Structure Database (LMSD)
Common Name
17-HETE
Systematic Name
17-hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoic acid
Synonyms
3D model of 17-HETE
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Biological Context
Electrolyte and fluid transport in the kidney are regulated in part by arachidonic acid and its metabolites. (±)17-HETE is the racemic version of a cytochrome P450 (CYP450) metabolite of arachidonic acid that has stereospecific effects on sodium transport in the kidney. At a concentration of 2 µM the (S)-enantiomer of 17-HETE inhibits proximal tubule ATPase activity by as much as 70%, whereas the (R)-isomer is inactive.1
This information has been provided by Cayman Chemical
References
1. Carroll, M.A., Balazy, M., Margiotta, P., et al. Cytochrome P-450-dependent HETEs: Profile of biological activity and stimulation by vasoactive peptides. Am. J. Physiol. 271(4 Pt 2), R863-R869 (1996).
References
Taxonomy Information
Curated from
NCBI taxonomy class
Reference
Homo sapiens
(#9606)
Mammalia
(#40674)
Lipidomics reveals a remarkable diversity of lipids in human plasma,
J Lipid Res, 2010
J Lipid Res, 2010
Pubmed ID:
20671299
DOI:
10.1194/jlr.M009449
String Representations
InChiKey (Click to copy)
OPPIPPRXLIDJKN-JPURVOHMSA-N
InChi (Click to copy)
InChI=1S/C20H32O3/c1-2-16-19(21)17-14-12-10-8-6-4-3-5-7-9-11-13-15-18-20(22)23/h3,5-6,8-9,11-12,14,19,21H,2,4,7,10,13,15-18H2,1H3,(H,22,23)/b5-3-,8-6-,11-9-,14-12-
SMILES (Click to copy)
C(/C/C=C\C/C=C\CC(O)CCC)=C/C/C=C\CCCC(=O)O
Other Databases
HMDB ID
CHEBI ID
PubChem CID
SwissLipids ID
Cayman ID
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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