Details of Metabolite

General Information of MET (ID: META00583)
Name 12-HEPE
Synonyms   Click to Show/Hide Synonyms of This Metabolite
(+-)-12-HEPE; (+-)-12-Hydroxy-5Z,8Z,10E,14Z,17Z-eicosapentaenoate; (+-)-12-Hydroxy-5Z,8Z,10E,14Z,17Z-eicosapentaenoic acid; (5Z,8Z,10E,14Z,17Z)-12-Hydroxyeicosa-5,8,10,14,17-pentaenoate; (5Z,8Z,10E,14Z,17Z)-12-Hydroxyeicosa-5,8,10,14,17-pentaenoic acid; 12-HEP; 12-Hydroxy-5,8,10,14,17-eicosapentaenoate; 12-Hydroxy-5,8,10,14,17-eicosapentaenoic acid; 12-Hydroxy-5,8,10,14,17-eicospentaenoic acid; 12-Hydroxy-5,8,10,14,17-eicospentaenoic acid, (e,Z,Z,Z,Z)-isomer; 12-Hydroxy-5Z,8Z,10E,14Z,17Z-icosapentaenoate; 12-Hydroxy-5Z,8Z,10E,14Z,17Z-icosapentaenoic acid; 12-Hydroxyeicosapentaenoate; 12-Hydroxyeicosapentaenoic acid; 12-Hydroxyicosa-(5Z,8Z,10E,14Z,17Z)-pentaenoate; 12-Hydroxyicosa-(5Z,8Z,10E,14Z,17Z)-pentaenoic 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
10041593
HMDB ID
HMDB0010202
Formula
C20H30O3
Structure
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3D MOL 2D MOL
  Click to Show/Hide the Molecular/Functional Data (External Links/Property/Function) of This Metabolite
ChEBI ID
72645
FooDB ID
FDB027357
ChemSpider ID
8217157
Physicochemical Properties Molecular Weight 318.4 Topological Polar Surface Area 57.5
XlogP 4.5 Complexity 428
Heavy Atom Count 23 Rotatable Bond Count 13
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 3
Function
12-HEPE is hydroxy derivative of 12-lipoxygenase metabolites of Eicosapentaenoic acid (EPA). 12S-HEPE participates in platelet-neutrophil interactions in a manner similar to 12S-HETE. It can also compete with endogenous arachidonic acid for 5-lipoxygenation in stimulated human neutrophils. By providing competing substrates for neutrophil 5-lipoxygenase, platelets might contribute to the antiinflammatory potential of dietary n-3 fatty acids through platelet-neutrophil interaction. ( PMID: 2116491).
Regulatory Network
Full List of Protein(s) Regulating This Metabolite
      Hydrolases (EC 3)
            Group 10 secretory phospholipase A2 (PLA2G10) 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 Overexpression of Pla2g10
                      Induced Change 12-HEPE concentration: increase
                      Summary Introduced Variation         Induced Change 
                      Disease Status Inflammatory bowel disease [ICD-11: DD72]
                      Details It is reported that overexpression of Pla2g10 leads to the increase of 12-HEPE levels compared with control group.
References
1 Group X Secreted Phospholipase A2 Releases 3 Polyunsaturated Fatty Acids, Suppresses Colitis, and Promotes Sperm Fertility. J Biol Chem. 2016 Mar 25;291(13):6895-911.

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