Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CC(C)(C)[Si](C)(C)OC1=CCC(COc2ccc(S(C)(=O)=O)cc2F)CC1
InChiKey
ZPCCXUKGIUBSIU-UHFFFAOYSA-N
Route Signature
3fb2a9f58faaa33507777e4f6e9fb10a10e69bdfda50ffa2dfbfe7d927907017
Synthesis route with 6 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_9c99336859b41d2927305d38",
"signature": "3fb2a9f58faaa33507777e4f6e9fb10a10e69bdfda50ffa2dfbfe7d927907017",
"contentHash": "7ca2dea8b5d57160c69533f52601acf5306ee2a38345476e72239a2df4ce5095",
"length": 6,
"isConvergent": false
},
"target": {
"id": "sa_8ba0b825948f743ec04d49f7",
"benchmarkSetId": "f925e688d731a0ad4e3aa6a505df094f6d3ca64ce3facc312bc5f64731921b33",
"targetId": "n5-00298",
"moleculeId": "sa_1f2570ebe9b64307e9d343cb",
"smiles": "CC(C)(C)[Si](C)(C)OC1=CCC(COc2ccc(S(C)(=O)=O)cc2F)CC1",
"routeLength": 6,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_1f2570ebe9b64307e9d343cb",
"inchikey": "ZPCCXUKGIUBSIU-UHFFFAOYSA-N",
"smiles": "CC(C)(C)[Si](C)(C)OC1=CCC(COc2ccc(S(C)(=O)=O)cc2F)CC1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 3
},
"rootNode": {
"id": "3927",
"routeId": "sa_9c99336859b41d2927305d38",
"moleculeId": "sa_1f2570ebe9b64307e9d343cb",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_1f2570ebe9b64307e9d343cb",
"inchikey": "ZPCCXUKGIUBSIU-UHFFFAOYSA-N",
"smiles": "CC(C)(C)[Si](C)(C)OC1=CCC(COc2ccc(S(C)(=O)=O)cc2F)CC1"
},
"smiles": "CC(C)(C)[Si](C)(C)OC1=CCC(COc2ccc(S(C)(=O)=O)cc2F)CC1",
"reactionStepId": "sa_070cafd5ec5121acce84dfa1",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140066369A1;1156;1496287\",\"rsmi\":\"O=S(=O)(O[Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([CH3:6])[CH3:7])C(F)(F)F.[O:8]=[C:9]1[CH2:10][CH2:11][CH:12]([CH2:13][O:14][c:15]2[c:16]([F:17])[cH:18][c:19]([S:20]([CH3:21])(=[O:22])=[O:23])[cH:24][cH:25]2)[CH2:26][CH2:27]1>CCN(C(C)C)C(C)C.ClCCl.O>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][C:9]1=[CH:10][CH2:11][CH:12]([CH2:13][O:14][c:15]2[c:16]([F:17])[cH:18][c:19]([S:20]([CH3:21])(=[O:22])=[O:23])[cH:24][cH:25]2)[CH2:26][CH2:27]1\"},\"mapped_reaction_smiles\":\"O=S(=O)(O[Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([CH3:6])[CH3:7])C(F)(F)F.[O:8]=[C:9]1[CH2:10][CH2:11][CH:12]([CH2:13][O:14][c:15]2[c:16]([F:17])[cH:18][c:19]([S:20]([CH3:21])(=[O:22])=[O:23])[cH:24][cH:25]2)[CH2:26][CH2:27]1>CCN(C(C)C)C(C)C.ClCCl.O>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][C:9]1=[CH:10][CH2:11][CH:12]([CH2:13][O:14][c:15]2[c:16]([F:17])[cH:18][c:19]([S:20]([CH3:21])(=[O:22])=[O:23])[cH:24][cH:25]2)[CH2:26][CH2:27]1\"}",
"reactionStep": {
"id": "sa_070cafd5ec5121acce84dfa1",
"reactionHash": "693949652c09254dc2b2c8c2ad02c66998cdfdb695557c614015ec04f0efa9f1"
},
"children": [
{
"id": "3928",
"routeId": "sa_9c99336859b41d2927305d38",
"moleculeId": "sa_beeff4fc059ed550670530f4",
"parentId": "3927",
"isLeaf": false,
"molecule": {
"id": "sa_beeff4fc059ed550670530f4",
"inchikey": "MXBXZMZGHWFHFY-UHFFFAOYSA-N",
"smiles": "CS(=O)(=O)c1ccc(OCC2CCC(=O)CC2)c(F)c1"
},
"smiles": "CS(=O)(=O)c1ccc(OCC2CCC(=O)CC2)c(F)c1",
"reactionStepId": "sa_42eaeea241bf905d113e5af4",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140066369A1;1182;1496297\",\"rsmi\":\"C1C[O:16][C:15]2(O1)[CH2:14][CH2:13][CH:12]([CH2:11][O:10][c:9]1[c:7]([F:8])[cH:6][c:5]([S:2]([CH3:1])(=[O:3])=[O:4])[cH:20][cH:19]1)[CH2:18][CH2:17]2>C1CCOC1.Cl.O>[CH3:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][c:7]([F:8])[c:9]([O:10][CH2:11][CH:12]2[CH2:13][CH2:14][C:15](=[O:16])[CH2:17][CH2:18]2)[cH:19][cH:20]1\"},\"mapped_reaction_smiles\":\"C1C[O:16][C:15]2(O1)[CH2:14][CH2:13][CH:12]([CH2:11][O:10][c:9]1[c:7]([F:8])[cH:6][c:5]([S:2]([CH3:1])(=[O:3])=[O:4])[cH:20][cH:19]1)[CH2:18][CH2:17]2>C1CCOC1.Cl.O>[CH3:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][c:7]([F:8])[c:9]([O:10][CH2:11][CH:12]2[CH2:13][CH2:14][C:15](=[O:16])[CH2:17][CH2:18]2)[cH:19][cH:20]1\"}",
"reactionStep": {
"id": "sa_42eaeea241bf905d113e5af4",
"reactionHash": "ca326d8b47c5cc6dc9fd6dba2915d45d065760c2eaa6ba09d83f4fbf6ac44775"
},
"children": [
{
"id": "3929",
"routeId": "sa_9c99336859b41d2927305d38",
"moleculeId": "sa_7d46ccb26685ea04d8a4bd3f",
"parentId": "3928",
"isLeaf": false,
"molecule": {
"id": "sa_7d46ccb26685ea04d8a4bd3f",
"inchikey": "ROAMJGFKNPZKHL-UHFFFAOYSA-N",
"smiles": "CS(=O)(=O)c1ccc(OCC2CCC3(CC2)OCCO3)c(F)c1"
},
"smiles": "CS(=O)(=O)c1ccc(OCC2CCC3(CC2)OCCO3)c(F)c1",
"reactionStepId": "sa_19d189ff82cb6e5673fc0526",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140066369A1;1181;1496296\",\"rsmi\":\"CS(=O)(=O)O[CH2:11][CH:12]1[CH2:13][CH2:14][C:15]2([CH2:16][CH2:17]1)[O:18][CH2:19][CH2:20][O:21]2.[CH3:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][c:7]([F:8])[c:9]([OH:10])[cH:22][cH:23]1>CCOC(C)=O.CN(C)C=O.O=C(O)O.[Cs+].[Cs+]>[CH3:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][c:7]([F:8])[c:9]([O:10][CH2:11][CH:12]2[CH2:13][CH2:14][C:15]3([CH2:16][CH2:17]2)[O:18][CH2:19][CH2:20][O:21]3)[cH:22][cH:23]1\"},\"mapped_reaction_smiles\":\"CS(=O)(=O)O[CH2:11][CH:12]1[CH2:13][CH2:14][C:15]2([CH2:16][CH2:17]1)[O:18][CH2:19][CH2:20][O:21]2.[CH3:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][c:7]([F:8])[c:9]([OH:10])[cH:22][cH:23]1>CCOC(C)=O.CN(C)C=O.O=C(O)O.[Cs+].[Cs+]>[CH3:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][c:7]([F:8])[c:9]([O:10][CH2:11][CH:12]2[CH2:13][CH2:14][C:15]3([CH2:16][CH2:17]2)[O:18][CH2:19][CH2:20][O:21]3)[cH:22][cH:23]1\"}",
"reactionStep": {
"id": "sa_19d189ff82cb6e5673fc0526",
"reactionHash": "8d977a0c56dab0a40bbb828c041e6f982db8213b9d7cabf75bb7ab1a04b000c1"
},
"children": [
{
"id": "3930",
"routeId": "sa_9c99336859b41d2927305d38",
"moleculeId": "sa_c47febe30901dd2d474ec1ac",
"parentId": "3929",
"isLeaf": true,
"molecule": {
"id": "sa_c47febe30901dd2d474ec1ac",
"inchikey": "OVEMQCGVMRIIHW-UHFFFAOYSA-N",
"smiles": "CS(=O)(=O)c1ccc(O)c(F)c1"
},
"smiles": "CS(=O)(=O)c1ccc(O)c(F)c1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "3931",
"routeId": "sa_9c99336859b41d2927305d38",
"moleculeId": "sa_b37889e031cfef0c1d126685",
"parentId": "3929",
"isLeaf": false,
"molecule": {
"id": "sa_b37889e031cfef0c1d126685",
"inchikey": "PDQMFNUVJGFAEQ-UHFFFAOYSA-N",
"smiles": "CS(=O)(=O)OCC1CCC2(CC1)OCCO2"
},
"smiles": "CS(=O)(=O)OCC1CCC2(CC1)OCCO2",
"reactionStepId": "sa_d77d0d477a1d94df4aa3b2aa",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140066369A1;1180;1496295\",\"rsmi\":\"Cl[S:2]([CH3:1])(=[O:3])=[O:4].[OH:5][CH2:6][CH:7]1[CH2:8][CH2:9][C:10]2([CH2:11][CH2:12]1)[O:13][CH2:14][CH2:15][O:16]2>CCN(CC)CC.ClCCl>[CH3:1][S:2](=[O:3])(=[O:4])[O:5][CH2:6][CH:7]1[CH2:8][CH2:9][C:10]2([CH2:11][CH2:12]1)[O:13][CH2:14][CH2:15][O:16]2\"},\"mapped_reaction_smiles\":\"Cl[S:2]([CH3:1])(=[O:3])=[O:4].[OH:5][CH2:6][CH:7]1[CH2:8][CH2:9][C:10]2([CH2:11][CH2:12]1)[O:13][CH2:14][CH2:15][O:16]2>CCN(CC)CC.ClCCl>[CH3:1][S:2](=[O:3])(=[O:4])[O:5][CH2:6][CH:7]1[CH2:8][CH2:9][C:10]2([CH2:11][CH2:12]1)[O:13][CH2:14][CH2:15][O:16]2\"}",
"reactionStep": {
"id": "sa_d77d0d477a1d94df4aa3b2aa",
"reactionHash": "5131f1a9617356f9753caf369715a89bac77b836152340e28812e424ce0f4b9e"
},
"children": [
{
"id": "3932",
"routeId": "sa_9c99336859b41d2927305d38",
"moleculeId": "sa_d2a31ea58046b00856f61ca5",
"parentId": "3931",
"isLeaf": true,
"molecule": {
"id": "sa_d2a31ea58046b00856f61ca5",
"inchikey": "QARBMVPHQWIHKH-UHFFFAOYSA-N",
"smiles": "CS(=O)(=O)Cl"
},
"smiles": "CS(=O)(=O)Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "3933",
"routeId": "sa_9c99336859b41d2927305d38",
"moleculeId": "sa_ffbb857a95691b579038cbf0",
"parentId": "3931",
"isLeaf": false,
"molecule": {
"id": "sa_ffbb857a95691b579038cbf0",
"inchikey": "YXNMORHRGMYQKF-UHFFFAOYSA-N",
"smiles": "OCC1CCC2(CC1)OCCO2"
},
"smiles": "OCC1CCC2(CC1)OCCO2",
"reactionStepId": "sa_b5f9de085734c7a6dcc86324",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140066369A1;1179;1496294\",\"rsmi\":\"CCO[C:2](=[O:1])[CH:3]1[CH2:4][CH2:5][C:6]2([CH2:7][CH2:8]1)[O:9][CH2:10][CH2:11][O:12]2>C1CCOC1.B.[Li+]>[OH:1][CH2:2][CH:3]1[CH2:4][CH2:5][C:6]2([CH2:7][CH2:8]1)[O:9][CH2:10][CH2:11][O:12]2\"},\"mapped_reaction_smiles\":\"CCO[C:2](=[O:1])[CH:3]1[CH2:4][CH2:5][C:6]2([CH2:7][CH2:8]1)[O:9][CH2:10][CH2:11][O:12]2>C1CCOC1.B.[Li+]>[OH:1][CH2:2][CH:3]1[CH2:4][CH2:5][C:6]2([CH2:7][CH2:8]1)[O:9][CH2:10][CH2:11][O:12]2\"}",
"reactionStep": {
"id": "sa_b5f9de085734c7a6dcc86324",
"reactionHash": "03c5897950c54747a2bc1370ae7a6d98c37042651aa974de61e336a5e6be8505"
},
"children": [
{
"id": "3934",
"routeId": "sa_9c99336859b41d2927305d38",
"moleculeId": "sa_c95a8e64ff00f2f2988154bc",
"parentId": "3933",
"isLeaf": false,
"molecule": {
"id": "sa_c95a8e64ff00f2f2988154bc",
"inchikey": "UXXWGBLTOSRBAY-UHFFFAOYSA-N",
"smiles": "CCOC(=O)C1CCC2(CC1)OCCO2"
},
"smiles": "CCOC(=O)C1CCC2(CC1)OCCO2",
"reactionStepId": "sa_09c06e54ab8351e6e8c2a615",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140066369A1;1178;1496293\",\"rsmi\":\"O[CH2:13][CH2:14][OH:15].[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:7][CH2:8][C:9](=[O:12])[CH2:10][CH2:11]1>Cc1ccc(S(=O)(=O)O)cc1.Cc1ccccc1.O.O>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:7][CH2:8][C:9]2([CH2:10][CH2:11]1)[O:12][CH2:13][CH2:14][O:15]2\"},\"mapped_reaction_smiles\":\"O[CH2:13][CH2:14][OH:15].[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:7][CH2:8][C:9](=[O:12])[CH2:10][CH2:11]1>Cc1ccc(S(=O)(=O)O)cc1.Cc1ccccc1.O.O>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:7][CH2:8][C:9]2([CH2:10][CH2:11]1)[O:12][CH2:13][CH2:14][O:15]2\"}",
"reactionStep": {
"id": "sa_09c06e54ab8351e6e8c2a615",
"reactionHash": "efbb07f823d9de8efe54b1983229bf8b5b0ef44d52fe085fb3f53d713d4c93d2"
},
"children": [
{
"id": "3935",
"routeId": "sa_9c99336859b41d2927305d38",
"moleculeId": "sa_daa2686ce35f5333036b911a",
"parentId": "3934",
"isLeaf": true,
"molecule": {
"id": "sa_daa2686ce35f5333036b911a",
"inchikey": "LYCAIKOWRPUZTN-UHFFFAOYSA-N",
"smiles": "OCCO"
},
"smiles": "OCCO",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "3936",
"routeId": "sa_9c99336859b41d2927305d38",
"moleculeId": "sa_f570bbe35c9787d7cf1cc093",
"parentId": "3934",
"isLeaf": true,
"molecule": {
"id": "sa_f570bbe35c9787d7cf1cc093",
"inchikey": "ZXYAWONOWHSQRU-UHFFFAOYSA-N",
"smiles": "CCOC(=O)C1CCC(=O)CC1"
},
"smiles": "CCOC(=O)C1CCC(=O)CC1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
]
}
]
}
]
},
{
"id": "3937",
"routeId": "sa_9c99336859b41d2927305d38",
"moleculeId": "sa_8bbbc81e89f5805160771988",
"parentId": "3927",
"isLeaf": true,
"molecule": {
"id": "sa_8bbbc81e89f5805160771988",
"inchikey": "WLLIXJBWWFGEHT-UHFFFAOYSA-N",
"smiles": "CC(C)(C)[Si](C)(C)OS(=O)(=O)C(F)(F)F"
},
"smiles": "CC(C)(C)[Si](C)(C)OS(=O)(=O)C(F)(F)F",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
}