Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
Cc1cnc(O)c(-c2nc(NC(=O)C3(c4ccc5c(c4)OC(F)(F)O5)CC3)ccc2C)c1
InChiKey
SXCVDCSPSCUUIL-UHFFFAOYSA-N
Route Signature
0e0a6ec52564492cc65dec4be3810658a6d01e279bec9d3b3c9b1b265cb7fde1
Synthesis route with 4 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_163c5e1b0738c45f42c5a73b",
"signature": "0e0a6ec52564492cc65dec4be3810658a6d01e279bec9d3b3c9b1b265cb7fde1",
"contentHash": "628372cd8f7312713647f809fa6f6b69f680db1647ad628b8b1d33c7913de597",
"length": 4,
"isConvergent": true
},
"target": {
"id": "sa_cb21954e0fe31943d9a5b687",
"benchmarkSetId": "7390a9c2522b1c81605e80a42a8de7c7ad9a5797d028633b54904bc78f091bb8",
"targetId": "n5-00692",
"moleculeId": "sa_4819fcfe6576c56bc864858e",
"smiles": "Cc1cnc(O)c(-c2nc(NC(=O)C3(c4ccc5c(c4)OC(F)(F)O5)CC3)ccc2C)c1",
"routeLength": 4,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_4819fcfe6576c56bc864858e",
"inchikey": "SXCVDCSPSCUUIL-UHFFFAOYSA-N",
"smiles": "Cc1cnc(O)c(-c2nc(NC(=O)C3(c4ccc5c(c4)OC(F)(F)O5)CC3)ccc2C)c1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 6
},
"rootNode": {
"id": "1042",
"routeId": "sa_163c5e1b0738c45f42c5a73b",
"moleculeId": "sa_4819fcfe6576c56bc864858e",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_4819fcfe6576c56bc864858e",
"inchikey": "SXCVDCSPSCUUIL-UHFFFAOYSA-N",
"smiles": "Cc1cnc(O)c(-c2nc(NC(=O)C3(c4ccc5c(c4)OC(F)(F)O5)CC3)ccc2C)c1"
},
"smiles": "Cc1cnc(O)c(-c2nc(NC(=O)C3(c4ccc5c(c4)OC(F)(F)O5)CC3)ccc2C)c1",
"reactionStepId": "sa_75df8b60cdc9c4806dc491c8",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150166516A1;0525;1705734\",\"rsmi\":\"C[O:6][c:5]1[n:4][cH:3][c:2]([CH3:1])[cH:32][c:7]1-[c:8]1[n:9][c:10]([NH:11][C:12](=[O:13])[C:14]2([c:15]3[cH:16][c:17]4[c:18]([cH:19][cH:20]3)[O:21][C:22]([F:23])([F:24])[O:25]4)[CH2:26][CH2:27]2)[cH:28][cH:29][c:30]1[CH3:31]>CC#N.CCOC(C)=O.C[Si](C)(C)I.ClCCl>[CH3:1][c:2]1[cH:3][n:4][c:5]([OH:6])[c:7](-[c:8]2[n:9][c:10]([NH:11][C:12](=[O:13])[C:14]3([c:15]4[cH:16][c:17]5[c:18]([cH:19][cH:20]4)[O:21][C:22]([F:23])([F:24])[O:25]5)[CH2:26][CH2:27]3)[cH:28][cH:29][c:30]2[CH3:31])[cH:32]1\"},\"mapped_reaction_smiles\":\"C[O:6][c:5]1[n:4][cH:3][c:2]([CH3:1])[cH:32][c:7]1-[c:8]1[n:9][c:10]([NH:11][C:12](=[O:13])[C:14]2([c:15]3[cH:16][c:17]4[c:18]([cH:19][cH:20]3)[O:21][C:22]([F:23])([F:24])[O:25]4)[CH2:26][CH2:27]2)[cH:28][cH:29][c:30]1[CH3:31]>CC#N.CCOC(C)=O.C[Si](C)(C)I.ClCCl>[CH3:1][c:2]1[cH:3][n:4][c:5]([OH:6])[c:7](-[c:8]2[n:9][c:10]([NH:11][C:12](=[O:13])[C:14]3([c:15]4[cH:16][c:17]5[c:18]([cH:19][cH:20]4)[O:21][C:22]([F:23])([F:24])[O:25]5)[CH2:26][CH2:27]3)[cH:28][cH:29][c:30]2[CH3:31])[cH:32]1\"}",
"reactionStep": {
"id": "sa_75df8b60cdc9c4806dc491c8",
"reactionHash": "b843134d79d6f5581e1565841cb3f4205c00f6b97c178e77d2d217d046817fe2"
},
"children": [
{
"id": "1043",
"routeId": "sa_163c5e1b0738c45f42c5a73b",
"moleculeId": "sa_25ef12f2fdc69dfd611ab35b",
"parentId": "1042",
"isLeaf": false,
"molecule": {
"id": "sa_25ef12f2fdc69dfd611ab35b",
"inchikey": "BPJQBRNQTRLMIK-UHFFFAOYSA-N",
"smiles": "COc1ncc(C)cc1-c1nc(NC(=O)C2(c3ccc4c(c3)OC(F)(F)O4)CC2)ccc1C"
},
"smiles": "COc1ncc(C)cc1-c1nc(NC(=O)C2(c3ccc4c(c3)OC(F)(F)O4)CC2)ccc1C",
"reactionStepId": "sa_68f2961f23a29ade50a86405",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150166516A1;0495;1705719\",\"rsmi\":\"CC1(C)OB([c:9]2[c:3]([O:2][CH3:1])[n:4][cH:5][c:6]([CH3:7])[cH:8]2)OC1(C)C.Cl[c:10]1[n:11][c:12]([NH:13][C:14](=[O:15])[C:16]2([c:17]3[cH:18][c:19]4[c:20]([cH:21][cH:22]3)[O:23][C:24]([F:25])([F:26])[O:27]4)[CH2:28][CH2:29]2)[cH:30][cH:31][c:32]1[CH3:33]>CCOC(C)=O.COCCOC.O=C(O)O.[Na+].[Na+].c1ccc([PH](c2ccccc2)(c2ccccc2)[Pd]([PH](c2ccccc2)(c2ccccc2)c2ccccc2)([PH](c2ccccc2)(c2ccccc2)c2ccccc2)[PH](c2ccccc2)(c2ccccc2)c2ccccc2)cc1>[CH3:1][O:2][c:3]1[n:4][cH:5][c:6]([CH3:7])[cH:8][c:9]1-[c:10]1[n:11][c:12]([NH:13][C:14](=[O:15])[C:16]2([c:17]3[cH:18][c:19]4[c:20]([cH:21][cH:22]3)[O:23][C:24]([F:25])([F:26])[O:27]4)[CH2:28][CH2:29]2)[cH:30][cH:31][c:32]1[CH3:33]\"},\"mapped_reaction_smiles\":\"CC1(C)OB([c:9]2[c:3]([O:2][CH3:1])[n:4][cH:5][c:6]([CH3:7])[cH:8]2)OC1(C)C.Cl[c:10]1[n:11][c:12]([NH:13][C:14](=[O:15])[C:16]2([c:17]3[cH:18][c:19]4[c:20]([cH:21][cH:22]3)[O:23][C:24]([F:25])([F:26])[O:27]4)[CH2:28][CH2:29]2)[cH:30][cH:31][c:32]1[CH3:33]>CCOC(C)=O.COCCOC.O=C(O)O.[Na+].[Na+].c1ccc([PH](c2ccccc2)(c2ccccc2)[Pd]([PH](c2ccccc2)(c2ccccc2)c2ccccc2)([PH](c2ccccc2)(c2ccccc2)c2ccccc2)[PH](c2ccccc2)(c2ccccc2)c2ccccc2)cc1>[CH3:1][O:2][c:3]1[n:4][cH:5][c:6]([CH3:7])[cH:8][c:9]1-[c:10]1[n:11][c:12]([NH:13][C:14](=[O:15])[C:16]2([c:17]3[cH:18][c:19]4[c:20]([cH:21][cH:22]3)[O:23][C:24]([F:25])([F:26])[O:27]4)[CH2:28][CH2:29]2)[cH:30][cH:31][c:32]1[CH3:33]\"}",
"reactionStep": {
"id": "sa_68f2961f23a29ade50a86405",
"reactionHash": "0ca7b8ad5d6fb44f660c28a083ef2db99fe3dcbd2c5d9be5a98cc39e913fc332"
},
"children": [
{
"id": "1044",
"routeId": "sa_163c5e1b0738c45f42c5a73b",
"moleculeId": "sa_cfd7ce87e18484145809d50a",
"parentId": "1043",
"isLeaf": false,
"molecule": {
"id": "sa_cfd7ce87e18484145809d50a",
"inchikey": "BMIBJCFFZPYJHF-UHFFFAOYSA-N",
"smiles": "COc1ncc(C)cc1B1OC(C)(C)C(C)(C)O1"
},
"smiles": "COc1ncc(C)cc1B1OC(C)(C)C(C)(C)O1",
"reactionStepId": "sa_ef5b8c798a6ccfb3a6e3a815",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150166516A1;0445;1705696\",\"rsmi\":\"Br[c:9]1[c:3]([O:2][CH3:1])[n:4][cH:5][c:6]([CH3:7])[cH:8]1.CC1(C)OB([B:10]2[O:11][C:12]([CH3:13])([CH3:14])[C:15]([CH3:16])([CH3:17])[O:18]2)OC1(C)C>CC(=O)O.Cl[Pd]Cl.[Fe+2].[K+]>[CH3:1][O:2][c:3]1[n:4][cH:5][c:6]([CH3:7])[cH:8][c:9]1[B:10]1[O:11][C:12]([CH3:13])([CH3:14])[C:15]([CH3:16])([CH3:17])[O:18]1\"},\"mapped_reaction_smiles\":\"Br[c:9]1[c:3]([O:2][CH3:1])[n:4][cH:5][c:6]([CH3:7])[cH:8]1.CC1(C)OB([B:10]2[O:11][C:12]([CH3:13])([CH3:14])[C:15]([CH3:16])([CH3:17])[O:18]2)OC1(C)C>CC(=O)O.Cl[Pd]Cl.[Fe+2].[K+]>[CH3:1][O:2][c:3]1[n:4][cH:5][c:6]([CH3:7])[cH:8][c:9]1[B:10]1[O:11][C:12]([CH3:13])([CH3:14])[C:15]([CH3:16])([CH3:17])[O:18]1\"}",
"reactionStep": {
"id": "sa_ef5b8c798a6ccfb3a6e3a815",
"reactionHash": "43b0995447c0895b7bbb2163afa68bd28e4685ef6de695248cd49c9f20f089af"
},
"children": [
{
"id": "1045",
"routeId": "sa_163c5e1b0738c45f42c5a73b",
"moleculeId": "sa_e6c301388ac142801d4af5a2",
"parentId": "1044",
"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": "1046",
"routeId": "sa_163c5e1b0738c45f42c5a73b",
"moleculeId": "sa_418e154e11c45e435c0423bb",
"parentId": "1044",
"isLeaf": false,
"molecule": {
"id": "sa_418e154e11c45e435c0423bb",
"inchikey": "NDKLQBZACYGWAZ-UHFFFAOYSA-N",
"smiles": "COc1ncc(C)cc1Br"
},
"smiles": "COc1ncc(C)cc1Br",
"reactionStepId": "sa_c3b925b86f39360f1233e7f2",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150166516A1;0444;1705695\",\"rsmi\":\"I[CH3:1].[OH:2][c:3]1[n:4][cH:5][c:6]([CH3:7])[cH:8][c:9]1[Br:10]>ClCCl.O=C(O)O.[Ag+2]>[CH3:1][O:2][c:3]1[n:4][cH:5][c:6]([CH3:7])[cH:8][c:9]1[Br:10]\"},\"mapped_reaction_smiles\":\"I[CH3:1].[OH:2][c:3]1[n:4][cH:5][c:6]([CH3:7])[cH:8][c:9]1[Br:10]>ClCCl.O=C(O)O.[Ag+2]>[CH3:1][O:2][c:3]1[n:4][cH:5][c:6]([CH3:7])[cH:8][c:9]1[Br:10]\"}",
"reactionStep": {
"id": "sa_c3b925b86f39360f1233e7f2",
"reactionHash": "138f3f9c5027cdc45f23c0d68007897292a90f665ca2431071e609cfea0b03a3"
},
"children": [
{
"id": "1047",
"routeId": "sa_163c5e1b0738c45f42c5a73b",
"moleculeId": "sa_82fdccf7d1cc329c9db73f21",
"parentId": "1046",
"isLeaf": true,
"molecule": {
"id": "sa_82fdccf7d1cc329c9db73f21",
"inchikey": "INQOMBQAUSQDDS-UHFFFAOYSA-N",
"smiles": "CI"
},
"smiles": "CI",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "1048",
"routeId": "sa_163c5e1b0738c45f42c5a73b",
"moleculeId": "sa_e1c9509202a687a318fd10fa",
"parentId": "1046",
"isLeaf": true,
"molecule": {
"id": "sa_e1c9509202a687a318fd10fa",
"inchikey": "KHBRMXVUQOVORD-UHFFFAOYSA-N",
"smiles": "Cc1c[nH]c(=O)c(Br)c1"
},
"smiles": "Cc1cnc(O)c(Br)c1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
},
{
"id": "1049",
"routeId": "sa_163c5e1b0738c45f42c5a73b",
"moleculeId": "sa_701da92cca2d7546e36ddebd",
"parentId": "1043",
"isLeaf": false,
"molecule": {
"id": "sa_701da92cca2d7546e36ddebd",
"inchikey": "LDGZMPDLIYSAFD-UHFFFAOYSA-N",
"smiles": "Cc1ccc(NC(=O)C2(c3ccc4c(c3)OC(F)(F)O4)CC2)nc1Cl"
},
"smiles": "Cc1ccc(NC(=O)C2(c3ccc4c(c3)OC(F)(F)O4)CC2)nc1Cl",
"reactionStepId": "sa_ab52695d60be3b4d1f6058fa",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150166516A1;0421;1705685\",\"rsmi\":\"Cl[C:8](=[O:9])[C:10]1([c:11]2[cH:12][c:13]3[c:14]([cH:15][cH:16]2)[O:17][C:18]([F:19])([F:20])[O:21]3)[CH2:22][CH2:23]1.[CH3:1][c:2]1[c:3]([Cl:4])[n:5][c:6]([NH2:7])[cH:24][cH:25]1>CCN(CC)CC.ClCCl>[CH3:1][c:2]1[c:3]([Cl:4])[n:5][c:6]([NH:7][C:8](=[O:9])[C:10]2([c:11]3[cH:12][c:13]4[c:14]([cH:15][cH:16]3)[O:17][C:18]([F:19])([F:20])[O:21]4)[CH2:22][CH2:23]2)[cH:24][cH:25]1\"},\"mapped_reaction_smiles\":\"Cl[C:8](=[O:9])[C:10]1([c:11]2[cH:12][c:13]3[c:14]([cH:15][cH:16]2)[O:17][C:18]([F:19])([F:20])[O:21]3)[CH2:22][CH2:23]1.[CH3:1][c:2]1[c:3]([Cl:4])[n:5][c:6]([NH2:7])[cH:24][cH:25]1>CCN(CC)CC.ClCCl>[CH3:1][c:2]1[c:3]([Cl:4])[n:5][c:6]([NH:7][C:8](=[O:9])[C:10]2([c:11]3[cH:12][c:13]4[c:14]([cH:15][cH:16]3)[O:17][C:18]([F:19])([F:20])[O:21]4)[CH2:22][CH2:23]2)[cH:24][cH:25]1\"}",
"reactionStep": {
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"reactionHash": "aab33c8d8453efd5fb1904ac904f6c16cdb178cb8030918a9541fba69a444f17"
},
"children": [
{
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"routeId": "sa_163c5e1b0738c45f42c5a73b",
"moleculeId": "sa_2a374b8c063933a732a44bab",
"parentId": "1049",
"isLeaf": false,
"molecule": {
"id": "sa_2a374b8c063933a732a44bab",
"inchikey": "FVNYSBKXILOVTD-UHFFFAOYSA-N",
"smiles": "O=C(Cl)C1(c2ccc3c(c2)OC(F)(F)O3)CC1"
},
"smiles": "O=C(Cl)C1(c2ccc3c(c2)OC(F)(F)O3)CC1",
"reactionStepId": "sa_fa9c6006325da748c5c73ddb",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150166516A1;0420;1705684\",\"rsmi\":\"O=S(Cl)[Cl:3].O[C:2](=[O:1])[C:4]1([c:5]2[cH:6][c:7]3[c:8]([cH:9][cH:10]2)[O:11][C:12]([F:13])([F:14])[O:15]3)[CH2:16][CH2:17]1>CN(C)C=O>[O:1]=[C:2]([Cl:3])[C:4]1([c:5]2[cH:6][c:7]3[c:8]([cH:9][cH:10]2)[O:11][C:12]([F:13])([F:14])[O:15]3)[CH2:16][CH2:17]1\"},\"mapped_reaction_smiles\":\"O=S(Cl)[Cl:3].O[C:2](=[O:1])[C:4]1([c:5]2[cH:6][c:7]3[c:8]([cH:9][cH:10]2)[O:11][C:12]([F:13])([F:14])[O:15]3)[CH2:16][CH2:17]1>CN(C)C=O>[O:1]=[C:2]([Cl:3])[C:4]1([c:5]2[cH:6][c:7]3[c:8]([cH:9][cH:10]2)[O:11][C:12]([F:13])([F:14])[O:15]3)[CH2:16][CH2:17]1\"}",
"reactionStep": {
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"reactionHash": "370c588420ba1aaadcedad4b90612b8b1308d761811472858c6567b685f9e80c"
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"children": [
{
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"routeId": "sa_163c5e1b0738c45f42c5a73b",
"moleculeId": "sa_cd67ce42f230ef1a4063353c",
"parentId": "1050",
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"molecule": {
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"inchikey": "FYSNRJHAOHDILO-UHFFFAOYSA-N",
"smiles": "O=S(Cl)Cl"
},
"smiles": "O=S(Cl)Cl",
"reactionStepId": null,
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},
{
"id": "1052",
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"parentId": "1050",
"isLeaf": true,
"molecule": {
"id": "sa_9be965c22871bbe5378075e7",
"inchikey": "IELWGOUPQRHXLS-UHFFFAOYSA-N",
"smiles": "O=C(O)C1(c2ccc3c(c2)OC(F)(F)O3)CC1"
},
"smiles": "O=C(O)C1(c2ccc3c(c2)OC(F)(F)O3)CC1",
"reactionStepId": null,
"template": null,
"metadata": null,
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}
]
},
{
"id": "1053",
"routeId": "sa_163c5e1b0738c45f42c5a73b",
"moleculeId": "sa_e141490976a2f1323659aa34",
"parentId": "1049",
"isLeaf": true,
"molecule": {
"id": "sa_e141490976a2f1323659aa34",
"inchikey": "KPZRCZMNXPBHEH-UHFFFAOYSA-N",
"smiles": "Cc1ccc(N)nc1Cl"
},
"smiles": "Cc1ccc(N)nc1Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
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"children": []
}
]
}
]
}
]
}
}