Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CC(C)Oc1ccc(-c2cc(COc3ccc(C#N)cc3)no2)cc1Cl
InChiKey
SLMNIRNDHDAHTB-UHFFFAOYSA-N
Route Signature
644406cddb565958b543af37ffc1dbe401deaa4c6e4f8680453ae6b818e3c5da
Synthesis route with 5 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_cd317a2987108405449130fe",
"signature": "644406cddb565958b543af37ffc1dbe401deaa4c6e4f8680453ae6b818e3c5da",
"contentHash": "4959a13de403ec14601bd36b461eb3d5570d0636852c79e075074f040d99ca0f",
"length": 5,
"isConvergent": false
},
"target": {
"id": "sa_a5fab210a48db86cca8cbc81",
"benchmarkSetId": "f925e688d731a0ad4e3aa6a505df094f6d3ca64ce3facc312bc5f64731921b33",
"targetId": "n5-05036",
"moleculeId": "sa_075cba80b5c90346316eb6c5",
"smiles": "CC(C)Oc1ccc(-c2cc(COc3ccc(C#N)cc3)no2)cc1Cl",
"routeLength": 5,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_075cba80b5c90346316eb6c5",
"inchikey": "SLMNIRNDHDAHTB-UHFFFAOYSA-N",
"smiles": "CC(C)Oc1ccc(-c2cc(COc3ccc(C#N)cc3)no2)cc1Cl"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "7512",
"routeId": "sa_cd317a2987108405449130fe",
"moleculeId": "sa_075cba80b5c90346316eb6c5",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_075cba80b5c90346316eb6c5",
"inchikey": "SLMNIRNDHDAHTB-UHFFFAOYSA-N",
"smiles": "CC(C)Oc1ccc(-c2cc(COc3ccc(C#N)cc3)no2)cc1Cl"
},
"smiles": "CC(C)Oc1ccc(-c2cc(COc3ccc(C#N)cc3)no2)cc1Cl",
"reactionStepId": "sa_44424b2e9b10fd576928a0a1",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20090069288A1;0509;677367\",\"rsmi\":\"O[c:15]1[cH:16][cH:17][c:18]([C:19]#[N:20])[cH:21][cH:22]1.[CH3:1][CH:2]([CH3:3])[O:4][c:5]1[c:6]([Cl:7])[cH:8][c:9](-[c:10]2[cH:11][c:12]([CH2:13][OH:14])[n:23][o:24]2)[cH:25][cH:26]1>C1CCOC1.CC(C)(C)OC(=O)N=NC(=O)OC(C)(C)C.c1ccc(P(c2ccccc2)c2ccccc2)cc1>[CH3:1][CH:2]([CH3:3])[O:4][c:5]1[c:6]([Cl:7])[cH:8][c:9](-[c:10]2[cH:11][c:12]([CH2:13][O:14][c:15]3[cH:16][cH:17][c:18]([C:19]#[N:20])[cH:21][cH:22]3)[n:23][o:24]2)[cH:25][cH:26]1\"},\"mapped_reaction_smiles\":\"O[c:15]1[cH:16][cH:17][c:18]([C:19]#[N:20])[cH:21][cH:22]1.[CH3:1][CH:2]([CH3:3])[O:4][c:5]1[c:6]([Cl:7])[cH:8][c:9](-[c:10]2[cH:11][c:12]([CH2:13][OH:14])[n:23][o:24]2)[cH:25][cH:26]1>C1CCOC1.CC(C)(C)OC(=O)N=NC(=O)OC(C)(C)C.c1ccc(P(c2ccccc2)c2ccccc2)cc1>[CH3:1][CH:2]([CH3:3])[O:4][c:5]1[c:6]([Cl:7])[cH:8][c:9](-[c:10]2[cH:11][c:12]([CH2:13][O:14][c:15]3[cH:16][cH:17][c:18]([C:19]#[N:20])[cH:21][cH:22]3)[n:23][o:24]2)[cH:25][cH:26]1\"}",
"reactionStep": {
"id": "sa_44424b2e9b10fd576928a0a1",
"reactionHash": "4bcddd8c8b19483f2e93a6ce4be21bc7db8fb23a94e1c979689fe26b6c43d78e"
},
"children": [
{
"id": "7513",
"routeId": "sa_cd317a2987108405449130fe",
"moleculeId": "sa_450c8f04c99bb2e94a7b84f2",
"parentId": "7512",
"isLeaf": true,
"molecule": {
"id": "sa_450c8f04c99bb2e94a7b84f2",
"inchikey": "CVNOWLNNPYYEOH-UHFFFAOYSA-N",
"smiles": "N#Cc1ccc(O)cc1"
},
"smiles": "N#Cc1ccc(O)cc1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "7514",
"routeId": "sa_cd317a2987108405449130fe",
"moleculeId": "sa_bc5676d08139d760f5b56641",
"parentId": "7512",
"isLeaf": false,
"molecule": {
"id": "sa_bc5676d08139d760f5b56641",
"inchikey": "XRLXEUBLHFGMAR-UHFFFAOYSA-N",
"smiles": "CC(C)Oc1ccc(-c2cc(CO)no2)cc1Cl"
},
"smiles": "CC(C)Oc1ccc(-c2cc(CO)no2)cc1Cl",
"reactionStepId": "sa_ed4b36b50d45229f51a816f4",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20090069288A1;0493;677360\",\"rsmi\":\"CCO[C:13]([c:12]1[cH:11][c:10](-[c:9]2[cH:8][c:6]([Cl:7])[c:5]([O:4][CH:2]([CH3:1])[CH3:3])[cH:18][cH:17]2)[o:16][n:15]1)=[O:14]>C1CCOC1.[Al+3].[HH].[HH].[HH].[HH].[Li+]>[CH3:1][CH:2]([CH3:3])[O:4][c:5]1[c:6]([Cl:7])[cH:8][c:9](-[c:10]2[cH:11][c:12]([CH2:13][OH:14])[n:15][o:16]2)[cH:17][cH:18]1\"},\"mapped_reaction_smiles\":\"CCO[C:13]([c:12]1[cH:11][c:10](-[c:9]2[cH:8][c:6]([Cl:7])[c:5]([O:4][CH:2]([CH3:1])[CH3:3])[cH:18][cH:17]2)[o:16][n:15]1)=[O:14]>C1CCOC1.[Al+3].[HH].[HH].[HH].[HH].[Li+]>[CH3:1][CH:2]([CH3:3])[O:4][c:5]1[c:6]([Cl:7])[cH:8][c:9](-[c:10]2[cH:11][c:12]([CH2:13][OH:14])[n:15][o:16]2)[cH:17][cH:18]1\"}",
"reactionStep": {
"id": "sa_ed4b36b50d45229f51a816f4",
"reactionHash": "436dc7ef2ae13e89c3349703a73c23921d91295d0f21f31691974dc99ed2c22e"
},
"children": [
{
"id": "7515",
"routeId": "sa_cd317a2987108405449130fe",
"moleculeId": "sa_1544c00220912eb425404847",
"parentId": "7514",
"isLeaf": false,
"molecule": {
"id": "sa_1544c00220912eb425404847",
"inchikey": "IEVIWTHHVBGATL-UHFFFAOYSA-N",
"smiles": "CCOC(=O)c1cc(-c2ccc(OC(C)C)c(Cl)c2)on1"
},
"smiles": "CCOC(=O)c1cc(-c2ccc(OC(C)C)c(Cl)c2)on1",
"reactionStepId": "sa_87f79010a5fc47c30c9326c5",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20090069288A1;0347;677315\",\"rsmi\":\"O=[C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:21][C:9](=O)[c:10]1[cH:11][c:12]([Cl:13])[c:14]([O:15][CH:16]([CH3:17])[CH3:18])[cH:19][cH:20]1.[NH2:7][OH:8]>CCO.Cl>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[n:7][o:8][c:9](-[c:10]2[cH:11][c:12]([Cl:13])[c:14]([O:15][CH:16]([CH3:17])[CH3:18])[cH:19][cH:20]2)[cH:21]1\"},\"mapped_reaction_smiles\":\"O=[C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:21][C:9](=O)[c:10]1[cH:11][c:12]([Cl:13])[c:14]([O:15][CH:16]([CH3:17])[CH3:18])[cH:19][cH:20]1.[NH2:7][OH:8]>CCO.Cl>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[n:7][o:8][c:9](-[c:10]2[cH:11][c:12]([Cl:13])[c:14]([O:15][CH:16]([CH3:17])[CH3:18])[cH:19][cH:20]2)[cH:21]1\"}",
"reactionStep": {
"id": "sa_87f79010a5fc47c30c9326c5",
"reactionHash": "cedba3046d5cd0dfde7c7c66c2d00fe1e6cea69184acbc48c3acfe47db91f8ac"
},
"children": [
{
"id": "7516",
"routeId": "sa_cd317a2987108405449130fe",
"moleculeId": "sa_04a18e3f07bde82ca29399ee",
"parentId": "7515",
"isLeaf": true,
"molecule": {
"id": "sa_04a18e3f07bde82ca29399ee",
"inchikey": "AVXURJPOCDRRFD-UHFFFAOYSA-N",
"smiles": "NO"
},
"smiles": "NO",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "7517",
"routeId": "sa_cd317a2987108405449130fe",
"moleculeId": "sa_107fa05ea18d553bd96bc9d8",
"parentId": "7515",
"isLeaf": false,
"molecule": {
"id": "sa_107fa05ea18d553bd96bc9d8",
"inchikey": "REIFWJIXUOFTFY-UHFFFAOYSA-N",
"smiles": "CCOC(=O)C(=O)CC(=O)c1ccc(OC(C)C)c(Cl)c1"
},
"smiles": "CCOC(=O)C(=O)CC(=O)c1ccc(OC(C)C)c(Cl)c1",
"reactionStepId": "sa_412fc4341e28ee743c4b5f0d",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20090069288A1;0345;677314\",\"rsmi\":\"CCO[C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])=[O:7].[CH3:8][C:9](=[O:10])[c:11]1[cH:12][c:13]([Cl:14])[c:15]([O:16][CH:17]([CH3:18])[CH3:19])[cH:20][cH:21]1>CCO.CCOC(C)=O.[Na]>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6](=[O:7])[CH2:8][C:9](=[O:10])[c:11]1[cH:12][c:13]([Cl:14])[c:15]([O:16][CH:17]([CH3:18])[CH3:19])[cH:20][cH:21]1\"},\"mapped_reaction_smiles\":\"CCO[C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])=[O:7].[CH3:8][C:9](=[O:10])[c:11]1[cH:12][c:13]([Cl:14])[c:15]([O:16][CH:17]([CH3:18])[CH3:19])[cH:20][cH:21]1>CCO.CCOC(C)=O.[Na]>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6](=[O:7])[CH2:8][C:9](=[O:10])[c:11]1[cH:12][c:13]([Cl:14])[c:15]([O:16][CH:17]([CH3:18])[CH3:19])[cH:20][cH:21]1\"}",
"reactionStep": {
"id": "sa_412fc4341e28ee743c4b5f0d",
"reactionHash": "77bf4783f65a0e359f0f1ee43f7a522a4c4293d790161aca413c0e93b48247b9"
},
"children": [
{
"id": "7518",
"routeId": "sa_cd317a2987108405449130fe",
"moleculeId": "sa_ce4c38e996ab53c4caa548e1",
"parentId": "7517",
"isLeaf": false,
"molecule": {
"id": "sa_ce4c38e996ab53c4caa548e1",
"inchikey": "KTKDBLMLMCAZLT-UHFFFAOYSA-N",
"smiles": "CC(=O)c1ccc(OC(C)C)c(Cl)c1"
},
"smiles": "CC(=O)c1ccc(OC(C)C)c(Cl)c1",
"reactionStepId": "sa_79bca6c81b875a148348ec8b",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20090069288A1;0343;677313\",\"rsmi\":\"O[CH:10]([CH3:11])[CH3:12].[CH3:1][C:2](=[O:3])[c:4]1[cH:5][c:6]([Cl:7])[c:8]([OH:9])[cH:13][cH:14]1>C1CCOC1.CC(C)OC(=O)/N=N/C(=O)OC(C)C.c1ccc(P(c2ccccc2)c2ccccc2)cc1>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][c:6]([Cl:7])[c:8]([O:9][CH:10]([CH3:11])[CH3:12])[cH:13][cH:14]1\"},\"mapped_reaction_smiles\":\"O[CH:10]([CH3:11])[CH3:12].[CH3:1][C:2](=[O:3])[c:4]1[cH:5][c:6]([Cl:7])[c:8]([OH:9])[cH:13][cH:14]1>C1CCOC1.CC(C)OC(=O)/N=N/C(=O)OC(C)C.c1ccc(P(c2ccccc2)c2ccccc2)cc1>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][c:6]([Cl:7])[c:8]([O:9][CH:10]([CH3:11])[CH3:12])[cH:13][cH:14]1\"}",
"reactionStep": {
"id": "sa_79bca6c81b875a148348ec8b",
"reactionHash": "a422a85ebc53df92a3c958da8cf41d5ca52e44438159749bf1d2c19d8e04489a"
},
"children": [
{
"id": "7519",
"routeId": "sa_cd317a2987108405449130fe",
"moleculeId": "sa_b992a4dc034b2a04512819cb",
"parentId": "7518",
"isLeaf": true,
"molecule": {
"id": "sa_b992a4dc034b2a04512819cb",
"inchikey": "GMTSPBYBJKGPJF-UHFFFAOYSA-N",
"smiles": "CC(=O)c1ccc(O)c(Cl)c1"
},
"smiles": "CC(=O)c1ccc(O)c(Cl)c1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "7520",
"routeId": "sa_cd317a2987108405449130fe",
"moleculeId": "sa_686dd003386da742d95a15d8",
"parentId": "7518",
"isLeaf": true,
"molecule": {
"id": "sa_686dd003386da742d95a15d8",
"inchikey": "KFZMGEQAYNKOFK-UHFFFAOYSA-N",
"smiles": "CC(C)O"
},
"smiles": "CC(C)O",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "7521",
"routeId": "sa_cd317a2987108405449130fe",
"moleculeId": "sa_ab0a3cf4ca71164a04c8f94b",
"parentId": "7517",
"isLeaf": true,
"molecule": {
"id": "sa_ab0a3cf4ca71164a04c8f94b",
"inchikey": "WYACBZDAHNBPPB-UHFFFAOYSA-N",
"smiles": "CCOC(=O)C(=O)OCC"
},
"smiles": "CCOC(=O)C(=O)OCC",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
]
}
]
}
}