General Information of MET (ID: META00213)
Name Mevalonic acid
Synonyms   Click to Show/Hide Synonyms of This Metabolite
(3R)-3,5-Dihydroxy-3-methylpentanoic acid; (3R)-Mevalonic acid; (R)-(-)-Mevalonic acid; (R)-3,5-Dihydroxy-3-methylpentanoic acid; (R)-3,5-Dihydroxy-3-methylvalerate; (R)-3,5-Dihydroxy-3-methylvaleric acid; (R)-Mevalonate; (R)-Mevalonic acid; 2,4-Dideoxy-3-C-methylpentonic acid; 3,5-Dihydroxy-3-methylpentanoic acid; 3,5-Dihydroxy-3-methylvalerate; 3,5-Dihydroxy-3-methylvaleric acid; Acid, mevalonic; Hiochic acid; MVA; Mevalonate; Mevalonic acid; R-Mevalonic acid
Source Endogenous;Yeast Metabolite;Food
Structure Type   Fatty acids and conjugates  (Click to Show/Hide the Complete Structure Type Hierarchy)
Lipids and lipid-like molecules
Fatty Acyls
Fatty acids and conjugates
PubChem CID
439230
HMDB ID
HMDB0000227
Formula
C6H12O4
Structure
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3D MOL 2D MOL
  Click to Show/Hide the Molecular/Functional Data (External Links/Property/Function) of This Metabolite
KEGG ID
C00418
DrugBank ID
DB03518
ChEBI ID
17710
FooDB ID
FDB005126
ChemSpider ID
388367
Physicochemical Properties Molecular Weight 148.16 Topological Polar Surface Area 77.8
XlogP -1 Complexity 123
Heavy Atom Count 10 Rotatable Bond Count 4
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 4
Function
Mevalonic acid (CAS: 150-97-0), 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 very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 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. Mevalonic acid is a key organic compound in biochemistry. 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. Plasma concentrations and urinary excretion of MVA are decreased by HMG-CoA reductase inhibitor drugs such as pravastatin, simvastatin, and atorvastatin.
Regulatory Network
Full List of Protein(s) Regulating This Metabolite
      Transferases (EC 2)
            Squalene synthase (FDFT1) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [1]
                      Introduced Variation Mutation of FDFT1
                      Induced Change Mevalonic acid concentration: increase
                      Summary Introduced Variation         Induced Change 
                      Disease Status Lipid metabolism disorders [ICD-11: 5C52]
                      Details It is reported that mutation (patients with variants in FDFT1) of FDFT1 leads to the increase of mevalonic acid levels compared with control group.
References
1 Squalene Synthase Deficiency.

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