Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
N#Cc1c(-c2ccc(Oc3ccccc3)cc2)nn(C2CC3CC2CN3C(=O)OCc2ccccc2)c1N
InChiKey
DKTXBDIBFZFUQE-UHFFFAOYSA-N
Route Signature
f1630ca89887a90b8baac2f84cc9057999e263f9c7e66f3495cd3636406bbc29
Synthesis route with 4 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_560419207ca574f4292cc5b7",
"signature": "f1630ca89887a90b8baac2f84cc9057999e263f9c7e66f3495cd3636406bbc29",
"contentHash": "a57f87a5a628cb6f5cac58b8cd0e0fcf4d8c1fcdd21573cceb10c74236eb9219",
"length": 4,
"isConvergent": false
},
"target": {
"id": "sa_a934165e57429dbcc34c2968",
"benchmarkSetId": "f925e688d731a0ad4e3aa6a505df094f6d3ca64ce3facc312bc5f64731921b33",
"targetId": "n5-07610",
"moleculeId": "sa_5f9423527859e49d5de89971",
"smiles": "N#Cc1c(-c2ccc(Oc3ccccc3)cc2)nn(C2CC3CC2CN3C(=O)OCc2ccccc2)c1N",
"routeLength": 4,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_5f9423527859e49d5de89971",
"inchikey": "DKTXBDIBFZFUQE-UHFFFAOYSA-N",
"smiles": "N#Cc1c(-c2ccc(Oc3ccccc3)cc2)nn(C2CC3CC2CN3C(=O)OCc2ccccc2)c1N"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 2
},
"rootNode": {
"id": "8389",
"routeId": "sa_560419207ca574f4292cc5b7",
"moleculeId": "sa_5f9423527859e49d5de89971",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_5f9423527859e49d5de89971",
"inchikey": "DKTXBDIBFZFUQE-UHFFFAOYSA-N",
"smiles": "N#Cc1c(-c2ccc(Oc3ccccc3)cc2)nn(C2CC3CC2CN3C(=O)OCc2ccccc2)c1N"
},
"smiles": "N#Cc1c(-c2ccc(Oc3ccccc3)cc2)nn(C2CC3CC2CN3C(=O)OCc2ccccc2)c1N",
"reactionStepId": "sa_1d76f6b29194031f1952937c",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150291554A1;0300;1767551\",\"rsmi\":\"CO[C:25](=[C:3]([C:2]#[N:1])[C:4]#[N:5])[c:26]1[cH:27][cH:28][c:29]([O:30][c:31]2[cH:32][cH:33][cH:34][cH:35][cH:36]2)[cH:37][cH:38]1.[NH:6]([CH:7]1[CH2:8][CH:9]2[CH2:10][CH:11]1[CH2:12][N:13]2[C:14](=[O:15])[O:16][CH2:17][c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1)[NH2:24]>CCN(CC)CC.CCO>[N:1]#[C:2][c:3]1[c:4]([NH2:5])[n:6]([CH:7]2[CH2:8][CH:9]3[CH2:10][CH:11]2[CH2:12][N:13]3[C:14](=[O:15])[O:16][CH2:17][c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)[n:24][c:25]1-[c:26]1[cH:27][cH:28][c:29]([O:30][c:31]2[cH:32][cH:33][cH:34][cH:35][cH:36]2)[cH:37][cH:38]1\"},\"mapped_reaction_smiles\":\"CO[C:25](=[C:3]([C:2]#[N:1])[C:4]#[N:5])[c:26]1[cH:27][cH:28][c:29]([O:30][c:31]2[cH:32][cH:33][cH:34][cH:35][cH:36]2)[cH:37][cH:38]1.[NH:6]([CH:7]1[CH2:8][CH:9]2[CH2:10][CH:11]1[CH2:12][N:13]2[C:14](=[O:15])[O:16][CH2:17][c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1)[NH2:24]>CCN(CC)CC.CCO>[N:1]#[C:2][c:3]1[c:4]([NH2:5])[n:6]([CH:7]2[CH2:8][CH:9]3[CH2:10][CH:11]2[CH2:12][N:13]3[C:14](=[O:15])[O:16][CH2:17][c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)[n:24][c:25]1-[c:26]1[cH:27][cH:28][c:29]([O:30][c:31]2[cH:32][cH:33][cH:34][cH:35][cH:36]2)[cH:37][cH:38]1\"}",
"reactionStep": {
"id": "sa_1d76f6b29194031f1952937c",
"reactionHash": "3c0e43606cbd5e084ea23567a256026b5f2b01e995a3199ec3c364fc78aee08e"
},
"children": [
{
"id": "8390",
"routeId": "sa_560419207ca574f4292cc5b7",
"moleculeId": "sa_90999b2a8b0ee1ad5b9594fd",
"parentId": "8389",
"isLeaf": false,
"molecule": {
"id": "sa_90999b2a8b0ee1ad5b9594fd",
"inchikey": "GBADLLJRHYSGES-UHFFFAOYSA-N",
"smiles": "NNC1CC2CC1CN2C(=O)OCc1ccccc1"
},
"smiles": "NNC1CC2CC1CN2C(=O)OCc1ccccc1",
"reactionStepId": "sa_6addae7050ecd4e612925115",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150291554A1;0299;1767550\",\"rsmi\":\"CC(C)(C)OC(=O)[NH:1][NH:2][CH:3]1[CH2:4][CH:5]2[CH2:6][CH:7]1[CH2:8][N:9]2[C:10](=[O:11])[O:12][CH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1>C1COCCO1.CO.Cl>[NH2:1][NH:2][CH:3]1[CH2:4][CH:5]2[CH2:6][CH:7]1[CH2:8][N:9]2[C:10](=[O:11])[O:12][CH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1\"},\"mapped_reaction_smiles\":\"CC(C)(C)OC(=O)[NH:1][NH:2][CH:3]1[CH2:4][CH:5]2[CH2:6][CH:7]1[CH2:8][N:9]2[C:10](=[O:11])[O:12][CH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1>C1COCCO1.CO.Cl>[NH2:1][NH:2][CH:3]1[CH2:4][CH:5]2[CH2:6][CH:7]1[CH2:8][N:9]2[C:10](=[O:11])[O:12][CH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1\"}",
"reactionStep": {
"id": "sa_6addae7050ecd4e612925115",
"reactionHash": "4ede9e8fc63131b42f0bfb9a37760603443cae2872cb09265248acdfbb528ffb"
},
"children": [
{
"id": "8391",
"routeId": "sa_560419207ca574f4292cc5b7",
"moleculeId": "sa_8ed6965baa4c184c50f963c8",
"parentId": "8390",
"isLeaf": false,
"molecule": {
"id": "sa_8ed6965baa4c184c50f963c8",
"inchikey": "IUNJXAKCORHSIM-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)NNC1CC2CC1CN2C(=O)OCc1ccccc1"
},
"smiles": "CC(C)(C)OC(=O)NNC1CC2CC1CN2C(=O)OCc1ccccc1",
"reactionStepId": "sa_92d13e6385bd7c46d3ec3f6b",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150291554A1;0298;1767549\",\"rsmi\":\"O=[C:10]1[CH2:11][CH:12]2[CH2:13][CH:14]1[CH2:15][N:16]2[C:17](=[O:18])[O:19][CH2:20][c:21]1[cH:22][cH:23][cH:24][cH:25][cH:26]1.[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][NH2:9]>C1CCOC1.Cc1ccc(S(=O)(=O)O)cc1.BC#N.[Na+]>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][NH:9][CH:10]1[CH2:11][CH:12]2[CH2:13][CH:14]1[CH2:15][N:16]2[C:17](=[O:18])[O:19][CH2:20][c:21]1[cH:22][cH:23][cH:24][cH:25][cH:26]1\"},\"mapped_reaction_smiles\":\"O=[C:10]1[CH2:11][CH:12]2[CH2:13][CH:14]1[CH2:15][N:16]2[C:17](=[O:18])[O:19][CH2:20][c:21]1[cH:22][cH:23][cH:24][cH:25][cH:26]1.[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][NH2:9]>C1CCOC1.Cc1ccc(S(=O)(=O)O)cc1.BC#N.[Na+]>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][NH:9][CH:10]1[CH2:11][CH:12]2[CH2:13][CH:14]1[CH2:15][N:16]2[C:17](=[O:18])[O:19][CH2:20][c:21]1[cH:22][cH:23][cH:24][cH:25][cH:26]1\"}",
"reactionStep": {
"id": "sa_92d13e6385bd7c46d3ec3f6b",
"reactionHash": "a87181178dc116fb661fe376021b394994b23fad7bb2e9a5478124454f4de154"
},
"children": [
{
"id": "8392",
"routeId": "sa_560419207ca574f4292cc5b7",
"moleculeId": "sa_153bc9a741c3fecd816c6a49",
"parentId": "8391",
"isLeaf": true,
"molecule": {
"id": "sa_153bc9a741c3fecd816c6a49",
"inchikey": "DKACXUFSLUYRFU-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(O)=NN"
},
"smiles": "CC(C)(C)OC(=O)NN",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "8393",
"routeId": "sa_560419207ca574f4292cc5b7",
"moleculeId": "sa_244af335d5edb0b523d08611",
"parentId": "8391",
"isLeaf": false,
"molecule": {
"id": "sa_244af335d5edb0b523d08611",
"inchikey": "GKBNRJQNBQXKON-UHFFFAOYSA-N",
"smiles": "O=C1CC2CC1CN2C(=O)OCc1ccccc1"
},
"smiles": "O=C1CC2CC1CN2C(=O)OCc1ccccc1",
"reactionStepId": "sa_7a0e0826f05aad39f1ff039c",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150291554A1;0297;1767548\",\"rsmi\":\"[OH:1][CH:2]1[CH2:3][CH:4]2[CH2:5][CH:6]1[CH2:7][N:8]2[C:9](=[O:10])[O:11][CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1>CC(=O)OI1(OC(C)=O)(OC(C)=O)OC(=O)c2ccccc21.ClCCl.O=C(O)O.O=S(O)(O)=S.[Na+].[Na+].[Na+].[Na+]>[O:1]=[C:2]1[CH2:3][CH:4]2[CH2:5][CH:6]1[CH2:7][N:8]2[C:9](=[O:10])[O:11][CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1\"},\"mapped_reaction_smiles\":\"[OH:1][CH:2]1[CH2:3][CH:4]2[CH2:5][CH:6]1[CH2:7][N:8]2[C:9](=[O:10])[O:11][CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1>CC(=O)OI1(OC(C)=O)(OC(C)=O)OC(=O)c2ccccc21.ClCCl.O=C(O)O.O=S(O)(O)=S.[Na+].[Na+].[Na+].[Na+]>[O:1]=[C:2]1[CH2:3][CH:4]2[CH2:5][CH:6]1[CH2:7][N:8]2[C:9](=[O:10])[O:11][CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1\"}",
"reactionStep": {
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"reactionHash": "da9ba51099efab0f1c5560b2232a6dd8ea997ae69fb85f30524db42eb4e177a1"
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"children": [
{
"id": "8394",
"routeId": "sa_560419207ca574f4292cc5b7",
"moleculeId": "sa_94a1e5f305d6f40257ddeb8d",
"parentId": "8393",
"isLeaf": true,
"molecule": {
"id": "sa_94a1e5f305d6f40257ddeb8d",
"inchikey": "MBWICDZTOSCKLV-UHFFFAOYSA-N",
"smiles": "O=C(OCc1ccccc1)N1CC2CC1CC2O"
},
"smiles": "O=C(OCc1ccccc1)N1CC2CC1CC2O",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
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}
]
}
]
}
]
},
{
"id": "8395",
"routeId": "sa_560419207ca574f4292cc5b7",
"moleculeId": "sa_f6dd8cd23a4a288b634f965f",
"parentId": "8389",
"isLeaf": true,
"molecule": {
"id": "sa_f6dd8cd23a4a288b634f965f",
"inchikey": "IRVRZQLHMPWLLY-UHFFFAOYSA-N",
"smiles": "COC(=C(C#N)C#N)c1ccc(Oc2ccccc2)cc1"
},
"smiles": "COC(=C(C#N)C#N)c1ccc(Oc2ccccc2)cc1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
}