Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CNC(=O)[C@H](CC(C)C)NC(=O)c1nc(Br)n2c1CN(C(=O)OC(C)(C)C)CC2
InChiKey
RNRILIZUNNCZEP-LBPRGKRZSA-N
Route Signature
a724dcf6ca8f945db499ae32542decea6e35a0b4b49727072374db4a6c220e43
Synthesis route with 4 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_2c3e7c7cf2f32a5d88f65c6d",
"signature": "a724dcf6ca8f945db499ae32542decea6e35a0b4b49727072374db4a6c220e43",
"contentHash": "246d722b623a0cea32f9cb240bfa3dddbff1dcaf1f81c5047ba8cccbac55fcf9",
"length": 4,
"isConvergent": true
},
"target": {
"id": "sa_f3ed68b971e408bf1ee7d15d",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-02169",
"moleculeId": "sa_d7040ab077de954dd281da61",
"smiles": "CNC(=O)[C@H](CC(C)C)NC(=O)c1nc(Br)n2c1CN(C(=O)OC(C)(C)C)CC2",
"routeLength": 4,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_d7040ab077de954dd281da61",
"inchikey": "RNRILIZUNNCZEP-LBPRGKRZSA-N",
"smiles": "CNC(=O)[C@H](CC(C)C)NC(=O)c1nc(Br)n2c1CN(C(=O)OC(C)(C)C)CC2"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "10655",
"routeId": "sa_2c3e7c7cf2f32a5d88f65c6d",
"moleculeId": "sa_d7040ab077de954dd281da61",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_d7040ab077de954dd281da61",
"inchikey": "RNRILIZUNNCZEP-LBPRGKRZSA-N",
"smiles": "CNC(=O)[C@H](CC(C)C)NC(=O)c1nc(Br)n2c1CN(C(=O)OC(C)(C)C)CC2"
},
"smiles": "CNC(=O)[C@H](CC(C)C)NC(=O)c1nc(Br)n2c1CN(C(=O)OC(C)(C)C)CC2",
"reactionStepId": "sa_629837302c2bd9745b285962",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20110034443A1;0200;1011119\",\"rsmi\":\"O[C:11](=[O:12])[c:13]1[c:14]2[n:26]([c:27]([Br:28])[n:29]1)[CH2:25][CH2:24][N:16]([C:17](=[O:18])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23])[CH2:15]2.[CH3:1][NH:2][C:3](=[O:4])[C@H:5]([CH2:6][CH:7]([CH3:8])[CH3:9])[NH2:10]>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][NH:2][C:3](=[O:4])[C@H:5]([CH2:6][CH:7]([CH3:8])[CH3:9])[NH:10][C:11](=[O:12])[c:13]1[c:14]2[n:26]([c:27]([Br:28])[n:29]1)[CH2:25][CH2:24][N:16]([C:17](=[O:18])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23])[CH2:15]2\"},\"mapped_reaction_smiles\":\"O[C:11](=[O:12])[c:13]1[c:14]2[n:26]([c:27]([Br:28])[n:29]1)[CH2:25][CH2:24][N:16]([C:17](=[O:18])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23])[CH2:15]2.[CH3:1][NH:2][C:3](=[O:4])[C@H:5]([CH2:6][CH:7]([CH3:8])[CH3:9])[NH2:10]>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][NH:2][C:3](=[O:4])[C@H:5]([CH2:6][CH:7]([CH3:8])[CH3:9])[NH:10][C:11](=[O:12])[c:13]1[c:14]2[n:26]([c:27]([Br:28])[n:29]1)[CH2:25][CH2:24][N:16]([C:17](=[O:18])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23])[CH2:15]2\"}",
"reactionStep": {
"id": "sa_629837302c2bd9745b285962",
"reactionHash": "289472d6c015c0ee956e2d2946d5b811d157aea565d941503fc524edd4a03fbb"
},
"children": [
{
"id": "10656",
"routeId": "sa_2c3e7c7cf2f32a5d88f65c6d",
"moleculeId": "sa_7a165c941bffde42f9796f08",
"parentId": "10655",
"isLeaf": false,
"molecule": {
"id": "sa_7a165c941bffde42f9796f08",
"inchikey": "LIBDTAYIDBPBRN-LURJTMIESA-N",
"smiles": "CNC(=O)[C@@H](N)CC(C)C"
},
"smiles": "CNC(=O)[C@@H](N)CC(C)C",
"reactionStepId": "sa_8bfb3e980ea0f463510e7ab2",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20110034443A1;0199;1011118\",\"rsmi\":\"O=C(OCc1ccccc1)[NH:6][C@H:5]([C:3]([NH:2][CH3:1])=[O:4])[CH2:7][CH:8]([CH3:9])[CH3:10]>CO.[H][H].[Pd]>[CH3:1][NH:2][C:3](=[O:4])[C@@H:5]([NH2:6])[CH2:7][CH:8]([CH3:9])[CH3:10]\"},\"mapped_reaction_smiles\":\"O=C(OCc1ccccc1)[NH:6][C@H:5]([C:3]([NH:2][CH3:1])=[O:4])[CH2:7][CH:8]([CH3:9])[CH3:10]>CO.[H][H].[Pd]>[CH3:1][NH:2][C:3](=[O:4])[C@@H:5]([NH2:6])[CH2:7][CH:8]([CH3:9])[CH3:10]\"}",
"reactionStep": {
"id": "sa_8bfb3e980ea0f463510e7ab2",
"reactionHash": "f38835b72f82395cc8046569b0a60ac7b0b390a06552f9e916fe0aa42548abda"
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"children": [
{
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"moleculeId": "sa_4862ebfd908c4f33ca52be34",
"parentId": "10656",
"isLeaf": false,
"molecule": {
"id": "sa_4862ebfd908c4f33ca52be34",
"inchikey": "UOBCOWPMCMJUMK-ZDUSSCGKSA-N",
"smiles": "CNC(=O)[C@H](CC(C)C)NC(=O)OCc1ccccc1"
},
"smiles": "CNC(=O)[C@H](CC(C)C)NC(=O)OCc1ccccc1",
"reactionStepId": "sa_3617423b81877772fac2271f",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20110034443A1;0198;1011117\",\"rsmi\":\"O[C:3](=[O:4])[C@H:5]([CH2:6][CH:7]([CH3:8])[CH3:9])[NH:10][C:11](=[O:12])[O:13][CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1.[CH3:1][NH2:2]>CCN(C(C)C)C(C)C.CN(C)C(On1nnc2ccccc21)=[N+](C)C.CN(C)C=O.Cl.F[B-](F)(F)F>[CH3:1][NH:2][C:3](=[O:4])[C@H:5]([CH2:6][CH:7]([CH3:8])[CH3:9])[NH:10][C:11](=[O:12])[O:13][CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1\"},\"mapped_reaction_smiles\":\"O[C:3](=[O:4])[C@H:5]([CH2:6][CH:7]([CH3:8])[CH3:9])[NH:10][C:11](=[O:12])[O:13][CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1.[CH3:1][NH2:2]>CCN(C(C)C)C(C)C.CN(C)C(On1nnc2ccccc21)=[N+](C)C.CN(C)C=O.Cl.F[B-](F)(F)F>[CH3:1][NH:2][C:3](=[O:4])[C@H:5]([CH2:6][CH:7]([CH3:8])[CH3:9])[NH:10][C:11](=[O:12])[O:13][CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1\"}",
"reactionStep": {
"id": "sa_3617423b81877772fac2271f",
"reactionHash": "61ff998fbd218d4bdcb6a4951adc61df705e43ea278920ee9f2c8c4deca0f9ee"
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"children": [
{
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"moleculeId": "sa_e00cdbb7fb9d3ecf114a19d3",
"parentId": "10657",
"isLeaf": true,
"molecule": {
"id": "sa_e00cdbb7fb9d3ecf114a19d3",
"inchikey": "BAVYZALUXZFZLV-UHFFFAOYSA-N",
"smiles": "CN"
},
"smiles": "CN",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "10659",
"routeId": "sa_2c3e7c7cf2f32a5d88f65c6d",
"moleculeId": "sa_0118bc42866c1699933b10c1",
"parentId": "10657",
"isLeaf": true,
"molecule": {
"id": "sa_0118bc42866c1699933b10c1",
"inchikey": "USPFMEKVPDBMCG-LBPRGKRZSA-N",
"smiles": "CC(C)C[C@H](NC(=O)OCc1ccccc1)C(=O)O"
},
"smiles": "CC(C)C[C@H](NC(=O)OCc1ccccc1)C(=O)O",
"reactionStepId": null,
"template": null,
"metadata": null,
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}
]
}
]
},
{
"id": "10660",
"routeId": "sa_2c3e7c7cf2f32a5d88f65c6d",
"moleculeId": "sa_ffef3f88ed2620f9527208c1",
"parentId": "10655",
"isLeaf": false,
"molecule": {
"id": "sa_ffef3f88ed2620f9527208c1",
"inchikey": "XPSHWWXTUGQNPA-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)N1CCn2c(Br)nc(C(=O)O)c2C1"
},
"smiles": "CC(C)(C)OC(=O)N1CCn2c(Br)nc(C(=O)O)c2C1",
"reactionStepId": "sa_4e069c2c39b1c41f821e25e8",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20110034443A1;0123;1011102\",\"rsmi\":\"C[O:18][C:16]([c:15]1[n:14][c:12]([Br:13])[n:11]2[c:19]1[CH2:20][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:9][CH2:10]2)=[O:17]>CO.O.[Li+].O>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][n:11]2[c:12]([Br:13])[n:14][c:15]([C:16](=[O:17])[OH:18])[c:19]2[CH2:20]1\"},\"mapped_reaction_smiles\":\"C[O:18][C:16]([c:15]1[n:14][c:12]([Br:13])[n:11]2[c:19]1[CH2:20][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:9][CH2:10]2)=[O:17]>CO.O.[Li+].O>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][n:11]2[c:12]([Br:13])[n:14][c:15]([C:16](=[O:17])[OH:18])[c:19]2[CH2:20]1\"}",
"reactionStep": {
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"reactionHash": "d246b58f04002e2ddf53f2ec76792aa87a168db0a33fc6bec5bf8d963e58f4fa"
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"smiles": "COC(=O)c1nc(Br)n2c1CN(C(=O)OC(C)(C)C)CC2"
},
"smiles": "COC(=O)c1nc(Br)n2c1CN(C(=O)OC(C)(C)C)CC2",
"reactionStepId": "sa_c39b3a08b1fd96b4747d5cb1",
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"metadata": "{\"annotations\":{\"ID\":\"US20110034443A1;0122;1011101\",\"rsmi\":\"O=C1CCC(=O)N1[Br:20].[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]2[n:18]([cH:19][n:21]1)[CH2:17][CH2:16][N:8]([C:9](=[O:10])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15])[CH2:7]2>CC#N.ClCCl>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]2[n:18]([c:19]([Br:20])[n:21]1)[CH2:17][CH2:16][N:8]([C:9](=[O:10])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15])[CH2:7]2\"},\"mapped_reaction_smiles\":\"O=C1CCC(=O)N1[Br:20].[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]2[n:18]([cH:19][n:21]1)[CH2:17][CH2:16][N:8]([C:9](=[O:10])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15])[CH2:7]2>CC#N.ClCCl>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]2[n:18]([c:19]([Br:20])[n:21]1)[CH2:17][CH2:16][N:8]([C:9](=[O:10])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15])[CH2:7]2\"}",
"reactionStep": {
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"children": [
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"molecule": {
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"smiles": "COC(=O)c1ncn2c1CN(C(=O)OC(C)(C)C)CC2"
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"metadata": "{\"annotations\":{\"ID\":\"US20110034443A1;0121;1011100\",\"rsmi\":\"CC(C)(C)OC(=O)O[C:9](=[O:10])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15].c1ccc(C[N:8]2[CH2:7][c:6]3[c:5]([C:3]([O:2][CH3:1])=[O:4])[n:20][cH:19][n:18]3[CH2:17][CH2:16]2)cc1>CCN(C(C)C)C(C)C.CCO.O.O.[Pd+2]>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]2[n:18]([cH:19][n:20]1)[CH2:17][CH2:16][N:8]([C:9](=[O:10])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15])[CH2:7]2\"},\"mapped_reaction_smiles\":\"CC(C)(C)OC(=O)O[C:9](=[O:10])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15].c1ccc(C[N:8]2[CH2:7][c:6]3[c:5]([C:3]([O:2][CH3:1])=[O:4])[n:20][cH:19][n:18]3[CH2:17][CH2:16]2)cc1>CCN(C(C)C)C(C)C.CCO.O.O.[Pd+2]>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]2[n:18]([cH:19][n:20]1)[CH2:17][CH2:16][N:8]([C:9](=[O:10])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15])[CH2:7]2\"}",
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"smiles": "CC(C)(C)OC(=O)OC(=O)OC(C)(C)C",
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{
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"smiles": "COC(=O)c1ncn2c1CN(Cc1ccccc1)CC2",
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{
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}
}