Mevalonic acid

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Mevalonic acid


IUPAC name (3R)-3,5-Dihydroxy-3-methylpentanoic acid
Identifiers
CAS number	150-97-0
PubChem	439230
	Jmol-3D images	{{#if:C[C@@](O)(CCO)CC(=O)O\|Image 1
SMILES C[C@@](O)(CCO)CC(=O)O
Properties
Molecular formula	C₆H₁₂O₄
Molar mass	148.16 g mol⁻¹
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Mevalonic acid (MVA) (derived from a contraction of dihydroxymethylvalerolactone) 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.^[1]

Chemistry

Mevalonic acid is very soluble in water and in polar organic solvents. It exists in equilibrium with the lactone, called mevalonolactone, 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 HMG-CoA

Ketone bodies	Acetone Acetoacetic acid beta-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

DOXP
MEP
CDP-ME
CDP-MEP
MEcPP
HMB-PP
IPP
DMAPP

To Cholesterol

From Cholesterol
(to steroids)

Steroid hormones

Corticosteroids
(C21 pregnane)

Mineralocorticoids	Pregnenolone Progesterone Cortodoxone Corticosterone Aldosterone

Glucocorticoids	Pregnenolone 17-Hydroxypregnenolone 17-Hydroxyprogesterone Cortisol Cortisol Cortisone

Sex steroids

Androgens (C19 androstane)	DHEA Androstenedione/5-Androstenediol Testosterone Dihydrotestosterone DHEA sulfate Epitestosterone

Estrogens (C18 estrane)	Estetrol Estrone Estradiol Estriol

Nonhuman

Phytosterols	Stigmasterol Brassicasterol

Ergosterols	Ergosterol Ergocalciferol

M: MET

mt, k, c/g/r/p/y/i, f/h/s/l/o/e, a/u, n, m

k, cgrp/y/i, f/h/s/l/o/e, au, n, m, epon

m (A16/C10), i (k, c/g/r/p/y/i, f/h/s/o/e, a/u, n, m)

M: END

anat/phys/devp/horm

noco (d)/cong/tumr, sysi/epon

proc, drug (A10/H1/H2/H3/H5)

Biochemical families: carbohydrates
- alcohols
- glycoproteins
- glycosides
lipids
- eicosanoids
- fatty acids / intermediates
- phospholipids
- sphingolipids
- steroids
nucleic acids
- constituents / intermediates
proteins
- Amino acids / intermediates
tetrapyrroles / intermediates

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