Structure Database (LMSD)
Common Name
Mevalonolactone
Systematic Name
4-Hydroxy-4-methyltetrahydro-2H-pyran-2-one
Synonyms
3D model of Mevalonolactone
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
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
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
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
Admin
Created at
-
Updated at
27th Apr 2023