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Human Metabolome Database Version 3.5

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Showing metabocard for MG(0:0/20:3(11Z,14Z,17Z)/0:0) (HMDB11545)

Record Information
Version 3.5
Creation Date 2009-01-08 10:24:20 -0700
Update Date 2013-02-08 17:26:48 -0700
HMDB ID HMDB11545
Secondary Accession Numbers None
Metabolite Identification
Common Name MG(0:0/20:3(11Z,14Z,17Z)/0:0)
Description MG(0:0/20:3(11Z,14Z,17Z)/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
    Chemical Formula C23H40O4
    Average Molecular Weight 380.5613
    Monoisotopic Molecular Weight 380.292659768
    IUPAC Name 1,3-dihydroxypropan-2-yl (11Z,14Z,17Z)-icosa-11,14,17-trienoate
    Traditional IUPAC Name 1,3-dihydroxypropan-2-yl (11Z,14Z,17Z)-icosa-11,14,17-trienoate
    CAS Registry Number Not Available
    SMILES [H]C(CO)(CO)OC(=O)CCCCCCCCC\C=C/C\C=C/C\C=C/CC
    InChI Identifier InChI=1S/C23H40O4/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/h3-4,6-7,9-10,22,24-25H,2,5,8,11-21H2,1H3/b4-3-,7-6-,10-9-
    InChI Key SLRKCKOWXHZSDR-PDBXOOCHSA-N
    Chemical Taxonomy
    Kingdom Organic Compounds
    Super Class Lipids
    Class Fatty Amides
    Sub Class Endocannabinoids
    Other Descriptors
    • Aliphatic Acyclic Compounds
    • Other Hydroxyeicosapolyenoic Acids
    Substituents
    • Acyclic Alkene
    • Carboxylic Acid Ester
    • Fatty Acid Ester
    • Monoacyl Sn Glycerol
    • Primary Alcohol
    • Saccharide
    • Triose Monosaccharide
    Direct Parent Endocannabinoids
    Ontology
    Status Expected and Not 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 7.890E-04 g/L ALOGPS
    LogP 5.89 ALOGPS
    LogP 5.77 ChemAxon
    LogS -5.68 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 115.86 ChemAxon
    Polarizability 46.81 ChemAxon
    Formal Charge 0 ChemAxon
    Physiological Charge 0 ChemAxon
    Spectra
    Not Available
    Biological Properties
    Cellular Locations
    • Extracellular
    • Membrane
    Biofluid Locations Not Available
    Tissue Location
    • All Tissues
    Pathways Not Available
    Normal Concentrations
    Not Available
    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 FDB028259
    KNApSAcK ID Not Available
    Chemspider ID 24765774 Link_out
    KEGG Compound ID Not Available
    BioCyc ID Not Available
    BiGG ID Not Available
    Wikipedia Link Not Available
    NuGOwiki Link HMDB11545 Link_out
    Metagene Link HMDB11545 Link_out
    METLIN ID Not Available
    PubChem Compound 53480965 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:
    • 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