Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
Cc1ccc(-c2cn3nc(-c4cnccc4C(F)(F)F)ccc3n2)cc1NC(=O)C(C)(C)C
InChiKey
RWPRKPCPMYDDRB-UHFFFAOYSA-N
Route Signature
c4eb79c1ff7b2a201338cd34b24d6814c8e6acc82c4e5a5c2783c477890b1862
Synthesis route with 5 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_941c5e9ac9d67b27f4b80764",
"signature": "c4eb79c1ff7b2a201338cd34b24d6814c8e6acc82c4e5a5c2783c477890b1862",
"contentHash": "985b794c70b950ef5a8c3e4b04dbef9c835c36d4bf7905381df3f7af4f592c48",
"length": 5,
"isConvergent": true
},
"target": {
"id": "sa_11c4293154f9bdb550ce8691",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-00539",
"moleculeId": "sa_73914bc3527e6cc91ed13dc2",
"smiles": "Cc1ccc(-c2cn3nc(-c4cnccc4C(F)(F)F)ccc3n2)cc1NC(=O)C(C)(C)C",
"routeLength": 5,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_73914bc3527e6cc91ed13dc2",
"inchikey": "RWPRKPCPMYDDRB-UHFFFAOYSA-N",
"smiles": "Cc1ccc(-c2cn3nc(-c4cnccc4C(F)(F)F)ccc3n2)cc1NC(=O)C(C)(C)C"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "864",
"routeId": "sa_941c5e9ac9d67b27f4b80764",
"moleculeId": "sa_73914bc3527e6cc91ed13dc2",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_73914bc3527e6cc91ed13dc2",
"inchikey": "RWPRKPCPMYDDRB-UHFFFAOYSA-N",
"smiles": "Cc1ccc(-c2cn3nc(-c4cnccc4C(F)(F)F)ccc3n2)cc1NC(=O)C(C)(C)C"
},
"smiles": "Cc1ccc(-c2cn3nc(-c4cnccc4C(F)(F)F)ccc3n2)cc1NC(=O)C(C)(C)C",
"reactionStepId": "sa_340028f7455584fa05eabc26",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20120178751A1;0410;1239966\",\"rsmi\":\"Cl[c:17]1[n:16][n:15]2[cH:14][c:13](-[c:12]3[cH:11][c:3]([NH:4][C:5](=[O:6])[C:7]([CH3:8])([CH3:9])[CH3:10])[c:2]([CH3:1])[cH:33][cH:32]3)[n:31][c:30]2[cH:29][cH:28]1.OB(O)[c:18]1[c:19]([C:20]([F:21])([F:22])[F:23])[cH:24][cH:25][n:26][cH:27]1>CC(C)O.Cl[Pd](Cl)([PH](c1ccccc1)(c1ccccc1)c1ccccc1)[PH](c1ccccc1)(c1ccccc1)c1ccccc1.O.O=C(O)O.[Na+].[Na+]>[CH3:1][c:2]1[c:3]([NH:4][C:5](=[O:6])[C:7]([CH3:8])([CH3:9])[CH3:10])[cH:11][c:12](-[c:13]2[cH:14][n:15]3[n:16][c:17](-[c:18]4[c:19]([C:20]([F:21])([F:22])[F:23])[cH:24][cH:25][n:26][cH:27]4)[cH:28][cH:29][c:30]3[n:31]2)[cH:32][cH:33]1\"},\"mapped_reaction_smiles\":\"Cl[c:17]1[n:16][n:15]2[cH:14][c:13](-[c:12]3[cH:11][c:3]([NH:4][C:5](=[O:6])[C:7]([CH3:8])([CH3:9])[CH3:10])[c:2]([CH3:1])[cH:33][cH:32]3)[n:31][c:30]2[cH:29][cH:28]1.OB(O)[c:18]1[c:19]([C:20]([F:21])([F:22])[F:23])[cH:24][cH:25][n:26][cH:27]1>CC(C)O.Cl[Pd](Cl)([PH](c1ccccc1)(c1ccccc1)c1ccccc1)[PH](c1ccccc1)(c1ccccc1)c1ccccc1.O.O=C(O)O.[Na+].[Na+]>[CH3:1][c:2]1[c:3]([NH:4][C:5](=[O:6])[C:7]([CH3:8])([CH3:9])[CH3:10])[cH:11][c:12](-[c:13]2[cH:14][n:15]3[n:16][c:17](-[c:18]4[c:19]([C:20]([F:21])([F:22])[F:23])[cH:24][cH:25][n:26][cH:27]4)[cH:28][cH:29][c:30]3[n:31]2)[cH:32][cH:33]1\"}",
"reactionStep": {
"id": "sa_340028f7455584fa05eabc26",
"reactionHash": "e835d3566fe4724085ff5f372d87cd6d18ce72afb5ee9483f0b4350eb53008f8"
},
"children": [
{
"id": "865",
"routeId": "sa_941c5e9ac9d67b27f4b80764",
"moleculeId": "sa_5c50fdf184b096499e90a498",
"parentId": "864",
"isLeaf": false,
"molecule": {
"id": "sa_5c50fdf184b096499e90a498",
"inchikey": "GPOLKFXETWUREM-UHFFFAOYSA-N",
"smiles": "OB(O)c1cnccc1C(F)(F)F"
},
"smiles": "OB(O)c1cnccc1C(F)(F)F",
"reactionStepId": "sa_e955fcbfe2ff5026988dd305",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20120178751A1;0408;1239965\",\"rsmi\":\"Br[c:4]1[c:5]([C:6]([F:7])([F:8])[F:9])[cH:10][cH:11][n:12][cH:13]1.CC(C)O[B:2]([O:1]C(C)C)[O:3]C(C)C>C1CCOC1.[Li]CCCC>[OH:1][B:2]([OH:3])[c:4]1[c:5]([C:6]([F:7])([F:8])[F:9])[cH:10][cH:11][n:12][cH:13]1\"},\"mapped_reaction_smiles\":\"Br[c:4]1[c:5]([C:6]([F:7])([F:8])[F:9])[cH:10][cH:11][n:12][cH:13]1.CC(C)O[B:2]([O:1]C(C)C)[O:3]C(C)C>C1CCOC1.[Li]CCCC>[OH:1][B:2]([OH:3])[c:4]1[c:5]([C:6]([F:7])([F:8])[F:9])[cH:10][cH:11][n:12][cH:13]1\"}",
"reactionStep": {
"id": "sa_e955fcbfe2ff5026988dd305",
"reactionHash": "de8b382194f57fe3ed643bf05faf5ca87dab417ab381ceb0230ea08780242024"
},
"children": [
{
"id": "866",
"routeId": "sa_941c5e9ac9d67b27f4b80764",
"moleculeId": "sa_0c3a1c72e8778c8e8b205e29",
"parentId": "865",
"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": "867",
"routeId": "sa_941c5e9ac9d67b27f4b80764",
"moleculeId": "sa_7c88bacc0e5c18bf03373d6e",
"parentId": "865",
"isLeaf": true,
"molecule": {
"id": "sa_7c88bacc0e5c18bf03373d6e",
"inchikey": "OPNNLECPNPMTMV-UHFFFAOYSA-N",
"smiles": "FC(F)(F)c1ccncc1Br"
},
"smiles": "FC(F)(F)c1ccncc1Br",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "868",
"routeId": "sa_941c5e9ac9d67b27f4b80764",
"moleculeId": "sa_03ed9803863c432313ea4af5",
"parentId": "864",
"isLeaf": false,
"molecule": {
"id": "sa_03ed9803863c432313ea4af5",
"inchikey": "NCSWBNNSEBKPFD-UHFFFAOYSA-N",
"smiles": "Cc1ccc(-c2cn3nc(Cl)ccc3n2)cc1NC(=O)C(C)(C)C"
},
"smiles": "Cc1ccc(-c2cn3nc(Cl)ccc3n2)cc1NC(=O)C(C)(C)C",
"reactionStepId": "sa_e55e12b4854cf7c4a8050f00",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20120178751A1;0402;1239962\",\"rsmi\":\"Cl[C:5](=[O:6])[C:7]([CH3:8])([CH3:9])[CH3:10].[CH3:1][c:2]1[c:3]([NH2:4])[cH:11][c:12](-[c:13]2[cH:14][n:15]3[n:16][c:17]([Cl:18])[cH:19][cH:20][c:21]3[n:22]2)[cH:23][cH:24]1>CC#N.c1ccncc1>[CH3:1][c:2]1[c:3]([NH:4][C:5](=[O:6])[C:7]([CH3:8])([CH3:9])[CH3:10])[cH:11][c:12](-[c:13]2[cH:14][n:15]3[n:16][c:17]([Cl:18])[cH:19][cH:20][c:21]3[n:22]2)[cH:23][cH:24]1\"},\"mapped_reaction_smiles\":\"Cl[C:5](=[O:6])[C:7]([CH3:8])([CH3:9])[CH3:10].[CH3:1][c:2]1[c:3]([NH2:4])[cH:11][c:12](-[c:13]2[cH:14][n:15]3[n:16][c:17]([Cl:18])[cH:19][cH:20][c:21]3[n:22]2)[cH:23][cH:24]1>CC#N.c1ccncc1>[CH3:1][c:2]1[c:3]([NH:4][C:5](=[O:6])[C:7]([CH3:8])([CH3:9])[CH3:10])[cH:11][c:12](-[c:13]2[cH:14][n:15]3[n:16][c:17]([Cl:18])[cH:19][cH:20][c:21]3[n:22]2)[cH:23][cH:24]1\"}",
"reactionStep": {
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"reactionHash": "9ca648136d5d483873469f42bbf36476257a6498d660b19b1756a8b4c58b5ce1"
},
"children": [
{
"id": "869",
"routeId": "sa_941c5e9ac9d67b27f4b80764",
"moleculeId": "sa_c4a4e8fc10f9a494534f9123",
"parentId": "868",
"isLeaf": true,
"molecule": {
"id": "sa_c4a4e8fc10f9a494534f9123",
"inchikey": "JVSFQJZRHXAUGT-UHFFFAOYSA-N",
"smiles": "CC(C)(C)C(=O)Cl"
},
"smiles": "CC(C)(C)C(=O)Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "870",
"routeId": "sa_941c5e9ac9d67b27f4b80764",
"moleculeId": "sa_5a1a0bdc66f95d360dcc829b",
"parentId": "868",
"isLeaf": false,
"molecule": {
"id": "sa_5a1a0bdc66f95d360dcc829b",
"inchikey": "MRSJDRVSBVFVHP-UHFFFAOYSA-N",
"smiles": "Cc1ccc(-c2cn3nc(Cl)ccc3n2)cc1N"
},
"smiles": "Cc1ccc(-c2cn3nc(Cl)ccc3n2)cc1N",
"reactionStepId": "sa_09f22e539d96e2e36f6c8ddb",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20120178751A1;0400;1239961\",\"rsmi\":\"O=[N+:4]([O-])[c:3]1[c:2]([CH3:1])[cH:18][cH:17][c:6](-[c:7]2[cH:8][n:9]3[n:10][c:11]([Cl:12])[cH:13][cH:14][c:15]3[n:16]2)[cH:5]1>CC(=O)O.CCO.[Fe]>[CH3:1][c:2]1[c:3]([NH2:4])[cH:5][c:6](-[c:7]2[cH:8][n:9]3[n:10][c:11]([Cl:12])[cH:13][cH:14][c:15]3[n:16]2)[cH:17][cH:18]1\"},\"mapped_reaction_smiles\":\"O=[N+:4]([O-])[c:3]1[c:2]([CH3:1])[cH:18][cH:17][c:6](-[c:7]2[cH:8][n:9]3[n:10][c:11]([Cl:12])[cH:13][cH:14][c:15]3[n:16]2)[cH:5]1>CC(=O)O.CCO.[Fe]>[CH3:1][c:2]1[c:3]([NH2:4])[cH:5][c:6](-[c:7]2[cH:8][n:9]3[n:10][c:11]([Cl:12])[cH:13][cH:14][c:15]3[n:16]2)[cH:17][cH:18]1\"}",
"reactionStep": {
"id": "sa_09f22e539d96e2e36f6c8ddb",
"reactionHash": "cbf3f64ebd6b095f77643276100316abb9836dc0c0da73b18588e60219bbd427"
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"children": [
{
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"moleculeId": "sa_9bae4fa10317e05e941acf48",
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"molecule": {
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"inchikey": "XHYWVVYFTXOBMF-UHFFFAOYSA-N",
"smiles": "Cc1ccc(-c2cn3nc(Cl)ccc3n2)cc1[N+](=O)[O-]"
},
"smiles": "Cc1ccc(-c2cn3nc(Cl)ccc3n2)cc1[N+](=O)[O-]",
"reactionStepId": "sa_7175fea34628f551d1908243",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20120178751A1;0398;1239960\",\"rsmi\":\"O=[C:9]([c:8]1[cH:7][c:3]([N+:4](=[O:5])[O-:6])[c:2]([CH3:1])[cH:20][cH:19]1)[CH2:10]Br.[n:11]1[n:12][c:13]([Cl:14])[cH:15][cH:16][c:17]1[NH2:18]>CC#N.O>[CH3:1][c:2]1[c:3]([N+:4](=[O:5])[O-:6])[cH:7][c:8](-[c:9]2[cH:10][n:11]3[n:12][c:13]([Cl:14])[cH:15][cH:16][c:17]3[n:18]2)[cH:19][cH:20]1\"},\"mapped_reaction_smiles\":\"O=[C:9]([c:8]1[cH:7][c:3]([N+:4](=[O:5])[O-:6])[c:2]([CH3:1])[cH:20][cH:19]1)[CH2:10]Br.[n:11]1[n:12][c:13]([Cl:14])[cH:15][cH:16][c:17]1[NH2:18]>CC#N.O>[CH3:1][c:2]1[c:3]([N+:4](=[O:5])[O-:6])[cH:7][c:8](-[c:9]2[cH:10][n:11]3[n:12][c:13]([Cl:14])[cH:15][cH:16][c:17]3[n:18]2)[cH:19][cH:20]1\"}",
"reactionStep": {
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"molecule": {
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"inchikey": "DBMCVOBHUPAOMT-UHFFFAOYSA-N",
"smiles": "Cc1ccc(C(=O)CBr)cc1[N+](=O)[O-]"
},
"smiles": "Cc1ccc(C(=O)CBr)cc1[N+](=O)[O-]",
"reactionStepId": "sa_52ad5b7fc243b2d04a226f16",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20120178751A1;0396;1239959\",\"rsmi\":\"Br[Br:12].[CH3:1][c:2]1[c:3]([N+:4](=[O:5])[O-:6])[cH:7][c:8]([C:9](=[O:10])[CH3:11])[cH:13][cH:14]1>ClCCl>[CH3:1][c:2]1[c:3]([N+:4](=[O:5])[O-:6])[cH:7][c:8]([C:9](=[O:10])[CH2:11][Br:12])[cH:13][cH:14]1\"},\"mapped_reaction_smiles\":\"Br[Br:12].[CH3:1][c:2]1[c:3]([N+:4](=[O:5])[O-:6])[cH:7][c:8]([C:9](=[O:10])[CH3:11])[cH:13][cH:14]1>ClCCl>[CH3:1][c:2]1[c:3]([N+:4](=[O:5])[O-:6])[cH:7][c:8]([C:9](=[O:10])[CH2:11][Br:12])[cH:13][cH:14]1\"}",
"reactionStep": {
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"molecule": {
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"inchikey": "GDTBXPJZTBHREO-UHFFFAOYSA-N",
"smiles": "BrBr"
},
"smiles": "BrBr",
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},
{
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"inchikey": "YRBBMDOBWRUMEZ-UHFFFAOYSA-N",
"smiles": "CC(=O)c1ccc(C)c([N+](=O)[O-])c1"
},
"smiles": "CC(=O)c1ccc(C)c([N+](=O)[O-])c1",
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{
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"molecule": {
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},
"smiles": "Nc1ccc(Cl)nn1",
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}
]
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]
}
]
}
]
}
}