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Mevalonic acid information


Mevalonic acid
Names
Preferred IUPAC name
(3R)-3,5-Dihydroxy-3-methylpentanoic acid
Identifiers
CAS Number
  • 150-97-0 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:17710 ☒N
ChemSpider
  • 388367 ☒N
KEGG
  • C00418 ☒N
PubChem CID
  • 439230
UNII
  • S5UOB36OCZ checkY
CompTox Dashboard (EPA)
  • DTXSID5040546 Edit this at Wikidata
InChI
  • 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 148.158 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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 like statins (which lower levels of cholesterol) stop the production of mevalonate by inhibiting HMG-CoA reductase.[1]

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

and 27 Related for: Mevalonic acid information

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Mevalonic acid

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Mevalonic acid (MVA) is a key organic compound in biochemistry; the name is a contraction of dihydroxymethylvalerolactone. The carboxylate anion of mevalonic...

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Mevalonate pathway

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diseases affect the mevalonate pathway: Mevalonate Kinase Deficiency Mevalonic Aciduria Hyperimmunoglobulinemia D Syndrome (HIDS). Plants, most bacteria...

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Lysergic acid

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tryptophan with dimethylallyl diphosphate (isoprene derived from 3R-mevalonic acid) giving 4-dimethylallyl-L-tryptophan which is N-methylated with...

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Abscisic acid

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the structurally related sesquiterpenes, which are formed from the mevalonic acid-derived precursor farnesyl diphosphate (FDP), the C15 backbone of ABA...

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Mevalonate kinase deficiency

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reduced or deficient activity of this enzyme. Because of this deficiency, mevalonic acid can build up in the body, with high levels found in the urine. The severity...

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Dimethylallyl pyrophosphate

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DMAPP and IPP. In the mevalonate pathway DMAPP is synthesised from mevalonic acid. In contrast, DMAPP is synthesised from HMBPP in the MEP pathway. At...

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Ergine

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form 4-L-dimethylallyltryptophan (4-L-DMAT). The DMAPP is derived from mevalonic acid. A three strep mechanism is proposed to form 4-L-DMAT: the formation...

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Simvastatin

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researching the biosynthesis of cholesterol in the early 1950s. In 1956, mevalonic acid was isolated from a yeast extract by Karl Folkers, Carl Hoffman, and...

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Cell synchronization

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A reductase, an enzyme vital in the production of mevalonic acid. Mevalonic acid is a key intermediate in the mevalonate pathway responsible...

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Juvabione

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form 3-hydroxy-3-methylglutaryl-CoA (HMG-CoA) which then is reduced to mevalonic acid (MVA). A series of ATP-dependent transformations lead to a key isoprene...

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Plant secondary metabolism

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in plastids. Carotenoids formed in fungi are presumably formed from mevalonic acid precursors. Carotenoids are formed by a head-to-head condensation of...

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Monoterpene

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pyrophosphate, which is formed from acetyl-CoA via the intermediacy of mevalonic acid in the HMG-CoA reductase pathway. An alternative, unrelated biosynthesis...

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Meglutol

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free in Crotalaria dura and C. globifera and is bound in dicrotaline (pyrrolizidine alkaloid). Crotalaria List of Crotalaria species Mevalonic acid v t e...

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Bactoprenol

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(E,E)-farnesyl diphosphate. Bactoprenol is a lipid synthesized from mevalonic acid and is the most abundant lipid found in certain species of lactobacilli...

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Lycopene

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cyanobacteria is similar, as are the enzymes involved. Synthesis begins with mevalonic acid, which is converted into dimethylallyl pyrophosphate. This is then condensed...

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MVA

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method of abortion that consists of removing the embryo by suction Mevalonic acid, an important compound in molecular biology Mimotope Variation Analysis...

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Viridin

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The complete biosynthesis of viridin is not known. Through [2-14C]mevalonic acid labeling studies, it has been shown that viridin is biosynthesized from...

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Phytoecdysteroid

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phytoecdysteroids. Plants, but not animals, synthesize phytoecdysteroids from mevalonic acid in the mevalonate pathway of the plant cell using acetyl-CoA as a precursor...

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Mevalonate kinase

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enzyme in the Mevalonate pathway, it catalyzes the phosphorylation of Mevalonic acid to produce Mevalonate-5-phosphate. A reduction in mevalonate kinase...

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Konrad Emil Bloch

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showed that acetyl Coenzyme A is turned into mevalonic acid. Both Bloch and Lynen then showed that mevalonic acid is converted into chemically active isoprene...

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Carotenoid

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known to use two different pathways for IPP production: the cytosolic mevalonic acid pathway (MVA) and the plastidic methylerythritol 4-phosphate (MEP)....

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Plant communication

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biosynthesis of terpenoids occurs via the methylerythritol phosphate (MEP) and mevalonic acid(MVA) pathways both of which include isopentenyl diphosphate (IPP) and...

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C6H12O4

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4,5-Cyclohexanetetrol 2,3-Dihydroxy-3-methylpentanoic acid Kethoxal Mevalonic acid Pantoic acid This set index page lists chemical structure articles...

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Bombus lucorum

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that contain only fatty acid derivatives and PP + MAP type secretions that contain fatty acid derivatives and mevalonic acid derivatives in the form of...

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Lovastatin

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of the microsomal enzyme that catalyzes the conversion of HMG CoA to mevalonic acid, and that has been considered to be a prime target for pharmacologic...

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Alkaloid

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group also includes some related compounds with neutral and even weakly acidic properties. Some synthetic compounds of similar structure may also be termed...

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Lipid

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diphosphate and dimethylallyl diphosphate, which are produced mainly via the mevalonic acid (MVA) pathway. The simple isoprenoids (linear alcohols, diphosphates...

Word Count : 7365

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