Transformation of 5-HETE to 5-OXO-ETE

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The metabolism of 5-HETE to 5-Oxo-ETE is catalysed by the enzyme 5-Hydroxyeicosanoid dehydrogenase (5-HEDH). This enzyme acts reversibly and has been reported to be found in eosinophils, monocytes, DC, B-lymphocytes, keratinocytes and platelets (Steinhilber book) *skin (need to check). The product binds with the OXE receptor (Hosoi2002) and is 30-100 more bioactive than 5-HETE. 5-Oxo-ETE is a chemoattractant for neutrophils and eosinophils.


Reaction

R14 HETE5-OETE5.jpg

Chemical equation

5-HETE \rightleftharpoons 5-Oxo-ETE

Rate equation

R14.PNG

Parameters

Note: Limited availability of kinetic data for specific enzyme, using general alcohol dehydrogenase (ADH) data when non is available.

Michaelis-Menten Constants
Value Units Species Notes Reference
0.0006 mM Unkown Follows a ping-pong mechanism by binding with NADP+, transforming it to NADPH and releasing it before binding 5S-HETE. [1]
0.00067 mM Human Cell lines Follows a ping-pong mechanism by binding with NADP+ (Km 139 nM), transforming it to NADPH (inhibited by NADPH (Ki 224 nM)) and releasing it before binding 5S-HETE.

Method: In vitro Organism: Human Expression vector: U937 and HL-60 cell lines Enzyme:5-HEDH pH: 7.4 Temperature: 37 ◦C

[2]
0.000516 ± 0.00019 mM Human Cell lines

Method: In vitro Organism: Human Expression vector: U937 Enzyme:5-HEDH pH: 7.4 Temperature: 37 ◦C

[3]
Vmax
Value Units Species Notes Reference
0.54 ± 0.30 pmol/ mi mg Human Cell lines - Neutrophils

Method: In vitro Organism: Human Expression vector: U937 and HL-60 cell lines Enzyme:5-HEDH pH: 7.4 Temperature: 37 ◦C

[2]
0.40 ± 0.12 pmol/ mi mg Human Cell lines - U937

Method: In vitro Organism: Human Expression vector: U937 and HL-60 cell lines Enzyme:5-HEDH pH: 7.4 Temperature: 37 ◦C

[2]
Enzyme Turnover Number
Value Units Species Notes Reference
11640 ± 840 min-1 Yokenella Method: In vitro

Organism: Human Expression vector: E Coli Enzyme: pH: 6.5 Temperature: 65 ◦C

Substrate: NADPH

B
5-HEDH Abundance (Using ADH5 abundance data)
Value Units Species Notes Reference
490 ppm Human Expression Vector: Skin

Enzyme: ADH5 pH: 7.5 Temperature: 37 °C

[4]
625 ppm Human Expression Vector: Oral Cavity

Enzyme: ADH5 pH: 7.5 Temperature: 37 °C

[4]
728 ppm Human Expression Vector: Esophagus

Enzyme: ADH5 pH: 7.5 Temperature: 37 °C

[5]
11.5 ppm Human Expression Vector: Skin

Enzyme: ADH5 pH: Unknown Temperature: Unknown

[5]
Gibbs Free energy
Value Units Species Notes Reference
1.29 kcal/mol Arabidopsis thaliana col Same reaction, no prediction available for 5-HEDH on Metacyc

Estimated Enzyme: ω-hydroxy fatty acid ω-alcohol dehydrogenase Substrate: 18-hydroxyoleate Product: 18-oxo-oleate pH: 7.3 ionic strength: 0.25

[6]

Related Reactions

References

  1. ↑ Lipoxygenases in Inflammation - edited by Dieter Steinhilber
  2. ↑ 2.0 2.1 2.2 [https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1828885/pdf/bj4030157.pdf Karl-Rudolf ERLEMANN, Regulation of 5-hydroxyeicosanoid dehydrogenase activity in monocytic cells, Biochem. J. (2007) 403, 157–165]
  3. ↑ [http://jpet.aspetjournals.org/content/jpet/329/1/335.full.pdf Karl-Pranav Patel, Selectivity of 5-Hydroxyeicosanoid Dehydrogenase and Its Inhibition by 5-Hydroxy-Long-Chain Fatty Acids, Journal of Pharmacology and Experimental Therapeutics April 2009, 329 (1) 335-341; ]
  4. ↑ 4.0 4.1 [http://www.nature.com/nature/journal/v509/n7502/pdf/nature13319.pdf M. Wilhelm Mass-spectrometry-based draft of the human proteome Nature, 2014 509, 582–587]
  5. ↑ 5.0 5.1 M. Kim A draft map of the human proteome Nature, 2014 509, 575–581
  6. ↑ Caspi et al 2014, "The MetaCyc database of metabolic pathways and enzymes and the BioCyc collection of Pathway/Genome Databases," Nucleic Acids Research 42:D459-D471
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