Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
O=C1NCC2Cc3c(n(Cc4ccc(F)cc4)c4ccccc34)CN12
InChiKey
BYHTURHBYUFPNC-UHFFFAOYSA-N
Route Signature
00e34b73d9471005fd97bcfbe3549e7c08f0f8d20a221efba6df373d827a76cf
Synthesis route with 5 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_c7d211b94224a4f2d5e9e812",
"signature": "00e34b73d9471005fd97bcfbe3549e7c08f0f8d20a221efba6df373d827a76cf",
"contentHash": "7cc4dd0833dc219e9b69681cb9f044f411598a2a7485a60f3dc8b2adc24e6dc3",
"length": 5,
"isConvergent": false
},
"target": {
"id": "sa_f785b87ac62d60f385c7bff1",
"benchmarkSetId": "61e696668b63e77d7c2a29c0821768e1c383de8313852d6e995224859494442e",
"targetId": "n5-00765",
"moleculeId": "sa_7424f6ea7bcbc2a6ca1c48e7",
"smiles": "O=C1NCC2Cc3c(n(Cc4ccc(F)cc4)c4ccccc34)CN12",
"routeLength": 5,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_7424f6ea7bcbc2a6ca1c48e7",
"inchikey": "BYHTURHBYUFPNC-UHFFFAOYSA-N",
"smiles": "O=C1NCC2Cc3c(n(Cc4ccc(F)cc4)c4ccccc34)CN12"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "13771",
"routeId": "sa_c7d211b94224a4f2d5e9e812",
"moleculeId": "sa_7424f6ea7bcbc2a6ca1c48e7",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_7424f6ea7bcbc2a6ca1c48e7",
"inchikey": "BYHTURHBYUFPNC-UHFFFAOYSA-N",
"smiles": "O=C1NCC2Cc3c(n(Cc4ccc(F)cc4)c4ccccc34)CN12"
},
"smiles": "O=C1NCC2Cc3c(n(Cc4ccc(F)cc4)c4ccccc34)CN12",
"reactionStepId": "sa_da7e562a69a58ea667617a90",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160264575A1;0611;1933054\",\"rsmi\":\"[NH2:3][CH2:4][CH:5]1[CH2:6][c:7]2[c:8]([n:11]([CH2:12][c:13]3[cH:14][cH:15][c:16]([F:17])[cH:18][cH:19]3)[c:20]3[c:21]2[cH:22][cH:23][cH:24][cH:25]3)[CH2:9][NH:10]1.c1cn([C:2](n2ccnc2)=[O:1])cn1>C1CCOC1.CCN(CC)CC.O>[O:1]=[C:2]1[NH:3][CH2:4][CH:5]2[CH2:6][c:7]3[c:8]([n:11]([CH2:12][c:13]4[cH:14][cH:15][c:16]([F:17])[cH:18][cH:19]4)[c:20]4[c:21]3[cH:22][cH:23][cH:24][cH:25]4)[CH2:9][N:10]12\"},\"mapped_reaction_smiles\":\"[NH2:3][CH2:4][CH:5]1[CH2:6][c:7]2[c:8]([n:11]([CH2:12][c:13]3[cH:14][cH:15][c:16]([F:17])[cH:18][cH:19]3)[c:20]3[c:21]2[cH:22][cH:23][cH:24][cH:25]3)[CH2:9][NH:10]1.c1cn([C:2](n2ccnc2)=[O:1])cn1>C1CCOC1.CCN(CC)CC.O>[O:1]=[C:2]1[NH:3][CH2:4][CH:5]2[CH2:6][c:7]3[c:8]([n:11]([CH2:12][c:13]4[cH:14][cH:15][c:16]([F:17])[cH:18][cH:19]4)[c:20]4[c:21]3[cH:22][cH:23][cH:24][cH:25]4)[CH2:9][N:10]12\"}",
"reactionStep": {
"id": "sa_da7e562a69a58ea667617a90",
"reactionHash": "cf2e8c915e35472249a2ed30c2a7222c8cd1c77ca45a3478a4d1e9f0caf75208"
},
"children": [
{
"id": "13772",
"routeId": "sa_c7d211b94224a4f2d5e9e812",
"moleculeId": "sa_0b30a91a54f3198f02aa887d",
"parentId": "13771",
"isLeaf": true,
"molecule": {
"id": "sa_0b30a91a54f3198f02aa887d",
"inchikey": "PFKFTWBEEFSNDU-UHFFFAOYSA-N",
"smiles": "O=C(n1ccnc1)n1ccnc1"
},
"smiles": "O=C(n1ccnc1)n1ccnc1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "13773",
"routeId": "sa_c7d211b94224a4f2d5e9e812",
"moleculeId": "sa_f5ae0b914c5aab7f1ff45799",
"parentId": "13771",
"isLeaf": false,
"molecule": {
"id": "sa_f5ae0b914c5aab7f1ff45799",
"inchikey": "YIVCRLRFXWFDQE-UHFFFAOYSA-N",
"smiles": "NCC1Cc2c(n(Cc3ccc(F)cc3)c3ccccc23)CN1"
},
"smiles": "NCC1Cc2c(n(Cc3ccc(F)cc3)c3ccccc23)CN1",
"reactionStepId": "sa_e8cb42e9461e5f9cc6b9dcfd",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160264575A1;0610;1933053\",\"rsmi\":\"CC(C)(C)OC(=O)[N:8]1[CH:3]([CH2:2][NH2:1])[CH2:4][c:5]2[c:6]([n:9]([CH2:10][c:11]3[cH:12][cH:13][c:14]([F:15])[cH:16][cH:17]3)[c:18]3[cH:19][cH:20][cH:21][cH:22][c:23]23)[CH2:7]1>ClCCl.O=C(O)C(F)(F)F>[NH2:1][CH2:2][CH:3]1[CH2:4][c:5]2[c:6]([n:9]([CH2:10][c:11]3[cH:12][cH:13][c:14]([F:15])[cH:16][cH:17]3)[c:18]3[cH:19][cH:20][cH:21][cH:22][c:23]23)[CH2:7][NH:8]1\"},\"mapped_reaction_smiles\":\"CC(C)(C)OC(=O)[N:8]1[CH:3]([CH2:2][NH2:1])[CH2:4][c:5]2[c:6]([n:9]([CH2:10][c:11]3[cH:12][cH:13][c:14]([F:15])[cH:16][cH:17]3)[c:18]3[cH:19][cH:20][cH:21][cH:22][c:23]23)[CH2:7]1>ClCCl.O=C(O)C(F)(F)F>[NH2:1][CH2:2][CH:3]1[CH2:4][c:5]2[c:6]([n:9]([CH2:10][c:11]3[cH:12][cH:13][c:14]([F:15])[cH:16][cH:17]3)[c:18]3[cH:19][cH:20][cH:21][cH:22][c:23]23)[CH2:7][NH:8]1\"}",
"reactionStep": {
"id": "sa_e8cb42e9461e5f9cc6b9dcfd",
"reactionHash": "b24bbbde0a7a012a85c427c59cdd19af9210aa342a7957958f5470b4fe066a6f"
},
"children": [
{
"id": "13774",
"routeId": "sa_c7d211b94224a4f2d5e9e812",
"moleculeId": "sa_03d6a2a7989f2b501dae2223",
"parentId": "13773",
"isLeaf": false,
"molecule": {
"id": "sa_03d6a2a7989f2b501dae2223",
"inchikey": "GAPFWRHVRDYVTL-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)N1Cc2c(c3ccccc3n2Cc2ccc(F)cc2)CC1CN"
},
"smiles": "CC(C)(C)OC(=O)N1Cc2c(c3ccccc3n2Cc2ccc(F)cc2)CC1CN",
"reactionStepId": "sa_becdb716881d5a29179be0df",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160264575A1;0609;1933052\",\"rsmi\":\"O=[C:14]([CH:13]1[N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:9][c:10]2[c:11]([c:16]3[cH:17][cH:18][cH:19][cH:20][c:21]3[n:22]2[CH2:23][c:24]2[cH:25][cH:26][c:27]([F:28])[cH:29][cH:30]2)[CH2:12]1)[NH2:15]>C1CCOC1.CSC>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][c:10]2[c:11]([c:16]3[cH:17][cH:18][cH:19][cH:20][c:21]3[n:22]2[CH2:23][c:24]2[cH:25][cH:26][c:27]([F:28])[cH:29][cH:30]2)[CH2:12][CH:13]1[CH2:14][NH2:15]\"},\"mapped_reaction_smiles\":\"O=[C:14]([CH:13]1[N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:9][c:10]2[c:11]([c:16]3[cH:17][cH:18][cH:19][cH:20][c:21]3[n:22]2[CH2:23][c:24]2[cH:25][cH:26][c:27]([F:28])[cH:29][cH:30]2)[CH2:12]1)[NH2:15]>C1CCOC1.CSC>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][c:10]2[c:11]([c:16]3[cH:17][cH:18][cH:19][cH:20][c:21]3[n:22]2[CH2:23][c:24]2[cH:25][cH:26][c:27]([F:28])[cH:29][cH:30]2)[CH2:12][CH:13]1[CH2:14][NH2:15]\"}",
"reactionStep": {
"id": "sa_becdb716881d5a29179be0df",
"reactionHash": "ebb42a3d81ad496ebe27cffe8f497f36e1fc26e02635444e1b17ef1ee671aab4"
},
"children": [
{
"id": "13775",
"routeId": "sa_c7d211b94224a4f2d5e9e812",
"moleculeId": "sa_41a2e14a7b8933047de81fb3",
"parentId": "13774",
"isLeaf": false,
"molecule": {
"id": "sa_41a2e14a7b8933047de81fb3",
"inchikey": "VDYAVSRLTDLTQZ-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)N1Cc2c(c3ccccc3n2Cc2ccc(F)cc2)CC1C(N)=O"
},
"smiles": "CC(C)(C)OC(=O)N1Cc2c(c3ccccc3n2Cc2ccc(F)cc2)CC1C(N)=O",
"reactionStepId": "sa_15da725269b1002997d2926c",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160264575A1;0608;1933051\",\"rsmi\":\"Br[CH2:24][c:25]1[cH:26][cH:27][c:28]([F:29])[cH:30][cH:31]1.[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][c:10]2[c:11]([c:17]3[cH:18][cH:19][cH:20][cH:21][c:22]3[nH:23]2)[CH2:12][CH:13]1[C:14]([NH2:15])=[O:16]>CCCC[N+](CCCC)(CCCC)CCCC.CN(C)C=O.O.O=C(O)O.Br.[Cs+].[Cs+]>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][c:10]2[c:11]([c:17]3[cH:18][cH:19][cH:20][cH:21][c:22]3[n:23]2[CH2:24][c:25]2[cH:26][cH:27][c:28]([F:29])[cH:30][cH:31]2)[CH2:12][CH:13]1[C:14]([NH2:15])=[O:16]\"},\"mapped_reaction_smiles\":\"Br[CH2:24][c:25]1[cH:26][cH:27][c:28]([F:29])[cH:30][cH:31]1.[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][c:10]2[c:11]([c:17]3[cH:18][cH:19][cH:20][cH:21][c:22]3[nH:23]2)[CH2:12][CH:13]1[C:14]([NH2:15])=[O:16]>CCCC[N+](CCCC)(CCCC)CCCC.CN(C)C=O.O.O=C(O)O.Br.[Cs+].[Cs+]>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][c:10]2[c:11]([c:17]3[cH:18][cH:19][cH:20][cH:21][c:22]3[n:23]2[CH2:24][c:25]2[cH:26][cH:27][c:28]([F:29])[cH:30][cH:31]2)[CH2:12][CH:13]1[C:14]([NH2:15])=[O:16]\"}",
"reactionStep": {
"id": "sa_15da725269b1002997d2926c",
"reactionHash": "51e867732a089728561bc130acb422b15d27d0c0c79d79c27163c05cdb92601c"
},
"children": [
{
"id": "13776",
"routeId": "sa_c7d211b94224a4f2d5e9e812",
"moleculeId": "sa_5f3ba7f73acc20e80a7a1bea",
"parentId": "13775",
"isLeaf": true,
"molecule": {
"id": "sa_5f3ba7f73acc20e80a7a1bea",
"inchikey": "NVNPLEPBDPJYRZ-UHFFFAOYSA-N",
"smiles": "Fc1ccc(CBr)cc1"
},
"smiles": "Fc1ccc(CBr)cc1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "13777",
"routeId": "sa_c7d211b94224a4f2d5e9e812",
"moleculeId": "sa_6fffcce6f7f7374783a93647",
"parentId": "13775",
"isLeaf": false,
"molecule": {
"id": "sa_6fffcce6f7f7374783a93647",
"inchikey": "TXPGCBBAIAVRKN-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)N1Cc2[nH]c3ccccc3c2CC1C(N)=O"
},
"smiles": "CC(C)(C)OC(=O)N1Cc2[nH]c3ccccc3c2CC1C(N)=O",
"reactionStepId": "sa_8a99ac6a93fdb371a9bcdb8d",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160264575A1;0607;1933050\",\"rsmi\":\"O[C:14]([CH:13]1[N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:9][c:10]2[c:11]([c:17]3[cH:18][cH:19][cH:20][cH:21][c:22]3[nH:23]2)[CH2:12]1)=[O:16].[NH3:15]>CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C.Cl.ClCCl.O.On1nnc2ccccc21.Cl>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][c:10]2[c:11]([c:17]3[cH:18][cH:19][cH:20][cH:21][c:22]3[nH:23]2)[CH2:12][CH:13]1[C:14]([NH2:15])=[O:16]\"},\"mapped_reaction_smiles\":\"O[C:14]([CH:13]1[N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:9][c:10]2[c:11]([c:17]3[cH:18][cH:19][cH:20][cH:21][c:22]3[nH:23]2)[CH2:12]1)=[O:16].[NH3:15]>CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C.Cl.ClCCl.O.On1nnc2ccccc21.Cl>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][c:10]2[c:11]([c:17]3[cH:18][cH:19][cH:20][cH:21][c:22]3[nH:23]2)[CH2:12][CH:13]1[C:14]([NH2:15])=[O:16]\"}",
"reactionStep": {
"id": "sa_8a99ac6a93fdb371a9bcdb8d",
"reactionHash": "34a057d2d7ff4d33601e49ed4606e120777855bc32ee269acf0ae38a4423be23"
},
"children": [
{
"id": "13778",
"routeId": "sa_c7d211b94224a4f2d5e9e812",
"moleculeId": "sa_59dec821175e182e0c0b95ac",
"parentId": "13777",
"isLeaf": true,
"molecule": {
"id": "sa_59dec821175e182e0c0b95ac",
"inchikey": "FHEPEWKHTOVVAT-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)N1Cc2[nH]c3ccccc3c2CC1C(=O)O"
},
"smiles": "CC(C)(C)OC(=O)N1Cc2[nH]c3ccccc3c2CC1C(=O)O",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "13779",
"routeId": "sa_c7d211b94224a4f2d5e9e812",
"moleculeId": "sa_c9679fdd876f32f86b77fb69",
"parentId": "13777",
"isLeaf": true,
"molecule": {
"id": "sa_c9679fdd876f32f86b77fb69",
"inchikey": "QGZKDVFQNNGYKY-UHFFFAOYSA-N",
"smiles": "N"
},
"smiles": "N",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
]
}
]
}
]
}
}