Structure Database (LMSD)
Common Name
MG(0:0/20:4(5Z,8Z,11Z,14Z)/0:0)
Systematic Name
2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycerol
Synonyms
- 2-Arachidonoylglycerol
- 2-Arachidonylglycerol
- 2-AG
- MG(20:4)
3D model of MG(0:0/20:4(5Z,8Z,11Z,14Z)/0:0)
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Category
Main Class
Sub Class
Biological Context
2-Arachidonoyl glycerol (2-AG) is an endogenous agonist of the cannabinoid (CB) receptors CB1 and CB2 (Kis = 25.3-472 and 145-1,400 nM, respectively).1,2,3 Unlike arachidonoyl ethanolamide (AEA), 2-AG is present at relatively high levels in the central nervous system and is the most abundant molecular species of monoacylglycerol (MAG) found in rat brain.1,4 Formation of 2-AG is calcium-dependent and is mediated by the activities of phospholipase C (PLC) and diacylglycerol (DAG) lipase.1 2-AG acts as a full agonist at the CB1 receptor. At a concentration of 0.3 nM, 2-AG induces a rapid, transient increase in intracellular free calcium in NG108-15 neuroblastoma X glioma cells through a CB1 receptor-dependent mechanism.2 2-AG is metabolized in vitro by MAG lipase and fatty acid amide hydrolase (FAAH), with MAG lipase likely being the principle metabolizing enzyme in vivo.5
This information has been provided by Cayman Chemical
References
2. Sugiura, T., Kodaka, T., Nakane, S., et al. Evidence that the cannabinoid CB1 receptor is a 2-arachidonoylglycerol receptor. Structure-activity relationship of 2-arachidonoylglycerol, ether-linked analogues, and related compounds. The Journal of Biological Chemisty 274(5), 2794-2801 (1999).
3. Stella, N., Schweitzer, P., and Piomelli, D. A second endogenous cannabinoid that modulates long-term potentiation. Nature 388(6644), 773-778 (1997).
4. Pertwee, R.G. Pharmacology of cannabinoid receptor ligands. Curr. Med. Chem. 6(8), 635-664 (1999).
References
String Representations
InChiKey (Click to copy)
RCRCTBLIHCHWDZ-DOFZRALJSA-N
InChi (Click to copy)
InChI=1S/C23H38O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-23(26)27-22(20-24)21-25/h6-7,9-10,12-13,15-16,22,24-25H,2-5,8,11,14,17-21H2,1H3/b7-6-,10-9-,13-12-,16-15-
SMILES (Click to copy)
OC[C@]([H])(OC(CCC/C=C\C/C=C\C/C=C\C/C=C\CCCCC)=O)CO
Other Databases
KEGG ID
HMDB ID
CHEBI ID
PubChem CID
SwissLipids ID
Cayman ID
PDB ID
GuidePharm ID
Calculated Physicochemical Properties
Heavy Atoms
27
Rings
0
Aromatic Rings
0
Rotatable Bonds
18
Van der Waals Molecular Volume
428.42
Topological Polar Surface Area
66.76
Hydrogen Bond Donors
2
Hydrogen Bond Acceptors
4
logP
5.88
Molar Refractivity
113.95
Admin
Created at
-
Updated at
24th Feb 2025
LIPID MAPS® abbreviations for glycerolipids (GL)
The LIPID MAPS® glycerolipid abbreviations (MG,DG,TG) are used here to refer to species with one, two or three radyl side-chains, respectively, where the structures of the side chains are indicated within parentheses in the 'Prefix(sn1/sn2/sn3)' format (e.g. TG(16:0/18:1(9Z)/18:0). Acyl chains are assumed by default. The alkyl ether linkage is represented by the 'O-' prefix, e.g. DG(O-16:0/18:1(9Z)/0:0), whereas the 1Z-alkenyl ether (Plasmalogen) linkage is represented by the 'P-' prefix, e.g. and DG(P-14:0/18:1(9Z)/0:0).
For Diradylglycerols and Triradylglycerols, it is not always possible to experimentally determine the exact position of radyl groups on the glycerol group. For Diradylglycerols with two different radyl groups, two different structural isomers exist. For Triradylglycerols with three different radyl groups, six different isomers exist.
Instead of drawing all possible structural isomers explicitly for Diradylglycerols and Triradylglycerols, the LIPID MAPS® abbreviation scheme supports the isomeric specification. A suffix containing 'iso' along with the number of possible isomers is appended to the abbreviation (e.g. [iso2],[iso6]) and a single unique LM_ID is assigned. The structure assigned to the LM_ID corresponds to the radyl substitution shown in the abbreviation. An option is provided to display the other isomers in the group.
The [rac] designation refers to racemic mixtures due to substitution at the sn1 and sn3 positions of glycerol.
The LIPID MAPS® glycerolipid abbreviations (MG,DG,TG) are used here to refer to species with one, two or three radyl side-chains, respectively, where the structures of the side chains are indicated within parentheses in the 'Prefix(sn1/sn2/sn3)' format (e.g. TG(16:0/18:1(9Z)/18:0). Acyl chains are assumed by default. The alkyl ether linkage is represented by the 'O-' prefix, e.g. DG(O-16:0/18:1(9Z)/0:0), whereas the 1Z-alkenyl ether (Plasmalogen) linkage is represented by the 'P-' prefix, e.g. and DG(P-14:0/18:1(9Z)/0:0).
For Diradylglycerols and Triradylglycerols, it is not always possible to experimentally determine the exact position of radyl groups on the glycerol group. For Diradylglycerols with two different radyl groups, two different structural isomers exist. For Triradylglycerols with three different radyl groups, six different isomers exist.
Instead of drawing all possible structural isomers explicitly for Diradylglycerols and Triradylglycerols, the LIPID MAPS® abbreviation scheme supports the isomeric specification. A suffix containing 'iso' along with the number of possible isomers is appended to the abbreviation (e.g. [iso2],[iso6]) and a single unique LM_ID is assigned. The structure assigned to the LM_ID corresponds to the radyl substitution shown in the abbreviation. An option is provided to display the other isomers in the group.
The [rac] designation refers to racemic mixtures due to substitution at the sn1 and sn3 positions of glycerol.