Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CNc1nc(Nc2cc(C)c(C(=O)N3CCOCC3)cc2OC)ncc1C(F)(F)F
InChiKey
TXNVISBGVPMNMN-UHFFFAOYSA-N
Route Signature
104c733390964cbd642479c5ce036aaa766d5318e06d2e11ab9528a1c9c617c1
Synthesis route with 5 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_7ff98bebb54842ec9885bf0c",
"signature": "104c733390964cbd642479c5ce036aaa766d5318e06d2e11ab9528a1c9c617c1",
"contentHash": "fdfd85cc9fc56a669fe08dc6fda35a8f0181cae68772d62517ddd37f93cc3dd7",
"length": 5,
"isConvergent": false
},
"target": {
"id": "sa_5026c24fdf42e822f20027ad",
"benchmarkSetId": "61e696668b63e77d7c2a29c0821768e1c383de8313852d6e995224859494442e",
"targetId": "n5-01461",
"moleculeId": "sa_09af4405321da7491aa93466",
"smiles": "CNc1nc(Nc2cc(C)c(C(=O)N3CCOCC3)cc2OC)ncc1C(F)(F)F",
"routeLength": 5,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_09af4405321da7491aa93466",
"inchikey": "TXNVISBGVPMNMN-UHFFFAOYSA-N",
"smiles": "CNc1nc(Nc2cc(C)c(C(=O)N3CCOCC3)cc2OC)ncc1C(F)(F)F"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "14346",
"routeId": "sa_7ff98bebb54842ec9885bf0c",
"moleculeId": "sa_09af4405321da7491aa93466",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_09af4405321da7491aa93466",
"inchikey": "TXNVISBGVPMNMN-UHFFFAOYSA-N",
"smiles": "CNc1nc(Nc2cc(C)c(C(=O)N3CCOCC3)cc2OC)ncc1C(F)(F)F"
},
"smiles": "CNc1nc(Nc2cc(C)c(C(=O)N3CCOCC3)cc2OC)ncc1C(F)(F)F",
"reactionStepId": "sa_c8d1223971c9fd4f0ad55247",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130157999A1;0732;1382819\",\"rsmi\":\"Cl[c:5]1[n:4][c:3]([NH:2][CH3:1])[c:26]([C:27]([F:28])([F:29])[F:30])[cH:25][n:24]1.[NH2:6][c:7]1[cH:8][c:9]([CH3:10])[c:11]([C:12](=[O:13])[N:14]2[CH2:15][CH2:16][O:17][CH2:18][CH2:19]2)[cH:20][c:21]1[O:22][CH3:23]>C1COCCO1.Cc1ccc(S(=O)(=O)O)cc1.ClCCl.O=C(O)O.[Na+]>[CH3:1][NH:2][c:3]1[n:4][c:5]([NH:6][c:7]2[cH:8][c:9]([CH3:10])[c:11]([C:12](=[O:13])[N:14]3[CH2:15][CH2:16][O:17][CH2:18][CH2:19]3)[cH:20][c:21]2[O:22][CH3:23])[n:24][cH:25][c:26]1[C:27]([F:28])([F:29])[F:30]\"},\"mapped_reaction_smiles\":\"Cl[c:5]1[n:4][c:3]([NH:2][CH3:1])[c:26]([C:27]([F:28])([F:29])[F:30])[cH:25][n:24]1.[NH2:6][c:7]1[cH:8][c:9]([CH3:10])[c:11]([C:12](=[O:13])[N:14]2[CH2:15][CH2:16][O:17][CH2:18][CH2:19]2)[cH:20][c:21]1[O:22][CH3:23]>C1COCCO1.Cc1ccc(S(=O)(=O)O)cc1.ClCCl.O=C(O)O.[Na+]>[CH3:1][NH:2][c:3]1[n:4][c:5]([NH:6][c:7]2[cH:8][c:9]([CH3:10])[c:11]([C:12](=[O:13])[N:14]3[CH2:15][CH2:16][O:17][CH2:18][CH2:19]3)[cH:20][c:21]2[O:22][CH3:23])[n:24][cH:25][c:26]1[C:27]([F:28])([F:29])[F:30]\"}",
"reactionStep": {
"id": "sa_c8d1223971c9fd4f0ad55247",
"reactionHash": "072d541af9cdf24860d687c5e425f5590d469f7ae1218c351e9b23fa32638ab3"
},
"children": [
{
"id": "14347",
"routeId": "sa_7ff98bebb54842ec9885bf0c",
"moleculeId": "sa_edb1723ac0c8a680ee85deb1",
"parentId": "14346",
"isLeaf": true,
"molecule": {
"id": "sa_edb1723ac0c8a680ee85deb1",
"inchikey": "DBZWBBJKHCGBCI-UHFFFAOYSA-N",
"smiles": "CNc1nc(Cl)ncc1C(F)(F)F"
},
"smiles": "CNc1nc(Cl)ncc1C(F)(F)F",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "14348",
"routeId": "sa_7ff98bebb54842ec9885bf0c",
"moleculeId": "sa_e4859076a2ee37ede47981c3",
"parentId": "14346",
"isLeaf": false,
"molecule": {
"id": "sa_e4859076a2ee37ede47981c3",
"inchikey": "OXCLWRRUQTWACJ-UHFFFAOYSA-N",
"smiles": "COc1cc(C(=O)N2CCOCC2)c(C)cc1N"
},
"smiles": "COc1cc(C(=O)N2CCOCC2)c(C)cc1N",
"reactionStepId": "sa_10f889dcb1d6c844d608156c",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130157999A1;0696;1382803\",\"rsmi\":\"O=[N+:18]([O-])[c:17]1[c:3]([O:2][CH3:1])[cH:4][c:5]([C:6](=[O:7])[N:8]2[CH2:9][CH2:10][O:11][CH2:12][CH2:13]2)[c:14]([CH3:15])[cH:16]1>CCO.ClCCl.Cl[Sn]Cl.O.O.O.[Na+].O>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[N:8]2[CH2:9][CH2:10][O:11][CH2:12][CH2:13]2)[c:14]([CH3:15])[cH:16][c:17]1[NH2:18]\"},\"mapped_reaction_smiles\":\"O=[N+:18]([O-])[c:17]1[c:3]([O:2][CH3:1])[cH:4][c:5]([C:6](=[O:7])[N:8]2[CH2:9][CH2:10][O:11][CH2:12][CH2:13]2)[c:14]([CH3:15])[cH:16]1>CCO.ClCCl.Cl[Sn]Cl.O.O.O.[Na+].O>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[N:8]2[CH2:9][CH2:10][O:11][CH2:12][CH2:13]2)[c:14]([CH3:15])[cH:16][c:17]1[NH2:18]\"}",
"reactionStep": {
"id": "sa_10f889dcb1d6c844d608156c",
"reactionHash": "a90ea2453b946a2c39e788f5e4652c5009c5440cfee865f4a04661d5b7eab5e4"
},
"children": [
{
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"routeId": "sa_7ff98bebb54842ec9885bf0c",
"moleculeId": "sa_950bd0e285e445597f0804ed",
"parentId": "14348",
"isLeaf": false,
"molecule": {
"id": "sa_950bd0e285e445597f0804ed",
"inchikey": "SIFCSVVNNHITQY-UHFFFAOYSA-N",
"smiles": "COc1cc(C(=O)N2CCOCC2)c(C)cc1[N+](=O)[O-]"
},
"smiles": "COc1cc(C(=O)N2CCOCC2)c(C)cc1[N+](=O)[O-]",
"reactionStepId": "sa_d190a729950ef0d45dd91888",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130157999A1;0694;1382802\",\"rsmi\":\"O[C:6]([c:5]1[cH:4][c:3]([O:2][CH3:1])[c:17]([N+:18](=[O:19])[O-:20])[cH:16][c:14]1[CH3:15])=[O:7].[NH:8]1[CH2:9][CH2:10][O:11][CH2:12][CH2:13]1>CCN(C(C)C)C(C)C.CN(C)C(On1nnc2cccnc21)=[N+](C)C.ClCCl.F[PH](F)(F)(F)(F)F.O>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[N:8]2[CH2:9][CH2:10][O:11][CH2:12][CH2:13]2)[c:14]([CH3:15])[cH:16][c:17]1[N+:18](=[O:19])[O-:20]\"},\"mapped_reaction_smiles\":\"O[C:6]([c:5]1[cH:4][c:3]([O:2][CH3:1])[c:17]([N+:18](=[O:19])[O-:20])[cH:16][c:14]1[CH3:15])=[O:7].[NH:8]1[CH2:9][CH2:10][O:11][CH2:12][CH2:13]1>CCN(C(C)C)C(C)C.CN(C)C(On1nnc2cccnc21)=[N+](C)C.ClCCl.F[PH](F)(F)(F)(F)F.O>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[N:8]2[CH2:9][CH2:10][O:11][CH2:12][CH2:13]2)[c:14]([CH3:15])[cH:16][c:17]1[N+:18](=[O:19])[O-:20]\"}",
"reactionStep": {
"id": "sa_d190a729950ef0d45dd91888",
"reactionHash": "0db98564d1e5ef988caaadaa178e7c3b9eb8773c6aa72bc97ceb49b9e28afcbc"
},
"children": [
{
"id": "14350",
"routeId": "sa_7ff98bebb54842ec9885bf0c",
"moleculeId": "sa_39d71c291f7fdf13918cc969",
"parentId": "14349",
"isLeaf": true,
"molecule": {
"id": "sa_39d71c291f7fdf13918cc969",
"inchikey": "YNAVUWVOSKDBBP-UHFFFAOYSA-N",
"smiles": "C1COCCN1"
},
"smiles": "C1COCCN1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "14351",
"routeId": "sa_7ff98bebb54842ec9885bf0c",
"moleculeId": "sa_b4ad2799f355cf7ffb297233",
"parentId": "14349",
"isLeaf": false,
"molecule": {
"id": "sa_b4ad2799f355cf7ffb297233",
"inchikey": "ZGKYHGDVUJUNOW-UHFFFAOYSA-N",
"smiles": "COc1cc(C(=O)O)c(C)cc1[N+](=O)[O-]"
},
"smiles": "COc1cc(C(=O)O)c(C)cc1[N+](=O)[O-]",
"reactionStepId": "sa_5f6d03812ac9db346fb3ca4d",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130157999A1;0692;1382801\",\"rsmi\":\"CC(O)=[O:7].N#[C:6][c:5]1[cH:4][c:3]([O:2][CH3:1])[c:12]([N+:13](=[O:14])[O-:15])[cH:11][c:9]1[CH3:10].O=S(=O)(O)[OH:8]>ClCCl.O>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[OH:8])[c:9]([CH3:10])[cH:11][c:12]1[N+:13](=[O:14])[O-:15]\"},\"mapped_reaction_smiles\":\"CC(O)=[O:7].N#[C:6][c:5]1[cH:4][c:3]([O:2][CH3:1])[c:12]([N+:13](=[O:14])[O-:15])[cH:11][c:9]1[CH3:10].O=S(=O)(O)[OH:8]>ClCCl.O>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[OH:8])[c:9]([CH3:10])[cH:11][c:12]1[N+:13](=[O:14])[O-:15]\"}",
"reactionStep": {
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"reactionHash": "a81ff8b47fee35dca316494a49a8a58cd52e4b771ba8e28301ee82f5ad4be05a"
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"children": [
{
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"routeId": "sa_7ff98bebb54842ec9885bf0c",
"moleculeId": "sa_05249ca5ea0d95fe5b5e933b",
"parentId": "14351",
"isLeaf": false,
"molecule": {
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"inchikey": "NRJWNFQMZBQCRT-UHFFFAOYSA-N",
"smiles": "COc1cc(C#N)c(C)cc1[N+](=O)[O-]"
},
"smiles": "COc1cc(C#N)c(C)cc1[N+](=O)[O-]",
"reactionStepId": "sa_b7464fb70831e52c5cdf94d4",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130157999A1;0690;1382800\",\"rsmi\":\"N[c:5]1[cH:4][c:3]([O:2][CH3:1])[c:11]([N+:12](=[O:13])[O-:14])[cH:10][c:8]1[CH3:9].[CH:6]#[N:7]>CC(C)=O.CCOC(C)=O.Cl.N#C[Cu]C#N.O.O=NO.[Na+].[Na+]>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6]#[N:7])[c:8]([CH3:9])[cH:10][c:11]1[N+:12](=[O:13])[O-:14]\"},\"mapped_reaction_smiles\":\"N[c:5]1[cH:4][c:3]([O:2][CH3:1])[c:11]([N+:12](=[O:13])[O-:14])[cH:10][c:8]1[CH3:9].[CH:6]#[N:7]>CC(C)=O.CCOC(C)=O.Cl.N#C[Cu]C#N.O.O=NO.[Na+].[Na+]>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6]#[N:7])[c:8]([CH3:9])[cH:10][c:11]1[N+:12](=[O:13])[O-:14]\"}",
"reactionStep": {
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"reactionHash": "c945fc5435161ce62ef125ca77def189726d1a2d07c8743332e4e0853f7f5be2"
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"children": [
{
"id": "14353",
"routeId": "sa_7ff98bebb54842ec9885bf0c",
"moleculeId": "sa_5995aff3aeff665a1f3e984d",
"parentId": "14352",
"isLeaf": true,
"molecule": {
"id": "sa_5995aff3aeff665a1f3e984d",
"inchikey": "LELOWRISYMNNSU-UHFFFAOYSA-N",
"smiles": "C#N"
},
"smiles": "C#N",
"reactionStepId": null,
"template": null,
"metadata": null,
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},
{
"id": "14354",
"routeId": "sa_7ff98bebb54842ec9885bf0c",
"moleculeId": "sa_6b5454991ea9a25b7c3549a9",
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"molecule": {
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"inchikey": "PEIGETRPPZVBHT-UHFFFAOYSA-N",
"smiles": "COc1cc(N)c(C)cc1[N+](=O)[O-]"
},
"smiles": "COc1cc(N)c(C)cc1[N+](=O)[O-]",
"reactionStepId": null,
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{
"id": "14355",
"routeId": "sa_7ff98bebb54842ec9885bf0c",
"moleculeId": "sa_a538ca410f1833f7a9788be8",
"parentId": "14351",
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"molecule": {
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"inchikey": "QAOWNCQODCNURD-UHFFFAOYSA-N",
"smiles": "O=S(=O)(O)O"
},
"smiles": "O=S(=O)(O)O",
"reactionStepId": null,
"template": null,
"metadata": null,
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},
{
"id": "14356",
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"parentId": "14351",
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"molecule": {
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"inchikey": "QTBSBXVTEAMEQO-UHFFFAOYSA-N",
"smiles": "CC(=O)O"
},
"smiles": "CC(=O)O",
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"children": []
}
]
}
]
}
]
}
]
}
}