Showing metabocard for DG(14:1(9Z)/20:2(11Z,14Z)/0:0) (BMDB0007051)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 23:29:31 UTC
Update Date2020-05-21 16:27:28 UTC
BMDB IDBMDB0007051
Secondary Accession Numbers
  • BMDB07051
Metabolite Identification
Common NameDG(14:1(9Z)/20:2(11Z,14Z)/0:0)
DescriptionDG(14:1(9Z)/20:2(11Z,14Z)/0:0), also known as diacylglycerol(14:1/20:2) or DG(14:1/20:2), belongs to the class of organic compounds known as 1,2-diacylglycerols. These are diacylglycerols containing a glycerol acylated at positions 1 and 2. Thus, DG(14:1(9Z)/20:2(11Z,14Z)/0:0) is considered to be a diradylglycerol lipid molecule. DG(14:1(9Z)/20:2(11Z,14Z)/0:0) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. DG(14:1(9Z)/20:2(11Z,14Z)/0:0) participates in a number of enzymatic reactions, within cattle. In particular, DG(14:1(9Z)/20:2(11Z,14Z)/0:0) can be biosynthesized from PA(14:1(9Z)/20:2(11Z,14Z)) through the action of the enzyme phosphatidate phosphatase. Furthermore, DG(14:1(9Z)/20:2(11Z,14Z)/0:0) and meadoyl-CoA can be converted into TG(14:1(9Z)/20:2(11Z,14Z)/20:3(5Z,8Z,11Z)) through the action of the enzyme diacylglycerol O-acyltransferase. Furthermore, DG(14:1(9Z)/20:2(11Z,14Z)/0:0) can be biosynthesized from PA(14:1(9Z)/20:2(11Z,14Z)) through its interaction with the enzyme phosphatidate phosphatase. Furthermore, DG(14:1(9Z)/20:2(11Z,14Z)/0:0) and docosanoyl-CoA can be converted into TG(14:1(9Z)/20:2(11Z,14Z)/22:0) through its interaction with the enzyme diacylglycerol O-acyltransferase. Furthermore, DG(14:1(9Z)/20:2(11Z,14Z)/0:0) can be biosynthesized from PA(14:1(9Z)/20:2(11Z,14Z)); which is catalyzed by the enzyme phosphatidate phosphatase. Finally, DG(14:1(9Z)/20:2(11Z,14Z)/0:0) and nervonoyl-CoA can be converted into TG(14:1(9Z)/20:2(11Z,14Z)/24:1(15Z)) through the action of the enzyme diacylglycerol O-acyltransferase. In cattle, DG(14:1(9Z)/20:2(11Z,14Z)/0:0) is involved in a few metabolic pathways, which include de novo triacylglycerol biosynthesis TG(14:1(9Z)/20:2(11Z,14Z)/20:3(5Z,8Z,11Z)) pathway, de novo triacylglycerol biosynthesis TG(14:1(9Z)/20:2(11Z,14Z)/22:0) pathway, and de novo triacylglycerol biosynthesis TG(14:1(9Z)/20:2(11Z,14Z)/24:1(15Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Myristoleoyl-2-eicosadienoyl-sn-glycerolHMDB
Diacylglycerol(14:1/20:2)HMDB
DiglycerideHMDB
DG(14:1/20:2)HMDB
DAG(34:3)HMDB
DiacylglycerolHMDB
DG(34:3)HMDB
DAG(14:1/20:2)HMDB
1-(9Z-Tetradecenoyl)-2-(11Z,14Z-eicosadienoyl)-sn-glycerolHMDB
Diacylglycerol(34:3)HMDB
DG(14:1(9Z)/20:2(11Z,14Z)/0:0)Lipid Annotator
Chemical FormulaC37H66O5
Average Molecular Weight590.9169
Monoisotopic Molecular Weight590.491025222
IUPAC Name(2S)-1-hydroxy-3-[(9Z)-tetradec-9-enoyloxy]propan-2-yl (11Z,14Z)-icosa-11,14-dienoate
Traditional Namediacylglycerol
CAS Registry NumberNot Available
SMILES
[H]\C(CCCC)=C(/[H])CCCCCCCC(=O)OC[C@]([H])(CO)OC(=O)CCCCCCCCC\C([H])=C(\[H])C\C([H])=C(\[H])CCCCC
InChI Identifier
InChI=1S/C37H66O5/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/h10-13,16-17,35,38H,3-9,14-15,18-34H2,1-2H3/b12-10-,13-11-,17-16-/t35-/m0/s1
InChI KeyYMQRUULVAHFQLL-MJRSHOOBSA-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
logP9.72ALOGPS
logP11.81ChemAxon
logS-7.6ALOGPS
pKa (Strongest Acidic)14.58ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area72.83 ŲChemAxon
Rotatable Bond Count33ChemAxon
Refractivity180.25 m³·mol⁻¹ChemAxon
Polarizability74.86 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, Positivesplash10-0aba-8694437000-8548276aa480632b4b25View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS ("DG(14:1(9Z)/20:2(11Z,14Z)/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, Positivesplash10-0a4i-0000009000-2c9dba2a539fdca961d6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01cr-0099071000-8aaff2a55104bd0d861fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0689-0099036000-027ba514fa4e32482142View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000009000-06c2ad30942913111b60View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0000009000-06c2ad30942913111b60View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a50-0009000000-875fa55f7d21b57db797View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0097180000-c9c242543bfed6441d62View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000x-1495020000-d8b4fdd21c76bf42c236View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9720000000-39605ba5c9345b7a8fa7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4s-3079050000-b7cef28cb484ce4f0389View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00fr-4093000000-e4d0106d855d80d29eebView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-3692000000-b2902a8409a1c6744d4cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0000009000-418bfe830d05946bacd1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01cr-0099071000-9c6c84b2e7fe4b16032eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0689-0099036000-8a796f9673a090f5a7a4View 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 IDHMDB0007051
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 Compound53477986
PDB IDNot Available
ChEBI ID88723
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(14:1(9Z)/20:2(11Z,14Z)/0:0) → Cytidine monophosphate + PE(14:1(9Z)/20:2(11Z,14Z))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(14:1(9Z)/20:2(11Z,14Z)/0:0) + 5Z,8Z,11Z,14Z-eicosatetraenonyl-CoA → TG(14:1(9Z)/20:2n6/20:4(5Z,8Z,11Z,14Z)) + Coenzyme Adetails
DG(14:1(9Z)/20:2(11Z,14Z)/0:0) + Erucoyl-CoA → TG(14:1(9Z)/20:2n6/22:1(13Z)) + Coenzyme Adetails
DG(14:1(9Z)/20:2(11Z,14Z)/0:0) + Clupanodonyl CoA → TG(14:1(9Z)/20:2n6/22:5(7Z,10Z,13Z,16Z,19Z)) + Coenzyme Adetails