GLYCERYL 2-LINOLEATE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C21H38O4
Molecular Weight	354.524
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	2
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCCCC\C=C/C\C=C/CCCCCCCC(=O)OC(CO)CO

InChI

InChIKey=IEPGNWMPIFDNSD-HZJYTTRNSA-N

InChI=1S/C21H38O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21(24)25-20(18-22)19-23/h6-7,9-10,20,22-23H,2-5,8,11-19H2,1H3/b7-6-,10-9-

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25762940 | https://www.ncbi.nlm.nih.gov/pubmed/9721036 | https://www.ncbi.nlm.nih.gov/pubmed/27117667 | https://www.ncbi.nlm.nih.gov/pubmed/11011050 | https://www.ncbi.nlm.nih.gov/pubmed/15492019

Glyceryl 2-linoleate is a fatty acid derivative. It inhibits monoacylglycerol lipase and fatty acid amide hydrolase activity. Glyceryl 2-linoleate enhanced a 2-Arachidonoyl-glycerol inhibition of tumor necrosis factor alpha production in murine macrophages when applied with 2-Arachidonoyl-glycerol. Initially, it was found that Glyceryl 2-linoleate potentiated the apparent binding of 2-Arachidonoyl-glycerol to cannabinoid receptors CB1 and CB2. However, later research revealed that in no case do the lipid Glyceryl 2-linoleate acts as entourage compounds for 2-Arachidonoyl-glycerol. Increase in Glyceryl 2-linoleate plasma concentrations was observed in cocaine subjects diagnosed with psychiatric comorbidity.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Monoglyceride lipase 8 Target ID: CHEMBL3321 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15492019	Inhibitor 8297	22.0 µM [IC50]
Anandamide amidohydrolase 26 Target ID: CHEMBL3229 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15492019	Inhibitor 8297	12.0 µM [IC50]
2-Arachidonoyl-glycerol 1 Target ID: 2-Arachidonoyl-glycerol Sources: https://www.ncbi.nlm.nih.gov/pubmed/9721036 \| https://www.ncbi.nlm.nih.gov/pubmed/27117667 \| https://www.ncbi.nlm.nih.gov/pubmed/11011050	Modulator 828

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cocaine addiction with psychiatric comorbidity 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25762940	Diagnostic		Natural Metabolite	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Is the cannabinoid CB1 receptor a 2-arachidonoylglycerol receptor? Structural requirements for triggering a Ca2+ transient in NG108-15 cells.	1997 Oct	9399597
An entourage effect: inactive endogenous fatty acid glycerol esters enhance 2-arachidonoyl-glycerol cannabinoid activity.	1998 Jul 17	9721036
2-Arachidonylglycerol, an endogenous cannabinoid, inhibits tumor necrosis factor-alpha production in murine macrophages, and in mice.	2000 Oct 6	11011050
Critical role of the endogenous cannabinoid system in mouse pup suckling and growth.	2001 May 11	11426843
Inhibition of monoacylglycerol lipase and fatty acid amide hydrolase by analogues of 2-arachidonoylglycerol.	2004 Nov	15492019
Sex differences in psychiatric comorbidity and plasma biomarkers for cocaine addiction in abstinent cocaine-addicted subjects in outpatient settings.	2015	25762940
Where's my entourage? The curious case of 2-oleoylglycerol, 2-linolenoylglycerol, and 2-palmitoylglycerol.	2016 Aug	27117667
Evolution of the diacylglycerol lipases.	2016 Oct	27568643

Patents

Sample Use Guides

In Vivo Use Guide

Mice: 10 mg/kg

Route of Administration: Intraperitoneal

In Vitro Use Guide

In RBL-2H3 cells was found that without the addition of GLYCERYL 2-LINOLEATE, 2-Arachidonoyl-glycerol (2-Ara-Gl) disappeared from the culture media in a temperature-dependent fashion with a half life at 37C of 6 min. 100 uM of GLYCERYL 2-LINOLEATE prevented this loss of 2-Ara-Gl from the medium. An eight-fold increase of 2-Ara-Gl levels was observed after 30 min incubation.

Name

Type

Language

GLYCERYL 2-LINOLEATE

Common Name

English

2-MONOLINOLEIN

Common Name

English

9,12-OCTADECADIENOIC ACID (9Z,12Z)-, 2-HYDROXY-1-(HYDROXYMETHYL)ETHYL ESTER

Common Name

English

9,12-OCTADECADIENOIC ACID (Z,Z)-, 2-HYDROXY-1-(HYDROXYMETHYL)ETHYL ESTER

Common Name

English

2-GLYCERYL 9,12-OCTADECADIENOATE

Common Name

English

LINOLEIN, 2-MONO-

Common Name

English

2-MONOLINOLEOYLGLYCEROL

Systematic Name

English

2-LINOLEOYLGLYCEROL

Systematic Name

English

.BETA.-MONOLINOLEIN

Common Name

English

Code System Code Type Description

MESH

C114955