc1",
"reactionStepId": null,
"template": null,
"metadata": null,
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"children": []
}
]
}
]
}
]
}
}