Structure Database (LMSD)

Common Name
Mevalonolactone
Systematic Name
4-Hydroxy-4-methyltetrahydro-2H-pyran-2-one
Synonyms
LM ID
LMFA07040003
Formula
Exact Mass
Calculate m/z
130.062995
Sum Composition
Status
Curated


Classification

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).

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
PubChem CID
Cayman ID

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