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.
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Formula C35H52O4
Net Charge 0
Average Mass 536.78498
Monoisotopic Mass 536.387
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[C@H](CC=C(C)C)[C@@]1(C)CCC=C(C)C)C(=O)C(CC=C(C)C)=C2O
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 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.
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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
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
6785663 Beilstein Registry Number Beilstein
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Last Modified
02 April 2015