Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CCS(=O)(=O)N1CCC(Nc2cc(-c3cccc(NCc4cccc(F)c4)n3)c(Cl)cn2)CC1
InChiKey
TZNKIGIHGJZECV-UHFFFAOYSA-N
Route Signature
65313475668dabd901eec543524bd3191a851efa0776549fa623ce7f935d511d
Synthesis route with 5 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_06bc72d1bebbc5b1fe7b9790",
"signature": "65313475668dabd901eec543524bd3191a851efa0776549fa623ce7f935d511d",
"contentHash": "011759a1b4ae79356a75b988a06acb16a3773ac291eb0723f997be31189fb776",
"length": 5,
"isConvergent": false
},
"target": {
"id": "sa_d7038cb103d37724e36d8353",
"benchmarkSetId": "f925e688d731a0ad4e3aa6a505df094f6d3ca64ce3facc312bc5f64731921b33",
"targetId": "n5-04606",
"moleculeId": "sa_0a5af874bb9dc24f3fd6cbdf",
"smiles": "CCS(=O)(=O)N1CCC(Nc2cc(-c3cccc(NCc4cccc(F)c4)n3)c(Cl)cn2)CC1",
"routeLength": 5,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_0a5af874bb9dc24f3fd6cbdf",
"inchikey": "TZNKIGIHGJZECV-UHFFFAOYSA-N",
"smiles": "CCS(=O)(=O)N1CCC(Nc2cc(-c3cccc(NCc4cccc(F)c4)n3)c(Cl)cn2)CC1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "7369",
"routeId": "sa_06bc72d1bebbc5b1fe7b9790",
"moleculeId": "sa_0a5af874bb9dc24f3fd6cbdf",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_0a5af874bb9dc24f3fd6cbdf",
"inchikey": "TZNKIGIHGJZECV-UHFFFAOYSA-N",
"smiles": "CCS(=O)(=O)N1CCC(Nc2cc(-c3cccc(NCc4cccc(F)c4)n3)c(Cl)cn2)CC1"
},
"smiles": "CCS(=O)(=O)N1CCC(Nc2cc(-c3cccc(NCc4cccc(F)c4)n3)c(Cl)cn2)CC1",
"reactionStepId": "sa_4103b18cba8c20bbd50d03a1",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20110028492A1;0390;1010235\",\"rsmi\":\"Cl[S:3]([CH2:2][CH3:1])(=[O:4])=[O:5].[NH:6]1[CH2:7][CH2:8][CH:9]([NH:10][c:11]2[n:12][cH:13][c:14]([Cl:15])[c:16](-[c:17]3[n:18][c:19]([NH:20][CH2:21][c:22]4[cH:23][c:24]([F:25])[cH:26][cH:27][cH:28]4)[cH:29][cH:30][cH:31]3)[cH:32]2)[CH2:33][CH2:34]1>CS(C)=O.ClCCl>[CH3:1][CH2:2][S:3](=[O:4])(=[O:5])[N:6]1[CH2:7][CH2:8][CH:9]([NH:10][c:11]2[n:12][cH:13][c:14]([Cl:15])[c:16](-[c:17]3[n:18][c:19]([NH:20][CH2:21][c:22]4[cH:23][c:24]([F:25])[cH:26][cH:27][cH:28]4)[cH:29][cH:30][cH:31]3)[cH:32]2)[CH2:33][CH2:34]1\"},\"mapped_reaction_smiles\":\"Cl[S:3]([CH2:2][CH3:1])(=[O:4])=[O:5].[NH:6]1[CH2:7][CH2:8][CH:9]([NH:10][c:11]2[n:12][cH:13][c:14]([Cl:15])[c:16](-[c:17]3[n:18][c:19]([NH:20][CH2:21][c:22]4[cH:23][c:24]([F:25])[cH:26][cH:27][cH:28]4)[cH:29][cH:30][cH:31]3)[cH:32]2)[CH2:33][CH2:34]1>CS(C)=O.ClCCl>[CH3:1][CH2:2][S:3](=[O:4])(=[O:5])[N:6]1[CH2:7][CH2:8][CH:9]([NH:10][c:11]2[n:12][cH:13][c:14]([Cl:15])[c:16](-[c:17]3[n:18][c:19]([NH:20][CH2:21][c:22]4[cH:23][c:24]([F:25])[cH:26][cH:27][cH:28]4)[cH:29][cH:30][cH:31]3)[cH:32]2)[CH2:33][CH2:34]1\"}",
"reactionStep": {
"id": "sa_4103b18cba8c20bbd50d03a1",
"reactionHash": "60870f6b60d1f79fb87529fbdf9b9cf6bd68f0834471f078dba02dd5e11f233a"
},
"children": [
{
"id": "7370",
"routeId": "sa_06bc72d1bebbc5b1fe7b9790",
"moleculeId": "sa_a505ad769cb2dff204290187",
"parentId": "7369",
"isLeaf": true,
"molecule": {
"id": "sa_a505ad769cb2dff204290187",
"inchikey": "FRYHCSODNHYDPU-UHFFFAOYSA-N",
"smiles": "CCS(=O)(=O)Cl"
},
"smiles": "CCS(=O)(=O)Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "7371",
"routeId": "sa_06bc72d1bebbc5b1fe7b9790",
"moleculeId": "sa_627db09c71880c1bc5422098",
"parentId": "7369",
"isLeaf": false,
"molecule": {
"id": "sa_627db09c71880c1bc5422098",
"inchikey": "PXPAHPCLBJKTEW-UHFFFAOYSA-N",
"smiles": "Fc1cccc(CNc2cccc(-c3cc(NC4CCNCC4)ncc3Cl)n2)c1"
},
"smiles": "Fc1cccc(CNc2cccc(-c3cc(NC4CCNCC4)ncc3Cl)n2)c1",
"reactionStepId": "sa_63cb94f4fb1c501bd8760935",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20110028492A1;0388;1010234\",\"rsmi\":\"CC(C)(C)OC(=O)[N:21]1[CH2:20][CH2:19][CH:18]([NH:17][c:16]2[cH:15][c:14](-[c:13]3[cH:12][cH:11][cH:10][c:9]([NH:8][CH2:7][c:6]4[cH:5][cH:4][cH:3][c:2]([F:1])[cH:29]4)[n:28]3)[c:26]([Cl:27])[cH:25][n:24]2)[CH2:23][CH2:22]1>C1COCCO1.Cl>[F:1][c:2]1[cH:3][cH:4][cH:5][c:6]([CH2:7][NH:8][c:9]2[cH:10][cH:11][cH:12][c:13](-[c:14]3[cH:15][c:16]([NH:17][CH:18]4[CH2:19][CH2:20][NH:21][CH2:22][CH2:23]4)[n:24][cH:25][c:26]3[Cl:27])[n:28]2)[cH:29]1\"},\"mapped_reaction_smiles\":\"CC(C)(C)OC(=O)[N:21]1[CH2:20][CH2:19][CH:18]([NH:17][c:16]2[cH:15][c:14](-[c:13]3[cH:12][cH:11][cH:10][c:9]([NH:8][CH2:7][c:6]4[cH:5][cH:4][cH:3][c:2]([F:1])[cH:29]4)[n:28]3)[c:26]([Cl:27])[cH:25][n:24]2)[CH2:23][CH2:22]1>C1COCCO1.Cl>[F:1][c:2]1[cH:3][cH:4][cH:5][c:6]([CH2:7][NH:8][c:9]2[cH:10][cH:11][cH:12][c:13](-[c:14]3[cH:15][c:16]([NH:17][CH:18]4[CH2:19][CH2:20][NH:21][CH2:22][CH2:23]4)[n:24][cH:25][c:26]3[Cl:27])[n:28]2)[cH:29]1\"}",
"reactionStep": {
"id": "sa_63cb94f4fb1c501bd8760935",
"reactionHash": "f81f6ff53a1d62dd662d7d33c0af1f6fe23efafa9fb8276edde7e5bdda2a40fe"
},
"children": [
{
"id": "7372",
"routeId": "sa_06bc72d1bebbc5b1fe7b9790",
"moleculeId": "sa_753b1ff67721f2b68cf1635f",
"parentId": "7371",
"isLeaf": false,
"molecule": {
"id": "sa_753b1ff67721f2b68cf1635f",
"inchikey": "CPOOLWPLIIVVQF-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)N1CCC(Nc2cc(-c3cccc(NCc4cccc(F)c4)n3)c(Cl)cn2)CC1"
},
"smiles": "CC(C)(C)OC(=O)N1CCC(Nc2cc(-c3cccc(NCc4cccc(F)c4)n3)c(Cl)cn2)CC1",
"reactionStepId": "sa_5759fa87b7301e4dab4072e1",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20110028492A1;0387;1010233\",\"rsmi\":\"F[c:21]1[n:20][c:19](-[c:18]2[c:16]([Cl:17])[cH:15][n:14][c:13]([NH:12][CH:11]3[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:36][CH2:35]3)[cH:34]2)[cH:33][cH:32][cH:31]1.[NH2:22][CH2:23][c:24]1[cH:25][c:26]([F:27])[cH:28][cH:29][cH:30]1>CS(C)=O>[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[n:14][cH:15][c:16]([Cl:17])[c:18](-[c:19]3[n:20][c:21]([NH:22][CH2:23][c:24]4[cH:25][c:26]([F:27])[cH:28][cH:29][cH:30]4)[cH:31][cH:32][cH:33]3)[cH:34]2)[CH2:35][CH2:36]1\"},\"mapped_reaction_smiles\":\"F[c:21]1[n:20][c:19](-[c:18]2[c:16]([Cl:17])[cH:15][n:14][c:13]([NH:12][CH:11]3[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:36][CH2:35]3)[cH:34]2)[cH:33][cH:32][cH:31]1.[NH2:22][CH2:23][c:24]1[cH:25][c:26]([F:27])[cH:28][cH:29][cH:30]1>CS(C)=O>[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[n:14][cH:15][c:16]([Cl:17])[c:18](-[c:19]3[n:20][c:21]([NH:22][CH2:23][c:24]4[cH:25][c:26]([F:27])[cH:28][cH:29][cH:30]4)[cH:31][cH:32][cH:33]3)[cH:34]2)[CH2:35][CH2:36]1\"}",
"reactionStep": {
"id": "sa_5759fa87b7301e4dab4072e1",
"reactionHash": "21bc2ebe8fa03fafa4f689ddf1c7a82584b203a91167b30f19693c5965257dfd"
},
"children": [
{
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"moleculeId": "sa_92df37e5118fd16965251fd6",
"parentId": "7372",
"isLeaf": false,
"molecule": {
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"inchikey": "GWJRDBLDTUHBEB-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)N1CCC(Nc2cc(-c3cccc(F)n3)c(Cl)cn2)CC1"
},
"smiles": "CC(C)(C)OC(=O)N1CCC(Nc2cc(-c3cccc(F)n3)c(Cl)cn2)CC1",
"reactionStepId": "sa_4aa963150c2a445fd2e3a2a3",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20110028492A1;0386;1010232\",\"rsmi\":\"CC1(C)OB([c:19]2[n:20][c:21]([F:22])[cH:23][cH:24][cH:25]2)OC1(C)C.I[c:18]1[c:16]([Cl:17])[cH:15][n:14][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])[CH2:28][CH2:27]2)[cH:26]1>CCOC(C)=O.COCCOC.ClCCl.Cl[Pd]Cl.O=C(O)O.[Fe+2].[Na+].[Na+]>[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[n:14][cH:15][c:16]([Cl:17])[c:18](-[c:19]3[n:20][c:21]([F:22])[cH:23][cH:24][cH:25]3)[cH:26]2)[CH2:27][CH2:28]1\"},\"mapped_reaction_smiles\":\"CC1(C)OB([c:19]2[n:20][c:21]([F:22])[cH:23][cH:24][cH:25]2)OC1(C)C.I[c:18]1[c:16]([Cl:17])[cH:15][n:14][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])[CH2:28][CH2:27]2)[cH:26]1>CCOC(C)=O.COCCOC.ClCCl.Cl[Pd]Cl.O=C(O)O.[Fe+2].[Na+].[Na+]>[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[n:14][cH:15][c:16]([Cl:17])[c:18](-[c:19]3[n:20][c:21]([F:22])[cH:23][cH:24][cH:25]3)[cH:26]2)[CH2:27][CH2:28]1\"}",
"reactionStep": {
"id": "sa_4aa963150c2a445fd2e3a2a3",
"reactionHash": "3dc7543faf3ae947676c0937c7f66d61ba22f61b78fdfec7e858ecdf4a8b9026"
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"children": [
{
"id": "7374",
"routeId": "sa_06bc72d1bebbc5b1fe7b9790",
"moleculeId": "sa_806161965d500af3f5921a50",
"parentId": "7373",
"isLeaf": true,
"molecule": {
"id": "sa_806161965d500af3f5921a50",
"inchikey": "WGPVNHXZZUGSMO-UHFFFAOYSA-N",
"smiles": "CC1(C)OB(c2cccc(F)n2)OC1(C)C"
},
"smiles": "CC1(C)OB(c2cccc(F)n2)OC1(C)C",
"reactionStepId": null,
"template": null,
"metadata": null,
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},
{
"id": "7375",
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"molecule": {
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"inchikey": "WVDAIQRWMQQRPG-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)N1CCC(Nc2cc(I)c(Cl)cn2)CC1"
},
"smiles": "CC(C)(C)OC(=O)N1CCC(Nc2cc(I)c(Cl)cn2)CC1",
"reactionStepId": "sa_1d90c057987007d5558f9b45",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20110028492A1;0385;1010231\",\"rsmi\":\"F[c:13]1[n:14][cH:15][c:16]([Cl:17])[c:18]([I:19])[cH:20]1.[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])[CH2:21][CH2:22]1>CCOC(C)=O.CS(C)=O>[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[n:14][cH:15][c:16]([Cl:17])[c:18]([I:19])[cH:20]2)[CH2:21][CH2:22]1\"},\"mapped_reaction_smiles\":\"F[c:13]1[n:14][cH:15][c:16]([Cl:17])[c:18]([I:19])[cH:20]1.[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])[CH2:21][CH2:22]1>CCOC(C)=O.CS(C)=O>[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[n:14][cH:15][c:16]([Cl:17])[c:18]([I:19])[cH:20]2)[CH2:21][CH2:22]1\"}",
"reactionStep": {
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"children": [
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"moleculeId": "sa_b22db05da77fca83b9143540",
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"molecule": {
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{
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"smiles": "Fc1cc(I)c(Cl)cn1"
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{
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"molecule": {
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"smiles": "NCc1cccc(F)c1"
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}
]
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]
}
]
}
}