NP-MRD: Showing NP-Card for Mevalonic acid (NP0000114)

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Record Information

Version

2.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2021-08-15 04:56:45 UTC

NP-MRD ID

NP0000114

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Mevalonic acid

Description

Mevalonic acid, also known as MVA, mevalonate, or hiochic acid, belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group. Mevalonic acid is a key organic compound in biochemistry. It is found in most higher organisms ranging from plants to animals. Mevalonic acid is a precursor in the biosynthetic pathway known as the mevalonate pathway that produces terpenes (in plants) and steroids (in animals). Mevalonic acid is the primary precursor of isopentenyl pyrophosphate (IPP), that is in turn the basis for all terpenoids. The production of mevalonic acid by the enzyme 3-hydroxy-3-methylglutaryl-coenzyme A (HMG-CoA) reductase, is the rate-limiting step in the biosynthesis of cholesterol (PMID: 12872277 ). The cholesterol biosynthetic pathway has three major steps: (1) Acetate to mevalonate, (2) mevalonate to squalene, and (3) squalene to cholesterol. In the first step, which catalyzed by thiolase, two acetyl-CoA molecules form acetoacetyl-CoA and one CoA molecule is released, then the acetoacetyl-CoA reacts with another molecule of acetyl-CoA and generates 3-hydroxy-3-methylglutaryl-CoA (HMGCoA). The enzyme responsible for this reaction is 3-hydroxy-3-methylglutaryl-CoA synthase (HMG-CoA synthase): In the pathway to synthesize cholesterol, one of the HMG-CoA carboxyl groups undergoes reduction to an alcohol, releasing CoA, leading to the formation of mevalonate, a six carbon compound. This reaction is catalyzed by hydroxy-methylglutaryl-CoA reductase, In the second step (mevalonate to squalene) mevalonate receives a phosphoryl group from ATP to form 5-phosphomevalonate. This compound accepts another phosphate to generate mevalonate-5-pyrophosphate. After a third phosphorylation, the compound is decarboxylated, loses water, and generates isopentenyl pyrophosphate (IPP). Then through successive condensations, IPP forms squalene, a terpene hydrocarbon that contains 30 carbon atoms. By cyclization and other changes, this compound will finally result in cholesterol. Mevalonic acid is found, on average, in the highest concentration within a few different foods, such as apples, corns, and wild carrots and in a lower concentration in garden tomato (var.), Pepper (C. Frutescens), and cucumbers. Mevalonic acid has also been detected, but not quantified in, several different foods, such as sweet oranges, potato, milk (cow), cabbages, and white cabbages. This could make mevalonic acid a potential biomarker for the consumption of these foods. Plasma concentrations and urinary excretion of MVA are decreased by HMG-CoA reductase inhibitor drugs such as pravastatin, simvastatin, and atorvastatin (PMID: 8808497 ).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol

Synonyms

Value	Source
(R)-3,5-Dihydroxy-3-methylvaleric acid	ChEBI
(R)-Mevalonate	ChEBI
3,5-Dihydroxy-3-methylvaleric acid	ChEBI
(R)-3,5-Dihydroxy-3-methylvalerate	Generator
(R)-Mevalonic acid	Generator
3,5-Dihydroxy-3-methylvalerate	Generator
Mevalonate	Generator
Acid, mevalonic	HMDB
(3R)-3,5-Dihydroxy-3-methylpentanoic acid	HMDB
(3R)-Mevalonic acid	HMDB
(R)-(-)-Mevalonic acid	HMDB
(R)-3,5-Dihydroxy-3-methylpentanoic acid	HMDB
2,4-Dideoxy-3-C-methylpentonic acid	HMDB
3,5-Dihydroxy-3-methylpentanoic acid	HMDB
Hiochic acid	HMDB
MVA	HMDB
R-Mevalonic acid	HMDB
beta,delta-Dihydroxy-beta-methylvaleric acid	HMDB
Β,δ-dihydroxy-β-methylvaleric acid	HMDB
Mevalonic acid	ChEBI

Chemical Formula

C₆H₁₂O₄

Average Mass

148.1571 Da

Monoisotopic Mass

148.07356 Da

IUPAC Name

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

Traditional Name

mevalonic acid

CAS Registry Number

150-97-0

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 Key

KJTLQQUUPVSXIM-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Allium cepa	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Arabidopsis thaliana	KNApSAcK Database	22123792
Asparagus officinalis	KNApSAcK Database	22123792
Aspergillus oryzae	LOTUS Database	35616633
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Brassica oleracea var. capitata	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Bubalus bubalis	FooDB	FooDB
Cannabis sativa	CannabisDB	Not Available
Capra aegagrus hircus	FooDB	FooDB
Capsicum annuum var. annuum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Chamaemelum nobile	KNApSAcK Database	22123792
Citrus X sinensis (L.) Osbeck (pro. sp.)	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Clausena lansium	KNApSAcK Database	22123792
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Cucumis sativus L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Daucus carota	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Daucus carota ssp. sativus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Gentiana straminea	KNApSAcK Database	22123792
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Malus pumila	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Matricaria recutita	KNApSAcK Database	22123792
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Momordica charantia	KNApSAcK Database	22123792
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Panax ginseng	KNApSAcK Database	22123792
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Pisum sativum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Polygonum minus	KNApSAcK Database	22123792
Rosmarinus officinalis	KNApSAcK Database	22123792
Salvia miltiorrhiza	KNApSAcK Database	22123792
Salvia rosmarinus	Plant	KNApSAcK
Salvia splendens	KNApSAcK Database	22123792
Santalum album	KNApSAcK Database	22123792
Sertia mussotii	-	KNApSAcK
Solanum lycopersicum var. lycopersicum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Solanum tuberosum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Streptomyces lividans	LOTUS Database	35616633
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB
Tripterygium wilfordii	KNApSAcK Database	22123792
Trypanosoma brucei	LOTUS Database	35616633
Zea mays L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases

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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Hydroxy 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 Framework

Aliphatic acyclic compounds

External Descriptors

mevalonic acid (CHEBI:17710 )
Hydroxy fatty acids (LMFA01050352 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	24 - 27 °C	https://pubchem.ncbi.nlm.nih.gov/compound/Mevalonic-acid#section=Color-Form
Boiling Point	Not Available	Not Available
Water Solubility	6 mg/mL	https://pubchem.ncbi.nlm.nih.gov/source/hsdb/7681#section=LogP
LogP	-0.58	https://pubchem.ncbi.nlm.nih.gov/compound/Mevalonic-acid#section=LogP

Predicted Properties

Property	Value	Source
Water Solubility	414 g/L	ALOGPS
logP	-0.9	ALOGPS
logP	-1.1	ChemAxon
logS	0.45	ALOGPS
pKa (Strongest Acidic)	4.38	ChemAxon
pKa (Strongest Basic)	-2.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	34.51 m³·mol⁻¹	ChemAxon
Polarizability	14.57 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0000227

DrugBank ID

DB03518

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Mevalonic_acid

METLIN ID

Not Available

PubChem Compound

439230

PDB ID

Not Available

ChEBI ID

17710

Good Scents ID

Not Available

References

General References

Houten SM, Kuis W, Duran M, de Koning TJ, van Royen-Kerkhof A, Romeijn GJ, Frenkel J, Dorland L, de Barse MM, Huijbers WA, Rijkers GT, Waterham HR, Wanders RJ, Poll-The BT: Mutations in MVK, encoding mevalonate kinase, cause hyperimmunoglobulinaemia D and periodic fever syndrome. Nat Genet. 1999 Jun;22(2):175-7. [PubMed:10369261 ]
Hoffmann G, Gibson KM, Brandt IK, Bader PI, Wappner RS, Sweetman L: Mevalonic aciduria--an inborn error of cholesterol and nonsterol isoprene biosynthesis. N Engl J Med. 1986 Jun 19;314(25):1610-4. [PubMed:3012338 ]
Dmitrieva NA, Perrun'kina AM, Khomulo PS: [Determination of mevalonic acid in the urine and its concentration in the urine of patients with atherosclerosis]. Vopr Med Khim. 1968 Jan-Feb;14(1):106-8. [PubMed:5683362 ]
Larson RA, Chung J, Scanu AM, Yachnin S: Neutrophils are required for the DNA synthetic response of human lymphocytes to mevalonic acid: evidence suggesting that a nonsterol product of mevalonate is involved. Proc Natl Acad Sci U S A. 1982 May;79(9):3028-32. [PubMed:6953445 ]
Siavoshian S, Simoneau C, Maugeais P, Marks L, Rodary L, Gardette J, Krempf M: Measurement of mevalonic acid in human urine by bench top gas chromatography-mass spectrometry. Clin Chim Acta. 1995 Dec 29;243(2):129-36. [PubMed:8747489 ]
Mitchell ED Jr, Avigan J: Control of phosphorylation and decarboxylation of mevalonic acid and its metabolites in cultured human fibroblasts and in rat liver in vivo. J Biol Chem. 1981 Jun 25;256(12):6170-3. [PubMed:6263908 ]
Abrar M, Martin PD: Validation and application of an assay for the determination of mevalonic acid in human plasma by liquid chromatography tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2002 Jun 25;773(2):103-11. [PubMed:12031835 ]
Haas D, Kelley RI, Hoffmann GF: Inherited disorders of cholesterol biosynthesis. Neuropediatrics. 2001 Jun;32(3):113-22. [PubMed:11521206 ]
Larson RA, Kluskens LE, Yachnin S: The DNA synthetic response of normal and abnormal human lymphocytes to mevalonic acid: the role of granulocytes as a helper population. J Allergy Clin Immunol. 1984 Sep;74(3 Pt 1):280-90. [PubMed:6236250 ]
Larson RA, Yachnin S: Mevalonic acid induces DNA synthesis in chronic lymphocytic leukemia cells. Blood. 1984 Jul;64(1):257-62. [PubMed:6610447 ]
Parker TS, McNamara DJ, Brown CD, Kolb R, Ahrens EH Jr, Alberts AW, Tobert J, Chen J, De Schepper PJ: Plasma mevalonate as a measure of cholesterol synthesis in man. J Clin Invest. 1984 Sep;74(3):795-804. [PubMed:6565710 ]
Hoffmann GF, Sweetman L, Bremer HJ, Hunneman DH, Hyanek J, Kozich V, Lehnert W, Nyhan WL, Speidel I, Trefz FK, et al.: Facts and artefacts in mevalonic aciduria: development of a stable isotope dilution GCMS assay for mevalonic acid and its application to physiological fluids, tissue samples, prenatal diagnosis and carrier detection. Clin Chim Acta. 1991 May 15;198(3):209-27. [PubMed:1653652 ]
Jemal M, Schuster A, Whigan DB: Liquid chromatography/tandem mass spectrometry methods for quantitation of mevalonic acid in human plasma and urine: method validation, demonstration of using a surrogate analyte, and demonstration of unacceptable matrix effect in spite of use of a stable isotope analog internal standard. Rapid Commun Mass Spectrom. 2003;17(15):1723-34. [PubMed:12872277 ]
Lindenthal B, von Bergmann K: Urinary excretion and serum concentration of mevalonic acid during acute intake of alcohol. Metabolism. 2000 Jan;49(1):62-6. [PubMed:10647065 ]
Naoumova RP, Marais AD, Mountney J, Firth JC, Rendell NB, Taylor GW, Thompson GR: Plasma mevalonic acid, an index of cholesterol synthesis in vivo, and responsiveness to HMG-CoA reductase inhibitors in familial hypercholesterolaemia. Atherosclerosis. 1996 Jan 26;119(2):203-13. doi: 10.1016/0021-9150(95)05649-1. [PubMed:8808497 ]

Showing NP-Card for Mevalonic acid (NP0000114)

MOL for NP0000114 (Mevalonic acid)

3D MOL for NP0000114 (Mevalonic acid)

3D SDF for NP0000114 (Mevalonic acid)

3D-SDF for NP0000114 (Mevalonic acid)

PDB for NP0000114 (Mevalonic acid)

3D PDB for NP0000114 (Mevalonic acid)

SMILES for NP0000114 (Mevalonic acid)

INCHI for NP0000114 (Mevalonic acid)

Structure for NP0000114 (Mevalonic acid)

3D Structure for NP0000114 (Mevalonic acid)