Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
Cc1ccc2cc(Cn3cc(C(=O)NCc4c(C)cc(N)nc4C)nn3)ccc2n1
InChiKey
BYZNGWXDOMLVBH-UHFFFAOYSA-N
Route Signature
9591a4e0caabf23e1e6b5b0738aababd11486129f61483451ce04ebdb53f7597
Synthesis route with 5 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_a8bc267f69196406e2822ac9",
"signature": "9591a4e0caabf23e1e6b5b0738aababd11486129f61483451ce04ebdb53f7597",
"contentHash": "cad52c3b9e373f5a79339afe6f82d58d3e051a6d2b3539c31e94ab57e0d2b595",
"length": 5,
"isConvergent": true
},
"target": {
"id": "sa_47ce87883d049dcf4a8b3696",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-01298",
"moleculeId": "sa_e387f275758bf09d106bb1e1",
"smiles": "Cc1ccc2cc(Cn3cc(C(=O)NCc4c(C)cc(N)nc4C)nn3)ccc2n1",
"routeLength": 5,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_e387f275758bf09d106bb1e1",
"inchikey": "BYZNGWXDOMLVBH-UHFFFAOYSA-N",
"smiles": "Cc1ccc2cc(Cn3cc(C(=O)NCc4c(C)cc(N)nc4C)nn3)ccc2n1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "1475",
"routeId": "sa_a8bc267f69196406e2822ac9",
"moleculeId": "sa_e387f275758bf09d106bb1e1",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_e387f275758bf09d106bb1e1",
"inchikey": "BYZNGWXDOMLVBH-UHFFFAOYSA-N",
"smiles": "Cc1ccc2cc(Cn3cc(C(=O)NCc4c(C)cc(N)nc4C)nn3)ccc2n1"
},
"smiles": "Cc1ccc2cc(Cn3cc(C(=O)NCc4c(C)cc(N)nc4C)nn3)ccc2n1",
"reactionStepId": "sa_154a2f2dcd44359ac39dfb0c",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20120035168A1;0746;1176436\",\"rsmi\":\"CC(C)(C)OC(=O)[NH:21][c:20]1[cH:19][c:17]([CH3:18])[c:16]([CH2:15][NH:14][C:12]([c:11]2[cH:10][n:9]([CH2:8][c:7]3[cH:6][cH:5][c:4]4[n:3][c:2]([CH3:1])[cH:30][cH:29][c:28]4[cH:27]3)[n:26][n:25]2)=[O:13])[c:23]([CH3:24])[n:22]1>ClCCl.O=C(O)C(F)(F)F>[CH3:1][c:2]1[n:3][c:4]2[cH:5][cH:6][c:7]([CH2:8][n:9]3[cH:10][c:11]([C:12](=[O:13])[NH:14][CH2:15][c:16]4[c:17]([CH3:18])[cH:19][c:20]([NH2:21])[n:22][c:23]4[CH3:24])[n:25][n:26]3)[cH:27][c:28]2[cH:29][cH:30]1\"},\"mapped_reaction_smiles\":\"CC(C)(C)OC(=O)[NH:21][c:20]1[cH:19][c:17]([CH3:18])[c:16]([CH2:15][NH:14][C:12]([c:11]2[cH:10][n:9]([CH2:8][c:7]3[cH:6][cH:5][c:4]4[n:3][c:2]([CH3:1])[cH:30][cH:29][c:28]4[cH:27]3)[n:26][n:25]2)=[O:13])[c:23]([CH3:24])[n:22]1>ClCCl.O=C(O)C(F)(F)F>[CH3:1][c:2]1[n:3][c:4]2[cH:5][cH:6][c:7]([CH2:8][n:9]3[cH:10][c:11]([C:12](=[O:13])[NH:14][CH2:15][c:16]4[c:17]([CH3:18])[cH:19][c:20]([NH2:21])[n:22][c:23]4[CH3:24])[n:25][n:26]3)[cH:27][c:28]2[cH:29][cH:30]1\"}",
"reactionStep": {
"id": "sa_154a2f2dcd44359ac39dfb0c",
"reactionHash": "002d5319f5234a250530f52fc15b77ed3c0efe3027d9dd0367a52097dab3910f"
},
"children": [
{
"id": "1476",
"routeId": "sa_a8bc267f69196406e2822ac9",
"moleculeId": "sa_82741de361b7516a8b832cc3",
"parentId": "1475",
"isLeaf": false,
"molecule": {
"id": "sa_82741de361b7516a8b832cc3",
"inchikey": "UZFKNOVJCLTNHV-UHFFFAOYSA-N",
"smiles": "Cc1ccc2cc(Cn3cc(C(=O)NCc4c(C)cc(NC(=O)OC(C)(C)C)nc4C)nn3)ccc2n1"
},
"smiles": "Cc1ccc2cc(Cn3cc(C(=O)NCc4c(C)cc(NC(=O)OC(C)(C)C)nc4C)nn3)ccc2n1",
"reactionStepId": "sa_6585f614f8f184d32d5c578e",
"template": null,
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"reactionStep": {
"id": "sa_6585f614f8f184d32d5c578e",
"reactionHash": "1cfdd806f9275277a2d2a7a04f12dcb9981ca821d1067210b4c9d70064ae7b79"
},
"children": [
{
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"moleculeId": "sa_171923f3eb851189661f38b9",
"parentId": "1476",
"isLeaf": false,
"molecule": {
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"inchikey": "QSDOBDVEEOSPOI-UHFFFAOYSA-N",
"smiles": "C#CC(=O)NCc1c(C)cc(NC(=O)OC(C)(C)C)nc1C"
},
"smiles": "C#CC(=O)NCc1c(C)cc(NC(=O)OC(C)(C)C)nc1C",
"reactionStepId": "sa_44d7cfd6856edccd59d6a7f6",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20120035168A1;0743;1176433\",\"rsmi\":\"O[C:3]([C:2]#[CH:1])=[O:4].[NH2:5][CH2:6][c:7]1[c:8]([CH3:9])[n:10][c:11]([NH:12][C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[cH:20][c:21]1[CH3:22]>CCCP(=O)=O.CCN(C(C)C)C(C)C.CN(C)C=O.ClCCl>[CH:1]#[C:2][C:3](=[O:4])[NH:5][CH2:6][c:7]1[c:8]([CH3:9])[n:10][c:11]([NH:12][C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[cH:20][c:21]1[CH3:22]\"},\"mapped_reaction_smiles\":\"O[C:3]([C:2]#[CH:1])=[O:4].[NH2:5][CH2:6][c:7]1[c:8]([CH3:9])[n:10][c:11]([NH:12][C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[cH:20][c:21]1[CH3:22]>CCCP(=O)=O.CCN(C(C)C)C(C)C.CN(C)C=O.ClCCl>[CH:1]#[C:2][C:3](=[O:4])[NH:5][CH2:6][c:7]1[c:8]([CH3:9])[n:10][c:11]([NH:12][C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[cH:20][c:21]1[CH3:22]\"}",
"reactionStep": {
"id": "sa_44d7cfd6856edccd59d6a7f6",
"reactionHash": "a914bf9f2ce6ff0da1f49326c69b5182db3d6357e3d54a19d72d8f1643b4e94f"
},
"children": [
{
"id": "1478",
"routeId": "sa_a8bc267f69196406e2822ac9",
"moleculeId": "sa_9aeb32d3f75e504dff4c1066",
"parentId": "1477",
"isLeaf": false,
"molecule": {
"id": "sa_9aeb32d3f75e504dff4c1066",
"inchikey": "LXDSHZCTNZCBOS-UHFFFAOYSA-N",
"smiles": "Cc1cc(NC(=O)OC(C)(C)C)nc(C)c1CN"
},
"smiles": "Cc1cc(NC(=O)OC(C)(C)C)nc(C)c1CN",
"reactionStepId": "sa_3a981d2798227ecaa188ae2e",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20120035168A1;0445;1176408\",\"rsmi\":\"[CH3:1][c:2]1[cH:3][c:4]([NH:5][C:6](=[O:7])[O:8][C:9]([CH3:10])([CH3:11])[CH3:12])[n:13][c:14]([CH3:15])[c:16]1[C:17]#[N:18]>CO.N.[Ni]>[CH3:1][c:2]1[cH:3][c:4]([NH:5][C:6](=[O:7])[O:8][C:9]([CH3:10])([CH3:11])[CH3:12])[n:13][c:14]([CH3:15])[c:16]1[CH2:17][NH2:18]\"},\"mapped_reaction_smiles\":\"[CH3:1][c:2]1[cH:3][c:4]([NH:5][C:6](=[O:7])[O:8][C:9]([CH3:10])([CH3:11])[CH3:12])[n:13][c:14]([CH3:15])[c:16]1[C:17]#[N:18]>CO.N.[Ni]>[CH3:1][c:2]1[cH:3][c:4]([NH:5][C:6](=[O:7])[O:8][C:9]([CH3:10])([CH3:11])[CH3:12])[n:13][c:14]([CH3:15])[c:16]1[CH2:17][NH2:18]\"}",
"reactionStep": {
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"reactionHash": "a209d1d6f7da41082c19ae964c9881fcc16e9794cab1958f9100a6d93be64bdc"
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"children": [
{
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"molecule": {
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"smiles": "Cc1cc(NC(=O)OC(C)(C)C)nc(C)c1C#N"
},
"smiles": "Cc1cc(NC(=O)OC(C)(C)C)nc(C)c1C#N",
"reactionStepId": "sa_36148b92feb6f60c557cb355",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20120035168A1;0444;1176407\",\"rsmi\":\"CC(C)(C)OC(=O)O[C:6](=[O:7])[O:8][C:9]([CH3:10])([CH3:11])[CH3:12].[CH3:1][c:2]1[cH:3][c:4]([NH2:5])[n:13][c:14]([CH3:15])[c:16]1[C:17]#[N:18]>C1CCOC1.CN(C)c1ccncc1.CO.ClCCl.OO.[Na+].O>[CH3:1][c:2]1[cH:3][c:4]([NH:5][C:6](=[O:7])[O:8][C:9]([CH3:10])([CH3:11])[CH3:12])[n:13][c:14]([CH3:15])[c:16]1[C:17]#[N:18]\"},\"mapped_reaction_smiles\":\"CC(C)(C)OC(=O)O[C:6](=[O:7])[O:8][C:9]([CH3:10])([CH3:11])[CH3:12].[CH3:1][c:2]1[cH:3][c:4]([NH2:5])[n:13][c:14]([CH3:15])[c:16]1[C:17]#[N:18]>C1CCOC1.CN(C)c1ccncc1.CO.ClCCl.OO.[Na+].O>[CH3:1][c:2]1[cH:3][c:4]([NH:5][C:6](=[O:7])[O:8][C:9]([CH3:10])([CH3:11])[CH3:12])[n:13][c:14]([CH3:15])[c:16]1[C:17]#[N:18]\"}",
"reactionStep": {
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"molecule": {
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{
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"molecule": {
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"smiles": "Cc1cc(N)nc(C)c1C#N"
},
"smiles": "Cc1cc(N)nc(C)c1C#N",
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},
{
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"molecule": {
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"smiles": "C#CC(=O)O"
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"smiles": "C#CC(=O)O",
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{
"id": "1483",
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"molecule": {
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"inchikey": "XWMXDGMPOBQOCU-UHFFFAOYSA-N",
"smiles": "Cc1ccc2cc(CN=[N+]=[N-])ccc2n1"
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"smiles": "Cc1ccc2cc(CN=[N+]=[N-])ccc2n1",
"reactionStepId": "sa_0e60b5fa5f5fc31016452169",
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"metadata": "{\"annotations\":{\"ID\":\"US20120035168A1;0744;1176434\",\"rsmi\":\"O=P(c1ccccc1)(c1ccccc1)[N:9]=[N+:10]=[N-:11].O[CH2:8][c:7]1[cH:6][cH:5][c:4]2[n:3][c:2]([CH3:1])[cH:15][cH:14][c:13]2[cH:12]1>C1CCC2=NCCCN2CC1.CN(C)C=O.O>[CH3:1][c:2]1[n:3][c:4]2[cH:5][cH:6][c:7]([CH2:8][N:9]=[N+:10]=[N-:11])[cH:12][c:13]2[cH:14][cH:15]1\"},\"mapped_reaction_smiles\":\"O=P(c1ccccc1)(c1ccccc1)[N:9]=[N+:10]=[N-:11].O[CH2:8][c:7]1[cH:6][cH:5][c:4]2[n:3][c:2]([CH3:1])[cH:15][cH:14][c:13]2[cH:12]1>C1CCC2=NCCCN2CC1.CN(C)C=O.O>[CH3:1][c:2]1[n:3][c:4]2[cH:5][cH:6][c:7]([CH2:8][N:9]=[N+:10]=[N-:11])[cH:12][c:13]2[cH:14][cH:15]1\"}",
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{
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}
]
}
}