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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2009-01-08 17:24:50 UTC
Update Date2022-11-30 19:04:01 UTC
HMDB IDHMDB0011571
Secondary Accession Numbers
  • HMDB11571
Metabolite Identification
Common NameMG(18:4(6Z,9Z,12Z,15Z)/0:0/0:0)
DescriptionMG(18:4(6Z,9Z,12Z,15Z)/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
Data?1582752923
Synonyms
ValueSource
GlycerolipidHMDB
1-(6Z,9Z,12Z,15Z-Octadecatetraenoyl)-sn-glycerolHMDB
Glycerolipid(18:4(6Z,9Z,12Z,15Z)/0:0/0:0)HMDB
MG(18:4/0:0/0:0)HMDB
MAG(18:4/0:0/0:0)HMDB
(2S)-2,3-Dihydroxypropyl (6Z,9Z,12Z,15Z)-octadeca-6,9,12,15-tetraenoic acidHMDB
Chemical FormulaC21H34O4
Average Molecular Weight350.4923
Monoisotopic Molecular Weight350.245709576
IUPAC Name(2S)-2,3-dihydroxypropyl (6Z,9Z,12Z,15Z)-octadeca-6,9,12,15-tetraenoate
Traditional Name(2S)-2,3-dihydroxypropyl (6Z,9Z,12Z,15Z)-octadeca-6,9,12,15-tetraenoate
CAS Registry NumberNot Available
SMILES
[H][C@](O)(CO)COC(=O)CCCC\C=C/C\C=C/C\C=C/C\C=C/CC
InChI Identifier
InChI=1S/C21H34O4/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/h3-4,6-7,9-10,12-13,20,22-23H,2,5,8,11,14-19H2,1H3/b4-3-,7-6-,10-9-,13-12-/t20-/m0/s1
InChI KeyYICVZGXPPMTJCG-LIYQNMAISA-N
Chemical Taxonomy
Description 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
  • 1-acyl-sn-glycerol
  • Monoradylglycerol
  • Monoacylglycerol
  • Fatty acid ester
  • Glycerolipid
  • 1,2-diol
  • Carboxylic acid ester
  • Secondary alcohol
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Organooxygen compound
  • Primary alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.006 g/LALOGPS
logP4.93ALOGPS
logP4.52ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)13.62ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count16ChemAxon
Refractivity107.78 m³·mol⁻¹ChemAxon
Polarizability40.85 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+195.0431661259
DarkChem[M-H]-191.10431661259
DeepCCS[M+H]+179.90630932474
DeepCCS[M-H]-177.54830932474
DeepCCS[M-2H]-211.75230932474
DeepCCS[M+Na]+186.81930932474
AllCCS[M+H]+192.732859911
AllCCS[M+H-H2O]+190.132859911
AllCCS[M+NH4]+195.132859911
AllCCS[M+Na]+195.832859911
AllCCS[M-H]-189.632859911
AllCCS[M+Na-2H]-191.632859911
AllCCS[M+HCOO]-193.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
MG(18:4(6Z,9Z,12Z,15Z)/0:0/0:0)[H][C@](O)(CO)COC(=O)CCCC\C=C/C\C=C/C\C=C/C\C=C/CC3296.7Standard polar33892256
MG(18:4(6Z,9Z,12Z,15Z)/0:0/0:0)[H][C@](O)(CO)COC(=O)CCCC\C=C/C\C=C/C\C=C/C\C=C/CC2390.6Standard non polar33892256
MG(18:4(6Z,9Z,12Z,15Z)/0:0/0:0)[H][C@](O)(CO)COC(=O)CCCC\C=C/C\C=C/C\C=C/C\C=C/CC2722.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
MG(18:4(6Z,9Z,12Z,15Z)/0:0/0:0),1TMS,isomer #1CC/C=C\C/C=C\C/C=C\C/C=C\CCCCC(=O)OC[C@H](CO)O[Si](C)(C)C2697.9Semi standard non polar33892256
MG(18:4(6Z,9Z,12Z,15Z)/0:0/0:0),1TMS,isomer #2CC/C=C\C/C=C\C/C=C\C/C=C\CCCCC(=O)OC[C@@H](O)CO[Si](C)(C)C2734.5Semi standard non polar33892256
MG(18:4(6Z,9Z,12Z,15Z)/0:0/0:0),2TMS,isomer #1CC/C=C\C/C=C\C/C=C\C/C=C\CCCCC(=O)OC[C@H](CO[Si](C)(C)C)O[Si](C)(C)C2769.8Semi standard non polar33892256
MG(18:4(6Z,9Z,12Z,15Z)/0:0/0:0),1TBDMS,isomer #1CC/C=C\C/C=C\C/C=C\C/C=C\CCCCC(=O)OC[C@H](CO)O[Si](C)(C)C(C)(C)C2932.1Semi standard non polar33892256
MG(18:4(6Z,9Z,12Z,15Z)/0:0/0:0),1TBDMS,isomer #2CC/C=C\C/C=C\C/C=C\C/C=C\CCCCC(=O)OC[C@@H](O)CO[Si](C)(C)C(C)(C)C2966.9Semi standard non polar33892256
MG(18:4(6Z,9Z,12Z,15Z)/0:0/0:0),2TBDMS,isomer #1CC/C=C\C/C=C\C/C=C\C/C=C\CCCCC(=O)OC[C@H](CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3246.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - MG(18:4(6Z,9Z,12Z,15Z)/0:0/0:0) GC-MS (2 TMS) - 70eV, Positivesplash10-0kei-7592500000-4252a8da35b4c93ba6482017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - MG(18:4(6Z,9Z,12Z,15Z)/0:0/0:0) GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - MG(18:4(6Z,9Z,12Z,15Z)/0:0/0:0) 10V, Positive-QTOFsplash10-014i-0009000000-71219e4cc0cdbe01e1a22017-10-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - MG(18:4(6Z,9Z,12Z,15Z)/0:0/0:0) 20V, Positive-QTOFsplash10-014i-0009000000-71219e4cc0cdbe01e1a22017-10-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - MG(18:4(6Z,9Z,12Z,15Z)/0:0/0:0) 40V, Positive-QTOFsplash10-15si-0069000000-dafcf0c9085c759b8b212017-10-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - MG(18:4(6Z,9Z,12Z,15Z)/0:0/0:0) 10V, Negative-QTOFsplash10-000t-1059000000-89719f03abaadb106d2c2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - MG(18:4(6Z,9Z,12Z,15Z)/0:0/0:0) 20V, Negative-QTOFsplash10-0a4i-8091000000-00119fad35f0109ca1082021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - MG(18:4(6Z,9Z,12Z,15Z)/0:0/0:0) 40V, Negative-QTOFsplash10-0a4i-9370000000-110abeb02651577d23882021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - MG(18:4(6Z,9Z,12Z,15Z)/0:0/0:0) 10V, Positive-QTOFsplash10-0a4i-0009000000-07adcb6261e6124d00e92021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - MG(18:4(6Z,9Z,12Z,15Z)/0:0/0:0) 20V, Positive-QTOFsplash10-0a4i-0009000000-07adcb6261e6124d00e92021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - MG(18:4(6Z,9Z,12Z,15Z)/0:0/0:0) 40V, Positive-QTOFsplash10-052b-9005000000-9d71c244da31ac7bc1b62021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - MG(18:4(6Z,9Z,12Z,15Z)/0:0/0:0) 10V, Positive-QTOFsplash10-014i-0009000000-2b07f79aca3f56d8f2a62021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - MG(18:4(6Z,9Z,12Z,15Z)/0:0/0:0) 20V, Positive-QTOFsplash10-014i-0009000000-2b07f79aca3f56d8f2a62021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - MG(18:4(6Z,9Z,12Z,15Z)/0:0/0:0) 40V, Positive-QTOFsplash10-0pf0-0089000000-52b2a86bfb8033165bca2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - MG(18:4(6Z,9Z,12Z,15Z)/0:0/0:0) 10V, Positive-QTOFsplash10-0zgi-2289000000-19946fd0bf07395fc2ab2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - MG(18:4(6Z,9Z,12Z,15Z)/0:0/0:0) 20V, Positive-QTOFsplash10-05q9-9632000000-15acfd10d343c07ddf132021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - MG(18:4(6Z,9Z,12Z,15Z)/0:0/0:0) 40V, Positive-QTOFsplash10-001m-9800000000-aeabc8fdae45822410442021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Feces
Tissue Locations
  • All Tissues
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. 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
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53480980
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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