Details of Metabolite

General Information of MET (ID: META00527)
Name 15-HETE
Synonyms   Click to Show/Hide Synonyms of This Metabolite
(15S)-15-Hydroxy-5,8,11-cis-13-trans-eicosatetraenoate; (15S)-15-Hydroxy-5,8,11-cis-13-trans-eicosatetraenoic acid; (15S)-15-Hydroxy-5,8,11-cis-13-trans-eicosic acid; (15S)-15-Hydroxy-5,8,11-cis-13-trans-icosatetraenoate; (15S)-15-Hydroxy-5,8,11-cis-13-trans-icosatetraenoic acid; (15S)-Hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoate; (15S)-Hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoic acid; (15S)-Hydroxyeicosa-(5Z,8Z,11Z,13E)-tetraenoate; (15S)-Hydroxyeicosa-(5Z,8Z,11Z,13E)-tetraenoic acid; (15S,5Z,8Z,11Z,13E)-15-Hydroxyeicosatetraenoate; (15S,5Z,8Z,11Z,13E)-15-Hydroxyeicosatetraenoic acid; (5Z,8Z,11Z,13E)-(15S)-15-Hydroxyicosa-5,8,11,13-tetraenoate; (5Z,8Z,11Z,13E)-(15S)-15-Hydroxyicosa-5,8,11,13-tetraenoic acid; (5Z,8Z,11Z,13E,15S)-15-Hydroxy-5,8,11,13-eicosatetraenoate; (5Z,8Z,11Z,13E,15S)-15-Hydroxy-5,8,11,13-eicosatetraenoic acid; (5Z,8Z,11Z,13E,15S)-15-Hydroxyeicosa-5,8,11,13-tetraenoate; (5Z,8Z,11Z,13E,15S)-15-Hydroxyeicosa-5,8,11,13-tetraenoic acid; (5Z,8Z,11Z,13E,15S)-15-Hydroxyeicosatetraenoic acid; (S)-15-HETE; 15 Hete; 15(S)-HETE; 15(S)-Hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoate; 15(S)-Hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoic acid; 15(S)-Hydroxy-5,8,11-cis-13-trans-eicosatetraenoic acid; 15(S)-Hydroxy-5Z,8Z,11Z,13E-eicosatetraenoic acid; 15(S)-Hydroxyeicosatetraenoate; 15(S)-Hydroxyeicosatetraenoic acid; 15-HETE; 15-Hydroxy-5,8,11,13-eicosatetraenoic acid; 15-Hydroxy-5,8,11,13-eicosatetraenoic acid, (S-(e,Z,Z,Z))-isomer; 15-Hydroxyeicosatetraenoic acid; 15S-HETE; 15S-Hydroxy-5,8,11,13-(Z,Z,Z,e)-eicosatetraenoic acid; 15S-Hydroxy-5Z,8Z,11Z,13E-eicosatetraenoate; 15S-Hydroxy-5Z,8Z,11Z,13E-eicosatetraenoic acid; FA(20:4(5Z,8Z,11Z,13E,15-OH)); FA(20:4(5Z,8Z,11Z,13E,15S-OH)); Icomucret
Source Endogenous;Fatty acyls;Food
Structure Type   Eicosanoids  (Click to Show/Hide the Complete Structure Type Hierarchy)
Lipids and lipid-like molecules
Fatty Acyls
Eicosanoids
PubChem CID
5280724
HMDB ID
HMDB0003876
Formula
C20H32O3
Structure
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3D MOL 2D MOL
  Click to Show/Hide the Molecular/Functional Data (External Links/Property/Function) of This Metabolite
KEGG ID
C04742
ChEBI ID
15558
FooDB ID
FDB023242
ChemSpider ID
4444307
Physicochemical Properties Molecular Weight 320.5 Topological Polar Surface Area 57.5
XlogP 5.1 Complexity 392
Heavy Atom Count 23 Rotatable Bond Count 14
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 3
Function
15-HETE is a hydroxyeicosatetraenoic acid. Hydroxyeicosatetraenoic acids (HETEs) are formed by the 5-, 12-, and 15-lipoxygenase (LO) pathways. The 5- and 12-LO products are mainly proinflammatory in the skin whereas the main 15-LO product 15-HETE has antiinflammatory capacities. In vitro, 15-HETE has been shown to inhibit LTB4 formation, 12-HETE formation, and specifically inhibits the neutrophil chemotactic effect of LTB4. The inhibition of LTB4 formation is probably due to modulation of the 5-LO because no changes in PGE2 formation have been determined. In vivo, 15-HETE inhibits LTB4-induced erythema and edema, and reduces LTB4 in the synovial fluid of carragheenan-induced experimental arthritis in dogs. 15-HETE also has some immunomodulatory effects. It inhibits the mixed lymphocyte reaction, induces generation of murine cytotoxic suppressor T cells, and it decreases interferon production by murine lymphoma cells. Furthermore, IL-4 and IL-13 have recently been shown to be potent activators of the 15-LO in mononuclear cells. 15(S)-HETE is found to be associated with Zellweger syndrome, which is an inborn error of metabolism.
Regulatory Network
Full List of Protein(s) Regulating This Metabolite
      Hydrolases (EC 3)
            Group 3 secretory phospholipase A2 (PLA2G3) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [1]
                      Introduced Variation Knockout of Pla2g3
                      Induced Change 15-HETE concentration: decrease
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that knockout of Pla2g3 leads to the decrease of 15-HETE levels compared with control group.
            Sulfatase sulf-1 (SULF1) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [2]
                      Introduced Variation Knockdown (shRNA) of SULF1
                      Induced Change 15-HETE concentration: decrease (FC = 0.38 / 0.48)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Ovarian cancer [ICD-11: 2C73]
                      Details It is reported that knockdown of SULF1 leads to the decrease of 15-HETE levels compared with control group.
      Oxidoreductases (EC 1)
            Arachidonate 15-lipoxygenase B (ALOX15B) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [3]
                      Introduced Variation Overexpression of Alox15b
                      Induced Change 15-HETE concentration: increase
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that overexpression of Alox15b leads to the increase of 15-HETE levels compared with control group.
References
1 Group III secreted phospholipase A2 regulates epididymal sperm maturation and fertility in mice. J Clin Invest. 2010 May;120(5):1400-14.
2 Erratum to: Loss of HSulf-1 promotes altered lipid metabolism in ovarian cancer. Cancer Metab. 2014 Nov 4;2:24.
3 Systematic analysis of rat 12/15-lipoxygenase enzymes reveals critical role for spinal eLOX3 hepoxilin synthase activity in inflammatory hyperalgesia. FASEB J. 2013 May;27(5):1939-49.

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