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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-05-17 01:23:34 UTC
Update Date2020-07-06 16:02:33 UTC
HMDB IDHMDB0060476
Secondary Accession Numbers
  • HMDB60476
Metabolite Identification
Common Nameepsilon-Caprolactone
Descriptionε-Caprolactone, also known simply as caprolactone, is a compound belonging to the family of compounds known as lactones. Lactones are cyclic esters of hydroxyl carboxylic acids, wherein the functional group has become part of a ring structure with carbon atoms. Caprolactone consists of a seven membered ring derived from the cyclization of caproic acid. As a monomer it used in the production of highly specialized plastics and polymers. Caprolactone is produced by the Baeyer-Villiger oxidation of cyclohexanone with peracetic acid, and was used previously (until economically inviable) as a precursor in the production of caprolactam. Several other caprolactone isomers are known. These isomers include α-, β-, γ-, and δ-caprolactones. All are chiral. (R)-γ-caprolactone is a component of floral scents and of the aromas of some fruits and vegetables (Journal of Agricultural and Food Chemistry. 37: 413–418), while δ-caprolactone is found in heated milk fat (Journal of Dairy Science. 48 (5): 615–616).
Structure
Data?1563866065
Synonyms
ValueSource
1,6-HexanolideChEBI
1-Oxa-2-oxocycloheptaneChEBI
2-OxacycloheptanoneChEBI
2-OxepanoneChEBI
2-Oxohexamethylene oxideChEBI
6-HexanolactoneChEBI
6-HexanolideChEBI
6-Hydroxyhexanoic acid lactoneChEBI
6-Hydroxyhexanoic acid, epsilon-lactoneChEBI
CaprolactoneChEBI
epsilon-Caprolactone monomerChEBI
Hexan-6-olideChEBI
Hexanoic acid, epsilon-lactoneChEBI
Hexano-6-lactoneKegg
6-Hydroxyhexanoate lactoneGenerator
6-Hydroxyhexanoate, epsilon-lactoneGenerator
Hexanoate, epsilon-lactoneGenerator
epsilon-Captolactamium hydrogen sulfateHMDB
epsilon-CaprolactoneChEBI
Chemical FormulaC6H10O2
Average Molecular Weight114.1424
Monoisotopic Molecular Weight114.068079564
IUPAC Nameoxepan-2-one
Traditional Namecaprolactone
CAS Registry NumberNot Available
SMILES
O=C1CCCCCO1
InChI Identifier
InChI=1S/C6H10O2/c7-6-4-2-1-3-5-8-6/h1-5H2
InChI KeyPAPBSGBWRJIAAV-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as lactones. These are cyclic esters of hydroxy carboxylic acids, containing a 1-oxacycloalkan-2-one structure, or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassLactones
Sub ClassNot Available
Direct ParentLactones
Alternative Parents
Substituents
  • Caprolactone
  • Oxepane
  • Lactone
  • 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

Source

Route of exposure

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 Solubility23.2 g/LALOGPS
logP10(0.51) g/LALOGPS
logP10(1.04) g/LChemAxon
logS10(-0.69) g/LALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity29.51 m³·mol⁻¹ChemAxon
Polarizability11.99 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]+123.00731661259
DarkChem[M-H]-117.65731661259
DeepCCS[M+H]+130.9630932474
DeepCCS[M-H]-128.84130932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
epsilon-CaprolactoneO=C1CCCCCO11899.1Standard polar33892256
epsilon-CaprolactoneO=C1CCCCCO11035.9Standard non polar33892256
epsilon-CaprolactoneO=C1CCCCCO11041.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - epsilon-Caprolactone EI-B (Non-derivatized)splash10-052f-9000000000-d988c3d2aef36f68a34c2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - epsilon-Caprolactone EI-B (Non-derivatized)splash10-052f-9000000000-d988c3d2aef36f68a34c2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - epsilon-Caprolactone GC-MS (Non-derivatized) - 70eV, Positivesplash10-004l-9000000000-8217d06e4a5254272c262017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - epsilon-Caprolactone 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 - epsilon-Caprolactone 10V, Positive-QTOFsplash10-014i-3900000000-d94e398e2ee123530b4f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - epsilon-Caprolactone 20V, Positive-QTOFsplash10-014i-9400000000-fc41d0ade3b55f7291c02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - epsilon-Caprolactone 40V, Positive-QTOFsplash10-0a4l-9000000000-862a975676e9bf4924df2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - epsilon-Caprolactone 10V, Negative-QTOFsplash10-03di-1900000000-756be03620da7cfbd76f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - epsilon-Caprolactone 20V, Negative-QTOFsplash10-03di-8900000000-13e99685e36286d5f0c72016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - epsilon-Caprolactone 40V, Negative-QTOFsplash10-052f-9000000000-5dc62aecedc9db16ddd12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - epsilon-Caprolactone 10V, Positive-QTOFsplash10-014i-9400000000-f060672f001b0ed52de92021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - epsilon-Caprolactone 20V, Positive-QTOFsplash10-00xu-9000000000-914e64a3efc4beff8c592021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - epsilon-Caprolactone 40V, Positive-QTOFsplash10-0a4i-9000000000-59e5dead8150b8ddd28b2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - epsilon-Caprolactone 10V, Negative-QTOFsplash10-03di-0900000000-26d0fd1f45832bba15082021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - epsilon-Caprolactone 20V, Negative-QTOFsplash10-03di-7900000000-0a2a806fd9a2f25f91892021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - epsilon-Caprolactone 40V, Negative-QTOFsplash10-0006-9100000000-752185e44397ff541ef72021-10-12Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC01880
BioCyc IDCPD-101
BiGG IDNot Available
Wikipedia LinkCaprolactone
METLIN IDNot Available
PubChem Compound10401
PDB IDNot Available
ChEBI ID17915
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. Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]

Enzymes

General function:
Involved in calcium ion binding
Specific function:
Gluconolactonase with low activity towards other sugar lactones, including gulonolactone and galactonolactone. Can also hydrolyze diisopropyl phosphorofluoridate and phenylacetate (in vitro). Calcium-binding protein. Modulates Ca(2+) signaling, and Ca(2+)-dependent cellular processes and enzyme activities (By similarity).
Gene Name:
RGN
Uniprot ID:
Q15493
Molecular weight:
33252.53
Reactions
epsilon-Caprolactone + Water → 6-Hydroxyhexanoic aciddetails