Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
c1cc2c(ccn2CC2CCNC2)cc1-c1cnn(C2CCCCO2)c1
InChiKey
CGYCYLDUYHIMNR-UHFFFAOYSA-N
Route Signature
12587f9d65e9519f302843c11e765b69052f8fe328143daa8881359b240ef264
Synthesis route with 4 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_b63a00ed76b464a8c4cf9932",
"signature": "12587f9d65e9519f302843c11e765b69052f8fe328143daa8881359b240ef264",
"contentHash": "999dc2bcf24104e3df9d954ea94a466df70bb0e7163c4d8d6c7796ef7c25ab5e",
"length": 4,
"isConvergent": true
},
"target": {
"id": "sa_3960db1804a96a2d326eaa90",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-03895",
"moleculeId": "sa_2c518cacbd47284c20658516",
"smiles": "c1cc2c(ccn2CC2CCNC2)cc1-c1cnn(C2CCCCO2)c1",
"routeLength": 4,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_2c518cacbd47284c20658516",
"inchikey": "CGYCYLDUYHIMNR-UHFFFAOYSA-N",
"smiles": "c1cc2c(ccn2CC2CCNC2)cc1-c1cnn(C2CCCCO2)c1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "2390",
"routeId": "sa_b63a00ed76b464a8c4cf9932",
"moleculeId": "sa_2c518cacbd47284c20658516",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_2c518cacbd47284c20658516",
"inchikey": "CGYCYLDUYHIMNR-UHFFFAOYSA-N",
"smiles": "c1cc2c(ccn2CC2CCNC2)cc1-c1cnn(C2CCCCO2)c1"
},
"smiles": "c1cc2c(ccn2CC2CCNC2)cc1-c1cnn(C2CCCCO2)c1",
"reactionStepId": "sa_74acf747d6d18edb70b17927",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160024056A1;0206;1827111\",\"rsmi\":\"O=C(OCc1ccccc1)[N:8]1[CH2:7][CH2:6][CH:5]([CH2:4][n:3]2[cH:2][cH:1][c:26]3[c:10]2[cH:11][cH:12][c:13](-[c:14]2[cH:15][n:16]([CH:17]4[CH2:18][CH2:19][CH2:20][CH2:21][O:22]4)[n:23][cH:24]2)[cH:25]3)[CH2:9]1>CCO.CO.ClCCl.[Pd]>[cH:1]1[cH:2][n:3]([CH2:4][CH:5]2[CH2:6][CH2:7][NH:8][CH2:9]2)[c:10]2[cH:11][cH:12][c:13](-[c:14]3[cH:15][n:16]([CH:17]4[CH2:18][CH2:19][CH2:20][CH2:21][O:22]4)[n:23][cH:24]3)[cH:25][c:26]12\"},\"mapped_reaction_smiles\":\"O=C(OCc1ccccc1)[N:8]1[CH2:7][CH2:6][CH:5]([CH2:4][n:3]2[cH:2][cH:1][c:26]3[c:10]2[cH:11][cH:12][c:13](-[c:14]2[cH:15][n:16]([CH:17]4[CH2:18][CH2:19][CH2:20][CH2:21][O:22]4)[n:23][cH:24]2)[cH:25]3)[CH2:9]1>CCO.CO.ClCCl.[Pd]>[cH:1]1[cH:2][n:3]([CH2:4][CH:5]2[CH2:6][CH2:7][NH:8][CH2:9]2)[c:10]2[cH:11][cH:12][c:13](-[c:14]3[cH:15][n:16]([CH:17]4[CH2:18][CH2:19][CH2:20][CH2:21][O:22]4)[n:23][cH:24]3)[cH:25][c:26]12\"}",
"reactionStep": {
"id": "sa_74acf747d6d18edb70b17927",
"reactionHash": "0bd72afc1214ee650b401f2822cf7312609dcb202de4a914bc647e55be7512d1"
},
"children": [
{
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"routeId": "sa_b63a00ed76b464a8c4cf9932",
"moleculeId": "sa_f858002746daa25878b7b4d1",
"parentId": "2390",
"isLeaf": false,
"molecule": {
"id": "sa_f858002746daa25878b7b4d1",
"inchikey": "GCDCWIIIUHXVOW-UHFFFAOYSA-N",
"smiles": "O=C(OCc1ccccc1)N1CCC(Cn2ccc3cc(-c4cnn(C5CCCCO5)c4)ccc32)C1"
},
"smiles": "O=C(OCc1ccccc1)N1CCC(Cn2ccc3cc(-c4cnn(C5CCCCO5)c4)ccc32)C1",
"reactionStepId": "sa_50f01c5fb1b30ab719cb56ff",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160024056A1;0205;1827110\",\"rsmi\":\"Br[c:21]1[cH:20][c:19]2[cH:18][cH:17][n:16]([CH2:15][CH:14]3[CH2:13][CH2:12][N:11]([C:2](=[O:1])[O:3][CH2:4][c:5]4[cH:6][cH:7][cH:8][cH:9][cH:10]4)[CH2:36]3)[c:35]2[cH:34][cH:33]1.CC1(C)OB([c:22]2[cH:23][n:24]([CH:25]3[CH2:26][CH2:27][CH2:28][CH2:29][O:30]3)[n:31][cH:32]2)OC1(C)C>CN(C)C=O.O.O=C(O)O.[Cs+].[Cs+]>[O:1]=[C:2]([O:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[N:11]1[CH2:12][CH2:13][CH:14]([CH2:15][n:16]2[cH:17][cH:18][c:19]3[cH:20][c:21](-[c:22]4[cH:23][n:24]([CH:25]5[CH2:26][CH2:27][CH2:28][CH2:29][O:30]5)[n:31][cH:32]4)[cH:33][cH:34][c:35]23)[CH2:36]1\"},\"mapped_reaction_smiles\":\"Br[c:21]1[cH:20][c:19]2[cH:18][cH:17][n:16]([CH2:15][CH:14]3[CH2:13][CH2:12][N:11]([C:2](=[O:1])[O:3][CH2:4][c:5]4[cH:6][cH:7][cH:8][cH:9][cH:10]4)[CH2:36]3)[c:35]2[cH:34][cH:33]1.CC1(C)OB([c:22]2[cH:23][n:24]([CH:25]3[CH2:26][CH2:27][CH2:28][CH2:29][O:30]3)[n:31][cH:32]2)OC1(C)C>CN(C)C=O.O.O=C(O)O.[Cs+].[Cs+]>[O:1]=[C:2]([O:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[N:11]1[CH2:12][CH2:13][CH:14]([CH2:15][n:16]2[cH:17][cH:18][c:19]3[cH:20][c:21](-[c:22]4[cH:23][n:24]([CH:25]5[CH2:26][CH2:27][CH2:28][CH2:29][O:30]5)[n:31][cH:32]4)[cH:33][cH:34][c:35]23)[CH2:36]1\"}",
"reactionStep": {
"id": "sa_50f01c5fb1b30ab719cb56ff",
"reactionHash": "9364aa93c6c3b0feabd6b2c62c81da49f911e000aaff326b43a477c242ddf5e6"
},
"children": [
{
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"routeId": "sa_b63a00ed76b464a8c4cf9932",
"moleculeId": "sa_e107e3728e121c66e3a5f2a0",
"parentId": "2391",
"isLeaf": false,
"molecule": {
"id": "sa_e107e3728e121c66e3a5f2a0",
"inchikey": "WOZSUJSXPSWURP-UHFFFAOYSA-N",
"smiles": "O=C(OCc1ccccc1)N1CCC(Cn2ccc3cc(Br)ccc32)C1"
},
"smiles": "O=C(OCc1ccccc1)N1CCC(Cn2ccc3cc(Br)ccc32)C1",
"reactionStepId": "sa_f388ac051a91df082ba270eb",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160024056A1;0204;1827109\",\"rsmi\":\"Cc1ccc(S(=O)(=O)O[CH2:15][CH:14]2[CH2:13][CH2:12][N:11]([C:2](=[O:1])[O:3][CH2:4][c:5]3[cH:6][cH:7][cH:8][cH:9][cH:10]3)[CH2:26]2)cc1.[nH:16]1[cH:17][cH:18][c:19]2[cH:20][c:21]([Br:22])[cH:23][cH:24][c:25]12>CCCCCC.CCOC(C)=O.CN(C)C=O.[HH].[Na+]>[O:1]=[C:2]([O:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[N:11]1[CH2:12][CH2:13][CH:14]([CH2:15][n:16]2[cH:17][cH:18][c:19]3[cH:20][c:21]([Br:22])[cH:23][cH:24][c:25]23)[CH2:26]1\"},\"mapped_reaction_smiles\":\"Cc1ccc(S(=O)(=O)O[CH2:15][CH:14]2[CH2:13][CH2:12][N:11]([C:2](=[O:1])[O:3][CH2:4][c:5]3[cH:6][cH:7][cH:8][cH:9][cH:10]3)[CH2:26]2)cc1.[nH:16]1[cH:17][cH:18][c:19]2[cH:20][c:21]([Br:22])[cH:23][cH:24][c:25]12>CCCCCC.CCOC(C)=O.CN(C)C=O.[HH].[Na+]>[O:1]=[C:2]([O:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[N:11]1[CH2:12][CH2:13][CH:14]([CH2:15][n:16]2[cH:17][cH:18][c:19]3[cH:20][c:21]([Br:22])[cH:23][cH:24][c:25]23)[CH2:26]1\"}",
"reactionStep": {
"id": "sa_f388ac051a91df082ba270eb",
"reactionHash": "d4ee77a4cd0bcb708497a9a22a2590a07db0d3dff62c0120cc69fb1a10660710"
},
"children": [
{
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"routeId": "sa_b63a00ed76b464a8c4cf9932",
"moleculeId": "sa_1957b56dfb9bbfd0a5cebe98",
"parentId": "2392",
"isLeaf": false,
"molecule": {
"id": "sa_1957b56dfb9bbfd0a5cebe98",
"inchikey": "DDLVDGGKOSCIHY-UHFFFAOYSA-N",
"smiles": "Cc1ccc(S(=O)(=O)OCC2CCN(C(=O)OCc3ccccc3)C2)cc1"
},
"smiles": "Cc1ccc(S(=O)(=O)OCC2CCN(C(=O)OCc3ccccc3)C2)cc1",
"reactionStepId": "sa_ab549c0e91180f43a440fd4e",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160024056A1;0203;1827108\",\"rsmi\":\"Cl[S:6]([c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:27][cH:26]1)(=[O:7])=[O:8].[OH:9][CH2:10][CH:11]1[CH2:12][CH2:13][N:14]([C:15](=[O:16])[O:17][CH2:18][c:19]2[cH:20][cH:21][cH:22][cH:23][cH:24]2)[CH2:25]1>CCCCCC.CCN(CC)CC.CCOC(C)=O.ClCCl.O>[CH3:1][c:2]1[cH:3][cH:4][c:5]([S:6](=[O:7])(=[O:8])[O:9][CH2:10][CH:11]2[CH2:12][CH2:13][N:14]([C:15](=[O:16])[O:17][CH2:18][c:19]3[cH:20][cH:21][cH:22][cH:23][cH:24]3)[CH2:25]2)[cH:26][cH:27]1\"},\"mapped_reaction_smiles\":\"Cl[S:6]([c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:27][cH:26]1)(=[O:7])=[O:8].[OH:9][CH2:10][CH:11]1[CH2:12][CH2:13][N:14]([C:15](=[O:16])[O:17][CH2:18][c:19]2[cH:20][cH:21][cH:22][cH:23][cH:24]2)[CH2:25]1>CCCCCC.CCN(CC)CC.CCOC(C)=O.ClCCl.O>[CH3:1][c:2]1[cH:3][cH:4][c:5]([S:6](=[O:7])(=[O:8])[O:9][CH2:10][CH:11]2[CH2:12][CH2:13][N:14]([C:15](=[O:16])[O:17][CH2:18][c:19]3[cH:20][cH:21][cH:22][cH:23][cH:24]3)[CH2:25]2)[cH:26][cH:27]1\"}",
"reactionStep": {
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"reactionHash": "c9c8996b6240963f1cb1a52e6fb73747bade6ec734b1288b3e330fbd22982d58"
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"children": [
{
"id": "2394",
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"moleculeId": "sa_28189ad2d33238c7f987ecf5",
"parentId": "2393",
"isLeaf": true,
"molecule": {
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"inchikey": "YYROPELSRYBVMQ-UHFFFAOYSA-N",
"smiles": "Cc1ccc(S(=O)(=O)Cl)cc1"
},
"smiles": "Cc1ccc(S(=O)(=O)Cl)cc1",
"reactionStepId": null,
"template": null,
"metadata": null,
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},
{
"id": "2395",
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"parentId": "2393",
"isLeaf": true,
"molecule": {
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"inchikey": "ZRMWRJLLAVAFQP-UHFFFAOYSA-N",
"smiles": "O=C(OCc1ccccc1)N1CCC(CO)C1"
},
"smiles": "O=C(OCc1ccccc1)N1CCC(CO)C1",
"reactionStepId": null,
"template": null,
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}
]
},
{
"id": "2396",
"routeId": "sa_b63a00ed76b464a8c4cf9932",
"moleculeId": "sa_0cbec097cba36e9b1b751fc9",
"parentId": "2392",
"isLeaf": true,
"molecule": {
"id": "sa_0cbec097cba36e9b1b751fc9",
"inchikey": "VXWVFZFZYXOBTA-UHFFFAOYSA-N",
"smiles": "Brc1ccc2[nH]ccc2c1"
},
"smiles": "Brc1ccc2[nH]ccc2c1",
"reactionStepId": null,
"template": null,
"metadata": null,
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}
]
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{
"id": "2397",
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"molecule": {
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"inchikey": "YYSLAWXDXHVRHU-UHFFFAOYSA-N",
"smiles": "CC1(C)OB(c2cnn(C3CCCCO3)c2)OC1(C)C"
},
"smiles": "CC1(C)OB(c2cnn(C3CCCCO3)c2)OC1(C)C",
"reactionStepId": "sa_74039a47db847a40476a637e",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160024056A1;0201;1827107\",\"rsmi\":\"Br[c:6]1[cH:7][n:8]([CH:9]2[CH2:10][CH2:11][CH2:12][CH2:13][O:14]2)[n:15][cH:16]1.CC1(C)OB([B:5]2[O:4][C:2]([CH3:1])([CH3:3])[C:18]([CH3:19])([CH3:20])[O:17]2)OC1(C)C>C1COCCO1.CC(=O)O.ClCCl.Cl[Pd]Cl.[Fe+2].[K+]>[CH3:1][C:2]1([CH3:3])[O:4][B:5]([c:6]2[cH:7][n:8]([CH:9]3[CH2:10][CH2:11][CH2:12][CH2:13][O:14]3)[n:15][cH:16]2)[O:17][C:18]1([CH3:19])[CH3:20]\"},\"mapped_reaction_smiles\":\"Br[c:6]1[cH:7][n:8]([CH:9]2[CH2:10][CH2:11][CH2:12][CH2:13][O:14]2)[n:15][cH:16]1.CC1(C)OB([B:5]2[O:4][C:2]([CH3:1])([CH3:3])[C:18]([CH3:19])([CH3:20])[O:17]2)OC1(C)C>C1COCCO1.CC(=O)O.ClCCl.Cl[Pd]Cl.[Fe+2].[K+]>[CH3:1][C:2]1([CH3:3])[O:4][B:5]([c:6]2[cH:7][n:8]([CH:9]3[CH2:10][CH2:11][CH2:12][CH2:13][O:14]3)[n:15][cH:16]2)[O:17][C:18]1([CH3:19])[CH3:20]\"}",
"reactionStep": {
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"children": [
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"smiles": "Brc1cnn(C2CCCCO2)c1",
"reactionStepId": "sa_c0fd498f1ea79d0701a2c110",
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"metadata": "{\"annotations\":{\"ID\":\"US20160024056A1;0200;1827106\",\"rsmi\":\"[Br:1][c:2]1[cH:3][nH:4][n:11][cH:12]1.[CH:5]1=[CH:6][CH2:7][CH2:8][CH2:9][O:10]1>CCCCCC.CCOC(C)=O.CCOC(C)=O.O=C(O)C(F)(F)F>[Br:1][c:2]1[cH:3][n:4]([CH:5]2[CH2:6][CH2:7][CH2:8][CH2:9][O:10]2)[n:11][cH:12]1\"},\"mapped_reaction_smiles\":\"[Br:1][c:2]1[cH:3][nH:4][n:11][cH:12]1.[CH:5]1=[CH:6][CH2:7][CH2:8][CH2:9][O:10]1>CCCCCC.CCOC(C)=O.CCOC(C)=O.O=C(O)C(F)(F)F>[Br:1][c:2]1[cH:3][n:4]([CH:5]2[CH2:6][CH2:7][CH2:8][CH2:9][O:10]2)[n:11][cH:12]1\"}",
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"children": [
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{
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"molecule": {
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"smiles": "Brc1cn[nH]c1"
},
"smiles": "Brc1cn[nH]c1",
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}
]
},
{
"id": "2401",
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"molecule": {
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"inchikey": "IPWKHHSGDUIRAH-UHFFFAOYSA-N",
"smiles": "CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C"
},
"smiles": "CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C",
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]
}
]
}
}