Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
NC(=O)c1sc2nc(NC3CC3)nc(-c3cccc(NC(=O)Nc4ccc(C(F)(F)F)cc4)c3)c2c1N
InChiKey
RVPNRQPMZBNTBC-UHFFFAOYSA-N
Route Signature
5ff3d91171af2a0e388cd9629f20bc3bcf794ee5334a0ac5975f3846a2a853cd
Synthesis route with 5 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_d79427abf3c3d2c33289aeba",
"signature": "5ff3d91171af2a0e388cd9629f20bc3bcf794ee5334a0ac5975f3846a2a853cd",
"contentHash": "b19074c0a867050adae98f497bbe9b4015e82f9bd05542a93a6128fee5c5aed8",
"length": 5,
"isConvergent": false
},
"target": {
"id": "sa_d7bd91cced7ae207817f5662",
"benchmarkSetId": "61e696668b63e77d7c2a29c0821768e1c383de8313852d6e995224859494442e",
"targetId": "n5-01242",
"moleculeId": "sa_ea2c3b554789929a6353fd1f",
"smiles": "NC(=O)c1sc2nc(NC3CC3)nc(-c3cccc(NC(=O)Nc4ccc(C(F)(F)F)cc4)c3)c2c1N",
"routeLength": 5,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_ea2c3b554789929a6353fd1f",
"inchikey": "RVPNRQPMZBNTBC-UHFFFAOYSA-N",
"smiles": "NC(=O)c1sc2nc(NC3CC3)nc(-c3cccc(NC(=O)Nc4ccc(C(F)(F)F)cc4)c3)c2c1N"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "14163",
"routeId": "sa_d79427abf3c3d2c33289aeba",
"moleculeId": "sa_ea2c3b554789929a6353fd1f",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_ea2c3b554789929a6353fd1f",
"inchikey": "RVPNRQPMZBNTBC-UHFFFAOYSA-N",
"smiles": "NC(=O)c1sc2nc(NC3CC3)nc(-c3cccc(NC(=O)Nc4ccc(C(F)(F)F)cc4)c3)c2c1N"
},
"smiles": "NC(=O)c1sc2nc(NC3CC3)nc(-c3cccc(NC(=O)Nc4ccc(C(F)(F)F)cc4)c3)c2c1N",
"reactionStepId": "sa_e0a5b6507ae0582d565ea4ba",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20080004271A1;0749;533212\",\"rsmi\":\"[C:21](=[O:22])=[N:23][c:24]1[cH:25][cH:26][c:27]([C:28]([F:29])([F:30])[F:31])[cH:32][cH:33]1.[NH2:1][C:2](=[O:3])[c:4]1[c:5]([NH2:6])[c:7]2[c:8]([n:9][c:10]([NH:11][CH:12]3[CH2:13][CH2:14]3)[n:15][c:16]2-[c:17]2[cH:18][c:19]([NH2:20])[cH:34][cH:35][cH:36]2)[s:37]1>C1CCOC1>[NH2:1][C:2](=[O:3])[c:4]1[c:5]([NH2:6])[c:7]2[c:8]([n:9][c:10]([NH:11][CH:12]3[CH2:13][CH2:14]3)[n:15][c:16]2-[c:17]2[cH:18][c:19]([NH:20][C:21](=[O:22])[NH:23][c:24]3[cH:25][cH:26][c:27]([C:28]([F:29])([F:30])[F:31])[cH:32][cH:33]3)[cH:34][cH:35][cH:36]2)[s:37]1\"},\"mapped_reaction_smiles\":\"[C:21](=[O:22])=[N:23][c:24]1[cH:25][cH:26][c:27]([C:28]([F:29])([F:30])[F:31])[cH:32][cH:33]1.[NH2:1][C:2](=[O:3])[c:4]1[c:5]([NH2:6])[c:7]2[c:8]([n:9][c:10]([NH:11][CH:12]3[CH2:13][CH2:14]3)[n:15][c:16]2-[c:17]2[cH:18][c:19]([NH2:20])[cH:34][cH:35][cH:36]2)[s:37]1>C1CCOC1>[NH2:1][C:2](=[O:3])[c:4]1[c:5]([NH2:6])[c:7]2[c:8]([n:9][c:10]([NH:11][CH:12]3[CH2:13][CH2:14]3)[n:15][c:16]2-[c:17]2[cH:18][c:19]([NH:20][C:21](=[O:22])[NH:23][c:24]3[cH:25][cH:26][c:27]([C:28]([F:29])([F:30])[F:31])[cH:32][cH:33]3)[cH:34][cH:35][cH:36]2)[s:37]1\"}",
"reactionStep": {
"id": "sa_e0a5b6507ae0582d565ea4ba",
"reactionHash": "d2d6fc8698ebc467d4b39293085e8bd7ceed717a621037cfffca1b01d605447e"
},
"children": [
{
"id": "14164",
"routeId": "sa_d79427abf3c3d2c33289aeba",
"moleculeId": "sa_889dd8d06b3deee05da7e6c1",
"parentId": "14163",
"isLeaf": false,
"molecule": {
"id": "sa_889dd8d06b3deee05da7e6c1",
"inchikey": "JUNUOUUZHDRSEL-UHFFFAOYSA-N",
"smiles": "NC(=O)c1sc2nc(NC3CC3)nc(-c3cccc(N)c3)c2c1N"
},
"smiles": "NC(=O)c1sc2nc(NC3CC3)nc(-c3cccc(N)c3)c2c1N",
"reactionStepId": "sa_58bda4c9797ce96b26ec73a4",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20080004271A1;0739;533207\",\"rsmi\":\"O=[N+:20]([O-])[c:19]1[cH:18][c:17](-[c:16]2[c:7]3[c:5]([NH2:6])[c:4]([C:2]([NH2:1])=[O:3])[s:24][c:8]3[n:9][c:10]([NH:11][CH:12]3[CH2:13][CH2:14]3)[n:15]2)[cH:23][cH:22][cH:21]1>CCO.CCOC(C)=O.[H][H].[Pd]>[NH2:1][C:2](=[O:3])[c:4]1[c:5]([NH2:6])[c:7]2[c:8]([n:9][c:10]([NH:11][CH:12]3[CH2:13][CH2:14]3)[n:15][c:16]2-[c:17]2[cH:18][c:19]([NH2:20])[cH:21][cH:22][cH:23]2)[s:24]1\"},\"mapped_reaction_smiles\":\"O=[N+:20]([O-])[c:19]1[cH:18][c:17](-[c:16]2[c:7]3[c:5]([NH2:6])[c:4]([C:2]([NH2:1])=[O:3])[s:24][c:8]3[n:9][c:10]([NH:11][CH:12]3[CH2:13][CH2:14]3)[n:15]2)[cH:23][cH:22][cH:21]1>CCO.CCOC(C)=O.[H][H].[Pd]>[NH2:1][C:2](=[O:3])[c:4]1[c:5]([NH2:6])[c:7]2[c:8]([n:9][c:10]([NH:11][CH:12]3[CH2:13][CH2:14]3)[n:15][c:16]2-[c:17]2[cH:18][c:19]([NH2:20])[cH:21][cH:22][cH:23]2)[s:24]1\"}",
"reactionStep": {
"id": "sa_58bda4c9797ce96b26ec73a4",
"reactionHash": "8dcf78f0ac231c1f46d2815e5cb1cf97c945e3c5fb270fd0f8757b976c82f234"
},
"children": [
{
"id": "14165",
"routeId": "sa_d79427abf3c3d2c33289aeba",
"moleculeId": "sa_9f27de0b8c17b63e5d3021da",
"parentId": "14164",
"isLeaf": false,
"molecule": {
"id": "sa_9f27de0b8c17b63e5d3021da",
"inchikey": "AEIFIALJRHSPPA-UHFFFAOYSA-N",
"smiles": "NC(=O)c1sc2nc(NC3CC3)nc(-c3cccc([N+](=O)[O-])c3)c2c1N"
},
"smiles": "NC(=O)c1sc2nc(NC3CC3)nc(-c3cccc([N+](=O)[O-])c3)c2c1N",
"reactionStepId": "sa_9ba2ac5f62b2b7a6287d18c3",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20080004271A1;0737;533206\",\"rsmi\":\"[NH2:1][C:2](=[O:3])[CH2:4][S:26][c:8]1[c:7]([C:5]#[N:6])[c:16](-[c:17]2[cH:18][c:19]([N+:20](=[O:21])[O-:22])[cH:23][cH:24][cH:25]2)[n:15][c:10]([NH:11][CH:12]2[CH2:13][CH2:14]2)[n:9]1>CCO.CCO.Cl.[Na+]>[NH2:1][C:2](=[O:3])[c:4]1[c:5]([NH2:6])[c:7]2[c:8]([n:9][c:10]([NH:11][CH:12]3[CH2:13][CH2:14]3)[n:15][c:16]2-[c:17]2[cH:18][c:19]([N+:20](=[O:21])[O-:22])[cH:23][cH:24][cH:25]2)[s:26]1\"},\"mapped_reaction_smiles\":\"[NH2:1][C:2](=[O:3])[CH2:4][S:26][c:8]1[c:7]([C:5]#[N:6])[c:16](-[c:17]2[cH:18][c:19]([N+:20](=[O:21])[O-:22])[cH:23][cH:24][cH:25]2)[n:15][c:10]([NH:11][CH:12]2[CH2:13][CH2:14]2)[n:9]1>CCO.CCO.Cl.[Na+]>[NH2:1][C:2](=[O:3])[c:4]1[c:5]([NH2:6])[c:7]2[c:8]([n:9][c:10]([NH:11][CH:12]3[CH2:13][CH2:14]3)[n:15][c:16]2-[c:17]2[cH:18][c:19]([N+:20](=[O:21])[O-:22])[cH:23][cH:24][cH:25]2)[s:26]1\"}",
"reactionStep": {
"id": "sa_9ba2ac5f62b2b7a6287d18c3",
"reactionHash": "f2020d35c2dd12cf442ff6b740cc3daba254e89113ff512c6bf88818738fd463"
},
"children": [
{
"id": "14166",
"routeId": "sa_d79427abf3c3d2c33289aeba",
"moleculeId": "sa_fb146fe4cd9f10cf3d22dfb8",
"parentId": "14165",
"isLeaf": false,
"molecule": {
"id": "sa_fb146fe4cd9f10cf3d22dfb8",
"inchikey": "SMOOGJCUUJPHFB-UHFFFAOYSA-N",
"smiles": "N#Cc1c(SCC(N)=O)nc(NC2CC2)nc1-c1cccc([N+](=O)[O-])c1"
},
"smiles": "N#Cc1c(SCC(N)=O)nc(NC2CC2)nc1-c1cccc([N+](=O)[O-])c1",
"reactionStepId": "sa_b0cae4651a0c7f9966b02681",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20080004271A1;0736;533205\",\"rsmi\":\"Cl[c:21]1[c:3]([C:2]#[N:1])[c:4](-[c:5]2[cH:6][c:7]([N+:8](=[O:9])[O-:10])[cH:11][cH:12][cH:13]2)[n:14][c:15]([NH:16][CH:17]2[CH2:18][CH2:19]2)[n:20]1.[SH:22][CH2:23][C:24]([NH2:25])=[O:26]>CCO.O=C(O)O.[K+].[K+]>[N:1]#[C:2][c:3]1[c:4](-[c:5]2[cH:6][c:7]([N+:8](=[O:9])[O-:10])[cH:11][cH:12][cH:13]2)[n:14][c:15]([NH:16][CH:17]2[CH2:18][CH2:19]2)[n:20][c:21]1[S:22][CH2:23][C:24]([NH2:25])=[O:26]\"},\"mapped_reaction_smiles\":\"Cl[c:21]1[c:3]([C:2]#[N:1])[c:4](-[c:5]2[cH:6][c:7]([N+:8](=[O:9])[O-:10])[cH:11][cH:12][cH:13]2)[n:14][c:15]([NH:16][CH:17]2[CH2:18][CH2:19]2)[n:20]1.[SH:22][CH2:23][C:24]([NH2:25])=[O:26]>CCO.O=C(O)O.[K+].[K+]>[N:1]#[C:2][c:3]1[c:4](-[c:5]2[cH:6][c:7]([N+:8](=[O:9])[O-:10])[cH:11][cH:12][cH:13]2)[n:14][c:15]([NH:16][CH:17]2[CH2:18][CH2:19]2)[n:20][c:21]1[S:22][CH2:23][C:24]([NH2:25])=[O:26]\"}",
"reactionStep": {
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"reactionHash": "fa124373b7346be3b598043d32dd2ca7cc9ab59e4f3af06caff279bef0ce06e4"
},
"children": [
{
"id": "14167",
"routeId": "sa_d79427abf3c3d2c33289aeba",
"moleculeId": "sa_d17e220cbb15a4c3f3638ddf",
"parentId": "14166",
"isLeaf": true,
"molecule": {
"id": "sa_d17e220cbb15a4c3f3638ddf",
"inchikey": "GYXHHICIFZSKKZ-UHFFFAOYSA-N",
"smiles": "N=C(O)CS"
},
"smiles": "NC(=O)CS",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "14168",
"routeId": "sa_d79427abf3c3d2c33289aeba",
"moleculeId": "sa_d95428d04890befc68cd28f9",
"parentId": "14166",
"isLeaf": false,
"molecule": {
"id": "sa_d95428d04890befc68cd28f9",
"inchikey": "INQCNIQUSLFKTK-UHFFFAOYSA-N",
"smiles": "N#Cc1c(Cl)nc(NC2CC2)nc1-c1cccc([N+](=O)[O-])c1"
},
"smiles": "N#Cc1c(Cl)nc(NC2CC2)nc1-c1cccc([N+](=O)[O-])c1",
"reactionStepId": "sa_d6597ba43598c48d2be6e8ce",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20080004271A1;0735;533204\",\"rsmi\":\"O=P(Cl)(Cl)[Cl:22].O[c:21]1[c:3]([C:2]#[N:1])[c:4](-[c:5]2[cH:6][c:7]([N+:8](=[O:9])[O-:10])[cH:11][cH:12][cH:13]2)[n:14][c:15]([NH:16][CH:17]2[CH2:18][CH2:19]2)[n:20]1>C1COCCO1>[N:1]#[C:2][c:3]1[c:4](-[c:5]2[cH:6][c:7]([N+:8](=[O:9])[O-:10])[cH:11][cH:12][cH:13]2)[n:14][c:15]([NH:16][CH:17]2[CH2:18][CH2:19]2)[n:20][c:21]1[Cl:22]\"},\"mapped_reaction_smiles\":\"O=P(Cl)(Cl)[Cl:22].O[c:21]1[c:3]([C:2]#[N:1])[c:4](-[c:5]2[cH:6][c:7]([N+:8](=[O:9])[O-:10])[cH:11][cH:12][cH:13]2)[n:14][c:15]([NH:16][CH:17]2[CH2:18][CH2:19]2)[n:20]1>C1COCCO1>[N:1]#[C:2][c:3]1[c:4](-[c:5]2[cH:6][c:7]([N+:8](=[O:9])[O-:10])[cH:11][cH:12][cH:13]2)[n:14][c:15]([NH:16][CH:17]2[CH2:18][CH2:19]2)[n:20][c:21]1[Cl:22]\"}",
"reactionStep": {
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"reactionHash": "c01bbe66220fecf88e991d7b5fd769bb295cc72541f3027877e4998d26fc2935"
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"children": [
{
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"routeId": "sa_d79427abf3c3d2c33289aeba",
"moleculeId": "sa_312a7cd3d48a055e9bc98180",
"parentId": "14168",
"isLeaf": true,
"molecule": {
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"inchikey": "XHXFXVLFKHQFAL-UHFFFAOYSA-N",
"smiles": "O=P(Cl)(Cl)Cl"
},
"smiles": "O=P(Cl)(Cl)Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
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"children": []
},
{
"id": "14170",
"routeId": "sa_d79427abf3c3d2c33289aeba",
"moleculeId": "sa_b9cb538f1c632d858d5d8066",
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"molecule": {
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"inchikey": "XJOLEYZDARLKGR-UHFFFAOYSA-N",
"smiles": "N#Cc1c(O)nc(NC2CC2)nc1-c1cccc([N+](=O)[O-])c1"
},
"smiles": "N#Cc1c(O)nc(NC2CC2)nc1-c1cccc([N+](=O)[O-])c1",
"reactionStepId": null,
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}
]
}
]
}
]
}
]
},
{
"id": "14171",
"routeId": "sa_d79427abf3c3d2c33289aeba",
"moleculeId": "sa_4fa9eaa7d866796e3b624606",
"parentId": "14163",
"isLeaf": true,
"molecule": {
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"inchikey": "QZTWVDCKDWZCLV-UHFFFAOYSA-N",
"smiles": "O=C=Nc1ccc(C(F)(F)F)cc1"
},
"smiles": "O=C=Nc1ccc(C(F)(F)F)cc1",
"reactionStepId": null,
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}
]
}
}