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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2009-01-08 17:24:11 UTC
Update Date2018-05-20 10:01:42 UTC
HMDB IDHMDB0011538
Secondary Accession Numbers
  • HMDB11538
Metabolite Identification
Common NameMG(0:0/18:2(9Z,12Z)/0:0)
DescriptionMG(0:0/18:2(9Z,12Z)/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
ValueSource
2-(9Z,12Z-Octadecadienoyl)-glycerolChEBI
2-Glyceryl 9,12-octadecadienoateChEBI
2-MonolinoleinChEBI
2-MonolinoleoylglycerolChEBI
beta-MonolinoleinChEBI
Glyceryl 2-linoleateChEBI
MG (0:0/18:2(N-6)/0:0)ChEBI
2-Glyceryl 9,12-octadecadienoic acidGenerator
b-MonolinoleinGenerator
β-monolinoleinGenerator
Glyceryl 2-linoleic acidGenerator
1-MonoacylglycerideHMDB
1-MonoacylglycerolHMDB
2-(9Z,12Z-Octadecadienoyl)-rac-glycerolHMDB
2-LGHMDB
2-Linoleoyl-glycerolHMDB
b-MonoacylglycerolHMDB
beta-MonoacylglycerolHMDB
MAG(0:0/18:2)HMDB
MAG(0:0/18:2n6)HMDB
MAG(0:0/18:2W6)HMDB
MAG(18:2)HMDB
MG(0:0/18:2)HMDB
MG(0:0/18:2n6)HMDB
MG(0:0/18:2W6)HMDB
MG(18:2)HMDB
2-lino-GLMeSH
2-LinoleoylglycerolMeSH
Chemical FormulaC21H38O4
Average Molecular Weight354.524
Monoisotopic Molecular Weight354.277009704
IUPAC Name1,3-dihydroxypropan-2-yl (9Z,12Z)-octadeca-9,12-dienoate
Traditional Name1,3-dihydroxypropan-2-yl (9Z,12Z)-octadeca-9,12-dienoate
CAS Registry NumberNot Available
SMILES
[H]C(CO)(CO)OC(=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)25-20(18-22)19-23/h6-7,9-10,20,22-23H,2-5,8,11-19H2,1H3/b7-6-,10-9-
InChI KeyIEPGNWMPIFDNSD-HZJYTTRNSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassLineolic acids and derivatives
Direct ParentLineolic acids and derivatives
Alternative Parents
Substituents
  • Octadecanoid
  • 2-acyl-sn-glycerol
  • Monoacylglycerol
  • Monoradylglycerol
  • Fatty acid ester
  • Glycerolipid
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Primary alcohol
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

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 Solubility0.0024 g/LALOGPS
logP5.55ALOGPS
logP5.25ChemAxon
logS-5.2ALOGPS
pKa (Strongest Acidic)14.28ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count18ChemAxon
Refractivity105.54 m³·mol⁻¹ChemAxon
Polarizability43.45 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0uy0-6590100000-00de715d6951ec184481View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0009000000-89dbc87ac8de09803926View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ur0-0009000000-42f80df81b12ec238f16View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ur2-0049000000-22dec03de7dde1460134View in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Feces
Tissue Locations
  • All Tissues
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified146 +/- 97 uMAdult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal cancer
details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  2. Wang X, Wang J, Rao B, Deng L: Gut flora profiling and fecal metabolite composition of colorectal cancer patients and healthy individuals. Exp Ther Med. 2017 Jun;13(6):2848-2854. doi: 10.3892/etm.2017.4367. Epub 2017 Apr 20. [PubMed:28587349 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB028252
KNApSAcK IDNot Available
Chemspider ID4517636
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5365676
PDB IDNot Available
ChEBI ID75457
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Enzymes

General function:
Lipid transport and metabolism
Specific function:
Converts monoacylglycerides to free fatty acids and glycerol. Hydrolyzes the endocannabinoid 2-arachidonoylglycerol, and thereby contributes to the regulation of endocannabinoid signaling, nociperception and perception of pain (By similarity). Regulates the levels of fatty acids that serve as signaling molecules and promote cancer cell migration, invasion and tumor growth.
Gene Name:
MGLL
Uniprot ID:
Q99685
Molecular weight:
Not Available
General function:
Involved in hydrolase activity
Specific function:
In adipose tissue and heart, it primarily hydrolyzes stored triglycerides to free fatty acids, while in steroidogenic tissues, it principally converts cholesteryl esters to free cholesterol for steroid hormone production.
Gene Name:
LIPE
Uniprot ID:
Q05469
Molecular weight:
116596.715
General function:
Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:
Catalyzes the formation of diacylglycerol from 2-monoacylglycerol and fatty acyl-CoA. Has a preference toward monoacylglycerols containing unsaturated fatty acids in an order of C18:3 > C18:2 > C18:1 > C18:0. Plays a central role in absorption of dietary fat in the small intestine by catalyzing the resynthesis of triacylglycerol in enterocytes. May play a role in diet-induced obesity.
Gene Name:
MOGAT2
Uniprot ID:
Q3SYC2
Molecular weight:
38195.285
General function:
Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:
Catalyzes the formation of diacylglycerol from 2-monoacylglycerol and fatty acyl-CoA. Probably not involved in absorption of dietary fat in the small intestine (By similarity).
Gene Name:
MOGAT1
Uniprot ID:
Q96PD6
Molecular weight:
38812.19
General function:
Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:
Catalyzes the formation of diacylglycerol from 2-monoacylglycerol and fatty acyl-CoA. Also able to catalyze the terminal step in triacylglycerol synthesis by using diacylglycerol and fatty acyl-CoA as substrates. Has a preference toward palmitoyl-CoA and oleoyl-CoA. May be involved in absorption of dietary fat in the small intestine by catalyzing the resynthesis of triacylglycerol in enterocytes.
Gene Name:
MOGAT3
Uniprot ID:
Q86VF5
Molecular weight:
38729.84
General function:
Involved in acid phosphatase activity
Specific function:
Hydrolyzes lysophosphatidic acid to monoacylglycerol.
Gene Name:
ACP6
Uniprot ID:
Q9NPH0
Molecular weight:
48853.955
General function:
Involved in NAD+ kinase activity
Specific function:
Lipid kinase that can phosphorylate both monoacylglycerol and diacylglycerol to form lysophosphatidic acid (LPA) and phosphatidic acid (PA), respectively. Does not phosphorylate sphingosine. Overexpression increases the formation and secretion of LPA, resulting in transactivation of EGFR and activation of the downstream MAPK signaling pathway, leading to increased cell growth
Gene Name:
AGK
Uniprot ID:
Q53H12
Molecular weight:
47136.8
General function:
Involved in catalytic activity
Specific function:
Choline-specific glycerophosphodiester phosphodiesterase. The preferred substrate may be lysosphingomyelin (By similarity). Hydrolyzes lysophosphatidylcholine (LPC) to form monoacylglycerol and phosphorylcholine but not lysophosphatidic acid, showing it has a lysophospholipase C activity. Has a preference for LPC with short (12:0 and 14:0) or polyunsaturated (18:2 and 20:4) fatty acids. Also hydrolyzes glycerophosphorylcholine and sphingosylphosphorylcholine efficiently. Hydrolyzes the classical substrate for phospholipase C, p-nitrophenyl phosphorylcholine in vitro, while it does not hydrolyze the classical nucleotide phosphodiesterase substrate, p-nitrophenyl thymidine 5'-monophosphate. Does not hydrolyze diacyl phospholipids such as phosphatidylethanolamine, phosphatidylinositol, phosphatidylserine, phosphatidylglycerol and phosphatidic acid.
Gene Name:
ENPP6
Uniprot ID:
Q6UWR7
Molecular weight:
50240.625