Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CN1Cc2cc(-c3ccc(C[C@H](NC(=O)C4(NC(=O)OC(C)(C)C)CCOCC4)C(N)=O)cc3)cnc2C1=O
InChiKey
BFOAVELYPVHHJT-NRFANRHFSA-N
Route Signature
dbdb870d0fb6a87a29dee64c6e867c050995dcb62adb195b45ced4574ebd2fa5
Synthesis route with 5 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_e48b8875328a651b843cba23",
"signature": "dbdb870d0fb6a87a29dee64c6e867c050995dcb62adb195b45ced4574ebd2fa5",
"contentHash": "1f44341d2e038502ac17771fded96abd8e33959826ddc4817e50ee7e347bd32a",
"length": 5,
"isConvergent": true
},
"target": {
"id": "sa_7351944bcadd3aa30da16e4e",
"benchmarkSetId": "7390a9c2522b1c81605e80a42a8de7c7ad9a5797d028633b54904bc78f091bb8",
"targetId": "n5-00189",
"moleculeId": "sa_3975ca9b19e1630c375af9b5",
"smiles": "CN1Cc2cc(-c3ccc(C[C@H](NC(=O)C4(NC(=O)OC(C)(C)C)CCOCC4)C(N)=O)cc3)cnc2C1=O",
"routeLength": 5,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_3975ca9b19e1630c375af9b5",
"inchikey": "BFOAVELYPVHHJT-NRFANRHFSA-N",
"smiles": "CN1Cc2cc(-c3ccc(C[C@H](NC(=O)C4(NC(=O)OC(C)(C)C)CCOCC4)C(N)=O)cc3)cnc2C1=O"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 3
},
"rootNode": {
"id": "316",
"routeId": "sa_e48b8875328a651b843cba23",
"moleculeId": "sa_3975ca9b19e1630c375af9b5",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_3975ca9b19e1630c375af9b5",
"inchikey": "BFOAVELYPVHHJT-NRFANRHFSA-N",
"smiles": "CN1Cc2cc(-c3ccc(C[C@H](NC(=O)C4(NC(=O)OC(C)(C)C)CCOCC4)C(N)=O)cc3)cnc2C1=O"
},
"smiles": "CN1Cc2cc(-c3ccc(C[C@H](NC(=O)C4(NC(=O)OC(C)(C)C)CCOCC4)C(N)=O)cc3)cnc2C1=O",
"reactionStepId": "sa_4e32df56c0010e522c3886b2",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20120329775A1;0589;1314804\",\"rsmi\":\"Br[c:6]1[cH:5][c:4]2[c:37]([n:36][cH:35]1)[C:38](=[O:39])[N:2]([CH3:1])[CH2:3]2.CC1(C)OB([c:7]2[cH:8][cH:9][c:10]([CH2:11][C@H:12]([NH:13][C:14](=[O:15])[C:16]3([NH:17][C:18](=[O:19])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])[CH2:25][CH2:26][O:27][CH2:28][CH2:29]3)[C:30]([NH2:31])=[O:32])[cH:33][cH:34]2)OC1(C)C>CC#N.O.O=C(O)O.[K+].[K+]>[CH3:1][N:2]1[CH2:3][c:4]2[cH:5][c:6](-[c:7]3[cH:8][cH:9][c:10]([CH2:11][C@H:12]([NH:13][C:14](=[O:15])[C:16]4([NH:17][C:18](=[O:19])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])[CH2:25][CH2:26][O:27][CH2:28][CH2:29]4)[C:30]([NH2:31])=[O:32])[cH:33][cH:34]3)[cH:35][n:36][c:37]2[C:38]1=[O:39]\"},\"mapped_reaction_smiles\":\"Br[c:6]1[cH:5][c:4]2[c:37]([n:36][cH:35]1)[C:38](=[O:39])[N:2]([CH3:1])[CH2:3]2.CC1(C)OB([c:7]2[cH:8][cH:9][c:10]([CH2:11][C@H:12]([NH:13][C:14](=[O:15])[C:16]3([NH:17][C:18](=[O:19])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])[CH2:25][CH2:26][O:27][CH2:28][CH2:29]3)[C:30]([NH2:31])=[O:32])[cH:33][cH:34]2)OC1(C)C>CC#N.O.O=C(O)O.[K+].[K+]>[CH3:1][N:2]1[CH2:3][c:4]2[cH:5][c:6](-[c:7]3[cH:8][cH:9][c:10]([CH2:11][C@H:12]([NH:13][C:14](=[O:15])[C:16]4([NH:17][C:18](=[O:19])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])[CH2:25][CH2:26][O:27][CH2:28][CH2:29]4)[C:30]([NH2:31])=[O:32])[cH:33][cH:34]3)[cH:35][n:36][c:37]2[C:38]1=[O:39]\"}",
"reactionStep": {
"id": "sa_4e32df56c0010e522c3886b2",
"reactionHash": "0751bc59557b57f80802195b8a802de1bea0c30d2519546f0ebb2bafad7929fb"
},
"children": [
{
"id": "317",
"routeId": "sa_e48b8875328a651b843cba23",
"moleculeId": "sa_d698d35e9caacada93a38cb3",
"parentId": "316",
"isLeaf": false,
"molecule": {
"id": "sa_d698d35e9caacada93a38cb3",
"inchikey": "BIAJIZVBOQVDTC-UHFFFAOYSA-N",
"smiles": "CN1Cc2cc(Br)cnc2C1=O"
},
"smiles": "CN1Cc2cc(Br)cnc2C1=O",
"reactionStepId": "sa_f67b25772e83f43e7b0ab220",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20120329775A1;0585;1314803\",\"rsmi\":\"CO[C:11]([c:10]1[c:4]([CH2:3]Br)[cH:5][c:6]([Br:7])[cH:8][n:9]1)=[O:12].[CH3:1][NH2:2]>C1CCOC1>[CH3:1][N:2]1[CH2:3][c:4]2[cH:5][c:6]([Br:7])[cH:8][n:9][c:10]2[C:11]1=[O:12]\"},\"mapped_reaction_smiles\":\"CO[C:11]([c:10]1[c:4]([CH2:3]Br)[cH:5][c:6]([Br:7])[cH:8][n:9]1)=[O:12].[CH3:1][NH2:2]>C1CCOC1>[CH3:1][N:2]1[CH2:3][c:4]2[cH:5][c:6]([Br:7])[cH:8][n:9][c:10]2[C:11]1=[O:12]\"}",
"reactionStep": {
"id": "sa_f67b25772e83f43e7b0ab220",
"reactionHash": "4c09e82c24efd99bdb904d82407859248b62dfbd2e7eccae76b3ca8325f6b32b"
},
"children": [
{
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"routeId": "sa_e48b8875328a651b843cba23",
"moleculeId": "sa_e00cdbb7fb9d3ecf114a19d3",
"parentId": "317",
"isLeaf": true,
"molecule": {
"id": "sa_e00cdbb7fb9d3ecf114a19d3",
"inchikey": "BAVYZALUXZFZLV-UHFFFAOYSA-N",
"smiles": "CN"
},
"smiles": "CN",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "319",
"routeId": "sa_e48b8875328a651b843cba23",
"moleculeId": "sa_b4b5ce784cce4198ae825a88",
"parentId": "317",
"isLeaf": false,
"molecule": {
"id": "sa_b4b5ce784cce4198ae825a88",
"inchikey": "CPWMCAMLRLHDAT-UHFFFAOYSA-N",
"smiles": "COC(=O)c1ncc(Br)cc1CBr"
},
"smiles": "COC(=O)c1ncc(Br)cc1CBr",
"reactionStepId": "sa_9d1ab7eb42771fc554280399",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20120329775A1;0582;1314802\",\"rsmi\":\"O=C1CCC(=O)N1[Br:13].[CH3:1][O:2][C:3](=[O:4])[c:5]1[n:6][cH:7][c:8]([Br:9])[cH:10][c:11]1[CH3:12]>CC(C)(C#N)N=NC(C)(C)C#N.ClCCl>[CH3:1][O:2][C:3](=[O:4])[c:5]1[n:6][cH:7][c:8]([Br:9])[cH:10][c:11]1[CH2:12][Br:13]\"},\"mapped_reaction_smiles\":\"O=C1CCC(=O)N1[Br:13].[CH3:1][O:2][C:3](=[O:4])[c:5]1[n:6][cH:7][c:8]([Br:9])[cH:10][c:11]1[CH3:12]>CC(C)(C#N)N=NC(C)(C)C#N.ClCCl>[CH3:1][O:2][C:3](=[O:4])[c:5]1[n:6][cH:7][c:8]([Br:9])[cH:10][c:11]1[CH2:12][Br:13]\"}",
"reactionStep": {
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"reactionHash": "1cf517958bc28168a703d3fb302febc49dacb1dfaf9194f582db76da87d5e6d0"
},
"children": [
{
"id": "320",
"routeId": "sa_e48b8875328a651b843cba23",
"moleculeId": "sa_e6171319c63bccd1fe689120",
"parentId": "319",
"isLeaf": true,
"molecule": {
"id": "sa_e6171319c63bccd1fe689120",
"inchikey": "KZPOANNAYCXMSH-UHFFFAOYSA-N",
"smiles": "COC(=O)c1ncc(Br)cc1C"
},
"smiles": "COC(=O)c1ncc(Br)cc1C",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "321",
"routeId": "sa_e48b8875328a651b843cba23",
"moleculeId": "sa_ccdcf23ac83e7a68bfa4f2e5",
"parentId": "319",
"isLeaf": true,
"molecule": {
"id": "sa_ccdcf23ac83e7a68bfa4f2e5",
"inchikey": "PCLIMKBDDGJMGD-UHFFFAOYSA-N",
"smiles": "O=C1CCC(=O)N1Br"
},
"smiles": "O=C1CCC(=O)N1Br",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
},
{
"id": "322",
"routeId": "sa_e48b8875328a651b843cba23",
"moleculeId": "sa_a209c54baf72471be76f31d0",
"parentId": "316",
"isLeaf": false,
"molecule": {
"id": "sa_a209c54baf72471be76f31d0",
"inchikey": "QPADCMLLFLILNL-IBGZPJMESA-N",
"smiles": "CC(C)(C)OC(=O)NC1(C(=O)N[C@@H](Cc2ccc(B3OC(C)(C)C(C)(C)O3)cc2)C(N)=O)CCOCC1"
},
"smiles": "CC(C)(C)OC(=O)NC1(C(=O)N[C@@H](Cc2ccc(B3OC(C)(C)C(C)(C)O3)cc2)C(N)=O)CCOCC1",
"reactionStepId": "sa_33c1447da23e84afa80cba80",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20120329775A1;0412;1314762\",\"rsmi\":\"CC1(C)OB([B:19]2[O:20][C:21]([CH3:22])([CH3:23])[C:24]([CH3:25])([CH3:26])[O:27]2)OC1(C)C.I[c:18]1[cH:17][cH:16][c:15]([CH2:14][C@H:13]([NH:12][C:10]([C:9]2([NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:33][CH2:34][O:35][CH2:36][CH2:37]2)=[O:11])[C:30]([NH2:31])=[O:32])[cH:29][cH:28]1>CC#N.CC(=O)O.O.[K+]>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C:9]1([C:10](=[O:11])[NH:12][C@@H:13]([CH2:14][c:15]2[cH:16][cH:17][c:18]([B:19]3[O:20][C:21]([CH3:22])([CH3:23])[C:24]([CH3:25])([CH3:26])[O:27]3)[cH:28][cH:29]2)[C:30]([NH2:31])=[O:32])[CH2:33][CH2:34][O:35][CH2:36][CH2:37]1\"},\"mapped_reaction_smiles\":\"CC1(C)OB([B:19]2[O:20][C:21]([CH3:22])([CH3:23])[C:24]([CH3:25])([CH3:26])[O:27]2)OC1(C)C.I[c:18]1[cH:17][cH:16][c:15]([CH2:14][C@H:13]([NH:12][C:10]([C:9]2([NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:33][CH2:34][O:35][CH2:36][CH2:37]2)=[O:11])[C:30]([NH2:31])=[O:32])[cH:29][cH:28]1>CC#N.CC(=O)O.O.[K+]>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C:9]1([C:10](=[O:11])[NH:12][C@@H:13]([CH2:14][c:15]2[cH:16][cH:17][c:18]([B:19]3[O:20][C:21]([CH3:22])([CH3:23])[C:24]([CH3:25])([CH3:26])[O:27]3)[cH:28][cH:29]2)[C:30]([NH2:31])=[O:32])[CH2:33][CH2:34][O:35][CH2:36][CH2:37]1\"}",
"reactionStep": {
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"reactionHash": "e118a74fe747ce2feb6ef513d2c80647c8a27ea1cc445649d1395dbec2567df1"
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"children": [
{
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"routeId": "sa_e48b8875328a651b843cba23",
"moleculeId": "sa_003aaac270ce0d23213e8837",
"parentId": "322",
"isLeaf": false,
"molecule": {
"id": "sa_003aaac270ce0d23213e8837",
"inchikey": "GHNNPRUUZNXUGI-HNNXBMFYSA-N",
"smiles": "CC(C)(C)OC(=O)NC1(C(=O)N[C@@H](Cc2ccc(I)cc2)C(N)=O)CCOCC1"
},
"smiles": "CC(C)(C)OC(=O)NC1(C(=O)N[C@@H](Cc2ccc(I)cc2)C(N)=O)CCOCC1",
"reactionStepId": "sa_146b1254da96e5fbc7c4f647",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20120329775A1;0237;1314721\",\"rsmi\":\"O[C:10]([C:9]1([NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:25][CH2:26][O:27][CH2:28][CH2:29]1)=[O:11].[NH2:12][C@@H:13]([CH2:14][c:15]1[cH:16][cH:17][c:18]([I:19])[cH:20][cH:21]1)[C:22]([NH2:23])=[O:24]>CCN(C(C)C)C(C)C.CN(C)C(On1nnc2ccccc21)=[N+](C)C.CN(C)C=O.F[B-](F)(F)F>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C:9]1([C:10](=[O:11])[NH:12][C@@H:13]([CH2:14][c:15]2[cH:16][cH:17][c:18]([I:19])[cH:20][cH:21]2)[C:22]([NH2:23])=[O:24])[CH2:25][CH2:26][O:27][CH2:28][CH2:29]1\"},\"mapped_reaction_smiles\":\"O[C:10]([C:9]1([NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:25][CH2:26][O:27][CH2:28][CH2:29]1)=[O:11].[NH2:12][C@@H:13]([CH2:14][c:15]1[cH:16][cH:17][c:18]([I:19])[cH:20][cH:21]1)[C:22]([NH2:23])=[O:24]>CCN(C(C)C)C(C)C.CN(C)C(On1nnc2ccccc21)=[N+](C)C.CN(C)C=O.F[B-](F)(F)F>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C:9]1([C:10](=[O:11])[NH:12][C@@H:13]([CH2:14][c:15]2[cH:16][cH:17][c:18]([I:19])[cH:20][cH:21]2)[C:22]([NH2:23])=[O:24])[CH2:25][CH2:26][O:27][CH2:28][CH2:29]1\"}",
"reactionStep": {
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"children": [
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"molecule": {
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"smiles": "NC(=O)[C@@H](N)Cc1ccc(I)cc1",
"reactionStepId": "sa_4dd38a695d2fcd158d90f7fd",
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"metadata": "{\"annotations\":{\"ID\":\"US20120329775A1;0233;1314720\",\"rsmi\":\"CC(C)(C)OC(=O)[NH:5][C@H:4]([C:2]([NH2:1])=[O:3])[CH2:6][c:7]1[cH:8][cH:9][c:10]([I:11])[cH:12][cH:13]1>ClCCl.O=C(O)C(F)(F)F>[NH2:1][C:2](=[O:3])[C@@H:4]([NH2:5])[CH2:6][c:7]1[cH:8][cH:9][c:10]([I:11])[cH:12][cH:13]1\"},\"mapped_reaction_smiles\":\"CC(C)(C)OC(=O)[NH:5][C@H:4]([C:2]([NH2:1])=[O:3])[CH2:6][c:7]1[cH:8][cH:9][c:10]([I:11])[cH:12][cH:13]1>ClCCl.O=C(O)C(F)(F)F>[NH2:1][C:2](=[O:3])[C@@H:4]([NH2:5])[CH2:6][c:7]1[cH:8][cH:9][c:10]([I:11])[cH:12][cH:13]1\"}",
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"reactionStepId": "sa_7f6dc72a9d97d2d738309ae5",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20120329775A1;0230;1314719\",\"rsmi\":\"O[C:18]([C@@H:9]([NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:10][c:11]1[cH:12][cH:13][c:14]([I:15])[cH:16][cH:17]1)=[O:20].[NH3:19]>CCN1CCOCC1.CN(C)C(On1nnc2ccccc21)=[N+](C)C.CN(C)C=O.F[B-](F)(F)F.O>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C@@H:9]([CH2:10][c:11]1[cH:12][cH:13][c:14]([I:15])[cH:16][cH:17]1)[C:18]([NH2:19])=[O:20]\"},\"mapped_reaction_smiles\":\"O[C:18]([C@@H:9]([NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:10][c:11]1[cH:12][cH:13][c:14]([I:15])[cH:16][cH:17]1)=[O:20].[NH3:19]>CCN1CCOCC1.CN(C)C(On1nnc2ccccc21)=[N+](C)C.CN(C)C=O.F[B-](F)(F)F.O>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C@@H:9]([CH2:10][c:11]1[cH:12][cH:13][c:14]([I:15])[cH:16][cH:17]1)[C:18]([NH2:19])=[O:20]\"}",
"reactionStep": {
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