Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
COC(=O)c1nc(-c2ccc3c(c2)NCCC3)ccc1OCCOc1ccccc1
InChiKey
WANCVFFMAWXYSP-UHFFFAOYSA-N
Route Signature
8ca163b1bc792c5ee5c8c948407d0efe6ee6cf8a2696ef292ca8eaf0e8bb9ce1
Synthesis route with 4 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_21260b0433e7515b69add67b",
"signature": "8ca163b1bc792c5ee5c8c948407d0efe6ee6cf8a2696ef292ca8eaf0e8bb9ce1",
"contentHash": "936ca4b207e2f8a41a8af430b8adc191a19d67edf015aac9cf99d5ced940227d",
"length": 4,
"isConvergent": true
},
"target": {
"id": "sa_46a8c74e076a104f3c4f9cd2",
"benchmarkSetId": "7390a9c2522b1c81605e80a42a8de7c7ad9a5797d028633b54904bc78f091bb8",
"targetId": "n5-02289",
"moleculeId": "sa_55c88039e0569030152f5873",
"smiles": "COC(=O)c1nc(-c2ccc3c(c2)NCCC3)ccc1OCCOc1ccccc1",
"routeLength": 4,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_55c88039e0569030152f5873",
"inchikey": "WANCVFFMAWXYSP-UHFFFAOYSA-N",
"smiles": "COC(=O)c1nc(-c2ccc3c(c2)NCCC3)ccc1OCCOc1ccccc1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 6
},
"rootNode": {
"id": "1808",
"routeId": "sa_21260b0433e7515b69add67b",
"moleculeId": "sa_55c88039e0569030152f5873",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_55c88039e0569030152f5873",
"inchikey": "WANCVFFMAWXYSP-UHFFFAOYSA-N",
"smiles": "COC(=O)c1nc(-c2ccc3c(c2)NCCC3)ccc1OCCOc1ccccc1"
},
"smiles": "COC(=O)c1nc(-c2ccc3c(c2)NCCC3)ccc1OCCOc1ccccc1",
"reactionStepId": "sa_05e808496752e1da7b0600d8",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140005190A1;0334;1468334\",\"rsmi\":\"Br[c:7]1[n:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[c:20]([O:21][CH2:22][CH2:23][O:24][c:25]2[cH:26][cH:27][cH:28][cH:29][cH:30]2)[cH:19][cH:18]1.CC1(C)OB([c:8]2[cH:9][cH:10][c:11]3[c:16]([cH:17]2)[NH:15][CH2:14][CH2:13][CH2:12]3)OC1(C)C>C1COCCO1.CCCC[N+](CCCC)(CCCC)CCCC.CCOC(C)=O.Cl[Pd](Cl)([PH](c1ccccc1)(c1ccccc1)c1ccccc1)[PH](c1ccccc1)(c1ccccc1)c1ccccc1.O.O=C(O)O.Br.[K+].[K+]>[CH3:1][O:2][C:3](=[O:4])[c:5]1[n:6][c:7](-[c:8]2[cH:9][cH:10][c:11]3[c:16]([cH:17]2)[NH:15][CH2:14][CH2:13][CH2:12]3)[cH:18][cH:19][c:20]1[O:21][CH2:22][CH2:23][O:24][c:25]1[cH:26][cH:27][cH:28][cH:29][cH:30]1\"},\"mapped_reaction_smiles\":\"Br[c:7]1[n:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[c:20]([O:21][CH2:22][CH2:23][O:24][c:25]2[cH:26][cH:27][cH:28][cH:29][cH:30]2)[cH:19][cH:18]1.CC1(C)OB([c:8]2[cH:9][cH:10][c:11]3[c:16]([cH:17]2)[NH:15][CH2:14][CH2:13][CH2:12]3)OC1(C)C>C1COCCO1.CCCC[N+](CCCC)(CCCC)CCCC.CCOC(C)=O.Cl[Pd](Cl)([PH](c1ccccc1)(c1ccccc1)c1ccccc1)[PH](c1ccccc1)(c1ccccc1)c1ccccc1.O.O=C(O)O.Br.[K+].[K+]>[CH3:1][O:2][C:3](=[O:4])[c:5]1[n:6][c:7](-[c:8]2[cH:9][cH:10][c:11]3[c:16]([cH:17]2)[NH:15][CH2:14][CH2:13][CH2:12]3)[cH:18][cH:19][c:20]1[O:21][CH2:22][CH2:23][O:24][c:25]1[cH:26][cH:27][cH:28][cH:29][cH:30]1\"}",
"reactionStep": {
"id": "sa_05e808496752e1da7b0600d8",
"reactionHash": "aa4e158319e1d46b79388f1746b0ccc99d9ab0e33eec54733892fdd3fbea1f05"
},
"children": [
{
"id": "1809",
"routeId": "sa_21260b0433e7515b69add67b",
"moleculeId": "sa_0fdae051f806031909c703d7",
"parentId": "1808",
"isLeaf": false,
"molecule": {
"id": "sa_0fdae051f806031909c703d7",
"inchikey": "GIWFSESZFIZJQP-UHFFFAOYSA-N",
"smiles": "CC1(C)OB(c2ccc3c(c2)NCCC3)OC1(C)C"
},
"smiles": "CC1(C)OB(c2ccc3c(c2)NCCC3)OC1(C)C",
"reactionStepId": "sa_1db88bd6651bc02050f8cf90",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140005190A1;0332;1468333\",\"rsmi\":\"Br[c:6]1[cH:7][cH:8][c:9]2[c:14]([cH:15]1)[NH:13][CH2:12][CH2:11][CH2:10]2.CC1(C)OB([B:5]2[O:4][C:2]([CH3:1])([CH3:3])[C:17]([CH3:18])([CH3:19])[O:16]2)OC1(C)C>C1COCCO1.CC(=O)O.CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)C2CCCCC2)c(C(C)C)c1.CCOC(C)=O.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.[K+].[Pd].[Pd]>[CH3:1][C:2]1([CH3:3])[O:4][B:5]([c:6]2[cH:7][cH:8][c:9]3[c:14]([cH:15]2)[NH:13][CH2:12][CH2:11][CH2:10]3)[O:16][C:17]1([CH3:18])[CH3:19]\"},\"mapped_reaction_smiles\":\"Br[c:6]1[cH:7][cH:8][c:9]2[c:14]([cH:15]1)[NH:13][CH2:12][CH2:11][CH2:10]2.CC1(C)OB([B:5]2[O:4][C:2]([CH3:1])([CH3:3])[C:17]([CH3:18])([CH3:19])[O:16]2)OC1(C)C>C1COCCO1.CC(=O)O.CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)C2CCCCC2)c(C(C)C)c1.CCOC(C)=O.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.[K+].[Pd].[Pd]>[CH3:1][C:2]1([CH3:3])[O:4][B:5]([c:6]2[cH:7][cH:8][c:9]3[c:14]([cH:15]2)[NH:13][CH2:12][CH2:11][CH2:10]3)[O:16][C:17]1([CH3:18])[CH3:19]\"}",
"reactionStep": {
"id": "sa_1db88bd6651bc02050f8cf90",
"reactionHash": "792a17f0e77a4426bc48cf9cc32348963d2716b7010948edfba4aded0c7f3da0"
},
"children": [
{
"id": "1810",
"routeId": "sa_21260b0433e7515b69add67b",
"moleculeId": "sa_fef5f7b39ff0566393fb775f",
"parentId": "1809",
"isLeaf": true,
"molecule": {
"id": "sa_fef5f7b39ff0566393fb775f",
"inchikey": "DRVWZEWZXCZNAR-UHFFFAOYSA-N",
"smiles": "Brc1ccc2c(c1)NCCC2"
},
"smiles": "Brc1ccc2c(c1)NCCC2",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "1811",
"routeId": "sa_21260b0433e7515b69add67b",
"moleculeId": "sa_e6c301388ac142801d4af5a2",
"parentId": "1809",
"isLeaf": true,
"molecule": {
"id": "sa_e6c301388ac142801d4af5a2",
"inchikey": "IPWKHHSGDUIRAH-UHFFFAOYSA-N",
"smiles": "CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C"
},
"smiles": "CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "1812",
"routeId": "sa_21260b0433e7515b69add67b",
"moleculeId": "sa_88c4bbd2523883294c6aa30a",
"parentId": "1808",
"isLeaf": false,
"molecule": {
"id": "sa_88c4bbd2523883294c6aa30a",
"inchikey": "SXCJQGMKKHRILL-UHFFFAOYSA-N",
"smiles": "COC(=O)c1nc(Br)ccc1OCCOc1ccccc1"
},
"smiles": "COC(=O)c1nc(Br)ccc1OCCOc1ccccc1",
"reactionStepId": "sa_91526bdda63082e5505508fa",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140005190A1;0330;1468332\",\"rsmi\":\"O[CH2:13][CH2:14][O:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1.[CH3:1][O:2][C:3](=[O:4])[c:5]1[n:6][c:7]([Br:8])[cH:9][cH:10][c:11]1[OH:12]>CC(C)OC(=O)/N=N/C(=O)OC(C)C.ClCCl>[CH3:1][O:2][C:3](=[O:4])[c:5]1[n:6][c:7]([Br:8])[cH:9][cH:10][c:11]1[O:12][CH2:13][CH2:14][O:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1\"},\"mapped_reaction_smiles\":\"O[CH2:13][CH2:14][O:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1.[CH3:1][O:2][C:3](=[O:4])[c:5]1[n:6][c:7]([Br:8])[cH:9][cH:10][c:11]1[OH:12]>CC(C)OC(=O)/N=N/C(=O)OC(C)C.ClCCl>[CH3:1][O:2][C:3](=[O:4])[c:5]1[n:6][c:7]([Br:8])[cH:9][cH:10][c:11]1[O:12][CH2:13][CH2:14][O:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1\"}",
"reactionStep": {
"id": "sa_91526bdda63082e5505508fa",
"reactionHash": "c591c5f94c397c9fbd7bbf41027c3bede6e8d727a1f5a113057dcab312008f87"
},
"children": [
{
"id": "1813",
"routeId": "sa_21260b0433e7515b69add67b",
"moleculeId": "sa_7db0aa993bd3edf514be5097",
"parentId": "1812",
"isLeaf": true,
"molecule": {
"id": "sa_7db0aa993bd3edf514be5097",
"inchikey": "QCDWFXQBSFUVSP-UHFFFAOYSA-N",
"smiles": "OCCOc1ccccc1"
},
"smiles": "OCCOc1ccccc1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "1814",
"routeId": "sa_21260b0433e7515b69add67b",
"moleculeId": "sa_441c7e6e4ed19a872c2e58c0",
"parentId": "1812",
"isLeaf": false,
"molecule": {
"id": "sa_441c7e6e4ed19a872c2e58c0",
"inchikey": "UGFPNFKMYRHGBG-UHFFFAOYSA-N",
"smiles": "COC(=O)c1nc(Br)ccc1O"
},
"smiles": "COC(=O)c1nc(Br)ccc1O",
"reactionStepId": "sa_6bc97abd407897d45994c40e",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140005190A1;0319;1468328\",\"rsmi\":\"Br[Br:8].[CH3:1][O:2][C:3](=[O:4])[c:5]1[n:6][cH:7][cH:9][cH:10][c:11]1[OH:12]>O>[CH3:1][O:2][C:3](=[O:4])[c:5]1[n:6][c:7]([Br:8])[cH:9][cH:10][c:11]1[OH:12]\"},\"mapped_reaction_smiles\":\"Br[Br:8].[CH3:1][O:2][C:3](=[O:4])[c:5]1[n:6][cH:7][cH:9][cH:10][c:11]1[OH:12]>O>[CH3:1][O:2][C:3](=[O:4])[c:5]1[n:6][c:7]([Br:8])[cH:9][cH:10][c:11]1[OH:12]\"}",
"reactionStep": {
"id": "sa_6bc97abd407897d45994c40e",
"reactionHash": "edc8d2331e137cef5cb77a6d18e2cc54f0a9917187f08d9b818347831daa6cf4"
},
"children": [
{
"id": "1815",
"routeId": "sa_21260b0433e7515b69add67b",
"moleculeId": "sa_24211e89e565c162ea935f73",
"parentId": "1814",
"isLeaf": true,
"molecule": {
"id": "sa_24211e89e565c162ea935f73",
"inchikey": "GDTBXPJZTBHREO-UHFFFAOYSA-N",
"smiles": "BrBr"
},
"smiles": "BrBr",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "1816",
"routeId": "sa_21260b0433e7515b69add67b",
"moleculeId": "sa_3a4dde98868c528b2f8d8932",
"parentId": "1814",
"isLeaf": false,
"molecule": {
"id": "sa_3a4dde98868c528b2f8d8932",
"inchikey": "MHKKUZDJUGIOBC-UHFFFAOYSA-N",
"smiles": "COC(=O)c1ncccc1O"
},
"smiles": "COC(=O)c1ncccc1O",
"reactionStepId": "sa_3fb14e73cde375993e570217",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140005190A1;0317;1468327\",\"rsmi\":\"O[C:3](=[O:4])[c:5]1[n:6][cH:7][cH:8][cH:9][c:10]1[OH:11].[CH3:1][OH:2]>O=S(=O)(O)O>[CH3:1][O:2][C:3](=[O:4])[c:5]1[n:6][cH:7][cH:8][cH:9][c:10]1[OH:11]\"},\"mapped_reaction_smiles\":\"O[C:3](=[O:4])[c:5]1[n:6][cH:7][cH:8][cH:9][c:10]1[OH:11].[CH3:1][OH:2]>O=S(=O)(O)O>[CH3:1][O:2][C:3](=[O:4])[c:5]1[n:6][cH:7][cH:8][cH:9][c:10]1[OH:11]\"}",
"reactionStep": {
"id": "sa_3fb14e73cde375993e570217",
"reactionHash": "e20416516806245a9cdf135c4e3e295c4fdd8c5baab6c2549bbacfed3a1facd3"
},
"children": [
{
"id": "1817",
"routeId": "sa_21260b0433e7515b69add67b",
"moleculeId": "sa_fec8ec06a10eb7f9024d5e12",
"parentId": "1816",
"isLeaf": true,
"molecule": {
"id": "sa_fec8ec06a10eb7f9024d5e12",
"inchikey": "BRARRAHGNDUELT-UHFFFAOYSA-N",
"smiles": "O=C(O)c1ncccc1O"
},
"smiles": "O=C(O)c1ncccc1O",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "1818",
"routeId": "sa_21260b0433e7515b69add67b",
"moleculeId": "sa_061a3efbe4d30c2cc87d48e7",
"parentId": "1816",
"isLeaf": true,
"molecule": {
"id": "sa_061a3efbe4d30c2cc87d48e7",
"inchikey": "OKKJLVBELUTLKV-UHFFFAOYSA-N",
"smiles": "CO"
},
"smiles": "CO",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
]
}
]
}
}