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8 (9) -EET

CAT: 0804-HY-160431Size: 1 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-160431Size:1 mg
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Description
8 (9) -EET is one of the main metabolites produced by the metabolism of arachidonic acid through the cytochrome P450 epoxide pathway. 8 (9) -EET is an effective substrate for COX-1 and COX-2. 8 (9) -EET activates PPARα in HEK293 cells and inhibits the activity of NF-κB induced by IL-1β in a PPARα-dependent and -independent manner. The (8S,9R) -isomer of 8 (9) -EET ([ (8S,9R) -EET]) causes vasoconstriction, thereby reducing renal plasma flow and glomerular filtration rate[1][2][3][4][5].
CAS Number
82864-43-5
UNSPSC
12352005
Target
COX; Drug Metabolite; NF-κB; PPAR
Related Pathways
Cell Cycle/DNA Damage; Immunology/Inflammation; Metabolic Enzyme/Protease; NF-κB; Vitamin D Related/Nuclear Receptor
Applications
Metabolism-protein/nucleotide metabolism
Field of Research
Metabolic Disease
Smiles
CCCCC/C=C\C/C=C\C[C@H]1[C@H](O1)C/C=C\CCCC(O)=O
Molecular Formula
C20H32O3
Molecular Weight
320.47
References & Citations
[1]Chacos, N., Falck, J.R., Wixtrom, C., et al. Novel epoxides formed during the liver cytochrome P-450 oxidation of arachidonic acid. Biochem. Biophys. Res. Commun. 104 (3), 916-922 (1982) .|[2]Zhang, J.Y., Prakash, C., Yamashita, K., et al. Regiospecific and enantioselective metabolism of 8,9-epoxyeicosatrienoic acid by cyclooxygenase. Biochem. Biophys. Res. Commun. 183 (1), 138-143 (1992) .|[3]Bystrom, J., Wray, J.A., Sugden, M.C., et al. Endogenous epoxygenases are modulators of monocyte/macrophage activity. PloS One 6 (10), e26591 (2011) .|[4]Rand, A.A., Barnych, B., Morisseau, C., et al. Cyclooxygenase-derived proangiogenic metabolites of epoxyeicosatrienoic acids. Proc. Natl. Acad. Sci. USA 114 (17), 4370-4375 (2017) .|[5]Katoh T, et al. Glomerular stereospecific synthesis and hemodynamic actions of 8,9-epoxyeicosatrienoic acid in rat kidney. Am J Physiol. 1991 Oct;261 (4 Pt 2) :F578-86.
Shipping Conditions
Room temperature
Scientific Category
Reference compound1
Clinical Information
No Development Reported

Chemical Information

8(9)-Eet
CAS Number82864-43-5
PubChem CID6440706
IUPAC Name(Z)-7-[(2R,3S)-3-[(2Z,5E)-undeca-2,5-dienyl]oxiran-2-yl]hept-5-enoic acid
Molecular FormulaC20H32O3
Molecular Weight320.5
XLogP5.4
Topological Polar Surface Area49.8
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count3
Rotatable Bond Count14
Heavy Atom Count23
Formal Charge0
Complexity396
SMILES
CCCCC/C=C/C/C=C\C[C@H]1[C@H](O1)C/C=C\CCCC(=O)O
InChI
InChI=1S/C20H32O3/c1-2-3-4-5-6-7-8-9-12-15-18-19(23-18)16-13-10-11-14-17-20(21)22/h6-7,9-10,12-13,18-19H,2-5,8,11,14-17H2,1H3,(H,21,22)/b7-6+,12-9-,13-10-/t18-,19+/m0/s1
InChIKey
DBWQSCSXHFNTMO-YCBVFNAUSA-N
Chemical Structure
2D Structure
2D structure of 8(9)-Eet
CAS: 82864-43-5
CID: 6440706
Formula: C20H32O3
MW: 320.5
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight320.5
XLogP35.4
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count3
Rotatable Bond Count14
Exact Mass320.23514488
Monoisotopic Mass320.23514488
Topological Polar Surface Area49.8 Ų
Heavy Atom Count23
Formal Charge0
Complexity396
Isotope Atom Count0
Defined Atom Stereocenter Count2
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count3
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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