Delta-Hexanolactone

Delta-Hexanolactone Description

D-Hexanolactone is the lactone of 5-hydroxy-Hexanoic 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 colid have pronounced effects upon their biological activity and/or distribution. d-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

Synonyms

Chemical Formlia

C₆H₁₀O₂ Average Molecliar Weight

114.1424 Monoisotopic Molecliar Weight

114.068079564 IUPAC Name

6-methyloxan-2-one Traditional Name

hexanolactone CAS Registry Number

823-22-3 SMILES

InChI Identifier

InChI Key

RZTOWFMDBDPERY-UHFFFAOYSA-N Chemical Taxonomy Description

This compound belongs to the class of chemical entities known as delta valerolactones. These are cyclic organic compounds containing an oxan-2- one moiety. Kingdom

Chemical entities Super Class

Organic compounds Class

Organoheterocyclic compounds Sub Class

Lactones Direct Parent

Delta valerolactones Alternative Parents

Substituents

Molecliar Framework

Aliphatic heteromonocyclic compounds External Descriptors

Not Available Ontology Status

Expected but not Quantified Origin

Biofunction

Not Available Application

Not Available Cellliar locations

Physical Properties State

Solid Experimental Properties

Predicted Properties

Spectra Spectra

LC-MS/MS Spectrum – Quattro_QQQ 10V, Positive (Annotated)splash10-014i-9000000000-36d0969790fae080b15eView in MoNA LC-MS/MS

LC-MS/MS Spectrum – Quattro_QQQ 25V, Positive (Annotated)splash10-014i-9000000000-b68dc16317b5e5cd454aView in MoNA LC-MS/MS

LC-MS/MS Spectrum – Quattro_QQQ 40V, Positive (Annotated)splash10-05fr-9100000000-74433d7dfd6ec3f65493View in MoNA LC-MS/MS

LC-MS/MS Spectrum – EI-B (HITACHI M-80B) , Positivesplash10-0006-9000000000-91819f2130833f0f1fb2View in MoNA Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 10V, Positivesplash10-014i-7900000000-e8d560d4b336564e2ccbView in MoNA Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 20V, Positivesplash10-014i-9100000000-65742bbbb910102701f6View in MoNA Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 40V, Positivesplash10-0a6u-9000000000-1fe8eea9b95cd214ad44View in MoNA Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 10V, Negativesplash10-03di-2900000000-17f45c3a4167b21bd28eView in MoNA Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 20V, Negativesplash10-03di-9800000000-fa49d7a801b88ba62245View in MoNA Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 40V, Negativesplash10-0006-9000000000-c440f6358807e3ad3227View in MoNA 1D NMR

1H NMR SpectrumNot Available 2D NMR

[1H,13C] 2D NMR SpectrumNot Available

Biological Properties Cellliar Locations

Biofluid Locations

Not Available Tissue Location

Not Available Pathways

Not Available Normal Concentrations Not Available Abnormal Concentrations

Not Available Associated Disorders and Diseases Disease References

None Associated OMIM IDs

None External Links DrugBank ID

Not Available DrugBank Metabolite ID

Not Available Phenol Explorer Compound ID

Not Available Phenol Explorer Metabolite ID

Not Available FoodDB ID

FDB008077 KNApSAcK ID

Not Available Chemspider ID

12649 KEGG Compound ID

Not Available BioCyc ID

Not Available BiGG ID

Not Available Wikipedia Link

Not Available NuGOwiki Link

HMDB00453 Metagene Link

HMDB00453 METLIN ID

5442 PubChem Compound

13204 PDB ID

Not Available ChEBI ID

589927

Product: Niraparib metabolite M1

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 ]

PMID: 23649661