Record Information
Version1.0
Creation date2011-09-21 00:34:57 UTC
Update date2015-10-09 22:33:34 UTC
Primary IDFDB023804
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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. [HMDB]
CAS Number503-48-0
Structure
Thumb
Synonyms
SynonymSource
(+/-) 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, (+-)-isomerMeSH
Mevalonolactone, (S)-isomerMeSH
Mevalonolactone, 3-(14)C-labeledMeSH
Mevalonolactone, (R)-isomerMeSH
(+/-) Tetrahydro-4-hydroxy-4-methyl-2H-pyran-2-onehmdb
(1)-Tetrahydro-4-hydroxy-4-methyl-2H-pyran-2-onehmdb
DL-mevalonic acid lactonehmdb
Tetrahydro-4-hydroxy-4-methyl-2H-pyran-2-onehmdb
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC6H10O3
IUPAC name(4S)-4-hydroxy-4-methyloxan-2-one
InChI IdentifierInChI=1S/C6H10O3/c1-6(8)2-3-9-5(7)4-6/h8H,2-4H2,1H3/t6-/m0/s1
InChI KeyJYVXNLLUYHCIIH-LURJTMIESA-N
Isomeric SMILESC[C@]1(O)CCOC(=O)C1
Average Molecular Weight130.1418
Monoisotopic Molecular Weight130.062994186
Classification
DescriptionThis compound 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
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0adl-9100000000-1c9a26b68d29653e0012View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00bi-7900000000-78e28c02e5bd7ae720d6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03e9-4900000000-68ca20c776905460a6d1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03e9-7900000000-baff68be3b777dcd89b9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uk9-9000000000-20a9cb503d5cc92a04adView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-4900000000-62079a3d434c0d34f51eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01tc-9700000000-9bc2d17474a390c67b5bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002f-9000000000-23e079ef3670bbb35e77View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
ChemSpider ID4483406
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID5325923
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB06024
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference