| Record Information |
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| Version | 5.0 |
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| Status | Detected but not Quantified |
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| Creation Date | 2005-11-16 15:48:42 UTC |
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| Update Date | 2023-02-21 17:14:51 UTC |
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| HMDB ID | HMDB0000453 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | delta-Hexanolactone |
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| Description | delta-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 ). |
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| Structure | InChI=1S/C6H10O2/c1-5-3-2-4-6(7)8-5/h5H,2-4H2,1H3 |
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| Synonyms | | Value | Source |
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| Δ-hexanolactone | Generator | | Epsilon-Caprolactone | HMDB | | (RS)-delta-Hexalactone | HMDB | | 5-Hexanolide | HMDB | | 5-Hydroxy-hexanoate | HMDB | | 5-Hydroxy-hexanoic acid | HMDB | | 5-Hydroxy-hexanoic acid lactone | HMDB | | 5-Hydroxyhexanoate | HMDB | | 5-Hydroxyhexanoic acid | HMDB | | 5-Hydroxyhexanoic acid lactone | HMDB | | 6-Methyl-D-valerolactone | HMDB | | 6-Methylvalerolactone | HMDB | | delta-Caprolactone | HMDB | | delta-Hexalactone | HMDB | | delta-Hexanolide | HMDB | | delta-Methyl-delta-valerolactone | HMDB | | Hexanolactone | HMDB | | Tetrahydro-6-methyl-2H-pyran-2-one | HMDB |
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| Chemical Formula | C6H10O2 |
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| Average Molecular Weight | 114.1424 |
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| Monoisotopic Molecular Weight | 114.068079564 |
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| IUPAC Name | 6-methyloxan-2-one |
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| Traditional Name | hexanolactone |
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| CAS Registry Number | 823-22-3 |
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| SMILES | CC1CCCC(=O)O1 |
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| InChI Identifier | InChI=1S/C6H10O2/c1-5-3-2-4-6(7)8-5/h5H,2-4H2,1H3 |
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| InChI Key | RZTOWFMDBDPERY-UHFFFAOYSA-N |
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| Chemical Taxonomy |
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| Description | Belongs to the class of organic compounds known as delta valerolactones. These are cyclic organic compounds containing an oxan-2- one moiety. |
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| Kingdom | Organic compounds |
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| Super Class | Organoheterocyclic compounds |
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| Class | Lactones |
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| Sub Class | Delta valerolactones |
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| Direct Parent | Delta valerolactones |
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| Alternative Parents | |
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| 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
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| Molecular Framework | Aliphatic heteromonocyclic compounds |
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| External Descriptors | Not Available |
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| Ontology |
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| Physiological effect | |
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| Disposition | |
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| Process | Not Available |
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| Role | Not Available |
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| Physical Properties |
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| State | Solid |
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| Experimental Molecular Properties | |
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| Experimental Chromatographic Properties | Not Available |
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| Predicted Molecular Properties | |
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| Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Retention Times Underivatized| Chromatographic Method | Retention Time | Reference |
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| 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 minutes | 32390414 | | Predicted by Siyang on May 30, 2022 | 13.1665 minutes | 33406817 | | Predicted by Siyang using ReTip algorithm on June 8, 2022 | 3.36 minutes | 32390414 | | AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid | 30.8 seconds | 40023050 | | Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid | 1745.2 seconds | 40023050 | | Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid | 463.3 seconds | 40023050 | | Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid | 170.7 seconds | 40023050 | | Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid | 313.4 seconds | 40023050 | | RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid | 243.9 seconds | 40023050 | | Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid | 475.6 seconds | 40023050 | | BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid | 581.4 seconds | 40023050 | | HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate) | 122.0 seconds | 40023050 | | UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid | 1047.7 seconds | 40023050 | | BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid | 356.8 seconds | 40023050 | | UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid | 1178.5 seconds | 40023050 | | SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid | 343.6 seconds | 40023050 | | RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid | 355.7 seconds | 40023050 | | MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate | 538.0 seconds | 40023050 | | KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA | 463.6 seconds | 40023050 | | Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water | 110.0 seconds | 40023050 |
Predicted Kovats Retention IndicesUnderivatized |
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| Spectra |
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| Biological Properties |
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| Cellular Locations | |
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| Biospecimen Locations | |
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| Tissue Locations | Not Available |
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| Pathways | |
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| Normal Concentrations |
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| Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details |
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| Abnormal Concentrations |
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| Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Colorectal cancer | | details |
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| Associated Disorders and Diseases |
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| Disease References | | Colorectal cancer |
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- 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 ]
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| Associated OMIM IDs | |
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| External Links |
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| DrugBank ID | Not Available |
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| Phenol Explorer Compound ID | Not Available |
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| FooDB ID | FDB008078 |
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| KNApSAcK ID | C00054812 |
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| Chemspider ID | 12649 |
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| KEGG Compound ID | Not Available |
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| BioCyc ID | Not Available |
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| BiGG ID | Not Available |
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| Wikipedia Link | Not Available |
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| METLIN ID | 5442 |
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| PubChem Compound | 13204 |
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| PDB ID | Not Available |
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| ChEBI ID | 589927 |
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| Food Biomarker Ontology | Not Available |
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| VMH ID | Not Available |
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| MarkerDB ID | Not Available |
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| Good Scents ID | rw1026381 |
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| References |
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| Synthesis Reference | Mink, Daniel; Wolberg, Michael; Schuermann, Martin; Hilker, Iris. Chemoenzymic preparation of d-lactones. PCT Int. Appl. (2007), 40pp. |
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| Material Safety Data Sheet (MSDS) | Download (PDF) |
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| General References | - 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 ]
- 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 ]
- 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 ]
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