Record Information
Version1.0
Creation date2010-04-08 22:06:32 UTC
Update date2019-11-26 03:00:22 UTC
Primary IDFDB005126
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameMevalonic acid
DescriptionMevalonic acid (MVA) is a key organic compound in biochemistry. The anion of mevalonic acid, the predominant form in biological media, is known as mevalonate. This compound is of major pharmaceutical importance. Drugs, such as the statins, stop the production of mevalonate by inhibiting HMG-CoA reductase. [Wikipedia]. Mevalonic acid is found in many foods, some of which are pepper (c. frutescens), cabbage, wild carrot, and white cabbage.
CAS Number150-97-0
Structure
Thumb
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility414 g/LALOGPS
logP-0.9ALOGPS
logP-1.1ChemAxon
logS0.45ALOGPS
pKa (Strongest Acidic)4.38ChemAxon
pKa (Strongest Basic)-2.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity34.51 m³·mol⁻¹ChemAxon
Polarizability14.57 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC6H12O4
IUPAC name(3R)-3,5-dihydroxy-3-methylpentanoic acid
InChI IdentifierInChI=1S/C6H12O4/c1-6(10,2-3-7)4-5(8)9/h7,10H,2-4H2,1H3,(H,8,9)/t6-/m1/s1
InChI KeyKJTLQQUUPVSXIM-ZCFIWIBFSA-N
Isomeric SMILESC[C@@](O)(CCO)CC(O)=O
Average Molecular Weight148.1571
Monoisotopic Molecular Weight148.073558872
Classification
Description Belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentHydroxy fatty acids
Alternative Parents
Substituents
  • Branched fatty acid
  • Hydroxy fatty acid
  • Short-chain hydroxy acid
  • Methyl-branched fatty acid
  • Tertiary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Organic oxide
  • Alcohol
  • Carbonyl group
  • Organooxygen compound
  • Primary alcohol
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSMevalonic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0f79-9400000000-1432953ab200e13ed3a7Spectrum
Predicted GC-MSMevalonic acid, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00bj-9372000000-2a6b263d37306947c327Spectrum
Predicted GC-MSMevalonic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSMevalonic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0002-2900000000-d1dc97020c103f2a916b2020-04-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-014i-9000000000-b4dc45e964aee6759d932020-04-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-014i-9100000000-98f7e8ee013680f4f6102020-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01q9-2900000000-00a30c20b0fe2afce7d82016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03ej-9700000000-c6f9687555150d5ef1a72016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01bi-9100000000-7047d67f0ba1f8aa28ef2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f72-3900000000-0f765b34011b73405add2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-9500000000-dd24fe04989af5af11512016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052s-9100000000-251b958b3e4355c6f2f62016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0fbj-2900000000-fb0c642b03cb9422a9e42021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4r-9300000000-1b45622114c4f19f4a9a2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-42ee087c307b5e92b0592021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01qa-3900000000-2c25572adb25887608452021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000j-9200000000-b6d834223509e1430e612021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-e4b7f6f9a91f771bd4532021-09-24View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
ChemSpider ID436
ChEMBL IDNot Available
KEGG Compound IDC00418
Pubchem Compound ID449
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00227
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDMEVALONIC-ACID
BIGG ID34923
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDMevalonic_acid
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Milk (Cow)Expected but not quantifiedNot Available26686724
Apple3.300 - 3.300 mg/100 g3.300 mg/100 gDUKE
CabbageExpected but not quantifiedNot AvailableDUKE
Carrot0.40000 - 0.40000 mg/100 g0.40000 mg/100 gDUKE
Common peaExpected but not quantifiedNot AvailableDUKE
Corn1.400 - 1.400 mg/100 g1.400 mg/100 gDUKE
Cucumber0.30000 - 0.30000 mg/100 g0.30000 mg/100 gDUKE
Garden onion0.05000 - 0.05000 mg/100 g0.05000 mg/100 gDUKE
Garden tomato (var.)0.35000 - 0.35000 mg/100 g0.35000 mg/100 gDUKE
Pepper (C. frutescens)0.05000 - 0.05000 mg/100 g0.05000 mg/100 gDUKE
Showing 1 to 10 of 43 entries
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
Pathways
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).