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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2) Show 2 proteins XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2023-02-21 17:14:38 UTC

HMDB ID

HMDB0000227

Secondary Accession Numbers

HMDB00227
HMDB0059629
HMDB59629

Metabolite 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 View Stereo Labels

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
Mevalonic acid	ChEBI
Acid, mevalonic	MeSH
(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

Chemical Formula

C₆H₁₂O₄

Average Molecular Weight

148.1571

Monoisotopic Molecular Weight

148.073558872

IUPAC Name

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

Traditional Name

mevalonic acid

CAS Registry Number

17817-88-8

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 Key

KJTLQQUUPVSXIM-ZCFIWIBFSA-N

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 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Organelle

Peroxisome (HMDB: HMDB0000227)
Endoplasmic reticulum (HMDB: HMDB0000227)
Adiposome (HMDB: HMDB0000227)

Cell

Fibroblasts (HMDB: HMDB0000227)
Leukocyte (HMDB: HMDB0000227)

Non-excretory biofluid

Biofluid or Excreta

Lymph (HMDB: HMDB0000227)
Blood (PMID: 10947201)
Saliva (PMID: 31026179)

Organ

Liver (HMDB: HMDB0000227)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0000227)
Feces (PMID: 27543620)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0000227)

Source

Exogenous

Food

Food (HMDB: HMDB0000227)

Animal origin

Poultry

Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)
Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)

Equine

Horse (FooDB: FOOD00378)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Fruit

Pome

Apple (FooDB: FOOD00105)

Citrus

Sweet orange (FooDB: FOOD00057)

Vegetable

Root vegetable

Carrot (FooDB: FOOD00245)
Wild carrot (FooDB: FOOD00072)

Tuber

Potato (FooDB: FOOD00175)

Onion-family vegetable

Garden onion (FooDB: FOOD00006)

Cabbage

White cabbage (FooDB: FOOD00887)
Cabbage (FooDB: FOOD00851)

Fruit vegetable

Garden tomato (var.) (FooDB: FOOD00173)
Pepper (C. frutescens) (FooDB: FOOD00428)

Cereal and cereal product

Cereal

Corn (FooDB: FOOD00205)

Gourd

Cucumber (FooDB: FOOD00065)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Pulse

Pea

Common pea (FooDB: FOOD00141)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Steroid Biosynthesis (HMDB: HMDB0000227)
Terpenoid Backbone Biosynthesis (PathBank: SMP0002384)
Cholesterol Biosynthesis and Metabolism CE(14:0) (PathBank: SMP0002435)
Cholesterol Biosynthesis and Metabolism CE(10:0) (PathBank: SMP0002436)
Cholesterol Biosynthesis and Metabolism CE(12:0) (PathBank: SMP0002438)
Cholesterol Biosynthesis and Metabolism CE(16:0) (PathBank: SMP0002440)
Cholesterol Biosynthesis and Metabolism CE(18:0) (PathBank: SMP0002441)
Cholesterol Biosynthesis and Metabolism (PathBank: SMP0070041)
Fatty Acid Metabolism (HMDB: HMDB0000227)
Steroid Biosynthesis (PathBank: SMP0002381)

Disease pathway

Cholesteryl Ester Storage Disease (PathBank: SMP0000508)
Hyper-IgD Syndrome (PathBank: SMP0000509)
Mevalonic Aciduria (PathBank: SMP0000510)
Wolman Disease (PathBank: SMP0000511)
Smith-Lemli-Opitz Syndrome (SLOS) (PathBank: SMP0000389)
CHILD Syndrome (PathBank: SMP0000387)
Desmosterolosis (PathBank: SMP0000386)
Chondrodysplasia Punctata II, X-Linked Dominant (CDPX2) (PathBank: SMP0000388)
Lysosomal Acid Lipase Deficiency (Wolman Disease) (PathBank: SMP0000319)
Hypercholesterolemia (PathBank: SMP0000209)

Drug action pathway

Ibandronate Action Pathway (PathBank: SMP0000079)
Simvastatin Action Pathway (PathBank: SMP0000082)
Pravastatin Action Pathway (PathBank: SMP0000089)
Rosuvastatin Action Pathway (PathBank: SMP0000092)
Alendronate Action Pathway (PathBank: SMP0000095)
Lovastatin Action Pathway (PathBank: SMP0000099)
Zoledronate Action Pathway (PathBank: SMP0000107)
Cerivastatin Action Pathway (PathBank: SMP0000111)
Risedronate Action Pathway (PathBank: SMP0000112)
Pamidronate Action Pathway (PathBank: SMP0000117)
Fluvastatin Action Pathway (PathBank: SMP0000119)
Atorvastatin Action Pathway (PathBank: SMP0000131)

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0000227)

Biochemical process

Lipid transport (HMDB: HMDB0000227)

Role

Biological role

Energy storage (HMDB: HMDB0000227)

Industrial application

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0000227)

Biomarker

Mevalonic aciduria (MarkerDB: MDB00000109)
Smith-Lemli-Opitz syndrome (MarkerDB: MDB00000109)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	24 - 27 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	Astarita_neg	127.0	30932474
[M-H]-	Baker	133.983	30932474
[M-H]-	MetCCS_test_neg	125.8	30932474
[M-H]-	Not Available	129.9	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000280
[M-H]-	Not Available	129.4	http://allccs.zhulab.cn/database/detail?ID=AllCCS00002149

Predicted Molecular 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	133.536	31661259
DarkChem	[M-H]-	127.993	31661259
AllCCS	[M+H]+	133.967	32859911
AllCCS	[M-H]-	130.349	32859911
DeepCCS	[M+H]+	126.814	30932474
DeepCCS	[M-H]-	122.984	30932474
DeepCCS	[M-2H]-	159.809	30932474
DeepCCS	[M+Na]+	135.381	30932474
AllCCS	[M+H]+	134.0	32859911
AllCCS	[M+H-H2O]+	130.0	32859911
AllCCS	[M+NH4]+	137.7	32859911
AllCCS	[M+Na]+	138.8	32859911
AllCCS	[M-H]-	130.3	32859911
AllCCS	[M+Na-2H]-	132.7	32859911
AllCCS	[M+HCOO]-	135.3	32859911

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Mevalonic acid,1TMS,isomer #1	C[C@@](CCO)(CC(=O)O)O[Si](C)(C)C	1427.7	Semi standard non polar	33892256
Mevalonic acid,1TMS,isomer #1	C[C@@](CCO)(CC(=O)O)O[Si](C)(C)C	1301.0	Standard non polar	33892256
Mevalonic acid,1TMS,isomer #1	C[C@@](CCO)(CC(=O)O)O[Si](C)(C)C	1918.3	Standard polar	33892256
Mevalonic acid,1TMS,isomer #2	C[C@@](O)(CCO[Si](C)(C)C)CC(=O)O	1425.3	Semi standard non polar	33892256
Mevalonic acid,1TMS,isomer #2	C[C@@](O)(CCO[Si](C)(C)C)CC(=O)O	1323.7	Standard non polar	33892256
Mevalonic acid,1TMS,isomer #2	C[C@@](O)(CCO[Si](C)(C)C)CC(=O)O	1919.9	Standard polar	33892256
Mevalonic acid,1TMS,isomer #3	C[C@@](O)(CCO)CC(=O)O[Si](C)(C)C	1386.5	Semi standard non polar	33892256
Mevalonic acid,1TMS,isomer #3	C[C@@](O)(CCO)CC(=O)O[Si](C)(C)C	1324.3	Standard non polar	33892256
Mevalonic acid,1TMS,isomer #3	C[C@@](O)(CCO)CC(=O)O[Si](C)(C)C	1909.2	Standard polar	33892256
Mevalonic acid,2TMS,isomer #1	C[C@@](CCO[Si](C)(C)C)(CC(=O)O)O[Si](C)(C)C	1532.2	Semi standard non polar	33892256
Mevalonic acid,2TMS,isomer #1	C[C@@](CCO[Si](C)(C)C)(CC(=O)O)O[Si](C)(C)C	1448.1	Standard non polar	33892256
Mevalonic acid,2TMS,isomer #1	C[C@@](CCO[Si](C)(C)C)(CC(=O)O)O[Si](C)(C)C	1667.7	Standard polar	33892256
Mevalonic acid,2TMS,isomer #2	C[C@@](CCO)(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C	1467.8	Semi standard non polar	33892256
Mevalonic acid,2TMS,isomer #2	C[C@@](CCO)(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C	1460.0	Standard non polar	33892256
Mevalonic acid,2TMS,isomer #2	C[C@@](CCO)(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C	1658.8	Standard polar	33892256
Mevalonic acid,2TMS,isomer #3	C[C@@](O)(CCO[Si](C)(C)C)CC(=O)O[Si](C)(C)C	1474.9	Semi standard non polar	33892256
Mevalonic acid,2TMS,isomer #3	C[C@@](O)(CCO[Si](C)(C)C)CC(=O)O[Si](C)(C)C	1475.4	Standard non polar	33892256
Mevalonic acid,2TMS,isomer #3	C[C@@](O)(CCO[Si](C)(C)C)CC(=O)O[Si](C)(C)C	1672.1	Standard polar	33892256
Mevalonic acid,3TMS,isomer #1	C[C@@](CCO[Si](C)(C)C)(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C	1556.0	Semi standard non polar	33892256
Mevalonic acid,3TMS,isomer #1	C[C@@](CCO[Si](C)(C)C)(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C	1567.1	Standard non polar	33892256
Mevalonic acid,3TMS,isomer #1	C[C@@](CCO[Si](C)(C)C)(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C	1497.3	Standard polar	33892256
Mevalonic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@](C)(CCO)CC(=O)O	1662.6	Semi standard non polar	33892256
Mevalonic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@](C)(CCO)CC(=O)O	1502.3	Standard non polar	33892256
Mevalonic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@](C)(CCO)CC(=O)O	1958.2	Standard polar	33892256
Mevalonic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OCC[C@@](C)(O)CC(=O)O	1660.2	Semi standard non polar	33892256
Mevalonic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OCC[C@@](C)(O)CC(=O)O	1517.5	Standard non polar	33892256
Mevalonic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OCC[C@@](C)(O)CC(=O)O	2021.4	Standard polar	33892256
Mevalonic acid,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)C[C@](C)(O)CCO	1613.0	Semi standard non polar	33892256
Mevalonic acid,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)C[C@](C)(O)CCO	1521.2	Standard non polar	33892256
Mevalonic acid,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)C[C@](C)(O)CCO	1985.8	Standard polar	33892256
Mevalonic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC[C@](C)(CC(=O)O)O[Si](C)(C)C(C)(C)C	1977.3	Semi standard non polar	33892256
Mevalonic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC[C@](C)(CC(=O)O)O[Si](C)(C)C(C)(C)C	1865.3	Standard non polar	33892256
Mevalonic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC[C@](C)(CC(=O)O)O[Si](C)(C)C(C)(C)C	1903.4	Standard polar	33892256
Mevalonic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C[C@@](C)(CCO)O[Si](C)(C)C(C)(C)C	1912.7	Semi standard non polar	33892256
Mevalonic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C[C@@](C)(CCO)O[Si](C)(C)C(C)(C)C	1900.9	Standard non polar	33892256
Mevalonic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C[C@@](C)(CCO)O[Si](C)(C)C(C)(C)C	1883.7	Standard polar	33892256
Mevalonic acid,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OCC[C@@](C)(O)CC(=O)O[Si](C)(C)C(C)(C)C	1911.8	Semi standard non polar	33892256
Mevalonic acid,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OCC[C@@](C)(O)CC(=O)O[Si](C)(C)C(C)(C)C	1889.2	Standard non polar	33892256
Mevalonic acid,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OCC[C@@](C)(O)CC(=O)O[Si](C)(C)C(C)(C)C	1916.1	Standard polar	33892256
Mevalonic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC[C@](C)(CC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2208.2	Semi standard non polar	33892256
Mevalonic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC[C@](C)(CC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2159.8	Standard non polar	33892256
Mevalonic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC[C@](C)(CC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1917.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Mevalonic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f79-9400000000-1432953ab200e13ed3a7	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Mevalonic acid GC-MS (3 TMS) - 70eV, Positive	splash10-00bj-9372000000-2a6b263d37306947c327	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Mevalonic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Mevalonic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mevalonic acid Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-0002-2900000000-d1dc97020c103f2a916b	2020-04-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mevalonic acid Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-014i-9000000000-b4dc45e964aee6759d93	2020-04-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mevalonic acid Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-014i-9100000000-98f7e8ee013680f4f610	2020-04-24	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mevalonic acid 10V, Positive-QTOF	splash10-01q9-2900000000-00a30c20b0fe2afce7d8	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mevalonic acid 20V, Positive-QTOF	splash10-03ej-9700000000-c6f9687555150d5ef1a7	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mevalonic acid 40V, Positive-QTOF	splash10-01bi-9100000000-7047d67f0ba1f8aa28ef	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mevalonic acid 10V, Negative-QTOF	splash10-0f72-3900000000-0f765b34011b73405add	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mevalonic acid 20V, Negative-QTOF	splash10-0002-9500000000-dd24fe04989af5af1151	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mevalonic acid 40V, Negative-QTOF	splash10-052s-9100000000-251b958b3e4355c6f2f6	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mevalonic acid 10V, Negative-QTOF	splash10-0fbj-2900000000-fb0c642b03cb9422a9e4	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mevalonic acid 20V, Negative-QTOF	splash10-0a4r-9300000000-1b45622114c4f19f4a9a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mevalonic acid 40V, Negative-QTOF	splash10-0006-9000000000-42ee087c307b5e92b059	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mevalonic acid 10V, Positive-QTOF	splash10-01qa-3900000000-2c25572adb2588760845	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mevalonic acid 20V, Positive-QTOF	splash10-000j-9200000000-b6d834223509e1430e61	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mevalonic acid 40V, Positive-QTOF	splash10-0006-9000000000-e4b7f6f9a91f771bd453	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	2020-04-24	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2020-04-24	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Endoplasmic reticulum
Peroxisome

Biospecimen Locations

Blood
Feces
Saliva
Urine

Tissue Locations

Fibroblasts
Leukocyte
Liver

Pathways

Name	SMPDB/PathBank	KEGG
Steroid Biosynthesis
Smith-Lemli-Opitz Syndrome (SLOS)		Not Available
CHILD Syndrome		Not Available
Desmosterolosis		Not Available
Chondrodysplasia Punctata II, X Linked Dominant (CDPX2)		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.028 +/- 0.006 uM	Adult (>18 years old)	Both	Normal	10947201	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Blood	Detected and Quantified	0.043 +/- 0.013 uM	Adult (>18 years old)	Male	Normal	Geigy Scientific ...	details
Blood	Detected and Quantified	0.026(0.013-0.042) uM	Infant (0-1 year old)	Not Specified	Normal	8386351	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected and Quantified	0.160 (0.0800-0.300) umol/mmol creatinine	Infant (0-1 year old)	Not Specified	Normal	8386351	details
Urine	Detected and Quantified	0.14 (0.06-0.22) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	2702744	details
Urine	Detected and Quantified	0.5 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	12872277	details
Urine	Detected and Quantified	0.0531 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	1653652 12872277	details
Urine	Detected and Quantified	0.178 (0.0515-0.545) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	1653652 12872277	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.012 +/- 0.002 uM	Adult (>18 years old)	Both	Smith-Lemli-Opitz syndrome	10947201	details
Blood	Detected and Quantified	70-540 uM	Infant (0-1 year old)	Both	Mevalonic aciduria	8386351	details
Blood	Detected and Quantified	20-140 uM	Children (1-13 years old)	Both	Mevalonic aciduria	8386351	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Attachment loss	31026179	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Missing teeth	31026179	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Periodontal Probing Depth	31026179	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Tooth Decay	31026179	details
Urine	Detected and Quantified	2100-56000 umol/mmol creatinine	Infant (0-1 year old)	Both	Mevalonic aciduria	8386351	details
Urine	Detected and Quantified	900-14500 umol/mmol creatinine	Children (1-13 years old)	Both	Mevalonic aciduria	8386351	details

Associated Disorders and Diseases

Disease References

Smith-Lemli-Opitz syndrome
Honda M, Tint GS, Honda A, Salen G, Shefer S, Batta AK, Matsuzaki Y, Tanaka N: Regulation of cholesterol biosynthetic pathway in patients with the Smith-Lemli-Opitz syndrome. J Inherit Metab Dis. 2000 Jul;23(5):464-74. [PubMed:10947201 ]
Attachment loss
Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Missing teeth
Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Periodontal Probing Depth
Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Tooth Decay
Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Mevalonic aciduria
Hoffmann GF, Charpentier C, Mayatepek E, Mancini J, Leichsenring M, Gibson KM, Divry P, Hrebicek M, Lehnert W, Sartor K, et al.: Clinical and biochemical phenotype in 11 patients with mevalonic aciduria. Pediatrics. 1993 May;91(5):915-21. [PubMed:8386351 ]

Associated OMIM IDs

270400 (Smith-Lemli-Opitz syndrome)
610377 (Mevalonic aciduria)

External Links

DrugBank ID

DB03518

Phenol Explorer Compound ID

Not Available

FooDB 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

Food Biomarker Ontology

Not Available

VMH ID

MEV_R

MarkerDB ID

MDB00000109

Good Scents ID

Not Available

References

Synthesis Reference

Takahara, Kenji; Nakamura, Yoshio; Ohashi, Takehisa; Watanabe, Kiyoshi. Fermentative production of mevalonic acid. Jpn. Kokai Tokkyo Koho (1985), 4 pp.

Material Safety Data Sheet (MSDS)

Download (PDF)

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 ]
Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
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 ]
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 ]
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 ]
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 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Enzymes

Enzyme Details

1. 3-hydroxy-3-methylglutaryl-coenzyme A reductase

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

Mevalonic acid + Coenzyme A + NADP → 3-Hydroxy-3-methylglutaryl-CoA + NADPH	details
Mevalonic acid + Coenzyme A + NADP → 3-Hydroxy-3-methylglutaryl-CoA + NADPH + Hydrogen Ion	details

Enzyme Details

2. Mevalonate kinase

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 + Mevalonic acid → ADP + Mevalonic acid-5P	details

Showing metabocard for Mevalonic acid (HMDB0000227)

MOL for HMDB0000227 (Mevalonic acid)

3D MOL for HMDB0000227 (Mevalonic acid)

3D SDF for HMDB0000227 (Mevalonic acid)

3D-SDF for HMDB0000227 (Mevalonic acid)

PDB for HMDB0000227 (Mevalonic acid)

3D PDB for HMDB0000227 (Mevalonic acid)

SMILES for HMDB0000227 (Mevalonic acid)

INCHI for HMDB0000227 (Mevalonic acid)

Structure for HMDB0000227 (Mevalonic acid)

3D Structure for HMDB0000227 (Mevalonic acid)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

Reactions

Reactions