Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
O=C(O)c1c[nH]c2cc(F)c(-c3ccc(OCCO)cc3)c(F)c12
InChiKey
QWKKIHLNFWNSMF-UHFFFAOYSA-N
Route Signature
57071f4cbc51d4ab6db7153b62b83edd699820da330d6054de63931b64984886
Synthesis route with 4 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_2cdd0a37706b954f535b30b0",
"signature": "57071f4cbc51d4ab6db7153b62b83edd699820da330d6054de63931b64984886",
"contentHash": "267687646092437a76577f7e06b9ec907b7152352357306ed4463e21a349743c",
"length": 4,
"isConvergent": true
},
"target": {
"id": "sa_8177e8c5d3d7dc8dd3f53eb9",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-02346",
"moleculeId": "sa_cdca7795d7138c97f2a148ac",
"smiles": "O=C(O)c1c[nH]c2cc(F)c(-c3ccc(OCCO)cc3)c(F)c12",
"routeLength": 4,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_cdca7795d7138c97f2a148ac",
"inchikey": "QWKKIHLNFWNSMF-UHFFFAOYSA-N",
"smiles": "O=C(O)c1c[nH]c2cc(F)c(-c3ccc(OCCO)cc3)c(F)c12"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "10703",
"routeId": "sa_2cdd0a37706b954f535b30b0",
"moleculeId": "sa_cdca7795d7138c97f2a148ac",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_cdca7795d7138c97f2a148ac",
"inchikey": "QWKKIHLNFWNSMF-UHFFFAOYSA-N",
"smiles": "O=C(O)c1c[nH]c2cc(F)c(-c3ccc(OCCO)cc3)c(F)c12"
},
"smiles": "O=C(O)c1c[nH]c2cc(F)c(-c3ccc(OCCO)cc3)c(F)c12",
"reactionStepId": "sa_da2a4fcf16176d77f27a72db",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160016940A1;0821;1821871\",\"rsmi\":\"O[Cl+][O-:3].[O:1]=[CH:2][c:4]1[cH:5][nH:6][c:7]2[cH:8][c:9]([F:10])[c:11](-[c:12]3[cH:13][cH:14][c:15]([O:16][CH2:17][CH2:18][OH:19])[cH:20][cH:21]3)[c:22]([F:23])[c:24]12>CC#N.CC(C)(C)O.CC=C(C)C.O.O=P(O)(O)O.O=S(O)O.[Na+].[Na+].[Na+].[Na+]>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][nH:6][c:7]2[cH:8][c:9]([F:10])[c:11](-[c:12]3[cH:13][cH:14][c:15]([O:16][CH2:17][CH2:18][OH:19])[cH:20][cH:21]3)[c:22]([F:23])[c:24]12\"},\"mapped_reaction_smiles\":\"O[Cl+][O-:3].[O:1]=[CH:2][c:4]1[cH:5][nH:6][c:7]2[cH:8][c:9]([F:10])[c:11](-[c:12]3[cH:13][cH:14][c:15]([O:16][CH2:17][CH2:18][OH:19])[cH:20][cH:21]3)[c:22]([F:23])[c:24]12>CC#N.CC(C)(C)O.CC=C(C)C.O.O=P(O)(O)O.O=S(O)O.[Na+].[Na+].[Na+].[Na+]>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][nH:6][c:7]2[cH:8][c:9]([F:10])[c:11](-[c:12]3[cH:13][cH:14][c:15]([O:16][CH2:17][CH2:18][OH:19])[cH:20][cH:21]3)[c:22]([F:23])[c:24]12\"}",
"reactionStep": {
"id": "sa_da2a4fcf16176d77f27a72db",
"reactionHash": "98360b995eead59378d04091dc195aaaaeecb560227027b195fd78ed73c11d0b"
},
"children": [
{
"id": "10704",
"routeId": "sa_2cdd0a37706b954f535b30b0",
"moleculeId": "sa_a8aaad1a19a01d46c6a8c07a",
"parentId": "10703",
"isLeaf": true,
"molecule": {
"id": "sa_a8aaad1a19a01d46c6a8c07a",
"inchikey": "NPWPEPVYKMPDKK-UHFFFAOYSA-N",
"smiles": "[O-][Cl+]O"
},
"smiles": "[O-][Cl+]O",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "10705",
"routeId": "sa_2cdd0a37706b954f535b30b0",
"moleculeId": "sa_10f40b7265a7cc7ce353e479",
"parentId": "10703",
"isLeaf": false,
"molecule": {
"id": "sa_10f40b7265a7cc7ce353e479",
"inchikey": "WHHNFVIYWWUFIJ-UHFFFAOYSA-N",
"smiles": "O=Cc1c[nH]c2cc(F)c(-c3ccc(OCCO)cc3)c(F)c12"
},
"smiles": "O=Cc1c[nH]c2cc(F)c(-c3ccc(OCCO)cc3)c(F)c12",
"reactionStepId": "sa_ce2c21f1be1b2cd52e56d756",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160016940A1;0819;1821870\",\"rsmi\":\"Br[c:10]1[c:8]([F:9])[cH:7][c:6]2[nH:5][cH:4][c:3]([CH:2]=[O:1])[c:23]2[c:21]1[F:22].CC1(C)COB([c:11]2[cH:12][cH:13][c:14]([O:15][CH2:16][CH2:17][OH:18])[cH:19][cH:20]2)OC1>CCO.Cc1ccccc1.Cl[Pd]Cl.O.O=C(O)O.[Fe+2].[K+].[K+]>[O:1]=[CH:2][c:3]1[cH:4][nH:5][c:6]2[cH:7][c:8]([F:9])[c:10](-[c:11]3[cH:12][cH:13][c:14]([O:15][CH2:16][CH2:17][OH:18])[cH:19][cH:20]3)[c:21]([F:22])[c:23]12\"},\"mapped_reaction_smiles\":\"Br[c:10]1[c:8]([F:9])[cH:7][c:6]2[nH:5][cH:4][c:3]([CH:2]=[O:1])[c:23]2[c:21]1[F:22].CC1(C)COB([c:11]2[cH:12][cH:13][c:14]([O:15][CH2:16][CH2:17][OH:18])[cH:19][cH:20]2)OC1>CCO.Cc1ccccc1.Cl[Pd]Cl.O.O=C(O)O.[Fe+2].[K+].[K+]>[O:1]=[CH:2][c:3]1[cH:4][nH:5][c:6]2[cH:7][c:8]([F:9])[c:10](-[c:11]3[cH:12][cH:13][c:14]([O:15][CH2:16][CH2:17][OH:18])[cH:19][cH:20]3)[c:21]([F:22])[c:23]12\"}",
"reactionStep": {
"id": "sa_ce2c21f1be1b2cd52e56d756",
"reactionHash": "f783c4633cf350d3f2fe2ccdc62a5940ca98fc061f6d770d86bdd51bbf24d6fc"
},
"children": [
{
"id": "10706",
"routeId": "sa_2cdd0a37706b954f535b30b0",
"moleculeId": "sa_075a6146c83e64aee3c85c85",
"parentId": "10705",
"isLeaf": false,
"molecule": {
"id": "sa_075a6146c83e64aee3c85c85",
"inchikey": "PBRRUXMVGWLRMN-UHFFFAOYSA-N",
"smiles": "CC1(C)COB(c2ccc(OCCO)cc2)OC1"
},
"smiles": "CC1(C)COB(c2ccc(OCCO)cc2)OC1",
"reactionStepId": "sa_9220c54ab45ab467fd9a4fde",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160016940A1;0818;1821869\",\"rsmi\":\"Br[c:7]1[cH:8][cH:9][c:10]([O:11][CH2:12][CH2:13][OH:14])[cH:15][cH:16]1.CC1(C)COB([B:6]2[O:5][CH2:4][C:2]([CH3:1])([CH3:3])[CH2:18][O:17]2)OC1>C1COCCO1.CC(=O)O.CCOC(C)=O.ClCCl.Cl[Pd]Cl.[Fe+2].[K+]>[CH3:1][C:2]1([CH3:3])[CH2:4][O:5][B:6]([c:7]2[cH:8][cH:9][c:10]([O:11][CH2:12][CH2:13][OH:14])[cH:15][cH:16]2)[O:17][CH2:18]1\"},\"mapped_reaction_smiles\":\"Br[c:7]1[cH:8][cH:9][c:10]([O:11][CH2:12][CH2:13][OH:14])[cH:15][cH:16]1.CC1(C)COB([B:6]2[O:5][CH2:4][C:2]([CH3:1])([CH3:3])[CH2:18][O:17]2)OC1>C1COCCO1.CC(=O)O.CCOC(C)=O.ClCCl.Cl[Pd]Cl.[Fe+2].[K+]>[CH3:1][C:2]1([CH3:3])[CH2:4][O:5][B:6]([c:7]2[cH:8][cH:9][c:10]([O:11][CH2:12][CH2:13][OH:14])[cH:15][cH:16]2)[O:17][CH2:18]1\"}",
"reactionStep": {
"id": "sa_9220c54ab45ab467fd9a4fde",
"reactionHash": "0724c2ee48e4bbddf100034fb77926dedaa6070739656c9b744c202903d63372"
},
"children": [
{
"id": "10707",
"routeId": "sa_2cdd0a37706b954f535b30b0",
"moleculeId": "sa_1127e753c784ae00c70b637a",
"parentId": "10706",
"isLeaf": true,
"molecule": {
"id": "sa_1127e753c784ae00c70b637a",
"inchikey": "MDNDJMCSXOXBFZ-UHFFFAOYSA-N",
"smiles": "CC1(C)COB(B2OCC(C)(C)CO2)OC1"
},
"smiles": "CC1(C)COB(B2OCC(C)(C)CO2)OC1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "10708",
"routeId": "sa_2cdd0a37706b954f535b30b0",
"moleculeId": "sa_2dd8b43de36acb55f56ceba4",
"parentId": "10706",
"isLeaf": true,
"molecule": {
"id": "sa_2dd8b43de36acb55f56ceba4",
"inchikey": "QYIOGYCRGNHDNK-UHFFFAOYSA-N",
"smiles": "OCCOc1ccc(Br)cc1"
},
"smiles": "OCCOc1ccc(Br)cc1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "10709",
"routeId": "sa_2cdd0a37706b954f535b30b0",
"moleculeId": "sa_26103cf3d68ccd4ec4df526c",
"parentId": "10705",
"isLeaf": false,
"molecule": {
"id": "sa_26103cf3d68ccd4ec4df526c",
"inchikey": "TYAQPYDGPZQCHY-UHFFFAOYSA-N",
"smiles": "O=Cc1c[nH]c2cc(F)c(Br)c(F)c12"
},
"smiles": "O=Cc1c[nH]c2cc(F)c(Br)c(F)c12",
"reactionStepId": "sa_04fd71492ac09050ed0b48ec",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160016940A1;0801;1821857\",\"rsmi\":\"CN(C)[CH:2]=[O:1].[cH:3]1[cH:4][nH:5][c:6]2[cH:7][c:8]([F:9])[c:10]([Br:11])[c:12]([F:13])[c:14]12>C[N+](C)=CCl.O.[Na+].O>[O:1]=[CH:2][c:3]1[cH:4][nH:5][c:6]2[cH:7][c:8]([F:9])[c:10]([Br:11])[c:12]([F:13])[c:14]12\"},\"mapped_reaction_smiles\":\"CN(C)[CH:2]=[O:1].[cH:3]1[cH:4][nH:5][c:6]2[cH:7][c:8]([F:9])[c:10]([Br:11])[c:12]([F:13])[c:14]12>C[N+](C)=CCl.O.[Na+].O>[O:1]=[CH:2][c:3]1[cH:4][nH:5][c:6]2[cH:7][c:8]([F:9])[c:10]([Br:11])[c:12]([F:13])[c:14]12\"}",
"reactionStep": {
"id": "sa_04fd71492ac09050ed0b48ec",
"reactionHash": "840103856180dc9168ec1d09a052253c029a961282daa63f59205f31d3d57e4c"
},
"children": [
{
"id": "10710",
"routeId": "sa_2cdd0a37706b954f535b30b0",
"moleculeId": "sa_6acd60d13d23635b7410774d",
"parentId": "10709",
"isLeaf": false,
"molecule": {
"id": "sa_6acd60d13d23635b7410774d",
"inchikey": "WLQCUDABSXTYOM-UHFFFAOYSA-N",
"smiles": "Fc1cc2[nH]ccc2c(F)c1Br"
},
"smiles": "Fc1cc2[nH]ccc2c(F)c1Br",
"reactionStepId": "sa_50639e5f6a4f851c33833f18",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160016940A1;0712;1821796\",\"rsmi\":\"[F:1][c:2]1[c:3]([Br:4])[c:5]([F:6])[c:7]2[c:11]([cH:12]1)[NH:10][CH2:9][CH2:8]2>ClC(Cl)Cl.[Mn+4].[O-2].[O-2]>[F:1][c:2]1[c:3]([Br:4])[c:5]([F:6])[c:7]2[cH:8][cH:9][nH:10][c:11]2[cH:12]1\"},\"mapped_reaction_smiles\":\"[F:1][c:2]1[c:3]([Br:4])[c:5]([F:6])[c:7]2[c:11]([cH:12]1)[NH:10][CH2:9][CH2:8]2>ClC(Cl)Cl.[Mn+4].[O-2].[O-2]>[F:1][c:2]1[c:3]([Br:4])[c:5]([F:6])[c:7]2[cH:8][cH:9][nH:10][c:11]2[cH:12]1\"}",
"reactionStep": {
"id": "sa_50639e5f6a4f851c33833f18",
"reactionHash": "780fe9ccee90f7e07d8915a20a6c52d4ad991fd5bd5fb714374f7e4befd4fe10"
},
"children": [
{
"id": "10711",
"routeId": "sa_2cdd0a37706b954f535b30b0",
"moleculeId": "sa_0ecdaee473f6122cd3b04347",
"parentId": "10710",
"isLeaf": true,
"molecule": {
"id": "sa_0ecdaee473f6122cd3b04347",
"inchikey": "YQCGGHBHEVDDAV-UHFFFAOYSA-N",
"smiles": "Fc1cc2c(c(F)c1Br)CCN2"
},
"smiles": "Fc1cc2c(c(F)c1Br)CCN2",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "10712",
"routeId": "sa_2cdd0a37706b954f535b30b0",
"moleculeId": "sa_e0b5e93d36242e79e81ef68c",
"parentId": "10709",
"isLeaf": true,
"molecule": {
"id": "sa_e0b5e93d36242e79e81ef68c",
"inchikey": "ZMXDDKWLCZADIW-UHFFFAOYSA-N",
"smiles": "CN(C)C=O"
},
"smiles": "CN(C)C=O",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
]
}
}