Structure Database (LMSD)
Common Name
12S-HETE-d8
Systematic Name
12S-hydroxy-5Z,8Z,10E,14Z-eicosatetraenoic acid-d8
Synonyms
3D model of 12S-HETE-d8
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Category
Main Class
Sub Class
Biological Context
12(S)-HETE-d8 is intended for use as an internal standard for the quantification of 12-HETE by GC- or LC-MS. (±)12-HETE is formed via non-enzymatic oxidation of arachidonic acid .1,2 12(S)- and 12(R)-HETE are formed by 12(S)- and 12(R)-lipoxygenase-mediated oxidation of arachidonic acid, respectively.3,4 12(R)-HETE can also be formed by oxidation of arachidonic acid mediated by cytochrome P450s (CYP450s).1
This information has been provided by Cayman Chemical
References
1. Powell, W.S., and Rokach, J. Biosynthesis, biological effects, and receptors of hydroxyeicosatetraenoic acids (HETEs) and oxoeicosatetraenoic acids (oxo-ETEs) derived from arachidonic acid. Biochim. Biophys. Acta 1851(4), 340-355 (2014).
3. Bürger, F., Krieg, P., Marks, F., et al. Positional- and stereo-selectivity of fatty acid oxygenation catalysed by mouse (12S)-lipoxygenase isoenzymes. Biochem J. 348(Pt 2), 329-335 (2000).
References
Comments
Synthetic deuterated standard
Taxonomy Information
Curated from
NCBI taxonomy class
Reference
synthetic construct
(#32630)
Synthetic deuterated standard
String Representations
InChiKey (Click to copy)
ZNHVWPKMFKADKW-OPXGWVKSSA-N
InChi (Click to copy)
InChI=1S/C20H32O3/c1-2-3-4-5-10-13-16-19(21)17-14-11-8-6-7-9-12-15-18-20(22)23/h7-11,13-14,17,19,21H,2-6,12,15-16,18H2,1H3,(H,22,23)/b9-7-,11-8-,13-10-,17-14+/t19-/m0/s1/i7D,8D,9D,10D,11D,13D,17D,19D
SMILES (Click to copy)
C(/[2H])(\CCCC(=O)O)=C(/[2H])\C/C(/[2H])=C(/[2H])\C=C(/[2H])\[C@@]([2H])(O)C/C(/[2H])=C(/[2H])\CCCCC
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Created at
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Updated at
29th Jan 2021