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Prostaglandin D2 Ethanolamide

CAT: 0931-T38389-01Size: 1 mgDry Ice: NoHazardous: No
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CAT#:0931-T38389-01Size:1 mg
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CAS Number
398138-28-8
Target
Others
Related Pathways
Others
Bioactivity
Prostaglandin D2 ethanolamide (PGD2-EA) is a bioactive lipid produced by the sequential metabolism of anandamide (arachidonoyl ethanolamide) by cyclooxygenase (COX) enzymes, in particular by COX-2, and PGD synthase. The biosynthesis of PGD2-EA from anandamide can also be increased when anandamide metabolism is diminished by deletion of fatty acid amide hydrolase. PGD2-EA is inactive against recombinant prostanoid receptors, including the D prostanoid receptor. It increases the frequency of miniature inhibitory postsynaptic currents in primary cultured hippocampal neurons, an effect which is the opposite of that induced by anandamide.. PGD2-EA also induces apoptosis in colorectal carcinoma cell lines.
Smiles
CCCCC[C@H](O)\C=C\[C@@H]1[C@@H](C\C=C/CCCC(=O)NCCO)[C@@H](O)CC1=O
Molecular Formula
C22H37NO5
Molecular Weight
395.53
Shipping Conditions
Ice Packs
Storage Temperature
-20°C

Chemical Information

prostaglandin D2 ethanolamide

Prostaglandin D2 ethanolamide is an N-acylethanolamine resulting from the formal condensation of the carboxy group of prostaglandin D2 with the amino group of ethanolamine. It is a monocarboxylic acid amide and a N-acylethanolamine. It is functionally related to a prostaglandin D2.

CAS Number398138-28-8
PubChem CID5283120
IUPAC Name(Z)-N-(2-hydroxyethyl)-7-[(1R,2R,5S)-5-hydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]-3-oxocyclopentyl]hept-5-enamide
Molecular FormulaC22H37NO5
Molecular Weight395.5
XLogP1.7
Topological Polar Surface Area107
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count5
Rotatable Bond Count14
Heavy Atom Count28
Formal Charge0
Complexity517
SMILES
CCCCC[C@@H](/C=C/[C@@H]1[C@H]([C@H](CC1=O)O)C/C=C\CCCC(=O)NCCO)O
InChI
InChI=1S/C22H37NO5/c1-2-3-6-9-17(25)12-13-19-18(20(26)16-21(19)27)10-7-4-5-8-11-22(28)23-14-15-24/h4,7,12-13,17-20,24-26H,2-3,5-6,8-11,14-16H2,1H3,(H,23,28)/b7-4-,13-12+/t17-,18+,19+,20-/m0/s1
InChIKey
KEYDJKSQFDUAGF-YIRKRNQHSA-N
Chemical Structure
2D Structure
2D structure of prostaglandin D2 ethanolamide
CAS: 398138-28-8
CID: 5283120
Formula: C22H37NO5
MW: 395.5
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight395.5
XLogP31.7
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count5
Rotatable Bond Count14
Exact Mass395.26717328
Monoisotopic Mass395.26717328
Topological Polar Surface Area107 Ų
Heavy Atom Count28
Formal Charge0
Complexity517
Isotope Atom Count0
Defined Atom Stereocenter Count4
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count2
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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