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8 (S),9 (R) -EET

CAT: 0804-HY-150092Size: 1 EachDry Ice: NoHazardous: No
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Description
8 (S),9 (R) -EET is an eicosanoid product of Arachidonic acid (AA; HY-109590) by cytochromes P450. 8 (S),9 (R) -EET dilates canine epicardial arterioles in a concentration-dependent manner with an EC50 value of 121 nM[1][2].
CAS Number
123931-39-5
UNSPSC
12352005
Target
Drug Metabolite
Type
Natural Products
Related Pathways
Metabolic Enzyme/Protease
Applications
Neuroscience-Neuromodulation
Field of Research
Cardiovascular Disease
Assay Protocol
https://www.medchemexpress.com/8-s-9-r-eet.html
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]D C Zeldin, et al. Epoxygenase pathways of arachidonic acid metabolism. J Biol Chem. 2001 Sep 28;276 (39) :36059-62.|[2]Y Zhang, et al. EET homologs potently dilate coronary microvessels and activate BK (Ca) channels. Am J Physiol Heart Circ Physiol. 2001 Jun;280 (6) :H2430-40.
Shipping Conditions
Room temperature
Scientific Category
Natural Products
Clinical Information
No Development Reported

Chemical Information

8S,9R-EpETrE

(8S,9R)-EET is an 8,9-EET in which the epoxy moiety has 8S,9R-configuration. It has a role as a vasoconstrictor agent and a rat metabolite. It is a conjugate acid of an (8S,9R)-EET(1-). It is an enantiomer of an (8R,9S)-EET.

CAS Number123931-39-5
PubChem CID40490656
IUPAC Name(Z)-7-[(2S,3R)-3-[(2Z,5Z)-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+/m1/s1
InChIKey
DBWQSCSXHFNTMO-ZZMPYBMWSA-N
Chemical Structure
2D Structure
2D structure of 8S,9R-EpETrE
CAS: 123931-39-5
CID: 40490656
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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