Showing metabocard for DG(14:0/20:4(8Z,11Z,14Z,17Z)/0:0) (BMDB0007026)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 23:29:01 UTC
Update Date2020-05-21 16:27:23 UTC
BMDB IDBMDB0007026
Secondary Accession Numbers
  • BMDB07026
Metabolite Identification
Common NameDG(14:0/20:4(8Z,11Z,14Z,17Z)/0:0)
DescriptionDG(14:0/20:4(8Z,11Z,14Z,17Z)/0:0), also known as dg(14:0/20:4(8z,11z,14z,17z)/0:0) or DG(14:0/20:4), belongs to the class of organic compounds known as 1,2-dg(14:0/20:4(8z,11z,14z,17z)/0:0)s. These are dg(14:0/20:4(8z,11z,14z,17z)/0:0)s containing a glycerol acylated at positions 1 and 2. DG(14:0/20:4(8Z,11Z,14Z,17Z)/0:0) is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). DG(14:0/20:4(8Z,11Z,14Z,17Z)/0:0) participates in a number of enzymatic reactions, within cattle. In particular, DG(14:0/20:4(8Z,11Z,14Z,17Z)/0:0) can be biosynthesized from PA(14:0/20:4(8Z,11Z,14Z,17Z)) through its interaction with the enzyme phosphatidate phosphatase. Furthermore, DG(14:0/20:4(8Z,11Z,14Z,17Z)/0:0) and adrenoyl-CoA can be converted into TG(14:0/20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z)) through the action of the enzyme dg(14:0/20:4(8z,11z,14z,17z)/0:0) O-acyltransferase. Furthermore, DG(14:0/20:4(8Z,11Z,14Z,17Z)/0:0) can be biosynthesized from PA(14:0/20:4(8Z,11Z,14Z,17Z)) through the action of the enzyme phosphatidate phosphatase. Furthermore, DG(14:0/20:4(8Z,11Z,14Z,17Z)/0:0) and nervonoyl-CoA can be converted into TG(14:0/20:4(8Z,11Z,14Z,17Z)/24:1(15Z)); which is catalyzed by the enzyme dg(14:0/20:4(8z,11z,14z,17z)/0:0) O-acyltransferase. Finally, CDP-Ethanolamine and DG(14:0/20:4(8Z,11Z,14Z,17Z)/0:0) can be converted into cytidine monophosphate and PE(14:0/20:4(8Z,11Z,14Z,17Z)) through its interaction with the enzyme choline/ethanolaminephosphotransferase. In cattle, DG(14:0/20:4(8Z,11Z,14Z,17Z)/0:0) is involved in a few metabolic pathways, which include de novo triacylglycerol biosynthesis TG(14:0/20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z)) pathway, de novo triacylglycerol biosynthesis TG(14:0/20:4(8Z,11Z,14Z,17Z)/24:1(15Z)) pathway, and phosphatidylethanolamine biosynthesis pe(14:0/20:4(8Z,11Z,14Z,17Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
DG(34:4)Lipid Annotator, HMDB
DAG(34:4)Lipid Annotator, HMDB
Diacylglycerol(34:4)Lipid Annotator, HMDB
DG(14:0/20:4(8Z,11Z,14Z,17Z)/0:0)Lipid Annotator
DiglycerideLipid Annotator, HMDB
DG(14:0/20:4)Lipid Annotator, HMDB
DAG(14:0/20:4)Lipid Annotator, HMDB
DiacylglycerolLipid Annotator, HMDB
Diacylglycerol(14:0/20:4)Lipid Annotator, HMDB
1-tetradecanoyl-2-(8Z,11Z,14Z,17Z-eicosapentaenoyl)-sn-glycerolLipid Annotator, HMDB
1-myristoyl-2-eicsoatetraenoyl-sn-glycerolLipid Annotator, HMDB
Chemical FormulaC37H64O5
Average Molecular Weight588.9011
Monoisotopic Molecular Weight588.475375158
IUPAC Name(2S)-1-hydroxy-3-(tetradecanoyloxy)propan-2-yl (8Z,11Z,14Z,17Z)-icosa-8,11,14,17-tetraenoate
Traditional Namediacylglycerol
CAS Registry NumberNot Available
SMILES
[H][C@](CO)(COC(=O)CCCCCCCCCCCCC)OC(=O)CCCCCC\C=C/C\C=C/C\C=C/C\C=C/CC
InChI Identifier
InChI=1S/C37H64O5/c1-3-5-7-9-11-13-15-16-17-18-19-20-22-24-26-28-30-32-37(40)42-35(33-38)34-41-36(39)31-29-27-25-23-21-14-12-10-8-6-4-2/h5,7,11,13,16-17,19-20,35,38H,3-4,6,8-10,12,14-15,18,21-34H2,1-2H3/b7-5-,13-11-,17-16-,20-19-/t35-/m0/s1
InChI KeyVAWMHRKGQOLSLO-LAOUYMLRSA-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 DescriptorsNot Available
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
logP9.41ALOGPS
logP11.44ChemAxon
logS-7.4ALOGPS
pKa (Strongest Acidic)14.58ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area72.83 ŲChemAxon
Rotatable Bond Count32ChemAxon
Refractivity181.37 m³·mol⁻¹ChemAxon
Polarizability73.5 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, Positivesplash10-001a-5951203000-fb00ca958e6f6fb1ab74View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS ("DG(14:0/20:4(8Z,11Z,14Z,17Z)/0:0),1TMS,#1" TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-1044090000-600a88fbd28d9e904b27View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-3092000000-9f276f26851be956aa05View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pdi-4294000000-2bdb8a47e342f9c51238View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0000009000-b3b3c003f4a39cd41d77View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01w0-0099071000-2e1e32219eae17778c47View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06ri-0099036000-4adf62d08e82de369f30View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0000009000-ef32778e747adcbc98abView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01w0-0099071000-ec6c38c01f71f72750b5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06ri-0099036000-b10a74521a976ac3d054View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-1065090000-91572653f0cfdc291e81View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01p9-2093030000-50b5edbbdd6de95d9a45View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01ri-8597000000-d5391ad1b2f7b7ce9561View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000009000-7aced06f5b39c28eb59fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0000009000-7aced06f5b39c28eb59fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a60-0009000000-82254060cbab5b38af3bView in MoNA
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 IDHMDB0007026
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID24765860
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53477961
PDB IDNot Available
ChEBI IDNot Available
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(14:0/20:4(8Z,11Z,14Z,17Z)/0:0) → Cytidine monophosphate + PE(14:0/20:4(8Z,11Z,14Z,17Z))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(14:0/20:4(8Z,11Z,14Z,17Z)/0:0) + Docosanoyl-CoA → TG(14:0/20:4(8Z,11Z,14Z,17Z)/22:0) + Coenzyme Adetails
DG(14:0/20:4(8Z,11Z,14Z,17Z)/0:0) + Erucoyl-CoA → TG(14:0/20:4(8Z,11Z,14Z,17Z)/22:1(13Z)) + Coenzyme Adetails
DG(14:0/20:4(8Z,11Z,14Z,17Z)/0:0) + Clupanodonyl CoA → TG(14:0/20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z)) + Coenzyme Adetails
DG(14:0/20:4(8Z,11Z,14Z,17Z)/0:0) + Tetracosanoyl-CoA → TG(14:0/20:4(8Z,11Z,14Z,17Z)/24:0) + Coenzyme Adetails