Showing metabocard for DG(14:0/20:1(11Z)/0:0) (BMDB0007021)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 23:28:55 UTC
Update Date2020-05-21 16:27:22 UTC
BMDB IDBMDB0007021
Secondary Accession Numbers
  • BMDB07021
Metabolite Identification
Common NameDG(14:0/20:1(11Z)/0:0)
DescriptionDG(14:0/20:1(11Z)/0:0), also known as DG(14:0/20:1) or diacylglycerol(34:1), 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(14:0/20:1(11Z)/0:0) is considered to be a diradylglycerol lipid molecule. DG(14:0/20:1(11Z)/0:0) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. DG(14:0/20:1(11Z)/0:0) participates in a number of enzymatic reactions, within cattle. In particular, DG(14:0/20:1(11Z)/0:0) can be biosynthesized from PA(14:0/20:1(11Z)); which is catalyzed by the enzyme phosphatidate phosphatase. Furthermore, DG(14:0/20:1(11Z)/0:0) and gondoyl-CoA can be converted into TG(14:0/20:1(11Z)/20:1(11Z)); which is catalyzed by the enzyme diacylglycerol O-acyltransferase. Furthermore, DG(14:0/20:1(11Z)/0:0) can be biosynthesized from PA(14:0/20:1(11Z)) through the action of the enzyme phosphatidate phosphatase. Furthermore, DG(14:0/20:1(11Z)/0:0) and docosanoyl-CoA can be converted into TG(14:0/20:1(11Z)/22:0) through the action of the enzyme diacylglycerol O-acyltransferase. Furthermore, DG(14:0/20:1(11Z)/0:0) can be biosynthesized from PA(14:0/20:1(11Z)); which is catalyzed by the enzyme phosphatidate phosphatase. Finally, DG(14:0/20:1(11Z)/0:0) and clupanodonoyl-CoA can be converted into TG(14:0/20:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)); which is catalyzed by the enzyme diacylglycerol O-acyltransferase. In cattle, DG(14:0/20:1(11Z)/0:0) is involved in a few metabolic pathways, which include de novo triacylglycerol biosynthesis TG(14:0/20:1(11Z)/20:1(11Z)) pathway, de novo triacylglycerol biosynthesis TG(14:0/20:1(11Z)/22:0) pathway, and de novo triacylglycerol biosynthesis TG(14:0/20:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
DG(14:0/20:1)Lipid Annotator, HMDB
DAG(14:0/20:1)Lipid Annotator, HMDB
DG(14:0/20:1(11Z)/0:0)Lipid Annotator
DiglycerideLipid Annotator, HMDB
1-myristoyl-2-eicosenoyl-sn-glycerolLipid Annotator, HMDB
Diacylglycerol(34:1)Lipid Annotator, HMDB
DiacylglycerolLipid Annotator, HMDB
DAG(34:1)Lipid Annotator, HMDB
Diacylglycerol(14:0/20:1)Lipid Annotator, HMDB
1-tetradecanoyl-2-(11-eicosenoyl)-sn-glycerolLipid Annotator, HMDB
DG(34:1)Lipid Annotator, HMDB
Chemical FormulaC37H70O5
Average Molecular Weight594.9487
Monoisotopic Molecular Weight594.52232535
IUPAC Name(2S)-1-hydroxy-3-(tetradecanoyloxy)propan-2-yl (11Z)-icos-11-enoate
Traditional Namediacylglycerol
CAS Registry NumberNot Available
SMILES
[H]\C(CCCCCCCC)=C(/[H])CCCCCCCCCC(=O)O[C@@]([H])(CO)COC(=O)CCCCCCCCCCCCC
InChI Identifier
InChI=1S/C37H70O5/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/h16-17,35,38H,3-15,18-34H2,1-2H3/b17-16-/t35-/m0/s1
InChI KeyVQOIASKPUKUIDV-CEJFXXFTSA-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
logP10.1ALOGPS
logP12.53ChemAxon
logS-7.5ALOGPS
pKa (Strongest Acidic)14.58ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area72.83 ŲChemAxon
Rotatable Bond Count35ChemAxon
Refractivity178.02 m³·mol⁻¹ChemAxon
Polarizability77.49 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, Positivesplash10-0uyi-5961445000-7167d7f84ab8d2d86298View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS ("DG(14:0/20:1(11Z)/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, Positivesplash10-03di-0000009000-225d2aaf58bce54f763bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0179-0099071000-fa06f0f0969553371397View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-02tr-0099036000-93f1da7a844123b359fcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0000009000-d1dcc3e98924441c6a0dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0000009000-d1dcc3e98924441c6a0dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a50-0009000000-07dac1862710b86b88d9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000009000-665e2e7dfdb7932c6210View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0179-0099071000-288787699f6f4419f693View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-02tr-0099036000-11baa7f00c98fac68e80View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0kbf-2069050000-6b2986b622f8edb3ee2cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056u-3095010000-6589ca9845ee522aad69View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6r-2296000000-e5c1d809b1954aa80428View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kb-1146190000-b227a81a206840512010View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-06to-0190000000-4b6b0067a385c20b7991View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ac4-6920000000-39c9a14f254694188f3eView 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 IDHMDB0007021
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID24765855
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53477956
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(14:0/20:1(11Z)/0:0) → Cytidine monophosphate + PE(14:0/20:1(11Z))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(14:0/20:1(11Z)/0:0) + Gondoyl-CoA → TG(14:0/20:1(11Z)/20:1(11Z))[iso3] + Coenzyme Adetails
DG(14:0/20:1(11Z)/0:0) + 5Z,8Z,11Z,14Z-eicosatetraenonyl-CoA → TG(14:0/20:1(11Z)/20:4(5Z,8Z,11Z,14Z))[iso6] + Coenzyme Adetails
DG(14:0/20:1(11Z)/0:0) + Docosanoyl-CoA → TG(14:0/20:1(11Z)/22:0) + Coenzyme Adetails
DG(14:0/20:1(11Z)/0:0) + Erucoyl-CoA → TG(14:0/20:1(11Z)/22:1(13Z)) + Coenzyme Adetails
DG(14:0/20:1(11Z)/0:0) + Clupanodonyl CoA → TG(14:0/20:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))[iso6] + Coenzyme Adetails
DG(14:0/20:1(11Z)/0:0) + Tetracosanoyl-CoA → TG(14:0/20:1(11Z)/24:0) + Coenzyme Adetails