Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
Cc1ccc(-c2noc(C3CC(F)(F)C3)n2)cc1NC(=O)c1cnc2ccc(CCC(C)(C)O)cn12
InChiKey
BZTQGSHQRMAQQH-UHFFFAOYSA-N
Route Signature
c2622da9ebd486bf462fe12cb0924d5be1537d04fb03e24eac3f1373f0144c8d
Synthesis route with 6 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_cbe46ff71390d22642fd3293",
"signature": "c2622da9ebd486bf462fe12cb0924d5be1537d04fb03e24eac3f1373f0144c8d",
"contentHash": "e250fa2dd8a54bdec73b391cbcb5c7ca9c103ff5bc12b4a28ad78dc3a1990563",
"length": 6,
"isConvergent": false
},
"target": {
"id": "sa_b9e5665017f325e4e94ceb87",
"benchmarkSetId": "61e696668b63e77d7c2a29c0821768e1c383de8313852d6e995224859494442e",
"targetId": "n5-01034",
"moleculeId": "sa_336a4ac40b9683297e0d715f",
"smiles": "Cc1ccc(-c2noc(C3CC(F)(F)C3)n2)cc1NC(=O)c1cnc2ccc(CCC(C)(C)O)cn12",
"routeLength": 6,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_336a4ac40b9683297e0d715f",
"inchikey": "BZTQGSHQRMAQQH-UHFFFAOYSA-N",
"smiles": "Cc1ccc(-c2noc(C3CC(F)(F)C3)n2)cc1NC(=O)c1cnc2ccc(CCC(C)(C)O)cn12"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "14004",
"routeId": "sa_cbe46ff71390d22642fd3293",
"moleculeId": "sa_336a4ac40b9683297e0d715f",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_336a4ac40b9683297e0d715f",
"inchikey": "BZTQGSHQRMAQQH-UHFFFAOYSA-N",
"smiles": "Cc1ccc(-c2noc(C3CC(F)(F)C3)n2)cc1NC(=O)c1cnc2ccc(CCC(C)(C)O)cn12"
},
"smiles": "Cc1ccc(-c2noc(C3CC(F)(F)C3)n2)cc1NC(=O)c1cnc2ccc(CCC(C)(C)O)cn12",
"reactionStepId": "sa_86aae297cf22254e58330378",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US09199981B2;0603;1700497\",\"rsmi\":\"Br[Mg][CH3:18].[CH3:1][c:2]1[c:3]([NH:4][C:5](=[O:6])[c:7]2[cH:8][n:9][c:10]3[cH:11][cH:12][c:13]([CH2:14][CH2:15][C:16]([CH3:17])=[O:19])[cH:20][n:21]23)[cH:22][c:23](-[c:24]2[n:25][o:26][c:27]([CH:28]3[CH2:29][C:30]([F:31])([F:32])[CH2:33]3)[n:34]2)[cH:35][cH:36]1>C1CCOC1>[CH3:1][c:2]1[c:3]([NH:4][C:5](=[O:6])[c:7]2[cH:8][n:9][c:10]3[cH:11][cH:12][c:13]([CH2:14][CH2:15][C:16]([CH3:17])([CH3:18])[OH:19])[cH:20][n:21]23)[cH:22][c:23](-[c:24]2[n:25][o:26][c:27]([CH:28]3[CH2:29][C:30]([F:31])([F:32])[CH2:33]3)[n:34]2)[cH:35][cH:36]1\"},\"mapped_reaction_smiles\":\"Br[Mg][CH3:18].[CH3:1][c:2]1[c:3]([NH:4][C:5](=[O:6])[c:7]2[cH:8][n:9][c:10]3[cH:11][cH:12][c:13]([CH2:14][CH2:15][C:16]([CH3:17])=[O:19])[cH:20][n:21]23)[cH:22][c:23](-[c:24]2[n:25][o:26][c:27]([CH:28]3[CH2:29][C:30]([F:31])([F:32])[CH2:33]3)[n:34]2)[cH:35][cH:36]1>C1CCOC1>[CH3:1][c:2]1[c:3]([NH:4][C:5](=[O:6])[c:7]2[cH:8][n:9][c:10]3[cH:11][cH:12][c:13]([CH2:14][CH2:15][C:16]([CH3:17])([CH3:18])[OH:19])[cH:20][n:21]23)[cH:22][c:23](-[c:24]2[n:25][o:26][c:27]([CH:28]3[CH2:29][C:30]([F:31])([F:32])[CH2:33]3)[n:34]2)[cH:35][cH:36]1\"}",
"reactionStep": {
"id": "sa_86aae297cf22254e58330378",
"reactionHash": "63b6103537b989946c11ebfbbe5c3932dcb018b5eb9ea662e3f2e4003976b410"
},
"children": [
{
"id": "14005",
"routeId": "sa_cbe46ff71390d22642fd3293",
"moleculeId": "sa_1f49d1fc04ca53874d94e458",
"parentId": "14004",
"isLeaf": true,
"molecule": {
"id": "sa_1f49d1fc04ca53874d94e458",
"inchikey": "AVFUHBJCUUTGCD-UHFFFAOYSA-M",
"smiles": "[CH3][Mg][Br]"
},
"smiles": "[CH3][Mg][Br]",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "14006",
"routeId": "sa_cbe46ff71390d22642fd3293",
"moleculeId": "sa_826212b68489441227f4ea92",
"parentId": "14004",
"isLeaf": false,
"molecule": {
"id": "sa_826212b68489441227f4ea92",
"inchikey": "CCLJVGUJPXWOOW-UHFFFAOYSA-N",
"smiles": "CC(=O)CCc1ccc2ncc(C(=O)Nc3cc(-c4noc(C5CC(F)(F)C5)n4)ccc3C)n2c1"
},
"smiles": "CC(=O)CCc1ccc2ncc(C(=O)Nc3cc(-c4noc(C5CC(F)(F)C5)n4)ccc3C)n2c1",
"reactionStepId": "sa_cdd7b62af6a6dfe6c5ee134d",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US09199981B2;0601;1700496\",\"rsmi\":\"O[C:10]([c:9]1[n:8]2[cH:7][c:6]([CH2:5][CH2:4][C:2]([CH3:1])=[O:3])[cH:35][cH:34][c:33]2[n:32][cH:31]1)=[O:11].[NH2:12][c:13]1[c:14]([CH3:15])[cH:16][cH:17][c:18](-[c:19]2[n:20][o:21][c:22]([CH:23]3[CH2:24][C:25]([F:26])([F:27])[CH2:28]3)[n:29]2)[cH:30]1>CN(C)C=O.ClCCl.O=C(Cl)C(=O)Cl.c1ccncc1>[CH3:1][C:2](=[O:3])[CH2:4][CH2:5][c:6]1[cH:7][n:8]2[c:9]([C:10](=[O:11])[NH:12][c:13]3[c:14]([CH3:15])[cH:16][cH:17][c:18](-[c:19]4[n:20][o:21][c:22]([CH:23]5[CH2:24][C:25]([F:26])([F:27])[CH2:28]5)[n:29]4)[cH:30]3)[cH:31][n:32][c:33]2[cH:34][cH:35]1\"},\"mapped_reaction_smiles\":\"O[C:10]([c:9]1[n:8]2[cH:7][c:6]([CH2:5][CH2:4][C:2]([CH3:1])=[O:3])[cH:35][cH:34][c:33]2[n:32][cH:31]1)=[O:11].[NH2:12][c:13]1[c:14]([CH3:15])[cH:16][cH:17][c:18](-[c:19]2[n:20][o:21][c:22]([CH:23]3[CH2:24][C:25]([F:26])([F:27])[CH2:28]3)[n:29]2)[cH:30]1>CN(C)C=O.ClCCl.O=C(Cl)C(=O)Cl.c1ccncc1>[CH3:1][C:2](=[O:3])[CH2:4][CH2:5][c:6]1[cH:7][n:8]2[c:9]([C:10](=[O:11])[NH:12][c:13]3[c:14]([CH3:15])[cH:16][cH:17][c:18](-[c:19]4[n:20][o:21][c:22]([CH:23]5[CH2:24][C:25]([F:26])([F:27])[CH2:28]5)[n:29]4)[cH:30]3)[cH:31][n:32][c:33]2[cH:34][cH:35]1\"}",
"reactionStep": {
"id": "sa_cdd7b62af6a6dfe6c5ee134d",
"reactionHash": "9d03f9e4bd544de1afb209db70310d6d50d679f37b7abdf6103a1f574a23ca94"
},
"children": [
{
"id": "14007",
"routeId": "sa_cbe46ff71390d22642fd3293",
"moleculeId": "sa_2719c165681d55ad4b4c0255",
"parentId": "14006",
"isLeaf": true,
"molecule": {
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"inchikey": "FQFWKACTJHCRAK-UHFFFAOYSA-N",
"smiles": "CC(=O)CCc1ccc2ncc(C(=O)O)n2c1"
},
"smiles": "CC(=O)CCc1ccc2ncc(C(=O)O)n2c1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "14008",
"routeId": "sa_cbe46ff71390d22642fd3293",
"moleculeId": "sa_43e3ce8646c74ac0ca51605b",
"parentId": "14006",
"isLeaf": false,
"molecule": {
"id": "sa_43e3ce8646c74ac0ca51605b",
"inchikey": "YJEKLHRXYWLNMQ-UHFFFAOYSA-N",
"smiles": "Cc1ccc(-c2noc(C3CC(F)(F)C3)n2)cc1N"
},
"smiles": "Cc1ccc(-c2noc(C3CC(F)(F)C3)n2)cc1N",
"reactionStepId": "sa_6a04182a6b6246e9c5647ad8",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US09199981B2;0455;1700434\",\"rsmi\":\"CC(C)(C)OC(=O)[NH:4][c:3]1[c:2]([CH3:1])[cH:19][cH:18][c:6](-[c:7]2[n:8][o:9][c:10]([CH:11]3[CH2:12][C:13]([F:14])([F:15])[CH2:16]3)[n:17]2)[cH:5]1>O=C(O)C(F)(F)F.O=C(O)O.[Na+].[Na+]>[CH3:1][c:2]1[c:3]([NH2:4])[cH:5][c:6](-[c:7]2[n:8][o:9][c:10]([CH:11]3[CH2:12][C:13]([F:14])([F:15])[CH2:16]3)[n:17]2)[cH:18][cH:19]1\"},\"mapped_reaction_smiles\":\"CC(C)(C)OC(=O)[NH:4][c:3]1[c:2]([CH3:1])[cH:19][cH:18][c:6](-[c:7]2[n:8][o:9][c:10]([CH:11]3[CH2:12][C:13]([F:14])([F:15])[CH2:16]3)[n:17]2)[cH:5]1>O=C(O)C(F)(F)F.O=C(O)O.[Na+].[Na+]>[CH3:1][c:2]1[c:3]([NH2:4])[cH:5][c:6](-[c:7]2[n:8][o:9][c:10]([CH:11]3[CH2:12][C:13]([F:14])([F:15])[CH2:16]3)[n:17]2)[cH:18][cH:19]1\"}",
"reactionStep": {
"id": "sa_6a04182a6b6246e9c5647ad8",
"reactionHash": "7bd788849843bdfd533ebd1f18cc769c2e9298b2217f0987a841b4145aed0e59"
},
"children": [
{
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"parentId": "14008",
"isLeaf": false,
"molecule": {
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"inchikey": "FHTSICXUODRGMX-UHFFFAOYSA-N",
"smiles": "Cc1ccc(-c2noc(C3CC(F)(F)C3)n2)cc1NC(=O)OC(C)(C)C"
},
"smiles": "Cc1ccc(-c2noc(C3CC(F)(F)C3)n2)cc1NC(=O)OC(C)(C)C",
"reactionStepId": "sa_1a21783ae22c4783c54d5bf1",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US09199981B2;0454;1700433\",\"rsmi\":\"O=[C:17](O)[CH:18]1[CH2:19][C:20]([F:21])([F:22])[CH2:23]1.[CH3:1][c:2]1[c:3]([NH:4][C:5](=[O:6])[O:7][C:8]([CH3:9])([CH3:10])[CH3:11])[cH:12][c:13](/[C:14](=[N:15]/[OH:16])[NH2:24])[cH:25][cH:26]1>CN1CCCC1=O.O=C(n1ccnc1)n1ccnc1>[CH3:1][c:2]1[c:3]([NH:4][C:5](=[O:6])[O:7][C:8]([CH3:9])([CH3:10])[CH3:11])[cH:12][c:13](-[c:14]2[n:15][o:16][c:17]([CH:18]3[CH2:19][C:20]([F:21])([F:22])[CH2:23]3)[n:24]2)[cH:25][cH:26]1\"},\"mapped_reaction_smiles\":\"O=[C:17](O)[CH:18]1[CH2:19][C:20]([F:21])([F:22])[CH2:23]1.[CH3:1][c:2]1[c:3]([NH:4][C:5](=[O:6])[O:7][C:8]([CH3:9])([CH3:10])[CH3:11])[cH:12][c:13](/[C:14](=[N:15]/[OH:16])[NH2:24])[cH:25][cH:26]1>CN1CCCC1=O.O=C(n1ccnc1)n1ccnc1>[CH3:1][c:2]1[c:3]([NH:4][C:5](=[O:6])[O:7][C:8]([CH3:9])([CH3:10])[CH3:11])[cH:12][c:13](-[c:14]2[n:15][o:16][c:17]([CH:18]3[CH2:19][C:20]([F:21])([F:22])[CH2:23]3)[n:24]2)[cH:25][cH:26]1\"}",
"reactionStep": {
"id": "sa_1a21783ae22c4783c54d5bf1",
"reactionHash": "594673d9c523322812dee65abfb4c4b7ea445caffb3526175c9916f5495fdc09"
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"children": [
{
"id": "14010",
"routeId": "sa_cbe46ff71390d22642fd3293",
"moleculeId": "sa_4bdab31071797c79465d120c",
"parentId": "14009",
"isLeaf": false,
"molecule": {
"id": "sa_4bdab31071797c79465d120c",
"inchikey": "PADHYNAGFKWCHY-UHFFFAOYSA-N",
"smiles": "Cc1ccc(/C(N)=N/O)cc1NC(=O)OC(C)(C)C"
},
"smiles": "Cc1ccc(/C(N)=N/O)cc1NC(=O)OC(C)(C)C",
"reactionStepId": "sa_a48277d3499cd5817cc6f854",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US09199981B2;0453;1700432\",\"rsmi\":\"[CH3:1][c:2]1[c:3]([NH:4][C:5](=[O:6])[O:7][C:8]([CH3:9])([CH3:10])[CH3:11])[cH:12][c:13]([C:14]#[N:15])[cH:18][cH:19]1.[NH2:16][OH:17]>CCO>[CH3:1][c:2]1[c:3]([NH:4][C:5](=[O:6])[O:7][C:8]([CH3:9])([CH3:10])[CH3:11])[cH:12][c:13](/[C:14]([NH2:15])=[N:16]/[OH:17])[cH:18][cH:19]1\"},\"mapped_reaction_smiles\":\"[CH3:1][c:2]1[c:3]([NH:4][C:5](=[O:6])[O:7][C:8]([CH3:9])([CH3:10])[CH3:11])[cH:12][c:13]([C:14]#[N:15])[cH:18][cH:19]1.[NH2:16][OH:17]>CCO>[CH3:1][c:2]1[c:3]([NH:4][C:5](=[O:6])[O:7][C:8]([CH3:9])([CH3:10])[CH3:11])[cH:12][c:13](/[C:14]([NH2:15])=[N:16]/[OH:17])[cH:18][cH:19]1\"}",
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"children": [
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"moleculeId": "sa_04a18e3f07bde82ca29399ee",
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"molecule": {
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"inchikey": "AVXURJPOCDRRFD-UHFFFAOYSA-N",
"smiles": "NO"
},
"smiles": "NO",
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},
{
"id": "14012",
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"molecule": {
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"inchikey": "SHUHJZNRZMRQSH-UHFFFAOYSA-N",
"smiles": "Cc1ccc(C#N)cc1NC(=O)OC(C)(C)C"
},
"smiles": "Cc1ccc(C#N)cc1NC(=O)OC(C)(C)C",
"reactionStepId": "sa_560cf04eeaea5cabc8e6a1bd",
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"metadata": "{\"annotations\":{\"ID\":\"US09199981B2;0452;1700431\",\"rsmi\":\"CC(C)(C)OC(=O)O[C:5](=[O:6])[O:7][C:8]([CH3:9])([CH3:10])[CH3:11].[CH3:1][c:2]1[c:3]([NH2:4])[cH:12][c:13]([C:14]#[N:15])[cH:16][cH:17]1>C1CCOC1.CN(C)c1ccncc1>[CH3:1][c:2]1[c:3]([NH:4][C:5](=[O:6])[O:7][C:8]([CH3:9])([CH3:10])[CH3:11])[cH:12][c:13]([C:14]#[N:15])[cH:16][cH:17]1\"},\"mapped_reaction_smiles\":\"CC(C)(C)OC(=O)O[C:5](=[O:6])[O:7][C:8]([CH3:9])([CH3:10])[CH3:11].[CH3:1][c:2]1[c:3]([NH2:4])[cH:12][c:13]([C:14]#[N:15])[cH:16][cH:17]1>C1CCOC1.CN(C)c1ccncc1>[CH3:1][c:2]1[c:3]([NH:4][C:5](=[O:6])[O:7][C:8]([CH3:9])([CH3:10])[CH3:11])[cH:12][c:13]([C:14]#[N:15])[cH:16][cH:17]1\"}",
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{
"id": "14014",
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"smiles": "Cc1ccc(C#N)cc1N"
},
"smiles": "Cc1ccc(C#N)cc1N",
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}
]
}
]
},
{
"id": "14015",
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"molecule": {
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"inchikey": "PLRCVBKYFLWAAT-UHFFFAOYSA-N",
"smiles": "O=C(O)C1CC(F)(F)C1"
},
"smiles": "O=C(O)C1CC(F)(F)C1",
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}
]
}
]
}
]
}
]
}
}