Structure via PubChem · Public domain (PubChem)
glyceryl 2-oleate
Sign in to saveAlso known as 2-monoolein, 2-oleoyl-glycerol, 2-oleoylglycerol (2OG), MG(0:0/18:1(9Z)/0:0), 2-(9Z-octadecenoyl)-glycerol, 2-monooleoylglycerol, 1,3-dihydroxypropan-2-yl oleate, 2-glyceryl monooleate
2-Oleoylglycerol (2OG) is a monoacylglycerol that is found in biologic tissues. Its synthesis is derived from diacylglycerol precursors. It is metabolized to oleic acid and glycerol primarily by the enzyme monoacylglycerol lipase (MAGL). In 2011, 2OG was found to be an endogenous ligand to GPR119. 2OG has been shown to increase glucagon-like peptide-1 (GLP-1) and gastric inhibitory polypeptide (GIP) levels following administration to the small intestine. 2OG has also been discovered to potentiate G protein and not β-arrestin signaling via allosteric binding of the 5-HT2A receptor.
Chemical data
- Formula
- C21H40O4
- Molecular weight
- 356.5 g/mol
- IUPAC name
- 1,3-dihydroxypropan-2-yl (Z)-octadec-9-enoate
- SMILES
- CCCCCCCC/C=C\CCCCCCCC(=O)OC(CO)CO
- InChIKey
- UPWGQKDVAURUGE-KTKRTIGZSA-N
- XLogP
- 6.3
- Polar surface area
- 66.8 Ų
- H-bond donors
- 2
- H-bond acceptors
- 4
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Mass
- 356.29266
Show 5 more facts
- chemical formula
- C₂₁H₄₀O₄
- canonical SMILES
- CCCCCCCCC=CCCCCCCCC(=O)OC(CO)CO
- isomeric SMILES
- CCCCCCCC/C=C\CCCCCCCC(=O)OC(CO)CO
- found in taxon
- Sciadopitys verticillata
- has characteristic
- bitterness
via Wikidata · CC0
~1 min read
Encyclopedic overview
2 sectionsContents
- See also
- References
2-Oleoylglycerol (2OG) is a monoacylglycerol that is found in biologic tissues. Its synthesis is derived from diacylglycerol precursors. It is metabolized to oleic acid and glycerol primarily by the enzyme monoacylglycerol lipase (MAGL). In 2011, 2OG was found to be an endogenous ligand to GPR119. 2OG has been shown to increase glucagon-like peptide-1 (GLP-1) and gastric inhibitory polypeptide (GIP) levels following administration to the small intestine. 2OG has also been discovered to potentiate G protein and not β-arrestin signaling via allosteric binding of the 5-HT2A receptor.
==See also== 2-Arachidonoylglycerol JZL184
Excerpted from Wikipedia’s “glyceryl 2-oleate” article, available under the CC BY-SA 4.0 licence.