Structure Database (LMSD)

Common Name
12R-HETE
Systematic Name
12R-hydroxy-5Z,8Z,10E,14Z-eicosatetraenoic acid
Synonyms
  • 12-HETE
LM ID
LMFA03060008
Formula
Exact Mass
Calculate m/z
320.235146
Sum Composition
Status
Curated

Classification

Biological Context

12(R)-HETE is an endogenous active metabolite of the ω-6 PUFA and eicosanoid precursor arachidonic acid.1,2 It is formed from arachidonic acid by 12R-lipoxygenase (12R-LO), as well as cytochrome P450s (CYPs). 12(R)-HETE binds to the TP receptor in washed isolated human platelets (IC50 = 0.734 µM) and inhibits platelet aggregation induced by the TP receptor agonist I-BOP (; IC50 = 3.6 µM).3 It also selectively binds to leukotriene B4 (LTB4) receptor 2 (BLT2) over BLT1 at 5 µM in CHO cell membranes expressing the human receptors.4 It increases the proliferation of HT-29 colon cancer cells when used at a concentration of 1 µM.5 12(R)-HETE inhibits the bovine corneal Na+/K+-ATPase in a concentration-dependent manner and decreases intraocular pressure in rabbits when administered topically at doses of 1, 10, or 50 µg/eye.6,7 Intracerebroventricular administration of 12(R)-HETE (10 µg/animal) decreases LPS-induced pyresis in rats.8

This information has been provided by Cayman Chemical

References

String Representations

InChiKey (Click to copy)
ZNHVWPKMFKADKW-ZYBDYUKJSA-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-/m1/s1
SMILES (Click to copy)
C(/CCCC(=O)O)=C/C/C=C\C=C\[C@H](O)C/C=C\CCCCC

Other Databases

KEGG ID
CHEBI ID
LIPIDBANK ID
DFA8136
PubChem CID
SwissLipids ID
Cayman ID
GuidePharm 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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Created at
-
Updated at
21st Nov 2021