Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CC(C)OC(=O)N1CCC(Oc2cc(N3CCc4cc(SCCO[Si](C)(C)C(C)(C)C)ccc43)ncn2)CC1
InChiKey
PRVKYUZUICKLAW-UHFFFAOYSA-N
Route Signature
6243d4a39fa180c79f3cb8b4206de0b0f1fa811a90c01757fac2c1a53e715ea1
Synthesis route with 4 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_a8e8751b378df5c583c09222",
"signature": "6243d4a39fa180c79f3cb8b4206de0b0f1fa811a90c01757fac2c1a53e715ea1",
"contentHash": "fd8fb0cbb083e1294350e337302b742681f913bbb5d2d98957357720d25e6532",
"length": 4,
"isConvergent": true
},
"target": {
"id": "sa_52ebea74aecc5acfa7a47baf",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-00284",
"moleculeId": "sa_1e6d50bdada22f63b7ecf5e3",
"smiles": "CC(C)OC(=O)N1CCC(Oc2cc(N3CCc4cc(SCCO[Si](C)(C)C(C)(C)C)ccc43)ncn2)CC1",
"routeLength": 4,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_1e6d50bdada22f63b7ecf5e3",
"inchikey": "PRVKYUZUICKLAW-UHFFFAOYSA-N",
"smiles": "CC(C)OC(=O)N1CCC(Oc2cc(N3CCc4cc(SCCO[Si](C)(C)C(C)(C)C)ccc43)ncn2)CC1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "563",
"routeId": "sa_a8e8751b378df5c583c09222",
"moleculeId": "sa_1e6d50bdada22f63b7ecf5e3",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_1e6d50bdada22f63b7ecf5e3",
"inchikey": "PRVKYUZUICKLAW-UHFFFAOYSA-N",
"smiles": "CC(C)OC(=O)N1CCC(Oc2cc(N3CCc4cc(SCCO[Si](C)(C)C(C)(C)C)ccc43)ncn2)CC1"
},
"smiles": "CC(C)OC(=O)N1CCC(Oc2cc(N3CCc4cc(SCCO[Si](C)(C)C(C)(C)C)ccc43)ncn2)CC1",
"reactionStepId": "sa_ce8990280aac70d8c8fabc8e",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20120052130A1;0324;1185566\",\"rsmi\":\"Cl[c:16]1[n:15][cH:14][n:13][c:12]([O:11][CH:10]2[CH2:9][CH2:8][N:7]([C:5]([O:4][CH:2]([CH3:1])[CH3:3])=[O:6])[CH2:39][CH2:38]2)[cH:37]1.[NH:17]1[CH2:18][CH2:19][c:20]2[cH:21][c:22]([S:23][CH2:24][CH2:25][O:26][Si:27]([CH3:28])([CH3:29])[C:30]([CH3:31])([CH3:32])[CH3:33])[cH:34][cH:35][c:36]21>C1CCOC1.C1COCCO1.C[Si](C)(C)N[Si](C)(C)C.[Na+]>[CH3:1][CH:2]([CH3:3])[O:4][C:5](=[O:6])[N:7]1[CH2:8][CH2:9][CH:10]([O:11][c:12]2[n:13][cH:14][n:15][c:16]([N:17]3[CH2:18][CH2:19][c:20]4[cH:21][c:22]([S:23][CH2:24][CH2:25][O:26][Si:27]([CH3:28])([CH3:29])[C:30]([CH3:31])([CH3:32])[CH3:33])[cH:34][cH:35][c:36]43)[cH:37]2)[CH2:38][CH2:39]1\"},\"mapped_reaction_smiles\":\"Cl[c:16]1[n:15][cH:14][n:13][c:12]([O:11][CH:10]2[CH2:9][CH2:8][N:7]([C:5]([O:4][CH:2]([CH3:1])[CH3:3])=[O:6])[CH2:39][CH2:38]2)[cH:37]1.[NH:17]1[CH2:18][CH2:19][c:20]2[cH:21][c:22]([S:23][CH2:24][CH2:25][O:26][Si:27]([CH3:28])([CH3:29])[C:30]([CH3:31])([CH3:32])[CH3:33])[cH:34][cH:35][c:36]21>C1CCOC1.C1COCCO1.C[Si](C)(C)N[Si](C)(C)C.[Na+]>[CH3:1][CH:2]([CH3:3])[O:4][C:5](=[O:6])[N:7]1[CH2:8][CH2:9][CH:10]([O:11][c:12]2[n:13][cH:14][n:15][c:16]([N:17]3[CH2:18][CH2:19][c:20]4[cH:21][c:22]([S:23][CH2:24][CH2:25][O:26][Si:27]([CH3:28])([CH3:29])[C:30]([CH3:31])([CH3:32])[CH3:33])[cH:34][cH:35][c:36]43)[cH:37]2)[CH2:38][CH2:39]1\"}",
"reactionStep": {
"id": "sa_ce8990280aac70d8c8fabc8e",
"reactionHash": "ed8ca2daa592d0b69d1d097ce31f42e0c02a2538f1952f0b5c8229d1dea21794"
},
"children": [
{
"id": "564",
"routeId": "sa_a8e8751b378df5c583c09222",
"moleculeId": "sa_8c6ce8e2ec55efd601b5437c",
"parentId": "563",
"isLeaf": false,
"molecule": {
"id": "sa_8c6ce8e2ec55efd601b5437c",
"inchikey": "IMOMGGWBQUKAIC-UHFFFAOYSA-N",
"smiles": "CC(C)(C)[Si](C)(C)OCCSc1ccc2c(c1)CCN2"
},
"smiles": "CC(C)(C)[Si](C)(C)OCCSc1ccc2c(c1)CCN2",
"reactionStepId": "sa_f5a356acd03837b53b216bd5",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20120052130A1;0208;1185538\",\"rsmi\":\"Cl[Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([CH3:6])[CH3:7].[OH:8][CH2:9][CH2:10][S:11][c:12]1[cH:13][cH:14][c:15]2[c:19]([cH:20]1)[CH2:18][CH2:17][NH:16]2>CCN(CC)CC.CN(C)c1ccncc1.ClCCl>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][CH2:9][CH2:10][S:11][c:12]1[cH:13][cH:14][c:15]2[c:19]([cH:20]1)[CH2:18][CH2:17][NH:16]2\"},\"mapped_reaction_smiles\":\"Cl[Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([CH3:6])[CH3:7].[OH:8][CH2:9][CH2:10][S:11][c:12]1[cH:13][cH:14][c:15]2[c:19]([cH:20]1)[CH2:18][CH2:17][NH:16]2>CCN(CC)CC.CN(C)c1ccncc1.ClCCl>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][CH2:9][CH2:10][S:11][c:12]1[cH:13][cH:14][c:15]2[c:19]([cH:20]1)[CH2:18][CH2:17][NH:16]2\"}",
"reactionStep": {
"id": "sa_f5a356acd03837b53b216bd5",
"reactionHash": "f5a8a08a7dad89ddda9523fc644c0501b01df62242309507586198ee71ccf915"
},
"children": [
{
"id": "565",
"routeId": "sa_a8e8751b378df5c583c09222",
"moleculeId": "sa_1785e67b778eb91f7e04c15a",
"parentId": "564",
"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": "566",
"routeId": "sa_a8e8751b378df5c583c09222",
"moleculeId": "sa_9b9aeec89583a14134d15ea9",
"parentId": "564",
"isLeaf": false,
"molecule": {
"id": "sa_9b9aeec89583a14134d15ea9",
"inchikey": "XLYTVZHVQGLEAL-UHFFFAOYSA-N",
"smiles": "OCCSc1ccc2c(c1)CCN2"
},
"smiles": "OCCSc1ccc2c(c1)CCN2",
"reactionStepId": "sa_d0de8bc97bb68d1ceaf66aa2",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20120052130A1;0206;1185537\",\"rsmi\":\"CC(C)(C)OC(=O)[N:9]1[c:8]2[cH:7][cH:6][c:5]([S:4][CH2:3][CH2:2][OH:1])[cH:13][c:12]2[CH2:11][CH2:10]1>C1COCCO1.Cl>[OH:1][CH2:2][CH2:3][S:4][c:5]1[cH:6][cH:7][c:8]2[c:12]([cH:13]1)[CH2:11][CH2:10][NH:9]2\"},\"mapped_reaction_smiles\":\"CC(C)(C)OC(=O)[N:9]1[c:8]2[cH:7][cH:6][c:5]([S:4][CH2:3][CH2:2][OH:1])[cH:13][c:12]2[CH2:11][CH2:10]1>C1COCCO1.Cl>[OH:1][CH2:2][CH2:3][S:4][c:5]1[cH:6][cH:7][c:8]2[c:12]([cH:13]1)[CH2:11][CH2:10][NH:9]2\"}",
"reactionStep": {
"id": "sa_d0de8bc97bb68d1ceaf66aa2",
"reactionHash": "9dd031b6e59f3b7c4411c75c3f382b9ed51e4345dc34c9c6e43ee963ade21882"
},
"children": [
{
"id": "567",
"routeId": "sa_a8e8751b378df5c583c09222",
"moleculeId": "sa_3bc329bb78051d0eec464b3e",
"parentId": "566",
"isLeaf": false,
"molecule": {
"id": "sa_3bc329bb78051d0eec464b3e",
"inchikey": "XQHOGENOUUESHJ-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)N1CCc2cc(SCCO)ccc21"
},
"smiles": "CC(C)(C)OC(=O)N1CCc2cc(SCCO)ccc21",
"reactionStepId": "sa_4ac3d4f7034f071b6ada0772",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20120052130A1;0204;1185536\",\"rsmi\":\"Br[c:13]1[cH:12][c:11]2[c:20]([cH:19][cH:18]1)[N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:9][CH2:10]2.[SH:14][CH2:15][CH2:16][OH:17]>C1COCCO1.CC1(C)c2cccc(P(c3ccccc3)c3ccccc3)c2Oc2c(P(c3ccccc3)c3ccccc3)cccc21.CCN(C(C)C)C(C)C.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.[Pd].[Pd]>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][c:11]2[cH:12][c:13]([S:14][CH2:15][CH2:16][OH:17])[cH:18][cH:19][c:20]21\"},\"mapped_reaction_smiles\":\"Br[c:13]1[cH:12][c:11]2[c:20]([cH:19][cH:18]1)[N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:9][CH2:10]2.[SH:14][CH2:15][CH2:16][OH:17]>C1COCCO1.CC1(C)c2cccc(P(c3ccccc3)c3ccccc3)c2Oc2c(P(c3ccccc3)c3ccccc3)cccc21.CCN(C(C)C)C(C)C.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.[Pd].[Pd]>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][c:11]2[cH:12][c:13]([S:14][CH2:15][CH2:16][OH:17])[cH:18][cH:19][c:20]21\"}",
"reactionStep": {
"id": "sa_4ac3d4f7034f071b6ada0772",
"reactionHash": "ff997a6b54101ef136792384541852cd76eb639969f0802a21183957e2a0a392"
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"children": [
{
"id": "568",
"routeId": "sa_a8e8751b378df5c583c09222",
"moleculeId": "sa_3694f7c7c4529b136a9163e8",
"parentId": "567",
"isLeaf": true,
"molecule": {
"id": "sa_3694f7c7c4529b136a9163e8",
"inchikey": "DGVVWUTYPXICAM-UHFFFAOYSA-N",
"smiles": "OCCS"
},
"smiles": "OCCS",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "569",
"routeId": "sa_a8e8751b378df5c583c09222",
"moleculeId": "sa_aa46d1dc3fc96b4000be9d81",
"parentId": "567",
"isLeaf": true,
"molecule": {
"id": "sa_aa46d1dc3fc96b4000be9d81",
"inchikey": "UOCVSZYBRMGQOL-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)N1CCc2cc(Br)ccc21"
},
"smiles": "CC(C)(C)OC(=O)N1CCc2cc(Br)ccc21",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
]
},
{
"id": "570",
"routeId": "sa_a8e8751b378df5c583c09222",
"moleculeId": "sa_a3a8e98e7db386135298e597",
"parentId": "563",
"isLeaf": false,
"molecule": {
"id": "sa_a3a8e98e7db386135298e597",
"inchikey": "STMIYUDJPLTMGL-UHFFFAOYSA-N",
"smiles": "CC(C)OC(=O)N1CCC(Oc2cc(Cl)ncn2)CC1"
},
"smiles": "CC(C)OC(=O)N1CCC(Oc2cc(Cl)ncn2)CC1",
"reactionStepId": "sa_36c4b30b7172a96355905a54",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20120052130A1;0196;1185532\",\"rsmi\":\"Cl[c:12]1[n:13][cH:14][n:15][c:16]([Cl:17])[cH:18]1.[CH3:1][CH:2]([CH3:3])[O:4][C:5](=[O:6])[N:7]1[CH2:8][CH2:9][CH:10]([OH:11])[CH2:19][CH2:20]1>C1CCOC1.CC(C)(C)O.O.[K+]>[CH3:1][CH:2]([CH3:3])[O:4][C:5](=[O:6])[N:7]1[CH2:8][CH2:9][CH:10]([O:11][c:12]2[n:13][cH:14][n:15][c:16]([Cl:17])[cH:18]2)[CH2:19][CH2:20]1\"},\"mapped_reaction_smiles\":\"Cl[c:12]1[n:13][cH:14][n:15][c:16]([Cl:17])[cH:18]1.[CH3:1][CH:2]([CH3:3])[O:4][C:5](=[O:6])[N:7]1[CH2:8][CH2:9][CH:10]([OH:11])[CH2:19][CH2:20]1>C1CCOC1.CC(C)(C)O.O.[K+]>[CH3:1][CH:2]([CH3:3])[O:4][C:5](=[O:6])[N:7]1[CH2:8][CH2:9][CH:10]([O:11][c:12]2[n:13][cH:14][n:15][c:16]([Cl:17])[cH:18]2)[CH2:19][CH2:20]1\"}",
"reactionStep": {
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"reactionHash": "460d8d8de151c916289e351fffc2465ca08f6dbb405506bde72397f12e8b21a5"
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"children": [
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"moleculeId": "sa_a424b955606b6e71574eae42",
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"isLeaf": true,
"molecule": {
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"inchikey": "UKVIBHRSFKWRPA-UHFFFAOYSA-N",
"smiles": "CC(C)OC(=O)N1CCC(O)CC1"
},
"smiles": "CC(C)OC(=O)N1CCC(O)CC1",
"reactionStepId": null,
"template": null,
"metadata": null,
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"children": []
},
{
"id": "572",
"routeId": "sa_a8e8751b378df5c583c09222",
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"parentId": "570",
"isLeaf": true,
"molecule": {
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"inchikey": "XJPZKYIHCLDXST-UHFFFAOYSA-N",
"smiles": "Clc1cc(Cl)ncn1"
},
"smiles": "Clc1cc(Cl)ncn1",
"reactionStepId": null,
"template": null,
"metadata": null,
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}
]
}
]
}
}