Details of Metabolite

General Information of MET (ID: META00541)
Name 8(S)-HETE
Synonyms   Click to Show/Hide Synonyms of This Metabolite
(5Z,8S,9E,11Z,14Z)-8-Hydroxyeicosa-5,9,11,14-tetraenoate; (5Z,8S,9E,11Z,14Z)-8-Hydroxyeicosa-5,9,11,14-tetraenoic acid; (5Z,8S,9E,11Z,14Z)-8-Hydroxyicosa-5,9,11,14-tetraenoate; (5Z,8S,9E,11Z,14Z)-8-Hydroxyicosa-5,9,11,14-tetraenoic acid; (5Z,9E,11Z,14Z)-(8S)-8-Hydroxyeicosa-5,9,11,14-tetraenoate; (5Z,9E,11Z,14Z)-(8S)-8-Hydroxyeicosa-5,9,11,14-tetraenoic acid; (5Z,9E,11Z,14Z)-(8S)-8-Hydroxyicosa-5,9,11,14-tetraenoate; (5Z,9E,11Z,14Z)-(8S)-8-Hydroxyicosa-5,9,11,14-tetraenoic acid; (8S)-Hydroxy-(5Z),(9E),(11Z),(14Z)-eicosatetraenoate; (8S)-Hydroxy-(5Z),(9E),(11Z),(14Z)-eicosatetraenoic acid; (S)-(Z,e,Z,Z)-8-Hydroxyeicosa-5,9,11,14-tetraenoate; (S)-(Z,e,Z,Z)-8-Hydroxyeicosa-5,9,11,14-tetraenoic acid; 8(S)-Hydroxy-(5Z,9E,11Z,14Z)-eicosatetraenoate; 8(S)-Hydroxy-(5Z,9E,11Z,14Z)-eicosatetraenoic acid; 8(S)-Hydroxyeicosatetraenoate; 8(S)-Hydroxyeicosatetraenoic acid; 8-Hydroxyeicosatetraenoic acid; 8-Hydroxyeicosatetraenoic acid, (e,Z,Z,Z)-(+-)-isomer; 8-Hydroxyeicosatetraenoic acid, (e,Z,Z,Z)-isomer; 8S-HETE; 8S-Hydroxy-5Z,9E,11Z,14Z-eicosatetraenoate; 8S-Hydroxy-5Z,9E,11Z,14Z-eicosatetraenoic acid
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
5283154
HMDB ID
HMDB0004679
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
C14776
ChEBI ID
34486
FooDB ID
FDB023400
ChemSpider ID
4446278
Physicochemical Properties Molecular Weight 320.5 Topological Polar Surface Area 57.5
XlogP 5.2 Complexity 392
Heavy Atom Count 23 Rotatable Bond Count 14
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 3
Function
8(S)-HETE is a naturally occurring hydroxyeicosatetraenoic acid eicosanoid. 8(S)-HETE is a strong activator of peroxisome proliferator-activated receptors (PPARs) alpha and a weak activator of PPAR gamma. PPARs are nuclear hormone receptors that regulate gene transcription in response to peroxisome proliferators and fatty acids. PPARs also play an important role in the regulation of adipocyte differentiation. It is unclear however what naturally occurring compounds activate each of the PPAR subtypes. Additionally, 8(S)-HETE is able to induce differentiation of preadipocytes.
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 8(S)-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 8(S)-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.

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