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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:14:51 UTC
HMDB IDHMDB0000453
Secondary Accession Numbers
  • HMDB00453
Metabolite Identification
Common Namedelta-Hexanolactone
Descriptiondelta-Hexanolactone is the lactone of 5-hydroxyhexanoic acid. Lactones are internal esters that exist in equilibrium between their closed (lactone) and open (hydroxy acid) forms in an aqueous environment. The lactone/hydroxy acid ratio at equilibrium is pH-dependent, with the closed form being favored at lower pH values, and can be greatly influenced by structural features of the lactone such as the ring size, substituents on the ring and the presence of double bonds within the ring. Many drugs and endogenous compounds are lactones or hydroxy acids and an enzyme capable of catalyzing the interchange between the open and closed forms in vivo could have pronounced effects upon their biological activity and/or distribution. delta-Hexanolactone is the substrate of paraoxonases (PON) in humans. Human PON1 hydrolyzes over 30 different lactones (cyclic esters) and catalyzes the reverse reaction (lactonization) of a broad range of hydroxy acids. Hydroxy acid lactonization or lactone hydrolysis is catalyzed until equilibrium between the open and closed forms is reached (PMID: 15772423 , 12963475 , 12963475 ).
Structure
Data?1676999691
Synonyms
ValueSource
Δ-hexanolactoneGenerator
Epsilon-CaprolactoneHMDB
(RS)-delta-HexalactoneHMDB
5-HexanolideHMDB
5-Hydroxy-hexanoateHMDB
5-Hydroxy-hexanoic acidHMDB
5-Hydroxy-hexanoic acid lactoneHMDB
5-HydroxyhexanoateHMDB
5-Hydroxyhexanoic acidHMDB
5-Hydroxyhexanoic acid lactoneHMDB
6-Methyl-D-valerolactoneHMDB
6-MethylvalerolactoneHMDB
delta-CaprolactoneHMDB
delta-HexalactoneHMDB
delta-HexanolideHMDB
delta-Methyl-delta-valerolactoneHMDB
HexanolactoneHMDB
Tetrahydro-6-methyl-2H-pyran-2-oneHMDB
Chemical FormulaC6H10O2
Average Molecular Weight114.1424
Monoisotopic Molecular Weight114.068079564
IUPAC Name6-methyloxan-2-one
Traditional Namehexanolactone
CAS Registry Number823-22-3
SMILES
CC1CCCC(=O)O1
InChI Identifier
InChI=1S/C6H10O2/c1-5-3-2-4-6(7)8-5/h5H,2-4H2,1H3
InChI KeyRZTOWFMDBDPERY-UHFFFAOYSA-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
  • 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 DescriptorsNot Available
Ontology
Physiological effect
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point31.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Boiling Point110.00 to 112.00 °C. @ 15.00 mm HgThe Good Scents Company Information System
Water Solubility32190 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP0.431 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility24.1 g/LALOGPS
logP0.93ALOGPS
logP1.01ChemAxon
logS-0.68ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity29.33 m³·mol⁻¹ChemAxon
Polarizability12.12 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]+123.5131661259
DarkChem[M-H]-117.61231661259
AllCCS[M+H]+123.4532859911
AllCCS[M-H]-124.01532859911
DeepCCS[M+H]+131.27430932474
DeepCCS[M-H]-129.19330932474
DeepCCS[M-2H]-165.230932474
DeepCCS[M+Na]+139.60830932474
AllCCS[M+H]+123.532859911
AllCCS[M+H-H2O]+118.532859911
AllCCS[M+NH4]+128.132859911
AllCCS[M+Na]+129.432859911
AllCCS[M-H]-124.032859911
AllCCS[M+Na-2H]-126.632859911
AllCCS[M+HCOO]-129.432859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.2.98 minutes32390414
Predicted by Siyang on May 30, 202213.1665 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20223.36 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid30.8 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid1745.2 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid463.3 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid170.7 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid313.4 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid243.9 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid475.6 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid581.4 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)122.0 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid1047.7 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid356.8 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid1178.5 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid343.6 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid355.7 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate538.0 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA463.6 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water110.0 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
delta-HexanolactoneCC1CCCC(=O)O11754.9Standard polar33892256
delta-HexanolactoneCC1CCCC(=O)O11008.9Standard non polar33892256
delta-HexanolactoneCC1CCCC(=O)O11056.3Semi standard non polar33892256
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB008078
KNApSAcK IDC00054812
Chemspider ID12649
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5442
PubChem Compound13204
PDB IDNot Available
ChEBI ID589927
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1026381
References
Synthesis ReferenceMink, Daniel; Wolberg, Michael; Schuermann, Martin; Hilker, Iris. Chemoenzymic preparation of d-lactones. PCT Int. Appl. (2007), 40pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Draganov DI, Teiber JF, Speelman A, Osawa Y, Sunahara R, La Du BN: Human paraoxonases (PON1, PON2, and PON3) are lactonases with overlapping and distinct substrate specificities. J Lipid Res. 2005 Jun;46(6):1239-47. Epub 2005 Mar 16. [PubMed:15772423 ]
  2. Moser AB, Jones DS, Raymond GV, Moser HW: Plasma and red blood cell fatty acids in peroxisomal disorders. Neurochem Res. 1999 Feb;24(2):187-97. [PubMed:9972864 ]
  3. Teiber JF, Draganov DI, La Du BN: Lactonase and lactonizing activities of human serum paraoxonase (PON1) and rabbit serum PON3. Biochem Pharmacol. 2003 Sep 15;66(6):887-96. [PubMed:12963475 ]