Structure Database (LMSD)
Common Name
5-HPETE
Systematic Name
5-hydroperoxyeicosa-6E,8Z,11Z,14Z-tetraenoic acid
Synonyms
- (6E,8Z,11Z,14Z)-5-hydroperoxyicosa-6,8,11,14-tetraenoic acid
LM ID
LMFA03060108
Formula
Exact Mass
Calculate m/z
336.23006
Sum Composition
Status
Curated
3D model of 5-HPETE
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Biological Context
5(S)-HpETE is a monohydroperoxy polyunsaturated fatty acid (PUFA) produced by the action of 5-LO on arachidonic acid. It is metabolized to leukotriene A4 (LTA4), a key intermediate in the formation of LTs.1 5(S)-HpETE (1 µM) mediates the induction of the proto-oncogene c-fos in TNF-stimulated TA1 cells.2
This information has been provided by Cayman Chemical
References
1. Shimizu, T., Rådmark, O., and Samuelsson, B. Enzyme with dual lipoxygenase activities catalyzes leukotriene A4 synthesis from arachidonic acid. Proc. Natl. Acad. Sci. USA 81, 689-693 (1984).
2. Haliday, E.M., Ramesha, C.S., and Ringold, G. TNF induces c-fos via a novel pathway requiring conversion of arachidonic acid to a lipoxygenase metabolite. EMBO J. 10, 109-115 (1991).
String Representations
InChiKey (Click to copy)
JNUUNUQHXIOFDA-XTDASVJISA-N
InChi (Click to copy)
InChI=1S/C20H32O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-19(24-23)17-15-18-20(21)22/h6-7,9-10,12-14,16,19,23H,2-5,8,11,15,17-18H2,1H3,(H,21,22)/b7-6-,10-9-,13-12-,16-14+
SMILES (Click to copy)
C(/C/C=C\C/C=C\CCCCC)=C/C=C/C(OO)CCCC(=O)O
Other Databases
KEGG ID
HMDB ID
CHEBI ID
PubChem CID
SwissLipids ID
Cayman ID
Calculated Physicochemical Properties
Heavy Atoms
24
Rings
0
Aromatic Rings
0
Rotatable Bonds
15
Van der Waals Molecular Volume
376.52
Topological Polar Surface Area
66.76
Hydrogen Bond Donors
2
Hydrogen Bond Acceptors
4
logP
6.14
Molar Refractivity
99.30
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Updated at
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