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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-10-30 10:32:48 UTC
Update Date2017-12-07 15:43:48 UTC
HMDB IDHMDB0059629
Secondary Accession Numbers
  • HMDB59629
Metabolite Identification
Common Name(R)-mevalonate
Description(r)-mevalonate is part of the Metabolic intermediate biosynthesis, Terpenoid backbone biosynthesis, Bile secretion, Isoprenoid biosynthesis, and Peroxisome pathways. It is a substrate for: 3-hydroxy-3-methylglutaryl-coenzyme A reductase, and Mevalonate kinase.
Structure
Thumb
Synonyms
ValueSource
DL-Mevalonic acidChEBI
MVAChEBI
RS-Mevalonic acidChEBI
DL-MevalonateGenerator
MevalonateGenerator
RS-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
Chemical FormulaC6H12O4
Average Molecular Weight148.1571
Monoisotopic Molecular Weight148.073558872
IUPAC Name3,5-dihydroxy-3-methylpentanoic acid
Traditional NameDL-mevalonic acid
CAS Registry NumberNot Available
SMILES
C[C@@](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)/t6-/m1/s1
InChI KeyKJTLQQUUPVSXIM-ZCFIWIBFSA-N
Chemical Taxonomy
DescriptionThis compound 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:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
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
Polarizability14.54 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f79-9400000000-875fe9eef6c0fc4dbd86View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00bj-9372000000-2a6b263d37306947c327View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0002-2900000000-d1dc97020c103f2a916bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-014i-9000000000-b4dc45e964aee6759d93View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-014i-9100000000-98f7e8ee013680f4f610View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01q9-1900000000-0bb212794cd101490acdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01q1-9800000000-95e2c177f1ee0c9cd312View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-02g9-9200000000-f5d0630f14fa9249d4c9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f92-2900000000-8b015723cd087b29e974View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-9800000000-93639d7d95cd6690d44dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4s-9100000000-094b07bf98ce319b4824View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB005126
KNApSAcK IDNot Available
Chemspider ID436
KEGG Compound IDC00418
BioCyc IDMEVALONATE
BiGG ID34923
Wikipedia LinkMevalonic acid
METLIN ID127
PubChem Compound449
PDB IDNot Available
ChEBI ID25351
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. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Enzymes

General function:
Involved in hydroxymethylglutaryl-CoA reductase (NADPH) activity
Specific function:
Transmembrane glycoprotein that is the rate-limiting enzyme in cholesterol biosynthesis as well as in the biosynthesis of nonsterol isoprenoids that are essential for normal cell function including ubiquinone and geranylgeranyl proteins.
Gene Name:
HMGCR
Uniprot ID:
P04035
Molecular weight:
97475.155
Reactions
(R)-mevalonate + Coenzyme A + NADP → 3-Hydroxy-3-methylglutaryl-CoA + NADPHdetails
(R)-mevalonate + Coenzyme A + NADP → 3-Hydroxy-3-methylglutaryl-CoA + NADPH + Hydrogen Iondetails
General function:
Involved in ATP binding
Specific function:
May be a regulatory site in cholesterol biosynthetic pathway.
Gene Name:
MVK
Uniprot ID:
Q03426
Molecular weight:
42450.475
Reactions
Adenosine triphosphate + (R)-mevalonate → ADP + Mevalonic acid-5Pdetails