CHEBI:9921 - valerenic acid

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ChEBI Name valerenic acid
ChEBI ID CHEBI:9921
Definition A monocarboxylic acid that is 2-methylprop-2-enoic acid which is substituted at position 3 by a 3,7-dimethyl-2,4,5,6,7,7a-hexahydro-1H-inden-4-yl group. A bicyclic sesquiterpenoid constituent of the essential oil of the Valerian plant.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C15H22O2
Net Charge 0
Average Mass 234.33400
Monoisotopic Mass 234.16198
InChI InChI=1S/C15H22O2/c1-9-4-6-12(8-11(3)15(16)17)14-10(2)5-7-13(9)14/h8-9,12-13H,4-7H2,1-3H3,(H,16,17)/b11-8+/t9-,12+,13-/m1/s1
InChIKey FEBNTWHYQKGEIQ-SUKRRCERSA-N
SMILES [H][C@]12CCC(C)=C1[C@@H](CC[C@H]2C)\C=C(/C)C(O)=O
Metabolite of Species Details
Valeriana officinalis (NCBI:txid19953) Found in root (BTO:0001188). See: PubMed
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): GABA modulator
A substance that does not act as agonist or antagonist but does affect the gamma-aminobutyric acid receptor-ionophore complex. GABA-A receptors appear to have at least three allosteric sites at which modulators act: a site at which benzodiazepines act by increasing the opening frequency of gamma-aminobutyric acid-activated chloride channels; a site at which barbiturates act to prolong the duration of channel opening; and a site at which some steroids may act.
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
volatile oil component
Any plant metabolite that is found naturally as a component of a volatile oil.
Application(s): sedative
A central nervous system depressant used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.
GABA modulator
A substance that does not act as agonist or antagonist but does affect the gamma-aminobutyric acid receptor-ionophore complex. GABA-A receptors appear to have at least three allosteric sites at which modulators act: a site at which benzodiazepines act by increasing the opening frequency of gamma-aminobutyric acid-activated chloride channels; a site at which barbiturates act to prolong the duration of channel opening; and a site at which some steroids may act.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing valerenic acid (CHEBI:9921) has role GABA modulator (CHEBI:50268)
valerenic acid (CHEBI:9921) has role plant metabolite (CHEBI:76924)
valerenic acid (CHEBI:9921) has role sedative (CHEBI:35717)
valerenic acid (CHEBI:9921) has role volatile oil component (CHEBI:27311)
valerenic acid (CHEBI:9921) is a carbobicyclic compound (CHEBI:36785)
valerenic acid (CHEBI:9921) is a monocarboxylic acid (CHEBI:25384)
valerenic acid (CHEBI:9921) is a sesquiterpenoid (CHEBI:26658)
valerenic acid (CHEBI:9921) is conjugate acid of valerenate (CHEBI:68626)
Incoming valerenate (CHEBI:68626) is conjugate base of valerenic acid (CHEBI:9921)
IUPAC Name
(2E)-3-[(4S,7R,7aR)-3,7-dimethyl-2,4,5,6,7,7a-hexahydro-1H-inden-4-yl]-2-methylprop-2-enoic acid
Synonyms Sources
(−)-valerenic acid ChEBI
(2E)-3-[(4S,7R,7aR)-3,7-dimethyl-2,4,5,6,7,7a-hexahydro-1H-inden-4-yl]-2-methylacrylic acid IUPAC
Manual Xrefs Databases
C00003197 KNApSAcK
C09743 KEGG COMPOUND
US2012022283 Patent
Valerenic_acid Wikipedia
View more database links
Registry Numbers Types Sources
3138020 Reaxys Registry Number Reaxys
3569-10-6 CAS Registry Number KEGG COMPOUND
3569-10-6 CAS Registry Number ChemIDplus
3569-10-6 CAS Registry Number NIST Chemistry WebBook
Citations Waiting for Citations Types Sources
11817170 PubMed citation Europe PMC
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Last Modified
27 March 2015