Details of Metabolite

General Information of MET (ID: META00461)
Name Trioxilin A3
Synonyms   Click to Show/Hide Synonyms of This Metabolite
(5Z,9E,11R,12S,14Z)-8,11,12-Trihydroxyicosa-5,9,14-trienoate; (5Z,9E,11R,12S,14Z)-8,11,12-Trihydroxyicosa-5,9,14-trienoic acid; (5Z,9E,14Z)-(11R,12S)-8,11,12-Trihydroxyeicosa-5,9,14-trienoate; (5Z,9E,14Z)-(11R,12S)-8,11,12-Trihydroxyeicosa-5,9,14-trienoic acid; (5Z,9E,14Z)-(11R,12S)-8,11,12-Trihydroxyicosa-5,9,14-trienoate; (5Z,9E,14Z)-(11R,12S)-8,11,12-Trihydroxyicosa-5,9,14-trienoic acid; (8,11R,12S)-OH 5c9t14t-20:3; (8,11R,12S)-OH 5c9t14t-C20:3; 8,11,12-Teta; 8,11,12-Trihydroxy-5,9,14-eicosatrienoate; 8,11,12-Trihydroxy-5,9,14-eicosatrienoic acid; 8,11R,12S-TriOH 5c9t14c-20:3; 8,11R,12S-TriOH 5c9t14c-C20:3; 8,11R,12S-Trihydroxy-5Z,9E,14Z-eicosatrienoate; 8,11R,12S-Trihydroxy-5Z,9E,14Z-eicosatrienoic 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
5283208
HMDB ID
HMDB0001977
Formula
C20H34O5
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
C14809
ChEBI ID
36203
FooDB ID
FDB022775
ChemSpider ID
4446329
Physicochemical Properties Molecular Weight 354.5 Topological Polar Surface Area 98
XlogP 3.1 Complexity 414
Heavy Atom Count 25 Rotatable Bond Count 15
Hydrogen Bond Donor Count 4 Hydrogen Bond Acceptor Count 5
Function
Trioxilin A3 is the enzymatically formed derivative of Hepoxilin A3. Normal human epidermis incubated with exogenous AA produces 12-oxo-eicosatetraenoic acid (12-oxo-ETE), hepoxilin A3 (HxA3), and hepoxilin B3 (HxB3) through the 12- Lipoxygenase (LO) pathway. 12-LO is the major arachidonic acid (AA) oxygenation pathway in epidermal cells with total product formation generally exceeding cyclooxygenase activity. Platelet-type 12-LO has been found to be the predominant isoenzyme expressed in human and murine skin epidermis. Increased levels of nonesterified hepoxilins and trioxilins occur in the psoriatic scales. Normal human epidermis synthesized only one of the two possible 10-hydroxy epimers of HxB3 whose formation is probably catalyzed by 12-LO. Hepoxilins exert action on plasma permeability on skin, and induce a specific-receptor-dependent Ca2+ mobilization from endogenous sources and the release of AA and diacylglycerols.
Regulatory Network
Full List of Protein(s) Regulating This Metabolite
      Lyases (EC 4)
            Hydroperoxide isomerase ALOXE3 (eLOX-3) 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 Aloxe3
                      Induced Change Trioxilin A3 concentration: decrease
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that knockout of Aloxe3 leads to the decrease of trioxilin A3 levels compared with control group.
References
1 Aloxe3 knockout mice reveal a function of epidermal lipoxygenase-3 as hepoxilin synthase and its pivotal role in barrier formation. J Invest Dermatol. 2013 Jan;133(1):172-80.

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