Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CS(=O)(=O)N1CCC(Nc2c(NC(=O)CC3CCCC3)cnc3c2ccn3S(=O)(=O)c2ccccc2)CC1
InChiKey
CYEGZCRAMAXPSZ-UHFFFAOYSA-N
Route Signature
344fc45f171a0fc1baeddf8edf215f750c83b7f048164d4d29516fb46bacc7be
Synthesis route with 5 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_bfcfd4093ba573e3fa9d1fec",
"signature": "344fc45f171a0fc1baeddf8edf215f750c83b7f048164d4d29516fb46bacc7be",
"contentHash": "7076da370101af6283d188e3b1307fcd3d7b01ba7c66759bd8d3bc1762772a5e",
"length": 5,
"isConvergent": false
},
"target": {
"id": "sa_ed13b8e5d0a60a98e0b58fe4",
"benchmarkSetId": "61e696668b63e77d7c2a29c0821768e1c383de8313852d6e995224859494442e",
"targetId": "n5-02874",
"moleculeId": "sa_82e5b250877ce43011b2c724",
"smiles": "CS(=O)(=O)N1CCC(Nc2c(NC(=O)CC3CCCC3)cnc3c2ccn3S(=O)(=O)c2ccccc2)CC1",
"routeLength": 5,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_82e5b250877ce43011b2c724",
"inchikey": "CYEGZCRAMAXPSZ-UHFFFAOYSA-N",
"smiles": "CS(=O)(=O)N1CCC(Nc2c(NC(=O)CC3CCCC3)cnc3c2ccn3S(=O)(=O)c2ccccc2)CC1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "6508",
"routeId": "sa_bfcfd4093ba573e3fa9d1fec",
"moleculeId": "sa_82e5b250877ce43011b2c724",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_82e5b250877ce43011b2c724",
"inchikey": "CYEGZCRAMAXPSZ-UHFFFAOYSA-N",
"smiles": "CS(=O)(=O)N1CCC(Nc2c(NC(=O)CC3CCCC3)cnc3c2ccn3S(=O)(=O)c2ccccc2)CC1"
},
"smiles": "CS(=O)(=O)N1CCC(Nc2c(NC(=O)CC3CCCC3)cnc3c2ccn3S(=O)(=O)c2ccccc2)CC1",
"reactionStepId": "sa_6f91328cc209475c294f8047",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20110201593A1;0644;1094243\",\"rsmi\":\"Cl[S:2]([CH3:1])(=[O:3])=[O:4].[NH:5]1[CH2:6][CH2:7][CH:8]([NH:9][c:10]2[c:11]3[cH:12][cH:13][n:14]([S:15](=[O:16])(=[O:17])[c:18]4[cH:19][cH:20][cH:21][cH:22][cH:23]4)[c:24]3[n:25][cH:26][c:27]2[NH:28][C:29](=[O:30])[CH2:31][CH:32]2[CH2:33][CH2:34][CH2:35][CH2:36]2)[CH2:37][CH2:38]1>CCN(C(C)C)C(C)C.ClCCl>[CH3:1][S:2](=[O:3])(=[O:4])[N:5]1[CH2:6][CH2:7][CH:8]([NH:9][c:10]2[c:11]3[cH:12][cH:13][n:14]([S:15](=[O:16])(=[O:17])[c:18]4[cH:19][cH:20][cH:21][cH:22][cH:23]4)[c:24]3[n:25][cH:26][c:27]2[NH:28][C:29](=[O:30])[CH2:31][CH:32]2[CH2:33][CH2:34][CH2:35][CH2:36]2)[CH2:37][CH2:38]1\"},\"mapped_reaction_smiles\":\"Cl[S:2]([CH3:1])(=[O:3])=[O:4].[NH:5]1[CH2:6][CH2:7][CH:8]([NH:9][c:10]2[c:11]3[cH:12][cH:13][n:14]([S:15](=[O:16])(=[O:17])[c:18]4[cH:19][cH:20][cH:21][cH:22][cH:23]4)[c:24]3[n:25][cH:26][c:27]2[NH:28][C:29](=[O:30])[CH2:31][CH:32]2[CH2:33][CH2:34][CH2:35][CH2:36]2)[CH2:37][CH2:38]1>CCN(C(C)C)C(C)C.ClCCl>[CH3:1][S:2](=[O:3])(=[O:4])[N:5]1[CH2:6][CH2:7][CH:8]([NH:9][c:10]2[c:11]3[cH:12][cH:13][n:14]([S:15](=[O:16])(=[O:17])[c:18]4[cH:19][cH:20][cH:21][cH:22][cH:23]4)[c:24]3[n:25][cH:26][c:27]2[NH:28][C:29](=[O:30])[CH2:31][CH:32]2[CH2:33][CH2:34][CH2:35][CH2:36]2)[CH2:37][CH2:38]1\"}",
"reactionStep": {
"id": "sa_6f91328cc209475c294f8047",
"reactionHash": "c37f3d09c2ccc9acb87788521471b2bb5011f0b6f364504b5dc2c50e826c1001"
},
"children": [
{
"id": "6509",
"routeId": "sa_bfcfd4093ba573e3fa9d1fec",
"moleculeId": "sa_d2a31ea58046b00856f61ca5",
"parentId": "6508",
"isLeaf": true,
"molecule": {
"id": "sa_d2a31ea58046b00856f61ca5",
"inchikey": "QARBMVPHQWIHKH-UHFFFAOYSA-N",
"smiles": "CS(=O)(=O)Cl"
},
"smiles": "CS(=O)(=O)Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "6510",
"routeId": "sa_bfcfd4093ba573e3fa9d1fec",
"moleculeId": "sa_b5b2515aafb36695eb3dde8f",
"parentId": "6508",
"isLeaf": false,
"molecule": {
"id": "sa_b5b2515aafb36695eb3dde8f",
"inchikey": "UTWYXTKIYCIUBI-UHFFFAOYSA-N",
"smiles": "O=C(CC1CCCC1)Nc1cnc2c(ccn2S(=O)(=O)c2ccccc2)c1NC1CCNCC1"
},
"smiles": "O=C(CC1CCCC1)Nc1cnc2c(ccn2S(=O)(=O)c2ccccc2)c1NC1CCNCC1",
"reactionStepId": "sa_4a88b6493bd69d038231ab98",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20110201593A1;0643;1094242\",\"rsmi\":\"CC(C)(C)OC(=O)[N:20]1[CH2:19][CH2:18][CH:17]([NH:16][c:15]2[c:10]([NH:9][C:2](=[O:1])[CH2:3][CH:4]3[CH2:5][CH2:6][CH2:7][CH2:8]3)[cH:11][n:12][c:13]3[c:14]2[cH:23][cH:24][n:25]3[S:26](=[O:27])(=[O:28])[c:29]2[cH:30][cH:31][cH:32][cH:33][cH:34]2)[CH2:22][CH2:21]1>C1COCCO1.Cl>[O:1]=[C:2]([CH2:3][CH:4]1[CH2:5][CH2:6][CH2:7][CH2:8]1)[NH:9][c:10]1[cH:11][n:12][c:13]2[c:14]([c:15]1[NH:16][CH:17]1[CH2:18][CH2:19][NH:20][CH2:21][CH2:22]1)[cH:23][cH:24][n:25]2[S:26](=[O:27])(=[O:28])[c:29]1[cH:30][cH:31][cH:32][cH:33][cH:34]1\"},\"mapped_reaction_smiles\":\"CC(C)(C)OC(=O)[N:20]1[CH2:19][CH2:18][CH:17]([NH:16][c:15]2[c:10]([NH:9][C:2](=[O:1])[CH2:3][CH:4]3[CH2:5][CH2:6][CH2:7][CH2:8]3)[cH:11][n:12][c:13]3[c:14]2[cH:23][cH:24][n:25]3[S:26](=[O:27])(=[O:28])[c:29]2[cH:30][cH:31][cH:32][cH:33][cH:34]2)[CH2:22][CH2:21]1>C1COCCO1.Cl>[O:1]=[C:2]([CH2:3][CH:4]1[CH2:5][CH2:6][CH2:7][CH2:8]1)[NH:9][c:10]1[cH:11][n:12][c:13]2[c:14]([c:15]1[NH:16][CH:17]1[CH2:18][CH2:19][NH:20][CH2:21][CH2:22]1)[cH:23][cH:24][n:25]2[S:26](=[O:27])(=[O:28])[c:29]1[cH:30][cH:31][cH:32][cH:33][cH:34]1\"}",
"reactionStep": {
"id": "sa_4a88b6493bd69d038231ab98",
"reactionHash": "fa85f2a8442df7df62b7f75e826e8b14d47d7a8436dc5d99ff978e7ebf84f801"
},
"children": [
{
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"routeId": "sa_bfcfd4093ba573e3fa9d1fec",
"moleculeId": "sa_f7b575a6d2555be2ea5529c2",
"parentId": "6510",
"isLeaf": false,
"molecule": {
"id": "sa_f7b575a6d2555be2ea5529c2",
"inchikey": "OKWBEOWYHOHVSV-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)N1CCC(Nc2c(NC(=O)CC3CCCC3)cnc3c2ccn3S(=O)(=O)c2ccccc2)CC1"
},
"smiles": "CC(C)(C)OC(=O)N1CCC(Nc2c(NC(=O)CC3CCCC3)cnc3c2ccn3S(=O)(=O)c2ccccc2)CC1",
"reactionStepId": "sa_1988ff954147848cad91abb0",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20110201593A1;0642;1094241\",\"rsmi\":\"O[C:32](=[O:33])[CH2:34][CH:35]1[CH2:36][CH2:37][CH2:38][CH2:39]1.[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH:11]([NH:12][c:13]2[c:14]3[cH:15][cH:16][n:17]([S:18](=[O:19])(=[O:20])[c:21]4[cH:22][cH:23][cH:24][cH:25][cH:26]4)[c:27]3[n:28][cH:29][c:30]2[NH2:31])[CH2:40][CH2:41]1>CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C.Cl.ClCCl>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH:11]([NH:12][c:13]2[c:14]3[cH:15][cH:16][n:17]([S:18](=[O:19])(=[O:20])[c:21]4[cH:22][cH:23][cH:24][cH:25][cH:26]4)[c:27]3[n:28][cH:29][c:30]2[NH:31][C:32](=[O:33])[CH2:34][CH:35]2[CH2:36][CH2:37][CH2:38][CH2:39]2)[CH2:40][CH2:41]1\"},\"mapped_reaction_smiles\":\"O[C:32](=[O:33])[CH2:34][CH:35]1[CH2:36][CH2:37][CH2:38][CH2:39]1.[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH:11]([NH:12][c:13]2[c:14]3[cH:15][cH:16][n:17]([S:18](=[O:19])(=[O:20])[c:21]4[cH:22][cH:23][cH:24][cH:25][cH:26]4)[c:27]3[n:28][cH:29][c:30]2[NH2:31])[CH2:40][CH2:41]1>CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C.Cl.ClCCl>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH:11]([NH:12][c:13]2[c:14]3[cH:15][cH:16][n:17]([S:18](=[O:19])(=[O:20])[c:21]4[cH:22][cH:23][cH:24][cH:25][cH:26]4)[c:27]3[n:28][cH:29][c:30]2[NH:31][C:32](=[O:33])[CH2:34][CH:35]2[CH2:36][CH2:37][CH2:38][CH2:39]2)[CH2:40][CH2:41]1\"}",
"reactionStep": {
"id": "sa_1988ff954147848cad91abb0",
"reactionHash": "f51ea3b9ec0ed55596f28b48d61c86476625d9026331e49effe37b1594f67fbc"
},
"children": [
{
"id": "6512",
"routeId": "sa_bfcfd4093ba573e3fa9d1fec",
"moleculeId": "sa_0af8c13c86c649e0e846f189",
"parentId": "6511",
"isLeaf": false,
"molecule": {
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"inchikey": "PHXCVIISOOXUCP-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)N1CCC(Nc2c(N)cnc3c2ccn3S(=O)(=O)c2ccccc2)CC1"
},
"smiles": "CC(C)(C)OC(=O)N1CCC(Nc2c(N)cnc3c2ccn3S(=O)(=O)c2ccccc2)CC1",
"reactionStepId": "sa_3f97f294fedbafb4bfd9bd5e",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20110201593A1;0641;1094240\",\"rsmi\":\"O=[N+:31]([O-])[c:30]1[c:13]([NH:12][CH:11]2[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:33][CH2:32]2)[c:14]2[cH:15][cH:16][n:17]([S:18](=[O:19])(=[O:20])[c:21]3[cH:22][cH:23][cH:24][cH:25][cH:26]3)[c:27]2[n:28][cH:29]1>C1CCOC1.CCO.CCOCC.ClCCl.[Pd]>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH:11]([NH:12][c:13]2[c:14]3[cH:15][cH:16][n:17]([S:18](=[O:19])(=[O:20])[c:21]4[cH:22][cH:23][cH:24][cH:25][cH:26]4)[c:27]3[n:28][cH:29][c:30]2[NH2:31])[CH2:32][CH2:33]1\"},\"mapped_reaction_smiles\":\"O=[N+:31]([O-])[c:30]1[c:13]([NH:12][CH:11]2[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:33][CH2:32]2)[c:14]2[cH:15][cH:16][n:17]([S:18](=[O:19])(=[O:20])[c:21]3[cH:22][cH:23][cH:24][cH:25][cH:26]3)[c:27]2[n:28][cH:29]1>C1CCOC1.CCO.CCOCC.ClCCl.[Pd]>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH:11]([NH:12][c:13]2[c:14]3[cH:15][cH:16][n:17]([S:18](=[O:19])(=[O:20])[c:21]4[cH:22][cH:23][cH:24][cH:25][cH:26]4)[c:27]3[n:28][cH:29][c:30]2[NH2:31])[CH2:32][CH2:33]1\"}",
"reactionStep": {
"id": "sa_3f97f294fedbafb4bfd9bd5e",
"reactionHash": "b6ef8e2f0a258f51788f71e7f42564dde08807d5be055772b298db4165807ec4"
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"children": [
{
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"moleculeId": "sa_c6418fb9b3de50b5637123dd",
"parentId": "6512",
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"molecule": {
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"inchikey": "CNWYYGJRFAJFKI-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)N1CCC(Nc2c([N+](=O)[O-])cnc3c2ccn3S(=O)(=O)c2ccccc2)CC1"
},
"smiles": "CC(C)(C)OC(=O)N1CCC(Nc2c([N+](=O)[O-])cnc3c2ccn3S(=O)(=O)c2ccccc2)CC1",
"reactionStepId": "sa_696ba33b6750508f381a7aed",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20110201593A1;0640;1094239\",\"rsmi\":\"Cl[c:13]1[c:14]2[cH:15][cH:16][n:17]([S:18](=[O:19])(=[O:20])[c:21]3[cH:22][cH:23][cH:24][cH:25][cH:26]3)[c:27]2[n:28][cH:29][c:30]1[N+:31](=[O:32])[O-:33].[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH:11]([NH2:12])[CH2:34][CH2:35]1>CC(C)O.CCN(C(C)C)C(C)C>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH:11]([NH:12][c:13]2[c:14]3[cH:15][cH:16][n:17]([S:18](=[O:19])(=[O:20])[c:21]4[cH:22][cH:23][cH:24][cH:25][cH:26]4)[c:27]3[n:28][cH:29][c:30]2[N+:31](=[O:32])[O-:33])[CH2:34][CH2:35]1\"},\"mapped_reaction_smiles\":\"Cl[c:13]1[c:14]2[cH:15][cH:16][n:17]([S:18](=[O:19])(=[O:20])[c:21]3[cH:22][cH:23][cH:24][cH:25][cH:26]3)[c:27]2[n:28][cH:29][c:30]1[N+:31](=[O:32])[O-:33].[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH:11]([NH2:12])[CH2:34][CH2:35]1>CC(C)O.CCN(C(C)C)C(C)C>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH:11]([NH:12][c:13]2[c:14]3[cH:15][cH:16][n:17]([S:18](=[O:19])(=[O:20])[c:21]4[cH:22][cH:23][cH:24][cH:25][cH:26]4)[c:27]3[n:28][cH:29][c:30]2[N+:31](=[O:32])[O-:33])[CH2:34][CH2:35]1\"}",
"reactionStep": {
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"children": [
{
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"molecule": {
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"smiles": "CC(C)(C)OC(=O)N1CCC(N)CC1"
},
"smiles": "CC(C)(C)OC(=O)N1CCC(N)CC1",
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},
{
"id": "6515",
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"moleculeId": "sa_56cc0bcbabf9e490194312c1",
"parentId": "6513",
"isLeaf": true,
"molecule": {
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"inchikey": "VDNRYINHXTYMIT-UHFFFAOYSA-N",
"smiles": "O=[N+]([O-])c1cnc2c(ccn2S(=O)(=O)c2ccccc2)c1Cl"
},
"smiles": "O=[N+]([O-])c1cnc2c(ccn2S(=O)(=O)c2ccccc2)c1Cl",
"reactionStepId": null,
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}
]
}
]
},
{
"id": "6516",
"routeId": "sa_bfcfd4093ba573e3fa9d1fec",
"moleculeId": "sa_dc0461accb4bebf597231c75",
"parentId": "6511",
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"molecule": {
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"inchikey": "YVHAIVPPUIZFBA-UHFFFAOYSA-N",
"smiles": "O=C(O)CC1CCCC1"
},
"smiles": "O=C(O)CC1CCCC1",
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}
]
}
]
}
]
}
}