ChemFOnt: Showing chemical card for Dihomo-gamma-linolenoylethanolamide (CFc000008516)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:55:20 UTC

Chemfont ID

CFc000008516

Molecule Identification

Common Name

Dihomo-gamma-linolenoylethanolamide

Definition

Dihomo-gamma-linolenoylethanolamide (DGLEA) is an N-acylethanolamine. N-acylethanolamines (NAEs) constitute a class of lipid compounds naturally present in both animal and plant membranes as constituents of the membrane-bound phospholipid, N-acylphosphatidylethanolamine (NAPE). NAPE is composed of a third fatty acid moiety linked to the amino head group of the commonly occurring membrane phospholipid, phosphatidylethanolamine. NAEs are released from NAPE by phospholipase D-type hydrolases in response to a variety of stimuli. Transient NAE release and accumulation have been attributed to a variety of biological activities, including neurotransmission, membrane protection, and immunomodulation in animals. During abstinence, young adults with a history of alcohol binge drinking had elevated plasma levels of monounsaturated and polyunsaturatedacylethanolamides, specifically oleoylethanolamide (OEA), palmitoleoylethanolamide (POEA), arachidonoylethanolamide (AEA), and dihomo-gamma-linolenoylethanolamide (DGLEA). Changes in these lipids positively correlated with mRNA upregulation of inflammatory markers in peripheral blood mononuclear cells (PBMCs), such as toll-like receptors (TLR4), pro-inflammatory cytokines/chemokines, and cyclooxygenase-2 (PMID: 29178411 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
8,11,14-Eicosatrienoylethanolamide	ChEBI
Anandamide (20.3,N-6)	ChEBI
HGLEA	ChEBI
Homo-gamma-linolenylethanolamide	ChEBI
N-(8Z,11Z,14Z-Eicosatrienoyl)-ethanolamine	ChEBI
N-(8Z,11Z,14Z-Icosatrienoyl)-ethanolamide	ChEBI
Homo-g-linolenylethanolamide	Generator
Homo-γ-linolenylethanolamide	Generator
Dihomo-g-linolenoylethanolamide	Generator
Dihomo-γ-linolenoylethanolamide	Generator
Homo-gamma-linolenoyl ethanolamide	MeSH
dihomo-g-Linolenoyl ethanolamide	Generator, HMDB
dihomo-γ-linolenoyl ethanolamide	Generator, HMDB
(8Z,11Z,14Z)-N-(2-Hydroxyethyl)icosa-8,11,14-trienamide	HMDB
DGLA ea	HMDB
dihomo-gamma-Linolenoylethanol amide	HMDB
Dihomo-g-linolenoyl-ea	Generator
Dihomo-γ-linolenoyl-ea	Generator

Chemical Formula

C₂₂H₃₉NO₂

Average Molecular Weight

349.5506

Monoisotopic Molecular Weight

349.298079497

IUPAC Name

(8Z,11Z,14Z)-N-(2-hydroxyethyl)icosa-8,11,14-trienamide

Traditional Name

hglea

CAS Registry Number

150314-34-4

SMILES

CCCCC\C=C/C\C=C/C\C=C/CCCCCCC(=O)NCCO

InChI Identifier

InChI=1S/C22H39NO2/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/h6-7,9-10,12-13,24H,2-5,8,11,14-21H2,1H3,(H,23,25)/b7-6-,10-9-,13-12-

InChI Key

ULQWKETUACYZLI-QNEBEIHSSA-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:34488 )
N-(long-chain-acyl)ethanolamine (CHEBI:34488 )
N-acyl ethanolamides (endocannabinoids) (C13828 )
N-acyl ethanolamines (endocannabinoids) (LMFA08040011 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21359215)

Cellular substructure

Source

Endogenous

Endogenous (HMDB: HMDB0013625)

Exogenous

Food

Food (HMDB: HMDB0013625)

Exogenous (HMDB: HMDB0013625)

Process

Naturally occurring process

Biological process

Cellular process

Cell signaling (HMDB: HMDB0013625)

Role

Biological role

Energy source (HMDB: HMDB0013625)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0013625)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.00023 g/L	ALOGPS
logP	6.28	ALOGPS
logP	5.68	ChemAxon
logS	-6.2	ALOGPS
pKa (Strongest Acidic)	15.45	ChemAxon
pKa (Strongest Basic)	-1.3	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	17	ChemAxon
Refractivity	111.85 m³·mol⁻¹	ChemAxon
Polarizability	44.39 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0013625

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB029602

KNApSAcK ID

Not Available

Chemspider ID

4445443

KEGG Compound ID

C13828

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5282272

PDB ID

Not Available

ChEBI ID

34488

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Dihomo-gamma-linolenoylethanolamide (CFc000008516)

MOL for CFc000008516 (Dihomo-gamma-linolenoylethanolamide)

3D MOL for CFc000008516 (Dihomo-gamma-linolenoylethanolamide)

3D SDF for CFc000008516 (Dihomo-gamma-linolenoylethanolamide)

3D-SDF for CFc000008516 (Dihomo-gamma-linolenoylethanolamide)

PDB for CFc000008516 (Dihomo-gamma-linolenoylethanolamide)

3D PDB for CFc000008516 (Dihomo-gamma-linolenoylethanolamide)

SMILES for CFc000008516 (Dihomo-gamma-linolenoylethanolamide)

INCHI for CFc000008516 (Dihomo-gamma-linolenoylethanolamide)

Structure for CFc000008516 (Dihomo-gamma-linolenoylethanolamide)

3D Structure for CFc000008516 (Dihomo-gamma-linolenoylethanolamide)