Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
COc1cnc(Nc2cnc(Cl)c(N)c2)c(-c2nc(C)nc(N)n2)c1
InChiKey
VXIFMJZIIDYJBM-UHFFFAOYSA-N
Route Signature
240f27300fe31363b1d6eb431ffe96581f7934f5b4824740eab061940b991943
Synthesis route with 5 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_a2356f08d7e87c91bbe24bac",
"signature": "240f27300fe31363b1d6eb431ffe96581f7934f5b4824740eab061940b991943",
"contentHash": "96884e6a02c52c3ef9963fae95f799bbd327fdb54a48b09fc7b8c6afaba40b42",
"length": 5,
"isConvergent": true
},
"target": {
"id": "sa_6fc5908b7a17a2556ca090b7",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-00120",
"moleculeId": "sa_898d1af74c038ff9296f7ba2",
"smiles": "COc1cnc(Nc2cnc(Cl)c(N)c2)c(-c2nc(C)nc(N)n2)c1",
"routeLength": 5,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_898d1af74c038ff9296f7ba2",
"inchikey": "VXIFMJZIIDYJBM-UHFFFAOYSA-N",
"smiles": "COc1cnc(Nc2cnc(Cl)c(N)c2)c(-c2nc(C)nc(N)n2)c1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "9194",
"routeId": "sa_a2356f08d7e87c91bbe24bac",
"moleculeId": "sa_898d1af74c038ff9296f7ba2",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_898d1af74c038ff9296f7ba2",
"inchikey": "VXIFMJZIIDYJBM-UHFFFAOYSA-N",
"smiles": "COc1cnc(Nc2cnc(Cl)c(N)c2)c(-c2nc(C)nc(N)n2)c1"
},
"smiles": "COc1cnc(Nc2cnc(Cl)c(N)c2)c(-c2nc(C)nc(N)n2)c1",
"reactionStepId": "sa_5af25d91047cd43937175c7a",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100273764A1;1862;966524\",\"rsmi\":\"CC(C)(C)OC(=O)[NH:14][c:13]1[c:11]([Cl:12])[n:10][cH:9][c:8]([NH:7][c:6]2[n:5][cH:4][c:3]([O:2][CH3:1])[cH:25][c:16]2-[c:17]2[n:18][c:19]([CH3:20])[n:21][c:22]([NH2:23])[n:24]2)[cH:15]1>ClCCl.O=C(O)C(F)(F)F.O=C(O)O.[Na+]>[CH3:1][O:2][c:3]1[cH:4][n:5][c:6]([NH:7][c:8]2[cH:9][n:10][c:11]([Cl:12])[c:13]([NH2:14])[cH:15]2)[c:16](-[c:17]2[n:18][c:19]([CH3:20])[n:21][c:22]([NH2:23])[n:24]2)[cH:25]1\"},\"mapped_reaction_smiles\":\"CC(C)(C)OC(=O)[NH:14][c:13]1[c:11]([Cl:12])[n:10][cH:9][c:8]([NH:7][c:6]2[n:5][cH:4][c:3]([O:2][CH3:1])[cH:25][c:16]2-[c:17]2[n:18][c:19]([CH3:20])[n:21][c:22]([NH2:23])[n:24]2)[cH:15]1>ClCCl.O=C(O)C(F)(F)F.O=C(O)O.[Na+]>[CH3:1][O:2][c:3]1[cH:4][n:5][c:6]([NH:7][c:8]2[cH:9][n:10][c:11]([Cl:12])[c:13]([NH2:14])[cH:15]2)[c:16](-[c:17]2[n:18][c:19]([CH3:20])[n:21][c:22]([NH2:23])[n:24]2)[cH:25]1\"}",
"reactionStep": {
"id": "sa_5af25d91047cd43937175c7a",
"reactionHash": "dc6325eb25494f301c0ecbdeae1e39e573a6199f517518eca03d9ca4c2682073"
},
"children": [
{
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"routeId": "sa_a2356f08d7e87c91bbe24bac",
"moleculeId": "sa_ba968ddd27b5cbfe60d5cdae",
"parentId": "9194",
"isLeaf": false,
"molecule": {
"id": "sa_ba968ddd27b5cbfe60d5cdae",
"inchikey": "LDUYCOHSVPPPES-UHFFFAOYSA-N",
"smiles": "COc1cnc(Nc2cnc(Cl)c(NC(=O)OC(C)(C)C)c2)c(-c2nc(C)nc(N)n2)c1"
},
"smiles": "COc1cnc(Nc2cnc(Cl)c(NC(=O)OC(C)(C)C)c2)c(-c2nc(C)nc(N)n2)c1",
"reactionStepId": "sa_787febfd36a8d9591fa35e35",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100273764A1;1861;966523\",\"rsmi\":\"F[c:6]1[n:5][cH:4][c:3]([O:2][CH3:1])[cH:32][c:23]1-[c:24]1[n:25][c:26]([CH3:27])[n:28][c:29]([NH2:30])[n:31]1.[NH2:7][c:8]1[cH:9][n:10][c:11]([Cl:12])[c:13]([NH:14][C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21])[cH:22]1>C1CCOC1.CN(C)C=O.C[Si](C)(C)N[Si](C)(C)C.Cl.N.[Na+]>[CH3:1][O:2][c:3]1[cH:4][n:5][c:6]([NH:7][c:8]2[cH:9][n:10][c:11]([Cl:12])[c:13]([NH:14][C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21])[cH:22]2)[c:23](-[c:24]2[n:25][c:26]([CH3:27])[n:28][c:29]([NH2:30])[n:31]2)[cH:32]1\"},\"mapped_reaction_smiles\":\"F[c:6]1[n:5][cH:4][c:3]([O:2][CH3:1])[cH:32][c:23]1-[c:24]1[n:25][c:26]([CH3:27])[n:28][c:29]([NH2:30])[n:31]1.[NH2:7][c:8]1[cH:9][n:10][c:11]([Cl:12])[c:13]([NH:14][C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21])[cH:22]1>C1CCOC1.CN(C)C=O.C[Si](C)(C)N[Si](C)(C)C.Cl.N.[Na+]>[CH3:1][O:2][c:3]1[cH:4][n:5][c:6]([NH:7][c:8]2[cH:9][n:10][c:11]([Cl:12])[c:13]([NH:14][C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21])[cH:22]2)[c:23](-[c:24]2[n:25][c:26]([CH3:27])[n:28][c:29]([NH2:30])[n:31]2)[cH:32]1\"}",
"reactionStep": {
"id": "sa_787febfd36a8d9591fa35e35",
"reactionHash": "761d17ddceda31a0215f71875e46b3f1194bd903644d96cbb20336f3bb6a27f9"
},
"children": [
{
"id": "9196",
"routeId": "sa_a2356f08d7e87c91bbe24bac",
"moleculeId": "sa_ac065bafa8146c1549d6e189",
"parentId": "9195",
"isLeaf": false,
"molecule": {
"id": "sa_ac065bafa8146c1549d6e189",
"inchikey": "AMDHVMMANJYGIT-UHFFFAOYSA-N",
"smiles": "COc1cnc(F)c(-c2nc(C)nc(N)n2)c1"
},
"smiles": "COc1cnc(F)c(-c2nc(C)nc(N)n2)c1",
"reactionStepId": "sa_e870c90657feb1ead2502c02",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100273764A1;1725;966456\",\"rsmi\":\"Cl[c:9]1[n:10][c:11]([NH2:12])[n:13][c:14]([CH3:15])[n:16]1.OB(O)[c:8]1[c:6]([F:7])[n:5][cH:4][c:3]([O:2][CH3:1])[cH:17]1>CC(=O)O.CCO.O.[K+]>[CH3:1][O:2][c:3]1[cH:4][n:5][c:6]([F:7])[c:8](-[c:9]2[n:10][c:11]([NH2:12])[n:13][c:14]([CH3:15])[n:16]2)[cH:17]1\"},\"mapped_reaction_smiles\":\"Cl[c:9]1[n:10][c:11]([NH2:12])[n:13][c:14]([CH3:15])[n:16]1.OB(O)[c:8]1[c:6]([F:7])[n:5][cH:4][c:3]([O:2][CH3:1])[cH:17]1>CC(=O)O.CCO.O.[K+]>[CH3:1][O:2][c:3]1[cH:4][n:5][c:6]([F:7])[c:8](-[c:9]2[n:10][c:11]([NH2:12])[n:13][c:14]([CH3:15])[n:16]2)[cH:17]1\"}",
"reactionStep": {
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"reactionHash": "8cd4b4d3c535d3763662a7a7fba922bee8f7d45aa854a2564bb071a65fd0429d"
},
"children": [
{
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"routeId": "sa_a2356f08d7e87c91bbe24bac",
"moleculeId": "sa_69872c104af81b6f672f8e25",
"parentId": "9196",
"isLeaf": false,
"molecule": {
"id": "sa_69872c104af81b6f672f8e25",
"inchikey": "BTBXQZKDOSYRDX-UHFFFAOYSA-N",
"smiles": "Cc1nc(N)nc(Cl)n1"
},
"smiles": "Cc1nc(N)nc(Cl)n1",
"reactionStepId": "sa_f5d8636c5e5737c075b89c16",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100273764A1;0644;965883\",\"rsmi\":\"Cl[c:7]1[n:6][c:4]([Cl:5])[n:3][c:2]([CH3:1])[n:9]1.[NH3:8]>CO.Cc1ccccc1>[CH3:1][c:2]1[n:3][c:4]([Cl:5])[n:6][c:7]([NH2:8])[n:9]1\"},\"mapped_reaction_smiles\":\"Cl[c:7]1[n:6][c:4]([Cl:5])[n:3][c:2]([CH3:1])[n:9]1.[NH3:8]>CO.Cc1ccccc1>[CH3:1][c:2]1[n:3][c:4]([Cl:5])[n:6][c:7]([NH2:8])[n:9]1\"}",
"reactionStep": {
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"reactionHash": "8d09832af8c64355a497e4f7289bc2526dab267d1e6ca5cb98a00430727c7cdb"
},
"children": [
{
"id": "9198",
"routeId": "sa_a2356f08d7e87c91bbe24bac",
"moleculeId": "sa_758c9f5889571f976cfc9763",
"parentId": "9197",
"isLeaf": true,
"molecule": {
"id": "sa_758c9f5889571f976cfc9763",
"inchikey": "BFUGAHPTVMZLAC-UHFFFAOYSA-N",
"smiles": "Cc1nc(Cl)nc(Cl)n1"
},
"smiles": "Cc1nc(Cl)nc(Cl)n1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "9199",
"routeId": "sa_a2356f08d7e87c91bbe24bac",
"moleculeId": "sa_c9679fdd876f32f86b77fb69",
"parentId": "9197",
"isLeaf": true,
"molecule": {
"id": "sa_c9679fdd876f32f86b77fb69",
"inchikey": "QGZKDVFQNNGYKY-UHFFFAOYSA-N",
"smiles": "N"
},
"smiles": "N",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "9200",
"routeId": "sa_a2356f08d7e87c91bbe24bac",
"moleculeId": "sa_d9f964c8987890c97cfb208b",
"parentId": "9196",
"isLeaf": false,
"molecule": {
"id": "sa_d9f964c8987890c97cfb208b",
"inchikey": "GUGFLRVPERPDJR-UHFFFAOYSA-N",
"smiles": "COc1cnc(F)c(B(O)O)c1"
},
"smiles": "COc1cnc(F)c(B(O)O)c1",
"reactionStepId": "sa_34b5d9ebec11810b0ab1acb4",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100273764A1;1724;966455\",\"rsmi\":\"CC(C)O[B:9]([O:10]C(C)C)[O:11]C(C)C.[CH3:1][O:2][c:3]1[cH:4][n:5][c:6]([F:7])[cH:8][cH:12]1>C1CCOC1.CC(C)NC(C)C.[Li]CCCC>[CH3:1][O:2][c:3]1[cH:4][n:5][c:6]([F:7])[c:8]([B:9]([OH:10])[OH:11])[cH:12]1\"},\"mapped_reaction_smiles\":\"CC(C)O[B:9]([O:10]C(C)C)[O:11]C(C)C.[CH3:1][O:2][c:3]1[cH:4][n:5][c:6]([F:7])[cH:8][cH:12]1>C1CCOC1.CC(C)NC(C)C.[Li]CCCC>[CH3:1][O:2][c:3]1[cH:4][n:5][c:6]([F:7])[c:8]([B:9]([OH:10])[OH:11])[cH:12]1\"}",
"reactionStep": {
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"reactionHash": "ebe6ac4c5dbc7ee09fd6fbdf36564c8a9b9d2677ddd070d6764d60118607663b"
},
"children": [
{
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"routeId": "sa_a2356f08d7e87c91bbe24bac",
"moleculeId": "sa_a7044bedc5238cc8f8e5b82f",
"parentId": "9200",
"isLeaf": false,
"molecule": {
"id": "sa_a7044bedc5238cc8f8e5b82f",
"inchikey": "KSZQZUAJEWXGQM-UHFFFAOYSA-N",
"smiles": "COc1ccc(F)nc1"
},
"smiles": "COc1ccc(F)nc1",
"reactionStepId": "sa_55daec5a5e1d757ddae382d3",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100273764A1;1723;966454\",\"rsmi\":\"I[CH3:1].[OH:2][c:3]1[cH:4][n:5][c:6]([F:7])[cH:8][cH:9]1>CN(C)C=O.O.O=C(O)O.[K+].[K+]>[CH3:1][O:2][c:3]1[cH:4][n:5][c:6]([F:7])[cH:8][cH:9]1\"},\"mapped_reaction_smiles\":\"I[CH3:1].[OH:2][c:3]1[cH:4][n:5][c:6]([F:7])[cH:8][cH:9]1>CN(C)C=O.O.O=C(O)O.[K+].[K+]>[CH3:1][O:2][c:3]1[cH:4][n:5][c:6]([F:7])[cH:8][cH:9]1\"}",
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"molecule": {
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"inchikey": "HTRLNWYWOKWCLV-UHFFFAOYSA-N",
"smiles": "Oc1ccc(F)nc1"
},
"smiles": "Oc1ccc(F)nc1",
"reactionStepId": null,
"template": null,
"metadata": null,
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{
"id": "9203",
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"molecule": {
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"inchikey": "INQOMBQAUSQDDS-UHFFFAOYSA-N",
"smiles": "CI"
},
"smiles": "CI",
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}
]
},
{
"id": "9204",
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"parentId": "9200",
"isLeaf": true,
"molecule": {
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"inchikey": "NHDIQVFFNDKAQU-UHFFFAOYSA-N",
"smiles": "CC(C)OB(OC(C)C)OC(C)C"
},
"smiles": "CC(C)OB(OC(C)C)OC(C)C",
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},
{
"id": "9205",
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"molecule": {
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"inchikey": "SLSLMWRTLJXNLE-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)Nc1cc(N)cnc1Cl"
},
"smiles": "CC(C)(C)OC(=O)Nc1cc(N)cnc1Cl",
"reactionStepId": "sa_389d1ac070e497e79b5874b4",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100273764A1;1860;966522\",\"rsmi\":\"c1ccc(C(c2ccccc2)=[N:12][c:11]2[cH:10][c:9]([NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[c:15]([Cl:16])[n:14][cH:13]2)cc1>C1CCOC1.Cl>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][c:9]1[cH:10][c:11]([NH2:12])[cH:13][n:14][c:15]1[Cl:16]\"},\"mapped_reaction_smiles\":\"c1ccc(C(c2ccccc2)=[N:12][c:11]2[cH:10][c:9]([NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[c:15]([Cl:16])[n:14][cH:13]2)cc1>C1CCOC1.Cl>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][c:9]1[cH:10][c:11]([NH2:12])[cH:13][n:14][c:15]1[Cl:16]\"}",
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{
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"smiles": "CC(C)(C)OC(=O)Nc1cc(N=C(c2ccccc2)c2ccccc2)cnc1Cl"
},
"smiles": "CC(C)(C)OC(=O)Nc1cc(N=C(c2ccccc2)c2ccccc2)cnc1Cl",
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}
]
}
]
}
]
}
}