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 Kovats Retention IndicesUnderivatized |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental GC-MS | GC-MS Spectrum - delta-Hexanolactone EI-B (Non-derivatized) | splash10-0006-9000000000-ec974c9bdaa10e2a4003 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - delta-Hexanolactone EI-B (Non-derivatized) | splash10-0006-9000000000-ec974c9bdaa10e2a4003 | 2018-05-18 | HMDB team, MONA, MassBank | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - delta-Hexanolactone GC-MS (Non-derivatized) - 70eV, Positive | splash10-0096-9000000000-110e65c1001acb050610 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - delta-Hexanolactone GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental LC-MS/MS | LC-MS/MS Spectrum - delta-Hexanolactone Quattro_QQQ 10V, Positive-QTOF (Annotated) | splash10-014i-9000000000-36d0969790fae080b15e | 2012-07-24 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - delta-Hexanolactone Quattro_QQQ 25V, Positive-QTOF (Annotated) | splash10-014i-9000000000-b68dc16317b5e5cd454a | 2012-07-24 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - delta-Hexanolactone Quattro_QQQ 40V, Positive-QTOF (Annotated) | splash10-05fr-9100000000-74433d7dfd6ec3f65493 | 2012-07-24 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - delta-Hexanolactone EI-B (HITACHI M-80B) , Positive-QTOF | splash10-0006-9000000000-91819f2130833f0f1fb2 | 2012-08-31 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - delta-Hexanolactone 10V, Positive-QTOF | splash10-014i-7900000000-e8d560d4b336564e2ccb | 2015-04-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - delta-Hexanolactone 20V, Positive-QTOF | splash10-014i-9100000000-65742bbbb910102701f6 | 2015-04-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - delta-Hexanolactone 40V, Positive-QTOF | splash10-0a6u-9000000000-1fe8eea9b95cd214ad44 | 2015-04-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - delta-Hexanolactone 10V, Negative-QTOF | splash10-03di-2900000000-17f45c3a4167b21bd28e | 2015-04-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - delta-Hexanolactone 20V, Negative-QTOF | splash10-03di-9800000000-fa49d7a801b88ba62245 | 2015-04-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - delta-Hexanolactone 40V, Negative-QTOF | splash10-0006-9000000000-c440f6358807e3ad3227 | 2015-04-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - delta-Hexanolactone 10V, Positive-QTOF | splash10-014l-9100000000-385cf07fe667b5dcf42a | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - delta-Hexanolactone 20V, Positive-QTOF | splash10-05mo-9000000000-af79a590764da1c7c98b | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - delta-Hexanolactone 40V, Positive-QTOF | splash10-052f-9000000000-1ec743e53de2d7795d1d | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - delta-Hexanolactone 10V, Negative-QTOF | splash10-03di-0900000000-58c4fccfebd32004befc | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - delta-Hexanolactone 20V, Negative-QTOF | splash10-08fr-9400000000-d0fcd442f030fde74723 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - delta-Hexanolactone 40V, Negative-QTOF | splash10-0a4l-9000000000-70de17ba043eec91698d | 2021-09-24 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Experimental 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | 2012-12-05 | Wishart Lab | View Spectrum |
IR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+) | 2023-02-03 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+) | 2023-02-03 | FELIX lab | View Spectrum |
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