Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CCCCc1nc2c(N)nc3ccccc3c2n1CCCN(Cc1ccc(CC(=O)OC)cc1)C(=O)CS(C)(=O)=O
InChiKey
JESLMFCDDXPVAC-UHFFFAOYSA-N
Route Signature
a4ad7bf09d9df87cee53c852151c4fee2bb403810f2549ee91b4dd4436ef4287
Synthesis route with 9 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_73897196c71bed0d58d41710",
"signature": "a4ad7bf09d9df87cee53c852151c4fee2bb403810f2549ee91b4dd4436ef4287",
"contentHash": "538fb9e65550dc206edaac5336978751ba1e05b697d774ce0117118ebaed6b66",
"length": 9,
"isConvergent": false
},
"target": {
"id": "sa_22569af46f75c2f2d0d0d8cd",
"benchmarkSetId": "a82783729b577c36f2e09a2b6fdd55ae9542aed5546571d67ef9cb74dc21f70a",
"targetId": "n5-00016",
"moleculeId": "sa_107ca995a4d278df5cea4b4d",
"smiles": "CCCCc1nc2c(N)nc3ccccc3c2n1CCCN(Cc1ccc(CC(=O)OC)cc1)C(=O)CS(C)(=O)=O",
"routeLength": 9,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_107ca995a4d278df5cea4b4d",
"inchikey": "JESLMFCDDXPVAC-UHFFFAOYSA-N",
"smiles": "CCCCc1nc2c(N)nc3ccccc3c2n1CCCN(Cc1ccc(CC(=O)OC)cc1)C(=O)CS(C)(=O)=O"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "17334",
"routeId": "sa_73897196c71bed0d58d41710",
"moleculeId": "sa_107ca995a4d278df5cea4b4d",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_107ca995a4d278df5cea4b4d",
"inchikey": "JESLMFCDDXPVAC-UHFFFAOYSA-N",
"smiles": "CCCCc1nc2c(N)nc3ccccc3c2n1CCCN(Cc1ccc(CC(=O)OC)cc1)C(=O)CS(C)(=O)=O"
},
"smiles": "CCCCc1nc2c(N)nc3ccccc3c2n1CCCN(Cc1ccc(CC(=O)OC)cc1)C(=O)CS(C)(=O)=O",
"reactionStepId": "sa_dd832447a9f83cca8cc86be5",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130225555A1;0390;1413159\",\"rsmi\":\"O[C:35](=[O:36])[CH2:37][S:38]([CH3:39])(=[O:40])=[O:41].[CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([c:9]3[c:10]([cH:11][cH:12][cH:13][cH:14]3)[n:15][c:16]2[NH2:17])[n:18]1[CH2:19][CH2:20][CH2:21][NH:22][CH2:23][c:24]1[cH:25][cH:26][c:27]([CH2:28][C:29](=[O:30])[O:31][CH3:32])[cH:33][cH:34]1>CN(C)C(On1nnc2cccnc21)=[N+](C)C.ClCCl.F[PH](F)(F)(F)(F)F>[CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([c:9]3[c:10]([cH:11][cH:12][cH:13][cH:14]3)[n:15][c:16]2[NH2:17])[n:18]1[CH2:19][CH2:20][CH2:21][N:22]([CH2:23][c:24]1[cH:25][cH:26][c:27]([CH2:28][C:29](=[O:30])[O:31][CH3:32])[cH:33][cH:34]1)[C:35](=[O:36])[CH2:37][S:38]([CH3:39])(=[O:40])=[O:41]\"},\"mapped_reaction_smiles\":\"O[C:35](=[O:36])[CH2:37][S:38]([CH3:39])(=[O:40])=[O:41].[CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([c:9]3[c:10]([cH:11][cH:12][cH:13][cH:14]3)[n:15][c:16]2[NH2:17])[n:18]1[CH2:19][CH2:20][CH2:21][NH:22][CH2:23][c:24]1[cH:25][cH:26][c:27]([CH2:28][C:29](=[O:30])[O:31][CH3:32])[cH:33][cH:34]1>CN(C)C(On1nnc2cccnc21)=[N+](C)C.ClCCl.F[PH](F)(F)(F)(F)F>[CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([c:9]3[c:10]([cH:11][cH:12][cH:13][cH:14]3)[n:15][c:16]2[NH2:17])[n:18]1[CH2:19][CH2:20][CH2:21][N:22]([CH2:23][c:24]1[cH:25][cH:26][c:27]([CH2:28][C:29](=[O:30])[O:31][CH3:32])[cH:33][cH:34]1)[C:35](=[O:36])[CH2:37][S:38]([CH3:39])(=[O:40])=[O:41]\"}",
"reactionStep": {
"id": "sa_dd832447a9f83cca8cc86be5",
"reactionHash": "f8666fd8bf3537cb6797e0d2b1aab9dea649647f02cbc0bc980cd78d75109eef"
},
"children": [
{
"id": "17335",
"routeId": "sa_73897196c71bed0d58d41710",
"moleculeId": "sa_70c2e8b54bc804f29670d3b9",
"parentId": "17334",
"isLeaf": true,
"molecule": {
"id": "sa_70c2e8b54bc804f29670d3b9",
"inchikey": "NYEHUAQIJXERLP-UHFFFAOYSA-N",
"smiles": "CS(=O)(=O)CC(=O)O"
},
"smiles": "CS(=O)(=O)CC(=O)O",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "17336",
"routeId": "sa_73897196c71bed0d58d41710",
"moleculeId": "sa_7241d37477cac0d6353f6570",
"parentId": "17334",
"isLeaf": false,
"molecule": {
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"inchikey": "XIQQEASYCSFTBJ-UHFFFAOYSA-N",
"smiles": "CCCCc1nc2c(N)nc3ccccc3c2n1CCCNCc1ccc(CC(=O)OC)cc1"
},
"smiles": "CCCCc1nc2c(N)nc3ccccc3c2n1CCCNCc1ccc(CC(=O)OC)cc1",
"reactionStepId": "sa_eebe27400899c3a61419c2c6",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130225555A1;0286;1413136\",\"rsmi\":\"O=[CH:23][c:24]1[cH:25][cH:26][c:27]([CH2:28][C:29](=[O:30])[O:31][CH3:32])[cH:33][cH:34]1.[CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([c:9]3[c:10]([cH:11][cH:12][cH:13][cH:14]3)[n:15][c:16]2[NH2:17])[n:18]1[CH2:19][CH2:20][CH2:21][NH2:22]>C1CCOC1.CO.B.[Na+]>[CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([c:9]3[c:10]([cH:11][cH:12][cH:13][cH:14]3)[n:15][c:16]2[NH2:17])[n:18]1[CH2:19][CH2:20][CH2:21][NH:22][CH2:23][c:24]1[cH:25][cH:26][c:27]([CH2:28][C:29](=[O:30])[O:31][CH3:32])[cH:33][cH:34]1\"},\"mapped_reaction_smiles\":\"O=[CH:23][c:24]1[cH:25][cH:26][c:27]([CH2:28][C:29](=[O:30])[O:31][CH3:32])[cH:33][cH:34]1.[CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([c:9]3[c:10]([cH:11][cH:12][cH:13][cH:14]3)[n:15][c:16]2[NH2:17])[n:18]1[CH2:19][CH2:20][CH2:21][NH2:22]>C1CCOC1.CO.B.[Na+]>[CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([c:9]3[c:10]([cH:11][cH:12][cH:13][cH:14]3)[n:15][c:16]2[NH2:17])[n:18]1[CH2:19][CH2:20][CH2:21][NH:22][CH2:23][c:24]1[cH:25][cH:26][c:27]([CH2:28][C:29](=[O:30])[O:31][CH3:32])[cH:33][cH:34]1\"}",
"reactionStep": {
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"reactionHash": "fe1a40b4cb098ead6a394f69d64cc1069baa15b7b4ebddf83c6abd7f2dabd72b"
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"children": [
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"routeId": "sa_73897196c71bed0d58d41710",
"moleculeId": "sa_7adbb5fa15fca2e7370c0014",
"parentId": "17336",
"isLeaf": false,
"molecule": {
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"inchikey": "KRQJNCKJBILJJJ-UHFFFAOYSA-N",
"smiles": "CCCCc1nc2c(N)nc3ccccc3c2n1CCCN"
},
"smiles": "CCCCc1nc2c(N)nc3ccccc3c2n1CCCN",
"reactionStepId": "sa_e0a1d473190a36f8fbfd09c1",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130225555A1;0283;1413135\",\"rsmi\":\"CC(C)(C)OC(=O)[NH:22][CH2:21][CH2:20][CH2:19][n:18]1[c:5]([CH2:4][CH2:3][CH2:2][CH3:1])[n:6][c:7]2[c:8]1[c:9]1[c:10]([cH:11][cH:12][cH:13][cH:14]1)[n:15][c:16]2[NH2:17]>ClCCl.O=C(O)C(F)(F)F>[CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([c:9]3[c:10]([cH:11][cH:12][cH:13][cH:14]3)[n:15][c:16]2[NH2:17])[n:18]1[CH2:19][CH2:20][CH2:21][NH2:22]\"},\"mapped_reaction_smiles\":\"CC(C)(C)OC(=O)[NH:22][CH2:21][CH2:20][CH2:19][n:18]1[c:5]([CH2:4][CH2:3][CH2:2][CH3:1])[n:6][c:7]2[c:8]1[c:9]1[c:10]([cH:11][cH:12][cH:13][cH:14]1)[n:15][c:16]2[NH2:17]>ClCCl.O=C(O)C(F)(F)F>[CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([c:9]3[c:10]([cH:11][cH:12][cH:13][cH:14]3)[n:15][c:16]2[NH2:17])[n:18]1[CH2:19][CH2:20][CH2:21][NH2:22]\"}",
"reactionStep": {
"id": "sa_e0a1d473190a36f8fbfd09c1",
"reactionHash": "a47124be7ff465134e631b60cecd4f5f7ba35fa3d875eec3bad6a3b59d6c291e"
},
"children": [
{
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"moleculeId": "sa_e565e9e87b992207de0fd6b4",
"parentId": "17337",
"isLeaf": false,
"molecule": {
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"inchikey": "IWANJGONQQFUIO-UHFFFAOYSA-N",
"smiles": "CCCCc1nc2c(N)nc3ccccc3c2n1CCCNC(=O)OC(C)(C)C"
},
"smiles": "CCCCc1nc2c(N)nc3ccccc3c2n1CCCNC(=O)OC(C)(C)C",
"reactionStepId": "sa_c6cdc99df46c3954541ac503",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130225555A1;0281;1413134\",\"rsmi\":\"[NH3:17].[O-][n+:15]1[c:10]2[c:9]([c:8]3[c:7]([n:6][c:5]([CH2:4][CH2:3][CH2:2][CH3:1])[n:18]3[CH2:19][CH2:20][CH2:21][NH:22][C:23](=[O:24])[O:25][C:26]([CH3:27])([CH3:28])[CH3:29])[cH:16]1)[cH:14][cH:13][cH:12][cH:11]2>Cc1ccc(S(=O)(=O)Cl)cc1.ClCCl.ClCCl.O.O>[CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([c:9]3[c:10]([cH:11][cH:12][cH:13][cH:14]3)[n:15][c:16]2[NH2:17])[n:18]1[CH2:19][CH2:20][CH2:21][NH:22][C:23](=[O:24])[O:25][C:26]([CH3:27])([CH3:28])[CH3:29]\"},\"mapped_reaction_smiles\":\"[NH3:17].[O-][n+:15]1[c:10]2[c:9]([c:8]3[c:7]([n:6][c:5]([CH2:4][CH2:3][CH2:2][CH3:1])[n:18]3[CH2:19][CH2:20][CH2:21][NH:22][C:23](=[O:24])[O:25][C:26]([CH3:27])([CH3:28])[CH3:29])[cH:16]1)[cH:14][cH:13][cH:12][cH:11]2>Cc1ccc(S(=O)(=O)Cl)cc1.ClCCl.ClCCl.O.O>[CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([c:9]3[c:10]([cH:11][cH:12][cH:13][cH:14]3)[n:15][c:16]2[NH2:17])[n:18]1[CH2:19][CH2:20][CH2:21][NH:22][C:23](=[O:24])[O:25][C:26]([CH3:27])([CH3:28])[CH3:29]\"}",
"reactionStep": {
"id": "sa_c6cdc99df46c3954541ac503",
"reactionHash": "2fab6c59d9fe03bd6abced4a2800b0f0ecf5594b0d0b11917f0267b34d0b79e0"
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"children": [
{
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"routeId": "sa_73897196c71bed0d58d41710",
"moleculeId": "sa_324db7f12054b5c354fe2341",
"parentId": "17338",
"isLeaf": false,
"molecule": {
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"inchikey": "OWNPTEYMAPTMSL-UHFFFAOYSA-N",
"smiles": "CCCCc1nc2c[n+]([O-])c3ccccc3c2n1CCCNC(=O)OC(C)(C)C"
},
"smiles": "CCCCc1nc2c[n+]([O-])c3ccccc3c2n1CCCNC(=O)OC(C)(C)C",
"reactionStepId": "sa_8d7a5aead561597ffd3f274b",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130225555A1;0279;1413133\",\"rsmi\":\"O=C(O[OH:16])c1cccc(Cl)c1.[CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([c:9]3[c:10]([cH:11][cH:12][cH:13][cH:14]3)[n:15][cH:17]2)[n:18]1[CH2:19][CH2:20][CH2:21][NH:22][C:23](=[O:24])[O:25][C:26]([CH3:27])([CH3:28])[CH3:29]>ClCCl.O=S(=O)(O)O.[Na+]>[CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([c:9]3[c:10]([cH:11][cH:12][cH:13][cH:14]3)[n+:15]([O-:16])[cH:17]2)[n:18]1[CH2:19][CH2:20][CH2:21][NH:22][C:23](=[O:24])[O:25][C:26]([CH3:27])([CH3:28])[CH3:29]\"},\"mapped_reaction_smiles\":\"O=C(O[OH:16])c1cccc(Cl)c1.[CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([c:9]3[c:10]([cH:11][cH:12][cH:13][cH:14]3)[n:15][cH:17]2)[n:18]1[CH2:19][CH2:20][CH2:21][NH:22][C:23](=[O:24])[O:25][C:26]([CH3:27])([CH3:28])[CH3:29]>ClCCl.O=S(=O)(O)O.[Na+]>[CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([c:9]3[c:10]([cH:11][cH:12][cH:13][cH:14]3)[n+:15]([O-:16])[cH:17]2)[n:18]1[CH2:19][CH2:20][CH2:21][NH:22][C:23](=[O:24])[O:25][C:26]([CH3:27])([CH3:28])[CH3:29]\"}",
"reactionStep": {
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"children": [
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"moleculeId": "sa_292aab804b3670e84ce954f3",
"parentId": "17339",
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"molecule": {
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"smiles": "O=C(OO)c1cccc(Cl)c1"
},
"smiles": "O=C(OO)c1cccc(Cl)c1",
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{
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"smiles": "CCCCc1nc2cnc3ccccc3c2n1CCCNC(=O)OC(C)(C)C"
},
"smiles": "CCCCc1nc2cnc3ccccc3c2n1CCCNC(=O)OC(C)(C)C",
"reactionStepId": "sa_56892eb6092834eae60c7f77",
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"metadata": "{\"annotations\":{\"ID\":\"US20130225555A1;0276;1413132\",\"rsmi\":\"O=[C:5](Cl)[CH2:4][CH2:3][CH2:2][CH3:1].[NH2:6][c:7]1[c:8]([NH:17][CH2:18][CH2:19][CH2:20][NH:21][C:22](=[O:23])[O:24][C:25]([CH3:26])([CH3:27])[CH3:28])[c:9]2[c:10]([cH:11][cH:12][cH:13][cH:14]2)[n:15][cH:16]1>CN1CCCC1=O>[CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([c:9]3[c:10]([cH:11][cH:12][cH:13][cH:14]3)[n:15][cH:16]2)[n:17]1[CH2:18][CH2:19][CH2:20][NH:21][C:22](=[O:23])[O:24][C:25]([CH3:26])([CH3:27])[CH3:28]\"},\"mapped_reaction_smiles\":\"O=[C:5](Cl)[CH2:4][CH2:3][CH2:2][CH3:1].[NH2:6][c:7]1[c:8]([NH:17][CH2:18][CH2:19][CH2:20][NH:21][C:22](=[O:23])[O:24][C:25]([CH3:26])([CH3:27])[CH3:28])[c:9]2[c:10]([cH:11][cH:12][cH:13][cH:14]2)[n:15][cH:16]1>CN1CCCC1=O>[CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([c:9]3[c:10]([cH:11][cH:12][cH:13][cH:14]3)[n:15][cH:16]2)[n:17]1[CH2:18][CH2:19][CH2:20][NH:21][C:22](=[O:23])[O:24][C:25]([CH3:26])([CH3:27])[CH3:28]\"}",
"reactionStep": {
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"children": [
{
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"molecule": {
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"smiles": "CC(C)(C)OC(=O)NCCCNc1c(N)cnc2ccccc12"
},
"smiles": "CC(C)(C)OC(=O)NCCCNc1c(N)cnc2ccccc12",
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