Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
O=C(Nc1cnc(Br)cn1)[C@H](CC1CCCC1)N1Cc2c(cccc2C(F)(F)F)C1=O
InChiKey
OKVIXLORDPHPDZ-INIZCTEOSA-N
Route Signature
613f0a27bd7b5650f603a573db63232c6ac6b2e58217e8d0c670623a397cd6a2
Synthesis route with 5 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_d475dbcb48d1d021145bbbcb",
"signature": "613f0a27bd7b5650f603a573db63232c6ac6b2e58217e8d0c670623a397cd6a2",
"contentHash": "c7cb0b0b77f0d45b2a9ee9e0a981113cedc72cac748677113351a73d6f5a6fdf",
"length": 5,
"isConvergent": true
},
"target": {
"id": "sa_64086d1d82628d6c1a54d5a3",
"benchmarkSetId": "7390a9c2522b1c81605e80a42a8de7c7ad9a5797d028633b54904bc78f091bb8",
"targetId": "n5-04165",
"moleculeId": "sa_7297b239853fa2f2962bf907",
"smiles": "O=C(Nc1cnc(Br)cn1)[C@H](CC1CCCC1)N1Cc2c(cccc2C(F)(F)F)C1=O",
"routeLength": 5,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_7297b239853fa2f2962bf907",
"inchikey": "OKVIXLORDPHPDZ-INIZCTEOSA-N",
"smiles": "O=C(Nc1cnc(Br)cn1)[C@H](CC1CCCC1)N1Cc2c(cccc2C(F)(F)F)C1=O"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 6
},
"rootNode": {
"id": "2493",
"routeId": "sa_d475dbcb48d1d021145bbbcb",
"moleculeId": "sa_7297b239853fa2f2962bf907",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_7297b239853fa2f2962bf907",
"inchikey": "OKVIXLORDPHPDZ-INIZCTEOSA-N",
"smiles": "O=C(Nc1cnc(Br)cn1)[C@H](CC1CCCC1)N1Cc2c(cccc2C(F)(F)F)C1=O"
},
"smiles": "O=C(Nc1cnc(Br)cn1)[C@H](CC1CCCC1)N1Cc2c(cccc2C(F)(F)F)C1=O",
"reactionStepId": "sa_c1c442476413cd78f6828e4d",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08697705B2;0227;1447931\",\"rsmi\":\"O[C:2](=[O:1])[C@H:11]([CH2:12][CH:13]1[CH2:14][CH2:15][CH2:16][CH2:17]1)[N:18]1[CH2:19][c:20]2[c:21]([C:22]([F:23])([F:24])[F:25])[cH:26][cH:27][cH:28][c:29]2[C:30]1=[O:31].[NH2:3][c:4]1[n:5][cH:6][c:7]([Br:8])[n:9][cH:10]1>CN(C)C=O.Cc1cccc(C)n1.ClCCl.O=C(Cl)C(=O)Cl>[O:1]=[C:2]([NH:3][c:4]1[n:5][cH:6][c:7]([Br:8])[n:9][cH:10]1)[C@H:11]([CH2:12][CH:13]1[CH2:14][CH2:15][CH2:16][CH2:17]1)[N:18]1[CH2:19][c:20]2[c:21]([C:22]([F:23])([F:24])[F:25])[cH:26][cH:27][cH:28][c:29]2[C:30]1=[O:31]\"},\"mapped_reaction_smiles\":\"O[C:2](=[O:1])[C@H:11]([CH2:12][CH:13]1[CH2:14][CH2:15][CH2:16][CH2:17]1)[N:18]1[CH2:19][c:20]2[c:21]([C:22]([F:23])([F:24])[F:25])[cH:26][cH:27][cH:28][c:29]2[C:30]1=[O:31].[NH2:3][c:4]1[n:5][cH:6][c:7]([Br:8])[n:9][cH:10]1>CN(C)C=O.Cc1cccc(C)n1.ClCCl.O=C(Cl)C(=O)Cl>[O:1]=[C:2]([NH:3][c:4]1[n:5][cH:6][c:7]([Br:8])[n:9][cH:10]1)[C@H:11]([CH2:12][CH:13]1[CH2:14][CH2:15][CH2:16][CH2:17]1)[N:18]1[CH2:19][c:20]2[c:21]([C:22]([F:23])([F:24])[F:25])[cH:26][cH:27][cH:28][c:29]2[C:30]1=[O:31]\"}",
"reactionStep": {
"id": "sa_c1c442476413cd78f6828e4d",
"reactionHash": "38e28daaf32a259ded8e2c61fecdba3d045928dfb1e1280831565da9cbf8d516"
},
"children": [
{
"id": "2494",
"routeId": "sa_d475dbcb48d1d021145bbbcb",
"moleculeId": "sa_c14d80ee9e75f2790da7a2c8",
"parentId": "2493",
"isLeaf": false,
"molecule": {
"id": "sa_c14d80ee9e75f2790da7a2c8",
"inchikey": "GLHYEOSZBKZCOO-AWEZNQCLSA-N",
"smiles": "O=C(O)[C@H](CC1CCCC1)N1Cc2c(cccc2C(F)(F)F)C1=O"
},
"smiles": "O=C(O)[C@H](CC1CCCC1)N1Cc2c(cccc2C(F)(F)F)C1=O",
"reactionStepId": "sa_962d9d71e594670a2f816b56",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08697705B2;0191;1447911\",\"rsmi\":\"C[O:3][C:2](=[O:1])[C@H:4]([CH2:5][CH:6]1[CH2:7][CH2:8][CH2:9][CH2:10]1)[N:11]1[CH2:12][c:13]2[c:14]([C:15]([F:16])([F:17])[F:18])[cH:19][cH:20][cH:21][c:22]2[C:23]1=[O:24]>C1CCOC1.Cl.O.O.[Li+].O>[O:1]=[C:2]([OH:3])[C@H:4]([CH2:5][CH:6]1[CH2:7][CH2:8][CH2:9][CH2:10]1)[N:11]1[CH2:12][c:13]2[c:14]([C:15]([F:16])([F:17])[F:18])[cH:19][cH:20][cH:21][c:22]2[C:23]1=[O:24]\"},\"mapped_reaction_smiles\":\"C[O:3][C:2](=[O:1])[C@H:4]([CH2:5][CH:6]1[CH2:7][CH2:8][CH2:9][CH2:10]1)[N:11]1[CH2:12][c:13]2[c:14]([C:15]([F:16])([F:17])[F:18])[cH:19][cH:20][cH:21][c:22]2[C:23]1=[O:24]>C1CCOC1.Cl.O.O.[Li+].O>[O:1]=[C:2]([OH:3])[C@H:4]([CH2:5][CH:6]1[CH2:7][CH2:8][CH2:9][CH2:10]1)[N:11]1[CH2:12][c:13]2[c:14]([C:15]([F:16])([F:17])[F:18])[cH:19][cH:20][cH:21][c:22]2[C:23]1=[O:24]\"}",
"reactionStep": {
"id": "sa_962d9d71e594670a2f816b56",
"reactionHash": "19082149c15d012916038d4813411ae129d0066ecf15589f78da3add0630d674"
},
"children": [
{
"id": "2495",
"routeId": "sa_d475dbcb48d1d021145bbbcb",
"moleculeId": "sa_fd238281182384692fd79514",
"parentId": "2494",
"isLeaf": false,
"molecule": {
"id": "sa_fd238281182384692fd79514",
"inchikey": "YYDZFNIBUICQOH-HNNXBMFYSA-N",
"smiles": "COC(=O)[C@H](CC1CCCC1)N1Cc2c(cccc2C(F)(F)F)C1=O"
},
"smiles": "COC(=O)[C@H](CC1CCCC1)N1Cc2c(cccc2C(F)(F)F)C1=O",
"reactionStepId": "sa_0b426a7dcfdab7d32e6bcf46",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08697705B2;0190;1447910\",\"rsmi\":\"CO[C:24]([c:23]1[c:14]([CH2:13]Br)[c:15]([C:16]([F:17])([F:18])[F:19])[cH:20][cH:21][cH:22]1)=[O:25].[CH3:1][O:2][C:3](=[O:4])[C@H:5]([CH2:6][CH:7]1[CH2:8][CH2:9][CH2:10][CH2:11]1)[NH2:12]>CC#N.CCN(CC)CC.O>[CH3:1][O:2][C:3](=[O:4])[C@H:5]([CH2:6][CH:7]1[CH2:8][CH2:9][CH2:10][CH2:11]1)[N:12]1[CH2:13][c:14]2[c:15]([C:16]([F:17])([F:18])[F:19])[cH:20][cH:21][cH:22][c:23]2[C:24]1=[O:25]\"},\"mapped_reaction_smiles\":\"CO[C:24]([c:23]1[c:14]([CH2:13]Br)[c:15]([C:16]([F:17])([F:18])[F:19])[cH:20][cH:21][cH:22]1)=[O:25].[CH3:1][O:2][C:3](=[O:4])[C@H:5]([CH2:6][CH:7]1[CH2:8][CH2:9][CH2:10][CH2:11]1)[NH2:12]>CC#N.CCN(CC)CC.O>[CH3:1][O:2][C:3](=[O:4])[C@H:5]([CH2:6][CH:7]1[CH2:8][CH2:9][CH2:10][CH2:11]1)[N:12]1[CH2:13][c:14]2[c:15]([C:16]([F:17])([F:18])[F:19])[cH:20][cH:21][cH:22][c:23]2[C:24]1=[O:25]\"}",
"reactionStep": {
"id": "sa_0b426a7dcfdab7d32e6bcf46",
"reactionHash": "f5c4c7ac2f0e9ec456c3a31b9ed2b93574625cf578802f4f4e392a1631da083c"
},
"children": [
{
"id": "2496",
"routeId": "sa_d475dbcb48d1d021145bbbcb",
"moleculeId": "sa_d6465896269362d225c2c4da",
"parentId": "2495",
"isLeaf": false,
"molecule": {
"id": "sa_d6465896269362d225c2c4da",
"inchikey": "DFYWLNAELNNBMC-UHFFFAOYSA-N",
"smiles": "COC(=O)c1cccc(C(F)(F)F)c1CBr"
},
"smiles": "COC(=O)c1cccc(C(F)(F)F)c1CBr",
"reactionStepId": "sa_ce8c6739c20af46e67a4b5e3",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08697705B2;0188;1447908\",\"rsmi\":\"O=C1CCC(=O)N1[Br:8].[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([CH3:7])[c:9]([C:10]([F:11])([F:12])[F:13])[cH:14][cH:15][cH:16]1>CCCCCC.CCOC(C)=O.O=C(OOC(=O)c1ccccc1)c1ccccc1.c1ccccc1>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([CH2:7][Br:8])[c:9]([C:10]([F:11])([F:12])[F:13])[cH:14][cH:15][cH:16]1\"},\"mapped_reaction_smiles\":\"O=C1CCC(=O)N1[Br:8].[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([CH3:7])[c:9]([C:10]([F:11])([F:12])[F:13])[cH:14][cH:15][cH:16]1>CCCCCC.CCOC(C)=O.O=C(OOC(=O)c1ccccc1)c1ccccc1.c1ccccc1>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([CH2:7][Br:8])[c:9]([C:10]([F:11])([F:12])[F:13])[cH:14][cH:15][cH:16]1\"}",
"reactionStep": {
"id": "sa_ce8c6739c20af46e67a4b5e3",
"reactionHash": "d70c39aab0dbdffea71cd18235133de2299ad2b702a585dae86cf12cf44753d8"
},
"children": [
{
"id": "2497",
"routeId": "sa_d475dbcb48d1d021145bbbcb",
"moleculeId": "sa_48e6d6a36725ea9de0894456",
"parentId": "2496",
"isLeaf": false,
"molecule": {
"id": "sa_48e6d6a36725ea9de0894456",
"inchikey": "KFJGSNVBDYRBAD-UHFFFAOYSA-N",
"smiles": "COC(=O)c1cccc(C(F)(F)F)c1C"
},
"smiles": "COC(=O)c1cccc(C(F)(F)F)c1C",
"reactionStepId": "sa_ca5965c1e3c322911bad0eb5",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08697705B2;0187;1447907\",\"rsmi\":\"O[C:3](=[O:4])[c:5]1[c:6]([CH3:7])[c:8]([C:9]([F:10])([F:11])[F:12])[cH:13][cH:14][cH:15]1.[CH3:1][OH:2]>O=S(=O)(O)O>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([CH3:7])[c:8]([C:9]([F:10])([F:11])[F:12])[cH:13][cH:14][cH:15]1\"},\"mapped_reaction_smiles\":\"O[C:3](=[O:4])[c:5]1[c:6]([CH3:7])[c:8]([C:9]([F:10])([F:11])[F:12])[cH:13][cH:14][cH:15]1.[CH3:1][OH:2]>O=S(=O)(O)O>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([CH3:7])[c:8]([C:9]([F:10])([F:11])[F:12])[cH:13][cH:14][cH:15]1\"}",
"reactionStep": {
"id": "sa_ca5965c1e3c322911bad0eb5",
"reactionHash": "133290f4a87fbde845128b64f872e71affa95cc2d4a3d78f2b9e3b0524b251d4"
},
"children": [
{
"id": "2498",
"routeId": "sa_d475dbcb48d1d021145bbbcb",
"moleculeId": "sa_061a3efbe4d30c2cc87d48e7",
"parentId": "2497",
"isLeaf": true,
"molecule": {
"id": "sa_061a3efbe4d30c2cc87d48e7",
"inchikey": "OKKJLVBELUTLKV-UHFFFAOYSA-N",
"smiles": "CO"
},
"smiles": "CO",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "2499",
"routeId": "sa_d475dbcb48d1d021145bbbcb",
"moleculeId": "sa_3fc7cff3de0f6cbcc1556e46",
"parentId": "2497",
"isLeaf": true,
"molecule": {
"id": "sa_3fc7cff3de0f6cbcc1556e46",
"inchikey": "SSCFPSMXIDAJDT-UHFFFAOYSA-N",
"smiles": "Cc1c(C(=O)O)cccc1C(F)(F)F"
},
"smiles": "Cc1c(C(=O)O)cccc1C(F)(F)F",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "2500",
"routeId": "sa_d475dbcb48d1d021145bbbcb",
"moleculeId": "sa_ccdcf23ac83e7a68bfa4f2e5",
"parentId": "2496",
"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": "2501",
"routeId": "sa_d475dbcb48d1d021145bbbcb",
"moleculeId": "sa_5f78efa9edabc70004351df2",
"parentId": "2495",
"isLeaf": false,
"molecule": {
"id": "sa_5f78efa9edabc70004351df2",
"inchikey": "RZAFJDYKEFALQU-QMMMGPOBSA-N",
"smiles": "COC(=O)[C@@H](N)CC1CCCC1"
},
"smiles": "COC(=O)[C@@H](N)CC1CCCC1",
"reactionStepId": "sa_e32571e75eb8627494bccb8d",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08697705B2;0189;1447909\",\"rsmi\":\"O[C:3](=[O:4])[C@@H:5]([NH2:6])[CH2:7][CH:8]1[CH2:9][CH2:10][CH2:11][CH2:12]1.[CH3:1][OH:2]>Cl>[CH3:1][O:2][C:3](=[O:4])[C@@H:5]([NH2:6])[CH2:7][CH:8]1[CH2:9][CH2:10][CH2:11][CH2:12]1\"},\"mapped_reaction_smiles\":\"O[C:3](=[O:4])[C@@H:5]([NH2:6])[CH2:7][CH:8]1[CH2:9][CH2:10][CH2:11][CH2:12]1.[CH3:1][OH:2]>Cl>[CH3:1][O:2][C:3](=[O:4])[C@@H:5]([NH2:6])[CH2:7][CH:8]1[CH2:9][CH2:10][CH2:11][CH2:12]1\"}",
"reactionStep": {
"id": "sa_e32571e75eb8627494bccb8d",
"reactionHash": "6b8d5545dd2887e1bc4f0313a2bb7fd79f3e9c629245fa7b80f0b267ea4cda59"
},
"children": [
{
"id": "2502",
"routeId": "sa_d475dbcb48d1d021145bbbcb",
"moleculeId": "sa_9e6d04451e4dbf4aa12f2244",
"parentId": "2501",
"isLeaf": true,
"molecule": {
"id": "sa_9e6d04451e4dbf4aa12f2244",
"inchikey": "KDYAKYRBGLKMAK-ZETCQYMHSA-N",
"smiles": "N[C@@H](CC1CCCC1)C(=O)O"
},
"smiles": "N[C@@H](CC1CCCC1)C(=O)O",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "2503",
"routeId": "sa_d475dbcb48d1d021145bbbcb",
"moleculeId": "sa_061a3efbe4d30c2cc87d48e7",
"parentId": "2501",
"isLeaf": true,
"molecule": {
"id": "sa_061a3efbe4d30c2cc87d48e7",
"inchikey": "OKKJLVBELUTLKV-UHFFFAOYSA-N",
"smiles": "CO"
},
"smiles": "CO",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
]
},
{
"id": "2504",
"routeId": "sa_d475dbcb48d1d021145bbbcb",
"moleculeId": "sa_289db53ed24cf1338eb140e5",
"parentId": "2493",
"isLeaf": true,
"molecule": {
"id": "sa_289db53ed24cf1338eb140e5",
"inchikey": "KRRTXVSBTPCDOS-UHFFFAOYSA-N",
"smiles": "Nc1cnc(Br)cn1"
},
"smiles": "Nc1cnc(Br)cn1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
}