Details of Metabolite

General Information of MET (ID: META00539)
Name 13-HODE
Synonyms   Click to Show/Hide Synonyms of This Metabolite
(+)-Coriolic acid; (13S)-Hydroxyoctadecadienoate; (13S)-Hydroxyoctadecadienoic acid; (13S,9Z,11E)-13-Hydroxy-9,11-octadecadienoic acid; (9Z, 11E)-(13S)-13-Hydroxyoctadeca-9,11-dienoate; (9Z, 11E)-(13S)-13-Hydroxyoctadeca-9,11-dienoic acid; (9Z,11E)-(13S)-13-Hydroxyoctadeca-9,11-dienoate; (9Z,11E)-(13S)-13-Hydroxyoctadeca-9,11-dienoic acid; (9Z,11E)-13-HODE; (9Z,11E)-13-Hydroxy-9,11-octadecadienoic acid; (9Z,11E)-13-hydroxyoctadecadienoic acid; (9Z,11E,13S)-13-Hydroxy-9,11-octadecadienoic acid; (9Z,11E,13S)-13-Hydroxyoctadeca-9,11-dienoate; (9Z,11E,13S)-13-Hydroxyoctadecadienoic acid; 13(S) HODE; 13-HODE; 13-Hydroxy-9(Z),11(e)-octadecadienoic acid; 13-Hydroxy-9,11-cis,trans-octadecadienoic acid; 13-Hydroxy-9,11-octadecadienoic acid; 13-Hydroxy-9,11-octadecadienoic acid, (S)-(e,Z)-isomer; 13-Hydroxy-9,11-octadecadienoic acid, (Z,e)-isomer; 13-Hydroxy-9,11-octadecadienoic acid, (e,Z)-isomer; 13-Hydroxy-9-cis-11-trans-octadecadienoic acid; 13-Hydroxy-cis-9-trans-11-octadecadienoic acid; 13-Hydroxylinoleic acid; 13-Hydroxyoctadeca-9,11-dienoic acid; 13-Hydroxyoctadecadienoate; 13-Hydroxyoctadecadienoic acid; 13S-HODE; 13S-Hydroxy-9Z,11E-octadecadienoic acid; 13S-Hydroxyoctadecadienoate; FA(18:2(9Z,11E,13-OH)); FA(18:2(9Z,11E,13S-OH)); L-13-Hydroxy-cis-9,trans-11-octadecadienoic acid
Source Endogenous;Fatty acyls;Food;Drug;TCM Ingredients
Structure Type   Lineolic acids and derivatives  (Click to Show/Hide the Complete Structure Type Hierarchy)
Lipids and lipid-like molecules
Fatty Acyls
Lineolic acids and derivatives
PubChem CID
6443013
HMDB ID
HMDB0004667
Formula
C18H32O3
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
C14762
DrugBank ID
DB06926
ChEBI ID
34154
FooDB ID
FDB023395
ChemSpider ID
4947055
Physicochemical Properties Molecular Weight 296.4 Topological Polar Surface Area 57.5
XlogP 5.3 Complexity 295
Heavy Atom Count 21 Rotatable Bond Count 14
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 3
Function
13-Hydroxyoctadecadienoic acid (13-HODE) (CAS: 18104-45-5), also known as 13(S)-hydroxy-9Z,11E-octadecadienoic acid or 13(S)-HODE, is the major lipoxygenation product synthesized in the body from linoleic acid. 13-HODE prevents cell adhesion to endothelial cells and can inhibit cancer metastasis. 13-HODE synthesis is enhanced by cyclic AMP. gamma-Linolenic acid, a desaturated metabolite of linoleic acid, causes substantial stimulation of 13-HODE synthesis. A fall in gamma-linolenic acid synthesis with age may be related to the age-related fall in 13-HODE formation. 13-HODE is considered an intermediate in linoleic acid metabolism. It is generated from 13(S)-HPODE via the enzyme lipoxygenase (EC 1.13.11.12). 13-HODE has been shown to be involved in cell proliferation and differentiation in a number of systems. 13-HODE is found to be produced by prostate tumours and cell lines and researchers believe that there is a link between linoleic acid metabolism and the development or progression of prostate cancer.
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 13-HODE concentration: decrease
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that knockout of Pla2g3 leads to the decrease of 13-HODE levels compared with control group.
      Transferases (EC 2)
            Arylamine N-acetyltransferase 1 (NAT1) 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 Knockout of NAT1
                      Induced Change 13-HODE concentration: increase (FC = 2.5)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Breast cancer [ICD-11: 2C60]
                      Details It is reported that knockout of NAT1 leads to the increase of 13-HODE 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 CRISPR/Cas9 knockout of human arylamine N-acetyltransferase 1 in MDA-MB-231 breast cancer cells suggests a role in cellular metabolism. Sci Rep. 2020 Jun 17;10(1):9804.

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