Showing metabocard for Gamma-Caprolactone (BMDB0003843)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:06:18 UTC
Update Date2020-04-22 15:12:49 UTC
BMDB IDBMDB0003843
Secondary Accession Numbers
  • BMDB03843
Metabolite Identification
Common NameGamma-Caprolactone
DescriptionGamma-Caprolactone, also known as 4-hydroxy-hexanoate or 4-ethyl-4-butanolide, 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, Gamma-caprolactone is considered to be a fatty ester. Gamma-Caprolactone exists in all eukaryotes, ranging from yeast to plants to humans. Based on a literature review a significant number of articles have been published on Gamma-Caprolactone.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
4-Ethyl-4-butanolideChEBI
4-HexanolideChEBI
4-Hydroxyhexanoic acid lactoneChEBI
5-Ethyltetrahydro-2-furanoneChEBI
6-CaprolactoneChEBI
Dihydro-5-ethyl-2(3H)-furanoneChEBI
gamma-Ethyl-N-butyrolactoneChEBI
gamma-EthylbutyrolactoneChEBI
gamma-HexanolactoneChEBI
4-Hydroxyhexanoate lactoneGenerator
g-Ethyl-N-butyrolactoneGenerator
Γ-ethyl-N-butyrolactoneGenerator
g-EthylbutyrolactoneGenerator
Γ-ethylbutyrolactoneGenerator
g-HexanolactoneGenerator
Γ-hexanolactoneGenerator
g-CaprolactoneGenerator
Γ-caprolactoneGenerator
4-Ethylbutanolide (gamma-hexalactone)HMDB
4-Hydroxy-hexanoateHMDB
4-Hydroxy-hexanoic acidHMDB
4-Hydroxy-hexanoic acid gamma-lactoneHMDB
4-Hydroxy-hexanoic acid lactoneHMDB
4-HydroxyhexanoateHMDB
4-Hydroxyhexanoic acidHMDB
5-Ethyldihydro-2(3H)-furanoneHMDB
5-Ethyldihydrofuran-2(3H)-oneHMDB
gamma-Ethyl-gamma-butyrolactoneHMDB
gamma-HexalactoneHMDB
Hexa-4-olideHMDB
Hexanolide-1,4HMDB
TonkalideHMDB
ToukalideHMDB
Chemical FormulaC6H10O2
Average Molecular Weight114.1424
Monoisotopic Molecular Weight114.068079564
IUPAC Name5-ethyloxolan-2-one
Traditional Namegamma-hexalactone
CAS Registry Number695-06-7
SMILES
CCC1CCC(=O)O1
InChI Identifier
InChI=1S/C6H10O2/c1-2-5-3-4-6(7)8-5/h5H,2-4H2,1H3
InChI KeyJBFHTYHTHYHCDJ-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
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-18 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP0.77ALOGPS
logP1.09ChemAxon
logS-0.71ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity29.25 m³·mol⁻¹ChemAxon
Polarizability12.16 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0570-9000000000-33d7bffec7b90b244b58View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0570-9000000000-44158ddc3fb5887db72fView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-002r-9000000000-043fff98e80d69a0aef2View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0570-9000000000-33d7bffec7b90b244b58View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0570-9000000000-44158ddc3fb5887db72fView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-002r-9000000000-043fff98e80d69a0aef2View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-054o-9000000000-cab1026e3eff252b355aView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-03di-9400000000-8fc4e90e7c0513f35b2bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-052f-9000000000-264ec24375d9874e27c6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0006-9000000000-775242b739802c329ceeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (Unknown) , Positivesplash10-0570-9000000000-33d7bffec7b90b244b58View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-60) , Positivesplash10-0570-9000000000-106225f6b2045cabc0f2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-002r-9000000000-c2681c456564a462e5bcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-014i-9000000000-262d2422966b80201c0dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-23a8252127edf957f937View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-00kf-9000000000-f6b5e0030b789716f778View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-5900000000-6a7b9f7c95a7bbd6d545View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-9300000000-c2191b168940bbcbfcffView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pbc-9000000000-2ca0f454e2ac7dd3126fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-3900000000-493fdb9ba4ad5c9105fcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03xr-9600000000-6600fa8b57b7c1f87013View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-414e486262314b7d9f34View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03k9-9500000000-d90d57e21b78e509a53dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-08fr-9400000000-d4634fc480832e319c94View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9000000000-ef10ab91c5fd551591e2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-9200000000-ed4da47d3cda0847caf6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kf-9000000000-f3b9cd693e882a088770View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9000000000-fb0fd013f40b60315617View in MoNA
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0003843
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB017640
KNApSAcK IDC00053196
Chemspider ID12232
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound12756
PDB IDNot Available
ChEBI ID85235
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available