Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
COc1cc(-c2cc(CN(c3ccc(SC)cc3)C3CCN(C(=O)OC(C)(C)C)CC3)ccn2)cc(OC)c1OC
InChiKey
QYXHGGPXWQEEQF-UHFFFAOYSA-N
Route Signature
f7bf1a76e90f5a3d7660234ec74b5e2030aeb07a1ed8a23fbc91423bd7f0fcc1
Synthesis route with 4 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_596e3e64fa09c3b16afacf94",
"signature": "f7bf1a76e90f5a3d7660234ec74b5e2030aeb07a1ed8a23fbc91423bd7f0fcc1",
"contentHash": "7827fe7016fa02c8c23b564ffb718c8b354e18a7d8e7fe8b7af37719b6dc6103",
"length": 4,
"isConvergent": true
},
"target": {
"id": "sa_0348d5ae85874e89ddf29d8b",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-01336",
"moleculeId": "sa_5e32ddc13828873b5ec02864",
"smiles": "COc1cc(-c2cc(CN(c3ccc(SC)cc3)C3CCN(C(=O)OC(C)(C)C)CC3)ccn2)cc(OC)c1OC",
"routeLength": 4,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_5e32ddc13828873b5ec02864",
"inchikey": "QYXHGGPXWQEEQF-UHFFFAOYSA-N",
"smiles": "COc1cc(-c2cc(CN(c3ccc(SC)cc3)C3CCN(C(=O)OC(C)(C)C)CC3)ccn2)cc(OC)c1OC"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "10099",
"routeId": "sa_596e3e64fa09c3b16afacf94",
"moleculeId": "sa_5e32ddc13828873b5ec02864",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_5e32ddc13828873b5ec02864",
"inchikey": "QYXHGGPXWQEEQF-UHFFFAOYSA-N",
"smiles": "COc1cc(-c2cc(CN(c3ccc(SC)cc3)C3CCN(C(=O)OC(C)(C)C)CC3)ccn2)cc(OC)c1OC"
},
"smiles": "COc1cc(-c2cc(CN(c3ccc(SC)cc3)C3CCN(C(=O)OC(C)(C)C)CC3)ccn2)cc(OC)c1OC",
"reactionStepId": "sa_4cc0f80550d031fd3525d422",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20050176764A1;0848;274061\",\"rsmi\":\"Cl[CH2:11][c:10]1[cH:9][cH:8][n:7][c:6](-[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:39]([O:40][CH3:41])[c:36]([O:37][CH3:38])[cH:35]2)[cH:34]1.[NH:12]([c:13]1[cH:14][cH:15][c:16]([S:17][CH3:18])[cH:19][cH:20]1)[CH:21]1[CH2:22][CH2:23][N:24]([C:25](=[O:26])[O:27][C:28]([CH3:29])([CH3:30])[CH3:31])[CH2:32][CH2:33]1>>[CH3:1][O:2][c:3]1[cH:4][c:5](-[c:6]2[n:7][cH:8][cH:9][c:10]([CH2:11][N:12]([c:13]3[cH:14][cH:15][c:16]([S:17][CH3:18])[cH:19][cH:20]3)[CH:21]3[CH2:22][CH2:23][N:24]([C:25](=[O:26])[O:27][C:28]([CH3:29])([CH3:30])[CH3:31])[CH2:32][CH2:33]3)[cH:34]2)[cH:35][c:36]([O:37][CH3:38])[c:39]1[O:40][CH3:41]\"},\"mapped_reaction_smiles\":\"Cl[CH2:11][c:10]1[cH:9][cH:8][n:7][c:6](-[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:39]([O:40][CH3:41])[c:36]([O:37][CH3:38])[cH:35]2)[cH:34]1.[NH:12]([c:13]1[cH:14][cH:15][c:16]([S:17][CH3:18])[cH:19][cH:20]1)[CH:21]1[CH2:22][CH2:23][N:24]([C:25](=[O:26])[O:27][C:28]([CH3:29])([CH3:30])[CH3:31])[CH2:32][CH2:33]1>>[CH3:1][O:2][c:3]1[cH:4][c:5](-[c:6]2[n:7][cH:8][cH:9][c:10]([CH2:11][N:12]([c:13]3[cH:14][cH:15][c:16]([S:17][CH3:18])[cH:19][cH:20]3)[CH:21]3[CH2:22][CH2:23][N:24]([C:25](=[O:26])[O:27][C:28]([CH3:29])([CH3:30])[CH3:31])[CH2:32][CH2:33]3)[cH:34]2)[cH:35][c:36]([O:37][CH3:38])[c:39]1[O:40][CH3:41]\"}",
"reactionStep": {
"id": "sa_4cc0f80550d031fd3525d422",
"reactionHash": "b041a52ab1945d650de33110a9e1f51af3b38b8cc3830c7358eebdf329a130b7"
},
"children": [
{
"id": "10100",
"routeId": "sa_596e3e64fa09c3b16afacf94",
"moleculeId": "sa_9fa34944329d918e6e6a7a6a",
"parentId": "10099",
"isLeaf": false,
"molecule": {
"id": "sa_9fa34944329d918e6e6a7a6a",
"inchikey": "AJJXCPOSNVIOND-UHFFFAOYSA-N",
"smiles": "CSc1ccc(NC2CCN(C(=O)OC(C)(C)C)CC2)cc1"
},
"smiles": "CSc1ccc(NC2CCN(C(=O)OC(C)(C)C)CC2)cc1",
"reactionStepId": "sa_dd729ca4dba41001e716bbb3",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20050176764A1;0844;274060\",\"rsmi\":\"O=[C:8]1[CH2:9][CH2:10][N:11]([C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[CH2:19][CH2:20]1.[CH3:1][S:2][c:3]1[cH:4][cH:5][c:6]([NH2:7])[cH:21][cH:22]1>>[CH3:1][S:2][c:3]1[cH:4][cH:5][c:6]([NH:7][CH:8]2[CH2:9][CH2:10][N:11]([C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[CH2:19][CH2:20]2)[cH:21][cH:22]1\"},\"mapped_reaction_smiles\":\"O=[C:8]1[CH2:9][CH2:10][N:11]([C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[CH2:19][CH2:20]1.[CH3:1][S:2][c:3]1[cH:4][cH:5][c:6]([NH2:7])[cH:21][cH:22]1>>[CH3:1][S:2][c:3]1[cH:4][cH:5][c:6]([NH:7][CH:8]2[CH2:9][CH2:10][N:11]([C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[CH2:19][CH2:20]2)[cH:21][cH:22]1\"}",
"reactionStep": {
"id": "sa_dd729ca4dba41001e716bbb3",
"reactionHash": "632e1f8aaf2a62745c6a00334feba0cf0fdd9fb77b8a47b06d5843907de119d1"
},
"children": [
{
"id": "10101",
"routeId": "sa_596e3e64fa09c3b16afacf94",
"moleculeId": "sa_806e424090667321a5b9727c",
"parentId": "10100",
"isLeaf": true,
"molecule": {
"id": "sa_806e424090667321a5b9727c",
"inchikey": "ROUYFJUVMYHXFJ-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)N1CCC(=O)CC1"
},
"smiles": "CC(C)(C)OC(=O)N1CCC(=O)CC1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "10102",
"routeId": "sa_596e3e64fa09c3b16afacf94",
"moleculeId": "sa_fa43244c39854048344d07dd",
"parentId": "10100",
"isLeaf": true,
"molecule": {
"id": "sa_fa43244c39854048344d07dd",
"inchikey": "YKFROQCFVXOUPW-UHFFFAOYSA-N",
"smiles": "CSc1ccc(N)cc1"
},
"smiles": "CSc1ccc(N)cc1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "10103",
"routeId": "sa_596e3e64fa09c3b16afacf94",
"moleculeId": "sa_ee91ade76ae15dd4923ee8f6",
"parentId": "10099",
"isLeaf": false,
"molecule": {
"id": "sa_ee91ade76ae15dd4923ee8f6",
"inchikey": "SBGHNDCBGPREJJ-UHFFFAOYSA-N",
"smiles": "COc1cc(-c2cc(CCl)ccn2)cc(OC)c1OC"
},
"smiles": "COc1cc(-c2cc(CCl)ccn2)cc(OC)c1OC",
"reactionStepId": "sa_7439df8110c643de82258022",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20050176764A1;0080;273950\",\"rsmi\":\"ClC(Cl)[Cl:12].O[CH2:11][c:10]1[cH:9][cH:8][n:7][c:6](-[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:18]([O:19][CH3:20])[c:15]([O:16][CH3:17])[cH:14]2)[cH:13]1>Cl>[CH3:1][O:2][c:3]1[cH:4][c:5](-[c:6]2[n:7][cH:8][cH:9][c:10]([CH2:11][Cl:12])[cH:13]2)[cH:14][c:15]([O:16][CH3:17])[c:18]1[O:19][CH3:20]\"},\"mapped_reaction_smiles\":\"ClC(Cl)[Cl:12].O[CH2:11][c:10]1[cH:9][cH:8][n:7][c:6](-[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:18]([O:19][CH3:20])[c:15]([O:16][CH3:17])[cH:14]2)[cH:13]1>Cl>[CH3:1][O:2][c:3]1[cH:4][c:5](-[c:6]2[n:7][cH:8][cH:9][c:10]([CH2:11][Cl:12])[cH:13]2)[cH:14][c:15]([O:16][CH3:17])[c:18]1[O:19][CH3:20]\"}",
"reactionStep": {
"id": "sa_7439df8110c643de82258022",
"reactionHash": "9e9135b33d3dbfdd56afcc24507df5af193e8ffb61ca61849371dcdbdb21bbae"
},
"children": [
{
"id": "10104",
"routeId": "sa_596e3e64fa09c3b16afacf94",
"moleculeId": "sa_dc22e7a2b152e64af529fbf5",
"parentId": "10103",
"isLeaf": true,
"molecule": {
"id": "sa_dc22e7a2b152e64af529fbf5",
"inchikey": "HEDRZPFGACZZDS-UHFFFAOYSA-N",
"smiles": "ClC(Cl)Cl"
},
"smiles": "ClC(Cl)Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "10105",
"routeId": "sa_596e3e64fa09c3b16afacf94",
"moleculeId": "sa_4678c764fd14ebf705dfb75f",
"parentId": "10103",
"isLeaf": false,
"molecule": {
"id": "sa_4678c764fd14ebf705dfb75f",
"inchikey": "HXWUFXFGYHUGEF-UHFFFAOYSA-N",
"smiles": "COc1cc(-c2cc(CO)ccn2)cc(OC)c1OC"
},
"smiles": "COc1cc(-c2cc(CO)ccn2)cc(OC)c1OC",
"reactionStepId": "sa_24c1a47a987ad28b6ccff4d2",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20050176764A1;0076;273949\",\"rsmi\":\"CCO[C:11]([c:10]1[cH:9][cH:8][n:7][c:6](-[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:18]([O:19][CH3:20])[c:15]([O:16][CH3:17])[cH:14]2)[cH:13]1)=[O:12]>C1CCOC1.O.O=S(=O)(O)O.[Al+3].[HH].[HH].[HH].[HH].[Li+].[Na+].[Na+]>[CH3:1][O:2][c:3]1[cH:4][c:5](-[c:6]2[n:7][cH:8][cH:9][c:10]([CH2:11][OH:12])[cH:13]2)[cH:14][c:15]([O:16][CH3:17])[c:18]1[O:19][CH3:20]\"},\"mapped_reaction_smiles\":\"CCO[C:11]([c:10]1[cH:9][cH:8][n:7][c:6](-[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:18]([O:19][CH3:20])[c:15]([O:16][CH3:17])[cH:14]2)[cH:13]1)=[O:12]>C1CCOC1.O.O=S(=O)(O)O.[Al+3].[HH].[HH].[HH].[HH].[Li+].[Na+].[Na+]>[CH3:1][O:2][c:3]1[cH:4][c:5](-[c:6]2[n:7][cH:8][cH:9][c:10]([CH2:11][OH:12])[cH:13]2)[cH:14][c:15]([O:16][CH3:17])[c:18]1[O:19][CH3:20]\"}",
"reactionStep": {
"id": "sa_24c1a47a987ad28b6ccff4d2",
"reactionHash": "317117d3c15989366141a89ac12cbfa4bed3bbb99dbfc14a17f87f6fdad5a7e8"
},
"children": [
{
"id": "10106",
"routeId": "sa_596e3e64fa09c3b16afacf94",
"moleculeId": "sa_14aaeaedec642c9e40397572",
"parentId": "10105",
"isLeaf": false,
"molecule": {
"id": "sa_14aaeaedec642c9e40397572",
"inchikey": "VZFJQRIDOLQYLN-UHFFFAOYSA-N",
"smiles": "CCOC(=O)c1ccnc(-c2cc(OC)c(OC)c(OC)c2)c1"
},
"smiles": "CCOC(=O)c1ccnc(-c2cc(OC)c(OC)c(OC)c2)c1",
"reactionStepId": "sa_90504784fd988e830044ab3c",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20050176764A1;0072;273948\",\"rsmi\":\"Cl[c:8]1[cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:23][cH:22][n:21]1.OB(O)[c:9]1[cH:10][c:11]([O:12][CH3:13])[c:14]([O:15][CH3:16])[c:17]([O:18][CH3:19])[cH:20]1>C1CCOC1.CCOC(C)=O.Cc1ccccc1.O=C(O)O.[Na+].[Na+].[Pd].c1ccc(P(c2ccccc2)c2ccccc2)cc1.c1ccc(P(c2ccccc2)c2ccccc2)cc1.c1ccc(P(c2ccccc2)c2ccccc2)cc1.c1ccc(P(c2ccccc2)c2ccccc2)cc1>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8](-[c:9]2[cH:10][c:11]([O:12][CH3:13])[c:14]([O:15][CH3:16])[c:17]([O:18][CH3:19])[cH:20]2)[n:21][cH:22][cH:23]1\"},\"mapped_reaction_smiles\":\"Cl[c:8]1[cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:23][cH:22][n:21]1.OB(O)[c:9]1[cH:10][c:11]([O:12][CH3:13])[c:14]([O:15][CH3:16])[c:17]([O:18][CH3:19])[cH:20]1>C1CCOC1.CCOC(C)=O.Cc1ccccc1.O=C(O)O.[Na+].[Na+].[Pd].c1ccc(P(c2ccccc2)c2ccccc2)cc1.c1ccc(P(c2ccccc2)c2ccccc2)cc1.c1ccc(P(c2ccccc2)c2ccccc2)cc1.c1ccc(P(c2ccccc2)c2ccccc2)cc1>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8](-[c:9]2[cH:10][c:11]([O:12][CH3:13])[c:14]([O:15][CH3:16])[c:17]([O:18][CH3:19])[cH:20]2)[n:21][cH:22][cH:23]1\"}",
"reactionStep": {
"id": "sa_90504784fd988e830044ab3c",
"reactionHash": "2a823169e311df84f230df607f1fe84edb414be1a0f634551baab7285bf7dc2c"
},
"children": [
{
"id": "10107",
"routeId": "sa_596e3e64fa09c3b16afacf94",
"moleculeId": "sa_42fc6070ded047aa603f39d7",
"parentId": "10106",
"isLeaf": true,
"molecule": {
"id": "sa_42fc6070ded047aa603f39d7",
"inchikey": "IGRLNCOFYMWKBU-UHFFFAOYSA-N",
"smiles": "CCOC(=O)c1ccnc(Cl)c1"
},
"smiles": "CCOC(=O)c1ccnc(Cl)c1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "10108",
"routeId": "sa_596e3e64fa09c3b16afacf94",
"moleculeId": "sa_fb001084e89e8bd6c45fe5c1",
"parentId": "10106",
"isLeaf": true,
"molecule": {
"id": "sa_fb001084e89e8bd6c45fe5c1",
"inchikey": "RULQUTYJXDLRFL-UHFFFAOYSA-N",
"smiles": "COc1cc(B(O)O)cc(OC)c1OC"
},
"smiles": "COc1cc(B(O)O)cc(OC)c1OC",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
]
}
]
}
}