Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
O=C(NCc1cccnc1)Nc1ccc(-c2nn(CCN3CCCCC3)c3ccccc23)cc1
InChiKey
BVGWAWMZKDBHHX-UHFFFAOYSA-N
Route Signature
863adcac8e633a3f7fa23fee8ef2168d00baf4d15ed5ff144697247107e54070
Synthesis route with 3 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_8701f590735f307217f4ec5c",
"signature": "863adcac8e633a3f7fa23fee8ef2168d00baf4d15ed5ff144697247107e54070",
"contentHash": "3db92671742631abaa15422d01f115c7d83c359f3d7ea4f3109d8a5ad93ca88e",
"length": 3,
"isConvergent": true
},
"target": {
"id": "sa_06d762833cc417e5a4e9c4da",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-02509",
"moleculeId": "sa_0eb4429382f3640e70c2cca1",
"smiles": "O=C(NCc1cccnc1)Nc1ccc(-c2nn(CCN3CCCCC3)c3ccccc23)cc1",
"routeLength": 3,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_0eb4429382f3640e70c2cca1",
"inchikey": "BVGWAWMZKDBHHX-UHFFFAOYSA-N",
"smiles": "O=C(NCc1cccnc1)Nc1ccc(-c2nn(CCN3CCCCC3)c3ccccc23)cc1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "10761",
"routeId": "sa_8701f590735f307217f4ec5c",
"moleculeId": "sa_0eb4429382f3640e70c2cca1",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_0eb4429382f3640e70c2cca1",
"inchikey": "BVGWAWMZKDBHHX-UHFFFAOYSA-N",
"smiles": "O=C(NCc1cccnc1)Nc1ccc(-c2nn(CCN3CCCCC3)c3ccccc23)cc1"
},
"smiles": "O=C(NCc1cccnc1)Nc1ccc(-c2nn(CCN3CCCCC3)c3ccccc23)cc1",
"reactionStepId": "sa_3a1d402e413b383fe5df702b",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140349989A1;0400;1619464\",\"rsmi\":\"CC1(C)OB([c:15]2[cH:14][cH:13][c:12]([NH:11][C:2](=[O:1])[NH:3][CH2:4][c:5]3[cH:6][cH:7][cH:8][n:9][cH:10]3)[cH:34][cH:33]2)OC1(C)C.I[c:16]1[n:17][n:18]([CH2:19][CH2:20][N:21]2[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]2)[c:27]2[cH:28][cH:29][cH:30][cH:31][c:32]12>CCO.COCCOC.O=C(O)O.[Na+].[Pd].c1ccc(P(c2ccccc2)c2ccccc2)cc1.c1ccc(P(c2ccccc2)c2ccccc2)cc1.c1ccc(P(c2ccccc2)c2ccccc2)cc1.c1ccc(P(c2ccccc2)c2ccccc2)cc1>[O:1]=[C:2]([NH:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][n:9][cH:10]1)[NH:11][c:12]1[cH:13][cH:14][c:15](-[c:16]2[n:17][n:18]([CH2:19][CH2:20][N:21]3[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]3)[c:27]3[cH:28][cH:29][cH:30][cH:31][c:32]23)[cH:33][cH:34]1\"},\"mapped_reaction_smiles\":\"CC1(C)OB([c:15]2[cH:14][cH:13][c:12]([NH:11][C:2](=[O:1])[NH:3][CH2:4][c:5]3[cH:6][cH:7][cH:8][n:9][cH:10]3)[cH:34][cH:33]2)OC1(C)C.I[c:16]1[n:17][n:18]([CH2:19][CH2:20][N:21]2[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]2)[c:27]2[cH:28][cH:29][cH:30][cH:31][c:32]12>CCO.COCCOC.O=C(O)O.[Na+].[Pd].c1ccc(P(c2ccccc2)c2ccccc2)cc1.c1ccc(P(c2ccccc2)c2ccccc2)cc1.c1ccc(P(c2ccccc2)c2ccccc2)cc1.c1ccc(P(c2ccccc2)c2ccccc2)cc1>[O:1]=[C:2]([NH:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][n:9][cH:10]1)[NH:11][c:12]1[cH:13][cH:14][c:15](-[c:16]2[n:17][n:18]([CH2:19][CH2:20][N:21]3[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]3)[c:27]3[cH:28][cH:29][cH:30][cH:31][c:32]23)[cH:33][cH:34]1\"}",
"reactionStep": {
"id": "sa_3a1d402e413b383fe5df702b",
"reactionHash": "f20c2486d25cf1edb51a5799adaad4779922f61edf137c66740d33a3c44b7755"
},
"children": [
{
"id": "10762",
"routeId": "sa_8701f590735f307217f4ec5c",
"moleculeId": "sa_13238384392b2e5ebe67edd8",
"parentId": "10761",
"isLeaf": false,
"molecule": {
"id": "sa_13238384392b2e5ebe67edd8",
"inchikey": "NXPDFQGHEPOHIF-UHFFFAOYSA-N",
"smiles": "Ic1nn(CCN2CCCCC2)c2ccccc12"
},
"smiles": "Ic1nn(CCN2CCCCC2)c2ccccc12",
"reactionStepId": "sa_3867ac7a6c0b5e87e9e3fc10",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140349989A1;0399;1619463\",\"rsmi\":\"Cl[CH2:5][CH2:6][N:7]1[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]1.[I:1][c:2]1[n:3][nH:4][c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]12>CN(C)C=O.Cl.O.[HH].[Na+]>[I:1][c:2]1[n:3][n:4]([CH2:5][CH2:6][N:7]2[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]2)[c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]12\"},\"mapped_reaction_smiles\":\"Cl[CH2:5][CH2:6][N:7]1[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]1.[I:1][c:2]1[n:3][nH:4][c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]12>CN(C)C=O.Cl.O.[HH].[Na+]>[I:1][c:2]1[n:3][n:4]([CH2:5][CH2:6][N:7]2[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]2)[c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]12\"}",
"reactionStep": {
"id": "sa_3867ac7a6c0b5e87e9e3fc10",
"reactionHash": "0784efa415d5205156a0aa9e2f0d64225d1eaa1b2fc409fb2265e95801401edc"
},
"children": [
{
"id": "10763",
"routeId": "sa_8701f590735f307217f4ec5c",
"moleculeId": "sa_4af7ca3657fe88f1bd287023",
"parentId": "10762",
"isLeaf": false,
"molecule": {
"id": "sa_4af7ca3657fe88f1bd287023",
"inchikey": "UDKYMMQGPNFWDA-UHFFFAOYSA-N",
"smiles": "Ic1n[nH]c2ccccc12"
},
"smiles": "Ic1n[nH]c2ccccc12",
"reactionStepId": "sa_fb4f5bc266274c492bcf440b",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140349989A1;0398;1619462\",\"rsmi\":\"I[I:1].[cH:2]1[n:3][nH:4][c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]12>CN(C)C=O.O.O=C(O)O.O=S(O)(O)=S.[K+].[K+].[Na+].[Na+]>[I:1][c:2]1[n:3][nH:4][c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]12\"},\"mapped_reaction_smiles\":\"I[I:1].[cH:2]1[n:3][nH:4][c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]12>CN(C)C=O.O.O=C(O)O.O=S(O)(O)=S.[K+].[K+].[Na+].[Na+]>[I:1][c:2]1[n:3][nH:4][c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]12\"}",
"reactionStep": {
"id": "sa_fb4f5bc266274c492bcf440b",
"reactionHash": "1b3f0439a99589d428f01503c1c18ed300d1073bdc7c2597dcecd1877d042d28"
},
"children": [
{
"id": "10764",
"routeId": "sa_8701f590735f307217f4ec5c",
"moleculeId": "sa_6feedd9b166cdb4bb039354f",
"parentId": "10763",
"isLeaf": true,
"molecule": {
"id": "sa_6feedd9b166cdb4bb039354f",
"inchikey": "BAXOFTOLAUCFNW-UHFFFAOYSA-N",
"smiles": "c1ccc2n[nH]cc2c1"
},
"smiles": "c1ccc2[nH]ncc2c1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "10765",
"routeId": "sa_8701f590735f307217f4ec5c",
"moleculeId": "sa_bc6c113460696c6012e3bdf5",
"parentId": "10763",
"isLeaf": true,
"molecule": {
"id": "sa_bc6c113460696c6012e3bdf5",
"inchikey": "PNDPGZBMCMUPRI-UHFFFAOYSA-N",
"smiles": "II"
},
"smiles": "II",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "10766",
"routeId": "sa_8701f590735f307217f4ec5c",
"moleculeId": "sa_d337465eb6918a123669c79d",
"parentId": "10762",
"isLeaf": true,
"molecule": {
"id": "sa_d337465eb6918a123669c79d",
"inchikey": "WNRWEBKEQARBKV-UHFFFAOYSA-N",
"smiles": "ClCCN1CCCCC1"
},
"smiles": "ClCCN1CCCCC1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "10767",
"routeId": "sa_8701f590735f307217f4ec5c",
"moleculeId": "sa_8fbe1bbf9e666330e2ddf885",
"parentId": "10761",
"isLeaf": false,
"molecule": {
"id": "sa_8fbe1bbf9e666330e2ddf885",
"inchikey": "SZCVHKGAAOZQJC-UHFFFAOYSA-N",
"smiles": "CC1(C)OB(c2ccc(NC(=O)NCc3cccnc3)cc2)OC1(C)C"
},
"smiles": "CC1(C)OB(c2ccc(NC(=O)NCc3cccnc3)cc2)OC1(C)C",
"reactionStepId": "sa_4718d92137c098f7d17a77b0",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140349989A1;0397;1619461\",\"rsmi\":\"ClC(Cl)(Cl)O[C:11](Cl)=[O:12].[CH3:1][C:2]1([CH3:3])[O:4][B:5]([c:6]2[cH:7][cH:8][c:9]([NH2:10])[cH:21][cH:22]2)[O:23][C:24]1([CH3:25])[CH3:26].[NH2:13][CH2:14][c:15]1[cH:16][cH:17][cH:18][n:19][cH:20]1>CCN(CC)CC.ClCCl>[CH3:1][C:2]1([CH3:3])[O:4][B:5]([c:6]2[cH:7][cH:8][c:9]([NH:10][C:11](=[O:12])[NH:13][CH2:14][c:15]3[cH:16][cH:17][cH:18][n:19][cH:20]3)[cH:21][cH:22]2)[O:23][C:24]1([CH3:25])[CH3:26]\"},\"mapped_reaction_smiles\":\"ClC(Cl)(Cl)O[C:11](Cl)=[O:12].[CH3:1][C:2]1([CH3:3])[O:4][B:5]([c:6]2[cH:7][cH:8][c:9]([NH2:10])[cH:21][cH:22]2)[O:23][C:24]1([CH3:25])[CH3:26].[NH2:13][CH2:14][c:15]1[cH:16][cH:17][cH:18][n:19][cH:20]1>CCN(CC)CC.ClCCl>[CH3:1][C:2]1([CH3:3])[O:4][B:5]([c:6]2[cH:7][cH:8][c:9]([NH:10][C:11](=[O:12])[NH:13][CH2:14][c:15]3[cH:16][cH:17][cH:18][n:19][cH:20]3)[cH:21][cH:22]2)[O:23][C:24]1([CH3:25])[CH3:26]\"}",
"reactionStep": {
"id": "sa_4718d92137c098f7d17a77b0",
"reactionHash": "b5914f458aa7e81e4d5e2b149b427be0f4474ca011dbaa937697c734de6869f2"
},
"children": [
{
"id": "10768",
"routeId": "sa_8701f590735f307217f4ec5c",
"moleculeId": "sa_ac7e6a17010a02e062566c0e",
"parentId": "10767",
"isLeaf": true,
"molecule": {
"id": "sa_ac7e6a17010a02e062566c0e",
"inchikey": "HCUYBXPSSCRKRF-UHFFFAOYSA-N",
"smiles": "O=C(Cl)OC(Cl)(Cl)Cl"
},
"smiles": "O=C(Cl)OC(Cl)(Cl)Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "10769",
"routeId": "sa_8701f590735f307217f4ec5c",
"moleculeId": "sa_c1440b0d138975d9344b556d",
"parentId": "10767",
"isLeaf": true,
"molecule": {
"id": "sa_c1440b0d138975d9344b556d",
"inchikey": "HDOUGSFASVGDCS-UHFFFAOYSA-N",
"smiles": "NCc1cccnc1"
},
"smiles": "NCc1cccnc1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "10770",
"routeId": "sa_8701f590735f307217f4ec5c",
"moleculeId": "sa_9389f810c153d36cc08eba6b",
"parentId": "10767",
"isLeaf": true,
"molecule": {
"id": "sa_9389f810c153d36cc08eba6b",
"inchikey": "ZANPJXNYBVVNSD-UHFFFAOYSA-N",
"smiles": "CC1(C)OB(c2ccc(N)cc2)OC1(C)C"
},
"smiles": "CC1(C)OB(c2ccc(N)cc2)OC1(C)C",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
}