Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CC(Oc1nnc(-c2cc[nH]c(=O)c2)n1C)c1cc(-c2cccc(Cl)c2)on1
InChiKey
YGGDHMSWIMDIPD-UHFFFAOYSA-N
Route Signature
5aef86ae573642aba6b4d41d44c6bc6856e5b66eb6c06d52be66b3497559af70
Synthesis route with 4 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_16879db76f90d1c16fefea66",
"signature": "5aef86ae573642aba6b4d41d44c6bc6856e5b66eb6c06d52be66b3497559af70",
"contentHash": "e07048557a722ce87dfbaf7313c12c5f4fff1e476d4654667e030a5a033a2a30",
"length": 4,
"isConvergent": true
},
"target": {
"id": "sa_d5a7aafe9b62ad03df93197b",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-03018",
"moleculeId": "sa_844d302999e7539628709346",
"smiles": "CC(Oc1nnc(-c2cc[nH]c(=O)c2)n1C)c1cc(-c2cccc(Cl)c2)on1",
"routeLength": 4,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_844d302999e7539628709346",
"inchikey": "YGGDHMSWIMDIPD-UHFFFAOYSA-N",
"smiles": "CC(Oc1nnc(-c2cc[nH]c(=O)c2)n1C)c1cc(-c2cccc(Cl)c2)on1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "10948",
"routeId": "sa_16879db76f90d1c16fefea66",
"moleculeId": "sa_844d302999e7539628709346",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_844d302999e7539628709346",
"inchikey": "YGGDHMSWIMDIPD-UHFFFAOYSA-N",
"smiles": "CC(Oc1nnc(-c2cc[nH]c(=O)c2)n1C)c1cc(-c2cccc(Cl)c2)on1"
},
"smiles": "CC(Oc1nnc(-c2cc[nH]c(=O)c2)n1C)c1cc(-c2cccc(Cl)c2)on1",
"reactionStepId": "sa_f68112edc43ab3817e97690c",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US07772235B2;0376;1001252\",\"rsmi\":\"c1ccc(C[O:11][c:10]2[cH:9][c:8](-[c:7]3[n:6][n:5][c:4]([O:3][CH:2]([CH3:1])[c:17]4[n:18][o:19][c:20](-[c:21]5[cH:22][c:23]([Cl:24])[cH:25][cH:26][cH:27]5)[cH:28]4)[n:15]3[CH3:16])[cH:14][cH:13][n:12]2)cc1>CCO.ClCCl.[Pd]>[CH3:1][CH:2]([O:3][c:4]1[n:5][n:6][c:7](-[c:8]2[cH:9][c:10](=[O:11])[nH:12][cH:13][cH:14]2)[n:15]1[CH3:16])[c:17]1[n:18][o:19][c:20](-[c:21]2[cH:22][c:23]([Cl:24])[cH:25][cH:26][cH:27]2)[cH:28]1\"},\"mapped_reaction_smiles\":\"c1ccc(C[O:11][c:10]2[cH:9][c:8](-[c:7]3[n:6][n:5][c:4]([O:3][CH:2]([CH3:1])[c:17]4[n:18][o:19][c:20](-[c:21]5[cH:22][c:23]([Cl:24])[cH:25][cH:26][cH:27]5)[cH:28]4)[n:15]3[CH3:16])[cH:14][cH:13][n:12]2)cc1>CCO.ClCCl.[Pd]>[CH3:1][CH:2]([O:3][c:4]1[n:5][n:6][c:7](-[c:8]2[cH:9][c:10](=[O:11])[nH:12][cH:13][cH:14]2)[n:15]1[CH3:16])[c:17]1[n:18][o:19][c:20](-[c:21]2[cH:22][c:23]([Cl:24])[cH:25][cH:26][cH:27]2)[cH:28]1\"}",
"reactionStep": {
"id": "sa_f68112edc43ab3817e97690c",
"reactionHash": "0aa8c5583c2e8ad57df5d2757ba76d572fc09c5c11fa68677e08db6d8d701105"
},
"children": [
{
"id": "10949",
"routeId": "sa_16879db76f90d1c16fefea66",
"moleculeId": "sa_3a69444cfab0ac6ecc77f4e9",
"parentId": "10948",
"isLeaf": false,
"molecule": {
"id": "sa_3a69444cfab0ac6ecc77f4e9",
"inchikey": "WUPDUHQGDYEYAJ-UHFFFAOYSA-N",
"smiles": "CC(Oc1nnc(-c2ccnc(OCc3ccccc3)c2)n1C)c1cc(-c2cccc(Cl)c2)on1"
},
"smiles": "CC(Oc1nnc(-c2ccnc(OCc3ccccc3)c2)n1C)c1cc(-c2cccc(Cl)c2)on1",
"reactionStepId": "sa_870d7a93dc67f259dfaf11fd",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US07772235B2;0366;1001250\",\"rsmi\":\"CS(=O)(=O)[c:4]1[n:5][n:6][c:7](-[c:8]2[cH:9][c:10]([O:11][CH2:12][c:13]3[cH:14][cH:15][cH:16][cH:17][cH:18]3)[n:19][cH:20][cH:21]2)[n:22]1[CH3:23].[CH3:1][CH:2]([OH:3])[c:24]1[n:25][o:26][c:27](-[c:28]2[cH:29][c:30]([Cl:31])[cH:32][cH:33][cH:34]2)[cH:35]1>O=C(O)O.[Cs+].[Cs+]>[CH3:1][CH:2]([O:3][c:4]1[n:5][n:6][c:7](-[c:8]2[cH:9][c:10]([O:11][CH2:12][c:13]3[cH:14][cH:15][cH:16][cH:17][cH:18]3)[n:19][cH:20][cH:21]2)[n:22]1[CH3:23])[c:24]1[n:25][o:26][c:27](-[c:28]2[cH:29][c:30]([Cl:31])[cH:32][cH:33][cH:34]2)[cH:35]1\"},\"mapped_reaction_smiles\":\"CS(=O)(=O)[c:4]1[n:5][n:6][c:7](-[c:8]2[cH:9][c:10]([O:11][CH2:12][c:13]3[cH:14][cH:15][cH:16][cH:17][cH:18]3)[n:19][cH:20][cH:21]2)[n:22]1[CH3:23].[CH3:1][CH:2]([OH:3])[c:24]1[n:25][o:26][c:27](-[c:28]2[cH:29][c:30]([Cl:31])[cH:32][cH:33][cH:34]2)[cH:35]1>O=C(O)O.[Cs+].[Cs+]>[CH3:1][CH:2]([O:3][c:4]1[n:5][n:6][c:7](-[c:8]2[cH:9][c:10]([O:11][CH2:12][c:13]3[cH:14][cH:15][cH:16][cH:17][cH:18]3)[n:19][cH:20][cH:21]2)[n:22]1[CH3:23])[c:24]1[n:25][o:26][c:27](-[c:28]2[cH:29][c:30]([Cl:31])[cH:32][cH:33][cH:34]2)[cH:35]1\"}",
"reactionStep": {
"id": "sa_870d7a93dc67f259dfaf11fd",
"reactionHash": "d53f56d65f270920c15f59aeff5e53ba3ed2c7909385848a3ed470607c278600"
},
"children": [
{
"id": "10950",
"routeId": "sa_16879db76f90d1c16fefea66",
"moleculeId": "sa_cb038541bc57a9997e302051",
"parentId": "10949",
"isLeaf": false,
"molecule": {
"id": "sa_cb038541bc57a9997e302051",
"inchikey": "FOLGHHVVTIHOLE-UHFFFAOYSA-N",
"smiles": "CC(O)c1cc(-c2cccc(Cl)c2)on1"
},
"smiles": "CC(O)c1cc(-c2cccc(Cl)c2)on1",
"reactionStepId": "sa_31e73137a390e044cbc81a7e",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US07772235B2;0238;1001222\",\"rsmi\":\"[CH3:1][C:2](=[O:3])[c:4]1[n:5][o:6][c:7](-[c:8]2[cH:9][c:10]([Cl:11])[cH:12][cH:13][cH:14]2)[cH:15]1>CO.B.[Na+]>[CH3:1][CH:2]([OH:3])[c:4]1[n:5][o:6][c:7](-[c:8]2[cH:9][c:10]([Cl:11])[cH:12][cH:13][cH:14]2)[cH:15]1\"},\"mapped_reaction_smiles\":\"[CH3:1][C:2](=[O:3])[c:4]1[n:5][o:6][c:7](-[c:8]2[cH:9][c:10]([Cl:11])[cH:12][cH:13][cH:14]2)[cH:15]1>CO.B.[Na+]>[CH3:1][CH:2]([OH:3])[c:4]1[n:5][o:6][c:7](-[c:8]2[cH:9][c:10]([Cl:11])[cH:12][cH:13][cH:14]2)[cH:15]1\"}",
"reactionStep": {
"id": "sa_31e73137a390e044cbc81a7e",
"reactionHash": "2185a3a15ca15e6e2aa8db6454fbf53a6c23b23e5ce9b35382fdf0196e6c1847"
},
"children": [
{
"id": "10951",
"routeId": "sa_16879db76f90d1c16fefea66",
"moleculeId": "sa_009fe73ff5323cbf3f02f105",
"parentId": "10950",
"isLeaf": true,
"molecule": {
"id": "sa_009fe73ff5323cbf3f02f105",
"inchikey": "UHSJRZGDQIGKGO-UHFFFAOYSA-N",
"smiles": "CC(=O)c1cc(-c2cccc(Cl)c2)on1"
},
"smiles": "CC(=O)c1cc(-c2cccc(Cl)c2)on1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "10952",
"routeId": "sa_16879db76f90d1c16fefea66",
"moleculeId": "sa_cbdf26d3ff76a4ae1ca0e33a",
"parentId": "10949",
"isLeaf": false,
"molecule": {
"id": "sa_cbdf26d3ff76a4ae1ca0e33a",
"inchikey": "QWWDUYBNUCKRGC-UHFFFAOYSA-N",
"smiles": "Cn1c(-c2ccnc(OCc3ccccc3)c2)nnc1S(C)(=O)=O"
},
"smiles": "Cn1c(-c2ccnc(OCc3ccccc3)c2)nnc1S(C)(=O)=O",
"reactionStepId": "sa_25190ef3fde49552153d4f33",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US07772235B2;0348;1001245\",\"rsmi\":\"Br[CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH3:1][n:2]1[c:3](-[c:4]2[cH:5][c:6](=[O:7])[nH:15][cH:16][cH:17]2)[n:18][n:19][c:20]1[S:21]([CH3:22])(=[O:23])=[O:24]>O=C(O)O.[Ag+].[Ag+]>[CH3:1][n:2]1[c:3](-[c:4]2[cH:5][c:6]([O:7][CH2:8][c:9]3[cH:10][cH:11][cH:12][cH:13][cH:14]3)[n:15][cH:16][cH:17]2)[n:18][n:19][c:20]1[S:21]([CH3:22])(=[O:23])=[O:24]\"},\"mapped_reaction_smiles\":\"Br[CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH3:1][n:2]1[c:3](-[c:4]2[cH:5][c:6](=[O:7])[nH:15][cH:16][cH:17]2)[n:18][n:19][c:20]1[S:21]([CH3:22])(=[O:23])=[O:24]>O=C(O)O.[Ag+].[Ag+]>[CH3:1][n:2]1[c:3](-[c:4]2[cH:5][c:6]([O:7][CH2:8][c:9]3[cH:10][cH:11][cH:12][cH:13][cH:14]3)[n:15][cH:16][cH:17]2)[n:18][n:19][c:20]1[S:21]([CH3:22])(=[O:23])=[O:24]\"}",
"reactionStep": {
"id": "sa_25190ef3fde49552153d4f33",
"reactionHash": "495ca16fc6d32e68c89c8dcf3c3d574246c712e895a6d69dd65e1c84a9f4f76e"
},
"children": [
{
"id": "10953",
"routeId": "sa_16879db76f90d1c16fefea66",
"moleculeId": "sa_4ff2e4de9d80150de333c065",
"parentId": "10952",
"isLeaf": true,
"molecule": {
"id": "sa_4ff2e4de9d80150de333c065",
"inchikey": "AGEZXYOZHKGVCM-UHFFFAOYSA-N",
"smiles": "BrCc1ccccc1"
},
"smiles": "BrCc1ccccc1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "10954",
"routeId": "sa_16879db76f90d1c16fefea66",
"moleculeId": "sa_7797eead9d18ac4a5b9fd751",
"parentId": "10952",
"isLeaf": false,
"molecule": {
"id": "sa_7797eead9d18ac4a5b9fd751",
"inchikey": "BMYBHKLAZPHMAP-UHFFFAOYSA-N",
"smiles": "Cn1c(-c2cc[nH]c(=O)c2)nnc1S(C)(=O)=O"
},
"smiles": "Cn1c(-c2cc[nH]c(=O)c2)nnc1S(C)(=O)=O",
"reactionStepId": "sa_d7c16f3a313294e26bcf1f66",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US07772235B2;0337;1001244\",\"rsmi\":\"C[O:7][c:6]1[cH:5][c:4](-[c:3]2[n:2]([CH3:1])[c:13]([S:14]([CH3:15])(=[O:16])=[O:17])[n:12][n:11]2)[cH:10][cH:9][n:8]1>Br.CC(=O)O.CCO>[CH3:1][n:2]1[c:3](-[c:4]2[cH:5][c:6](=[O:7])[nH:8][cH:9][cH:10]2)[n:11][n:12][c:13]1[S:14]([CH3:15])(=[O:16])=[O:17]\"},\"mapped_reaction_smiles\":\"C[O:7][c:6]1[cH:5][c:4](-[c:3]2[n:2]([CH3:1])[c:13]([S:14]([CH3:15])(=[O:16])=[O:17])[n:12][n:11]2)[cH:10][cH:9][n:8]1>Br.CC(=O)O.CCO>[CH3:1][n:2]1[c:3](-[c:4]2[cH:5][c:6](=[O:7])[nH:8][cH:9][cH:10]2)[n:11][n:12][c:13]1[S:14]([CH3:15])(=[O:16])=[O:17]\"}",
"reactionStep": {
"id": "sa_d7c16f3a313294e26bcf1f66",
"reactionHash": "9ca3548fc1b175c5ae1ab1e974aa8b85a5e70bc17c7e2520cc2cc55a951f725a"
},
"children": [
{
"id": "10955",
"routeId": "sa_16879db76f90d1c16fefea66",
"moleculeId": "sa_26518c76bd355400509f6286",
"parentId": "10954",
"isLeaf": true,
"molecule": {
"id": "sa_26518c76bd355400509f6286",
"inchikey": "XAKCXLMMOPJCIS-UHFFFAOYSA-N",
"smiles": "COc1cc(-c2nnc(S(C)(=O)=O)n2C)ccn1"
},
"smiles": "COc1cc(-c2nnc(S(C)(=O)=O)n2C)ccn1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
]
}
]
}
}