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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2012-09-11 17:44:49 UTC
Update Date2019-07-23 06:09:16 UTC
HMDB IDHMDB0031681
Secondary Accession Numbers
  • HMDB31681
Metabolite Identification
Common NameDihydro-5-propyl-2(3H)-furanone
DescriptionDihydro-5-propyl-2(3H)-furanone, also known as (+/-)-4-heptanolide or 5-propyl-tetrahydro-furan-2-one, belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. Thus, dihydro-5-propyl-2(3H)-furanone is considered to be a fatty ester lipid molecule. Dihydro-5-propyl-2(3H)-furanone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, dihydro-5-propyl-2(3H)-furanone has been detected, but not quantified in, several different foods, such as alcoholic beverages, fruits, green vegetables, and tea. This could make dihydro-5-propyl-2(3H)-furanone a potential biomarker for the consumption of these foods. Dihydro-5-propyl-2(3H)-furanone is a potentially toxic compound. No indication of carcinogenicity to humans (not listed by IARC).
Structure
Data?1563862156
Synonyms
ValueSource
(+/-)-4-heptanolideHMDB
(+/-)-dihydro-5-propyl-2(3H)-furanoneHMDB
(+/-)-gamma-propyl-gamma-butyrolactoneHMDB
1,4-HeptanolideHMDB
4-Hydroxyheptanoic acid, gamma-lactoneHMDB
4-Propyl-4-hydroxybutanoic acid lactoneHMDB
5-Propyl-tetrahydro-furan-2-oneHMDB
gamma-HeptalactoneHMDB
gamma-HeptanolactoneHMDB
gamma-PropiobutyrolactoneHMDB
gamma-Propyl-gamma-butyrolactoneHMDB
Heptan-4-olideHMDB
Heptanolide-4,1HMDB
Chemical FormulaC7H12O2
Average Molecular Weight128.169
Monoisotopic Molecular Weight128.083729628
IUPAC Name5-propyloxolan-2-one
Traditional Name5-propyloxolan-2-one
CAS Registry Number57129-71-2
SMILES
CCCC1CCC(=O)O1
InChI Identifier
InChI=1S/C7H12O2/c1-2-3-6-4-5-7(8)9-6/h6H,2-5H2,1H3
InChI KeyVLSVVMPLPMNWBH-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassLactones
Sub ClassGamma butyrolactones
Direct ParentGamma butyrolactones
Alternative Parents
Substituents
  • Gamma butyrolactone
  • Tetrahydrofuran
  • Carboxylic acid ester
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility6.81 g/LALOGPS
logP1.42ALOGPS
logP1.53ChemAxon
logS-1.3ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity33.85 m³·mol⁻¹ChemAxon
Polarizability14.17 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000i-9000000000-c224bc120cc60670620fSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000i-9000000000-c224bc120cc60670620fSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-056u-9000000000-d65f08c5431130e748caSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-4900000000-98642a6f9598537ab510Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05r9-9300000000-d38e27aabefbd271fd0aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kf-9000000000-ebcb66a25ad3f79fa256Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-3900000000-705e0da057c614b37de1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0059-9700000000-dc33ef926913eed12375Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-f99153eb643bf57c921dSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Feces
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Campylobacter jejuni infection
details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB017641
KNApSAcK IDNot Available
Chemspider ID7456
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound7742
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .