Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CN1CCN(C(=O)CCNC(=O)c2cc(-c3ccc(F)cc3)on2)CC1
InChiKey
BNHSFGDXBTZXKM-UHFFFAOYSA-N
Route Signature
ca138e685a4600dc40ca2d429cb3db35d8c8b5390bf3115787944b030365617a
Synthesis route with 6 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_73dbf429b384d4cb528df4c5",
"signature": "ca138e685a4600dc40ca2d429cb3db35d8c8b5390bf3115787944b030365617a",
"contentHash": "c3e3a250cb603d08c543dfc897d4c0f97829ff9d99bf5958a3cbc1e6b58dc7ef",
"length": 6,
"isConvergent": false
},
"target": {
"id": "sa_1d0e46f7020fa4cc4720ceba",
"benchmarkSetId": "f925e688d731a0ad4e3aa6a505df094f6d3ca64ce3facc312bc5f64731921b33",
"targetId": "n5-00643",
"moleculeId": "sa_42ca07665a60e01dbe19a009",
"smiles": "CN1CCN(C(=O)CCNC(=O)c2cc(-c3ccc(F)cc3)on2)CC1",
"routeLength": 6,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_42ca07665a60e01dbe19a009",
"inchikey": "BNHSFGDXBTZXKM-UHFFFAOYSA-N",
"smiles": "CN1CCN(C(=O)CCNC(=O)c2cc(-c3ccc(F)cc3)on2)CC1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 4
},
"rootNode": {
"id": "4618",
"routeId": "sa_73dbf429b384d4cb528df4c5",
"moleculeId": "sa_42ca07665a60e01dbe19a009",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_42ca07665a60e01dbe19a009",
"inchikey": "BNHSFGDXBTZXKM-UHFFFAOYSA-N",
"smiles": "CN1CCN(C(=O)CCNC(=O)c2cc(-c3ccc(F)cc3)on2)CC1"
},
"smiles": "CN1CCN(C(=O)CCNC(=O)c2cc(-c3ccc(F)cc3)on2)CC1",
"reactionStepId": "sa_c17383b212ab88d43ce108f3",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160128984A1;0134;1873730\",\"rsmi\":\"O[C:6](=[O:7])[CH2:8][CH2:9][NH:10][C:11](=[O:12])[c:13]1[n:14][o:15][c:16](-[c:17]2[cH:18][cH:19][c:20]([F:21])[cH:22][cH:23]2)[cH:24]1.[CH3:1][N:2]1[CH2:3][CH2:4][NH:5][CH2:25][CH2:26]1>CCN(C(C)C)C(C)C.CN(C)C(On1nnc2cccnc21)=[N+](C)C.CN(C)C=O.F[PH](F)(F)(F)(F)F>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:6](=[O:7])[CH2:8][CH2:9][NH:10][C:11](=[O:12])[c:13]2[n:14][o:15][c:16](-[c:17]3[cH:18][cH:19][c:20]([F:21])[cH:22][cH:23]3)[cH:24]2)[CH2:25][CH2:26]1\"},\"mapped_reaction_smiles\":\"O[C:6](=[O:7])[CH2:8][CH2:9][NH:10][C:11](=[O:12])[c:13]1[n:14][o:15][c:16](-[c:17]2[cH:18][cH:19][c:20]([F:21])[cH:22][cH:23]2)[cH:24]1.[CH3:1][N:2]1[CH2:3][CH2:4][NH:5][CH2:25][CH2:26]1>CCN(C(C)C)C(C)C.CN(C)C(On1nnc2cccnc21)=[N+](C)C.CN(C)C=O.F[PH](F)(F)(F)(F)F>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:6](=[O:7])[CH2:8][CH2:9][NH:10][C:11](=[O:12])[c:13]2[n:14][o:15][c:16](-[c:17]3[cH:18][cH:19][c:20]([F:21])[cH:22][cH:23]3)[cH:24]2)[CH2:25][CH2:26]1\"}",
"reactionStep": {
"id": "sa_c17383b212ab88d43ce108f3",
"reactionHash": "ac76a7dee775994e069fa1f3e39ffd39dfb57386f5defd57f9c85939d41687fb"
},
"children": [
{
"id": "4619",
"routeId": "sa_73dbf429b384d4cb528df4c5",
"moleculeId": "sa_f43bb26611d88fb82b2b3414",
"parentId": "4618",
"isLeaf": false,
"molecule": {
"id": "sa_f43bb26611d88fb82b2b3414",
"inchikey": "FDGNOMXBMSBTCT-UHFFFAOYSA-N",
"smiles": "O=C(O)CCNC(=O)c1cc(-c2ccc(F)cc2)on1"
},
"smiles": "O=C(O)CCNC(=O)c1cc(-c2ccc(F)cc2)on1",
"reactionStepId": "sa_25ab9c227a0e43b944905fd7",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160128984A1;0133;1873729\",\"rsmi\":\"C[O:3][C:2](=[O:1])[CH2:4][CH2:5][NH:6][C:7](=[O:8])[c:9]1[n:10][o:11][c:12](-[c:13]2[cH:14][cH:15][c:16]([F:17])[cH:18][cH:19]2)[cH:20]1>C1CCOC1.O.[Li+].O>[O:1]=[C:2]([OH:3])[CH2:4][CH2:5][NH:6][C:7](=[O:8])[c:9]1[n:10][o:11][c:12](-[c:13]2[cH:14][cH:15][c:16]([F:17])[cH:18][cH:19]2)[cH:20]1\"},\"mapped_reaction_smiles\":\"C[O:3][C:2](=[O:1])[CH2:4][CH2:5][NH:6][C:7](=[O:8])[c:9]1[n:10][o:11][c:12](-[c:13]2[cH:14][cH:15][c:16]([F:17])[cH:18][cH:19]2)[cH:20]1>C1CCOC1.O.[Li+].O>[O:1]=[C:2]([OH:3])[CH2:4][CH2:5][NH:6][C:7](=[O:8])[c:9]1[n:10][o:11][c:12](-[c:13]2[cH:14][cH:15][c:16]([F:17])[cH:18][cH:19]2)[cH:20]1\"}",
"reactionStep": {
"id": "sa_25ab9c227a0e43b944905fd7",
"reactionHash": "6256ba43497cf890fca474cff254d39beb7b650b7f17c5dd8072e009acd2062f"
},
"children": [
{
"id": "4620",
"routeId": "sa_73dbf429b384d4cb528df4c5",
"moleculeId": "sa_7a4c4f407855ecb8b9cd3a40",
"parentId": "4619",
"isLeaf": false,
"molecule": {
"id": "sa_7a4c4f407855ecb8b9cd3a40",
"inchikey": "XBLYPJUPIFQGBK-UHFFFAOYSA-N",
"smiles": "COC(=O)CCNC(=O)c1cc(-c2ccc(F)cc2)on1"
},
"smiles": "COC(=O)CCNC(=O)c1cc(-c2ccc(F)cc2)on1",
"reactionStepId": "sa_4a5100b6ffbd2754d539a77c",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160128984A1;0132;1873728\",\"rsmi\":\"O[C:8](=[O:9])[c:10]1[n:11][o:12][c:13](-[c:14]2[cH:15][cH:16][c:17]([F:18])[cH:19][cH:20]2)[cH:21]1.[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][NH2:7]>CCN(C(C)C)C(C)C.CN(C)C(On1nnc2cccnc21)=[N+](C)C.CN(C)C=O.Cl.F[PH](F)(F)(F)(F)F>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][NH:7][C:8](=[O:9])[c:10]1[n:11][o:12][c:13](-[c:14]2[cH:15][cH:16][c:17]([F:18])[cH:19][cH:20]2)[cH:21]1\"},\"mapped_reaction_smiles\":\"O[C:8](=[O:9])[c:10]1[n:11][o:12][c:13](-[c:14]2[cH:15][cH:16][c:17]([F:18])[cH:19][cH:20]2)[cH:21]1.[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][NH2:7]>CCN(C(C)C)C(C)C.CN(C)C(On1nnc2cccnc21)=[N+](C)C.CN(C)C=O.Cl.F[PH](F)(F)(F)(F)F>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][NH:7][C:8](=[O:9])[c:10]1[n:11][o:12][c:13](-[c:14]2[cH:15][cH:16][c:17]([F:18])[cH:19][cH:20]2)[cH:21]1\"}",
"reactionStep": {
"id": "sa_4a5100b6ffbd2754d539a77c",
"reactionHash": "adef6b44438a0c1a798ba15033b7856d123331129550ce73afa35cba79422308"
},
"children": [
{
"id": "4621",
"routeId": "sa_73dbf429b384d4cb528df4c5",
"moleculeId": "sa_ed75348545b60ecddc4500a1",
"parentId": "4620",
"isLeaf": false,
"molecule": {
"id": "sa_ed75348545b60ecddc4500a1",
"inchikey": "OFWUBERMKPVMCT-UHFFFAOYSA-N",
"smiles": "O=C(O)c1cc(-c2ccc(F)cc2)on1"
},
"smiles": "O=C(O)c1cc(-c2ccc(F)cc2)on1",
"reactionStepId": "sa_a552d6e10db8ad6bc8800cda",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160128984A1;0131;1873727\",\"rsmi\":\"CC[O:3][C:2](=[O:1])[c:4]1[n:5][o:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([F:12])[cH:13][cH:14]2)[cH:15]1>C1CCOC1.O.[Li+].O>[O:1]=[C:2]([OH:3])[c:4]1[n:5][o:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([F:12])[cH:13][cH:14]2)[cH:15]1\"},\"mapped_reaction_smiles\":\"CC[O:3][C:2](=[O:1])[c:4]1[n:5][o:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([F:12])[cH:13][cH:14]2)[cH:15]1>C1CCOC1.O.[Li+].O>[O:1]=[C:2]([OH:3])[c:4]1[n:5][o:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([F:12])[cH:13][cH:14]2)[cH:15]1\"}",
"reactionStep": {
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"reactionHash": "baf0f242ee30bcd7fd9ce85a52880473c949bc2e4ed11def6cf452129e5fc77a"
},
"children": [
{
"id": "4622",
"routeId": "sa_73dbf429b384d4cb528df4c5",
"moleculeId": "sa_8d3040681f57656071e1e843",
"parentId": "4621",
"isLeaf": false,
"molecule": {
"id": "sa_8d3040681f57656071e1e843",
"inchikey": "IYDBYHCVVNAFSM-UHFFFAOYSA-N",
"smiles": "CCOC(=O)c1cc(-c2ccc(F)cc2)on1"
},
"smiles": "CCOC(=O)c1cc(-c2ccc(F)cc2)on1",
"reactionStepId": "sa_d291dc506a5ae9e317ac090c",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160128984A1;0130;1873726\",\"rsmi\":\"O=[C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:17][C:9](=O)[c:10]1[cH:11][cH:12][c:13]([F:14])[cH:15][cH:16]1.[NH2:7][OH:8]>CCO.Cl>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[n:7][o:8][c:9](-[c:10]2[cH:11][cH:12][c:13]([F:14])[cH:15][cH:16]2)[cH:17]1\"},\"mapped_reaction_smiles\":\"O=[C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:17][C:9](=O)[c:10]1[cH:11][cH:12][c:13]([F:14])[cH:15][cH:16]1.[NH2:7][OH:8]>CCO.Cl>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[n:7][o:8][c:9](-[c:10]2[cH:11][cH:12][c:13]([F:14])[cH:15][cH:16]2)[cH:17]1\"}",
"reactionStep": {
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"reactionHash": "a0cc944430efe933c88b2dabec3865f66098d17eee8e2fbfc61bdfaf5be24b31"
},
"children": [
{
"id": "4623",
"routeId": "sa_73dbf429b384d4cb528df4c5",
"moleculeId": "sa_04a18e3f07bde82ca29399ee",
"parentId": "4622",
"isLeaf": true,
"molecule": {
"id": "sa_04a18e3f07bde82ca29399ee",
"inchikey": "AVXURJPOCDRRFD-UHFFFAOYSA-N",
"smiles": "NO"
},
"smiles": "NO",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "4624",
"routeId": "sa_73dbf429b384d4cb528df4c5",
"moleculeId": "sa_8fd8b8a1178d880b8df486d2",
"parentId": "4622",
"isLeaf": false,
"molecule": {
"id": "sa_8fd8b8a1178d880b8df486d2",
"inchikey": "LVLZSYCLOPEBSR-UHFFFAOYSA-N",
"smiles": "CCOC(=O)C(=O)CC(=O)c1ccc(F)cc1"
},
"smiles": "CCOC(=O)C(=O)CC(=O)c1ccc(F)cc1",
"reactionStepId": "sa_dd0a23c36b3a7e438d4d3a64",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160128984A1;0129;1873725\",\"rsmi\":\"CCO[C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])=[O:7].[CH3:8][C:9](=[O:10])[c:11]1[cH:12][cH:13][c:14]([F:15])[cH:16][cH:17]1>Cc1ccccc1.O.[HH].[Na+]>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6](=[O:7])[CH2:8][C:9](=[O:10])[c:11]1[cH:12][cH:13][c:14]([F:15])[cH:16][cH:17]1\"},\"mapped_reaction_smiles\":\"CCO[C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])=[O:7].[CH3:8][C:9](=[O:10])[c:11]1[cH:12][cH:13][c:14]([F:15])[cH:16][cH:17]1>Cc1ccccc1.O.[HH].[Na+]>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6](=[O:7])[CH2:8][C:9](=[O:10])[c:11]1[cH:12][cH:13][c:14]([F:15])[cH:16][cH:17]1\"}",
"reactionStep": {
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"reactionHash": "26e075742a1f2e1904b8182835d1dfee5d1ea324cb7a17bdb964ddb50374e3f0"
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"children": [
{
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"routeId": "sa_73dbf429b384d4cb528df4c5",
"moleculeId": "sa_ab0a3cf4ca71164a04c8f94b",
"parentId": "4624",
"isLeaf": true,
"molecule": {
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"inchikey": "WYACBZDAHNBPPB-UHFFFAOYSA-N",
"smiles": "CCOC(=O)C(=O)OCC"
},
"smiles": "CCOC(=O)C(=O)OCC",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "4626",
"routeId": "sa_73dbf429b384d4cb528df4c5",
"moleculeId": "sa_44c27d53a6e6012f073486d9",
"parentId": "4624",
"isLeaf": true,
"molecule": {
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"inchikey": "ZDPAWHACYDRYIW-UHFFFAOYSA-N",
"smiles": "CC(=O)c1ccc(F)cc1"
},
"smiles": "CC(=O)c1ccc(F)cc1",
"reactionStepId": null,
"template": null,
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}
]
}
]
}
]
},
{
"id": "4627",
"routeId": "sa_73dbf429b384d4cb528df4c5",
"moleculeId": "sa_90adaa5fe4d82e870c9ddc98",
"parentId": "4620",
"isLeaf": true,
"molecule": {
"id": "sa_90adaa5fe4d82e870c9ddc98",
"inchikey": "UZCXPYDBYUEZCV-UHFFFAOYSA-N",
"smiles": "COC(=O)CCN"
},
"smiles": "COC(=O)CCN",
"reactionStepId": null,
"template": null,
"metadata": null,
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"children": []
}
]
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]
},
{
"id": "4628",
"routeId": "sa_73dbf429b384d4cb528df4c5",
"moleculeId": "sa_513cbf1b8d13aff0b62eb838",
"parentId": "4618",
"isLeaf": true,
"molecule": {
"id": "sa_513cbf1b8d13aff0b62eb838",
"inchikey": "PVOAHINGSUIXLS-UHFFFAOYSA-N",
"smiles": "CN1CCNCC1"
},
"smiles": "CN1CCNCC1",
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"template": null,
"metadata": null,
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"children": []
}
]
}
}