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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 17:34:11 UTC
Update Date2022-09-22 18:34:24 UTC
HMDB IDHMDB0030016
Secondary Accession Numbers
  • HMDB30016
Metabolite Identification
Common NameValerenic acid
DescriptionValerenic acid, also known as valerenate, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Based on a literature review a significant number of articles have been published on Valerenic acid.
Structure
Data?1563861925
Synonyms
ValueSource
ValerenateGenerator
IMUHMDB
(2E)-3-(3,7-Dimethyl-2,4,5,6,7,7a-hexahydro-1H-inden-4-yl)-2-methylprop-2-enoateGenerator
Chemical FormulaC15H22O2
Average Molecular Weight234.334
Monoisotopic Molecular Weight234.161979948
IUPAC Name(2E)-3-(3,7-dimethyl-2,4,5,6,7,7a-hexahydro-1H-inden-4-yl)-2-methylprop-2-enoic acid
Traditional Namevalerenic acid
CAS Registry Number3569-10-6
SMILES
CC1CCC(\C=C(/C)C(O)=O)C2=C(C)CCC12
InChI Identifier
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+
InChI KeyFEBNTWHYQKGEIQ-DHZHZOJOSA-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 DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point140 - 142 °CNot Available
Boiling Point374.00 to 375.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility0The Good Scents Company Information System
LogP5.188 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Polarizability26.97 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+157.88731661259
DarkChem[M-H]-155.79931661259
DeepCCS[M-2H]-194.97930932474
DeepCCS[M+Na]+170.54430932474
AllCCS[M+H]+155.532859911
AllCCS[M+H-H2O]+151.832859911
AllCCS[M+NH4]+159.032859911
AllCCS[M+Na]+160.032859911
AllCCS[M-H]-162.332859911
AllCCS[M+Na-2H]-162.532859911
AllCCS[M+HCOO]-163.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Valerenic acidCC1CCC(\C=C(/C)C(O)=O)C2=C(C)CCC123045.8Standard polar33892256
Valerenic acidCC1CCC(\C=C(/C)C(O)=O)C2=C(C)CCC121836.4Standard non polar33892256
Valerenic acidCC1CCC(\C=C(/C)C(O)=O)C2=C(C)CCC121815.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Valerenic acid,1TMS,isomer #1CC1=C2C(/C=C(\C)C(=O)O[Si](C)(C)C)CCC(C)C2CC11949.8Semi standard non polar33892256
Valerenic acid,1TBDMS,isomer #1CC1=C2C(/C=C(\C)C(=O)O[Si](C)(C)C(C)(C)C)CCC(C)C2CC12167.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Valerenic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a6r-2970000000-faf955331d2d52d6f5bf2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Valerenic acid GC-MS (1 TMS) - 70eV, Positivesplash10-004l-2390000000-eabd784d84c1e1c900e92017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Valerenic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Valerenic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Valerenic acid 10V, Positive-QTOFsplash10-00kr-0590000000-a785f5975e20573498812017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Valerenic acid 20V, Positive-QTOFsplash10-029i-2920000000-9b5ea2b85cfca509eebd2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Valerenic acid 40V, Positive-QTOFsplash10-0kas-5900000000-04bd3a0d24cc33998f342017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Valerenic acid 10V, Negative-QTOFsplash10-001i-0190000000-9bd08037c9a732194f632017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Valerenic acid 20V, Negative-QTOFsplash10-03ei-1950000000-0938af4600cdeb8b45f92017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Valerenic acid 40V, Negative-QTOFsplash10-00di-5910000000-8a729ac3d0b2c80cc6962017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Valerenic acid 10V, Positive-QTOFsplash10-029i-0960000000-5d5a27701726a3e27a372021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Valerenic acid 20V, Positive-QTOFsplash10-00kk-2920000000-b7acb01868f53a96c0fa2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Valerenic acid 40V, Positive-QTOFsplash10-0006-9300000000-a7d2c0158d2123f483ac2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Valerenic acid 10V, Negative-QTOFsplash10-001i-0490000000-643538f3213444302a702021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Valerenic acid 20V, Negative-QTOFsplash10-03e9-0950000000-fe98051c5cce95c9f5252021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Valerenic acid 40V, Negative-QTOFsplash10-06si-0940000000-c2e4b48bbe96ee5e4d912021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB001309
KNApSAcK IDC00003197
Chemspider ID4788689
KEGG Compound IDC09743
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkValerenic acid
METLIN IDNot Available
PubChem Compound6042891
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1442331
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.