Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
C[C@H](Nc1ncnc(N)c1C#N)c1nc2ccc(F)c(-c3ccccc3)c2n1C1CC1
InChiKey
OWOHZJNUUOEFJM-ZDUSSCGKSA-N
Route Signature
a5eb5fa619b65d3863c890d39be7cc0f82b9808fe90e15d95ec6229d397ca615
Synthesis route with 6 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_61d0aa6dd8ab91c11af09f94",
"signature": "a5eb5fa619b65d3863c890d39be7cc0f82b9808fe90e15d95ec6229d397ca615",
"contentHash": "ec2135d9bd28e782004257311b055532ecac1d3cd0423353e914b0db4f383e34",
"length": 6,
"isConvergent": false
},
"target": {
"id": "sa_86660ce7cb41f3f3a9e73e04",
"benchmarkSetId": "f925e688d731a0ad4e3aa6a505df094f6d3ca64ce3facc312bc5f64731921b33",
"targetId": "n5-00248",
"moleculeId": "sa_ab466a35d60c0360a7ae6270",
"smiles": "C[C@H](Nc1ncnc(N)c1C#N)c1nc2ccc(F)c(-c3ccccc3)c2n1C1CC1",
"routeLength": 6,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_ab466a35d60c0360a7ae6270",
"inchikey": "OWOHZJNUUOEFJM-ZDUSSCGKSA-N",
"smiles": "C[C@H](Nc1ncnc(N)c1C#N)c1nc2ccc(F)c(-c3ccccc3)c2n1C1CC1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "3711",
"routeId": "sa_61d0aa6dd8ab91c11af09f94",
"moleculeId": "sa_ab466a35d60c0360a7ae6270",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_ab466a35d60c0360a7ae6270",
"inchikey": "OWOHZJNUUOEFJM-ZDUSSCGKSA-N",
"smiles": "C[C@H](Nc1ncnc(N)c1C#N)c1nc2ccc(F)c(-c3ccccc3)c2n1C1CC1"
},
"smiles": "C[C@H](Nc1ncnc(N)c1C#N)c1nc2ccc(F)c(-c3ccccc3)c2n1C1CC1",
"reactionStepId": "sa_6036c6949675cfdc6eec985c",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20120202785A1;1728;1251832\",\"rsmi\":\"Br[c:17]1[c:16]2[c:15]([n:14][c:13]([C@H:2]([CH3:1])[NH:3][c:4]3[c:5]([C:6]#[N:7])[c:8]([NH2:9])[n:10][cH:11][n:12]3)[n:28]2[CH:29]2[CH2:30][CH2:31]2)[cH:27][cH:26][c:24]1[F:25].OB(O)[c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1>C1COCCO1.O.O=C(O)O.[Cs+].[Cs+].c1ccc([PH](c2ccccc2)(c2ccccc2)[Pd]([PH](c2ccccc2)(c2ccccc2)c2ccccc2)([PH](c2ccccc2)(c2ccccc2)c2ccccc2)[PH](c2ccccc2)(c2ccccc2)c2ccccc2)cc1>[CH3:1][C@H:2]([NH:3][c:4]1[c:5]([C:6]#[N:7])[c:8]([NH2:9])[n:10][cH:11][n:12]1)[c:13]1[n:14][c:15]2[c:16]([c:17](-[c:18]3[cH:19][cH:20][cH:21][cH:22][cH:23]3)[c:24]([F:25])[cH:26][cH:27]2)[n:28]1[CH:29]1[CH2:30][CH2:31]1\"},\"mapped_reaction_smiles\":\"Br[c:17]1[c:16]2[c:15]([n:14][c:13]([C@H:2]([CH3:1])[NH:3][c:4]3[c:5]([C:6]#[N:7])[c:8]([NH2:9])[n:10][cH:11][n:12]3)[n:28]2[CH:29]2[CH2:30][CH2:31]2)[cH:27][cH:26][c:24]1[F:25].OB(O)[c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1>C1COCCO1.O.O=C(O)O.[Cs+].[Cs+].c1ccc([PH](c2ccccc2)(c2ccccc2)[Pd]([PH](c2ccccc2)(c2ccccc2)c2ccccc2)([PH](c2ccccc2)(c2ccccc2)c2ccccc2)[PH](c2ccccc2)(c2ccccc2)c2ccccc2)cc1>[CH3:1][C@H:2]([NH:3][c:4]1[c:5]([C:6]#[N:7])[c:8]([NH2:9])[n:10][cH:11][n:12]1)[c:13]1[n:14][c:15]2[c:16]([c:17](-[c:18]3[cH:19][cH:20][cH:21][cH:22][cH:23]3)[c:24]([F:25])[cH:26][cH:27]2)[n:28]1[CH:29]1[CH2:30][CH2:31]1\"}",
"reactionStep": {
"id": "sa_6036c6949675cfdc6eec985c",
"reactionHash": "4dda9c0d921234f9761a33856adcdee6d1e4987f746a27ce4d536757979621cd"
},
"children": [
{
"id": "3712",
"routeId": "sa_61d0aa6dd8ab91c11af09f94",
"moleculeId": "sa_05364e99571ecb363666a42f",
"parentId": "3711",
"isLeaf": true,
"molecule": {
"id": "sa_05364e99571ecb363666a42f",
"inchikey": "HXITXNWTGFUOAU-UHFFFAOYSA-N",
"smiles": "OB(O)c1ccccc1"
},
"smiles": "OB(O)c1ccccc1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "3713",
"routeId": "sa_61d0aa6dd8ab91c11af09f94",
"moleculeId": "sa_e5134f0e54df540b4db86e8a",
"parentId": "3711",
"isLeaf": false,
"molecule": {
"id": "sa_e5134f0e54df540b4db86e8a",
"inchikey": "SQTNXRSMFWYVPI-QMMMGPOBSA-N",
"smiles": "C[C@H](Nc1ncnc(N)c1C#N)c1nc2ccc(F)c(Br)c2n1C1CC1"
},
"smiles": "C[C@H](Nc1ncnc(N)c1C#N)c1nc2ccc(F)c(Br)c2n1C1CC1",
"reactionStepId": "sa_85a130af52232857e837071b",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20120202785A1;1708;1251812\",\"rsmi\":\"Cl[c:4]1[c:5]([C:6]#[N:7])[c:8]([NH2:9])[n:10][cH:11][n:12]1.[CH3:1][C@H:2]([NH2:3])[c:13]1[n:14][c:15]2[c:16]([c:17]([Br:18])[c:19]([F:20])[cH:21][cH:22]2)[n:23]1[CH:24]1[CH2:25][CH2:26]1>CC(C)O.CCN(C(C)C)C(C)C.CO>[CH3:1][C@H:2]([NH:3][c:4]1[c:5]([C:6]#[N:7])[c:8]([NH2:9])[n:10][cH:11][n:12]1)[c:13]1[n:14][c:15]2[c:16]([c:17]([Br:18])[c:19]([F:20])[cH:21][cH:22]2)[n:23]1[CH:24]1[CH2:25][CH2:26]1\"},\"mapped_reaction_smiles\":\"Cl[c:4]1[c:5]([C:6]#[N:7])[c:8]([NH2:9])[n:10][cH:11][n:12]1.[CH3:1][C@H:2]([NH2:3])[c:13]1[n:14][c:15]2[c:16]([c:17]([Br:18])[c:19]([F:20])[cH:21][cH:22]2)[n:23]1[CH:24]1[CH2:25][CH2:26]1>CC(C)O.CCN(C(C)C)C(C)C.CO>[CH3:1][C@H:2]([NH:3][c:4]1[c:5]([C:6]#[N:7])[c:8]([NH2:9])[n:10][cH:11][n:12]1)[c:13]1[n:14][c:15]2[c:16]([c:17]([Br:18])[c:19]([F:20])[cH:21][cH:22]2)[n:23]1[CH:24]1[CH2:25][CH2:26]1\"}",
"reactionStep": {
"id": "sa_85a130af52232857e837071b",
"reactionHash": "8d8b25146bfc924a24e6fe0055f006c8459b4b2307e57b821f75bfce58d0fee9"
},
"children": [
{
"id": "3714",
"routeId": "sa_61d0aa6dd8ab91c11af09f94",
"moleculeId": "sa_93eb773d73da04b9c6a0bb33",
"parentId": "3713",
"isLeaf": false,
"molecule": {
"id": "sa_93eb773d73da04b9c6a0bb33",
"inchikey": "ACYQYEBPGYXFGG-LURJTMIESA-N",
"smiles": "C[C@H](N)c1nc2ccc(F)c(Br)c2n1C1CC1"
},
"smiles": "C[C@H](N)c1nc2ccc(F)c(Br)c2n1C1CC1",
"reactionStepId": "sa_03cc153b4820d80b3e3f5990",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20120202785A1;1143;1251496\",\"rsmi\":\"CC(C)(C)OC(=O)[NH:3][C@@H:2]([CH3:1])[c:4]1[n:5][c:6]2[c:7]([c:8]([Br:9])[c:10]([F:11])[cH:12][cH:13]2)[n:14]1[CH:15]1[CH2:16][CH2:17]1>CO.ClCCl.O=C(O)C(F)(F)F>[CH3:1][C@H:2]([NH2:3])[c:4]1[n:5][c:6]2[c:7]([c:8]([Br:9])[c:10]([F:11])[cH:12][cH:13]2)[n:14]1[CH:15]1[CH2:16][CH2:17]1\"},\"mapped_reaction_smiles\":\"CC(C)(C)OC(=O)[NH:3][C@@H:2]([CH3:1])[c:4]1[n:5][c:6]2[c:7]([c:8]([Br:9])[c:10]([F:11])[cH:12][cH:13]2)[n:14]1[CH:15]1[CH2:16][CH2:17]1>CO.ClCCl.O=C(O)C(F)(F)F>[CH3:1][C@H:2]([NH2:3])[c:4]1[n:5][c:6]2[c:7]([c:8]([Br:9])[c:10]([F:11])[cH:12][cH:13]2)[n:14]1[CH:15]1[CH2:16][CH2:17]1\"}",
"reactionStep": {
"id": "sa_03cc153b4820d80b3e3f5990",
"reactionHash": "a802b48039614864d3403b7b29cdb413c234409bc70e42ea0c445e23f07a687e"
},
"children": [
{
"id": "3715",
"routeId": "sa_61d0aa6dd8ab91c11af09f94",
"moleculeId": "sa_3dc5dcfdb5920ad00ffd4cb8",
"parentId": "3714",
"isLeaf": false,
"molecule": {
"id": "sa_3dc5dcfdb5920ad00ffd4cb8",
"inchikey": "HOBWZSZZJKNBEA-VIFPVBQESA-N",
"smiles": "C[C@H](NC(=O)OC(C)(C)C)c1nc2ccc(F)c(Br)c2n1C1CC1"
},
"smiles": "C[C@H](NC(=O)OC(C)(C)C)c1nc2ccc(F)c(Br)c2n1C1CC1",
"reactionStepId": "sa_61f06b8a366e418666fece9b",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20120202785A1;1141;1251495\",\"rsmi\":\"O=[C:11]([C@H:2]([CH3:1])[NH:3][C:4](=[O:5])[O:6][C:7]([CH3:8])([CH3:9])[CH3:10])[NH:12][c:13]1[c:14]([NH:21][CH:22]2[CH2:23][CH2:24]2)[c:15]([Br:16])[c:17]([F:18])[cH:19][cH:20]1>CC(=O)O>[CH3:1][C@H:2]([NH:3][C:4](=[O:5])[O:6][C:7]([CH3:8])([CH3:9])[CH3:10])[c:11]1[n:12][c:13]2[c:14]([c:15]([Br:16])[c:17]([F:18])[cH:19][cH:20]2)[n:21]1[CH:22]1[CH2:23][CH2:24]1\"},\"mapped_reaction_smiles\":\"O=[C:11]([C@H:2]([CH3:1])[NH:3][C:4](=[O:5])[O:6][C:7]([CH3:8])([CH3:9])[CH3:10])[NH:12][c:13]1[c:14]([NH:21][CH:22]2[CH2:23][CH2:24]2)[c:15]([Br:16])[c:17]([F:18])[cH:19][cH:20]1>CC(=O)O>[CH3:1][C@H:2]([NH:3][C:4](=[O:5])[O:6][C:7]([CH3:8])([CH3:9])[CH3:10])[c:11]1[n:12][c:13]2[c:14]([c:15]([Br:16])[c:17]([F:18])[cH:19][cH:20]2)[n:21]1[CH:22]1[CH2:23][CH2:24]1\"}",
"reactionStep": {
"id": "sa_61f06b8a366e418666fece9b",
"reactionHash": "570039baadc58c5ecf100a15be28caa9acc129796339fcc41390ef20d2e1e8ce"
},
"children": [
{
"id": "3716",
"routeId": "sa_61d0aa6dd8ab91c11af09f94",
"moleculeId": "sa_bb8e07ca0abc8e9ee7536b67",
"parentId": "3715",
"isLeaf": false,
"molecule": {
"id": "sa_bb8e07ca0abc8e9ee7536b67",
"inchikey": "YWCXPRNGRWTJQE-VIFPVBQESA-N",
"smiles": "C[C@H](NC(=O)OC(C)(C)C)C(=O)Nc1ccc(F)c(Br)c1NC1CC1"
},
"smiles": "C[C@H](NC(=O)OC(C)(C)C)C(=O)Nc1ccc(F)c(Br)c1NC1CC1",
"reactionStepId": "sa_3df8d997ff58072f7851883d",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20120202785A1;1139;1251494\",\"rsmi\":\"O[C:11]([C@H:2]([CH3:1])[NH:3][C:4](=[O:5])[O:6][C:7]([CH3:8])([CH3:9])[CH3:10])=[O:12].[NH2:13][c:14]1[c:15]([NH:16][CH:17]2[CH2:18][CH2:19]2)[c:20]([Br:21])[c:22]([F:23])[cH:24][cH:25]1>CCN=C=NCCCN(C)C.Cl.ClCCl.On1nnc2cccnc21>[CH3:1][C@H:2]([NH:3][C:4](=[O:5])[O:6][C:7]([CH3:8])([CH3:9])[CH3:10])[C:11](=[O:12])[NH:13][c:14]1[c:15]([NH:16][CH:17]2[CH2:18][CH2:19]2)[c:20]([Br:21])[c:22]([F:23])[cH:24][cH:25]1\"},\"mapped_reaction_smiles\":\"O[C:11]([C@H:2]([CH3:1])[NH:3][C:4](=[O:5])[O:6][C:7]([CH3:8])([CH3:9])[CH3:10])=[O:12].[NH2:13][c:14]1[c:15]([NH:16][CH:17]2[CH2:18][CH2:19]2)[c:20]([Br:21])[c:22]([F:23])[cH:24][cH:25]1>CCN=C=NCCCN(C)C.Cl.ClCCl.On1nnc2cccnc21>[CH3:1][C@H:2]([NH:3][C:4](=[O:5])[O:6][C:7]([CH3:8])([CH3:9])[CH3:10])[C:11](=[O:12])[NH:13][c:14]1[c:15]([NH:16][CH:17]2[CH2:18][CH2:19]2)[c:20]([Br:21])[c:22]([F:23])[cH:24][cH:25]1\"}",
"reactionStep": {
"id": "sa_3df8d997ff58072f7851883d",
"reactionHash": "03dc58a4d806d743aeca722dd233b26f6cf56d6930a95dec576b45ce259b8c1d"
},
"children": [
{
"id": "3717",
"routeId": "sa_61d0aa6dd8ab91c11af09f94",
"moleculeId": "sa_1099555443983c2e632722c8",
"parentId": "3716",
"isLeaf": true,
"molecule": {
"id": "sa_1099555443983c2e632722c8",
"inchikey": "QVHJQCGUWFKTSE-YFKPBYRVSA-N",
"smiles": "C[C@H](NC(=O)OC(C)(C)C)C(=O)O"
},
"smiles": "C[C@H](NC(=O)OC(C)(C)C)C(=O)O",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "3718",
"routeId": "sa_61d0aa6dd8ab91c11af09f94",
"moleculeId": "sa_af29939bca76c8aafd8d67f4",
"parentId": "3716",
"isLeaf": false,
"molecule": {
"id": "sa_af29939bca76c8aafd8d67f4",
"inchikey": "RMKQYBQSGURAHX-UHFFFAOYSA-N",
"smiles": "Nc1ccc(F)c(Br)c1NC1CC1"
},
"smiles": "Nc1ccc(F)c(Br)c1NC1CC1",
"reactionStepId": "sa_08a70c584c11c2c0f3fd2743",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20120202785A1;1137;1251493\",\"rsmi\":\"O=[N+:1]([O-])[c:2]1[cH:3][cH:4][c:5]([F:6])[c:7]([Br:8])[c:9]1F.[NH2:10][CH:11]1[CH2:12][CH2:13]1>CC#N.CCN(C(C)C)C(C)C.Cl.[Fe].N>[NH2:1][c:2]1[cH:3][cH:4][c:5]([F:6])[c:7]([Br:8])[c:9]1[NH:10][CH:11]1[CH2:12][CH2:13]1\"},\"mapped_reaction_smiles\":\"O=[N+:1]([O-])[c:2]1[cH:3][cH:4][c:5]([F:6])[c:7]([Br:8])[c:9]1F.[NH2:10][CH:11]1[CH2:12][CH2:13]1>CC#N.CCN(C(C)C)C(C)C.Cl.[Fe].N>[NH2:1][c:2]1[cH:3][cH:4][c:5]([F:6])[c:7]([Br:8])[c:9]1[NH:10][CH:11]1[CH2:12][CH2:13]1\"}",
"reactionStep": {
"id": "sa_08a70c584c11c2c0f3fd2743",
"reactionHash": "55ed30595013e2ab11b1ca75f36ccf509121c1aeb305cd5628eb4d94e2ebc476"
},
"children": [
{
"id": "3719",
"routeId": "sa_61d0aa6dd8ab91c11af09f94",
"moleculeId": "sa_f7b02628c6b00fb9d50a0f6c",
"parentId": "3718",
"isLeaf": true,
"molecule": {
"id": "sa_f7b02628c6b00fb9d50a0f6c",
"inchikey": "HTJDQJBWANPRPF-UHFFFAOYSA-N",
"smiles": "NC1CC1"
},
"smiles": "NC1CC1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "3720",
"routeId": "sa_61d0aa6dd8ab91c11af09f94",
"moleculeId": "sa_2911ecec273d477fba3ef9f7",
"parentId": "3718",
"isLeaf": true,
"molecule": {
"id": "sa_2911ecec273d477fba3ef9f7",
"inchikey": "IQCPYFIIMNLQNU-UHFFFAOYSA-N",
"smiles": "O=[N+]([O-])c1ccc(F)c(Br)c1F"
},
"smiles": "O=[N+]([O-])c1ccc(F)c(Br)c1F",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
]
}
]
},
{
"id": "3721",
"routeId": "sa_61d0aa6dd8ab91c11af09f94",
"moleculeId": "sa_77eead069993433ae88243bc",
"parentId": "3713",
"isLeaf": true,
"molecule": {
"id": "sa_77eead069993433ae88243bc",
"inchikey": "MAVMFCKRFRCMLE-UHFFFAOYSA-N",
"smiles": "N#Cc1c(Cl)nc[nH]c1=N"
},
"smiles": "N#Cc1c(N)ncnc1Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
}