Compound: hyperforin
SMILES: O=C1C(=C(O)[C@]2(C(=O)C(C)C)[C@@](CCC=C(C)C)(C)[C@H](C[C@]1(C2=O)CC=C(C)C)CC=C(C)C)CC=C(C)C
InChIKey: IWBJJCOKGLUQIZ-HQKKAZOISA-N
Synonyms: hyperforin, 11079-53-1, hiperforina, hyperforine, CHEBI:5834, RM741E34FP, (1R,5S,6R,7S)-4-hydroxy-6-methyl-1,3,7-tris(3-methylbut-2-en-1-yl)-6-(4-methylpent-3-en-1-yl)-5-(2-methylpropanoyl)bicyclo[3.3.1]non-3-ene-2,9-dione, CHEMBL1237210, (1R,5S,6R,7S)-4-hydroxy-5-isobutyryl-6-methyl-1,3,7-tris(3-methylbut-2-en-1-yl)-6-(4-methylpent-3-en-1-yl)bicyclo[3.3.1]non-3-ene-2,9-dione, (+)-Hyperforin, (1R,5R,7S,8R)-4-hydroxy-8-methyl-3,5,7-tris(3-methylbut-2-enyl)-8-(4-methylpent-3-enyl)-1-(2-methylpropanoyl)bicyclo[3.3.1]non-3-ene-2,9-dione, Bicyclo[3.3.1]non-3-ene-2,9-dione, 4-hydroxy-6-methyl-1,3,7-tris(3-methyl-2-buten-1-yl)-5-(2-methyl-1-oxopropyl)-6-(4-methyl-3-penten-1-yl)-, (1R,5S,6R,7S)-, UNII-RM741E34FP, HSDB 7646, BICYCLO(3.3.1)NON-3-ENE-2,9-DIONE, 4-HYDROXY-6-METHYL-1,3,7-TRIS(3-METHYL-2-BUTEN-1-YL)-5-(2-METHYL-1-OXOPROPYL)-6-(4-METHYL-3-PENTEN-1-YL)-, (1R,5S,6R,7S)-, C35H52O4, HYPERFORIN [MI], Spectrum5_002025, HYPERFORIN [HSDB], HYPERFORIN [WHO-DD], SCHEMBL98723, CHEMBL501711, GTPL2764, orb1684532, Hyperforin, >=85% (HPLC), SCHEMBL15557965, DTXSID90891409, Hyperforin - solution in methanol, IWBJJCOKGLUQIZ-HQKKAZOISA-N, DTXSID901371849, BDBM50193079, PDSP2_001346, DB01892, FH64889, NCGC00163120-01, HY-116330, CS-0065073, NS00011745, C07608, Q412742, HYPERFORIN (CONSTITUENT OF ST. JOHN'S WORT) [DSC], 4-Hydroxy-6-methyl-1,3,7-tris(3-methyl-2-butenyl)-5-(2-methyl-1-oxopropyl)-6-(4-methyl-3-pentenyl) bicyclo(3.3.1)non-3-ene-2,9-dione, Bicyclo(3.3.1)(1,4)benzodiazepin-5-one, 4-Hydroxy-6-methyl-1,3,7-tris(3-methyl-2-butenyl)-5-(2-methyl-1-oxopropyl)-6-(4-methyl-3-pentenyl)-, (1R,5S,6R,7S)-
Theoretical properties:
molecular_formula: C35H52O4
molecular_weight: 536.8 g/mol
exact_mass: 536.38656014 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 4
rotatable_bond_count: 11
heavy_atom_count: 39
topological_polar_surface_area: 71.4 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: Hyperforin is a cyclic terpene ketone that is a prenylated carbobicyclic acylphloroglucinol derivative produced by St. John's Wort, Hypericum perforatum. It has a role as an antibacterial agent, an antidepressant, an antineoplastic agent, an anti-inflammatory agent, an apoptosis inducer, a plant metabolite and a GABA reuptake inhibitor. It is a cyclic terpene ketone, a carbobicyclic compound and a sesquarterpenoid.
chebi: A cyclic terpene ketone that is a prenylated carbobicyclic acylphloroglucinol derivative produced by St. John's Wort, <em>Hypericum perforatum</em>.
chembl: Unnamed Compound is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: Hyperforin is a phytochemical produced by some of the members of the plant genus Hypericum, notably Hypericum perforatum (St John's wort). Hyperforin may be involved in the pharmacological effects of St. John's wort, specifically in its antidepressant effects. Meta-analyses of clinical trials suggest that H. perforatum is as effective as SSRIs for treating mild to moderate depression and is better tolerated, although findings are limited by short study durations. 
Hyperforin is found in significant amounts only in H. perforatum, where it accumulates as a probable plant defense compound, with modern carbon dioxide extraction methods used to isolate it from mixtures containing related compounds like adhyperforin.