Valerenic acid (CHEM017410)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 04:19:15 UTC
Update Date2016-11-09 01:15:35 UTC
Accession NumberCHEM017410
Identification
Common NameValerenic acid
ClassSmall Molecule
DescriptionA 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.
Contaminant Sources
  • FooDB Chemicals
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(-)-Valerenic acidChEBI
(2E)-3-[(4S,7R,7AR)-3,7-dimethyl-2,4,5,6,7,7a-hexahydro-1H-inden-4-yl]-2-methylacrylic acidChEBI
(-)-ValerenateGenerator
(2E)-3-[(4S,7R,7AR)-3,7-dimethyl-2,4,5,6,7,7a-hexahydro-1H-inden-4-yl]-2-methylacrylateGenerator
ValerenateGenerator
(e)-3-[(4S,7R,7Ar)-3,7-dimethyl-2,4,5,6,7,7a-hexahydro-1H-inden-4-yl]-2-methylprop-2-enoateGenerator
Valerenic acidMeSH
Chemical FormulaC15H22O2
Average Molecular Mass234.339 g/mol
Monoisotopic Mass234.162 g/mol
CAS Registry Number3569-10-6
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
Traditional 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
SMILES[H]\C(=C(\C)C(O)=O)[C@]1([H])CC[C@@]([H])(C)[C@@]2([H])CCC(C)=C12
InChI IdentifierInChI=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
InChI KeyFEBNTWHYQKGEIQ-SUKRRCERSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentSesquiterpenoids
Alternative Parents
Substituents
  • Sesquiterpenoid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.14 g/LALOGPS
logP4.15ALOGPS
logP3.6ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)5.06ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity70.05 m³·mol⁻¹ChemAxon
Polarizability26.96 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-1790000000-9891caa4cf52495978c3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01pa-2910000000-965debf4c514b5e4738aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-053s-4900000000-c4775fba5cf23b9a20afSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0190000000-05872e2872ac84bc5fe0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01q0-1940000000-2ddf4809cc8ac389bde4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-5920000000-610190d34da1a30fe344Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDC00003197
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkValerenic_acid
Chemspider IDNot Available
ChEBI ID9921
PubChem Compound ID6440940
Kegg Compound IDC09743
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11817170
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=17340394
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=18095218
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=18164718
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=18602406
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=18704879
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=19156843
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=19178294
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=20042323
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=20235267
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=20878691
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=21154200
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=21584239
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=21641881
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=21894886
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=22411722
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=22776156
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=22923195
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=22944521