| Record Information |
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| Version | 2.0 |
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| Created at | 2022-03-17 19:31:47 UTC |
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| Updated at | 2022-03-17 19:31:47 UTC |
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| NP-MRD ID | NP0045556 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | 5-HETE |
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| Description | 5-HETE, also known as 5S-HETE, belongs to the class of organic compounds known as hydroxyeicosatetraenoic acids. These are eicosanoic acids with an attached hydroxyl group and four CC double bonds. Thus, 5-HETE is considered to be an eicosanoid lipid molecule. 5-HETE is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 5-HETE exists in all living organisms, ranging from bacteria to humans. Oxidized glutathione and 5-HETE can be biosynthesized from glutathione and 5-HPETE; which is catalyzed by the enzyme glutathione peroxidase 1. In humans, 5-HETE is involved in mefenamic acid action pathway. Outside of the human body, 5-HETE has been detected, but not quantified in, corns. This could make 5-HETE a potential biomarker for the consumption of these foods. 5-HETE is found in Homo sapiens, Lithothamnion corallioides and Mus musculus. 5-HETE was first documented in 1980 (PMID: 6253824). The activity of this product has not yet been fully evaluated (PMID: 3088130) (PMID: 3017333) (PMID: 6411852) (PMID: 7159548) (PMID: 2836505) (PMID: 15893379). |
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| Structure | CCCCC\C=C/C\C=C/C\C=C/C=C/[C@@H](O)CCCC(O)=O InChI=1S/C20H32O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-19(21)17-15-18-20(22)23/h6-7,9-10,12-14,16,19,21H,2-5,8,11,15,17-18H2,1H3,(H,22,23)/b7-6-,10-9-,13-12-,16-14+/t19-/m1/s1 |
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| Synonyms | | Value | Source |
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| 5-Hydroxyeicosatetraenoate | Kegg | | (6E,8Z,11Z,14Z)-(5S)-5-Hydroxyicosa-6,8,11,14-tetraenoic acid | Kegg | | 5-Hydroxyeicosatetraenoic acid | Generator | | (6E,8Z,11Z,14Z)-(5S)-5-Hydroxyicosa-6,8,11,14-tetraenoate | Generator | | (5S,6E,8Z,11Z,14Z)-5-Hydroxyeicosa-6,8,11,14-tetraenoic acid | HMDB | | (S)-(e,Z,Z,Z)-5-Hydroxyeicosa-6,8,11,14-tetraenoic acid | HMDB | | 5(S)-Hydroxy-6(e),8(Z),11(Z),14(Z)-eicosatetraenoic acid | HMDB | | 5(S)-Hydroxyeicosatetraenoic acid | HMDB | | 5S-HETE | HMDB | | (5S,6E,8Z,11Z,14Z)-5-Hydroxyeicosa-6,8,11,14-tetraenoate | HMDB | | (S)-(e,Z,Z,Z)-5-Hydroxyeicosa-6,8,11,14-tetraenoate | HMDB | | 5(S)-Hydroxy-6(e),8(Z),11(Z),14(Z)-eicosatetraenoate | HMDB | | 5(S)-Hydroxyeicosatetraenoate | HMDB | | 5(S)-HETE | HMDB | | 5(S)-Hydroxy-6-trans-8,11,14-cis-eicosatetraenoate | HMDB | | 5(S)-Hydroxy-6-trans-8,11,14-cis-eicosatetraenoic acid | HMDB | | 5-Hydroxy-6,8,11,14-eicosatetraenoate | HMDB | | 5-Hydroxy-6,8,11,14-eicosatetraenoic acid | HMDB | | 5-L-Hydroxy-6,8,11,14-eicosatetraenoate | HMDB | | 5-L-Hydroxy-6,8,11,14-eicosatetraenoic acid | HMDB | | 5S-Hydroxy-6,8,11,14-eicosatetraenoate | HMDB | | 5S-Hydroxy-6,8,11,14-eicosatetraenoic acid | HMDB | | 5-Hydroxy-6,8,11,14-eicosatetraenoic acid, (e,e,Z,Z)-isomer | HMDB | | 5-Hydroxy-6,8,11,14-eicosatetraenoic acid, (e,Z,Z,Z)-(+-)-isomer | HMDB | | 5-Hydroxy-6,8,11,14-eicosatetraenoic acid, (S)-(e,Z,Z,Z)-isomer | HMDB | | 5-Hydroxy-6,8,11,14-eicosatetraenoic acid, (e,Z,Z,Z)-isomer | HMDB | | 5-Hydroxy-6,8,11,14-eicosatetraenoic acid, R-(e,Z,Z,Z)-isomer | HMDB | | (5S,6E,8Z,11Z,14Z)-5-Hydroxy-6,8,11,14-eicosatetraenoic acid | HMDB | | 5S-Hydroxy-6,8,11,14-(e,Z,Z,Z)-eicosatetraenoic acid | HMDB | | FA(20:4(5-OH,6E,8Z,11Z,14Z)) | HMDB | | FA(20:4(5S-OH,6E,8Z,11Z,14Z)) | HMDB | | 5-HETE | HMDB |
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| Chemical Formula | C20H32O3 |
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| Average Mass | 320.4663 Da |
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| Monoisotopic Mass | 320.23514 Da |
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| IUPAC Name | (5S,6E,8Z,11Z,14Z)-5-hydroxyicosa-6,8,11,14-tetraenoic acid |
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| Traditional Name | 5-hydroxyeicosatetraenoic acid |
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| CAS Registry Number | 70608-72-9 |
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| SMILES | CCCCC\C=C/C\C=C/C\C=C/C=C/[C@@H](O)CCCC(O)=O |
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| InChI Identifier | InChI=1S/C20H32O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-19(21)17-15-18-20(22)23/h6-7,9-10,12-14,16,19,21H,2-5,8,11,15,17-18H2,1H3,(H,22,23)/b7-6-,10-9-,13-12-,16-14+/t19-/m1/s1 |
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| InChI Key | KGIJOOYOSFUGPC-JGKLHWIESA-N |
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| Experimental Spectra |
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| Not Available | | Predicted Spectra |
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| | Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
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| 1D NMR | 13C NMR Spectrum (1D, 25 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| | Chemical Shift Submissions |
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| Not Available | | Species |
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| Species of Origin | |
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| Chemical Taxonomy |
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| Description | Belongs to the class of organic compounds known as hydroxyeicosatetraenoic acids. These are eicosanoic acids with an attached hydroxyl 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 | Hydroxyeicosatetraenoic acids |
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| Alternative Parents | |
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| Substituents | - Hydroxyeicosatetraenoic acid
- Long-chain fatty acid
- Hydroxy fatty acid
- Fatty acid
- Unsaturated fatty acid
- Secondary alcohol
- Carboxylic acid derivative
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Organic oxide
- Organic oxygen compound
- Alcohol
- Hydrocarbon derivative
- Carbonyl group
- Organooxygen compound
- Aliphatic acyclic compound
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| Molecular Framework | Aliphatic acyclic compounds |
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| External Descriptors | |
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| Physical Properties |
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| State | Not Available |
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| Experimental 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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| Predicted Properties | |
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| General References | - Kragballe K, Desjarlais L, Duell EA, Voorhees JJ: In vitro synthesis of 12-hydroxy-eicosatetraenoic acid is increased in uninvolved psoriatic epidermis. J Invest Dermatol. 1986 Jul;87(1):47-52. doi: 10.1111/1523-1747.ep12523561. [PubMed:3088130 ]
- Kanaji K, Okuma M, Sugiyama T, Sensaki S, Ushikubi F, Uchino H: Requirement of free arachidonic acid for leukotriene B4 biosynthesis by 12-hydroperoxyeicosatetraenoic acid-stimulated neutrophils. Biochem Biophys Res Commun. 1986 Jul 31;138(2):589-95. doi: 10.1016/s0006-291x(86)80537-x. [PubMed:3017333 ]
- Pawlowski NA, Kaplan G, Hamill AL, Cohn ZA, Scott WA: Arachidonic acid metabolism by human monocytes. Studies with platelet-depleted cultures. J Exp Med. 1983 Aug 1;158(2):393-412. doi: 10.1084/jem.158.2.393. [PubMed:6411852 ]
- Sasaki T, Asano T, Takakura K, Sano K, Nakamura T, Suzuki N, Imabayashi S, Ishikawa Y: [Cerebral vasospasm and lipid peroxidation--lipid peroxides in the cerebrospinal fluid after subarachnoid hemorrhage]. No To Shinkei. 1982 Dec;34(12):1191-6. [PubMed:7159548 ]
- Hoffman T, Lizzio EF, Suissa J, Rotrosen D, Sullivan JA, Mandell GL, Bonvini E: Dual stimulation of phospholipase activity in human monocytes. Role of calcium-dependent and calcium-independent pathways in arachidonic acid release and eicosanoid formation. J Immunol. 1988 Jun 1;140(11):3912-8. [PubMed:2836505 ]
- Powell WS, Rokach J: Biochemistry, biology and chemistry of the 5-lipoxygenase product 5-oxo-ETE. Prog Lipid Res. 2005 Mar-May;44(2-3):154-83. doi: 10.1016/j.plipres.2005.04.002. Epub 2005 Apr 20. [PubMed:15893379 ]
- Sud'ina GF, Kobel'kov GM, Barskii OA, Varfolomeev SD: [A kinetic scheme of human neutrophil 5-lipoxygenase activity]. Biokhimiia. 1990 Oct;55(10):1795-811. [PubMed:1964097 ]
- Bigby TD, Meslier N: Transcellular lipoxygenase metabolism between monocytes and platelets. J Immunol. 1989 Sep 15;143(6):1948-54. [PubMed:2550547 ]
- Brinkman HJ, van Buul-Wortelboer MF, van Mourik JA: Selective conversion and esterification of monohydroxyeicosatetraenoic acids by human vascular smooth muscle cells: relevance to smooth muscle cell proliferation. Exp Cell Res. 1991 Jan;192(1):87-92. doi: 10.1016/0014-4827(91)90161-m. [PubMed:1984423 ]
- Soter NA: The skin in mastocytosis. J Invest Dermatol. 1991 Mar;96(3):32S-38S; discussion 38S-39S. [PubMed:1672136 ]
- Chabannes B, Poubelle PE, Moliere P, De Medicis R, Lussier A, Lagarde M: Platelets abrogate leukotriene B(4) generation by human blood neutrophils stimulated with monosodium urate monohydrate or f-Met-Leu-Phe in vitro. Lab Invest. 2003 Apr;83(4):491-9. doi: 10.1097/01.lab.0000062855.90029.d8. [PubMed:12695552 ]
- Hosni M, Meskini N, Prigent AF, Anker G, Joulain C, el Habib R, Lagarde M: Diethyldithiocarbamate (ditiocarb sodium) effect on arachidonic acid metabolism in human mononuclear cells. Glutathione peroxidase-like activity. Biochem Pharmacol. 1992 Mar 17;43(6):1319-29. doi: 10.1016/0006-2952(92)90509-h. [PubMed:1314059 ]
- Maderna P, Colli S, Caruso D, Eligini S, Toia A, Galli G, Tremoli E: Quantitative changes of hydroxyacid formation during platelet-neutrophil interaction. J Lab Clin Med. 1993 Mar;121(3):406-14. [PubMed:8383163 ]
- Goetzl EJ: Vitamin E modulates the lipoxygenation of arachidonic acid in leukocytes. Nature. 1980 Nov 13;288(5787):183-5. doi: 10.1038/288183a0. [PubMed:6253824 ]
- Marcus AJ, Safier LB, Broekman MJ, Ullman HL, Islam N, Sorrell TC, Serhan CN, Weissmann G, Oglesby TD, Gorman RR: Production of metabolic products of arachidonic acid during cell-cell interactions. J Allergy Clin Immunol. 1984 Sep;74(3 Pt 2):338-42. doi: 10.1016/0091-6749(84)90126-x. [PubMed:6088611 ]
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