Record Information
Version3.6
Creation Date2009-01-08 17:24:10 UTC
Update Date2013-02-09 00:26:46 UTC
HMDB IDHMDB11537
Secondary Accession NumbersNone
Metabolite Identification
Common NameMG(0:0/18:1(9Z)/0:0)
DescriptionMG(0:0/18:1(9Z)/0:0) is a monoacylglyceride. A monoglyceride, more correctly known as a monoacylglycerol, is a glyceride consisting of one fatty acid chain covalently bonded to a glycerol molecule through an ester linkage. Monoacylglycerol can be broadly divided into two groups; 1-monoacylglycerols (or 3-monoacylglycerols) and 2-monoacylglycerols, depending on the position of the ester bond on the glycerol moiety. Normally the 1-/3-isomers are not distinguished from each other and are termed 'alpha-monoacylglycerols', while the 2-isomers are beta-monoacylglycerols. Monoacylglycerols are formed biochemically via release of a fatty acid from diacylglycerol by diacylglycerol lipase or hormone sensitive lipase. Monoacylglycerols are broken down by monoacylglycerol lipase. They tend to be minor components only of most plant and animal tissues, and indeed would not be expected to accumulate because their strong detergent properties would have a disruptive effect on membranes. 2-Monoacylglycerols are a major end product of the intestinal digestion of dietary fats in animals via the enzyme pancreatic lipase. They are taken up directly by the intestinal cells and converted to triacylglycerols via the monoacylglycerol pathway before being transported in lymph to the liver. Mono- and Diglycerides are commonly added to commercial food products in small quantities. They act as emulsifiers, helping to mix ingredients such as oil and water that would not otherwise blend well.
Structure
Thumb
Synonyms
  1. 1-Monoacylglyceride
  2. 1-Monoacylglycerol
  3. 2-(9Z-Octadecenoyl)-rac-glycerol
  4. 2-OG
  5. 2-Oleoyl-glycerol
  6. b-Monoacylglycerol
  7. beta-Monoacylglycerol
  8. MAG(0:0/18:1)
  9. MAG(0:0/18:1n9)
  10. MAG(0:0/18:1w9)
  11. MAG(18:1)
  12. MG(0:0/18:1)
  13. MG(0:0/18:1n9)
  14. MG(0:0/18:1w9)
  15. MG(18:1)
Chemical FormulaC21H40O4
Average Molecular Weight356.5399
Monoisotopic Molecular Weight356.292659768
IUPAC Name1,3-dihydroxypropan-2-yl (9Z)-octadec-9-enoate
Traditional IUPAC Name1,3-dihydroxypropan-2-yl (9Z)-octadec-9-enoate
CAS Registry NumberNot Available
SMILES
[H]C(CO)(CO)OC(=O)CCCCCCC\C=C/CCCCCCCC
InChI Identifier
InChI=1S/C21H40O4/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/h9-10,20,22-23H,2-8,11-19H2,1H3/b10-9-
InChI KeyUPWGQKDVAURUGE-KTKRTIGZSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassLipids
ClassGlycerolipids
Sub ClassMonoacylglycerols
Other Descriptors
  • Aliphatic Acyclic Compounds
  • Monoacylglycerols(Lipidmaps)
Substituents
  • Acyclic Alkene
  • Carboxylic Acid Ester
  • Fatty Acid Ester
  • Primary Alcohol
  • Saccharide
  • Triose Monosaccharide
Direct ParentMonoacylglycerols
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Energy source
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane component
  • Membrane integrity/stability
Application
  • Emuslifiers
  • Food additives
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
water solubility0.0017 g/LALOGPS
logP6.25ALOGPS
logP5.61ChemAxon
logS-5.3ALOGPS
pKa (strongest acidic)14.28ChemAxon
pKa (strongest basic)-3ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count3ChemAxon
hydrogen donor count2ChemAxon
polar surface area66.76ChemAxon
rotatable bond count19ChemAxon
refractivity104.43ChemAxon
polarizability44.89ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
Tissue Location
  • All Tissues
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodDetected and Quantified166 +/- 130 uMAdult (>18 years old)Not SpecifiedCommentNormal
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB009514
KNApSAcK IDNot Available
Chemspider ID4478086
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB11537
Metagene LinkHMDB11537
METLIN IDNot Available
PubChem Compound5319879
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Gene Name:
MGLL
Uniprot ID:
Q99685
Gene Name:
LIPE
Uniprot ID:
Q05469
Gene Name:
MOGAT2
Uniprot ID:
Q3SYC2
Gene Name:
MOGAT1
Uniprot ID:
Q96PD6
Gene Name:
MOGAT3
Uniprot ID:
Q86VF5