Showing metabocard for Mevalonic acid (BMDB0000227)

IdentificationTaxonomyPhysical propertiesSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:27:04 UTC
Update Date2020-05-21 16:28:43 UTC
MCDB ID BMDB0000227
Secondary Accession Numbers
  • BMDB00227
Metabolite Identification
Common NameMevalonic acid
Description(R)-Mevalonic acid, also known as DL-mevalonate or MVA, belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group (R)-Mevalonic acid exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule (R)-Mevalonic acid exists in all living species, ranging from bacteria to humans (R)-Mevalonic acid is a potentially toxic compound.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
DL-Mevalonic acidChEBI
MVAChEBI
RS-Mevalonic acidChEBI
DL-MevalonateGenerator
RS-MevalonateGenerator
MevalonateGenerator
(3Rs)-MevalonateHMDB
(3Rs)-Mevalonic acidHMDB
2,4-Dideoxy-3-C-methylpentonateHMDB
2,4-Dideoxy-3-C-methylpentonic acidHMDB
3,5-Dihydroxy-3-methyl-valerateHMDB
3,5-Dihydroxy-3-methyl-valeric acidHMDB
3,5-Dihydroxy-3-methylpentanoateHMDB
3,5-Dihydroxy-3-methylpentanoic acidHMDB
3,5-Dihydroxy-3-methylvalerateHMDB
3,5-Dihydroxy-3-methylvaleric acidHMDB
b,D-Dihydroxy-b-methylvalerateHMDB
b,D-Dihydroxy-b-methylvaleric acidHMDB
b,D-Dihydroxy-beta-methylvalerateHMDB
b,D-Dihydroxy-beta-methylvaleric acidHMDB
Hiochic acidHMDB
MK 91HMDB
MVSHMDB
Acid, mevalonicMeSH, HMDB
(R)-MevalonateGenerator, HMDB
Mevalonic acidMeSH
Chemical FormulaC6H12O4
Average Molecular Weight148.1571
Monoisotopic Molecular Weight148.073558872
IUPAC Name3,5-dihydroxy-3-methylpentanoic acid
Traditional NameRS-mevalonic acid
CAS Registry Number150-97-0
SMILES
CC(O)(CCO)CC(O)=O
InChI Identifier
InChI=1S/C6H12O4/c1-6(10,2-3-7)4-5(8)9/h7,10H,2-4H2,1H3,(H,8,9)
InChI KeyKJTLQQUUPVSXIM-UHFFFAOYSA-N
Chemical Taxonomy
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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point24 - 27 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
Polarizability14.54 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f79-9400000000-875fe9eef6c0fc4dbd862017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00bj-9372000000-2a6b263d37306947c3272017-10-06View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0002-2900000000-d1dc97020c103f2a916b2012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-014i-9000000000-b4dc45e964aee6759d932012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-014i-9100000000-98f7e8ee013680f4f6102012-07-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01q9-1900000000-0bb212794cd101490acd2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01q1-9800000000-95e2c177f1ee0c9cd3122017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-02g9-9200000000-f5d0630f14fa9249d4c92017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f92-2900000000-8b015723cd087b29e9742017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-9800000000-93639d7d95cd6690d44d2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4s-9100000000-094b07bf98ce319b48242017-09-01View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Not Available2012-12-04View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Not Available2012-12-05View Spectrum
Concentrations
StatusValueReferenceDetails
Detected but not QuantifiedNot Applicable details
HMDB IDHMDB0000227
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMevalonic acid
METLIN IDNot Available
PubChem Compound449
PDB IDNot Available
ChEBI ID25351
References
Synthesis ReferenceTakahara, Kenji; Nakamura, Yoshio; Ohashi, Takehisa; Watanabe, Kiyoshi. Fermentative production of mevalonic acid. Jpn. Kokai Tokkyo Koho (1985), 4 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Hagi T, Kobayashi M, Nomura M: Metabolome analysis of milk fermented by gamma-aminobutyric acid-producing Lactococcus lactis. J Dairy Sci. 2016 Feb;99(2):994-1001. doi: 10.3168/jds.2015-9945. Epub 2015 Dec 10. [PubMed:26686724 ]