Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
COC1(C(F)(F)F)CCC2(CC1)NC(=O)C(c1cc(Br)ccc1C)=C2O
InChiKey
DNIAMKSAFABZOO-UHFFFAOYSA-N
Route Signature
b488a83a6c3628400340aa051e72de966d949e6d212616b926ab1763198df288
Synthesis route with 4 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_cd93d8241f69289747d9ee8d",
"signature": "b488a83a6c3628400340aa051e72de966d949e6d212616b926ab1763198df288",
"contentHash": "2cd4a49c3c48e1870ea36a4fe9763b312fb8154deaa59a290cc11c0a0781f0f8",
"length": 4,
"isConvergent": true
},
"target": {
"id": "sa_78c3e07dc3faf03f8d240581",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-00312",
"moleculeId": "sa_c2a904de40e00364e60b02ba",
"smiles": "COC1(C(F)(F)F)CCC2(CC1)NC(=O)C(c1cc(Br)ccc1C)=C2O",
"routeLength": 4,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_c2a904de40e00364e60b02ba",
"inchikey": "DNIAMKSAFABZOO-UHFFFAOYSA-N",
"smiles": "COC1(C(F)(F)F)CCC2(CC1)NC(=O)C(c1cc(Br)ccc1C)=C2O"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "9395",
"routeId": "sa_cd93d8241f69289747d9ee8d",
"moleculeId": "sa_c2a904de40e00364e60b02ba",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_c2a904de40e00364e60b02ba",
"inchikey": "DNIAMKSAFABZOO-UHFFFAOYSA-N",
"smiles": "COC1(C(F)(F)F)CCC2(CC1)NC(=O)C(c1cc(Br)ccc1C)=C2O"
},
"smiles": "COC1(C(F)(F)F)CCC2(CC1)NC(=O)C(c1cc(Br)ccc1C)=C2O",
"reactionStepId": "sa_d91749839c258b298bc796de",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US09278925B2;0371;1734510\",\"rsmi\":\"CO[C:25]([C:10]1([NH:13][C:14](=[O:15])[CH2:16][c:17]2[c:18]([CH3:19])[cH:20][cH:21][c:22]([Br:23])[cH:24]2)[CH2:9][CH2:8][C:3]([O:2][CH3:1])([C:4]([F:5])([F:6])[F:7])[CH2:12][CH2:11]1)=[O:26]>CC(C)(C)O.CN(C)C=O.Cl.[K+]>[CH3:1][O:2][C:3]1([C:4]([F:5])([F:6])[F:7])[CH2:8][CH2:9][C:10]2([CH2:11][CH2:12]1)[NH:13][C:14](=[O:15])[C:16]([c:17]1[c:18]([CH3:19])[cH:20][cH:21][c:22]([Br:23])[cH:24]1)=[C:25]2[OH:26]\"},\"mapped_reaction_smiles\":\"CO[C:25]([C:10]1([NH:13][C:14](=[O:15])[CH2:16][c:17]2[c:18]([CH3:19])[cH:20][cH:21][c:22]([Br:23])[cH:24]2)[CH2:9][CH2:8][C:3]([O:2][CH3:1])([C:4]([F:5])([F:6])[F:7])[CH2:12][CH2:11]1)=[O:26]>CC(C)(C)O.CN(C)C=O.Cl.[K+]>[CH3:1][O:2][C:3]1([C:4]([F:5])([F:6])[F:7])[CH2:8][CH2:9][C:10]2([CH2:11][CH2:12]1)[NH:13][C:14](=[O:15])[C:16]([c:17]1[c:18]([CH3:19])[cH:20][cH:21][c:22]([Br:23])[cH:24]1)=[C:25]2[OH:26]\"}",
"reactionStep": {
"id": "sa_d91749839c258b298bc796de",
"reactionHash": "86c2ac3cc5546991a0eae0e729f203150cc5cfc60f401b775704661585664b99"
},
"children": [
{
"id": "9396",
"routeId": "sa_cd93d8241f69289747d9ee8d",
"moleculeId": "sa_d98212bd33a6e824193eb8ba",
"parentId": "9395",
"isLeaf": false,
"molecule": {
"id": "sa_d98212bd33a6e824193eb8ba",
"inchikey": "SHBODTFSIHPDDX-UHFFFAOYSA-N",
"smiles": "COC(=O)C1(NC(=O)Cc2cc(Br)ccc2C)CCC(OC)(C(F)(F)F)CC1"
},
"smiles": "COC(=O)C1(NC(=O)Cc2cc(Br)ccc2C)CCC(OC)(C(F)(F)F)CC1",
"reactionStepId": "sa_fc7b6aada84d3f6c9ff3e177",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US09278925B2;0347;1734507\",\"rsmi\":\"Cl[C:7](=[O:8])[CH2:9][c:10]1[c:11]([CH3:12])[cH:13][cH:14][c:15]([Br:16])[cH:17]1.[CH3:1][O:2][C:3](=[O:4])[C:5]1([NH2:6])[CH2:18][CH2:19][C:20]([O:21][CH3:22])([C:23]([F:24])([F:25])[F:26])[CH2:27][CH2:28]1>CCN(CC)CC.ClCCl>[CH3:1][O:2][C:3](=[O:4])[C:5]1([NH:6][C:7](=[O:8])[CH2:9][c:10]2[c:11]([CH3:12])[cH:13][cH:14][c:15]([Br:16])[cH:17]2)[CH2:18][CH2:19][C:20]([O:21][CH3:22])([C:23]([F:24])([F:25])[F:26])[CH2:27][CH2:28]1\"},\"mapped_reaction_smiles\":\"Cl[C:7](=[O:8])[CH2:9][c:10]1[c:11]([CH3:12])[cH:13][cH:14][c:15]([Br:16])[cH:17]1.[CH3:1][O:2][C:3](=[O:4])[C:5]1([NH2:6])[CH2:18][CH2:19][C:20]([O:21][CH3:22])([C:23]([F:24])([F:25])[F:26])[CH2:27][CH2:28]1>CCN(CC)CC.ClCCl>[CH3:1][O:2][C:3](=[O:4])[C:5]1([NH:6][C:7](=[O:8])[CH2:9][c:10]2[c:11]([CH3:12])[cH:13][cH:14][c:15]([Br:16])[cH:17]2)[CH2:18][CH2:19][C:20]([O:21][CH3:22])([C:23]([F:24])([F:25])[F:26])[CH2:27][CH2:28]1\"}",
"reactionStep": {
"id": "sa_fc7b6aada84d3f6c9ff3e177",
"reactionHash": "fca3d0000dfd3d9ff6fcc772fa289fc6356bf011adf8fb83d21aaa77d027710c"
},
"children": [
{
"id": "9397",
"routeId": "sa_cd93d8241f69289747d9ee8d",
"moleculeId": "sa_8ab4c67775cae525828ce991",
"parentId": "9396",
"isLeaf": false,
"molecule": {
"id": "sa_8ab4c67775cae525828ce991",
"inchikey": "CXCKOROWEXQHDY-UHFFFAOYSA-N",
"smiles": "Cc1ccc(Br)cc1CC(=O)Cl"
},
"smiles": "Cc1ccc(Br)cc1CC(=O)Cl",
"reactionStepId": "sa_225018b65c8e6c5abf3010c1",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US09278925B2;0249;1734488\",\"rsmi\":\"O=S(Cl)[Cl:7].O[C:5]([CH2:4][c:3]1[c:2]([CH3:1])[cH:12][cH:11][c:9]([Br:10])[cH:8]1)=[O:6]>>[CH3:1][c:2]1[c:3]([CH2:4][C:5](=[O:6])[Cl:7])[cH:8][c:9]([Br:10])[cH:11][cH:12]1\"},\"mapped_reaction_smiles\":\"O=S(Cl)[Cl:7].O[C:5]([CH2:4][c:3]1[c:2]([CH3:1])[cH:12][cH:11][c:9]([Br:10])[cH:8]1)=[O:6]>>[CH3:1][c:2]1[c:3]([CH2:4][C:5](=[O:6])[Cl:7])[cH:8][c:9]([Br:10])[cH:11][cH:12]1\"}",
"reactionStep": {
"id": "sa_225018b65c8e6c5abf3010c1",
"reactionHash": "dbcfa5d28c9ddee6498ea15315cd1df5863dbc2f7f60636692e96bc0092d9cf6"
},
"children": [
{
"id": "9398",
"routeId": "sa_cd93d8241f69289747d9ee8d",
"moleculeId": "sa_cd67ce42f230ef1a4063353c",
"parentId": "9397",
"isLeaf": true,
"molecule": {
"id": "sa_cd67ce42f230ef1a4063353c",
"inchikey": "FYSNRJHAOHDILO-UHFFFAOYSA-N",
"smiles": "O=S(Cl)Cl"
},
"smiles": "O=S(Cl)Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "9399",
"routeId": "sa_cd93d8241f69289747d9ee8d",
"moleculeId": "sa_e4f567e09e301d5f9f5edcab",
"parentId": "9397",
"isLeaf": true,
"molecule": {
"id": "sa_e4f567e09e301d5f9f5edcab",
"inchikey": "KZGAACARPAMSTO-UHFFFAOYSA-N",
"smiles": "Cc1ccc(Br)cc1CC(=O)O"
},
"smiles": "Cc1ccc(Br)cc1CC(=O)O",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "9400",
"routeId": "sa_cd93d8241f69289747d9ee8d",
"moleculeId": "sa_57960ab25a0b955011282035",
"parentId": "9396",
"isLeaf": false,
"molecule": {
"id": "sa_57960ab25a0b955011282035",
"inchikey": "XORKLUYNZDYMBU-UHFFFAOYSA-N",
"smiles": "COC(=O)C1(N)CCC(OC)(C(F)(F)F)CC1"
},
"smiles": "COC(=O)C1(N)CCC(OC)(C(F)(F)F)CC1",
"reactionStepId": "sa_ac3735f6aed5ef58880aee7c",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US09278925B2;0302;1734501\",\"rsmi\":\"O[C:3](=[O:4])[C:5]1([NH2:6])[CH2:7][CH2:8][C:9]([O:10][CH3:11])([C:12]([F:13])([F:14])[F:15])[CH2:16][CH2:17]1.[CH3:1][OH:2]>O=S(Cl)Cl>[CH3:1][O:2][C:3](=[O:4])[C:5]1([NH2:6])[CH2:7][CH2:8][C:9]([O:10][CH3:11])([C:12]([F:13])([F:14])[F:15])[CH2:16][CH2:17]1\"},\"mapped_reaction_smiles\":\"O[C:3](=[O:4])[C:5]1([NH2:6])[CH2:7][CH2:8][C:9]([O:10][CH3:11])([C:12]([F:13])([F:14])[F:15])[CH2:16][CH2:17]1.[CH3:1][OH:2]>O=S(Cl)Cl>[CH3:1][O:2][C:3](=[O:4])[C:5]1([NH2:6])[CH2:7][CH2:8][C:9]([O:10][CH3:11])([C:12]([F:13])([F:14])[F:15])[CH2:16][CH2:17]1\"}",
"reactionStep": {
"id": "sa_ac3735f6aed5ef58880aee7c",
"reactionHash": "e16f1213ff88defeacc9f5920a104b571e526d29329f94222da2e172339ba603"
},
"children": [
{
"id": "9401",
"routeId": "sa_cd93d8241f69289747d9ee8d",
"moleculeId": "sa_061a3efbe4d30c2cc87d48e7",
"parentId": "9400",
"isLeaf": true,
"molecule": {
"id": "sa_061a3efbe4d30c2cc87d48e7",
"inchikey": "OKKJLVBELUTLKV-UHFFFAOYSA-N",
"smiles": "CO"
},
"smiles": "CO",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "9402",
"routeId": "sa_cd93d8241f69289747d9ee8d",
"moleculeId": "sa_3027fca66466f5296437e101",
"parentId": "9400",
"isLeaf": false,
"molecule": {
"id": "sa_3027fca66466f5296437e101",
"inchikey": "ZKDXGYXGHRZPRZ-UHFFFAOYSA-N",
"smiles": "COC1(C(F)(F)F)CCC(N)(C(=O)O)CC1"
},
"smiles": "COC1(C(F)(F)F)CCC(N)(C(=O)O)CC1",
"reactionStepId": "sa_11859eeec613f71675f0985e",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US09278925B2;0291;1734500\",\"rsmi\":\"O=C1N[C:12](=[O:13])[C:10]2([CH2:9][CH2:8][C:3]([O:2][CH3:1])([C:4]([F:5])([F:6])[F:7])[CH2:16][CH2:15]2)[NH:11]1.[OH2:14]>Cl.[Na+]>[CH3:1][O:2][C:3]1([C:4]([F:5])([F:6])[F:7])[CH2:8][CH2:9][C:10]([NH2:11])([C:12](=[O:13])[OH:14])[CH2:15][CH2:16]1\"},\"mapped_reaction_smiles\":\"O=C1N[C:12](=[O:13])[C:10]2([CH2:9][CH2:8][C:3]([O:2][CH3:1])([C:4]([F:5])([F:6])[F:7])[CH2:16][CH2:15]2)[NH:11]1.[OH2:14]>Cl.[Na+]>[CH3:1][O:2][C:3]1([C:4]([F:5])([F:6])[F:7])[CH2:8][CH2:9][C:10]([NH2:11])([C:12](=[O:13])[OH:14])[CH2:15][CH2:16]1\"}",
"reactionStep": {
"id": "sa_11859eeec613f71675f0985e",
"reactionHash": "4be19edbe36ba7a1e3e2b8113b84f64484fc3bb500c8cc73d26531250e5c6c7b"
},
"children": [
{
"id": "9403",
"routeId": "sa_cd93d8241f69289747d9ee8d",
"moleculeId": "sa_9db730c2b1ff10a29fd1fb6f",
"parentId": "9402",
"isLeaf": true,
"molecule": {
"id": "sa_9db730c2b1ff10a29fd1fb6f",
"inchikey": "OYDUACLGOVAAQM-UHFFFAOYSA-N",
"smiles": "COC1(C(F)(F)F)CCC2(CC1)NC(=O)NC2=O"
},
"smiles": "COC1(C(F)(F)F)CCC2(CC1)NC(=O)NC2=O",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "9404",
"routeId": "sa_cd93d8241f69289747d9ee8d",
"moleculeId": "sa_106b35b8a76bbe73829a0a69",
"parentId": "9402",
"isLeaf": true,
"molecule": {
"id": "sa_106b35b8a76bbe73829a0a69",
"inchikey": "XLYOFNOQVPJJNP-UHFFFAOYSA-N",
"smiles": "O"
},
"smiles": "O",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
]
}
]
}
}