Human Metabolome Database Version 3.5

Showing metabocard for MG(0:0/18:1(9Z)/0:0) (HMDB11537)

Record Information
Version 3.5
Creation Date 2009-01-08 10:24:10 -0700
Update Date 2013-02-08 17:26:46 -0700
HMDB ID HMDB11537
Secondary Accession Numbers None
Metabolite Identification
Common Name MG(0:0/18:1(9Z)/0:0)
Description MG(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
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C21H40O4
Average Molecular Weight 356.5399
Monoisotopic Molecular Weight 356.292659768
IUPAC Name 1,3-dihydroxypropan-2-yl (9Z)-octadec-9-enoate
Traditional IUPAC Name 1,3-dihydroxypropan-2-yl (9Z)-octadec-9-enoate
CAS Registry Number Not 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 Key UPWGQKDVAURUGE-KTKRTIGZSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Glycerolipids
Sub Class Monoacylglycerols
Other Descriptors
  • Aliphatic Acyclic Compounds
  • Monoacylglycerols(Lipidmaps)
Substituents
  • Acyclic Alkene
  • Carboxylic Acid Ester
  • Fatty Acid Ester
  • Primary Alcohol
  • Saccharide
  • Triose Monosaccharide
Direct Parent Monoacylglycerols
Ontology
Status Detected 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
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 0.0017 g/L ALOGPS
LogP 6.25 ALOGPS
LogP 5.61 ChemAxon
LogS -5.33 ALOGPS
pKa (strongest acidic) 14.28 ChemAxon
pKa (strongest basic) -3 ChemAxon
Hydrogen Acceptor Count 3 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 66.76 A2 ChemAxon
Rotatable Bond Count 19 ChemAxon
Refractivity 104.43 ChemAxon
Polarizability 44.89 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
Tissue Location
  • All Tissues
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
166 +/- 130 uM Adult (>18 years old) Not Specified Comment Normal
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB009514
KNApSAcK ID Not Available
Chemspider ID 4478086 Link_out
KEGG Compound ID Not Available
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB11537 Link_out
Metagene Link HMDB11537 Link_out
METLIN ID Not Available
PubChem Compound 5319879 Link_out
PDB ID Not Available
ChEBI ID Not Available
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References Not Available

Enzymes
Name: Monoglyceride lipase
Reactions: Not Available
Gene Name: MGLL
Uniprot ID: Q99685 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Hormone-sensitive lipase
Reactions: Not Available
Gene Name: LIPE
Uniprot ID: Q05469 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 2-acylglycerol O-acyltransferase 2
Reactions: Not Available
Gene Name: MOGAT2
Uniprot ID: Q3SYC2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 2-acylglycerol O-acyltransferase 1
Reactions: Not Available
Gene Name: MOGAT1
Uniprot ID: Q96PD6 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 2-acylglycerol O-acyltransferase 3
Reactions: Not Available
Gene Name: MOGAT3
Uniprot ID: Q86VF5 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Lysophosphatidic acid phosphatase type 6
Reactions: Not Available
Gene Name: ACP6
Uniprot ID: Q9NPH0 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Acylglycerol kinase, mitochondrial
Reactions: Not Available
Gene Name: AGK
Uniprot ID: Q53H12 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Ectonucleotide pyrophosphatase/phosphodiesterase family member 6
Reactions: Not Available
Gene Name: ENPP6
Uniprot ID: Q6UWR7 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA