Structure Database (LMSD)

Common Name
Mevalonolactone
Systematic Name
4-Hydroxy-4-methyltetrahydro-2H-pyran-2-one
Synonyms
LM ID
LMFA07040003
Formula
C6H10O3
Exact Mass
Calculate m/z
130.062995
Sum Composition
FA 6:1;O
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
View ion mobility data

Classification

Category
Main Class
Sub Class
Fatty Acyls [FA]
Fatty esters [FA07]
Lactones [FA0704]
Fatty Acids and Conjugates [FA01]
Branched fatty acids [FA0102]
Hydroxy fatty acids [FA0105]

Biological Context

DL-Mevalonolactone is the δ-lactone form of mevalonic acid, a precursor in the mevalonate pathway.1 It induces depolarization and swelling, decreases NADPH content and aconitase (ACO) activity, and increases malondialdehyde (MDA) production in calcium-loaded rat brain mitochondria.2 DL-Mevalonolactone reverses decreases in glucose uptake induced by simvastatin in L6 myotubes.3 Tissue levels and urinary excretion of DL-mevalonolactone are increased in patients with mevalonic aciduria, a disorder characterized by a deficiency in mevalonic kinase activity.2

This information has been provided by Cayman Chemical

References

1. Domingos, S.R., Pérez, C., and Schnell, M. On the structural intricacies of a metabolic precursor: Direct spectroscopic detection of water-induced conformational reshaping of mevalonolactone. J. Chem. Phys. 147(12), 124310 (2017).
2. Cecatto, C., Amaral, A.U., da Silva, J.C., et al. Mevalonolactone disrupts mitochondrial functions and induces permeability transition pore opening in rat brain mitochondria: Implications for the pathogenesis of mevalonic aciduria. Neurochem. Int. 108, 133-145 (2017).
3. Yaluri, N., Modi, S., and Kokkola, T. Simvastatin induces insulin resistance in L6 skeletal muscle myotubes by suppressing insulin signaling, GLUT4 expression and GSK-3β phosphorylation. Biochem. Biophys. Res. Commun. 480(20), 194-200 (2016).

References

Comments
Pherobase Semiochemicals

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Psammotettix alienus (#1329925)
Insecta (#50557)
[Mevalonolactone: a volatile compound produced by Psammotettix alienus (Dhb)].,
C R Biol, 2002
Pubmed ID: 12481687

String Representations

InChiKey (Click to copy)
JYVXNLLUYHCIIH-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C6H10O3/c1-6(8)2-3-9-5(7)4-6/h8H,2-4H2,1H3
SMILES (Click to copy)
C1C(=O)OCCC1(O)C

Other Databases

CHEBI ID
95115
PubChem CID
10428
Cayman ID
20348

Calculated Physicochemical Properties

Heavy Atoms 9
Rings 1
Aromatic Rings 0
Rotatable Bonds 0
Van der Waals Molecular Volume 123.73
Topological Polar Surface Area 48.60
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 3
logP 0.65
Molar Refractivity 31.82

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Created at
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Updated at
27th Apr 2023