Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CC(C)Oc1ccc(-c2n[nH]cc2C=O)cc1Cl
InChiKey
UCIAQRAISFORIV-UHFFFAOYSA-N
Route Signature
9581da79cf626cd64f802288d7cbec5698d28a3e079739ea20082f2670b043fe
Synthesis route with 6 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_e88ee7814a56f035aa907b5d",
"signature": "9581da79cf626cd64f802288d7cbec5698d28a3e079739ea20082f2670b043fe",
"contentHash": "e00f8ca467c91231cc9e028b5212f56b7b297ce9b2a2e02718d9429f01ae0945",
"length": 6,
"isConvergent": false
},
"target": {
"id": "sa_39a410bfc04c14e8f7998a26",
"benchmarkSetId": "f925e688d731a0ad4e3aa6a505df094f6d3ca64ce3facc312bc5f64731921b33",
"targetId": "n5-00535",
"moleculeId": "sa_28b0e0c5fba50bff5c17ce29",
"smiles": "CC(C)Oc1ccc(-c2n[nH]cc2C=O)cc1Cl",
"routeLength": 6,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_28b0e0c5fba50bff5c17ce29",
"inchikey": "UCIAQRAISFORIV-UHFFFAOYSA-N",
"smiles": "CC(C)Oc1ccc(-c2n[nH]cc2C=O)cc1Cl"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 5
},
"rootNode": {
"id": "4447",
"routeId": "sa_e88ee7814a56f035aa907b5d",
"moleculeId": "sa_28b0e0c5fba50bff5c17ce29",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_28b0e0c5fba50bff5c17ce29",
"inchikey": "UCIAQRAISFORIV-UHFFFAOYSA-N",
"smiles": "CC(C)Oc1ccc(-c2n[nH]cc2C=O)cc1Cl"
},
"smiles": "CC(C)Oc1ccc(-c2n[nH]cc2C=O)cc1Cl",
"reactionStepId": "sa_fa599a5d7d1d5adc51f6a89b",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160137609A1;0285;1876459\",\"rsmi\":\"C1CCC([n:12]2[n:11][c:10](-[c:9]3[cH:8][c:6]([Cl:7])[c:5]([O:4][CH:2]([CH3:1])[CH3:3])[cH:18][cH:17]3)[c:14]([CH:15]=[O:16])[cH:13]2)OC1>Cl>[CH3:1][CH:2]([CH3:3])[O:4][c:5]1[c:6]([Cl:7])[cH:8][c:9](-[c:10]2[n:11][nH:12][cH:13][c:14]2[CH:15]=[O:16])[cH:17][cH:18]1\"},\"mapped_reaction_smiles\":\"C1CCC([n:12]2[n:11][c:10](-[c:9]3[cH:8][c:6]([Cl:7])[c:5]([O:4][CH:2]([CH3:1])[CH3:3])[cH:18][cH:17]3)[c:14]([CH:15]=[O:16])[cH:13]2)OC1>Cl>[CH3:1][CH:2]([CH3:3])[O:4][c:5]1[c:6]([Cl:7])[cH:8][c:9](-[c:10]2[n:11][nH:12][cH:13][c:14]2[CH:15]=[O:16])[cH:17][cH:18]1\"}",
"reactionStep": {
"id": "sa_fa599a5d7d1d5adc51f6a89b",
"reactionHash": "ff0261fc4feb8f56d1dbc498754a241008c01f297a93af0d85547eba44d2a019"
},
"children": [
{
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"routeId": "sa_e88ee7814a56f035aa907b5d",
"moleculeId": "sa_506ed89c2e111f0f9455a353",
"parentId": "4447",
"isLeaf": false,
"molecule": {
"id": "sa_506ed89c2e111f0f9455a353",
"inchikey": "IPJUEWNVHNPMKC-UHFFFAOYSA-N",
"smiles": "CC(C)Oc1ccc(-c2nn(C3CCCCO3)cc2C=O)cc1Cl"
},
"smiles": "CC(C)Oc1ccc(-c2nn(C3CCCCO3)cc2C=O)cc1Cl",
"reactionStepId": "sa_854d3ea9185e123d1dcc5e94",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160137609A1;0283;1876458\",\"rsmi\":\"I[c:10]1[n:11][n:12]([CH:13]2[CH2:14][CH2:15][CH2:16][CH2:17][O:18]2)[cH:19][c:20]1[CH:21]=[O:22].OB(O)[c:9]1[cH:8][c:6]([Cl:7])[c:5]([O:4][CH:2]([CH3:1])[CH3:3])[cH:24][cH:23]1>C1COCCO1.Cl[Pd]Cl.O.O=C(O)O.[Fe+2].[K+].[K+]>[CH3:1][CH:2]([CH3:3])[O:4][c:5]1[c:6]([Cl:7])[cH:8][c:9](-[c:10]2[n:11][n:12]([CH:13]3[CH2:14][CH2:15][CH2:16][CH2:17][O:18]3)[cH:19][c:20]2[CH:21]=[O:22])[cH:23][cH:24]1\"},\"mapped_reaction_smiles\":\"I[c:10]1[n:11][n:12]([CH:13]2[CH2:14][CH2:15][CH2:16][CH2:17][O:18]2)[cH:19][c:20]1[CH:21]=[O:22].OB(O)[c:9]1[cH:8][c:6]([Cl:7])[c:5]([O:4][CH:2]([CH3:1])[CH3:3])[cH:24][cH:23]1>C1COCCO1.Cl[Pd]Cl.O.O=C(O)O.[Fe+2].[K+].[K+]>[CH3:1][CH:2]([CH3:3])[O:4][c:5]1[c:6]([Cl:7])[cH:8][c:9](-[c:10]2[n:11][n:12]([CH:13]3[CH2:14][CH2:15][CH2:16][CH2:17][O:18]3)[cH:19][c:20]2[CH:21]=[O:22])[cH:23][cH:24]1\"}",
"reactionStep": {
"id": "sa_854d3ea9185e123d1dcc5e94",
"reactionHash": "933cd8cad6b2d6d1b9728a569f4a5e6b989a6a72a14c62cf1b3cb003bf73f801"
},
"children": [
{
"id": "4449",
"routeId": "sa_e88ee7814a56f035aa907b5d",
"moleculeId": "sa_ac49741dc7de64822f566714",
"parentId": "4448",
"isLeaf": true,
"molecule": {
"id": "sa_ac49741dc7de64822f566714",
"inchikey": "PJBWTULFEPFOEB-UHFFFAOYSA-N",
"smiles": "CC(C)Oc1ccc(B(O)O)cc1Cl"
},
"smiles": "CC(C)Oc1ccc(B(O)O)cc1Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "4450",
"routeId": "sa_e88ee7814a56f035aa907b5d",
"moleculeId": "sa_75441b040099c749d89a109b",
"parentId": "4448",
"isLeaf": false,
"molecule": {
"id": "sa_75441b040099c749d89a109b",
"inchikey": "TVGOFLFNBCDVFS-UHFFFAOYSA-N",
"smiles": "O=Cc1cn(C2CCCCO2)nc1I"
},
"smiles": "O=Cc1cn(C2CCCCO2)nc1I",
"reactionStepId": "sa_50fe4d623463255cbade4cbc",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160137609A1;0255;1876448\",\"rsmi\":\"[OH:1][CH2:2][c:3]1[cH:4][n:5]([CH:6]2[CH2:7][CH2:8][CH2:9][CH2:10][O:11]2)[n:12][c:13]1[I:14]>CCN(CC)CC.CS(C)=O.ClCCl.O=C(Cl)C(=O)Cl>[O:1]=[CH:2][c:3]1[cH:4][n:5]([CH:6]2[CH2:7][CH2:8][CH2:9][CH2:10][O:11]2)[n:12][c:13]1[I:14]\"},\"mapped_reaction_smiles\":\"[OH:1][CH2:2][c:3]1[cH:4][n:5]([CH:6]2[CH2:7][CH2:8][CH2:9][CH2:10][O:11]2)[n:12][c:13]1[I:14]>CCN(CC)CC.CS(C)=O.ClCCl.O=C(Cl)C(=O)Cl>[O:1]=[CH:2][c:3]1[cH:4][n:5]([CH:6]2[CH2:7][CH2:8][CH2:9][CH2:10][O:11]2)[n:12][c:13]1[I:14]\"}",
"reactionStep": {
"id": "sa_50fe4d623463255cbade4cbc",
"reactionHash": "933b6abb682a53e2a8684b2386d73bc9add434f306df434d2811677c8aabeac6"
},
"children": [
{
"id": "4451",
"routeId": "sa_e88ee7814a56f035aa907b5d",
"moleculeId": "sa_66dff4edaf703c519a2150ad",
"parentId": "4450",
"isLeaf": false,
"molecule": {
"id": "sa_66dff4edaf703c519a2150ad",
"inchikey": "YWVKKPWNNWIFGF-UHFFFAOYSA-N",
"smiles": "OCc1cn(C2CCCCO2)nc1I"
},
"smiles": "OCc1cn(C2CCCCO2)nc1I",
"reactionStepId": "sa_0aa15adad8f0887dda724795",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160137609A1;0253;1876447\",\"rsmi\":\"O[C:2](=[O:1])[c:3]1[cH:4][n:5]([CH:6]2[CH2:7][CH2:8][CH2:9][CH2:10][O:11]2)[n:12][c:13]1[I:14]>C1CCOC1>[OH:1][CH2:2][c:3]1[cH:4][n:5]([CH:6]2[CH2:7][CH2:8][CH2:9][CH2:10][O:11]2)[n:12][c:13]1[I:14]\"},\"mapped_reaction_smiles\":\"O[C:2](=[O:1])[c:3]1[cH:4][n:5]([CH:6]2[CH2:7][CH2:8][CH2:9][CH2:10][O:11]2)[n:12][c:13]1[I:14]>C1CCOC1>[OH:1][CH2:2][c:3]1[cH:4][n:5]([CH:6]2[CH2:7][CH2:8][CH2:9][CH2:10][O:11]2)[n:12][c:13]1[I:14]\"}",
"reactionStep": {
"id": "sa_0aa15adad8f0887dda724795",
"reactionHash": "fcb0304c14496fea397c07c78f399661c477bef9ed5f1e228a26e7339e49a52b"
},
"children": [
{
"id": "4452",
"routeId": "sa_e88ee7814a56f035aa907b5d",
"moleculeId": "sa_a962e29e4bc77a9f8ac635bf",
"parentId": "4451",
"isLeaf": false,
"molecule": {
"id": "sa_a962e29e4bc77a9f8ac635bf",
"inchikey": "BKPIZSKNOJQQDA-UHFFFAOYSA-N",
"smiles": "O=C(O)c1cn(C2CCCCO2)nc1I"
},
"smiles": "O=C(O)c1cn(C2CCCCO2)nc1I",
"reactionStepId": "sa_67332c1a23455838cfe06de4",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160137609A1;0251;1876446\",\"rsmi\":\"CC[O:3][C:2](=[O:1])[c:4]1[cH:5][n:6]([CH:7]2[CH2:8][CH2:9][CH2:10][CH2:11][O:12]2)[n:13][c:14]1[I:15]>C1CCOC1.CO.O.[Li+].O>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][n:6]([CH:7]2[CH2:8][CH2:9][CH2:10][CH2:11][O:12]2)[n:13][c:14]1[I:15]\"},\"mapped_reaction_smiles\":\"CC[O:3][C:2](=[O:1])[c:4]1[cH:5][n:6]([CH:7]2[CH2:8][CH2:9][CH2:10][CH2:11][O:12]2)[n:13][c:14]1[I:15]>C1CCOC1.CO.O.[Li+].O>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][n:6]([CH:7]2[CH2:8][CH2:9][CH2:10][CH2:11][O:12]2)[n:13][c:14]1[I:15]\"}",
"reactionStep": {
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"reactionHash": "2e7888fb2222bd80a6f0b721d252e2dbf6c98eff27e0ac7fa6f3c527a1d574cf"
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"children": [
{
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"routeId": "sa_e88ee7814a56f035aa907b5d",
"moleculeId": "sa_bd5aa622f0aa4c0de236f9b7",
"parentId": "4452",
"isLeaf": false,
"molecule": {
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"inchikey": "VURQQDXNTZYAMN-UHFFFAOYSA-N",
"smiles": "CCOC(=O)c1cn(C2CCCCO2)nc1I"
},
"smiles": "CCOC(=O)c1cn(C2CCCCO2)nc1I",
"reactionStepId": "sa_3f14070a14d079f17f0420c6",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160137609A1;0249;1876445\",\"rsmi\":\"[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][nH:8][n:15][c:16]1[I:17].[CH:9]1=[CH:10][CH2:11][CH2:12][CH2:13][O:14]1>C1CCOC1.Cc1ccc(S(=O)(=O)O)cc1>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8]([CH:9]2[CH2:10][CH2:11][CH2:12][CH2:13][O:14]2)[n:15][c:16]1[I:17]\"},\"mapped_reaction_smiles\":\"[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][nH:8][n:15][c:16]1[I:17].[CH:9]1=[CH:10][CH2:11][CH2:12][CH2:13][O:14]1>C1CCOC1.Cc1ccc(S(=O)(=O)O)cc1>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8]([CH:9]2[CH2:10][CH2:11][CH2:12][CH2:13][O:14]2)[n:15][c:16]1[I:17]\"}",
"reactionStep": {
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"reactionHash": "f0037680b67b149188aac3533ed460f828f4ba99d57576359c655a8851f02e4e"
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"children": [
{
"id": "4454",
"routeId": "sa_e88ee7814a56f035aa907b5d",
"moleculeId": "sa_359472b115a712c065ff6c19",
"parentId": "4453",
"isLeaf": true,
"molecule": {
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"inchikey": "BUDQDWGNQVEFAC-UHFFFAOYSA-N",
"smiles": "C1=COCCC1"
},
"smiles": "C1=COCCC1",
"reactionStepId": null,
"template": null,
"metadata": null,
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"children": []
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{
"id": "4455",
"routeId": "sa_e88ee7814a56f035aa907b5d",
"moleculeId": "sa_027882ca48812b8ba6c1b308",
"parentId": "4453",
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"molecule": {
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"inchikey": "GCZGLIKEVZAURZ-UHFFFAOYSA-N",
"smiles": "CCOC(=O)c1c[nH]nc1I"
},
"smiles": "CCOC(=O)c1c[nH]nc1I",
"reactionStepId": null,
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}
]
}
]
}
]
}
]
}
]
}
]
}
}