Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
C=CC(=O)N1CCC(c2ccc(C(N)=O)c(-c3ccc(C(=O)Nc4ccccc4)cc3)n2)CC1
InChiKey
QWXLRBXLPIJPFH-UHFFFAOYSA-N
Route Signature
6bca97dcc06ee2f0e1f9676e713cff7caca1f913d473afcbf6070cf63881e3dd
Synthesis route with 6 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_25370d865fcc9b0f51fa29bf",
"signature": "6bca97dcc06ee2f0e1f9676e713cff7caca1f913d473afcbf6070cf63881e3dd",
"contentHash": "4bc72d8aea7ce5d9ea4d36147be002c28cdb6bbfee1ee358fa15f1b854ca3353",
"length": 6,
"isConvergent": false
},
"target": {
"id": "sa_87904ca12620c3000f85d008",
"benchmarkSetId": "61e696668b63e77d7c2a29c0821768e1c383de8313852d6e995224859494442e",
"targetId": "n5-00538",
"moleculeId": "sa_98d2edd1056ec7d5cefea3de",
"smiles": "C=CC(=O)N1CCC(c2ccc(C(N)=O)c(-c3ccc(C(=O)Nc4ccccc4)cc3)n2)CC1",
"routeLength": 6,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_98d2edd1056ec7d5cefea3de",
"inchikey": "QWXLRBXLPIJPFH-UHFFFAOYSA-N",
"smiles": "C=CC(=O)N1CCC(c2ccc(C(N)=O)c(-c3ccc(C(=O)Nc4ccccc4)cc3)n2)CC1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "13452",
"routeId": "sa_25370d865fcc9b0f51fa29bf",
"moleculeId": "sa_98d2edd1056ec7d5cefea3de",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_98d2edd1056ec7d5cefea3de",
"inchikey": "QWXLRBXLPIJPFH-UHFFFAOYSA-N",
"smiles": "C=CC(=O)N1CCC(c2ccc(C(N)=O)c(-c3ccc(C(=O)Nc4ccccc4)cc3)n2)CC1"
},
"smiles": "C=CC(=O)N1CCC(c2ccc(C(N)=O)c(-c3ccc(C(=O)Nc4ccccc4)cc3)n2)CC1",
"reactionStepId": "sa_5d8219eed1c8ad7c85981ec7",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160237075A1;0532;1923094\",\"rsmi\":\"Cl[C:3]([CH:2]=[CH2:1])=[O:4].[NH:5]1[CH2:6][CH2:7][CH:8]([c:9]2[n:10][c:11](-[c:12]3[cH:13][cH:14][c:15]([C:16](=[O:17])[NH:18][c:19]4[cH:20][cH:21][cH:22][cH:23][cH:24]4)[cH:25][cH:26]3)[c:27]([C:28]([NH2:29])=[O:30])[cH:31][cH:32]2)[CH2:33][CH2:34]1>CCN(C(C)C)C(C)C.ClCCl.O>[CH2:1]=[CH:2][C:3](=[O:4])[N:5]1[CH2:6][CH2:7][CH:8]([c:9]2[n:10][c:11](-[c:12]3[cH:13][cH:14][c:15]([C:16](=[O:17])[NH:18][c:19]4[cH:20][cH:21][cH:22][cH:23][cH:24]4)[cH:25][cH:26]3)[c:27]([C:28]([NH2:29])=[O:30])[cH:31][cH:32]2)[CH2:33][CH2:34]1\"},\"mapped_reaction_smiles\":\"Cl[C:3]([CH:2]=[CH2:1])=[O:4].[NH:5]1[CH2:6][CH2:7][CH:8]([c:9]2[n:10][c:11](-[c:12]3[cH:13][cH:14][c:15]([C:16](=[O:17])[NH:18][c:19]4[cH:20][cH:21][cH:22][cH:23][cH:24]4)[cH:25][cH:26]3)[c:27]([C:28]([NH2:29])=[O:30])[cH:31][cH:32]2)[CH2:33][CH2:34]1>CCN(C(C)C)C(C)C.ClCCl.O>[CH2:1]=[CH:2][C:3](=[O:4])[N:5]1[CH2:6][CH2:7][CH:8]([c:9]2[n:10][c:11](-[c:12]3[cH:13][cH:14][c:15]([C:16](=[O:17])[NH:18][c:19]4[cH:20][cH:21][cH:22][cH:23][cH:24]4)[cH:25][cH:26]3)[c:27]([C:28]([NH2:29])=[O:30])[cH:31][cH:32]2)[CH2:33][CH2:34]1\"}",
"reactionStep": {
"id": "sa_5d8219eed1c8ad7c85981ec7",
"reactionHash": "6134be7912b8e6abca7fc6a6f35a23aa6a0236ee0a7ca484c06eb78f935d047a"
},
"children": [
{
"id": "13453",
"routeId": "sa_25370d865fcc9b0f51fa29bf",
"moleculeId": "sa_8d7619d85011994fa809f1ac",
"parentId": "13452",
"isLeaf": false,
"molecule": {
"id": "sa_8d7619d85011994fa809f1ac",
"inchikey": "FBGTZOSKUKJSOI-UHFFFAOYSA-N",
"smiles": "NC(=O)c1ccc(C2CCNCC2)nc1-c1ccc(C(=O)Nc2ccccc2)cc1"
},
"smiles": "NC(=O)c1ccc(C2CCNCC2)nc1-c1ccc(C(=O)Nc2ccccc2)cc1",
"reactionStepId": "sa_d2f46ee6c3206a12e79c23c9",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160237075A1;0530;1923093\",\"rsmi\":\"CC(C)(C)OC(=O)[N:26]1[CH2:25][CH2:24][CH:23]([c:22]2[n:21][c:5](-[c:6]3[cH:7][cH:8][c:9]([C:10](=[O:11])[NH:12][c:13]4[cH:14][cH:15][cH:16][cH:17][cH:18]4)[cH:19][cH:20]3)[c:4]([C:2]([NH2:1])=[O:3])[cH:30][cH:29]2)[CH2:28][CH2:27]1>ClCCl.O=C(O)C(F)(F)F>[NH2:1][C:2](=[O:3])[c:4]1[c:5](-[c:6]2[cH:7][cH:8][c:9]([C:10](=[O:11])[NH:12][c:13]3[cH:14][cH:15][cH:16][cH:17][cH:18]3)[cH:19][cH:20]2)[n:21][c:22]([CH:23]2[CH2:24][CH2:25][NH:26][CH2:27][CH2:28]2)[cH:29][cH:30]1\"},\"mapped_reaction_smiles\":\"CC(C)(C)OC(=O)[N:26]1[CH2:25][CH2:24][CH:23]([c:22]2[n:21][c:5](-[c:6]3[cH:7][cH:8][c:9]([C:10](=[O:11])[NH:12][c:13]4[cH:14][cH:15][cH:16][cH:17][cH:18]4)[cH:19][cH:20]3)[c:4]([C:2]([NH2:1])=[O:3])[cH:30][cH:29]2)[CH2:28][CH2:27]1>ClCCl.O=C(O)C(F)(F)F>[NH2:1][C:2](=[O:3])[c:4]1[c:5](-[c:6]2[cH:7][cH:8][c:9]([C:10](=[O:11])[NH:12][c:13]3[cH:14][cH:15][cH:16][cH:17][cH:18]3)[cH:19][cH:20]2)[n:21][c:22]([CH:23]2[CH2:24][CH2:25][NH:26][CH2:27][CH2:28]2)[cH:29][cH:30]1\"}",
"reactionStep": {
"id": "sa_d2f46ee6c3206a12e79c23c9",
"reactionHash": "efa5287d697a1ae93eaecc8028dadc42b362bc4d5d8a747dccc703eea05fcdb7"
},
"children": [
{
"id": "13454",
"routeId": "sa_25370d865fcc9b0f51fa29bf",
"moleculeId": "sa_ff0272de2e02ad960fe28d60",
"parentId": "13453",
"isLeaf": false,
"molecule": {
"id": "sa_ff0272de2e02ad960fe28d60",
"inchikey": "BXXBXEQWIWIKSM-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)N1CCC(c2ccc(C(N)=O)c(-c3ccc(C(=O)Nc4ccccc4)cc3)n2)CC1"
},
"smiles": "CC(C)(C)OC(=O)N1CCC(c2ccc(C(N)=O)c(-c3ccc(C(=O)Nc4ccccc4)cc3)n2)CC1",
"reactionStepId": "sa_bfa729f792172b992cc49bd4",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160237075A1;0529;1923092\",\"rsmi\":\"O[C:19]([c:18]1[cH:17][cH:16][c:15](-[c:14]2[n:13][c:12]([CH:11]3[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:37][CH2:36]3)[cH:35][cH:34][c:30]2[C:31]([NH2:32])=[O:33])[cH:29][cH:28]1)=[O:20].[NH2:21][c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1>CCN(C(C)C)C(C)C.CCOC(C)=O.CN(C)C(On1nnc2cccnc21)=[N+](C)C.CN(C)C=O.F[PH](F)(F)(F)(F)F>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH:11]([c:12]2[n:13][c:14](-[c:15]3[cH:16][cH:17][c:18]([C:19](=[O:20])[NH:21][c:22]4[cH:23][cH:24][cH:25][cH:26][cH:27]4)[cH:28][cH:29]3)[c:30]([C:31]([NH2:32])=[O:33])[cH:34][cH:35]2)[CH2:36][CH2:37]1\"},\"mapped_reaction_smiles\":\"O[C:19]([c:18]1[cH:17][cH:16][c:15](-[c:14]2[n:13][c:12]([CH:11]3[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:37][CH2:36]3)[cH:35][cH:34][c:30]2[C:31]([NH2:32])=[O:33])[cH:29][cH:28]1)=[O:20].[NH2:21][c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1>CCN(C(C)C)C(C)C.CCOC(C)=O.CN(C)C(On1nnc2cccnc21)=[N+](C)C.CN(C)C=O.F[PH](F)(F)(F)(F)F>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH:11]([c:12]2[n:13][c:14](-[c:15]3[cH:16][cH:17][c:18]([C:19](=[O:20])[NH:21][c:22]4[cH:23][cH:24][cH:25][cH:26][cH:27]4)[cH:28][cH:29]3)[c:30]([C:31]([NH2:32])=[O:33])[cH:34][cH:35]2)[CH2:36][CH2:37]1\"}",
"reactionStep": {
"id": "sa_bfa729f792172b992cc49bd4",
"reactionHash": "1fc52c4b45f11a38468882412ac83f6c40acd0fb6fc2af36ec3877496b8f0262"
},
"children": [
{
"id": "13455",
"routeId": "sa_25370d865fcc9b0f51fa29bf",
"moleculeId": "sa_2bdfaa4b790f1039fa325d28",
"parentId": "13454",
"isLeaf": false,
"molecule": {
"id": "sa_2bdfaa4b790f1039fa325d28",
"inchikey": "DNHYOCCYKUNCLX-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)N1CCC(c2ccc(C(N)=O)c(-c3ccc(C(=O)O)cc3)n2)CC1"
},
"smiles": "CC(C)(C)OC(=O)N1CCC(c2ccc(C(N)=O)c(-c3ccc(C(=O)O)cc3)n2)CC1",
"reactionStepId": "sa_6990fa7173c0ce7f05e7e6ae",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160237075A1;0528;1923091\",\"rsmi\":\"C[O:26][C:24]([c:23]1[cH:22][cH:21][c:20](-[c:19]2[c:15]([C:16]([NH2:17])=[O:18])[cH:14][cH:13][c:12]([CH:11]3[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:31][CH2:30]3)[n:29]2)[cH:28][cH:27]1)=[O:25]>C1CCOC1.O.[Li+].O>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH:11]([c:12]2[cH:13][cH:14][c:15]([C:16]([NH2:17])=[O:18])[c:19](-[c:20]3[cH:21][cH:22][c:23]([C:24](=[O:25])[OH:26])[cH:27][cH:28]3)[n:29]2)[CH2:30][CH2:31]1\"},\"mapped_reaction_smiles\":\"C[O:26][C:24]([c:23]1[cH:22][cH:21][c:20](-[c:19]2[c:15]([C:16]([NH2:17])=[O:18])[cH:14][cH:13][c:12]([CH:11]3[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:31][CH2:30]3)[n:29]2)[cH:28][cH:27]1)=[O:25]>C1CCOC1.O.[Li+].O>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH:11]([c:12]2[cH:13][cH:14][c:15]([C:16]([NH2:17])=[O:18])[c:19](-[c:20]3[cH:21][cH:22][c:23]([C:24](=[O:25])[OH:26])[cH:27][cH:28]3)[n:29]2)[CH2:30][CH2:31]1\"}",
"reactionStep": {
"id": "sa_6990fa7173c0ce7f05e7e6ae",
"reactionHash": "a239530397fa262bce2567488d8e515d2328fcc7e83b13bfd60b279d75cd4b4e"
},
"children": [
{
"id": "13456",
"routeId": "sa_25370d865fcc9b0f51fa29bf",
"moleculeId": "sa_6cc59b5371d17acbcfef586e",
"parentId": "13455",
"isLeaf": false,
"molecule": {
"id": "sa_6cc59b5371d17acbcfef586e",
"inchikey": "CNSDMACTYUWUFO-UHFFFAOYSA-N",
"smiles": "COC(=O)c1ccc(-c2nc(C3CCN(C(=O)OC(C)(C)C)CC3)ccc2C(N)=O)cc1"
},
"smiles": "COC(=O)c1ccc(-c2nc(C3CCN(C(=O)OC(C)(C)C)CC3)ccc2C(N)=O)cc1",
"reactionStepId": "sa_507afe37547549f959440459",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160237075A1;0527;1923090\",\"rsmi\":\"[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8](-[c:9]2[c:10]([C:11]([NH2:12])=[O:13])[cH:14][cH:15][c:16]([C:17]3=[CH:18][CH2:19][N:20]([C:21](=[O:22])[O:23][C:24]([CH3:25])([CH3:26])[CH3:27])[CH2:28][CH2:29]3)[n:30]2)[cH:31][cH:32]1>CO.[Pd]>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8](-[c:9]2[c:10]([C:11]([NH2:12])=[O:13])[cH:14][cH:15][c:16]([CH:17]3[CH2:18][CH2:19][N:20]([C:21](=[O:22])[O:23][C:24]([CH3:25])([CH3:26])[CH3:27])[CH2:28][CH2:29]3)[n:30]2)[cH:31][cH:32]1\"},\"mapped_reaction_smiles\":\"[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8](-[c:9]2[c:10]([C:11]([NH2:12])=[O:13])[cH:14][cH:15][c:16]([C:17]3=[CH:18][CH2:19][N:20]([C:21](=[O:22])[O:23][C:24]([CH3:25])([CH3:26])[CH3:27])[CH2:28][CH2:29]3)[n:30]2)[cH:31][cH:32]1>CO.[Pd]>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8](-[c:9]2[c:10]([C:11]([NH2:12])=[O:13])[cH:14][cH:15][c:16]([CH:17]3[CH2:18][CH2:19][N:20]([C:21](=[O:22])[O:23][C:24]([CH3:25])([CH3:26])[CH3:27])[CH2:28][CH2:29]3)[n:30]2)[cH:31][cH:32]1\"}",
"reactionStep": {
"id": "sa_507afe37547549f959440459",
"reactionHash": "8060f82bc1b2f056dc5449a7b9a9dadba0da86f794a044b35787405e344eee6f"
},
"children": [
{
"id": "13457",
"routeId": "sa_25370d865fcc9b0f51fa29bf",
"moleculeId": "sa_ff06325ab62faa996033ee2c",
"parentId": "13456",
"isLeaf": false,
"molecule": {
"id": "sa_ff06325ab62faa996033ee2c",
"inchikey": "RGZDESVZAKTFDH-UHFFFAOYSA-N",
"smiles": "COC(=O)c1ccc(-c2nc(C3=CCN(C(=O)OC(C)(C)C)CC3)ccc2C(N)=O)cc1"
},
"smiles": "COC(=O)c1ccc(-c2nc(C3=CCN(C(=O)OC(C)(C)C)CC3)ccc2C(N)=O)cc1",
"reactionStepId": "sa_9cc5430fa012da1d0783a3a8",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160237075A1;0526;1923089\",\"rsmi\":\"CC1(C)OB([C:17]2=[CH:18][CH2:19][N:20]([C:21](=[O:22])[O:23][C:24]([CH3:25])([CH3:26])[CH3:27])[CH2:28][CH2:29]2)OC1(C)C.Cl[c:16]1[cH:15][cH:14][c:10]([C:11]([NH2:12])=[O:13])[c:9](-[c:8]2[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:32][cH:31]2)[n:30]1>COCCOC.Cl[Pd]Cl.O.O=C(O)O.[Cs+].[Cs+].[Fe+2]>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8](-[c:9]2[c:10]([C:11]([NH2:12])=[O:13])[cH:14][cH:15][c:16]([C:17]3=[CH:18][CH2:19][N:20]([C:21](=[O:22])[O:23][C:24]([CH3:25])([CH3:26])[CH3:27])[CH2:28][CH2:29]3)[n:30]2)[cH:31][cH:32]1\"},\"mapped_reaction_smiles\":\"CC1(C)OB([C:17]2=[CH:18][CH2:19][N:20]([C:21](=[O:22])[O:23][C:24]([CH3:25])([CH3:26])[CH3:27])[CH2:28][CH2:29]2)OC1(C)C.Cl[c:16]1[cH:15][cH:14][c:10]([C:11]([NH2:12])=[O:13])[c:9](-[c:8]2[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:32][cH:31]2)[n:30]1>COCCOC.Cl[Pd]Cl.O.O=C(O)O.[Cs+].[Cs+].[Fe+2]>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8](-[c:9]2[c:10]([C:11]([NH2:12])=[O:13])[cH:14][cH:15][c:16]([C:17]3=[CH:18][CH2:19][N:20]([C:21](=[O:22])[O:23][C:24]([CH3:25])([CH3:26])[CH3:27])[CH2:28][CH2:29]3)[n:30]2)[cH:31][cH:32]1\"}",
"reactionStep": {
"id": "sa_9cc5430fa012da1d0783a3a8",
"reactionHash": "e3cb818b360dc7a38f96e9e4b1772cf2806b8b0427690bb01e87e6beacab462b"
},
"children": [
{
"id": "13458",
"routeId": "sa_25370d865fcc9b0f51fa29bf",
"moleculeId": "sa_57130bc252cfde81753623c1",
"parentId": "13457",
"isLeaf": true,
"molecule": {
"id": "sa_57130bc252cfde81753623c1",
"inchikey": "IRHKVRPOQMRDMU-UHFFFAOYSA-N",
"smiles": "COC(=O)c1ccc(-c2nc(Cl)ccc2C(N)=O)cc1"
},
"smiles": "COC(=O)c1ccc(-c2nc(Cl)ccc2C(N)=O)cc1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "13459",
"routeId": "sa_25370d865fcc9b0f51fa29bf",
"moleculeId": "sa_356dc388b0c8aecba726dc02",
"parentId": "13457",
"isLeaf": true,
"molecule": {
"id": "sa_356dc388b0c8aecba726dc02",
"inchikey": "VVDCRJGWILREQH-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)N1CC=C(B2OC(C)(C)C(C)(C)O2)CC1"
},
"smiles": "CC(C)(C)OC(=O)N1CC=C(B2OC(C)(C)C(C)(C)O2)CC1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
]
},
{
"id": "13460",
"routeId": "sa_25370d865fcc9b0f51fa29bf",
"moleculeId": "sa_257ba819b453f9a0e7fa3c07",
"parentId": "13454",
"isLeaf": true,
"molecule": {
"id": "sa_257ba819b453f9a0e7fa3c07",
"inchikey": "PAYRUJLWNCNPSJ-UHFFFAOYSA-N",
"smiles": "Nc1ccccc1"
},
"smiles": "Nc1ccccc1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
},
{
"id": "13461",
"routeId": "sa_25370d865fcc9b0f51fa29bf",
"moleculeId": "sa_0b4e45c0d9e46a5808f6bc17",
"parentId": "13452",
"isLeaf": true,
"molecule": {
"id": "sa_0b4e45c0d9e46a5808f6bc17",
"inchikey": "HFBMWMNUJJDEQZ-UHFFFAOYSA-N",
"smiles": "C=CC(=O)Cl"
},
"smiles": "C=CC(=O)Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
}