Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CC#CC(=O)N1CCC[C@H]1c1nc(-c2ccc(C(=O)Nc3cc(C)ccn3)cc2)c2c(N)nccn12
InChiKey
LZWPQYFMKORGFH-FQEVSTJZSA-N
Route Signature
70389db41a95d5bedcd6b01bf15eda4ff8cdbc5e64c880cf8e5135fb1def5f30
Synthesis route with 4 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_cb5f1817e0b6f7726106ba4c",
"signature": "70389db41a95d5bedcd6b01bf15eda4ff8cdbc5e64c880cf8e5135fb1def5f30",
"contentHash": "7eb6499cd5406c5a841fd520c7cbd03210eff40a12c6bba2885ae836aba6cb9b",
"length": 4,
"isConvergent": true
},
"target": {
"id": "sa_6a10bd54bc6128fb0bd01d78",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-00254",
"moleculeId": "sa_814db03778c222086564a5de",
"smiles": "CC#CC(=O)N1CCC[C@H]1c1nc(-c2ccc(C(=O)Nc3cc(C)ccn3)cc2)c2c(N)nccn12",
"routeLength": 4,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_814db03778c222086564a5de",
"inchikey": "LZWPQYFMKORGFH-FQEVSTJZSA-N",
"smiles": "CC#CC(=O)N1CCC[C@H]1c1nc(-c2ccc(C(=O)Nc3cc(C)ccn3)cc2)c2c(N)nccn12"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "9329",
"routeId": "sa_cb5f1817e0b6f7726106ba4c",
"moleculeId": "sa_814db03778c222086564a5de",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_814db03778c222086564a5de",
"inchikey": "LZWPQYFMKORGFH-FQEVSTJZSA-N",
"smiles": "CC#CC(=O)N1CCC[C@H]1c1nc(-c2ccc(C(=O)Nc3cc(C)ccn3)cc2)c2c(N)nccn12"
},
"smiles": "CC#CC(=O)N1CCC[C@H]1c1nc(-c2ccc(C(=O)Nc3cc(C)ccn3)cc2)c2c(N)nccn12",
"reactionStepId": "sa_9e4849b0973a38276d4822a5",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160159810A1;0349;1889675\",\"rsmi\":\"O[C:4]([C:3]#[C:2][CH3:1])=[O:5].[NH:6]1[CH2:7][CH2:8][CH2:9][C@H:10]1[c:11]1[n:12][c:13](-[c:14]2[cH:15][cH:16][c:17]([C:18](=[O:19])[NH:20][c:21]3[n:22][cH:23][cH:24][c:25]([CH3:26])[cH:27]3)[cH:28][cH:29]2)[c:30]2[c:31]([NH2:32])[n:33][cH:34][cH:35][n:36]12>>[CH3:1][C:2]#[C:3][C:4](=[O:5])[N:6]1[CH2:7][CH2:8][CH2:9][C@H:10]1[c:11]1[n:12][c:13](-[c:14]2[cH:15][cH:16][c:17]([C:18](=[O:19])[NH:20][c:21]3[n:22][cH:23][cH:24][c:25]([CH3:26])[cH:27]3)[cH:28][cH:29]2)[c:30]2[c:31]([NH2:32])[n:33][cH:34][cH:35][n:36]12\"},\"mapped_reaction_smiles\":\"O[C:4]([C:3]#[C:2][CH3:1])=[O:5].[NH:6]1[CH2:7][CH2:8][CH2:9][C@H:10]1[c:11]1[n:12][c:13](-[c:14]2[cH:15][cH:16][c:17]([C:18](=[O:19])[NH:20][c:21]3[n:22][cH:23][cH:24][c:25]([CH3:26])[cH:27]3)[cH:28][cH:29]2)[c:30]2[c:31]([NH2:32])[n:33][cH:34][cH:35][n:36]12>>[CH3:1][C:2]#[C:3][C:4](=[O:5])[N:6]1[CH2:7][CH2:8][CH2:9][C@H:10]1[c:11]1[n:12][c:13](-[c:14]2[cH:15][cH:16][c:17]([C:18](=[O:19])[NH:20][c:21]3[n:22][cH:23][cH:24][c:25]([CH3:26])[cH:27]3)[cH:28][cH:29]2)[c:30]2[c:31]([NH2:32])[n:33][cH:34][cH:35][n:36]12\"}",
"reactionStep": {
"id": "sa_9e4849b0973a38276d4822a5",
"reactionHash": "4d0e58f3105e8a9e1fc75984a7aaa8401a5c26fbceafea3b7868eb9058cc68b2"
},
"children": [
{
"id": "9330",
"routeId": "sa_cb5f1817e0b6f7726106ba4c",
"moleculeId": "sa_7e60bfb3087e74bb82cb4722",
"parentId": "9329",
"isLeaf": false,
"molecule": {
"id": "sa_7e60bfb3087e74bb82cb4722",
"inchikey": "BGBBBTSHGYTJMO-KRWDZBQOSA-N",
"smiles": "Cc1ccnc(NC(=O)c2ccc(-c3nc([C@@H]4CCCN4)n4ccnc(N)c34)cc2)c1"
},
"smiles": "Cc1ccnc(NC(=O)c2ccc(-c3nc([C@@H]4CCCN4)n4ccnc(N)c34)cc2)c1",
"reactionStepId": "sa_f38f178c2617488660c7986a",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160159810A1;0347;1889674\",\"rsmi\":\"CC1(C)OB([c:11]2[cH:10][cH:9][c:8]([C:6]([NH:5][c:4]3[cH:3][c:2]([CH3:1])[cH:31][cH:30][n:29]3)=[O:7])[cH:28][cH:27]2)OC1(C)C.O=C(OCc1ccccc1)[N:25]1[C@H:21]([c:20]2[n:19]3[c:13]([c:12](Br)[n:26]2)[c:14]([NH2:15])[n:16][cH:17][cH:18]3)[CH2:22][CH2:23][CH2:24]1>>[CH3:1][c:2]1[cH:3][c:4]([NH:5][C:6](=[O:7])[c:8]2[cH:9][cH:10][c:11](-[c:12]3[c:13]4[c:14]([NH2:15])[n:16][cH:17][cH:18][n:19]4[c:20]([C@@H:21]4[CH2:22][CH2:23][CH2:24][NH:25]4)[n:26]3)[cH:27][cH:28]2)[n:29][cH:30][cH:31]1\"},\"mapped_reaction_smiles\":\"CC1(C)OB([c:11]2[cH:10][cH:9][c:8]([C:6]([NH:5][c:4]3[cH:3][c:2]([CH3:1])[cH:31][cH:30][n:29]3)=[O:7])[cH:28][cH:27]2)OC1(C)C.O=C(OCc1ccccc1)[N:25]1[C@H:21]([c:20]2[n:19]3[c:13]([c:12](Br)[n:26]2)[c:14]([NH2:15])[n:16][cH:17][cH:18]3)[CH2:22][CH2:23][CH2:24]1>>[CH3:1][c:2]1[cH:3][c:4]([NH:5][C:6](=[O:7])[c:8]2[cH:9][cH:10][c:11](-[c:12]3[c:13]4[c:14]([NH2:15])[n:16][cH:17][cH:18][n:19]4[c:20]([C@@H:21]4[CH2:22][CH2:23][CH2:24][NH:25]4)[n:26]3)[cH:27][cH:28]2)[n:29][cH:30][cH:31]1\"}",
"reactionStep": {
"id": "sa_f38f178c2617488660c7986a",
"reactionHash": "62ceda6cc2ec13561aa39c9adc608941496891964ec9a3c50cf6a24e8c322d44"
},
"children": [
{
"id": "9331",
"routeId": "sa_cb5f1817e0b6f7726106ba4c",
"moleculeId": "sa_eac8d442a8136d2fad06f436",
"parentId": "9330",
"isLeaf": false,
"molecule": {
"id": "sa_eac8d442a8136d2fad06f436",
"inchikey": "DLXYYJDQLZHBNU-ZDUSSCGKSA-N",
"smiles": "Nc1nccn2c([C@@H]3CCCN3C(=O)OCc3ccccc3)nc(Br)c12"
},
"smiles": "Nc1nccn2c([C@@H]3CCCN3C(=O)OCc3ccccc3)nc(Br)c12",
"reactionStepId": "sa_5367aa91bedb82c4eb10f506",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160159810A1;0321;1889662\",\"rsmi\":\"Cl[c:2]1[n:3][cH:4][cH:5][n:6]2[c:7]([C@@H:8]3[CH2:9][CH2:10][CH2:11][N:12]3[C:13](=[O:14])[O:15][CH2:16][c:17]3[cH:18][cH:19][cH:20][cH:21][cH:22]3)[n:23][c:24]([Br:25])[c:26]12.[NH3:1]>CC(C)O>[NH2:1][c:2]1[n:3][cH:4][cH:5][n:6]2[c:7]([C@@H:8]3[CH2:9][CH2:10][CH2:11][N:12]3[C:13](=[O:14])[O:15][CH2:16][c:17]3[cH:18][cH:19][cH:20][cH:21][cH:22]3)[n:23][c:24]([Br:25])[c:26]12\"},\"mapped_reaction_smiles\":\"Cl[c:2]1[n:3][cH:4][cH:5][n:6]2[c:7]([C@@H:8]3[CH2:9][CH2:10][CH2:11][N:12]3[C:13](=[O:14])[O:15][CH2:16][c:17]3[cH:18][cH:19][cH:20][cH:21][cH:22]3)[n:23][c:24]([Br:25])[c:26]12.[NH3:1]>CC(C)O>[NH2:1][c:2]1[n:3][cH:4][cH:5][n:6]2[c:7]([C@@H:8]3[CH2:9][CH2:10][CH2:11][N:12]3[C:13](=[O:14])[O:15][CH2:16][c:17]3[cH:18][cH:19][cH:20][cH:21][cH:22]3)[n:23][c:24]([Br:25])[c:26]12\"}",
"reactionStep": {
"id": "sa_5367aa91bedb82c4eb10f506",
"reactionHash": "8e53de000f924480feefbb9d9109def9f5d34591a05bf9de0a3af6ab2c16a538"
},
"children": [
{
"id": "9332",
"routeId": "sa_cb5f1817e0b6f7726106ba4c",
"moleculeId": "sa_40d899e05d18da2bfb15fd98",
"parentId": "9331",
"isLeaf": false,
"molecule": {
"id": "sa_40d899e05d18da2bfb15fd98",
"inchikey": "BQNYTGLJPKJADU-ZDUSSCGKSA-N",
"smiles": "O=C(OCc1ccccc1)N1CCC[C@H]1c1nc(Br)c2c(Cl)nccn12"
},
"smiles": "O=C(OCc1ccccc1)N1CCC[C@H]1c1nc(Br)c2c(Cl)nccn12",
"reactionStepId": "sa_40d1f65daf50cd39655739a7",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160159810A1;0320;1889661\",\"rsmi\":\"O=C1CCC(=O)N1[Br:19].[O:1]=[C:2]([O:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[N:11]1[CH2:12][CH2:13][CH2:14][C@H:15]1[c:16]1[n:17][cH:18][c:20]2[c:21]([Cl:22])[n:23][cH:24][cH:25][n:26]12>CCOC(C)=O.CN(C)C=O.O.O.Cl.[Na+]>[O:1]=[C:2]([O:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[N:11]1[CH2:12][CH2:13][CH2:14][C@H:15]1[c:16]1[n:17][c:18]([Br:19])[c:20]2[c:21]([Cl:22])[n:23][cH:24][cH:25][n:26]12\"},\"mapped_reaction_smiles\":\"O=C1CCC(=O)N1[Br:19].[O:1]=[C:2]([O:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[N:11]1[CH2:12][CH2:13][CH2:14][C@H:15]1[c:16]1[n:17][cH:18][c:20]2[c:21]([Cl:22])[n:23][cH:24][cH:25][n:26]12>CCOC(C)=O.CN(C)C=O.O.O.Cl.[Na+]>[O:1]=[C:2]([O:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[N:11]1[CH2:12][CH2:13][CH2:14][C@H:15]1[c:16]1[n:17][c:18]([Br:19])[c:20]2[c:21]([Cl:22])[n:23][cH:24][cH:25][n:26]12\"}",
"reactionStep": {
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"reactionHash": "5e4b03fcb69138157212fcd1e97502d83cef2e2891e8e39496bc659c5e6f62af"
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"children": [
{
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"routeId": "sa_cb5f1817e0b6f7726106ba4c",
"moleculeId": "sa_346e90841e70964c5254eb05",
"parentId": "9332",
"isLeaf": true,
"molecule": {
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"inchikey": "CVBYUIZTUMXADS-AWEZNQCLSA-N",
"smiles": "O=C(OCc1ccccc1)N1CCC[C@H]1c1ncc2c(Cl)nccn12"
},
"smiles": "O=C(OCc1ccccc1)N1CCC[C@H]1c1ncc2c(Cl)nccn12",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "9334",
"routeId": "sa_cb5f1817e0b6f7726106ba4c",
"moleculeId": "sa_ccdcf23ac83e7a68bfa4f2e5",
"parentId": "9332",
"isLeaf": true,
"molecule": {
"id": "sa_ccdcf23ac83e7a68bfa4f2e5",
"inchikey": "PCLIMKBDDGJMGD-UHFFFAOYSA-N",
"smiles": "O=C1CCC(=O)N1Br"
},
"smiles": "O=C1CCC(=O)N1Br",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
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}
]
},
{
"id": "9335",
"routeId": "sa_cb5f1817e0b6f7726106ba4c",
"moleculeId": "sa_c9679fdd876f32f86b77fb69",
"parentId": "9331",
"isLeaf": true,
"molecule": {
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"inchikey": "QGZKDVFQNNGYKY-UHFFFAOYSA-N",
"smiles": "N"
},
"smiles": "N",
"reactionStepId": null,
"template": null,
"metadata": null,
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}
]
},
{
"id": "9336",
"routeId": "sa_cb5f1817e0b6f7726106ba4c",
"moleculeId": "sa_8ba52ac96279fa5e98cb886b",
"parentId": "9330",
"isLeaf": false,
"molecule": {
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"inchikey": "SRNLWGKIMGETIM-UHFFFAOYSA-N",
"smiles": "Cc1ccnc(NC(=O)c2ccc(B3OC(C)(C)C(C)(C)O3)cc2)c1"
},
"smiles": "Cc1ccnc(NC(=O)c2ccc(B3OC(C)(C)C(C)(C)O3)cc2)c1",
"reactionStepId": "sa_e994ae71c677d10bf32fe4f6",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160159810A1;0345;1889673\",\"rsmi\":\"Cl[C:6](=[O:7])[c:8]1[cH:9][cH:10][c:11]([B:12]2[O:13][C:14]([CH3:15])([CH3:16])[C:17]([CH3:18])([CH3:19])[O:20]2)[cH:21][cH:22]1.[CH3:1][c:2]1[cH:3][c:4]([NH2:5])[n:23][cH:24][cH:25]1>C1CCOC1.C[Si](C)(C)N[Si](C)(C)C.ClCCl.[Li+]>[CH3:1][c:2]1[cH:3][c:4]([NH:5][C:6](=[O:7])[c:8]2[cH:9][cH:10][c:11]([B:12]3[O:13][C:14]([CH3:15])([CH3:16])[C:17]([CH3:18])([CH3:19])[O:20]3)[cH:21][cH:22]2)[n:23][cH:24][cH:25]1\"},\"mapped_reaction_smiles\":\"Cl[C:6](=[O:7])[c:8]1[cH:9][cH:10][c:11]([B:12]2[O:13][C:14]([CH3:15])([CH3:16])[C:17]([CH3:18])([CH3:19])[O:20]2)[cH:21][cH:22]1.[CH3:1][c:2]1[cH:3][c:4]([NH2:5])[n:23][cH:24][cH:25]1>C1CCOC1.C[Si](C)(C)N[Si](C)(C)C.ClCCl.[Li+]>[CH3:1][c:2]1[cH:3][c:4]([NH:5][C:6](=[O:7])[c:8]2[cH:9][cH:10][c:11]([B:12]3[O:13][C:14]([CH3:15])([CH3:16])[C:17]([CH3:18])([CH3:19])[O:20]3)[cH:21][cH:22]2)[n:23][cH:24][cH:25]1\"}",
"reactionStep": {
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"reactionHash": "9c1271402270a397d62019abe49af9677e7e22bc0844829da3d08e90f4f5b9b3"
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"children": [
{
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"moleculeId": "sa_527202065c212b99f42042eb",
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"molecule": {
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"inchikey": "ORLGLBZRQYOWNA-UHFFFAOYSA-N",
"smiles": "Cc1ccnc(N)c1"
},
"smiles": "Cc1ccnc(N)c1",
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{
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"molecule": {
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"inchikey": "WOCXUWRCQSFHNJ-UHFFFAOYSA-N",
"smiles": "CC1(C)OB(c2ccc(C(=O)Cl)cc2)OC1(C)C"
},
"smiles": "CC1(C)OB(c2ccc(C(=O)Cl)cc2)OC1(C)C",
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}
]
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]
},
{
"id": "9339",
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"moleculeId": "sa_2f9d8eaa4a076b2e579c9a85",
"parentId": "9329",
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"molecule": {
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"inchikey": "LUEHNHVFDCZTGL-UHFFFAOYSA-N",
"smiles": "CC#CC(=O)O"
},
"smiles": "CC#CC(=O)O",
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"children": []
}
]
}
}