ChemFOnt: Showing chemical card for Eicosapentaenoyl Ethanolamide (CFc000008533)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:55:21 UTC

Chemfont ID

CFc000008533

Molecule Identification

Common Name

Eicosapentaenoyl Ethanolamide

Definition

Eicosapentaenoyl Ethanolamide (EPEA) is an endogenous fatty acid amide. EPEA is metabolized by fatty acid amide hydrolase (FAAH) and N-acylethanolamine-hydrolyzing acid amidase (NAAA), the latter of which has more specificity toward PEA over other fatty acid amides. DHEA and eicosapentaenoyl ethanolamide (EPEA) bind to the CB1 receptor in rat brains.23 DHA levels in the mouse brain have been shown to inversely affect the levels of 2AG.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(5Z,8Z,11Z,14Z,17Z)-Eicosapentaenoyl ethanolamide	ChEBI
(5Z,8Z,11Z,14Z,17Z-Eicosapentaenoyl) ethanolamine	ChEBI
all-cis-Eicosa-5,8,11,14,17-pentaenoyl ethanolamide	ChEBI
all-cis-Icosa-5,8,11,14,17-pentaenoyl ethanolamide	ChEBI
Anandamide (20:5, N-3)	ChEBI
EPEA	ChEBI
Icosapentaenoyl ethanolamide	ChEBI
N-(5Z,8Z,11Z,14Z,17Z-Eicosapentaenoyl)ethanolamine	ChEBI
N-cis-5,8, 11,14,17-Eicosapentaenoylethanolamine	ChEBI
(5Z,8Z,11Z,14Z,17Z)-Icosapentaenoyl ethanolamide	ChEBI, HMDB
Eicosapentaenoyl ethanolamide	ChEBI
N-(2-Hydroxyethyl)-5Z,8Z,11Z,14Z,17Z-eicosapentaenamide	HMDB
N-(5Z,8Z,11Z,14Z,17Z-Eicosapentaenoyl)-ethanolamine	HMDB

Chemical Formula

C₂₂H₃₅NO₂

Average Molecular Weight

345.5188

Monoisotopic Molecular Weight

345.266779369

IUPAC Name

(5Z,8Z,11Z,14Z,17Z)-N-(2-hydroxyethyl)icosa-5,8,11,14,17-pentaenamide

Traditional Name

(5Z,8Z,11Z,14Z,17Z)-N-(2-hydroxyethyl)icosa-5,8,11,14,17-pentaenamide

CAS Registry Number

109001-03-8

SMILES

CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)NCCO

InChI Identifier

InChI=1S/C22H35NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-22(25)23-20-21-24/h3-4,6-7,9-10,12-13,15-16,24H,2,5,8,11,14,17-21H2,1H3,(H,23,25)/b4-3-,7-6-,10-9-,13-12-,16-15-

InChI Key

OVKKNJPJQKTXIT-JLNKQSITSA-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
Carboxylic acid derivative
Alcohol
Organooxygen compound
Primary alcohol
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

N-(polyunsaturated fatty acyl)ethanolamine (CHEBI:71467 )
N-(long-chain-acyl)ethanolamine (CHEBI:71467 )
endocannabinoid (CHEBI:71467 )
N-acyl ethanolamines (endocannabinoids) (LMFA08040008 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Source

Endogenous

Endogenous (HMDB: HMDB0013649)

Exogenous

Food

Food (HMDB: HMDB0013649)

Exogenous (HMDB: HMDB0013649)

Process

Naturally occurring process

Biological process

Cellular process

Cell signaling (HMDB: HMDB0013649)

Role

Biological role

Energy source (HMDB: HMDB0013649)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0013649)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.0011 g/L	ALOGPS
logP	5.78	ALOGPS
logP	4.95	ChemAxon
logS	-5.5	ALOGPS
pKa (Strongest Acidic)	15.44	ChemAxon
pKa (Strongest Basic)	-0.34	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	49.33 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	114.08 m³·mol⁻¹	ChemAxon
Polarizability	41.74 Å³	ChemAxon
Number of Rings	0	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

HMDB0013649

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB029619

KNApSAcK ID

Not Available

Chemspider ID

4446570

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5283450

PDB ID

Not Available

ChEBI ID

71467

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Eicosapentaenoyl Ethanolamide (CFc000008533)

MOL for CFc000008533 (Eicosapentaenoyl Ethanolamide)

3D MOL for CFc000008533 (Eicosapentaenoyl Ethanolamide)

3D SDF for CFc000008533 (Eicosapentaenoyl Ethanolamide)

3D-SDF for CFc000008533 (Eicosapentaenoyl Ethanolamide)

PDB for CFc000008533 (Eicosapentaenoyl Ethanolamide)

3D PDB for CFc000008533 (Eicosapentaenoyl Ethanolamide)

SMILES for CFc000008533 (Eicosapentaenoyl Ethanolamide)

INCHI for CFc000008533 (Eicosapentaenoyl Ethanolamide)

Structure for CFc000008533 (Eicosapentaenoyl Ethanolamide)

3D Structure for CFc000008533 (Eicosapentaenoyl Ethanolamide)