CHEBI:9921 - valerenic acid

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
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.
Supplier Information
Download Molfile XML SDF
Wikipedia License
Waiting for wikipedia content
Read full article at Wikipedia
Formula C15H22O2
Net Charge 0
Average Mass 234.33400
Monoisotopic Mass 234.162
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:19953) 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 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
Database Links 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
17340394 PubMed citation Europe PMC
18095218 PubMed citation Europe PMC
18164718 PubMed citation Europe PMC
18602406 PubMed citation Europe PMC
18704879 PubMed citation Europe PMC
19156843 PubMed citation Europe PMC
19178294 PubMed citation Europe PMC
20042323 PubMed citation Europe PMC
20235267 PubMed citation Europe PMC
20878691 PubMed citation Europe PMC
21154200 PubMed citation Europe PMC
21584239 PubMed citation Europe PMC
21641881 PubMed citation Europe PMC
21894886 PubMed citation Europe PMC
22411722 PubMed citation Europe PMC
22776156 PubMed citation Europe PMC
22923195 PubMed citation Europe PMC
22944521 PubMed citation Europe PMC
Last Modified
27 March 2015