Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2008-10-29 12:41:53 UTC |
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Update Date | 2022-03-07 02:51:03 UTC |
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HMDB ID | HMDB0011135 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 5-HPETE |
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Description | 5-HPETE, also known as 5(S)-hpete, belongs to the class of organic compounds known as hydroperoxyeicosatetraenoic acids. These are eicosanoic acids with an attached hydroperoxyl group and four CC double bonds. Thus, 5-HPETE is considered to be an eicosanoid lipid molecule. 5-HPETE is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. |
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Structure | CCCCC\C=C/C\C=C/C\C=C/C=C/C(CCCC(O)=O)OO InChI=1S/C20H32O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-19(24-23)17-15-18-20(21)22/h6-7,9-10,12-14,16,19,23H,2-5,8,11,15,17-18H2,1H3,(H,21,22)/b7-6-,10-9-,13-12-,16-14+ |
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Synonyms | Value | Source |
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(6E,8Z,11Z,14Z)-5-Hydroperoxyicosatetraenoic acid | HMDB | 5-Hydroperoxy-(6E,8Z,11Z,14Z)-eicosatetraenoic acid | HMDB | 5-Hydroperoxy-(6E,8Z,11Z,14Z)-icosatetraenoic acid | HMDB | 6,8,11,14-Eicosatetraenoic acid 5-hydroperoxide | HMDB | Arachidonic acid 5-hydroperoxide | HMDB | (6E,8Z,11Z,14Z)-5-Hydroperoxyicosatetraenoate | HMDB | 5-Hydroperoxy-(6E,8Z,11Z,14Z)-eicosatetraenoate | HMDB | 5-Hydroperoxy-(6E,8Z,11Z,14Z)-icosatetraenoate | HMDB | 6,8,11,14-Eicosatetraenoate 5-hydroperoxide | HMDB | Arachidonate 5-hydroperoxide | HMDB | (5S,6E,8Z,11Z,14Z)-5-Hydroperoxyicosa-6,8,11,14-tetraenoate | HMDB | (5S,6E,8Z,11Z,14Z)-5-Hydroperoxyicosa-6,8,11,14-tetraenoic acid | HMDB | (6E,8Z,11Z,14Z)-(5S)-5-Hydroperoxyeicosa-6,8,11,14-tetraenoate | HMDB | (6E,8Z,11Z,14Z)-(5S)-5-Hydroperoxyeicosa-6,8,11,14-tetraenoic acid | HMDB | 5(S)-HPETE | HMDB | 5(S)-Hydroperoxy-6-trans-8,11,14-cis-eicosatetraenoate | HMDB | 5(S)-Hydroperoxy-6-trans-8,11,14-cis-eicosatetraenoic acid | HMDB | 5-Hydroperoxy-6,8,11,14-eicosatetraenoic acid | HMDB | cis,trans-5-Hydroperoxy-6,8,11,14-eicosatetraenoic acid | HMDB |
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Chemical Formula | C20H32O4 |
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Average Molecular Weight | 336.4657 |
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Monoisotopic Molecular Weight | 336.230059512 |
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IUPAC Name | (6E,8Z,11Z,14Z)-5-hydroperoxyicosa-6,8,11,14-tetraenoic acid |
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Traditional Name | (6E,8Z,11Z,14Z)-5-hydroperoxyicosa-6,8,11,14-tetraenoic acid |
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CAS Registry Number | 74581-83-2 |
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SMILES | CCCCC\C=C/C\C=C/C\C=C/C=C/C(CCCC(O)=O)OO |
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InChI Identifier | InChI=1S/C20H32O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-19(24-23)17-15-18-20(21)22/h6-7,9-10,12-14,16,19,23H,2-5,8,11,15,17-18H2,1H3,(H,21,22)/b7-6-,10-9-,13-12-,16-14+ |
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InChI Key | JNUUNUQHXIOFDA-XTDASVJISA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as hydroperoxyeicosatetraenoic acids. These are eicosanoic acids with an attached hydroperoxyl group and four CC double bonds. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Fatty Acyls |
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Sub Class | Eicosanoids |
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Direct Parent | Hydroperoxyeicosatetraenoic acids |
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Alternative Parents | |
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Substituents | - Hydroperoxyeicosatetraenoic acid
- Long-chain fatty acid
- Hydroperoxy fatty acid
- Fatty acid
- Unsaturated fatty acid
- Allylic hydroperoxide
- Hydroperoxide
- Carboxylic acid derivative
- Alkyl hydroperoxide
- Carboxylic acid
- Peroxol
- Monocarboxylic acid or derivatives
- Carbonyl group
- Organooxygen compound
- Hydrocarbon derivative
- Organic oxide
- Organic oxygen compound
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | Not Available |
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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | |
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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 | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | | Show more...
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatized | Show more...
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Spectra |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - 5-HPETE GC-MS (Non-derivatized) - 70eV, Positive | splash10-0ufv-7293000000-1f097659cf0dcff9bef9 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 5-HPETE GC-MS (1 TMS) - 70eV, Positive | splash10-00bl-9145000000-04747e5703a025ef8f4f | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 5-HPETE 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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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5-HPETE 10V, Positive-QTOF | splash10-014i-0129000000-4500aedb60e4f301fc49 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5-HPETE 20V, Positive-QTOF | splash10-000l-5895000000-d22ccb32f3d2e86a7abe | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5-HPETE 40V, Positive-QTOF | splash10-0f6x-7960000000-eeee1d1eae1b6538345d | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5-HPETE 10V, Negative-QTOF | splash10-000i-0029000000-5771c8b8f884a5a6e792 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5-HPETE 20V, Negative-QTOF | splash10-00kr-3189000000-2e7fb2d06fbec5bc6900 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5-HPETE 40V, Negative-QTOF | splash10-0pbc-9160000000-f9cca7f9dfab4a0ee121 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5-HPETE 10V, Positive-QTOF | splash10-000i-1369000000-fdc7ed645955c857b4f6 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5-HPETE 20V, Positive-QTOF | splash10-00li-6924000000-769a1698f7fc3038abd9 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5-HPETE 40V, Positive-QTOF | splash10-05nf-9300000000-13e0c97d67ef1cdf5fc0 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5-HPETE 10V, Negative-QTOF | splash10-000i-0009000000-4313d8567d98daeec5be | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5-HPETE 20V, Negative-QTOF | splash10-0k9i-2069000000-56e8fbe6c944c9901664 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5-HPETE 40V, Negative-QTOF | splash10-052f-9330000000-a6266812ce67a6e4e4f6 | 2021-09-23 | Wishart Lab | View Spectrum |
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Biological Properties |
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Cellular Locations | |
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Biospecimen Locations | Not Available |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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| Not Available |
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Abnormal Concentrations |
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| Not Available |
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Associated Disorders and Diseases |
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Disease References | None |
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Associated OMIM IDs | None |
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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 | FDB027913 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 4446295 |
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KEGG Compound ID | C05356 |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Arachidonic acid 5-hydroperoxide |
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METLIN ID | Not Available |
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PubChem Compound | 5283171 |
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PDB ID | Not Available |
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ChEBI ID | 91268 |
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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 | Not Available |
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References |
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Synthesis Reference | Not Available |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - Winkler JD, Sung CM, Hubbard WC, Chilton FH: Influence of arachidonic acid on indices of phospholipase A2 activity in the human neutrophil. Biochem J. 1993 May 1;291 ( Pt 3):825-31. [PubMed:8387780 ]
- Seya A, Terano T, Tamura Y, Yoshida S: The role of 5-hydroperoxyeicosatetraenoic acid in neutrophil activation. Agents Actions. 1992 Sep;37(1-2):121-6. [PubMed:1456173 ]
- Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
- Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
- Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
- Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
- Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
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