CHEBI:5834 - hyperforin

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ChEBI Name hyperforin
ChEBI ID CHEBI:5834
Definition A cyclic terpene ketone that is a prenylated carbobicyclic acylphloroglucinol derivative produced by St. John's Wort, Hypericum perforatum.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information ChemicalBook:CB0273398, eMolecules:32232758, eMolecules:29780647, ZINC000004097413
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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.
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Formulae C35H52O4
C35H52O4
Net Charge 0
Average Mass 536.797
Monoisotopic Mass 536.38656
InChI InChI=1S/C35H52O4/c1-22(2)13-12-19-33(11)27(16-14-23(3)4)21-34(20-18-25(7)8)30(37)28(17-15-24(5)6)31(38)35(33,32(34)39)29(36)26(9)10/h13-15,18,26-27,38H,12,16-17,19-21H2,1-11H3/t27-,33+,34+,35-/m0/s1
InChIKey IWBJJCOKGLUQIZ-HQKKAZOISA-N
SMILES CC(C)C(=O)[C@@]12C(O)=C(CC=C(C)C)C(=O)[C@@](CC=C(C)C)(C[C@H](CC=C(C)C)[C@@]1(C)CCC=C(C)C)C2=O
Roles Classification
Biological Role(s): GABA reuptake inhibitor
A compound that inhibits the re-uptake of the neurotransmitter GABA from the synapse into the pre-synaptic neuron, so increasing the extracellular concentrations of the neurotransmitter and hence increasing neurotransmission.
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
antibacterial agent
A substance (or active part thereof) that kills or slows the growth of bacteria.
apoptosis inducer
Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
Application(s): GABA reuptake inhibitor
A compound that inhibits the re-uptake of the neurotransmitter GABA from the synapse into the pre-synaptic neuron, so increasing the extracellular concentrations of the neurotransmitter and hence increasing neurotransmission.
anti-inflammatory agent
Any compound that has anti-inflammatory effects.
antidepressant
Antidepressants are mood-stimulating drugs used primarily in the treatment of affective disorders and related conditions.
antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing hyperforin (CHEBI:5834) has role anti-inflammatory agent (CHEBI:67079)
hyperforin (CHEBI:5834) has role antibacterial agent (CHEBI:33282)
hyperforin (CHEBI:5834) has role antidepressant (CHEBI:35469)
hyperforin (CHEBI:5834) has role antineoplastic agent (CHEBI:35610)
hyperforin (CHEBI:5834) has role apoptosis inducer (CHEBI:68495)
hyperforin (CHEBI:5834) has role GABA reuptake inhibitor (CHEBI:85384)
hyperforin (CHEBI:5834) has role plant metabolite (CHEBI:76924)
hyperforin (CHEBI:5834) is a carbobicyclic compound (CHEBI:36785)
hyperforin (CHEBI:5834) is a cyclic terpene ketone (CHEBI:36130)
hyperforin (CHEBI:5834) is a sesquarterpenoid (CHEBI:51961)
IUPAC Name
(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
Synonyms Sources
(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 IUPAC
hiperforina ChEBI
Hyperforin KEGG COMPOUND
hyperforin UniProt
hyperforine ChEBI
Manual Xrefs Databases
C00034542 KNApSAcK
C07608 KEGG COMPOUND
DB01892 DrugBank
HMDB0030463 HMDB
HYF PDBeChem
Hyperforin Wikipedia
View more database links
Registry Numbers Types Sources
11079-53-1 CAS Registry Number KEGG COMPOUND
11079-53-1 CAS Registry Number ChemIDplus
6785663 Reaxys Registry Number Reaxys
Citations
Meinke MC, Richter H, Kleemann A, Lademann J, Tscherch K, Rohn S, Schempp CM (2015)
Characterization of atopic skin and the effect of a hyperforin-rich cream by laser scanning microscopy.
Journal of biomedical optics 20, 051013 [PubMed:25467783]
[show Abstract]
Ševčovičová A, Šemeláková M, Plšíková J, Loderer D, Imreová P, Gálová E, Kožurková M, Miadoková E, Fedoročko P (2015)
DNA-protective activities of hyperforin and aristoforin.
Toxicology in vitro : an international journal published in association with BIBRA 29, 631-637 [PubMed:25678043]
[show Abstract]
Novelli M, Beffy P, Menegazzi M, De Tata V, Martino L, Sgarbossa A, Porozov S, Pippa A, Masini M, Marchetti P, Masiello P (2014)
St. John's wort extract and hyperforin protect rat and human pancreatic islets against cytokine toxicity.
Acta diabetologica 51, 113-121 [PubMed:24121871]
[show Abstract]
Bellavance G, Barriault L (2014)
Total syntheses of hyperforin and papuaforins A-C, and formal synthesis of nemorosone through a gold(I)-catalyzed carbocyclization.
Angewandte Chemie (International ed. in English) 53, 6701-6704 [PubMed:24838522]
[show Abstract]
Pia Schiavone BI, Verotta L, Rosato A, Marilena M, Gibbons S, Bombardelli E, Franchini C, Corbo F (2014)
Anticancer and Antibacterial Activity of Hyperforin and Its Derivatives.
Anti-cancer agents in medicinal chemistry 14, 1397-1401 [PubMed:25173557]
[show Abstract]
Mitsopoulou KP, Vidali VP, Koliopoulos G, Couladouros EA, Michaelakis A (2014)
Hyperforin and deoxycohumulone as a larvicidal agent against Culex pipiens (Diptera: Culicidae).
Chemosphere 100, 124-129 [PubMed:24377447]
[show Abstract]
Haag SF, Tscherch K, Arndt S, Kleemann A, Gersonde I, Lademann J, Rohn S, Meinke MC (2014)
Enhancement of skin radical scavenging activity and stratum corneum lipids after the application of a hyperforin-rich cream.
European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V 86, 227-233 [PubMed:23811220]
[show Abstract]
Lee SK, Kim JE, Kim YJ, Kim MJ, Kang TC (2014)
Hyperforin attenuates microglia activation and inhibits p65-Ser276 NFκB phosphorylation in the rat piriform cortex following status epilepticus.
Neuroscience research 85, 39-50 [PubMed:24881563]
[show Abstract]
Sell TS, Belkacemi T, Flockerzi V, Beck A (2014)
Protonophore properties of hyperforin are essential for its pharmacological activity.
Scientific reports 4, 7500 [PubMed:25511254]
[show Abstract]
Nakamura K, Aizawa K, Yamauchi J, Tanoue A (2013)
Hyperforin inhibits cell proliferation and differentiation in mouse embryonic stem cells.
Cell proliferation 46, 529-537 [PubMed:24033566]
[show Abstract]
Billard C, Merhi F, Bauvois B (2013)
Mechanistic insights into the antileukemic activity of hyperforin.
Current cancer drug targets 13, 1-10 [PubMed:22924417]
[show Abstract]
Lin Y, Zhang JC, Fu J, Chen F, Wang J, Wu ZL, Yuan SY (2013)
Hyperforin attenuates brain damage induced by transient middle cerebral artery occlusion (MCAO) in rats via inhibition of TRPC6 channels degradation.
Journal of cerebral blood flow and metabolism : official journal of the International Society of Cerebral Blood Flow and Metabolism 33, 253-262 [PubMed:23149561]
[show Abstract]
Sparling BA, Moebius DC, Shair MD (2013)
Enantioselective total synthesis of hyperforin.
Journal of the American Chemical Society 135, 644-647 [PubMed:23270309]
[show Abstract]
Gibon J, Deloulme JC, Chevallier T, Ladevèze E, Abrous DN, Bouron A (2013)
The antidepressant hyperforin increases the phosphorylation of CREB and the expression of TrkB in a tissue-specific manner.
The international journal of neuropsychopharmacology 16, 189-198 [PubMed:22226089]
[show Abstract]
Zaher M, Tang R, Bombarda I, Merhi F, Bauvois B, Billard C (2012)
Hyperforin induces apoptosis of chronic lymphocytic leukemia cells through upregulation of the BH3-only protein Noxa.
International journal of oncology 40, 269-276 [PubMed:21947285]
[show Abstract]
Beerhues L (2006)
Hyperforin.
Phytochemistry 67, 2201-2207 [PubMed:16973193]
[show Abstract]
Watkins RE, Maglich JM, Moore LB, Wisely GB, Noble SM, Davis-Searles PR, Lambert MH, Kliewer SA, Redinbo MR (2003)
2.1 A crystal structure of human PXR in complex with the St. John's wort compound hyperforin.
Biochemistry 42, 1430-1438 [PubMed:12578355]
[show Abstract]
Last Modified
27 August 2021