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Human Metabolome Database Version 3.5

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Showing metabocard for Mevalonolactone (HMDB06024)

Record Information
Version 3.5
Creation Date 2007-04-12 14:29:11 -0600
Update Date 2013-02-08 17:14:28 -0700
HMDB ID HMDB06024
Secondary Accession Numbers
  • HMDB11647
Metabolite Identification
Common Name Mevalonolactone
Description Mevalonolactone is a substance obtained by the dehydration of mevalonic acid and is rapidly converted back into mevalonic acid in water. Mevaolonic acid exists in equilibrium with mevalolactone, which is formed by internal condensation of mevalonic acid's terminal alcohol and carboxylic acid functional groups. Mevalonic acid is a key intermediate in the biosynthesis of terpenes and steroids. Mevalonolactone is known ot inhibit HMG-CoA reductase activity.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. (+/-) Tetrahydro-4-hydroxy-4-methyl-2H-pyran-2-one
  2. (1)-Tetrahydro-4-hydroxy-4-methyl-2H-pyran-2-one
  3. Divalonic acid
  4. DL-mevalonic acid lactone
  5. DL-Mevalonolactone
  6. Mevalonic acid lactone
  7. Tetrahydro-4-hydroxy-4-methyl-2H-pyran-2-one
Chemical Formula C6H10O3
Average Molecular Weight 130.1418
Monoisotopic Molecular Weight 130.062994186
IUPAC Name (4S)-4-hydroxy-4-methyloxan-2-one
Traditional IUPAC Name (4S)-4-hydroxy-4-methyloxan-2-one
CAS Registry Number 503-48-0
SMILES C[C@]1(O)CCOC(=O)C1
InChI Identifier InChI=1S/C6H10O3/c1-6(8)2-3-9-5(7)4-6/h8H,2-4H2,1H3/t6-/m0/s1
InChI Key JYVXNLLUYHCIIH-LURJTMIESA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aliphatic Heteromonocyclic Compounds
Class Lactones
Sub Class N/A
Other Descriptors
  • Carboxylic Acid Esters
  • Oxanes
  • Tertiary Alcohols
Substituents
  • N/A
Direct Parent Lactones
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations Not Available
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 311 g/L ALOGPS
LogP -0.14 ALOGPS
LogP -0.43 ChemAxon
LogS 0.38 ALOGPS
pKa (strongest acidic) 14.71 ChemAxon
pKa (strongest basic) -2.9 ChemAxon
Hydrogen Acceptor Count 2 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 46.53 A2 ChemAxon
Rotatable Bond Count 0 ChemAxon
Refractivity 31.02 ChemAxon
Polarizability 12.75 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
1H NMR Spectrum
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations Not Available
Biofluid Locations Not Available
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB023804
KNApSAcK ID Not Available
Chemspider ID 4483406 Link_out
KEGG Compound ID Not Available
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB06024 Link_out
Metagene Link HMDB06024 Link_out
METLIN ID Not Available
PubChem Compound 5325923 Link_out
PDB ID Not Available
ChEBI ID Not Available
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Download (PDF)
General References Not Available