Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
Nc1ccc(CN2CCOCC2)cn1
InChiKey
XQPFECSWBBZEOO-UHFFFAOYSA-N
Route Signature
c4f05023c30a25174ff44193582f8d2e0c4b2399cd6c1180053244426c7090d1
Synthesis route with 6 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_3d58ccf5788ed5f186c8d30d",
"signature": "c4f05023c30a25174ff44193582f8d2e0c4b2399cd6c1180053244426c7090d1",
"contentHash": "c7374056d7f2f337d592cc760db0b70a09a26f45b47c8b3c6f3b42222aa83e2f",
"length": 6,
"isConvergent": false
},
"target": {
"id": "sa_1fe0fd595fdc17615449e1a4",
"benchmarkSetId": "f925e688d731a0ad4e3aa6a505df094f6d3ca64ce3facc312bc5f64731921b33",
"targetId": "n5-00886",
"moleculeId": "sa_e229e91d4167bc487cde2dce",
"smiles": "Nc1ccc(CN2CCOCC2)cn1",
"routeLength": 6,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_e229e91d4167bc487cde2dce",
"inchikey": "XQPFECSWBBZEOO-UHFFFAOYSA-N",
"smiles": "Nc1ccc(CN2CCOCC2)cn1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 4
},
"rootNode": {
"id": "5053",
"routeId": "sa_3d58ccf5788ed5f186c8d30d",
"moleculeId": "sa_e229e91d4167bc487cde2dce",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_e229e91d4167bc487cde2dce",
"inchikey": "XQPFECSWBBZEOO-UHFFFAOYSA-N",
"smiles": "Nc1ccc(CN2CCOCC2)cn1"
},
"smiles": "Nc1ccc(CN2CCOCC2)cn1",
"reactionStepId": "sa_70350d7bae98a8e7ec3ab290",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150057272A1;0445;1657689\",\"rsmi\":\"CC(C)(C)OC(=O)[NH:1][c:2]1[n:3][cH:4][c:5]([CH2:6][N:7]2[CH2:8][CH2:9][O:10][CH2:11][CH2:12]2)[cH:13][cH:14]1>ClCCl.O=C(O)C(F)(F)F>[NH2:1][c:2]1[n:3][cH:4][c:5]([CH2:6][N:7]2[CH2:8][CH2:9][O:10][CH2:11][CH2:12]2)[cH:13][cH:14]1\"},\"mapped_reaction_smiles\":\"CC(C)(C)OC(=O)[NH:1][c:2]1[n:3][cH:4][c:5]([CH2:6][N:7]2[CH2:8][CH2:9][O:10][CH2:11][CH2:12]2)[cH:13][cH:14]1>ClCCl.O=C(O)C(F)(F)F>[NH2:1][c:2]1[n:3][cH:4][c:5]([CH2:6][N:7]2[CH2:8][CH2:9][O:10][CH2:11][CH2:12]2)[cH:13][cH:14]1\"}",
"reactionStep": {
"id": "sa_70350d7bae98a8e7ec3ab290",
"reactionHash": "900420feb033abdedc33c6385ae82031e8dcc05aa1fc9840286ab1dd5fdd7b5e"
},
"children": [
{
"id": "5054",
"routeId": "sa_3d58ccf5788ed5f186c8d30d",
"moleculeId": "sa_1f108d87209c0e33cf5729b9",
"parentId": "5053",
"isLeaf": false,
"molecule": {
"id": "sa_1f108d87209c0e33cf5729b9",
"inchikey": "YSNZBPHCKAZEJV-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)Nc1ccc(CN2CCOCC2)cn1"
},
"smiles": "CC(C)(C)OC(=O)Nc1ccc(CN2CCOCC2)cn1",
"reactionStepId": "sa_578c0929269bb87993a50251",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150057272A1;0443;1657688\",\"rsmi\":\"CS(=O)(=O)O[CH2:13][c:12]1[cH:11][n:10][c:9]([NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[cH:21][cH:20]1.[NH:14]1[CH2:15][CH2:16][O:17][CH2:18][CH2:19]1>CN(C)C=O.O.O=C(O)O.I.[K+].[K+].[Na+]>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][c:9]1[n:10][cH:11][c:12]([CH2:13][N:14]2[CH2:15][CH2:16][O:17][CH2:18][CH2:19]2)[cH:20][cH:21]1\"},\"mapped_reaction_smiles\":\"CS(=O)(=O)O[CH2:13][c:12]1[cH:11][n:10][c:9]([NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[cH:21][cH:20]1.[NH:14]1[CH2:15][CH2:16][O:17][CH2:18][CH2:19]1>CN(C)C=O.O.O=C(O)O.I.[K+].[K+].[Na+]>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][c:9]1[n:10][cH:11][c:12]([CH2:13][N:14]2[CH2:15][CH2:16][O:17][CH2:18][CH2:19]2)[cH:20][cH:21]1\"}",
"reactionStep": {
"id": "sa_578c0929269bb87993a50251",
"reactionHash": "3af6909dd43c031c5421e2742a4d1dd167aa89af6075a63e3dca70234fc5ae36"
},
"children": [
{
"id": "5055",
"routeId": "sa_3d58ccf5788ed5f186c8d30d",
"moleculeId": "sa_881c50a4eff0adf5358039c5",
"parentId": "5054",
"isLeaf": false,
"molecule": {
"id": "sa_881c50a4eff0adf5358039c5",
"inchikey": "MOCWQDAPJPLXCZ-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)Nc1ccc(COS(C)(=O)=O)cn1"
},
"smiles": "CC(C)(C)OC(=O)Nc1ccc(COS(C)(=O)=O)cn1",
"reactionStepId": "sa_61fdcccafe60fa5194c9721e",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150057272A1;0433;1657684\",\"rsmi\":\"Cl[S:15]([CH3:16])(=[O:17])=[O:18].[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][c:9]1[cH:10][cH:11][c:12]([CH2:13][OH:14])[cH:19][n:20]1>C1CCOC1.CCN(C(C)C)C(C)C>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][c:9]1[cH:10][cH:11][c:12]([CH2:13][O:14][S:15]([CH3:16])(=[O:17])=[O:18])[cH:19][n:20]1\"},\"mapped_reaction_smiles\":\"Cl[S:15]([CH3:16])(=[O:17])=[O:18].[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][c:9]1[cH:10][cH:11][c:12]([CH2:13][OH:14])[cH:19][n:20]1>C1CCOC1.CCN(C(C)C)C(C)C>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][c:9]1[cH:10][cH:11][c:12]([CH2:13][O:14][S:15]([CH3:16])(=[O:17])=[O:18])[cH:19][n:20]1\"}",
"reactionStep": {
"id": "sa_61fdcccafe60fa5194c9721e",
"reactionHash": "42a356ddfd8b1ddbac1e13a40da290e9f570c96f5396db19af42704d91a730f5"
},
"children": [
{
"id": "5056",
"routeId": "sa_3d58ccf5788ed5f186c8d30d",
"moleculeId": "sa_087abd88678650e758aa9f03",
"parentId": "5055",
"isLeaf": false,
"molecule": {
"id": "sa_087abd88678650e758aa9f03",
"inchikey": "BORDVYKLAFQRSP-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(O)=Nc1ccc(CO)cn1"
},
"smiles": "CC(C)(C)OC(=O)Nc1ccc(CO)cn1",
"reactionStepId": "sa_9e639873c959b6adaf899b9f",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150057272A1;0431;1657683\",\"rsmi\":\"CCO[C:13]([c:12]1[cH:11][n:10][c:9]([NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[cH:16][cH:15]1)=[O:14]>C1CCOC1.[Al+3].[HH].[HH].[HH].[HH].[Li+]>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][c:9]1[n:10][cH:11][c:12]([CH2:13][OH:14])[cH:15][cH:16]1\"},\"mapped_reaction_smiles\":\"CCO[C:13]([c:12]1[cH:11][n:10][c:9]([NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[cH:16][cH:15]1)=[O:14]>C1CCOC1.[Al+3].[HH].[HH].[HH].[HH].[Li+]>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][c:9]1[n:10][cH:11][c:12]([CH2:13][OH:14])[cH:15][cH:16]1\"}",
"reactionStep": {
"id": "sa_9e639873c959b6adaf899b9f",
"reactionHash": "6c32fcc1d25c26b3ca8f1e4de7144836f04ada738d2c151e6e4ef1433e580a82"
},
"children": [
{
"id": "5057",
"routeId": "sa_3d58ccf5788ed5f186c8d30d",
"moleculeId": "sa_09ef31ae233a3abd70dcbd81",
"parentId": "5056",
"isLeaf": false,
"molecule": {
"id": "sa_09ef31ae233a3abd70dcbd81",
"inchikey": "MCQWEDNIHBKKJY-UHFFFAOYSA-N",
"smiles": "CCOC(=O)c1ccc(NC(=O)OC(C)(C)C)nc1"
},
"smiles": "CCOC(=O)c1ccc(NC(=O)OC(C)(C)C)nc1",
"reactionStepId": "sa_e7743edba1a083c87366ed36",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150057272A1;0429;1657682\",\"rsmi\":\"CC(C)(C)OC(=O)O[C:11](=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17].[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][c:9]([NH2:10])[cH:18][cH:19]1>CC(C)(C)O.CC(C)=O.CN(C)c1ccncc1>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][c:9]([NH:10][C:11](=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17])[cH:18][cH:19]1\"},\"mapped_reaction_smiles\":\"CC(C)(C)OC(=O)O[C:11](=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17].[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][c:9]([NH2:10])[cH:18][cH:19]1>CC(C)(C)O.CC(C)=O.CN(C)c1ccncc1>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][c:9]([NH:10][C:11](=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17])[cH:18][cH:19]1\"}",
"reactionStep": {
"id": "sa_e7743edba1a083c87366ed36",
"reactionHash": "23ae30c2c1090fd5d7ea42af6c43f4af5499de3bc52091cb98ddc83df8e1c173"
},
"children": [
{
"id": "5058",
"routeId": "sa_3d58ccf5788ed5f186c8d30d",
"moleculeId": "sa_b273d4d4546165bca2b249b5",
"parentId": "5057",
"isLeaf": true,
"molecule": {
"id": "sa_b273d4d4546165bca2b249b5",
"inchikey": "DYHSDKLCOJIUFX-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)OC(=O)OC(C)(C)C"
},
"smiles": "CC(C)(C)OC(=O)OC(=O)OC(C)(C)C",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "5059",
"routeId": "sa_3d58ccf5788ed5f186c8d30d",
"moleculeId": "sa_1149ea80cdcbde3e889822ee",
"parentId": "5057",
"isLeaf": false,
"molecule": {
"id": "sa_1149ea80cdcbde3e889822ee",
"inchikey": "FIKVWPJKNMTBBD-UHFFFAOYSA-N",
"smiles": "CCOC(=O)c1ccc(=N)[nH]c1"
},
"smiles": "CCOC(=O)c1ccc(N)nc1",
"reactionStepId": "sa_0fc3b768b64c0ac822224bbb",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150057272A1;0427;1657681\",\"rsmi\":\"O[C:4](=[O:5])[c:6]1[cH:7][n:8][c:9]([NH2:10])[cH:11][cH:12]1.[CH3:1][CH2:2][OH:3]>O=S(Cl)Cl>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][c:9]([NH2:10])[cH:11][cH:12]1\"},\"mapped_reaction_smiles\":\"O[C:4](=[O:5])[c:6]1[cH:7][n:8][c:9]([NH2:10])[cH:11][cH:12]1.[CH3:1][CH2:2][OH:3]>O=S(Cl)Cl>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][c:9]([NH2:10])[cH:11][cH:12]1\"}",
"reactionStep": {
"id": "sa_0fc3b768b64c0ac822224bbb",
"reactionHash": "de2d9bfc034d4f68feb2c8fa23b61df59e88e504974b54fdfd016e9749b6f4e2"
},
"children": [
{
"id": "5060",
"routeId": "sa_3d58ccf5788ed5f186c8d30d",
"moleculeId": "sa_afaca116b303dc7d01346819",
"parentId": "5059",
"isLeaf": true,
"molecule": {
"id": "sa_afaca116b303dc7d01346819",
"inchikey": "LFQSCWFLJHTTHZ-UHFFFAOYSA-N",
"smiles": "CCO"
},
"smiles": "CCO",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "5061",
"routeId": "sa_3d58ccf5788ed5f186c8d30d",
"moleculeId": "sa_63e14676c81e58f120d095db",
"parentId": "5059",
"isLeaf": true,
"molecule": {
"id": "sa_63e14676c81e58f120d095db",
"inchikey": "ZCIFWRHIEBXBOY-UHFFFAOYSA-N",
"smiles": "Nc1ccc(C(=O)O)cn1"
},
"smiles": "Nc1ccc(C(=O)O)cn1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
]
},
{
"id": "5062",
"routeId": "sa_3d58ccf5788ed5f186c8d30d",
"moleculeId": "sa_d2a31ea58046b00856f61ca5",
"parentId": "5055",
"isLeaf": true,
"molecule": {
"id": "sa_d2a31ea58046b00856f61ca5",
"inchikey": "QARBMVPHQWIHKH-UHFFFAOYSA-N",
"smiles": "CS(=O)(=O)Cl"
},
"smiles": "CS(=O)(=O)Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "5063",
"routeId": "sa_3d58ccf5788ed5f186c8d30d",
"moleculeId": "sa_39d71c291f7fdf13918cc969",
"parentId": "5054",
"isLeaf": true,
"molecule": {
"id": "sa_39d71c291f7fdf13918cc969",
"inchikey": "YNAVUWVOSKDBBP-UHFFFAOYSA-N",
"smiles": "C1COCCN1"
},
"smiles": "C1COCCN1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
}