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Showing metabocard for MG(18:2(9Z,12Z)/0:0/0:0) (HMDB11568)

Record Information
Version 3.5
Creation Date 2009-01-08 10:24:47 -0700
Update Date 2013-02-08 17:26:52 -0700
HMDB ID HMDB11568
Secondary Accession Numbers None
Metabolite Identification
Common Name MG(18:2(9Z,12Z)/0:0/0:0)
Description MG(18:2(9Z,12Z)/0:0/0:0) 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 | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 1-(9Z,12Z-Octadecadienoyl)-rac-glycerol
  2. 1-LG
  3. 1-Linoleoyl-glycerol
  4. 1-Monoacylglyceride
  5. 1-Monoacylglycerol
  6. a-Monoacylglycerol
  7. alpha-Monoacylglycerol
  8. MAG(18:2)
  9. MAG(18:2/0:0)
  10. MAG(18:2n6/0:0)
  11. MAG(18:2w6/0:0)
  12. MG(18:2)
  13. MG(18:2/0:0)
  14. MG(18:2n6/0:0)
  15. MG(18:2w6/0:0)
Chemical Formula C21H38O4
Average Molecular Weight 354.524
Monoisotopic Molecular Weight 354.277009704
IUPAC Name (2S)-2,3-dihydroxypropyl (9Z,12Z)-octadeca-9,12-dienoate
Traditional IUPAC Name (2S)-2,3-dihydroxypropyl (9Z,12Z)-octadeca-9,12-dienoate
CAS Registry Number Not Available
SMILES [H][C@](O)(CO)COC(=O)CCCCCCC\C=C/C\C=C/CCCCC
InChI Identifier InChI=1S/C21H38O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21(24)25-19-20(23)18-22/h6-7,9-10,20,22-23H,2-5,8,11-19H2,1H3/b7-6-,10-9-/t20-/m0/s1
InChI Key WECGLUPZRHILCT-GSNKCQISSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Lineolic Acids and Derivatives
Sub Class N/A
Other Descriptors
  • Aliphatic Acyclic Compounds
Substituents
  • 1,2 Diol
  • Acyclic Alkene
  • Carboxylic Acid Ester
  • Fatty Acid Ester
  • Monoacyl Sn Glycerol
  • Primary Alcohol
  • Saccharide
  • Secondary Alcohol
  • Triose Monosaccharide
Direct Parent Lineolic Acids and Derivatives
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 0.0026 g/L ALOGPS
LogP 5.56 ALOGPS
LogP 5.25 ChemAxon
LogS -5.13 ALOGPS
pKa (strongest acidic) 13.62 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 18 ChemAxon
Refractivity 105.54 ChemAxon
Polarizability 43.43 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 Comments
Blood Detected and Quantified
Article_icon
37.6 +/- 36 uM Adult (>18 years old) Not Specified Normal Pennington Plasma (n=70)
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB028281
KNApSAcK ID Not Available
Chemspider ID 4941255 Link_out
KEGG Compound ID Not Available
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB11568 Link_out
Metagene Link HMDB11568 Link_out
METLIN ID Not Available
PubChem Compound 6436630 Link_out
PDB ID Not Available
ChEBI ID 416096 Link_out
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References Not Available
Enzymes
Name: Monoglyceride lipase
Reactions:
  • Hydrolyses glycerol monoesters of long-chain fatty acids ALL_REAC (other) R01351 R01352 REFERENCE 1 [PMID:6776896] AUTHORS Mentlein R, Heiland S, Heymann E. TITLE Simultaneous purification and comparative characterization of six serine hydrolases from rat liver microsomes. JOURNAL Arch. Biochem. Biophys. 200 (1980) 547-59. ORGANISM Rattus norvegicus [GN:rno] REFERENCE 2 [PMID:5916497] AUTHORS Pope JL, McPherson JC, Tidwell HC. TITLE A study of a monoglyceride-hydrolyzing enzyme of intestinal mucosa. JOURNAL J. Biol. Chem. 241 (1966) 2306-10. ORGANISM Rattus norvegicus [GN:rno]
Gene Name: MGLL
Uniprot ID: Q99685 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Hormone-sensitive lipase
Reactions:
  • (1) diacylglycerol + H2O = monoacylglycerol + a carboxylate [RN:R05209]
  • (2) triacylglycerol + H2O = diacylglycerol + a carboxylate [RN:R01369]
  • (3) monoacylglycerol + H2O = glycerol + a carboxylate [RN:R07293]
Gene Name: LIPE
Uniprot ID: Q05469 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 2-acylglycerol O-acyltransferase 2
Reactions:
  • acyl-CoA + 2-acylglycerol = CoA + diacylglycerol [RN:R01368]
Gene Name: MOGAT2
Uniprot ID: Q3SYC2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 2-acylglycerol O-acyltransferase 1
Reactions:
  • acyl-CoA + 2-acylglycerol = CoA + diacylglycerol [RN:R01368]
Gene Name: MOGAT1
Uniprot ID: Q96PD6 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 2-acylglycerol O-acyltransferase 3
Reactions:
  • acyl-CoA + 2-acylglycerol = CoA + diacylglycerol [RN:R01368]
Gene Name: MOGAT3
Uniprot ID: Q86VF5 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Lysophosphatidic acid phosphatase type 6
Reactions:
  • a phosphate monoester + H2O = an alcohol + phosphate [RN:R00626]
Gene Name: ACP6
Uniprot ID: Q9NPH0 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Acylglycerol kinase, mitochondrial
Reactions:
  • ATP + 1,2-diacyl-sn-glycerol = ADP + 1,2-diacyl-sn-glycerol 3-phosphate [RN:R02240]
Gene Name: AGK
Uniprot ID: Q53H12 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Ectonucleotide pyrophosphatase/phosphodiesterase family member 6
Reactions:
    Gene Name: ENPP6
    Uniprot ID: Q6UWR7 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA