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Mevalonic acid

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Mevalonic acid
Names
Preferred IUPAC name (3R)-3,5-Dihydroxy-3-methylpentanoic acid
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C6H12O4/c1-6(10,2-3-7)4-5(8)9/h7,10H,2-4H2,1H3,(H,8,9)/t6-/m1/s1Key: KJTLQQUUPVSXIM-ZCFIWIBFSA-N
  • InChI=1/C6H12O4/c1-6(10,2-3-7)4-5(8)9/h7,10H,2-4H2,1H3,(H,8,9)/t6-/m1/s1Key: KJTLQQUUPVSXIM-ZCFIWIBFBE
SMILES
  • C(O)(CCO)CC(=O)O
Properties
Chemical formula C6H12O4
Molar mass 148.158 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Mevalonic acid (MVA) is a key organic compound in biochemistry; the name is a contraction of dihydroxymethylvalerolactone. The carboxylate anion of mevalonic acid, which is the predominant form in biological environments, is known as mevalonate and is of major pharmaceutical importance. Drugs like statins (which lower levels of cholesterol) stop the production of mevalonate by inhibiting HMG-CoA reductase.

Chemistry

Mevalonic acid is very soluble in water and polar organic solvents. It exists in equilibrium with its lactone form, called mevalonolactone, that is formed by internal condensation of its terminal alcohol and carboxylic acid functional groups. Mevalonolactone acts to correct statin linked myopathy and limb girdle muscular disease caused by HMG CoA reductase mutation.

Biology

Mevalonic acid is a precursor in the biosynthetic pathway known as the mevalonate pathway that produces terpenes and steroids. Mevalonic acid is the primary precursor of isopentenyl pyrophosphate (IPP), that is in turn the basis for all terpenoids. Mevalonic acid is chiral and the (3R)-enantiomer is the only one that is biologically active.

Mevalonate pathway: The figure doesn't show that the HMG-CoA synthase needs another Acetyl-CoA as Substrate. Moreover, the enzyme that synthesizes mevalonic acid (HMG-CoA reductase) consumes two equivalents of NADH and releases one reduced CoA-SH.

References

  1. Endo, A. (1992). "The discovery and development of HMG-CoA reductase inhibitors". Journal of Lipid Research. 33 (11): 1569–1582. PMID 1464741.
  2. Yogev Y, Shorer Z, Koifman A, Wormser O, Drabkin M, Halperin D, Dolgin V, Proskorovski-Ohayon R, Hadar N, Davidov G, Nudelman H, Zarivach R, Shelef I, Perez Y, Birk OS (February 2023). "Limb girdle muscular disease caused by HMGCR mutation and statin myopathy treatable with mevalonolactone". Proc Natl Acad Sci U S A. 120 (7): e2217831120. doi:10.1073/pnas.2217831120. PMC 9963716. PMID 36745799.
Fatty acid metabolic intermediates
Synthesis
Degradation
Peroxisomal
Phytol
Other
Cholesterol and steroid metabolic intermediates
Mevalonate pathway
to HMG-CoA
Ketone bodies
to DMAPP
Geranyl-
Carotenoid
Non-mevalonate pathway
To Cholesterol
From Cholesterol
to Steroid hormones
Nonhuman
To Sitosterol
To Ergocalciferol
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