Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
OCCN1CCN(c2ccc(Nc3ncc4c5ccnc(F)c5n(C5CCCC5)c4n3)nc2)CC1
InChiKey
GBCXEBUZWHRFBW-UHFFFAOYSA-N
Route Signature
24370249c3efce8e20907c3ff738c135aad519e6503f11907f3acad9f7f69a4d
Synthesis route with 4 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_be9d353a709ab1936da777d2",
"signature": "24370249c3efce8e20907c3ff738c135aad519e6503f11907f3acad9f7f69a4d",
"contentHash": "78da510e710ec7253ebf6a6cdbb1bdd95aba0a63bbc6aefa9f5bad0a6c8a22dd",
"length": 4,
"isConvergent": false
},
"target": {
"id": "sa_088cc0200436bc1accd302f5",
"benchmarkSetId": "61e696668b63e77d7c2a29c0821768e1c383de8313852d6e995224859494442e",
"targetId": "n5-01254",
"moleculeId": "sa_14cfe0973175d19e2e798775",
"smiles": "OCCN1CCN(c2ccc(Nc3ncc4c5ccnc(F)c5n(C5CCCC5)c4n3)nc2)CC1",
"routeLength": 4,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_14cfe0973175d19e2e798775",
"inchikey": "GBCXEBUZWHRFBW-UHFFFAOYSA-N",
"smiles": "OCCN1CCN(c2ccc(Nc3ncc4c5ccnc(F)c5n(C5CCCC5)c4n3)nc2)CC1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "14184",
"routeId": "sa_be9d353a709ab1936da777d2",
"moleculeId": "sa_14cfe0973175d19e2e798775",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_14cfe0973175d19e2e798775",
"inchikey": "GBCXEBUZWHRFBW-UHFFFAOYSA-N",
"smiles": "OCCN1CCN(c2ccc(Nc3ncc4c5ccnc(F)c5n(C5CCCC5)c4n3)nc2)CC1"
},
"smiles": "OCCN1CCN(c2ccc(Nc3ncc4c5ccnc(F)c5n(C5CCCC5)c4n3)nc2)CC1",
"reactionStepId": "sa_fb7ecdedeba51e8a43381e34",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20110142796A1;0499;1067314\",\"rsmi\":\"CC(C)(C)[Si](C)(C)[O:1][CH2:2][CH2:3][N:4]1[CH2:5][CH2:6][N:7]([c:8]2[cH:9][cH:10][c:11]([NH:12][c:13]3[n:14][c:15]4[c:16]([cH:17][n:18]3)[c:19]3[c:20]([c:21]([F:22])[n:23][cH:24][cH:25]3)[n:26]4[CH:27]3[CH2:28][CH2:29][CH2:30][CH2:31]3)[n:32][cH:33]2)[CH2:34][CH2:35]1>C1CCOC1.CCCC[N+](CCCC)(CCCC)CCCC.O.F.[Na+].O>[OH:1][CH2:2][CH2:3][N:4]1[CH2:5][CH2:6][N:7]([c:8]2[cH:9][cH:10][c:11]([NH:12][c:13]3[n:14][c:15]4[c:16]([cH:17][n:18]3)[c:19]3[c:20]([c:21]([F:22])[n:23][cH:24][cH:25]3)[n:26]4[CH:27]3[CH2:28][CH2:29][CH2:30][CH2:31]3)[n:32][cH:33]2)[CH2:34][CH2:35]1\"},\"mapped_reaction_smiles\":\"CC(C)(C)[Si](C)(C)[O:1][CH2:2][CH2:3][N:4]1[CH2:5][CH2:6][N:7]([c:8]2[cH:9][cH:10][c:11]([NH:12][c:13]3[n:14][c:15]4[c:16]([cH:17][n:18]3)[c:19]3[c:20]([c:21]([F:22])[n:23][cH:24][cH:25]3)[n:26]4[CH:27]3[CH2:28][CH2:29][CH2:30][CH2:31]3)[n:32][cH:33]2)[CH2:34][CH2:35]1>C1CCOC1.CCCC[N+](CCCC)(CCCC)CCCC.O.F.[Na+].O>[OH:1][CH2:2][CH2:3][N:4]1[CH2:5][CH2:6][N:7]([c:8]2[cH:9][cH:10][c:11]([NH:12][c:13]3[n:14][c:15]4[c:16]([cH:17][n:18]3)[c:19]3[c:20]([c:21]([F:22])[n:23][cH:24][cH:25]3)[n:26]4[CH:27]3[CH2:28][CH2:29][CH2:30][CH2:31]3)[n:32][cH:33]2)[CH2:34][CH2:35]1\"}",
"reactionStep": {
"id": "sa_fb7ecdedeba51e8a43381e34",
"reactionHash": "702acb990e6309c18b01b4cdcf040bc37f86ea0a902e628c0c0d374613fb4f7f"
},
"children": [
{
"id": "14185",
"routeId": "sa_be9d353a709ab1936da777d2",
"moleculeId": "sa_b403d1ac4e60714c4001b0b0",
"parentId": "14184",
"isLeaf": false,
"molecule": {
"id": "sa_b403d1ac4e60714c4001b0b0",
"inchikey": "OMKBQQSRWZPGJW-UHFFFAOYSA-N",
"smiles": "CC(C)(C)[Si](C)(C)OCCN1CCN(c2ccc(Nc3ncc4c5ccnc(F)c5n(C5CCCC5)c4n3)nc2)CC1"
},
"smiles": "CC(C)(C)[Si](C)(C)OCCN1CCN(c2ccc(Nc3ncc4c5ccnc(F)c5n(C5CCCC5)c4n3)nc2)CC1",
"reactionStepId": "sa_214a7e821342e8851d29e9a4",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20110142796A1;0498;1067313\",\"rsmi\":\"Cl[c:18]1[n:17][cH:16][c:15]([N:14]2[CH2:13][CH2:12][N:11]([CH2:10][CH2:9][O:8][Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([CH3:6])[CH3:7])[CH2:42][CH2:41]2)[cH:40][cH:39]1.[NH2:19][c:20]1[n:21][c:22]2[c:23]([cH:24][n:25]1)[c:26]1[c:27]([c:28]([F:29])[n:30][cH:31][cH:32]1)[n:33]2[CH:34]1[CH2:35][CH2:36][CH2:37][CH2:38]1>CC(C)(C)O.CC1(C)c2cccc(P(c3ccccc3)c3ccccc3)c2Oc2c(P(c3ccccc3)c3ccccc3)cccc21.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.[Na+].[Pd].[Pd]>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][CH2:9][CH2:10][N:11]1[CH2:12][CH2:13][N:14]([c:15]2[cH:16][n:17][c:18]([NH:19][c:20]3[n:21][c:22]4[c:23]([cH:24][n:25]3)[c:26]3[c:27]([c:28]([F:29])[n:30][cH:31][cH:32]3)[n:33]4[CH:34]3[CH2:35][CH2:36][CH2:37][CH2:38]3)[cH:39][cH:40]2)[CH2:41][CH2:42]1\"},\"mapped_reaction_smiles\":\"Cl[c:18]1[n:17][cH:16][c:15]([N:14]2[CH2:13][CH2:12][N:11]([CH2:10][CH2:9][O:8][Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([CH3:6])[CH3:7])[CH2:42][CH2:41]2)[cH:40][cH:39]1.[NH2:19][c:20]1[n:21][c:22]2[c:23]([cH:24][n:25]1)[c:26]1[c:27]([c:28]([F:29])[n:30][cH:31][cH:32]1)[n:33]2[CH:34]1[CH2:35][CH2:36][CH2:37][CH2:38]1>CC(C)(C)O.CC1(C)c2cccc(P(c3ccccc3)c3ccccc3)c2Oc2c(P(c3ccccc3)c3ccccc3)cccc21.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.[Na+].[Pd].[Pd]>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][CH2:9][CH2:10][N:11]1[CH2:12][CH2:13][N:14]([c:15]2[cH:16][n:17][c:18]([NH:19][c:20]3[n:21][c:22]4[c:23]([cH:24][n:25]3)[c:26]3[c:27]([c:28]([F:29])[n:30][cH:31][cH:32]3)[n:33]4[CH:34]3[CH2:35][CH2:36][CH2:37][CH2:38]3)[cH:39][cH:40]2)[CH2:41][CH2:42]1\"}",
"reactionStep": {
"id": "sa_214a7e821342e8851d29e9a4",
"reactionHash": "dc4eced47d931a9d638d85e3c8b864778dfd372551eaa634f3ea18cdd4328021"
},
"children": [
{
"id": "14186",
"routeId": "sa_be9d353a709ab1936da777d2",
"moleculeId": "sa_bb8886d3862cbb1c63a6e1e8",
"parentId": "14185",
"isLeaf": false,
"molecule": {
"id": "sa_bb8886d3862cbb1c63a6e1e8",
"inchikey": "JTIFEHVVMZWNCJ-UHFFFAOYSA-N",
"smiles": "CC(C)(C)[Si](C)(C)OCCN1CCN(c2ccc(Cl)nc2)CC1"
},
"smiles": "CC(C)(C)[Si](C)(C)OCCN1CCN(c2ccc(Cl)nc2)CC1",
"reactionStepId": "sa_d0760ee7aeee19a3c0710770",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20110142796A1;0497;1067312\",\"rsmi\":\"Br[c:15]1[cH:16][cH:17][c:18]([Cl:19])[n:20][cH:21]1.[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][CH2:9][CH2:10][N:11]1[CH2:12][CH2:13][NH:14][CH2:22][CH2:23]1>CC(C)(C)O.CC1(C)c2cccc(P(c3ccccc3)c3ccccc3)c2Oc2c(P(c3ccccc3)c3ccccc3)cccc21.Cc1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(O)O.[Na+].[Na+].[Pd].[Pd]>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][CH2:9][CH2:10][N:11]1[CH2:12][CH2:13][N:14]([c:15]2[cH:16][cH:17][c:18]([Cl:19])[n:20][cH:21]2)[CH2:22][CH2:23]1\"},\"mapped_reaction_smiles\":\"Br[c:15]1[cH:16][cH:17][c:18]([Cl:19])[n:20][cH:21]1.[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][CH2:9][CH2:10][N:11]1[CH2:12][CH2:13][NH:14][CH2:22][CH2:23]1>CC(C)(C)O.CC1(C)c2cccc(P(c3ccccc3)c3ccccc3)c2Oc2c(P(c3ccccc3)c3ccccc3)cccc21.Cc1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(O)O.[Na+].[Na+].[Pd].[Pd]>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][CH2:9][CH2:10][N:11]1[CH2:12][CH2:13][N:14]([c:15]2[cH:16][cH:17][c:18]([Cl:19])[n:20][cH:21]2)[CH2:22][CH2:23]1\"}",
"reactionStep": {
"id": "sa_d0760ee7aeee19a3c0710770",
"reactionHash": "afaccde51d7bb7718ddf54bccc47a8ad552c8c0ae0f919efe521fd6ea6820be6"
},
"children": [
{
"id": "14187",
"routeId": "sa_be9d353a709ab1936da777d2",
"moleculeId": "sa_29b4f96dee5078902a114b49",
"parentId": "14186",
"isLeaf": true,
"molecule": {
"id": "sa_29b4f96dee5078902a114b49",
"inchikey": "PEAOEIWYQVXZMB-UHFFFAOYSA-N",
"smiles": "Clc1ccc(Br)cn1"
},
"smiles": "Clc1ccc(Br)cn1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "14188",
"routeId": "sa_be9d353a709ab1936da777d2",
"moleculeId": "sa_1a538700ac098a937a994b12",
"parentId": "14186",
"isLeaf": false,
"molecule": {
"id": "sa_1a538700ac098a937a994b12",
"inchikey": "XCNFGWPHWMLMLX-UHFFFAOYSA-N",
"smiles": "CC(C)(C)[Si](C)(C)OCCN1CCNCC1"
},
"smiles": "CC(C)(C)[Si](C)(C)OCCN1CCNCC1",
"reactionStepId": "sa_877c6660573b25a792747418",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20110142796A1;0496;1067311\",\"rsmi\":\"Cl[Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([CH3:6])[CH3:7].[OH:8][CH2:9][CH2:10][N:11]1[CH2:12][CH2:13][NH:14][CH2:15][CH2:16]1>ClCCl>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][CH2:9][CH2:10][N:11]1[CH2:12][CH2:13][NH:14][CH2:15][CH2:16]1\"},\"mapped_reaction_smiles\":\"Cl[Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([CH3:6])[CH3:7].[OH:8][CH2:9][CH2:10][N:11]1[CH2:12][CH2:13][NH:14][CH2:15][CH2:16]1>ClCCl>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][CH2:9][CH2:10][N:11]1[CH2:12][CH2:13][NH:14][CH2:15][CH2:16]1\"}",
"reactionStep": {
"id": "sa_877c6660573b25a792747418",
"reactionHash": "bc23ec198c08138239cc5f51cc3cf7731381b2a5c1866cb1726002ef6ce11852"
},
"children": [
{
"id": "14189",
"routeId": "sa_be9d353a709ab1936da777d2",
"moleculeId": "sa_1785e67b778eb91f7e04c15a",
"parentId": "14188",
"isLeaf": true,
"molecule": {
"id": "sa_1785e67b778eb91f7e04c15a",
"inchikey": "BCNZYOJHNLTNEZ-UHFFFAOYSA-N",
"smiles": "CC(C)(C)[Si](C)(C)Cl"
},
"smiles": "CC(C)(C)[Si](C)(C)Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "14190",
"routeId": "sa_be9d353a709ab1936da777d2",
"moleculeId": "sa_4ef40a59f2f2a5426fb1546b",
"parentId": "14188",
"isLeaf": true,
"molecule": {
"id": "sa_4ef40a59f2f2a5426fb1546b",
"inchikey": "WFCSWCVEJLETKA-UHFFFAOYSA-N",
"smiles": "OCCN1CCNCC1"
},
"smiles": "OCCN1CCNCC1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
},
{
"id": "14191",
"routeId": "sa_be9d353a709ab1936da777d2",
"moleculeId": "sa_a9380bddad21e0ed45eb8e77",
"parentId": "14185",
"isLeaf": true,
"molecule": {
"id": "sa_a9380bddad21e0ed45eb8e77",
"inchikey": "PNSXNWGSTDKJAO-UHFFFAOYSA-N",
"smiles": "Nc1ncc2c3ccnc(F)c3n(C3CCCC3)c2n1"
},
"smiles": "Nc1ncc2c3ccnc(F)c3n(C3CCCC3)c2n1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
}