Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
COc1cccc(F)c1C1CC(C)C(=O)N1Cc1ccnc(-c2nc(C)cs2)c1
InChiKey
XJIWMKOGXNSCLB-UHFFFAOYSA-N
Route Signature
7d7d592dd2996c6b38e7158d1dc8ae94448545766107aade23ffab9488171665
Synthesis route with 4 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_08d7303430ce2854c2130d27",
"signature": "7d7d592dd2996c6b38e7158d1dc8ae94448545766107aade23ffab9488171665",
"contentHash": "6d8731e6a788a129ed0a465937201072a29a318c84e9d2eb6f4d8d14bbe00465",
"length": 4,
"isConvergent": true
},
"target": {
"id": "sa_a6c845537c05b76269769220",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-05889",
"moleculeId": "sa_2b14934304f4aa9e733e061e",
"smiles": "COc1cccc(F)c1C1CC(C)C(=O)N1Cc1ccnc(-c2nc(C)cs2)c1",
"routeLength": 4,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_2b14934304f4aa9e733e061e",
"inchikey": "XJIWMKOGXNSCLB-UHFFFAOYSA-N",
"smiles": "COc1cccc(F)c1C1CC(C)C(=O)N1Cc1ccnc(-c2nc(C)cs2)c1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "11491",
"routeId": "sa_08d7303430ce2854c2130d27",
"moleculeId": "sa_2b14934304f4aa9e733e061e",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_2b14934304f4aa9e733e061e",
"inchikey": "XJIWMKOGXNSCLB-UHFFFAOYSA-N",
"smiles": "COc1cccc(F)c1C1CC(C)C(=O)N1Cc1ccnc(-c2nc(C)cs2)c1"
},
"smiles": "COc1cccc(F)c1C1CC(C)C(=O)N1Cc1ccnc(-c2nc(C)cs2)c1",
"reactionStepId": "sa_b7f5d5f42f95301d0657c8f6",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130237525A1;1207;1420166\",\"rsmi\":\"CCO[C:14]([CH:12]([CH2:11][CH:10]([c:9]1[c:3]([O:2][CH3:1])[cH:4][cH:5][cH:6][c:7]1[F:8])[NH2:16])[CH3:13])=[O:15].O=[CH:17][c:18]1[cH:19][c:20](-[c:21]2[n:22][c:23]([CH3:24])[cH:25][s:26]2)[n:27][cH:28][cH:29]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([F:8])[c:9]1[CH:10]1[CH2:11][CH:12]([CH3:13])[C:14](=[O:15])[N:16]1[CH2:17][c:18]1[cH:19][c:20](-[c:21]2[n:22][c:23]([CH3:24])[cH:25][s:26]2)[n:27][cH:28][cH:29]1\"},\"mapped_reaction_smiles\":\"CCO[C:14]([CH:12]([CH2:11][CH:10]([c:9]1[c:3]([O:2][CH3:1])[cH:4][cH:5][cH:6][c:7]1[F:8])[NH2:16])[CH3:13])=[O:15].O=[CH:17][c:18]1[cH:19][c:20](-[c:21]2[n:22][c:23]([CH3:24])[cH:25][s:26]2)[n:27][cH:28][cH:29]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([F:8])[c:9]1[CH:10]1[CH2:11][CH:12]([CH3:13])[C:14](=[O:15])[N:16]1[CH2:17][c:18]1[cH:19][c:20](-[c:21]2[n:22][c:23]([CH3:24])[cH:25][s:26]2)[n:27][cH:28][cH:29]1\"}",
"reactionStep": {
"id": "sa_b7f5d5f42f95301d0657c8f6",
"reactionHash": "01d61f130ba620cf103f13f52e8479217cc2d5da96eeb21d7171435aed9ba828"
},
"children": [
{
"id": "11492",
"routeId": "sa_08d7303430ce2854c2130d27",
"moleculeId": "sa_65408a455a8fc88e2c9c2c7c",
"parentId": "11491",
"isLeaf": false,
"molecule": {
"id": "sa_65408a455a8fc88e2c9c2c7c",
"inchikey": "CEJIFBMUDTWWFE-UHFFFAOYSA-N",
"smiles": "Cc1csc(-c2cc(C=O)ccn2)n1"
},
"smiles": "Cc1csc(-c2cc(C=O)ccn2)n1",
"reactionStepId": "sa_5c4eacb3e0a5bfd7305a799a",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130237525A1;0653;1419759\",\"rsmi\":\"[CH3:1][c:2]1[cH:3][s:4][c:5](-[c:6]2[n:7][cH:8][cH:9][c:10]([CH2:11][OH:12])[cH:13]2)[n:14]1>ClCCCl.O=[Mn]=O>[CH3:1][c:2]1[cH:3][s:4][c:5](-[c:6]2[n:7][cH:8][cH:9][c:10]([CH:11]=[O:12])[cH:13]2)[n:14]1\"},\"mapped_reaction_smiles\":\"[CH3:1][c:2]1[cH:3][s:4][c:5](-[c:6]2[n:7][cH:8][cH:9][c:10]([CH2:11][OH:12])[cH:13]2)[n:14]1>ClCCCl.O=[Mn]=O>[CH3:1][c:2]1[cH:3][s:4][c:5](-[c:6]2[n:7][cH:8][cH:9][c:10]([CH:11]=[O:12])[cH:13]2)[n:14]1\"}",
"reactionStep": {
"id": "sa_5c4eacb3e0a5bfd7305a799a",
"reactionHash": "ee1e01ec14b714625efbbe8bcf3f233fb366b0644c82d18c1e3957753127dd79"
},
"children": [
{
"id": "11493",
"routeId": "sa_08d7303430ce2854c2130d27",
"moleculeId": "sa_1d80b4a5dbc4f220f6cfc1c6",
"parentId": "11492",
"isLeaf": false,
"molecule": {
"id": "sa_1d80b4a5dbc4f220f6cfc1c6",
"inchikey": "OSTZMWOWKMQHPI-UHFFFAOYSA-N",
"smiles": "Cc1csc(-c2cc(CO)ccn2)n1"
},
"smiles": "Cc1csc(-c2cc(CO)ccn2)n1",
"reactionStepId": "sa_3a174f6cfa24ffebb6915fdc",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130237525A1;0652;1419758\",\"rsmi\":\"CO[C:11]([c:10]1[cH:9][cH:8][n:7][c:6](-[c:5]2[s:4][cH:3][c:2]([CH3:1])[n:14]2)[cH:13]1)=[O:12]>CO.B.[Na+]>[CH3:1][c:2]1[cH:3][s:4][c:5](-[c:6]2[n:7][cH:8][cH:9][c:10]([CH2:11][OH:12])[cH:13]2)[n:14]1\"},\"mapped_reaction_smiles\":\"CO[C:11]([c:10]1[cH:9][cH:8][n:7][c:6](-[c:5]2[s:4][cH:3][c:2]([CH3:1])[n:14]2)[cH:13]1)=[O:12]>CO.B.[Na+]>[CH3:1][c:2]1[cH:3][s:4][c:5](-[c:6]2[n:7][cH:8][cH:9][c:10]([CH2:11][OH:12])[cH:13]2)[n:14]1\"}",
"reactionStep": {
"id": "sa_3a174f6cfa24ffebb6915fdc",
"reactionHash": "674c659b501df7232d10c778516d683345e6d156b8cd2b20b4edfb404e4636fc"
},
"children": [
{
"id": "11494",
"routeId": "sa_08d7303430ce2854c2130d27",
"moleculeId": "sa_3e8555c9264898fb917e13e0",
"parentId": "11493",
"isLeaf": false,
"molecule": {
"id": "sa_3e8555c9264898fb917e13e0",
"inchikey": "KRONQPLREOSAER-UHFFFAOYSA-N",
"smiles": "COC(=O)c1ccnc(-c2nc(C)cs2)c1"
},
"smiles": "COC(=O)c1ccnc(-c2nc(C)cs2)c1",
"reactionStepId": "sa_cbc2c89ef250b1ceaacd0f94",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130237525A1;0651;1419757\",\"rsmi\":\"Br[c:7]1[cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:16][cH:15][n:14]1.CCCC[Sn](CCCC)(CCCC)[c:8]1[n:9][c:10]([CH3:11])[cH:12][s:13]1>CN(C)C=O.c1ccc([PH](c2ccccc2)(c2ccccc2)[Pd]([PH](c2ccccc2)(c2ccccc2)c2ccccc2)([PH](c2ccccc2)(c2ccccc2)c2ccccc2)[PH](c2ccccc2)(c2ccccc2)c2ccccc2)cc1>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7](-[c:8]2[n:9][c:10]([CH3:11])[cH:12][s:13]2)[n:14][cH:15][cH:16]1\"},\"mapped_reaction_smiles\":\"Br[c:7]1[cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:16][cH:15][n:14]1.CCCC[Sn](CCCC)(CCCC)[c:8]1[n:9][c:10]([CH3:11])[cH:12][s:13]1>CN(C)C=O.c1ccc([PH](c2ccccc2)(c2ccccc2)[Pd]([PH](c2ccccc2)(c2ccccc2)c2ccccc2)([PH](c2ccccc2)(c2ccccc2)c2ccccc2)[PH](c2ccccc2)(c2ccccc2)c2ccccc2)cc1>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7](-[c:8]2[n:9][c:10]([CH3:11])[cH:12][s:13]2)[n:14][cH:15][cH:16]1\"}",
"reactionStep": {
"id": "sa_cbc2c89ef250b1ceaacd0f94",
"reactionHash": "c433707997559a89b8dce90bb09b24daa3d288b127ab5d9aa7ff14c66c16002c"
},
"children": [
{
"id": "11495",
"routeId": "sa_08d7303430ce2854c2130d27",
"moleculeId": "sa_c0bb494c5c101c997ce3e469",
"parentId": "11494",
"isLeaf": true,
"molecule": {
"id": "sa_c0bb494c5c101c997ce3e469",
"inchikey": "MULLTHQTADMZDM-UHFFFAOYSA-N",
"smiles": "COC(=O)c1ccnc(Br)c1"
},
"smiles": "COC(=O)c1ccnc(Br)c1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "11496",
"routeId": "sa_08d7303430ce2854c2130d27",
"moleculeId": "sa_67d2f711c3518bbaa7289e0f",
"parentId": "11494",
"isLeaf": true,
"molecule": {
"id": "sa_67d2f711c3518bbaa7289e0f",
"inchikey": "PZPGNMUMILSRSX-UHFFFAOYSA-N",
"smiles": "CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1nc(C)cs1"
},
"smiles": "CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1nc(C)cs1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
]
},
{
"id": "11497",
"routeId": "sa_08d7303430ce2854c2130d27",
"moleculeId": "sa_bf02a309485f25795085db3a",
"parentId": "11491",
"isLeaf": false,
"molecule": {
"id": "sa_bf02a309485f25795085db3a",
"inchikey": "KCUGWGLSLAWZAN-UHFFFAOYSA-N",
"smiles": "CCOC(=O)C(C)CC(N)c1c(F)cccc1OC"
},
"smiles": "CCOC(=O)C(C)CC(N)c1c(F)cccc1OC",
"reactionStepId": "sa_7d8740a40936f44d3699223a",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130237525A1;0732;1419825\",\"rsmi\":\"CC(C)(C)S(=O)[NH:10][CH:9]([CH2:8][CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH3:7])[c:11]1[c:12]([F:13])[cH:14][cH:15][cH:16][c:17]1[O:18][CH3:19]>C1COCCO1.CCO.Cl>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH3:7])[CH2:8][CH:9]([NH2:10])[c:11]1[c:12]([F:13])[cH:14][cH:15][cH:16][c:17]1[O:18][CH3:19]\"},\"mapped_reaction_smiles\":\"CC(C)(C)S(=O)[NH:10][CH:9]([CH2:8][CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH3:7])[c:11]1[c:12]([F:13])[cH:14][cH:15][cH:16][c:17]1[O:18][CH3:19]>C1COCCO1.CCO.Cl>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH3:7])[CH2:8][CH:9]([NH2:10])[c:11]1[c:12]([F:13])[cH:14][cH:15][cH:16][c:17]1[O:18][CH3:19]\"}",
"reactionStep": {
"id": "sa_7d8740a40936f44d3699223a",
"reactionHash": "91afe8d2cb06963ce20337feb924661a3d1ce8649c1e235b0592360cad6fb2cc"
},
"children": [
{
"id": "11498",
"routeId": "sa_08d7303430ce2854c2130d27",
"moleculeId": "sa_689a52d11fb494156581e65f",
"parentId": "11497",
"isLeaf": true,
"molecule": {
"id": "sa_689a52d11fb494156581e65f",
"inchikey": "LKRRWYZRWNSFBL-UHFFFAOYSA-N",
"smiles": "CCOC(=O)C(C)CC(NS(=O)C(C)(C)C)c1c(F)cccc1OC"
},
"smiles": "CCOC(=O)C(C)CC(NS(=O)C(C)(C)C)c1c(F)cccc1OC",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
}