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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2007-04-12 20:29:11 UTC
Update Date2022-09-22 18:34:18 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, MeSH
tetrahydro-4-Hydroxy-4-methyl-2H-pyran-2-oneHMDB
Mevalonolactone, (+-)-isomerMeSH, HMDB
Mevalonolactone, (S)-isomerMeSH, HMDB
Mevalonolactone, 3-(14)C-labeledMeSH, HMDB
Mevalonolactone, (R)-isomerMeSH, HMDB
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
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+128.68231661259
DarkChem[M-H]-121.38331661259
DeepCCS[M+H]+127.74830932474
DeepCCS[M-H]-124.51130932474
DeepCCS[M-2H]-161.49130932474
DeepCCS[M+Na]+136.77330932474
AllCCS[M+H]+125.932859911
AllCCS[M+H-H2O]+121.132859911
AllCCS[M+NH4]+130.332859911
AllCCS[M+Na]+131.632859911
AllCCS[M-H]-124.932859911
AllCCS[M+Na-2H]-127.132859911
AllCCS[M+HCOO]-129.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
MevalonolactoneC[C@]1(O)CCOC(=O)C12185.2Standard polar33892256
MevalonolactoneC[C@]1(O)CCOC(=O)C11149.0Standard non polar33892256
MevalonolactoneC[C@]1(O)CCOC(=O)C11283.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Mevalonolactone,1TMS,isomer #1C[C@]1(O[Si](C)(C)C)CCOC(=O)C11430.3Semi standard non polar33892256
Mevalonolactone,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@@]1(C)CCOC(=O)C11614.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Mevalonolactone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0adl-9100000000-1c9a26b68d29653e00122017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Mevalonolactone GC-MS (1 TMS) - 70eV, Positivesplash10-00bi-7900000000-78e28c02e5bd7ae720d62017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Mevalonolactone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Mevalonolactone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Mevalonolactone 40V, Positive-QTOFsplash10-0006-9000000000-022966682f3b96dc0d5f2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Mevalonolactone 10V, Positive-QTOFsplash10-01b9-9200000000-cb61206c3e36cc98b4432021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Mevalonolactone 10V, Positive-QTOFsplash10-014i-9100000000-a396670270ef2f6397522021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Mevalonolactone 20V, Positive-QTOFsplash10-0006-9000000000-6ab12a73af94be72fea02021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Mevalonolactone 20V, Positive-QTOFsplash10-0006-9000000000-ab2794aee94954af40d02021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Mevalonolactone 40V, Positive-QTOFsplash10-0006-9000000000-0029525e10eaeb8d4df42021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mevalonolactone 10V, Positive-QTOFsplash10-03e9-4900000000-68ca20c776905460a6d12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mevalonolactone 20V, Positive-QTOFsplash10-03e9-7900000000-baff68be3b777dcd89b92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mevalonolactone 40V, Positive-QTOFsplash10-0uk9-9000000000-20a9cb503d5cc92a04ad2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mevalonolactone 10V, Negative-QTOFsplash10-004i-4900000000-62079a3d434c0d34f51e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mevalonolactone 20V, Negative-QTOFsplash10-01tc-9700000000-9bc2d17474a390c67b5b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mevalonolactone 40V, Negative-QTOFsplash10-002f-9000000000-23e079ef3670bbb35e772016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mevalonolactone 10V, Positive-QTOFsplash10-03di-2900000000-350c680f97580a3bcd722021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mevalonolactone 20V, Positive-QTOFsplash10-0jbm-9200000000-53d741ed76e6bdf9342f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mevalonolactone 40V, Positive-QTOFsplash10-0006-9000000000-1fa9b1e3048c34d9c1fc2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mevalonolactone 10V, Negative-QTOFsplash10-004i-5900000000-34b2add939c12cfa98dd2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mevalonolactone 20V, Negative-QTOFsplash10-01ox-9400000000-8b6184467b21550de12d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mevalonolactone 40V, Negative-QTOFsplash10-052f-9000000000-f91715bf1f16241894b82021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 500 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>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
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
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
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General ReferencesNot Available