ChemFOnt: Showing chemical card for (±)8(9)-EET Ethanolamide (CFc000008543)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:55:22 UTC

Chemfont ID

CFc000008543

Molecule Identification

Common Name

(±)8(9)-EET Ethanolamide

Definition

(±)8(9)-EET ethanolamide is a cytochrome P450 (CYP450) metabolite of arachidonoyl ethanolamide (AEA), although specific stereochemistry rather than a racemic mixture would likely ensue from enzymatic metabolism (PMID: 17272674 ). AEA is an endogenous lipid neurotransmitter with cannabingeric activity, binding to both the central cannabinoid (CB1) and peripheral cannabinoid (CB2) receptors (PMID: 8395053 , 16078824 ). Fatty acid amide hydrolase (FAAH) is the enzyme responsible for the hydrolysis and inactivation of AEA (PMID: 12052036 ). Metabolism of AEA by COX-2, lipoxygenases, and CYP450 enzymes has also been documented (PMID: 12052037 , 17272674 ). Human liver microsomes metabolize AEA to 5,6-, 8,9-, 11,12-, and 14,15-EET ethanolamides in a time and protein concentration dependent manner (PMID: 17272674 ). (±)8(9)-EET reduces glomerular filtration rate through cyclooxygenase dependent preglomerular vasoconstriction (PMID: 1928373 ). The physiological actions of (±)8(9)-EET ethanolamide have not been examined.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
8(9)-EET-ea	ChEBI
8(9)-EpETrE-ea	ChEBI
8,9-EET-ea	ChEBI
N-(8,9-Epoxy-5Z,11Z,14Z-eicosatrienoyl)-ethanolamine	ChEBI
N-(8,9-Epoxy-5Z,11Z,14Z-icosatrienoyl)ethanolamine	ChEBI
(+/-)8(9)-epetre ethanolamide	HMDB

Chemical Formula

C₂₂H₃₇NO₃

Average Molecular Weight

363.5341

Monoisotopic Molecular Weight

363.277344055

IUPAC Name

(5Z)-N-(2-hydroxyethyl)-7-{3-[(2Z,5Z)-undeca-2,5-dien-1-yl]oxiran-2-yl}hept-5-enamide

Traditional Name

8(9)-EpETrE-EA

CAS Registry Number

None

SMILES

CCCCC\C=C/C\C=C/CC1OC1C\C=C/CCCC(=O)NCCO

InChI Identifier

InChI=1S/C22H37NO3/c1-2-3-4-5-6-7-8-9-12-15-20-21(26-20)16-13-10-11-14-17-22(25)23-18-19-24/h6-7,9-10,12-13,20-21,24H,2-5,8,11,14-19H2,1H3,(H,23,25)/b7-6-,12-9-,13-10-

InChI Key

BXHPMUQFGGSDAK-TYAUOURKSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acylethanolamines. N-acylethanolamines are compounds containing an N-acyethanolamine moiety, which is characterized by an acyl group is linked to the nitrogen atom of ethanolamine.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Amines

Direct Parent

N-acylethanolamines

Alternative Parents

Substituents

N-acylethanolamine
Fatty amide
N-acyl-amine
Fatty acyl
Carboxamide group
Secondary carboxylic acid amide
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Organopnictogen compound
Alcohol
Organic oxygen compound
Organooxygen compound
Primary alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxide
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

N-acyl ethanolamines (endocannabinoids) (LMFA08040033 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Source

Endogenous

Endogenous (HMDB: HMDB0013659)

Exogenous

Food

Food (HMDB: HMDB0013659)

Exogenous (HMDB: HMDB0013659)

Process

Naturally occurring process

Biological process

Cellular process

Cell signaling (HMDB: HMDB0013659)

Role

Biological role

Energy source (HMDB: HMDB0013659)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0013659)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.00085 g/L	ALOGPS
logP	5.42	ALOGPS
logP	4.38	ChemAxon
logS	-5.6	ALOGPS
pKa (Strongest Acidic)	15.33	ChemAxon
pKa (Strongest Basic)	-0.34	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	61.86 Å²	ChemAxon
Rotatable Bond Count	16	ChemAxon
Refractivity	111.37 m³·mol⁻¹	ChemAxon
Polarizability	44.21 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0013659

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB029629

KNApSAcK ID

Not Available

Chemspider ID

17220861

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

16061182

PDB ID

Not Available

ChEBI ID

136989

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for (±)8(9)-EET Ethanolamide (CFc000008543)

MOL for CFc000008543 ((±)8(9)-EET Ethanolamide)

3D MOL for CFc000008543 ((±)8(9)-EET Ethanolamide)

3D SDF for CFc000008543 ((±)8(9)-EET Ethanolamide)

3D-SDF for CFc000008543 ((±)8(9)-EET Ethanolamide)

PDB for CFc000008543 ((±)8(9)-EET Ethanolamide)

3D PDB for CFc000008543 ((±)8(9)-EET Ethanolamide)

SMILES for CFc000008543 ((±)8(9)-EET Ethanolamide)

INCHI for CFc000008543 ((±)8(9)-EET Ethanolamide)

Structure for CFc000008543 ((±)8(9)-EET Ethanolamide)

3D Structure for CFc000008543 ((±)8(9)-EET Ethanolamide)