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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 17:44:49 UTC
Update Date2023-02-21 17:21:10 UTC
HMDB IDHMDB0031681
Secondary Accession Numbers
  • HMDB31681
Metabolite Identification
Common NameDihydro-5-propyl-2(3H)-furanone
DescriptionDihydro-5-propyl-2(3H)-furanone 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. Dihydro-5-propyl-2(3H)-furanone is a sweet, caramel, and coconut tasting compound. Dihydro-5-propyl-2(3H)-furanone has been detected, but not quantified in, asparagus (Asparagus officinalis) and peaches (Prunus persica). This could make dihydro-5-propyl-2(3H)-furanone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Dihydro-5-propyl-2(3H)-furanone.
Structure
Data?1677000070
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
4-Propyl-g-butyrolactoneGenerator
4-Propyl-γ-butyrolactoneGenerator
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
Physiological effect
Disposition
ProcessNot Available
Role
Physical Properties
StateNot Available
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 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+127.0731661259
DarkChem[M-H]-121.29631661259
DeepCCS[M+H]+132.99430932474
DeepCCS[M-H]-130.64130932474
DeepCCS[M-2H]-166.94930932474
DeepCCS[M+Na]+141.48230932474
AllCCS[M+H]+128.532859911
AllCCS[M+H-H2O]+123.832859911
AllCCS[M+NH4]+132.832859911
AllCCS[M+Na]+134.132859911
AllCCS[M-H]-129.832859911
AllCCS[M+Na-2H]-131.932859911
AllCCS[M+HCOO]-134.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Dihydro-5-propyl-2(3H)-furanoneCCCC1CCC(=O)O11802.2Standard polar33892256
Dihydro-5-propyl-2(3H)-furanoneCCCC1CCC(=O)O11085.7Standard non polar33892256
Dihydro-5-propyl-2(3H)-furanoneCCCC1CCC(=O)O11159.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Dihydro-5-propyl-2(3H)-furanone EI-B (Non-derivatized)splash10-000i-9000000000-c224bc120cc60670620f2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Dihydro-5-propyl-2(3H)-furanone EI-B (Non-derivatized)splash10-000i-9000000000-c224bc120cc60670620f2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dihydro-5-propyl-2(3H)-furanone GC-MS (Non-derivatized) - 70eV, Positivesplash10-056u-9000000000-d65f08c5431130e748ca2016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dihydro-5-propyl-2(3H)-furanone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dihydro-5-propyl-2(3H)-furanone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydro-5-propyl-2(3H)-furanone 10V, Positive-QTOFsplash10-004i-4900000000-98642a6f9598537ab5102015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydro-5-propyl-2(3H)-furanone 20V, Positive-QTOFsplash10-05r9-9300000000-d38e27aabefbd271fd0a2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydro-5-propyl-2(3H)-furanone 40V, Positive-QTOFsplash10-00kf-9000000000-ebcb66a25ad3f79fa2562015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydro-5-propyl-2(3H)-furanone 10V, Negative-QTOFsplash10-004i-3900000000-705e0da057c614b37de12015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydro-5-propyl-2(3H)-furanone 20V, Negative-QTOFsplash10-0059-9700000000-dc33ef926913eed123752015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydro-5-propyl-2(3H)-furanone 40V, Negative-QTOFsplash10-0006-9000000000-f99153eb643bf57c921d2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydro-5-propyl-2(3H)-furanone 10V, Positive-QTOFsplash10-05o3-9100000000-c0ea09b5a63622fe42f62021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydro-5-propyl-2(3H)-furanone 20V, Positive-QTOFsplash10-0a4i-9000000000-548b7b2060383993efa42021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydro-5-propyl-2(3H)-furanone 40V, Positive-QTOFsplash10-0a4l-9000000000-bf344b6b6e2f603abaab2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydro-5-propyl-2(3H)-furanone 10V, Negative-QTOFsplash10-004i-0900000000-3a7b7e53b32e365081f92021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydro-5-propyl-2(3H)-furanone 20V, Negative-QTOFsplash10-004i-9700000000-30794976276fa018bbe42021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydro-5-propyl-2(3H)-furanone 40V, Negative-QTOFsplash10-052f-9000000000-3e450e442b08ba75cbd52021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX labView Spectrum
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 IDFDB008341
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 IDNot Available
Good Scents IDNot Available
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.. .