Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CC(C)c1nc(N2CCN(c3ncc(-c4ccc(-n5cnn(C)c5=O)c(F)c4)cc3C#N)CC2)no1
InChiKey
OIKAHVNLMHKREL-UHFFFAOYSA-N
Route Signature
70aec3f0e0c9c4c9028b407c0bf497b56d5aa2db526ebe5e683310f0b1f3fc46
Synthesis route with 4 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_2544b8aaa285ab13782bdadf",
"signature": "70aec3f0e0c9c4c9028b407c0bf497b56d5aa2db526ebe5e683310f0b1f3fc46",
"contentHash": "841b4a1041f9a706ebc1988dbdd9b1e7480f833c9c0c10f8007fa3d0c7e0d087",
"length": 4,
"isConvergent": true
},
"target": {
"id": "sa_85acd2520e0c12bc1e0ed8e0",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-02292",
"moleculeId": "sa_c458fde4348314946e2f5683",
"smiles": "CC(C)c1nc(N2CCN(c3ncc(-c4ccc(-n5cnn(C)c5=O)c(F)c4)cc3C#N)CC2)no1",
"routeLength": 4,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_c458fde4348314946e2f5683",
"inchikey": "OIKAHVNLMHKREL-UHFFFAOYSA-N",
"smiles": "CC(C)c1nc(N2CCN(c3ncc(-c4ccc(-n5cnn(C)c5=O)c(F)c4)cc3C#N)CC2)no1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "10683",
"routeId": "sa_2544b8aaa285ab13782bdadf",
"moleculeId": "sa_c458fde4348314946e2f5683",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_c458fde4348314946e2f5683",
"inchikey": "OIKAHVNLMHKREL-UHFFFAOYSA-N",
"smiles": "CC(C)c1nc(N2CCN(c3ncc(-c4ccc(-n5cnn(C)c5=O)c(F)c4)cc3C#N)CC2)no1"
},
"smiles": "CC(C)c1nc(N2CCN(c3ncc(-c4ccc(-n5cnn(C)c5=O)c(F)c4)cc3C#N)CC2)no1",
"reactionStepId": "sa_aacac2f212095030062318e3",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160068515A1;0400;1849959\",\"rsmi\":\"Br[c:17]1[cH:18][c:19]([F:20])[c:21](-[n:22]2[cH:23][n:24][n:25]([CH3:26])[c:27]2=[O:28])[cH:29][cH:30]1.CC1(C)OB([c:16]2[cH:15][c:12]([C:13]#[N:14])[c:11]([N:10]3[CH2:9][CH2:8][N:7]([c:6]4[n:5][c:4]([CH:2]([CH3:1])[CH3:3])[o:36][n:35]4)[CH2:34][CH2:33]3)[n:32][cH:31]2)OC1(C)C>CN(C)C=O.O=C(O)O.[Na+].[Na+].c1ccc([PH](c2ccccc2)(c2ccccc2)[Pd]([PH](c2ccccc2)(c2ccccc2)c2ccccc2)([PH](c2ccccc2)(c2ccccc2)c2ccccc2)[PH](c2ccccc2)(c2ccccc2)c2ccccc2)cc1>[CH3:1][CH:2]([CH3:3])[c:4]1[n:5][c:6]([N:7]2[CH2:8][CH2:9][N:10]([c:11]3[c:12]([C:13]#[N:14])[cH:15][c:16](-[c:17]4[cH:18][c:19]([F:20])[c:21](-[n:22]5[cH:23][n:24][n:25]([CH3:26])[c:27]5=[O:28])[cH:29][cH:30]4)[cH:31][n:32]3)[CH2:33][CH2:34]2)[n:35][o:36]1\"},\"mapped_reaction_smiles\":\"Br[c:17]1[cH:18][c:19]([F:20])[c:21](-[n:22]2[cH:23][n:24][n:25]([CH3:26])[c:27]2=[O:28])[cH:29][cH:30]1.CC1(C)OB([c:16]2[cH:15][c:12]([C:13]#[N:14])[c:11]([N:10]3[CH2:9][CH2:8][N:7]([c:6]4[n:5][c:4]([CH:2]([CH3:1])[CH3:3])[o:36][n:35]4)[CH2:34][CH2:33]3)[n:32][cH:31]2)OC1(C)C>CN(C)C=O.O=C(O)O.[Na+].[Na+].c1ccc([PH](c2ccccc2)(c2ccccc2)[Pd]([PH](c2ccccc2)(c2ccccc2)c2ccccc2)([PH](c2ccccc2)(c2ccccc2)c2ccccc2)[PH](c2ccccc2)(c2ccccc2)c2ccccc2)cc1>[CH3:1][CH:2]([CH3:3])[c:4]1[n:5][c:6]([N:7]2[CH2:8][CH2:9][N:10]([c:11]3[c:12]([C:13]#[N:14])[cH:15][c:16](-[c:17]4[cH:18][c:19]([F:20])[c:21](-[n:22]5[cH:23][n:24][n:25]([CH3:26])[c:27]5=[O:28])[cH:29][cH:30]4)[cH:31][n:32]3)[CH2:33][CH2:34]2)[n:35][o:36]1\"}",
"reactionStep": {
"id": "sa_aacac2f212095030062318e3",
"reactionHash": "cb463873669ce257651b5c612ebba9d4fd711a45d96290bd5a74b2c7ecf25afd"
},
"children": [
{
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"routeId": "sa_2544b8aaa285ab13782bdadf",
"moleculeId": "sa_ba61c54e85bf968519a5c550",
"parentId": "10683",
"isLeaf": false,
"molecule": {
"id": "sa_ba61c54e85bf968519a5c550",
"inchikey": "CUFYEMYEXSJQMT-UHFFFAOYSA-N",
"smiles": "CC(C)c1nc(N2CCN(c3ncc(B4OC(C)(C)C(C)(C)O4)cc3C#N)CC2)no1"
},
"smiles": "CC(C)c1nc(N2CCN(c3ncc(B4OC(C)(C)C(C)(C)O4)cc3C#N)CC2)no1",
"reactionStepId": "sa_f021b482c8f6f84a5a72bd00",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160068515A1;0398;1849958\",\"rsmi\":\"Br[c:16]1[cH:15][c:12]([C:13]#[N:14])[c:11]([N:10]2[CH2:9][CH2:8][N:7]([c:6]3[n:5][c:4]([CH:2]([CH3:1])[CH3:3])[o:31][n:30]3)[CH2:29][CH2:28]2)[n:27][cH:26]1.CC1(C)OB([B:17]2[O:18][C:19]([CH3:20])([CH3:21])[C:22]([CH3:23])([CH3:24])[O:25]2)OC1(C)C>C1COCCO1.CC(=O)O.Cl[Pd]Cl.[Fe+2].[Fe+2].[K+]>[CH3:1][CH:2]([CH3:3])[c:4]1[n:5][c:6]([N:7]2[CH2:8][CH2:9][N:10]([c:11]3[c:12]([C:13]#[N:14])[cH:15][c:16]([B:17]4[O:18][C:19]([CH3:20])([CH3:21])[C:22]([CH3:23])([CH3:24])[O:25]4)[cH:26][n:27]3)[CH2:28][CH2:29]2)[n:30][o:31]1\"},\"mapped_reaction_smiles\":\"Br[c:16]1[cH:15][c:12]([C:13]#[N:14])[c:11]([N:10]2[CH2:9][CH2:8][N:7]([c:6]3[n:5][c:4]([CH:2]([CH3:1])[CH3:3])[o:31][n:30]3)[CH2:29][CH2:28]2)[n:27][cH:26]1.CC1(C)OB([B:17]2[O:18][C:19]([CH3:20])([CH3:21])[C:22]([CH3:23])([CH3:24])[O:25]2)OC1(C)C>C1COCCO1.CC(=O)O.Cl[Pd]Cl.[Fe+2].[Fe+2].[K+]>[CH3:1][CH:2]([CH3:3])[c:4]1[n:5][c:6]([N:7]2[CH2:8][CH2:9][N:10]([c:11]3[c:12]([C:13]#[N:14])[cH:15][c:16]([B:17]4[O:18][C:19]([CH3:20])([CH3:21])[C:22]([CH3:23])([CH3:24])[O:25]4)[cH:26][n:27]3)[CH2:28][CH2:29]2)[n:30][o:31]1\"}",
"reactionStep": {
"id": "sa_f021b482c8f6f84a5a72bd00",
"reactionHash": "fcf791518fcae8b820d23e731303604a3cff6ff511020b0ddcec200247eb60d9"
},
"children": [
{
"id": "10685",
"routeId": "sa_2544b8aaa285ab13782bdadf",
"moleculeId": "sa_14f25843e3f0c8c6c9b27b01",
"parentId": "10684",
"isLeaf": false,
"molecule": {
"id": "sa_14f25843e3f0c8c6c9b27b01",
"inchikey": "GHGIGBZRKSWBKR-UHFFFAOYSA-N",
"smiles": "CC(C)c1nc(N2CCN(c3ncc(Br)cc3C#N)CC2)no1"
},
"smiles": "CC(C)c1nc(N2CCN(c3ncc(Br)cc3C#N)CC2)no1",
"reactionStepId": "sa_069112c1f05fe9a7e87e763c",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160068515A1;0396;1849957\",\"rsmi\":\"Cl[c:11]1[c:12]([C:13]#[N:14])[cH:15][c:16]([Br:17])[cH:18][n:19]1.[CH3:1][CH:2]([CH3:3])[c:4]1[n:5][c:6]([N:7]2[CH2:8][CH2:9][NH:10][CH2:20][CH2:21]2)[n:22][o:23]1>CN(C)C=O.Cc1ccccc1.O=C(O)O.[K+].[K+]>[CH3:1][CH:2]([CH3:3])[c:4]1[n:5][c:6]([N:7]2[CH2:8][CH2:9][N:10]([c:11]3[c:12]([C:13]#[N:14])[cH:15][c:16]([Br:17])[cH:18][n:19]3)[CH2:20][CH2:21]2)[n:22][o:23]1\"},\"mapped_reaction_smiles\":\"Cl[c:11]1[c:12]([C:13]#[N:14])[cH:15][c:16]([Br:17])[cH:18][n:19]1.[CH3:1][CH:2]([CH3:3])[c:4]1[n:5][c:6]([N:7]2[CH2:8][CH2:9][NH:10][CH2:20][CH2:21]2)[n:22][o:23]1>CN(C)C=O.Cc1ccccc1.O=C(O)O.[K+].[K+]>[CH3:1][CH:2]([CH3:3])[c:4]1[n:5][c:6]([N:7]2[CH2:8][CH2:9][N:10]([c:11]3[c:12]([C:13]#[N:14])[cH:15][c:16]([Br:17])[cH:18][n:19]3)[CH2:20][CH2:21]2)[n:22][o:23]1\"}",
"reactionStep": {
"id": "sa_069112c1f05fe9a7e87e763c",
"reactionHash": "0939ea9f0c7ec09e67087e2ae9aa725ff12fe8f798beae521cd4ce7cf5ec4650"
},
"children": [
{
"id": "10686",
"routeId": "sa_2544b8aaa285ab13782bdadf",
"moleculeId": "sa_d752b252aba43ffbefe807ac",
"parentId": "10685",
"isLeaf": false,
"molecule": {
"id": "sa_d752b252aba43ffbefe807ac",
"inchikey": "CKIXSYAXCGXRKU-UHFFFAOYSA-N",
"smiles": "CC(C)c1nc(N2CCNCC2)no1"
},
"smiles": "CC(C)c1nc(N2CCNCC2)no1",
"reactionStepId": "sa_98e1870e1bdbe2810593ee8f",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160068515A1;0394;1849956\",\"rsmi\":\"CC(C)(C)OC(=O)[N:10]1[CH2:9][CH2:8][N:7]([c:6]2[n:5][c:4]([CH:2]([CH3:1])[CH3:3])[o:14][n:13]2)[CH2:12][CH2:11]1>CCOC(C)=O.Cl>[CH3:1][CH:2]([CH3:3])[c:4]1[n:5][c:6]([N:7]2[CH2:8][CH2:9][NH:10][CH2:11][CH2:12]2)[n:13][o:14]1\"},\"mapped_reaction_smiles\":\"CC(C)(C)OC(=O)[N:10]1[CH2:9][CH2:8][N:7]([c:6]2[n:5][c:4]([CH:2]([CH3:1])[CH3:3])[o:14][n:13]2)[CH2:12][CH2:11]1>CCOC(C)=O.Cl>[CH3:1][CH:2]([CH3:3])[c:4]1[n:5][c:6]([N:7]2[CH2:8][CH2:9][NH:10][CH2:11][CH2:12]2)[n:13][o:14]1\"}",
"reactionStep": {
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"reactionHash": "f6768613912a1faaefbcf5498043acc576a8d0b5aa30a12b745bafb86407f097"
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"children": [
{
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"routeId": "sa_2544b8aaa285ab13782bdadf",
"moleculeId": "sa_414623b0d461e7562994c7c0",
"parentId": "10686",
"isLeaf": true,
"molecule": {
"id": "sa_414623b0d461e7562994c7c0",
"inchikey": "BZSQQOSFVOSWDQ-UHFFFAOYSA-N",
"smiles": "CC(C)c1nc(N2CCN(C(=O)OC(C)(C)C)CC2)no1"
},
"smiles": "CC(C)c1nc(N2CCN(C(=O)OC(C)(C)C)CC2)no1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "10688",
"routeId": "sa_2544b8aaa285ab13782bdadf",
"moleculeId": "sa_5ad634aaf463e9aebc885292",
"parentId": "10685",
"isLeaf": true,
"molecule": {
"id": "sa_5ad634aaf463e9aebc885292",
"inchikey": "MQOHJAYYYVQBSH-UHFFFAOYSA-N",
"smiles": "N#Cc1cc(Br)cnc1Cl"
},
"smiles": "N#Cc1cc(Br)cnc1Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "10689",
"routeId": "sa_2544b8aaa285ab13782bdadf",
"moleculeId": "sa_e6c301388ac142801d4af5a2",
"parentId": "10684",
"isLeaf": true,
"molecule": {
"id": "sa_e6c301388ac142801d4af5a2",
"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",
"reactionStepId": null,
"template": null,
"metadata": null,
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"children": []
}
]
},
{
"id": "10690",
"routeId": "sa_2544b8aaa285ab13782bdadf",
"moleculeId": "sa_89616acfe5f08917996053bf",
"parentId": "10683",
"isLeaf": false,
"molecule": {
"id": "sa_89616acfe5f08917996053bf",
"inchikey": "ZBMCLMMIXWGHHL-UHFFFAOYSA-N",
"smiles": "Cn1ncn(-c2ccc(Br)cc2F)c1=O"
},
"smiles": "Cn1ncn(-c2ccc(Br)cc2F)c1=O",
"reactionStepId": "sa_600eadef7696cc2468ff169e",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160068515A1;0169;1849904\",\"rsmi\":\"I[CH3:1].[nH:2]1[n:3][cH:4][n:5](-[c:6]2[c:7]([F:8])[cH:9][c:10]([Br:11])[cH:12][cH:13]2)[c:14]1=[O:15]>CN(C)C=O.[K+].O>[CH3:1][n:2]1[n:3][cH:4][n:5](-[c:6]2[c:7]([F:8])[cH:9][c:10]([Br:11])[cH:12][cH:13]2)[c:14]1=[O:15]\"},\"mapped_reaction_smiles\":\"I[CH3:1].[nH:2]1[n:3][cH:4][n:5](-[c:6]2[c:7]([F:8])[cH:9][c:10]([Br:11])[cH:12][cH:13]2)[c:14]1=[O:15]>CN(C)C=O.[K+].O>[CH3:1][n:2]1[n:3][cH:4][n:5](-[c:6]2[c:7]([F:8])[cH:9][c:10]([Br:11])[cH:12][cH:13]2)[c:14]1=[O:15]\"}",
"reactionStep": {
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"reactionHash": "1870b610060c37000eeb09739373fb203c1ed5313eed4a1627df00c6290f6ff3"
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"children": [
{
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"routeId": "sa_2544b8aaa285ab13782bdadf",
"moleculeId": "sa_82fdccf7d1cc329c9db73f21",
"parentId": "10690",
"isLeaf": true,
"molecule": {
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"inchikey": "INQOMBQAUSQDDS-UHFFFAOYSA-N",
"smiles": "CI"
},
"smiles": "CI",
"reactionStepId": null,
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},
{
"id": "10692",
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"molecule": {
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"inchikey": "ISKRRNZXRUNHQS-UHFFFAOYSA-N",
"smiles": "O=c1[nH]ncn1-c1ccc(Br)cc1F"
},
"smiles": "O=c1[nH]ncn1-c1ccc(Br)cc1F",
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}
]
}
]
}
}