Structure Database (LMSD)

Common Name
15R-HETE
Systematic Name
15R-hydroxy-5Z,8Z,11Z,13E-eicosatetraenoic acid
Synonyms
LM ID
LMFA03060030
Formula
C20H32O3
Exact Mass
Calculate m/z
320.235145
Sum Composition
FA 20:4;O
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
View ion mobility data

Classification

Category
Main Class
Sub Class
Fatty Acyls [FA]
Eicosanoids [FA03]
Hydroxy/hydroperoxyeicosatetraenoic acids [FA0306]
Fatty Acids and Conjugates [FA01]
Unsaturated fatty acids [FA0103]
Hydroxy fatty acids [FA0105]

Biological Context

15(R)-HETE is a monohydroxy fatty acid. It is produced by aspirin-acetylated COX-2 from arachidonic acid and converted into the specialized pro-resolving mediator 15(R)-lipoxin A4 and 15(R)-lipoxin B4 in a transcellular process via 5-lipoxygenase (5-LO).1,2,3,4,5 It is also produced by the cytochrome P450 (CYP) isoform CYP2C9.1,2,3,6 15(R)-HETE can also be formed from arachidonic acid by COX-1 in stimulated human mast cells and accumulates because, unlike 15(S)-HETE , it is not converted to 15-KETE (15-OxoETE) by 15-hydroxyprostaglandin dehydrogenase (15-PGDH).7 It is an agonist of PPARβ/δ, inducing expression of a PPARβ/δ target gene in a reporter assay using NIH3T3 cells.8

This information has been provided by Cayman Chemical

References

1. Naruhn, S., Meissner, W., Adhikary, T., et al. 15-hydroxyeicosatetraenoic acid is a preferential peroxisome proliferator-activated receptor β/δ agonist. Mol. Pharmacol. 77(2), 171-184 (2010).
2. Bylund, J., Ericsson, J., and Oliw, E.H. Analysis of cytochrome P450 metabolites of arachidonic and linoleic acids by liquid chromatography-mass spectrometry with ion trap MS. Anal. Biochem. 265(1), 55-68 (1998).
3. Johnsson, A.-K., Rönnberg, E., Fuchs, D., et al. COX-1 dependent biosynthesis of 15-hydroxyeicosatetraenoic acid in human mast cells. Biochim. Biophys. Acta Mol. Cell Biol. Lipids 1866(5), 158886 (2021).
4. Schneider, C., and Brash, A.R. Stereospecificity of hydrogen abstraction in the conversion of arachidonic acid to 15R-HETE by aspirin-treated cyclooxygenase-2. Implications for the alignment of substrate in the active site. J. Biol. Chem. 275, 4743-4746 (2000).
5. Clària, J., and Serhan, C.N. Aspirin triggers previously undescribed bioactive eicosanoids by human endothelial cell-leukocyte interactions. PNAS USA 92(21), 9475-9479 (1995).
6. Capdevila, J.H., Morrow, J.D., Belosludtsev, Y.Y., et al. The catalytic outcomes of the constitutive and the mitogen inducible isoforms of prostaglandin H2 synthase are markedly affected by glutathione and glutathione peroxidase(s). Biochemistry 34, 3325-3337 (1995).
7. Lecomte, M., Laneuville, O., Ji, C., et al. Acetylation of human prostaglandin endoperoxide synthase-2 (cyclooxygenase-2) by aspirin. J. Biol. Chem. 269(18), 13207-13215 (1994).
8. Serhan, C.N., Hamberg, M., Samuelsson, B., et al. On the stereochemistry and biosynthesis of lipoxin B. Proc. Natl. Acad. Sci. USA 83(7), 1983-1987 (1986).

String Representations

InChiKey (Click to copy)
JSFATNQSLKRBCI-UDQWCNDOSA-N
InChi (Click to copy)
InChI=1S/C20H32O3/c1-2-3-13-16-19(21)17-14-11-9-7-5-4-6-8-10-12-15-18-20(22)23/h4-5,8-11,14,17,19,21H,2-3,6-7,12-13,15-16,18H2,1H3,(H,22,23)/b5-4-,10-8-,11-9-,17-14+/t19-/m1/s1
SMILES (Click to copy)
C(/C/C=C\C=C\[C@H](O)CCCCC)=C/C/C=C\CCCC(=O)O

Other Databases

KEGG ID
C04742
HMDB ID
HMDB0062294
CHEBI ID
63989
LIPIDBANK ID
DFA8139
PubChem CID
5283169
Cayman ID
34710

Calculated Physicochemical Properties

Heavy Atoms 23
Rings 0
Aromatic Rings 0
Rotatable Bonds 14
Van der Waals Molecular Volume 367.73
Topological Polar Surface Area 57.53
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 3
logP 5.47
Molar Refractivity 97.94

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Updated at
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