Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CCOC(=O)c1sc(N2CC[C@@H](NC(=O)c3nc(Cl)c(CC)[nH]3)[C@H](N)C2)nc1C
InChiKey
FMEGPCLKZSCHCJ-ZYHUDNBSSA-N
Route Signature
55892b01de012dd9fed9e304f8cac386e762aa3cc6d5761652c40b121c5c90bc
Synthesis route with 5 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_95f4b8df9546610154afa3b5",
"signature": "55892b01de012dd9fed9e304f8cac386e762aa3cc6d5761652c40b121c5c90bc",
"contentHash": "cba72b4197d5bb3742d772ebc8f94452b843677e99cb7e1da40b0db20e8e0192",
"length": 5,
"isConvergent": true
},
"target": {
"id": "sa_46b0267120ac8a864b1c1173",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-00734",
"moleculeId": "sa_a60e10ee166c5277d12c57c9",
"smiles": "CCOC(=O)c1sc(N2CC[C@@H](NC(=O)c3nc(Cl)c(CC)[nH]3)[C@H](N)C2)nc1C",
"routeLength": 5,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_a60e10ee166c5277d12c57c9",
"inchikey": "FMEGPCLKZSCHCJ-ZYHUDNBSSA-N",
"smiles": "CCOC(=O)c1sc(N2CC[C@@H](NC(=O)c3nc(Cl)c(CC)[nH]3)[C@H](N)C2)nc1C"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "9716",
"routeId": "sa_95f4b8df9546610154afa3b5",
"moleculeId": "sa_a60e10ee166c5277d12c57c9",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_a60e10ee166c5277d12c57c9",
"inchikey": "FMEGPCLKZSCHCJ-ZYHUDNBSSA-N",
"smiles": "CCOC(=O)c1sc(N2CC[C@@H](NC(=O)c3nc(Cl)c(CC)[nH]3)[C@H](N)C2)nc1C"
},
"smiles": "CCOC(=O)c1sc(N2CC[C@@H](NC(=O)c3nc(Cl)c(CC)[nH]3)[C@H](N)C2)nc1C",
"reactionStepId": "sa_597168c4e2ce726f975a7290",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08927588B2;1002;1564866\",\"rsmi\":\"O=C(OCc1ccccc1)[NH:27][C@H:26]1[C@H:14]([NH:15][C:16](=[O:17])[c:18]2[n:19][c:20]([Cl:21])[c:22]([CH2:23][CH3:24])[nH:25]2)[CH2:13][CH2:12][N:11]([c:10]2[n:9][c:7]([CH3:8])[c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[s:29]2)[CH2:28]1>Br.CC(=O)O.Cc1ncsc1C(=O)O.O=C(O)O.[Na+]>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7]([CH3:8])[n:9][c:10]([N:11]2[CH2:12][CH2:13][C@@H:14]([NH:15][C:16](=[O:17])[c:18]3[n:19][c:20]([Cl:21])[c:22]([CH2:23][CH3:24])[nH:25]3)[C@H:26]([NH2:27])[CH2:28]2)[s:29]1\"},\"mapped_reaction_smiles\":\"O=C(OCc1ccccc1)[NH:27][C@H:26]1[C@H:14]([NH:15][C:16](=[O:17])[c:18]2[n:19][c:20]([Cl:21])[c:22]([CH2:23][CH3:24])[nH:25]2)[CH2:13][CH2:12][N:11]([c:10]2[n:9][c:7]([CH3:8])[c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[s:29]2)[CH2:28]1>Br.CC(=O)O.Cc1ncsc1C(=O)O.O=C(O)O.[Na+]>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7]([CH3:8])[n:9][c:10]([N:11]2[CH2:12][CH2:13][C@@H:14]([NH:15][C:16](=[O:17])[c:18]3[n:19][c:20]([Cl:21])[c:22]([CH2:23][CH3:24])[nH:25]3)[C@H:26]([NH2:27])[CH2:28]2)[s:29]1\"}",
"reactionStep": {
"id": "sa_597168c4e2ce726f975a7290",
"reactionHash": "f0fd681fe70c125376c7dedd7f2bd7c6083fcda5ba0cfb146bba961278a9ee54"
},
"children": [
{
"id": "9717",
"routeId": "sa_95f4b8df9546610154afa3b5",
"moleculeId": "sa_6c831587d32700f53cba9cd0",
"parentId": "9716",
"isLeaf": false,
"molecule": {
"id": "sa_6c831587d32700f53cba9cd0",
"inchikey": "DVSHRAXNBIAJDB-RTBURBONSA-N",
"smiles": "CCOC(=O)c1sc(N2CC[C@@H](NC(=O)c3nc(Cl)c(CC)[nH]3)[C@H](NC(=O)OCc3ccccc3)C2)nc1C"
},
"smiles": "CCOC(=O)c1sc(N2CC[C@@H](NC(=O)c3nc(Cl)c(CC)[nH]3)[C@H](NC(=O)OCc3ccccc3)C2)nc1C",
"reactionStepId": "sa_3a5817ad0c602addd540c8f1",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08927588B2;0996;1564865\",\"rsmi\":\"Br[c:10]1[n:9][c:7]([CH3:8])[c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[s:39]1.CC(C)(C)OC(=O)[N:11]1[CH2:12][CH2:13][C@@H:14]([NH:15][C:16](=[O:17])[c:18]2[n:19][c:20]([Cl:21])[c:22]([CH2:23][CH3:24])[nH:25]2)[C@H:26]([NH:27][C:28](=[O:29])[O:30][CH2:31][c:32]2[cH:33][cH:34][cH:35][cH:36][cH:37]2)[CH2:38]1>O=C(O)O.[Na+].[Na+]>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7]([CH3:8])[n:9][c:10]([N:11]2[CH2:12][CH2:13][C@@H:14]([NH:15][C:16](=[O:17])[c:18]3[n:19][c:20]([Cl:21])[c:22]([CH2:23][CH3:24])[nH:25]3)[C@H:26]([NH:27][C:28](=[O:29])[O:30][CH2:31][c:32]3[cH:33][cH:34][cH:35][cH:36][cH:37]3)[CH2:38]2)[s:39]1\"},\"mapped_reaction_smiles\":\"Br[c:10]1[n:9][c:7]([CH3:8])[c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[s:39]1.CC(C)(C)OC(=O)[N:11]1[CH2:12][CH2:13][C@@H:14]([NH:15][C:16](=[O:17])[c:18]2[n:19][c:20]([Cl:21])[c:22]([CH2:23][CH3:24])[nH:25]2)[C@H:26]([NH:27][C:28](=[O:29])[O:30][CH2:31][c:32]2[cH:33][cH:34][cH:35][cH:36][cH:37]2)[CH2:38]1>O=C(O)O.[Na+].[Na+]>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7]([CH3:8])[n:9][c:10]([N:11]2[CH2:12][CH2:13][C@@H:14]([NH:15][C:16](=[O:17])[c:18]3[n:19][c:20]([Cl:21])[c:22]([CH2:23][CH3:24])[nH:25]3)[C@H:26]([NH:27][C:28](=[O:29])[O:30][CH2:31][c:32]3[cH:33][cH:34][cH:35][cH:36][cH:37]3)[CH2:38]2)[s:39]1\"}",
"reactionStep": {
"id": "sa_3a5817ad0c602addd540c8f1",
"reactionHash": "6da917570fafc34862ef4f25fb3478086e3a0c8f4bb2cd234fca22cd8f9c21d4"
},
"children": [
{
"id": "9718",
"routeId": "sa_95f4b8df9546610154afa3b5",
"moleculeId": "sa_4b9da5a78605e2a143631a3e",
"parentId": "9717",
"isLeaf": true,
"molecule": {
"id": "sa_4b9da5a78605e2a143631a3e",
"inchikey": "CFBIOWPDDZPIDP-UHFFFAOYSA-N",
"smiles": "CCOC(=O)c1sc(Br)nc1C"
},
"smiles": "CCOC(=O)c1sc(Br)nc1C",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "9719",
"routeId": "sa_95f4b8df9546610154afa3b5",
"moleculeId": "sa_c2a75d46a116768fd4b7b830",
"parentId": "9717",
"isLeaf": false,
"molecule": {
"id": "sa_c2a75d46a116768fd4b7b830",
"inchikey": "GWNGZXXQEQYGIO-QZTJIDSGSA-N",
"smiles": "CCc1[nH]c(C(=O)N[C@@H]2CCN(C(=O)OC(C)(C)C)C[C@H]2NC(=O)OCc2ccccc2)nc1Cl"
},
"smiles": "CCc1[nH]c(C(=O)N[C@@H]2CCN(C(=O)OC(C)(C)C)C[C@H]2NC(=O)OCc2ccccc2)nc1Cl",
"reactionStepId": "sa_8b275aa1a72e4ff1fe2a5c2a",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08927588B2;0994;1564864\",\"rsmi\":\"O[C:8]([c:7]1[n:6][c:4]([Cl:5])[c:3]([CH2:2][CH3:1])[nH:35]1)=[O:9].[NH2:10][C@@H:11]1[CH2:12][CH2:13][N:14]([C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21])[CH2:22][C@H:23]1[NH:24][C:25](=[O:26])[O:27][CH2:28][c:29]1[cH:30][cH:31][cH:32][cH:33][cH:34]1>CCN=C=NCCCN(C)C.Cl.On1nnc2ccccc21>[CH3:1][CH2:2][c:3]1[c:4]([Cl:5])[n:6][c:7]([C:8](=[O:9])[NH:10][C@@H:11]2[CH2:12][CH2:13][N:14]([C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21])[CH2:22][C@H:23]2[NH:24][C:25](=[O:26])[O:27][CH2:28][c:29]2[cH:30][cH:31][cH:32][cH:33][cH:34]2)[nH:35]1\"},\"mapped_reaction_smiles\":\"O[C:8]([c:7]1[n:6][c:4]([Cl:5])[c:3]([CH2:2][CH3:1])[nH:35]1)=[O:9].[NH2:10][C@@H:11]1[CH2:12][CH2:13][N:14]([C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21])[CH2:22][C@H:23]1[NH:24][C:25](=[O:26])[O:27][CH2:28][c:29]1[cH:30][cH:31][cH:32][cH:33][cH:34]1>CCN=C=NCCCN(C)C.Cl.On1nnc2ccccc21>[CH3:1][CH2:2][c:3]1[c:4]([Cl:5])[n:6][c:7]([C:8](=[O:9])[NH:10][C@@H:11]2[CH2:12][CH2:13][N:14]([C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21])[CH2:22][C@H:23]2[NH:24][C:25](=[O:26])[O:27][CH2:28][c:29]2[cH:30][cH:31][cH:32][cH:33][cH:34]2)[nH:35]1\"}",
"reactionStep": {
"id": "sa_8b275aa1a72e4ff1fe2a5c2a",
"reactionHash": "f0bcca0c42cafaf76447ff173484bfce340dda6903d15434c5282afab14f19c2"
},
"children": [
{
"id": "9720",
"routeId": "sa_95f4b8df9546610154afa3b5",
"moleculeId": "sa_834208f454826d7c84e9d55c",
"parentId": "9719",
"isLeaf": false,
"molecule": {
"id": "sa_834208f454826d7c84e9d55c",
"inchikey": "DMTGNUNYYRIFOC-HUUCEWRRSA-N",
"smiles": "CC(C)(C)OC(=O)N1CC[C@@H](N)[C@H](NC(=O)OCc2ccccc2)C1"
},
"smiles": "CC(C)(C)OC(=O)N1CC[C@@H](N)[C@H](NC(=O)OCc2ccccc2)C1",
"reactionStepId": "sa_e198eaa7c2dae627c5caebfc",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08927588B2;0993;1564863\",\"rsmi\":\"[N-]=[N+]=[N:12][C@@H:11]1[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:25][C@H:13]1[NH:14][C:15](=[O:16])[O:17][CH2:18][c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1>C1CCOC1.CO.Cl[Ni]Cl.O.O.O=C(O)O.B.[Na+].[Na+]>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][C@@H:11]([NH2:12])[C@H:13]([NH:14][C:15](=[O:16])[O:17][CH2:18][c:19]2[cH:20][cH:21][cH:22][cH:23][cH:24]2)[CH2:25]1\"},\"mapped_reaction_smiles\":\"[N-]=[N+]=[N:12][C@@H:11]1[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:25][C@H:13]1[NH:14][C:15](=[O:16])[O:17][CH2:18][c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1>C1CCOC1.CO.Cl[Ni]Cl.O.O.O=C(O)O.B.[Na+].[Na+]>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][C@@H:11]([NH2:12])[C@H:13]([NH:14][C:15](=[O:16])[O:17][CH2:18][c:19]2[cH:20][cH:21][cH:22][cH:23][cH:24]2)[CH2:25]1\"}",
"reactionStep": {
"id": "sa_e198eaa7c2dae627c5caebfc",
"reactionHash": "926e6ecbd92a375c1e8b19a6a8242accd224338ea45d0ebb43e42245d23de761"
},
"children": [
{
"id": "9721",
"routeId": "sa_95f4b8df9546610154afa3b5",
"moleculeId": "sa_1b447e19aca17021d5ed7796",
"parentId": "9720",
"isLeaf": true,
"molecule": {
"id": "sa_1b447e19aca17021d5ed7796",
"inchikey": "MTDMXKUAYZWFGP-HUUCEWRRSA-N",
"smiles": "CC(C)(C)OC(=O)N1CC[C@@H](N=[N+]=[N-])[C@H](NC(=O)OCc2ccccc2)C1"
},
"smiles": "CC(C)(C)OC(=O)N1CC[C@@H](N=[N+]=[N-])[C@H](NC(=O)OCc2ccccc2)C1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "9722",
"routeId": "sa_95f4b8df9546610154afa3b5",
"moleculeId": "sa_9bc8b08abdf7525102dd4467",
"parentId": "9719",
"isLeaf": false,
"molecule": {
"id": "sa_9bc8b08abdf7525102dd4467",
"inchikey": "WBRFPIVOPOBICF-UHFFFAOYSA-N",
"smiles": "CCc1[nH]c(C(=O)O)nc1Cl"
},
"smiles": "CCc1[nH]c(C(=O)O)nc1Cl",
"reactionStepId": "sa_f145be2dbb2bb8ad8b26d359",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08927588B2;0267;1564753\",\"rsmi\":\"CC[O:10][C:8]([c:7]1[n:6][c:4]([Cl:5])[c:3]([CH2:2][CH3:1])[nH:11]1)=[O:9]>CO.ClCCl.[Li+].O>[CH3:1][CH2:2][c:3]1[c:4]([Cl:5])[n:6][c:7]([C:8](=[O:9])[OH:10])[nH:11]1\"},\"mapped_reaction_smiles\":\"CC[O:10][C:8]([c:7]1[n:6][c:4]([Cl:5])[c:3]([CH2:2][CH3:1])[nH:11]1)=[O:9]>CO.ClCCl.[Li+].O>[CH3:1][CH2:2][c:3]1[c:4]([Cl:5])[n:6][c:7]([C:8](=[O:9])[OH:10])[nH:11]1\"}",
"reactionStep": {
"id": "sa_f145be2dbb2bb8ad8b26d359",
"reactionHash": "17bf90cc2e29a1b93adad9c3beb9855c8d9b28d5e254875cc053de9bb17da259"
},
"children": [
{
"id": "9723",
"routeId": "sa_95f4b8df9546610154afa3b5",
"moleculeId": "sa_0ffae542729eb49e4bfd3649",
"parentId": "9722",
"isLeaf": false,
"molecule": {
"id": "sa_0ffae542729eb49e4bfd3649",
"inchikey": "KNQZWWOAZXSMTG-UHFFFAOYSA-N",
"smiles": "CCOC(=O)c1nc(Cl)c(CC)[nH]1"
},
"smiles": "CCOC(=O)c1nc(Cl)c(CC)[nH]1",
"reactionStepId": "sa_9add913b41fde2dc06ad7c95",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08927588B2;0265;1564752\",\"rsmi\":\"O=C1CCC(=O)N1[Cl:9].[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[n:7][cH:8][c:10]([CH2:11][CH3:12])[nH:13]1>ClC(Cl)Cl.O=C(O)O.[Na+]>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[n:7][c:8]([Cl:9])[c:10]([CH2:11][CH3:12])[nH:13]1\"},\"mapped_reaction_smiles\":\"O=C1CCC(=O)N1[Cl:9].[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[n:7][cH:8][c:10]([CH2:11][CH3:12])[nH:13]1>ClC(Cl)Cl.O=C(O)O.[Na+]>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[n:7][c:8]([Cl:9])[c:10]([CH2:11][CH3:12])[nH:13]1\"}",
"reactionStep": {
"id": "sa_9add913b41fde2dc06ad7c95",
"reactionHash": "8ac4f168cb7d53155176d18af2cdf84b0660857106b9bf17ae887dbbc6f00fa8"
},
"children": [
{
"id": "9724",
"routeId": "sa_95f4b8df9546610154afa3b5",
"moleculeId": "sa_a576f9b9a2caa305053d217d",
"parentId": "9723",
"isLeaf": true,
"molecule": {
"id": "sa_a576f9b9a2caa305053d217d",
"inchikey": "JRNVZBWKYDBUCA-UHFFFAOYSA-N",
"smiles": "O=C1CCC(=O)N1Cl"
},
"smiles": "O=C1CCC(=O)N1Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "9725",
"routeId": "sa_95f4b8df9546610154afa3b5",
"moleculeId": "sa_249834358f82e299278170ed",
"parentId": "9723",
"isLeaf": true,
"molecule": {
"id": "sa_249834358f82e299278170ed",
"inchikey": "QFBQZDDWPFZPSS-UHFFFAOYSA-N",
"smiles": "CCOC(=O)c1ncc(CC)[nH]1"
},
"smiles": "CCOC(=O)c1ncc(CC)[nH]1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
]
}
]
}
]
}
}