Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
COCc1cnc(N2CCC([C@H]3C[C@H]3CCOc3cc(F)c(CC(=O)N4CCC4)c(F)c3)CC2)nc1
InChiKey
QWNGDOXELSIKNT-IFMALSPDSA-N
Route Signature
348b8e8a9218488df4483dfeb018523bd80eb623daeb7c7b6580bf8a31b8e36d
Synthesis route with 5 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_1f100147fcfa468df895ddbd",
"signature": "348b8e8a9218488df4483dfeb018523bd80eb623daeb7c7b6580bf8a31b8e36d",
"contentHash": "147796e7cf92ec73f3daffb77dc6e061860440883b3ed301d1a1f4f09770f058",
"length": 5,
"isConvergent": true
},
"target": {
"id": "sa_1af7cd61149d109ca3d08ebc",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-04314",
"moleculeId": "sa_15d73b5c4837afb78dfcd78b",
"smiles": "COCc1cnc(N2CCC([C@H]3C[C@H]3CCOc3cc(F)c(CC(=O)N4CCC4)c(F)c3)CC2)nc1",
"routeLength": 5,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_15d73b5c4837afb78dfcd78b",
"inchikey": "QWNGDOXELSIKNT-IFMALSPDSA-N",
"smiles": "COCc1cnc(N2CCC([C@H]3C[C@H]3CCOc3cc(F)c(CC(=O)N4CCC4)c(F)c3)CC2)nc1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "11211",
"routeId": "sa_1f100147fcfa468df895ddbd",
"moleculeId": "sa_15d73b5c4837afb78dfcd78b",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_15d73b5c4837afb78dfcd78b",
"inchikey": "QWNGDOXELSIKNT-IFMALSPDSA-N",
"smiles": "COCc1cnc(N2CCC([C@H]3C[C@H]3CCOc3cc(F)c(CC(=O)N4CCC4)c(F)c3)CC2)nc1"
},
"smiles": "COCc1cnc(N2CCC([C@H]3C[C@H]3CCOc3cc(F)c(CC(=O)N4CCC4)c(F)c3)CC2)nc1",
"reactionStepId": "sa_5f12b0557432957138d07141",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US09018224B2;0632;1610470\",\"rsmi\":\"O[C:24]([CH2:23][c:22]1[c:20]([F:21])[cH:19][c:18]([O:17][CH2:16][CH2:15][C@H:14]2[C@@H:12]([CH:11]3[CH2:10][CH2:9][N:8]([c:7]4[n:6][cH:5][c:4]([CH2:3][O:2][CH3:1])[cH:36][n:35]4)[CH2:34][CH2:33]3)[CH2:13]2)[cH:32][c:30]1[F:31])=[O:25].[NH:26]1[CH2:27][CH2:28][CH2:29]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][O:2][CH2:3][c:4]1[cH:5][n:6][c:7]([N:8]2[CH2:9][CH2:10][CH:11]([C@H:12]3[CH2:13][C@H:14]3[CH2:15][CH2:16][O:17][c:18]3[cH:19][c:20]([F:21])[c:22]([CH2:23][C:24](=[O:25])[N:26]4[CH2:27][CH2:28][CH2:29]4)[c:30]([F:31])[cH:32]3)[CH2:33][CH2:34]2)[n:35][cH:36]1\"},\"mapped_reaction_smiles\":\"O[C:24]([CH2:23][c:22]1[c:20]([F:21])[cH:19][c:18]([O:17][CH2:16][CH2:15][C@H:14]2[C@@H:12]([CH:11]3[CH2:10][CH2:9][N:8]([c:7]4[n:6][cH:5][c:4]([CH2:3][O:2][CH3:1])[cH:36][n:35]4)[CH2:34][CH2:33]3)[CH2:13]2)[cH:32][c:30]1[F:31])=[O:25].[NH:26]1[CH2:27][CH2:28][CH2:29]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][O:2][CH2:3][c:4]1[cH:5][n:6][c:7]([N:8]2[CH2:9][CH2:10][CH:11]([C@H:12]3[CH2:13][C@H:14]3[CH2:15][CH2:16][O:17][c:18]3[cH:19][c:20]([F:21])[c:22]([CH2:23][C:24](=[O:25])[N:26]4[CH2:27][CH2:28][CH2:29]4)[c:30]([F:31])[cH:32]3)[CH2:33][CH2:34]2)[n:35][cH:36]1\"}",
"reactionStep": {
"id": "sa_5f12b0557432957138d07141",
"reactionHash": "c7c8f0264f0bc2736f2fcf73ba27f0f89ae23f12a76537e175e8d0d44f365f7a"
},
"children": [
{
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"routeId": "sa_1f100147fcfa468df895ddbd",
"moleculeId": "sa_39fa88dc9a66624f459001f0",
"parentId": "11211",
"isLeaf": false,
"molecule": {
"id": "sa_39fa88dc9a66624f459001f0",
"inchikey": "FYUWHFLTHCZHGA-IEBWSBKVSA-N",
"smiles": "COCc1cnc(N2CCC([C@H]3C[C@H]3CCOc3cc(F)c(CC(=O)O)c(F)c3)CC2)nc1"
},
"smiles": "COCc1cnc(N2CCC([C@H]3C[C@H]3CCOc3cc(F)c(CC(=O)O)c(F)c3)CC2)nc1",
"reactionStepId": "sa_53164cc14b375f823ea632b1",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US09018224B2;0628;1610468\",\"rsmi\":\"C[O:26][C:24]([CH2:23][c:22]1[c:20]([F:21])[cH:19][c:18]([O:17][CH2:16][CH2:15][C@H:14]2[C@@H:12]([CH:11]3[CH2:10][CH2:9][N:8]([c:7]4[n:6][cH:5][c:4]([CH2:3][O:2][CH3:1])[cH:33][n:32]4)[CH2:31][CH2:30]3)[CH2:13]2)[cH:29][c:27]1[F:28])=[O:25]>C1CCOC1.CO.Cl.O.[Na+].O>[CH3:1][O:2][CH2:3][c:4]1[cH:5][n:6][c:7]([N:8]2[CH2:9][CH2:10][CH:11]([C@H:12]3[CH2:13][C@H:14]3[CH2:15][CH2:16][O:17][c:18]3[cH:19][c:20]([F:21])[c:22]([CH2:23][C:24](=[O:25])[OH:26])[c:27]([F:28])[cH:29]3)[CH2:30][CH2:31]2)[n:32][cH:33]1\"},\"mapped_reaction_smiles\":\"C[O:26][C:24]([CH2:23][c:22]1[c:20]([F:21])[cH:19][c:18]([O:17][CH2:16][CH2:15][C@H:14]2[C@@H:12]([CH:11]3[CH2:10][CH2:9][N:8]([c:7]4[n:6][cH:5][c:4]([CH2:3][O:2][CH3:1])[cH:33][n:32]4)[CH2:31][CH2:30]3)[CH2:13]2)[cH:29][c:27]1[F:28])=[O:25]>C1CCOC1.CO.Cl.O.[Na+].O>[CH3:1][O:2][CH2:3][c:4]1[cH:5][n:6][c:7]([N:8]2[CH2:9][CH2:10][CH:11]([C@H:12]3[CH2:13][C@H:14]3[CH2:15][CH2:16][O:17][c:18]3[cH:19][c:20]([F:21])[c:22]([CH2:23][C:24](=[O:25])[OH:26])[c:27]([F:28])[cH:29]3)[CH2:30][CH2:31]2)[n:32][cH:33]1\"}",
"reactionStep": {
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"reactionHash": "4ac0d835875bd00c11695c7f5ecefce7c669a606cecf82572644ce5f89428941"
},
"children": [
{
"id": "11213",
"routeId": "sa_1f100147fcfa468df895ddbd",
"moleculeId": "sa_3690e19515329d6ef01b5744",
"parentId": "11212",
"isLeaf": false,
"molecule": {
"id": "sa_3690e19515329d6ef01b5744",
"inchikey": "FGFBKKGEOAPMMG-UYAOXDASSA-N",
"smiles": "COCc1cnc(N2CCC([C@H]3C[C@H]3CCOc3cc(F)c(CC(=O)OC)c(F)c3)CC2)nc1"
},
"smiles": "COCc1cnc(N2CCC([C@H]3C[C@H]3CCOc3cc(F)c(CC(=O)OC)c(F)c3)CC2)nc1",
"reactionStepId": "sa_f2e06dddbd7f252112980acd",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US09018224B2;0626;1610467\",\"rsmi\":\"O[c:18]1[cH:19][c:20]([F:21])[c:22]([CH2:23][C:24](=[O:25])[O:26][CH3:27])[c:28]([F:29])[cH:30]1.[CH3:1][O:2][CH2:3][c:4]1[cH:5][n:6][c:7]([N:8]2[CH2:9][CH2:10][CH:11]([C@H:12]3[CH2:13][C@H:14]3[CH2:15][CH2:16][OH:17])[CH2:31][CH2:32]2)[n:33][cH:34]1>CC(C)(C)OC(=O)N=NC(=O)OC(C)(C)C.ClCCl.c1ccc(P(c2ccccc2)c2ccccc2)cc1>[CH3:1][O:2][CH2:3][c:4]1[cH:5][n:6][c:7]([N:8]2[CH2:9][CH2:10][CH:11]([C@H:12]3[CH2:13][C@H:14]3[CH2:15][CH2:16][O:17][c:18]3[cH:19][c:20]([F:21])[c:22]([CH2:23][C:24](=[O:25])[O:26][CH3:27])[c:28]([F:29])[cH:30]3)[CH2:31][CH2:32]2)[n:33][cH:34]1\"},\"mapped_reaction_smiles\":\"O[c:18]1[cH:19][c:20]([F:21])[c:22]([CH2:23][C:24](=[O:25])[O:26][CH3:27])[c:28]([F:29])[cH:30]1.[CH3:1][O:2][CH2:3][c:4]1[cH:5][n:6][c:7]([N:8]2[CH2:9][CH2:10][CH:11]([C@H:12]3[CH2:13][C@H:14]3[CH2:15][CH2:16][OH:17])[CH2:31][CH2:32]2)[n:33][cH:34]1>CC(C)(C)OC(=O)N=NC(=O)OC(C)(C)C.ClCCl.c1ccc(P(c2ccccc2)c2ccccc2)cc1>[CH3:1][O:2][CH2:3][c:4]1[cH:5][n:6][c:7]([N:8]2[CH2:9][CH2:10][CH:11]([C@H:12]3[CH2:13][C@H:14]3[CH2:15][CH2:16][O:17][c:18]3[cH:19][c:20]([F:21])[c:22]([CH2:23][C:24](=[O:25])[O:26][CH3:27])[c:28]([F:29])[cH:30]3)[CH2:31][CH2:32]2)[n:33][cH:34]1\"}",
"reactionStep": {
"id": "sa_f2e06dddbd7f252112980acd",
"reactionHash": "457b4d6ac2b539c8f00f1034f22bd014b2aee013ada6d3ab0c788a6801db2a01"
},
"children": [
{
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"routeId": "sa_1f100147fcfa468df895ddbd",
"moleculeId": "sa_2eeee2f59830fd18e0bbe105",
"parentId": "11213",
"isLeaf": false,
"molecule": {
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"inchikey": "CSNRCKXGQZGHPZ-HUUCEWRRSA-N",
"smiles": "COCc1cnc(N2CCC([C@H]3C[C@H]3CCO)CC2)nc1"
},
"smiles": "COCc1cnc(N2CCC([C@H]3C[C@H]3CCO)CC2)nc1",
"reactionStepId": "sa_ea933048522847a1637709c0",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US09018224B2;0434;1610402\",\"rsmi\":\"Cl[c:7]1[n:6][cH:5][c:4]([CH2:3][O:2][CH3:1])[cH:21][n:20]1.[NH:8]1[CH2:9][CH2:10][CH:11]([C@H:12]2[CH2:13][C@H:14]2[CH2:15][CH2:16][OH:17])[CH2:18][CH2:19]1>CN(C)C=O.O.O=C(O)O.Cl.[K+].[K+].[Na+]>[CH3:1][O:2][CH2:3][c:4]1[cH:5][n:6][c:7]([N:8]2[CH2:9][CH2:10][CH:11]([C@H:12]3[CH2:13][C@H:14]3[CH2:15][CH2:16][OH:17])[CH2:18][CH2:19]2)[n:20][cH:21]1\"},\"mapped_reaction_smiles\":\"Cl[c:7]1[n:6][cH:5][c:4]([CH2:3][O:2][CH3:1])[cH:21][n:20]1.[NH:8]1[CH2:9][CH2:10][CH:11]([C@H:12]2[CH2:13][C@H:14]2[CH2:15][CH2:16][OH:17])[CH2:18][CH2:19]1>CN(C)C=O.O.O=C(O)O.Cl.[K+].[K+].[Na+]>[CH3:1][O:2][CH2:3][c:4]1[cH:5][n:6][c:7]([N:8]2[CH2:9][CH2:10][CH:11]([C@H:12]3[CH2:13][C@H:14]3[CH2:15][CH2:16][OH:17])[CH2:18][CH2:19]2)[n:20][cH:21]1\"}",
"reactionStep": {
"id": "sa_ea933048522847a1637709c0",
"reactionHash": "3e65fe6e2024f786b8329793e34aff684fa6aeaf47798c9bea0502ffd9c59683"
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"children": [
{
"id": "11215",
"routeId": "sa_1f100147fcfa468df895ddbd",
"moleculeId": "sa_6b16a91fac97234af1e97ecf",
"parentId": "11214",
"isLeaf": false,
"molecule": {
"id": "sa_6b16a91fac97234af1e97ecf",
"inchikey": "UNTRGRONESWNJV-UHFFFAOYSA-N",
"smiles": "COCc1cnc(Cl)nc1"
},
"smiles": "COCc1cnc(Cl)nc1",
"reactionStepId": "sa_3bf36edd82947770407b2d7c",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US09018224B2;0432;1610401\",\"rsmi\":\"I[CH3:1].[OH:2][CH2:3][c:4]1[cH:5][n:6][c:7]([Cl:8])[n:9][cH:10]1>CN(C)C=O.[HH].[Na+]>[CH3:1][O:2][CH2:3][c:4]1[cH:5][n:6][c:7]([Cl:8])[n:9][cH:10]1\"},\"mapped_reaction_smiles\":\"I[CH3:1].[OH:2][CH2:3][c:4]1[cH:5][n:6][c:7]([Cl:8])[n:9][cH:10]1>CN(C)C=O.[HH].[Na+]>[CH3:1][O:2][CH2:3][c:4]1[cH:5][n:6][c:7]([Cl:8])[n:9][cH:10]1\"}",
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"children": [
{
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"molecule": {
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"inchikey": "INQOMBQAUSQDDS-UHFFFAOYSA-N",
"smiles": "CI"
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"smiles": "CI",
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{
"id": "11217",
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"moleculeId": "sa_d8ae1a03faa397a408f276dc",
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"molecule": {
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"inchikey": "OHMILAMAADHENX-UHFFFAOYSA-N",
"smiles": "OCc1cnc(Cl)nc1"
},
"smiles": "OCc1cnc(Cl)nc1",
"reactionStepId": null,
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}
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},
{
"id": "11218",
"routeId": "sa_1f100147fcfa468df895ddbd",
"moleculeId": "sa_23a8abf0e2fdbc35e1e3f6a9",
"parentId": "11214",
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"molecule": {
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"inchikey": "VYNIUPMZSJSTBI-NXEZZACHSA-N",
"smiles": "OCC[C@@H]1C[C@@H]1C1CCNCC1"
},
"smiles": "OCC[C@@H]1C[C@@H]1C1CCNCC1",
"reactionStepId": "sa_1bb9f2e64299fae6fee4c82f",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US09018224B2;0423;1610399\",\"rsmi\":\"O=C(OCc1ccccc1)[N:10]1[CH2:9][CH2:8][CH:7]([C@@H:6]2[C@H:4]([CH2:3][CH2:2][OH:1])[CH2:5]2)[CH2:12][CH2:11]1>CO.[Pd]>[OH:1][CH2:2][CH2:3][C@@H:4]1[CH2:5][C@@H:6]1[CH:7]1[CH2:8][CH2:9][NH:10][CH2:11][CH2:12]1\"},\"mapped_reaction_smiles\":\"O=C(OCc1ccccc1)[N:10]1[CH2:9][CH2:8][CH:7]([C@@H:6]2[C@H:4]([CH2:3][CH2:2][OH:1])[CH2:5]2)[CH2:12][CH2:11]1>CO.[Pd]>[OH:1][CH2:2][CH2:3][C@@H:4]1[CH2:5][C@@H:6]1[CH:7]1[CH2:8][CH2:9][NH:10][CH2:11][CH2:12]1\"}",
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"children": [
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},
"smiles": "O=C(OCc1ccccc1)N1CCC([C@H]2C[C@H]2CCO)CC1",
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},
{
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"molecule": {
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"inchikey": "RWKJGEWDDSYYBK-UHFFFAOYSA-N",
"smiles": "COC(=O)Cc1c(F)cc(O)cc1F"
},
"smiles": "COC(=O)Cc1c(F)cc(O)cc1F",
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]
},
{
"id": "11221",
"routeId": "sa_1f100147fcfa468df895ddbd",
"moleculeId": "sa_3edf2a7ec025f1195f3401ef",
"parentId": "11211",
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"molecule": {
"id": "sa_3edf2a7ec025f1195f3401ef",
"inchikey": "HONIICLYMWZJFZ-UHFFFAOYSA-N",
"smiles": "C1CNC1"
},
"smiles": "C1CNC1",
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"children": []
}
]
}
}