Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CCn1nc(-c2cnccn2)cc1-c1cnc2[nH]c(C3CCCCC3)cc2c1
InChiKey
VTZLYIOPFJKRIR-UHFFFAOYSA-N
Route Signature
92123394f150000d38e4569c68e45ba39090b1fb5e537a58c68e115dc7d3c58e
Synthesis route with 4 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_1eb19504a697a2cba92baab7",
"signature": "92123394f150000d38e4569c68e45ba39090b1fb5e537a58c68e115dc7d3c58e",
"contentHash": "03c97efd75029a937f953bf841b46e9849da536dff19cfcf2f276b66d589844a",
"length": 4,
"isConvergent": true
},
"target": {
"id": "sa_c8e91e7643b9aa847d51d16f",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-02123",
"moleculeId": "sa_f78f07abd5fc2388628bb055",
"smiles": "CCn1nc(-c2cnccn2)cc1-c1cnc2[nH]c(C3CCCCC3)cc2c1",
"routeLength": 4,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_f78f07abd5fc2388628bb055",
"inchikey": "VTZLYIOPFJKRIR-UHFFFAOYSA-N",
"smiles": "CCn1nc(-c2cnccn2)cc1-c1cnc2[nH]c(C3CCCCC3)cc2c1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "10619",
"routeId": "sa_1eb19504a697a2cba92baab7",
"moleculeId": "sa_f78f07abd5fc2388628bb055",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_f78f07abd5fc2388628bb055",
"inchikey": "VTZLYIOPFJKRIR-UHFFFAOYSA-N",
"smiles": "CCn1nc(-c2cnccn2)cc1-c1cnc2[nH]c(C3CCCCC3)cc2c1"
},
"smiles": "CCn1nc(-c2cnccn2)cc1-c1cnc2[nH]c(C3CCCCC3)cc2c1",
"reactionStepId": "sa_68516abee8eeb0d013f80955",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130158049A1;0274;1383409\",\"rsmi\":\"CC1(C)OB([c:14]2[cH:15][n:16][c:17]3[nH:18][c:19]([CH:20]4[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]4)[cH:26][c:27]3[cH:28]2)OC1(C)C.O=S(=O)(O[c:13]1[n:3]([CH2:2][CH3:1])[n:4][c:5](-[c:6]2[n:7][cH:8][cH:9][n:10][cH:11]2)[cH:12]1)C(F)(F)F>>[CH3:1][CH2:2][n:3]1[n:4][c:5](-[c:6]2[n:7][cH:8][cH:9][n:10][cH:11]2)[cH:12][c:13]1-[c:14]1[cH:15][n:16][c:17]2[nH:18][c:19]([CH:20]3[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]3)[cH:26][c:27]2[cH:28]1\"},\"mapped_reaction_smiles\":\"CC1(C)OB([c:14]2[cH:15][n:16][c:17]3[nH:18][c:19]([CH:20]4[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]4)[cH:26][c:27]3[cH:28]2)OC1(C)C.O=S(=O)(O[c:13]1[n:3]([CH2:2][CH3:1])[n:4][c:5](-[c:6]2[n:7][cH:8][cH:9][n:10][cH:11]2)[cH:12]1)C(F)(F)F>>[CH3:1][CH2:2][n:3]1[n:4][c:5](-[c:6]2[n:7][cH:8][cH:9][n:10][cH:11]2)[cH:12][c:13]1-[c:14]1[cH:15][n:16][c:17]2[nH:18][c:19]([CH:20]3[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]3)[cH:26][c:27]2[cH:28]1\"}",
"reactionStep": {
"id": "sa_68516abee8eeb0d013f80955",
"reactionHash": "8bd3579480921ea87cf14f4590bcc12d728a49d2b197810c6fff1924c8b28ae9"
},
"children": [
{
"id": "10620",
"routeId": "sa_1eb19504a697a2cba92baab7",
"moleculeId": "sa_946c3d0f0ae73a6bfdb7846c",
"parentId": "10619",
"isLeaf": false,
"molecule": {
"id": "sa_946c3d0f0ae73a6bfdb7846c",
"inchikey": "AGZWYAXZRDHVJP-UHFFFAOYSA-N",
"smiles": "CC1(C)OB(c2cnc3[nH]c(C4CCCCC4)cc3c2)OC1(C)C"
},
"smiles": "CC1(C)OB(c2cnc3[nH]c(C4CCCCC4)cc3c2)OC1(C)C",
"reactionStepId": "sa_f79a8931f5bc9b22cecbf864",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130158049A1;0269;1383406\",\"rsmi\":\"Br[c:6]1[cH:7][n:8][c:9]2[nH:10][c:11]([CH:12]3[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]3)[cH:18][c:19]2[cH:20]1.CC1(C)OB([B:5]2[O:4][C:2]([CH3:1])([CH3:3])[C:22]([CH3:23])([CH3:24])[O:21]2)OC1(C)C>C1COCCO1.CC(=O)O.[K+]>[CH3:1][C:2]1([CH3:3])[O:4][B:5]([c:6]2[cH:7][n:8][c:9]3[nH:10][c:11]([CH:12]4[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]4)[cH:18][c:19]3[cH:20]2)[O:21][C:22]1([CH3:23])[CH3:24]\"},\"mapped_reaction_smiles\":\"Br[c:6]1[cH:7][n:8][c:9]2[nH:10][c:11]([CH:12]3[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]3)[cH:18][c:19]2[cH:20]1.CC1(C)OB([B:5]2[O:4][C:2]([CH3:1])([CH3:3])[C:22]([CH3:23])([CH3:24])[O:21]2)OC1(C)C>C1COCCO1.CC(=O)O.[K+]>[CH3:1][C:2]1([CH3:3])[O:4][B:5]([c:6]2[cH:7][n:8][c:9]3[nH:10][c:11]([CH:12]4[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]4)[cH:18][c:19]3[cH:20]2)[O:21][C:22]1([CH3:23])[CH3:24]\"}",
"reactionStep": {
"id": "sa_f79a8931f5bc9b22cecbf864",
"reactionHash": "9fe17dc3ef729fbb9de5898226ab073334d080ecfbb5088da315faa45a6612d5"
},
"children": [
{
"id": "10621",
"routeId": "sa_1eb19504a697a2cba92baab7",
"moleculeId": "sa_be463b142ac264206a0bb8f3",
"parentId": "10620",
"isLeaf": false,
"molecule": {
"id": "sa_be463b142ac264206a0bb8f3",
"inchikey": "IMBNEXKAHGZZFC-UHFFFAOYSA-N",
"smiles": "Brc1cnc2[nH]c(C3CCCCC3)cc2c1"
},
"smiles": "Brc1cnc2[nH]c(C3CCCCC3)cc2c1",
"reactionStepId": "sa_5dad77b2647214d3a9cf944f",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130158049A1;0268;1383405\",\"rsmi\":\"[Br:1][c:2]1[cH:3][n:4][c:5]([NH2:6])[c:15]([C:14]#[C:7][CH:8]2[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]2)[cH:16]1>CC(C)(C)O.CN1CCCC1=O.Cl.[K+].N>[Br:1][c:2]1[cH:3][n:4][c:5]2[nH:6][c:7]([CH:8]3[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]3)[cH:14][c:15]2[cH:16]1\"},\"mapped_reaction_smiles\":\"[Br:1][c:2]1[cH:3][n:4][c:5]([NH2:6])[c:15]([C:14]#[C:7][CH:8]2[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]2)[cH:16]1>CC(C)(C)O.CN1CCCC1=O.Cl.[K+].N>[Br:1][c:2]1[cH:3][n:4][c:5]2[nH:6][c:7]([CH:8]3[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]3)[cH:14][c:15]2[cH:16]1\"}",
"reactionStep": {
"id": "sa_5dad77b2647214d3a9cf944f",
"reactionHash": "de40c017f00ce140a4f2e20eae1a660be0a3c116fe984842aaa6a02326e3cc27"
},
"children": [
{
"id": "10622",
"routeId": "sa_1eb19504a697a2cba92baab7",
"moleculeId": "sa_9b3fc68ff9ff3387757bcf69",
"parentId": "10621",
"isLeaf": false,
"molecule": {
"id": "sa_9b3fc68ff9ff3387757bcf69",
"inchikey": "ZKEQAAAGOIHNOQ-UHFFFAOYSA-N",
"smiles": "Nc1ncc(Br)cc1C#CC1CCCCC1"
},
"smiles": "Nc1ncc(Br)cc1C#CC1CCCCC1",
"reactionStepId": "sa_68e095da6b67ffff91b1ebe8",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130158049A1;0267;1383404\",\"rsmi\":\"I[c:8]1[c:2]([NH2:1])[n:3][cH:4][c:5]([Br:6])[cH:7]1.[CH:9]#[C:10][CH:11]1[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]1>C1CCOC1.I[Cu]I.c1ccc([PH](c2ccccc2)(c2ccccc2)[Pd]([PH](c2ccccc2)(c2ccccc2)c2ccccc2)([PH](c2ccccc2)(c2ccccc2)c2ccccc2)[PH](c2ccccc2)(c2ccccc2)c2ccccc2)cc1>[NH2:1][c:2]1[n:3][cH:4][c:5]([Br:6])[cH:7][c:8]1[C:9]#[C:10][CH:11]1[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]1\"},\"mapped_reaction_smiles\":\"I[c:8]1[c:2]([NH2:1])[n:3][cH:4][c:5]([Br:6])[cH:7]1.[CH:9]#[C:10][CH:11]1[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]1>C1CCOC1.I[Cu]I.c1ccc([PH](c2ccccc2)(c2ccccc2)[Pd]([PH](c2ccccc2)(c2ccccc2)c2ccccc2)([PH](c2ccccc2)(c2ccccc2)c2ccccc2)[PH](c2ccccc2)(c2ccccc2)c2ccccc2)cc1>[NH2:1][c:2]1[n:3][cH:4][c:5]([Br:6])[cH:7][c:8]1[C:9]#[C:10][CH:11]1[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]1\"}",
"reactionStep": {
"id": "sa_68e095da6b67ffff91b1ebe8",
"reactionHash": "367854c040f2c5b3bd5b8a7793cbb7ca8f7f17ea3f00a68e803bbc52d997a743"
},
"children": [
{
"id": "10623",
"routeId": "sa_1eb19504a697a2cba92baab7",
"moleculeId": "sa_0164270b3014af74caeccb5b",
"parentId": "10622",
"isLeaf": true,
"molecule": {
"id": "sa_0164270b3014af74caeccb5b",
"inchikey": "SSDZYLQUYMOSAK-UHFFFAOYSA-N",
"smiles": "C#CC1CCCCC1"
},
"smiles": "C#CC1CCCCC1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "10624",
"routeId": "sa_1eb19504a697a2cba92baab7",
"moleculeId": "sa_9e6369b69104da7a237dd159",
"parentId": "10622",
"isLeaf": true,
"molecule": {
"id": "sa_9e6369b69104da7a237dd159",
"inchikey": "XPERZSKJGNUSHI-UHFFFAOYSA-N",
"smiles": "Nc1ncc(Br)cc1I"
},
"smiles": "Nc1ncc(Br)cc1I",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
},
{
"id": "10625",
"routeId": "sa_1eb19504a697a2cba92baab7",
"moleculeId": "sa_e6c301388ac142801d4af5a2",
"parentId": "10620",
"isLeaf": true,
"molecule": {
"id": "sa_e6c301388ac142801d4af5a2",
"inchikey": "IPWKHHSGDUIRAH-UHFFFAOYSA-N",
"smiles": "CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C"
},
"smiles": "CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "10626",
"routeId": "sa_1eb19504a697a2cba92baab7",
"moleculeId": "sa_755d4c7a0ee3ac36e82de3ed",
"parentId": "10619",
"isLeaf": false,
"molecule": {
"id": "sa_755d4c7a0ee3ac36e82de3ed",
"inchikey": "NNGCGGMZCQOMDC-UHFFFAOYSA-N",
"smiles": "CCn1nc(-c2cnccn2)cc1OS(=O)(=O)C(F)(F)F"
},
"smiles": "CCn1nc(-c2cnccn2)cc1OS(=O)(=O)C(F)(F)F",
"reactionStepId": "sa_097364cf1869d82a02fe90bc",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130158049A1;0176;1383355\",\"rsmi\":\"O=S(=O)(N(c1ccccc1)[S:15](=[O:16])(=[O:17])[C:18]([F:19])([F:20])[F:21])C(F)(F)F.[CH3:1][CH2:2][n:3]1[n:4][c:5](-[c:6]2[n:7][cH:8][cH:9][n:10][cH:11]2)[cH:12][c:13]1[OH:14]>CN(C)C=O.[HH].[Na+]>[CH3:1][CH2:2][n:3]1[n:4][c:5](-[c:6]2[n:7][cH:8][cH:9][n:10][cH:11]2)[cH:12][c:13]1[O:14][S:15](=[O:16])(=[O:17])[C:18]([F:19])([F:20])[F:21]\"},\"mapped_reaction_smiles\":\"O=S(=O)(N(c1ccccc1)[S:15](=[O:16])(=[O:17])[C:18]([F:19])([F:20])[F:21])C(F)(F)F.[CH3:1][CH2:2][n:3]1[n:4][c:5](-[c:6]2[n:7][cH:8][cH:9][n:10][cH:11]2)[cH:12][c:13]1[OH:14]>CN(C)C=O.[HH].[Na+]>[CH3:1][CH2:2][n:3]1[n:4][c:5](-[c:6]2[n:7][cH:8][cH:9][n:10][cH:11]2)[cH:12][c:13]1[O:14][S:15](=[O:16])(=[O:17])[C:18]([F:19])([F:20])[F:21]\"}",
"reactionStep": {
"id": "sa_097364cf1869d82a02fe90bc",
"reactionHash": "0514ac399fb47cca781b878c4eb7dbad13a618be019aaff86149b15bebd8853e"
},
"children": [
{
"id": "10627",
"routeId": "sa_1eb19504a697a2cba92baab7",
"moleculeId": "sa_24bc5b50442cd9e5fcf68f54",
"parentId": "10626",
"isLeaf": true,
"molecule": {
"id": "sa_24bc5b50442cd9e5fcf68f54",
"inchikey": "DIOHEXPTUTVCNX-UHFFFAOYSA-N",
"smiles": "O=S(=O)(N(c1ccccc1)S(=O)(=O)C(F)(F)F)C(F)(F)F"
},
"smiles": "O=S(=O)(N(c1ccccc1)S(=O)(=O)C(F)(F)F)C(F)(F)F",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "10628",
"routeId": "sa_1eb19504a697a2cba92baab7",
"moleculeId": "sa_7f1a52cb4b9227a266979d3a",
"parentId": "10626",
"isLeaf": true,
"molecule": {
"id": "sa_7f1a52cb4b9227a266979d3a",
"inchikey": "VFMDHVQHSBQJMV-UHFFFAOYSA-N",
"smiles": "CCn1nc(-c2cnccn2)cc1O"
},
"smiles": "CCn1nc(-c2cnccn2)cc1O",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
}