Mevalonic acid

Names

IUPAC name

(3R)-3,5-Dihydroxy-3-methylpentanoic acid

Identifiers

CAS Number

150-97-0^Y

3D model (Jmol)

CHEBI:17710^N

388367^N

C00418^N

InChI=1S/C6H12O4/c1-6(10,2-3-7)4-5(8)9/h7,10H,2-4H2,1H3,(H,8,9)/t6-/m1/s1^N
Key: KJTLQQUUPVSXIM-ZCFIWIBFSA-N^N
InChI=1/C6H12O4/c1-6(10,2-3-7)4-5(8)9/h7,10H,2-4H2,1H3,(H,8,9)/t6-/m1/s1
Key: KJTLQQUUPVSXIM-ZCFIWIBFBE

SMILES

C[C@@](O)(CCO)CC(=O)O

Properties

Chemical formula

C₆H₁₂O₄

Molar mass

148.16 g·mol⁻¹

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

verify (what is ^YN ?)

Infobox references

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 such as the statins (which lower levels of cholesterol) stop the production of mevalonate by inhibiting HMG-CoA reductase.^[1]

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.

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

References

↑ Endo, A. (1992). "The discovery and development of HMG-CoA reductase inhibitors". Journal of Lipid Research. 33 (11): 1569–1582. PMID 1464741.

Cholesterol and steroid metabolic intermediates

Mevalonate pathway

to HMG-CoA	Acetyl-CoA Acetoacetyl-CoA HMB HMB-CoA HMG-CoA

Ketone bodies	Acetone Acetoacetic acid β-Hydroxybutyric acid

to DMAPP	Mevalonic acid Phosphomevalonic acid 5-Diphosphomevalonic acid Isopentenyl pyrophosphate Dimethylallyl pyrophosphate

Geranyl-	Geranyl pyrophosphate Geranylgeranyl pyrophosphate

Carotenoid	Prephytoene diphosphate Phytoene

Non-mevalonate pathway

To Cholesterol

From Cholesterol
(to steroids)

Steroid hormones

See here instead.

Nonhuman

Phytosterols	Stigmasterol Brassicasterol

Ergosterols	Ergosterol Ergocalciferol

Authority control	NDL: 00563239

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