Showing metabocard for DG(14:0/14:0/0:0) (BMDB0007008)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 23:28:39 UTC
Update Date2020-05-21 16:27:17 UTC
BMDB IDBMDB0007008
Secondary Accession Numbers
  • BMDB07008
Metabolite Identification
Common NameDG(14:0/14:0/0:0)
Description1,2-Dimyristoyl-sn-glycerol, also known as 1,2-dimyristoyl-sn-glycerol or DAG(14:0/14:0), belongs to the class of organic compounds known as 1,2-1,2-dimyristoyl-sn-glycerols. These are 1,2-dimyristoyl-sn-glycerols containing a glycerol acylated at positions 1 and 2. Thus, 1,2-dimyristoyl-sn-glycerol is considered to be a diradylglycerol lipid molecule. 1,2-Dimyristoyl-sn-glycerol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 1,2-Dimyristoyl-sn-glycerol exists in all living organisms, ranging from bacteria to humans. In cattle, 1,2-dimyristoyl-sn-glycerol is involved in the metabolic pathway called de novo triacylglycerol biosynthesis TG(14:0/14:0/14:0) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(S)-1,2-DimyristinChEBI
(S)-Glycerol 1,2-dimyristateChEBI
1,2-Di-O-dimyristoyl-sn-glycerolChEBI
1,2-Dimyristoyl-sn-glycerolChEBI
14:0 DGChEBI
sn-1,2-DimyristinChEBI
sn-1,2-DimyristoylglycerolChEBI
1,2-Ditetradecanoyl-sn-glycerolKegg
(S)-Glycerol 1,2-dimyristic acidGenerator
DG(14:0/14:0)Lipid Annotator, HMDB
Diacylglycerol(28:0)Lipid Annotator, HMDB
Diacylglycerol(14:0/14:0)Lipid Annotator, HMDB
DiglycerideLipid Annotator, HMDB
1,2-dimyristoyl-rac-glycerolLipid Annotator, HMDB
DAG(28:0)Lipid Annotator, HMDB
DiacylglycerolLipid Annotator, HMDB
DG(28:0)Lipid Annotator, HMDB
DG(14:0/14:0/0:0)Lipid Annotator, ChEBI
1,2-ditetradecanoyl-rac-glycerolLipid Annotator, HMDB
DAG(14:0/14:0)Lipid Annotator, HMDB
Dimyristoyl diglycerideMeSH, HMDB
1,2-DimyristoylglycerolMeSH, HMDB
Chemical FormulaC31H60O5
Average Molecular Weight512.8051
Monoisotopic Molecular Weight512.44407503
IUPAC Name(2S)-1-hydroxy-3-(tetradecanoyloxy)propan-2-yl tetradecanoate
Traditional Namediacylglycerol
CAS Registry NumberNot Available
SMILES
[H][C@](CO)(COC(=O)CCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCC
InChI Identifier
InChI=1S/C31H60O5/c1-3-5-7-9-11-13-15-17-19-21-23-25-30(33)35-28-29(27-32)36-31(34)26-24-22-20-18-16-14-12-10-8-6-4-2/h29,32H,3-28H2,1-2H3/t29-/m0/s1
InChI KeyJFBCSFJKETUREV-LJAQVGFWSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 1,2-diacylglycerols. These are diacylglycerols containing a glycerol acylated at positions 1 and 2.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerolipids
Sub ClassDiradylglycerols
Direct Parent1,2-diacylglycerols
Alternative Parents
Substituents
  • 1,2-acyl-sn-glycerol
  • Fatty acid ester
  • Fatty acyl
  • Dicarboxylic acid or derivatives
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP9.19ALOGPS
logP10.22ChemAxon
logS-7.3ALOGPS
pKa (Strongest Acidic)14.58ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area72.83 ŲChemAxon
Rotatable Bond Count30ChemAxon
Refractivity149.29 m³·mol⁻¹ChemAxon
Polarizability66.14 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0pb9-6539660000-520c946560c78391b803View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000090000-02de2f1820f28e136d03View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000j-0090630000-e71d6682bec32596592cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0019-0090170000-8aa23af5db4b0446acbfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000090000-ff38e7d81441a58488e7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000j-0090630000-4d05e0acb1eda67d4637View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0019-0090170000-4d13bc2f0e08f9d7649aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dr-1091250000-06dc656cdb1e35394a07View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dr-4291100000-536476a16f5fed6e55e9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0bt9-9670000000-bd0ec4ad4bd32c052881View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03fr-1073090000-65a525eb2c3a2a98eb36View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-1090000000-9a3feb0bdec4505fbde0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-0190000000-43a00ce8043dd157c2ffView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000090000-be91b9337407bceefc54View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0000090000-be91b9337407bceefc54View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-0019010000-557c8e282a1ff26f7af4View in MoNA
1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cell membrane
  • Membrane
Biospecimen Locations
  • All Tissues
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
All TissuesExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0007008
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB024202
KNApSAcK IDNot Available
Chemspider ID8544614
KEGG Compound IDC16667
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10369168
PDB IDNot Available
ChEBI ID80651
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Ethanolaminephosphotransferase 1
General function:
Involved in ethanolaminephosphotransferase activity
Specific function:
Catalyzes phosphatidylethanolamine biosynthesis from CDP-ethanolamine. It thereby plays a central role in the formation and maintenance of vesicular membranes. Involved in the foramtion of phosphatidylethanolamine via 'Kennedy' pathway (By similarity).
Gene Name:
SELENOI
Uniprot ID:
Q17QM4
Molecular weight:
45214.0
Reactions
CDP-Ethanolamine + DG(14:0/14:0/0:0) → Cytidine monophosphate + PE(14:0/14:0)details
Enzyme Details
2. Diacylglycerol O-acyltransferase 1
General function:
Not Available
Specific function:
Catalyzes the terminal and only committed step in triacylglycerol synthesis by using diacylglycerol and fatty acyl CoA as substrates. In contrast to DGAT2 it is not essential for survival. May be involved in VLDL (very low density lipoprotein) assembly. Functions as the major acyl-CoA retinol acyltransferase (ARAT) in the skin, where it acts to maintain retinoid homeostasis and prevent retinoid toxicity leading to skin and hair disorders. In liver, plays a role in esterifying exogenous fatty acids to glycerol.
Gene Name:
DGAT1
Uniprot ID:
Q8MK44
Molecular weight:
55602.0
Reactions
DG(14:0/14:0/0:0) + Palmityl-CoA → TG(14:0/14:0/16:0) + Coenzyme Adetails
DG(14:0/14:0/0:0) + Stearoyl-CoA → TG(14:0/14:0/18:0) + Coenzyme Adetails
DG(14:0/14:0/0:0) + Oleoyl-CoA → TG(14:0/14:0/18:1(9Z)) + Coenzyme Adetails
DG(14:0/14:0/0:0) + Gamma-linolenoyl-CoA → TG(14:0/14:0/18:3(6Z,9Z,12Z)) + Coenzyme Adetails
DG(14:0/14:0/0:0) + Eicosanoyl-CoA → TG(14:0/14:0/20:0) + Coenzyme Adetails
DG(14:0/14:0/0:0) + Gondoyl-CoA → TG(14:0/14:0/20:1(11Z)) + Coenzyme Adetails
DG(14:0/14:0/0:0) + 5Z,8Z,11Z,14Z-eicosatetraenonyl-CoA → TG(14:0/14:0/20:4(5Z,8Z,11Z,14Z)) + Coenzyme Adetails
DG(14:0/14:0/0:0) + Docosanoyl-CoA → TG(14:0/14:0/22:0) + Coenzyme Adetails
DG(14:0/14:0/0:0) + Erucoyl-CoA → TG(14:0/14:0/22:1(13Z)) + Coenzyme Adetails
DG(14:0/14:0/0:0) + Clupanodonyl CoA → TG(14:0/14:0/22:5(7Z,10Z,13Z,16Z,19Z)) + Coenzyme Adetails
DG(14:0/14:0/0:0) + Tetracosanoyl-CoA → TG(14:0/14:0/24:0) + Coenzyme Adetails