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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2007-04-12 20:29:11 UTC
Update Date2020-02-26 21:26:11 UTC
HMDB IDHMDB0006024
Secondary Accession Numbers
  • HMDB0011647
  • HMDB06024
  • HMDB11647
Metabolite Identification
Common NameMevalonolactone
DescriptionMevalonolactone 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
Data?1582752371
Synonyms
ValueSource
(+/-) tetrahydro-4-hydroxy-4-methyl-2H-pyran-2-oneHMDB
(1)-Tetrahydro-4-hydroxy-4-methyl-2H-pyran-2-oneHMDB
Divalonic acidHMDB
DL-Mevalonic acid lactoneHMDB
DL-MevalonolactoneHMDB
Mevalonic acid lactoneHMDB
Tetrahydro-4-hydroxy-4-methyl-2H-pyran-2-oneHMDB
Mevalonolactone, (+-)-isomerHMDB
Mevalonolactone, (S)-isomerHMDB
Mevalonolactone, 3-(14)C-labeledHMDB
Mevalonolactone, (R)-isomerHMDB
Chemical FormulaC6H10O3
Average Molecular Weight130.1418
Monoisotopic Molecular Weight130.062994186
IUPAC Name(4S)-4-hydroxy-4-methyloxan-2-one
Traditional Name(4S)-4-hydroxy-4-methyloxan-2-one
CAS Registry Number503-48-0
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 KeyJYVXNLLUYHCIIH-LURJTMIESA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as delta valerolactones. These are cyclic organic compounds containing an oxan-2- one moiety.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassLactones
Sub ClassDelta valerolactones
Direct ParentDelta valerolactones
Alternative Parents
Substituents
  • Delta_valerolactone
  • Delta valerolactone
  • Oxane
  • Tertiary alcohol
  • Carboxylic acid ester
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility311 g/LALOGPS
logP-0.14ALOGPS
logP-0.43ChemAxon
logS0.38ALOGPS
pKa (Strongest Acidic)14.71ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity31.02 m³·mol⁻¹ChemAxon
Polarizability12.75 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0adl-9100000000-1c9a26b68d29653e0012Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00bi-7900000000-78e28c02e5bd7ae720d6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03e9-4900000000-68ca20c776905460a6d1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03e9-7900000000-baff68be3b777dcd89b9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uk9-9000000000-20a9cb503d5cc92a04adSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-4900000000-62079a3d434c0d34f51eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01tc-9700000000-9bc2d17474a390c67b5bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002f-9000000000-23e079ef3670bbb35e77Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.0 umol/mmol creatinineChildren (1 - 18 years old)Both
Normal
    • BC Children's Hos...
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023804
KNApSAcK IDNot Available
Chemspider ID4483406
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5325923
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDMVLAC
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General ReferencesNot Available