Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
Cc1nc(-c2cc(CN3CCN(C(=O)OC(C)(C)C)CC3)cnc2F)c2ncn(C3CCCCO3)c2n1
InChiKey
USMNKNIEDRFSCJ-UHFFFAOYSA-N
Route Signature
4485c50d5ccae94ea1f5541d37c2bfbc29911a881d5db9a4bae0fee01c98f418
Synthesis route with 4 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_099ca3c586911032f6221f6c",
"signature": "4485c50d5ccae94ea1f5541d37c2bfbc29911a881d5db9a4bae0fee01c98f418",
"contentHash": "87b0b6c1e39ac563d7579ed154c063299d8a9c72a8117d601297d3e32bba0a63",
"length": 4,
"isConvergent": true
},
"target": {
"id": "sa_4fb4f7d4514a8f9655af209d",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-00485",
"moleculeId": "sa_f7571d72978896dedcd62d82",
"smiles": "Cc1nc(-c2cc(CN3CCN(C(=O)OC(C)(C)C)CC3)cnc2F)c2ncn(C3CCCCO3)c2n1",
"routeLength": 4,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_f7571d72978896dedcd62d82",
"inchikey": "USMNKNIEDRFSCJ-UHFFFAOYSA-N",
"smiles": "Cc1nc(-c2cc(CN3CCN(C(=O)OC(C)(C)C)CC3)cnc2F)c2ncn(C3CCCCO3)c2n1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "9518",
"routeId": "sa_099ca3c586911032f6221f6c",
"moleculeId": "sa_f7571d72978896dedcd62d82",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_f7571d72978896dedcd62d82",
"inchikey": "USMNKNIEDRFSCJ-UHFFFAOYSA-N",
"smiles": "Cc1nc(-c2cc(CN3CCN(C(=O)OC(C)(C)C)CC3)cnc2F)c2ncn(C3CCCCO3)c2n1"
},
"smiles": "Cc1nc(-c2cc(CN3CCN(C(=O)OC(C)(C)C)CC3)cnc2F)c2ncn(C3CCCCO3)c2n1",
"reactionStepId": "sa_250a9d49f0400da19078022d",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130079303A1;0773;1352151\",\"rsmi\":\"Cl[c:4]1[n:3][c:2]([CH3:1])[n:37][c:36]2[c:26]1[n:27][cH:28][n:29]2[CH:30]1[CH2:31][CH2:32][CH2:33][CH2:34][O:35]1.OB(O)[c:5]1[c:6]([F:7])[n:8][cH:9][c:10]([CH2:11][N:12]2[CH2:13][CH2:14][N:15]([C:16](=[O:17])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22])[CH2:23][CH2:24]2)[cH:25]1>CC(=O)O.CCO.CN(C)c1ccc(P(C(C)(C)C)C(C)(C)C)cc1.CN(C)c1ccc(P(C(C)(C)C)C(C)(C)C)cc1.Cl[Pd]Cl.O.[K+]>[CH3:1][c:2]1[n:3][c:4](-[c:5]2[c:6]([F:7])[n:8][cH:9][c:10]([CH2:11][N:12]3[CH2:13][CH2:14][N:15]([C:16](=[O:17])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22])[CH2:23][CH2:24]3)[cH:25]2)[c:26]2[n:27][cH:28][n:29]([CH:30]3[CH2:31][CH2:32][CH2:33][CH2:34][O:35]3)[c:36]2[n:37]1\"},\"mapped_reaction_smiles\":\"Cl[c:4]1[n:3][c:2]([CH3:1])[n:37][c:36]2[c:26]1[n:27][cH:28][n:29]2[CH:30]1[CH2:31][CH2:32][CH2:33][CH2:34][O:35]1.OB(O)[c:5]1[c:6]([F:7])[n:8][cH:9][c:10]([CH2:11][N:12]2[CH2:13][CH2:14][N:15]([C:16](=[O:17])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22])[CH2:23][CH2:24]2)[cH:25]1>CC(=O)O.CCO.CN(C)c1ccc(P(C(C)(C)C)C(C)(C)C)cc1.CN(C)c1ccc(P(C(C)(C)C)C(C)(C)C)cc1.Cl[Pd]Cl.O.[K+]>[CH3:1][c:2]1[n:3][c:4](-[c:5]2[c:6]([F:7])[n:8][cH:9][c:10]([CH2:11][N:12]3[CH2:13][CH2:14][N:15]([C:16](=[O:17])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22])[CH2:23][CH2:24]3)[cH:25]2)[c:26]2[n:27][cH:28][n:29]([CH:30]3[CH2:31][CH2:32][CH2:33][CH2:34][O:35]3)[c:36]2[n:37]1\"}",
"reactionStep": {
"id": "sa_250a9d49f0400da19078022d",
"reactionHash": "9be6d3c2372059e6bee824d2fc5c3aa91c8c64bbdf0781c69fe11eb5258488d5"
},
"children": [
{
"id": "9519",
"routeId": "sa_099ca3c586911032f6221f6c",
"moleculeId": "sa_aebe2e538a14bbdf0f63c20b",
"parentId": "9518",
"isLeaf": false,
"molecule": {
"id": "sa_aebe2e538a14bbdf0f63c20b",
"inchikey": "PMXPAGSGEARALL-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)N1CCN(Cc2cnc(F)c(B(O)O)c2)CC1"
},
"smiles": "CC(C)(C)OC(=O)N1CCN(Cc2cnc(F)c(B(O)O)c2)CC1",
"reactionStepId": "sa_f376f77c83ebb957c2311806",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130079303A1;0639;1352083\",\"rsmi\":\"CC(C)O[B:19]([O:20]C(C)C)[O:21]C(C)C.[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][N:11]([CH2:12][c:13]2[cH:14][n:15][c:16]([F:17])[cH:18][cH:22]2)[CH2:23][CH2:24]1>C1CCOC1.CC(C)NC(C)C.CC(C)NC(C)C.[Li+].[Li]CCCC>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][N:11]([CH2:12][c:13]2[cH:14][n:15][c:16]([F:17])[c:18]([B:19]([OH:20])[OH:21])[cH:22]2)[CH2:23][CH2:24]1\"},\"mapped_reaction_smiles\":\"CC(C)O[B:19]([O:20]C(C)C)[O:21]C(C)C.[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][N:11]([CH2:12][c:13]2[cH:14][n:15][c:16]([F:17])[cH:18][cH:22]2)[CH2:23][CH2:24]1>C1CCOC1.CC(C)NC(C)C.CC(C)NC(C)C.[Li+].[Li]CCCC>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][N:11]([CH2:12][c:13]2[cH:14][n:15][c:16]([F:17])[c:18]([B:19]([OH:20])[OH:21])[cH:22]2)[CH2:23][CH2:24]1\"}",
"reactionStep": {
"id": "sa_f376f77c83ebb957c2311806",
"reactionHash": "cc2ccb34b19c894ad07435f5791ef501703605712e5ac56d776cfbb5cab49572"
},
"children": [
{
"id": "9520",
"routeId": "sa_099ca3c586911032f6221f6c",
"moleculeId": "sa_0c3a1c72e8778c8e8b205e29",
"parentId": "9519",
"isLeaf": true,
"molecule": {
"id": "sa_0c3a1c72e8778c8e8b205e29",
"inchikey": "NHDIQVFFNDKAQU-UHFFFAOYSA-N",
"smiles": "CC(C)OB(OC(C)C)OC(C)C"
},
"smiles": "CC(C)OB(OC(C)C)OC(C)C",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "9521",
"routeId": "sa_099ca3c586911032f6221f6c",
"moleculeId": "sa_f1629625c0e2857c8e367ee1",
"parentId": "9519",
"isLeaf": false,
"molecule": {
"id": "sa_f1629625c0e2857c8e367ee1",
"inchikey": "SPDOWZZQVRBAFK-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)N1CCN(Cc2ccc(F)nc2)CC1"
},
"smiles": "CC(C)(C)OC(=O)N1CCN(Cc2ccc(F)nc2)CC1",
"reactionStepId": "sa_8f63c04a153988c197e4c5b8",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130079303A1;0638;1352082\",\"rsmi\":\"Br[CH2:12][c:13]1[cH:14][cH:15][c:16]([F:17])[n:18][cH:19]1.[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][NH:11][CH2:20][CH2:21]1>CN(C)C=O>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][N:11]([CH2:12][c:13]2[cH:14][cH:15][c:16]([F:17])[n:18][cH:19]2)[CH2:20][CH2:21]1\"},\"mapped_reaction_smiles\":\"Br[CH2:12][c:13]1[cH:14][cH:15][c:16]([F:17])[n:18][cH:19]1.[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][NH:11][CH2:20][CH2:21]1>CN(C)C=O>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][N:11]([CH2:12][c:13]2[cH:14][cH:15][c:16]([F:17])[n:18][cH:19]2)[CH2:20][CH2:21]1\"}",
"reactionStep": {
"id": "sa_8f63c04a153988c197e4c5b8",
"reactionHash": "a35f328a0dc3ee0b42805bfbaefcb6821a868bc8ed38a04b5e57c743afb28559"
},
"children": [
{
"id": "9522",
"routeId": "sa_099ca3c586911032f6221f6c",
"moleculeId": "sa_04c50a88932aa2c9d9b979b4",
"parentId": "9521",
"isLeaf": true,
"molecule": {
"id": "sa_04c50a88932aa2c9d9b979b4",
"inchikey": "CWXPZXBSDSIRCS-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)N1CCNCC1"
},
"smiles": "CC(C)(C)OC(=O)N1CCNCC1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "9523",
"routeId": "sa_099ca3c586911032f6221f6c",
"moleculeId": "sa_aa1e563cf804b9c546554c97",
"parentId": "9521",
"isLeaf": false,
"molecule": {
"id": "sa_aa1e563cf804b9c546554c97",
"inchikey": "IUJPAAPIEURDEZ-UHFFFAOYSA-N",
"smiles": "Fc1ccc(CBr)cn1"
},
"smiles": "Fc1ccc(CBr)cn1",
"reactionStepId": "sa_bd2bc9456ba7afd2dabfa1fe",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130079303A1;0637;1352081\",\"rsmi\":\"O=C1CCC(=O)N1[Br:7].[F:1][c:2]1[n:3][cH:4][c:5]([CH3:6])[cH:8][cH:9]1>ClC(Cl)(Cl)Cl.O=C(OOC(=O)c1ccccc1)c1ccccc1>[F:1][c:2]1[n:3][cH:4][c:5]([CH2:6][Br:7])[cH:8][cH:9]1\"},\"mapped_reaction_smiles\":\"O=C1CCC(=O)N1[Br:7].[F:1][c:2]1[n:3][cH:4][c:5]([CH3:6])[cH:8][cH:9]1>ClC(Cl)(Cl)Cl.O=C(OOC(=O)c1ccccc1)c1ccccc1>[F:1][c:2]1[n:3][cH:4][c:5]([CH2:6][Br:7])[cH:8][cH:9]1\"}",
"reactionStep": {
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"reactionHash": "756dfafaa897f80296152b83e4fbf94de04783497e8c19ffadd0a9426f78baf0"
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"children": [
{
"id": "9524",
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"moleculeId": "sa_ae6aec1ddce02b3218852492",
"parentId": "9523",
"isLeaf": true,
"molecule": {
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"inchikey": "AOSOZARHUJMBLZ-UHFFFAOYSA-N",
"smiles": "Cc1ccc(F)nc1"
},
"smiles": "Cc1ccc(F)nc1",
"reactionStepId": null,
"template": null,
"metadata": null,
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"children": []
},
{
"id": "9525",
"routeId": "sa_099ca3c586911032f6221f6c",
"moleculeId": "sa_ccdcf23ac83e7a68bfa4f2e5",
"parentId": "9523",
"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,
"children": []
}
]
}
]
}
]
},
{
"id": "9526",
"routeId": "sa_099ca3c586911032f6221f6c",
"moleculeId": "sa_fa36dc4ea7e9f6b698a3c9fd",
"parentId": "9518",
"isLeaf": false,
"molecule": {
"id": "sa_fa36dc4ea7e9f6b698a3c9fd",
"inchikey": "SGVQCLQGWDCDKO-UHFFFAOYSA-N",
"smiles": "Cc1nc(Cl)c2ncn(C3CCCCO3)c2n1"
},
"smiles": "Cc1nc(Cl)c2ncn(C3CCCCO3)c2n1",
"reactionStepId": "sa_53a2c55c3559c1bf16ce9100",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130079303A1;0555;1352044\",\"rsmi\":\"[CH3:1][c:2]1[n:3][c:4]([Cl:5])[c:6]2[n:7][cH:8][nH:9][c:16]2[n:17]1.[CH:10]1=[CH:11][CH2:12][CH2:13][CH2:14][O:15]1>Cc1ccc(S(=O)(=O)O)cc1.ClCCl.O=C(O)O.[Na+]>[CH3:1][c:2]1[n:3][c:4]([Cl:5])[c:6]2[n:7][cH:8][n:9]([CH:10]3[CH2:11][CH2:12][CH2:13][CH2:14][O:15]3)[c:16]2[n:17]1\"},\"mapped_reaction_smiles\":\"[CH3:1][c:2]1[n:3][c:4]([Cl:5])[c:6]2[n:7][cH:8][nH:9][c:16]2[n:17]1.[CH:10]1=[CH:11][CH2:12][CH2:13][CH2:14][O:15]1>Cc1ccc(S(=O)(=O)O)cc1.ClCCl.O=C(O)O.[Na+]>[CH3:1][c:2]1[n:3][c:4]([Cl:5])[c:6]2[n:7][cH:8][n:9]([CH:10]3[CH2:11][CH2:12][CH2:13][CH2:14][O:15]3)[c:16]2[n:17]1\"}",
"reactionStep": {
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"children": [
{
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"moleculeId": "sa_359472b115a712c065ff6c19",
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"isLeaf": true,
"molecule": {
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"inchikey": "BUDQDWGNQVEFAC-UHFFFAOYSA-N",
"smiles": "C1=COCCC1"
},
"smiles": "C1=COCCC1",
"reactionStepId": null,
"template": null,
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},
{
"id": "9528",
"routeId": "sa_099ca3c586911032f6221f6c",
"moleculeId": "sa_f4befc612da5ae7e939edf23",
"parentId": "9526",
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"molecule": {
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"inchikey": "KKTMNZXPLHVDBC-UHFFFAOYSA-N",
"smiles": "Cc1nc(Cl)c2nc[nH]c2n1"
},
"smiles": "Cc1nc(Cl)c2nc[nH]c2n1",
"reactionStepId": "sa_309102467b521e4a10a6ce13",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130079303A1;0554;1352043\",\"rsmi\":\"CCO[CH:8](O)O.[CH3:1][c:2]1[n:3][c:4]([Cl:5])[c:6]([NH2:7])[c:10]([NH2:9])[n:11]1>>[CH3:1][c:2]1[n:3][c:4]([Cl:5])[c:6]2[n:7][cH:8][nH:9][c:10]2[n:11]1\"},\"mapped_reaction_smiles\":\"CCO[CH:8](O)O.[CH3:1][c:2]1[n:3][c:4]([Cl:5])[c:6]([NH2:7])[c:10]([NH2:9])[n:11]1>>[CH3:1][c:2]1[n:3][c:4]([Cl:5])[c:6]2[n:7][cH:8][nH:9][c:10]2[n:11]1\"}",
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"children": [
{
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"smiles": "CCOC(O)O",
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{
"id": "9530",
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"inchikey": "SGPFPRGCGZLZPP-UHFFFAOYSA-N",
"smiles": "Cc1nc(N)c(N)c(Cl)n1"
},
"smiles": "Cc1nc(N)c(N)c(Cl)n1",
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}
]
}
]
}
]
}
}