Structure Database (LMSD)

Common Name
5R-HETE
Systematic Name
5R-hydroxy-6E,8Z,11Z,14Z-eicosatetraenoic acid
Synonyms
LM ID
LMFA03060024
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 NP-MRD ID(NMR) spectrum

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

5(R)-HETE is a rare lipoxygenase product of arachidonic acid. Nearly all plant and animal 5-LOs produce 5(S)-HETE, but the presence of a 5(R)-LO and the synthesis of 5(R)-HpETE and 5(R)-HETE have been confirmed in oocytes of the bivalve mollusk, S. solidissima.1 5(R)-HETE is more potent than the (S)-enantiomer as a chemotactic agent for human neutrophils.2

This information has been provided by Cayman Chemical

References

1. Hada, T., Swift, L.L., and Brash, A.R. Discovery of 5R-lipoxygenase activity in oocytes of the surf clam, Spisula solidissima. Biochim. Biophys. Acta 1346(2), 109-119 (1997).
2. Bittleman, D.B., and Casale, T.B. 5-Hydroxyeicosatetraenoic acid (HETE)-induced neutrophil transcellular migration is dependent upon enantiomeric structure. Am. J. Respir. Cell Mol. Biol. 12, 260-267 (1995).

String Representations

InChiKey (Click to copy)
KGIJOOYOSFUGPC-CABOLEKPSA-N
InChi (Click to copy)
InChI=1S/C20H32O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-19(21)17-15-18-20(22)23/h6-7,9-10,12-14,16,19,21H,2-5,8,11,15,17-18H2,1H3,(H,22,23)/b7-6-,10-9-,13-12-,16-14+/t19-/m0/s1
SMILES (Click to copy)
C(/C/C=C\C/C=C\CCCCC)=C/C=C/[C@H](O)CCCC(=O)O

Other Databases

CHEBI ID
165284
LIPIDBANK ID
DFA8128
PubChem CID
5283165
Cayman ID
34225

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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Created at
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Updated at
14th Oct 2024