Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
Cn1nc(-c2ccc(OC(F)(F)F)cc2)cc1COc1ccc2c(ccn2CC(=O)O)c1
InChiKey
MHDACQLIQRYWFQ-UHFFFAOYSA-N
Route Signature
4e537eb40b96b42572cf52d235af67d04399d6da8a29c1ee3c356ba3f183a6f3
Synthesis route with 5 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_ee21244c374dc044bda28ccd",
"signature": "4e537eb40b96b42572cf52d235af67d04399d6da8a29c1ee3c356ba3f183a6f3",
"contentHash": "f0b883fbff3fe9e5de65567d0aa94575c5365e445bf37a33fe4d130ed9131f59",
"length": 5,
"isConvergent": true
},
"target": {
"id": "sa_c61321543e54dbeaac74aba8",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-00680",
"moleculeId": "sa_59b6b9d2ff52856c9da0225b",
"smiles": "Cn1nc(-c2ccc(OC(F)(F)F)cc2)cc1COc1ccc2c(ccn2CC(=O)O)c1",
"routeLength": 5,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_59b6b9d2ff52856c9da0225b",
"inchikey": "MHDACQLIQRYWFQ-UHFFFAOYSA-N",
"smiles": "Cn1nc(-c2ccc(OC(F)(F)F)cc2)cc1COc1ccc2c(ccn2CC(=O)O)c1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "9652",
"routeId": "sa_ee21244c374dc044bda28ccd",
"moleculeId": "sa_59b6b9d2ff52856c9da0225b",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_59b6b9d2ff52856c9da0225b",
"inchikey": "MHDACQLIQRYWFQ-UHFFFAOYSA-N",
"smiles": "Cn1nc(-c2ccc(OC(F)(F)F)cc2)cc1COc1ccc2c(ccn2CC(=O)O)c1"
},
"smiles": "Cn1nc(-c2ccc(OC(F)(F)F)cc2)cc1COc1ccc2c(ccn2CC(=O)O)c1",
"reactionStepId": "sa_d91153f5eedbdea5a5b786f6",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US07265149B2;0303;804633\",\"rsmi\":\"CC[O:32][C:30]([CH2:29][n:28]1[c:23]2[cH:22][cH:21][c:20]([O:19][CH2:18][c:17]3[n:2]([CH3:1])[n:3][c:4](-[c:5]4[cH:6][cH:7][c:8]([O:9][C:10]([F:11])([F:12])[F:13])[cH:14][cH:15]4)[cH:16]3)[cH:25][c:24]2[cH:26][cH:27]1)=[O:31]>[Li+].O>[CH3:1][n:2]1[n:3][c:4](-[c:5]2[cH:6][cH:7][c:8]([O:9][C:10]([F:11])([F:12])[F:13])[cH:14][cH:15]2)[cH:16][c:17]1[CH2:18][O:19][c:20]1[cH:21][cH:22][c:23]2[c:24]([cH:25]1)[cH:26][cH:27][n:28]2[CH2:29][C:30](=[O:31])[OH:32]\"},\"mapped_reaction_smiles\":\"CC[O:32][C:30]([CH2:29][n:28]1[c:23]2[cH:22][cH:21][c:20]([O:19][CH2:18][c:17]3[n:2]([CH3:1])[n:3][c:4](-[c:5]4[cH:6][cH:7][c:8]([O:9][C:10]([F:11])([F:12])[F:13])[cH:14][cH:15]4)[cH:16]3)[cH:25][c:24]2[cH:26][cH:27]1)=[O:31]>[Li+].O>[CH3:1][n:2]1[n:3][c:4](-[c:5]2[cH:6][cH:7][c:8]([O:9][C:10]([F:11])([F:12])[F:13])[cH:14][cH:15]2)[cH:16][c:17]1[CH2:18][O:19][c:20]1[cH:21][cH:22][c:23]2[c:24]([cH:25]1)[cH:26][cH:27][n:28]2[CH2:29][C:30](=[O:31])[OH:32]\"}",
"reactionStep": {
"id": "sa_d91153f5eedbdea5a5b786f6",
"reactionHash": "878d1f9bcbff48fcf053610b1e7fd5022fc1c325dd4d238253f33513df8fcd58"
},
"children": [
{
"id": "9653",
"routeId": "sa_ee21244c374dc044bda28ccd",
"moleculeId": "sa_0c3b8e681d63051e9ce9669e",
"parentId": "9652",
"isLeaf": false,
"molecule": {
"id": "sa_0c3b8e681d63051e9ce9669e",
"inchikey": "UDXRTSUMSCDYTQ-UHFFFAOYSA-N",
"smiles": "CCOC(=O)Cn1ccc2cc(OCc3cc(-c4ccc(OC(F)(F)F)cc4)nn3C)ccc21"
},
"smiles": "CCOC(=O)Cn1ccc2cc(OCc3cc(-c4ccc(OC(F)(F)F)cc4)nn3C)ccc21",
"reactionStepId": "sa_fdc548e8713c3740349d584b",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US07265149B2;0301;804632\",\"rsmi\":\"O[c:12]1[cH:11][c:10]2[cH:9][cH:8][n:7]([CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:34]2[cH:33][cH:32]1.[OH:13][CH2:14][c:15]1[cH:16][c:17](-[c:18]2[cH:19][cH:20][c:21]([O:22][C:23]([F:24])([F:25])[F:26])[cH:27][cH:28]2)[n:29][n:30]1[CH3:31]>CCCCP(CCCC)CCCC.CN(C)C(=O)N=NC(=O)N(C)C>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][n:7]1[cH:8][cH:9][c:10]2[cH:11][c:12]([O:13][CH2:14][c:15]3[cH:16][c:17](-[c:18]4[cH:19][cH:20][c:21]([O:22][C:23]([F:24])([F:25])[F:26])[cH:27][cH:28]4)[n:29][n:30]3[CH3:31])[cH:32][cH:33][c:34]12\"},\"mapped_reaction_smiles\":\"O[c:12]1[cH:11][c:10]2[cH:9][cH:8][n:7]([CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:34]2[cH:33][cH:32]1.[OH:13][CH2:14][c:15]1[cH:16][c:17](-[c:18]2[cH:19][cH:20][c:21]([O:22][C:23]([F:24])([F:25])[F:26])[cH:27][cH:28]2)[n:29][n:30]1[CH3:31]>CCCCP(CCCC)CCCC.CN(C)C(=O)N=NC(=O)N(C)C>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][n:7]1[cH:8][cH:9][c:10]2[cH:11][c:12]([O:13][CH2:14][c:15]3[cH:16][c:17](-[c:18]4[cH:19][cH:20][c:21]([O:22][C:23]([F:24])([F:25])[F:26])[cH:27][cH:28]4)[n:29][n:30]3[CH3:31])[cH:32][cH:33][c:34]12\"}",
"reactionStep": {
"id": "sa_fdc548e8713c3740349d584b",
"reactionHash": "d69171c5116eebf53ee778767b73b7120a913e0220945380ba703b49811a8dfe"
},
"children": [
{
"id": "9654",
"routeId": "sa_ee21244c374dc044bda28ccd",
"moleculeId": "sa_11f8943ff9e74470ba1ad165",
"parentId": "9653",
"isLeaf": false,
"molecule": {
"id": "sa_11f8943ff9e74470ba1ad165",
"inchikey": "FKMUOQRGDODMEL-UHFFFAOYSA-N",
"smiles": "CCOC(=O)Cn1ccc2cc(O)ccc21"
},
"smiles": "CCOC(=O)Cn1ccc2cc(O)ccc21",
"reactionStepId": "sa_187771c269a2a3860e21debf",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US07265149B2;0299;804631\",\"rsmi\":\"CC(C)(C)[Si](C)(C)[O:13][c:12]1[cH:11][c:10]2[cH:9][cH:8][n:7]([CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:16]2[cH:15][cH:14]1>C1CCOC1.CCCC[N+](CCCC)(CCCC)CCCC.CCOCC.O.F>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][n:7]1[cH:8][cH:9][c:10]2[cH:11][c:12]([OH:13])[cH:14][cH:15][c:16]12\"},\"mapped_reaction_smiles\":\"CC(C)(C)[Si](C)(C)[O:13][c:12]1[cH:11][c:10]2[cH:9][cH:8][n:7]([CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:16]2[cH:15][cH:14]1>C1CCOC1.CCCC[N+](CCCC)(CCCC)CCCC.CCOCC.O.F>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][n:7]1[cH:8][cH:9][c:10]2[cH:11][c:12]([OH:13])[cH:14][cH:15][c:16]12\"}",
"reactionStep": {
"id": "sa_187771c269a2a3860e21debf",
"reactionHash": "19d5cc1197336a645bafde888ee4dc506d6a9901255c6e5a952875b69998a950"
},
"children": [
{
"id": "9655",
"routeId": "sa_ee21244c374dc044bda28ccd",
"moleculeId": "sa_43931ab81bb82e09bd142a63",
"parentId": "9654",
"isLeaf": false,
"molecule": {
"id": "sa_43931ab81bb82e09bd142a63",
"inchikey": "UYSYGFKMTQTZIN-UHFFFAOYSA-N",
"smiles": "CCOC(=O)Cn1ccc2cc(O[Si](C)(C)C(C)(C)C)ccc21"
},
"smiles": "CCOC(=O)Cn1ccc2cc(O[Si](C)(C)C(C)(C)C)ccc21",
"reactionStepId": "sa_a389a3cb45d024de8765ed82",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US07265149B2;0297;804630\",\"rsmi\":\"Br[CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5].[nH:7]1[cH:8][cH:9][c:10]2[cH:11][c:12]([O:13][Si:14]([CH3:15])([CH3:16])[C:17]([CH3:18])([CH3:19])[CH3:20])[cH:21][cH:22][c:23]12>CCOCC.CN(C)C=O.O=C(O)O.[Cs+].[Cs+]>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][n:7]1[cH:8][cH:9][c:10]2[cH:11][c:12]([O:13][Si:14]([CH3:15])([CH3:16])[C:17]([CH3:18])([CH3:19])[CH3:20])[cH:21][cH:22][c:23]12\"},\"mapped_reaction_smiles\":\"Br[CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5].[nH:7]1[cH:8][cH:9][c:10]2[cH:11][c:12]([O:13][Si:14]([CH3:15])([CH3:16])[C:17]([CH3:18])([CH3:19])[CH3:20])[cH:21][cH:22][c:23]12>CCOCC.CN(C)C=O.O=C(O)O.[Cs+].[Cs+]>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][n:7]1[cH:8][cH:9][c:10]2[cH:11][c:12]([O:13][Si:14]([CH3:15])([CH3:16])[C:17]([CH3:18])([CH3:19])[CH3:20])[cH:21][cH:22][c:23]12\"}",
"reactionStep": {
"id": "sa_a389a3cb45d024de8765ed82",
"reactionHash": "056269dfc498739c1f7f8afe12f58970b7c78135c883441d12506900a6c37136"
},
"children": [
{
"id": "9656",
"routeId": "sa_ee21244c374dc044bda28ccd",
"moleculeId": "sa_b4300e12a33d6c69467448a0",
"parentId": "9655",
"isLeaf": false,
"molecule": {
"id": "sa_b4300e12a33d6c69467448a0",
"inchikey": "LUUANNCTVICLCJ-UHFFFAOYSA-N",
"smiles": "CC(C)(C)[Si](C)(C)Oc1ccc2[nH]ccc2c1"
},
"smiles": "CC(C)(C)[Si](C)(C)Oc1ccc2[nH]ccc2c1",
"reactionStepId": "sa_74d03211585eb6c3e1f91ceb",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US07265149B2;0295;804629\",\"rsmi\":\"Cl[Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([CH3:6])[CH3:7].[OH:8][c:9]1[cH:10][cH:11][c:12]2[nH:13][cH:14][cH:15][c:16]2[cH:17]1>CCOCC.CN(C)C=O.c1c[nH]cn1>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][c:9]1[cH:10][cH:11][c:12]2[nH:13][cH:14][cH:15][c:16]2[cH:17]1\"},\"mapped_reaction_smiles\":\"Cl[Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([CH3:6])[CH3:7].[OH:8][c:9]1[cH:10][cH:11][c:12]2[nH:13][cH:14][cH:15][c:16]2[cH:17]1>CCOCC.CN(C)C=O.c1c[nH]cn1>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][c:9]1[cH:10][cH:11][c:12]2[nH:13][cH:14][cH:15][c:16]2[cH:17]1\"}",
"reactionStep": {
"id": "sa_74d03211585eb6c3e1f91ceb",
"reactionHash": "6c4594cf6e346d771c92f0d1895f12ff57a88268ed31b260377c94b31122b809"
},
"children": [
{
"id": "9657",
"routeId": "sa_ee21244c374dc044bda28ccd",
"moleculeId": "sa_1785e67b778eb91f7e04c15a",
"parentId": "9656",
"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": "9658",
"routeId": "sa_ee21244c374dc044bda28ccd",
"moleculeId": "sa_c16c034374c518bf97dd1add",
"parentId": "9656",
"isLeaf": true,
"molecule": {
"id": "sa_c16c034374c518bf97dd1add",
"inchikey": "LMIQERWZRIFWNZ-UHFFFAOYSA-N",
"smiles": "Oc1ccc2[nH]ccc2c1"
},
"smiles": "Oc1ccc2[nH]ccc2c1",
"reactionStepId": null,
"template": null,
"metadata": null,
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}
]
},
{
"id": "9659",
"routeId": "sa_ee21244c374dc044bda28ccd",
"moleculeId": "sa_6170bddd2f4a4137325c4a17",
"parentId": "9655",
"isLeaf": true,
"molecule": {
"id": "sa_6170bddd2f4a4137325c4a17",
"inchikey": "PQJJJMRNHATNKG-UHFFFAOYSA-N",
"smiles": "CCOC(=O)CBr"
},
"smiles": "CCOC(=O)CBr",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
},
{
"id": "9660",
"routeId": "sa_ee21244c374dc044bda28ccd",
"moleculeId": "sa_5ecd82ea67e7da7de70a3ca2",
"parentId": "9653",
"isLeaf": false,
"molecule": {
"id": "sa_5ecd82ea67e7da7de70a3ca2",
"inchikey": "NTZURVYETGDLFZ-UHFFFAOYSA-N",
"smiles": "Cn1nc(-c2ccc(OC(F)(F)F)cc2)cc1CO"
},
"smiles": "Cn1nc(-c2ccc(OC(F)(F)F)cc2)cc1CO",
"reactionStepId": "sa_1c1d1cf77de75c2b3d48b6ce",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US07265149B2;0289;804626\",\"rsmi\":\"CCO[C:18]([c:17]1[n:2]([CH3:1])[n:3][c:4](-[c:5]2[cH:6][cH:7][c:8]([O:9][C:10]([F:11])([F:12])[F:13])[cH:14][cH:15]2)[cH:16]1)=[O:19]>[Al+3].[HH].[HH].[HH].[HH].[Li+]>[CH3:1][n:2]1[n:3][c:4](-[c:5]2[cH:6][cH:7][c:8]([O:9][C:10]([F:11])([F:12])[F:13])[cH:14][cH:15]2)[cH:16][c:17]1[CH2:18][OH:19]\"},\"mapped_reaction_smiles\":\"CCO[C:18]([c:17]1[n:2]([CH3:1])[n:3][c:4](-[c:5]2[cH:6][cH:7][c:8]([O:9][C:10]([F:11])([F:12])[F:13])[cH:14][cH:15]2)[cH:16]1)=[O:19]>[Al+3].[HH].[HH].[HH].[HH].[Li+]>[CH3:1][n:2]1[n:3][c:4](-[c:5]2[cH:6][cH:7][c:8]([O:9][C:10]([F:11])([F:12])[F:13])[cH:14][cH:15]2)[cH:16][c:17]1[CH2:18][OH:19]\"}",
"reactionStep": {
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"reactionHash": "405435c36e7b7b6c78990d27c61c21ec3f5ce5cea17dc5a9c4b9ae6b9f65171e"
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"children": [
{
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"moleculeId": "sa_b9385edb64769d691418eb9a",
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"molecule": {
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"inchikey": "CEPZCXSBJCPSRQ-UHFFFAOYSA-N",
"smiles": "CCOC(=O)c1cc(-c2ccc(OC(F)(F)F)cc2)nn1C"
},
"smiles": "CCOC(=O)c1cc(-c2ccc(OC(F)(F)F)cc2)nn1C",
"reactionStepId": null,
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}
]
}
]
}
]
}
}