Showing metabocard for DG(14:1(9Z)/14:1(9Z)/0:0) (BMDB0007038)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 23:29:15 UTC
Update Date2020-05-21 16:27:24 UTC
BMDB IDBMDB0007038
Secondary Accession Numbers
  • BMDB07038
Metabolite Identification
Common NameDG(14:1(9Z)/14:1(9Z)/0:0)
DescriptionDG(14:1(9Z)/14:1(9Z)/0:0), also known as DAG(14:1/14:1) or dg(14:1(9z)/14:1(9z)/0:0), belongs to the class of organic compounds known as 1,2-dg(14:1(9z)/14:1(9z)/0:0)s. These are dg(14:1(9z)/14:1(9z)/0:0)s containing a glycerol acylated at positions 1 and 2. Thus, DG(14:1(9Z)/14:1(9Z)/0:0) is considered to be a diradylglycerol lipid molecule. DG(14:1(9Z)/14:1(9Z)/0:0) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. DG(14:1(9Z)/14:1(9Z)/0:0) participates in a number of enzymatic reactions, within cattle. In particular, DG(14:1(9Z)/14:1(9Z)/0:0) can be biosynthesized from PA(14:1(9Z)/14:1(9Z)); which is catalyzed by the enzyme phosphatidate phosphatase. Furthermore, DG(14:1(9Z)/14:1(9Z)/0:0) and palmitoleyl-CoA can be converted into TG(14:1(9Z)/14:1(9Z)/16:1(9Z)) through its interaction with the enzyme dg(14:1(9z)/14:1(9z)/0:0) O-acyltransferase. Furthermore, DG(14:1(9Z)/14:1(9Z)/0:0) can be biosynthesized from PA(14:1(9Z)/14:1(9Z)); which is mediated by the enzyme phosphatidate phosphatase. Furthermore, DG(14:1(9Z)/14:1(9Z)/0:0) and stearidonoyl-CoA can be converted into TG(14:1(9Z)/14:1(9Z)/18:4(6Z,9Z,12Z,15Z)) through the action of the enzyme dg(14:1(9z)/14:1(9z)/0:0) O-acyltransferase. Furthermore, DG(14:1(9Z)/14:1(9Z)/0:0) can be biosynthesized from PA(14:1(9Z)/14:1(9Z)); which is mediated by the enzyme phosphatidate phosphatase. Finally, DG(14:1(9Z)/14:1(9Z)/0:0) and dihomo-gamma-linolenoyl-CoA can be converted into TG(14:1(9Z)/14:1(9Z)/20:3(8Z,11Z,14Z)); which is catalyzed by the enzyme dg(14:1(9z)/14:1(9z)/0:0) O-acyltransferase. In cattle, DG(14:1(9Z)/14:1(9Z)/0:0) is involved in several metabolic pathways, some of which include de novo triacylglycerol biosynthesis TG(14:1(9Z)/14:1(9Z)/16:1(9Z)) pathway, de novo triacylglycerol biosynthesis TG(14:1(9Z)/14:1(9Z)/18:4(6Z,9Z,12Z,15Z)) pathway, de novo triacylglycerol biosynthesis TG(14:1(9Z)/14:1(9Z)/20:3(8Z,11Z,14Z)) pathway, de novo triacylglycerol biosynthesis TG(14:1(9Z)/14:1(9Z)/20:4(8Z,11Z,14Z,17Z)) pathway, and de novo triacylglycerol biosynthesis TG(14:1(9Z)/14:1(9Z)/22:4(7Z,10Z,13Z,16Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
DAG(14:1/14:1)ChEBI
DAG(14:1N5/14:1N5)ChEBI
DAG(14:1W5/14:1W5)ChEBI
DAG(28:2)ChEBI
DG(14:1/14:1)ChEBI
DG(14:1N5/14:1N5)ChEBI
DG(14:1W5/14:1W5)ChEBI
Diacylglycerol(14:1/14:1)ChEBI
Diacylglycerol(14:1n5/14:1n5)ChEBI
Diacylglycerol(14:1W5/14:1W5)ChEBI
DG(28:2)Lipid Annotator, HMDB
DG(14:1(9Z)/14:1(9Z)/0:0)Lipid Annotator
DiglycerideLipid Annotator, HMDB
DiacylglycerolLipid Annotator, HMDB
1,2-dimyristoleoyl-rac-glycerolLipid Annotator, HMDB
1,2-di(9Z-tetradecenoyl)-rac-glycerolLipid Annotator, HMDB
Diacylglycerol(28:2)Lipid Annotator, HMDB
Chemical FormulaC31H56O5
Average Molecular Weight508.7733
Monoisotopic Molecular Weight508.412774902
IUPAC Name(2S)-1-hydroxy-3-[(9Z)-tetradec-9-enoyloxy]propan-2-yl (9Z)-tetradec-9-enoate
Traditional Namediacylglycerol
CAS Registry NumberNot Available
SMILES
[H][C@](CO)(COC(=O)CCCCCCC\C=C/CCCC)OC(=O)CCCCCCC\C=C/CCCC
InChI Identifier
InChI=1S/C31H56O5/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/h9-12,29,32H,3-8,13-28H2,1-2H3/b11-9-,12-10-/t29-/m0/s1
InChI KeyUOMACDOEROJUON-XRZSNXEXSA-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
logP8.6ALOGPS
logP9.5ChemAxon
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 Count28ChemAxon
Refractivity151.53 m³·mol⁻¹ChemAxon
Polarizability64.03 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, Positivesplash10-0pbi-6429650000-8f14710e35d05e3ce197View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0000090000-88e837da3a19e0f95915View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001l-0090630000-e307612f69b43b96ae6eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-003r-0090170000-e629542318ebc29a23abView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0000090000-3eb10596d5d6738f77fbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001l-0090630000-8027350758e1947db1adView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-003r-0090170000-eed22d58976a25990d03View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000090000-59b51b79f75303149528View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0000090000-59b51b79f75303149528View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-0019010000-c8c379b69374f7754269View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-1080090000-2f282318524a7dbea5e8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05di-2090000000-50e6e2580ef833107281View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-1290000000-983d09235bd7c96ae0a8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-4391870000-ae009492de6399ceb729View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a59-4291300000-6de1ea102c0012d8ee01View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a59-5590000000-06709948880b8ad7318aView 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 IDHMDB0007038
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID24765872
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53477973
PDB IDNot Available
ChEBI ID84702
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)/14:1(9Z)/0:0) → Cytidine monophosphate + PE(14:1(9Z)/14:1(9Z))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)/14:1(9Z)/0:0) + Palmityl-CoA → TG(14:1(9Z)/14:1(9Z)/16:0)[iso3] + Coenzyme Adetails
DG(14:1(9Z)/14:1(9Z)/0:0) + Palmitoleyl CoA → TG(14:1(9Z)/14:1(9Z)/16:1(9Z)) + Coenzyme Adetails
DG(14:1(9Z)/14:1(9Z)/0:0) + Stearoyl-CoA → TG(14:1(9Z)/14:1(9Z)/18:0)[iso3] + Coenzyme Adetails
DG(14:1(9Z)/14:1(9Z)/0:0) + Oleoyl-CoA → TG(14:1(9Z)/14:1(9Z)/18:1(9Z)) + Coenzyme Adetails
DG(14:1(9Z)/14:1(9Z)/0:0) + Gamma-linolenoyl-CoA → TG(14:1(9Z)/14:1(9Z)/18:3(6Z,9Z,12Z)) + Coenzyme Adetails
DG(14:1(9Z)/14:1(9Z)/0:0) + Eicosanoyl-CoA → TG(14:1(9Z)/14:1(9Z)/20:0)[iso3] + Coenzyme Adetails
DG(14:1(9Z)/14:1(9Z)/0:0) + Gondoyl-CoA → TG(14:1(9Z)/14:1(9Z)/20:1(11Z))[iso3] + Coenzyme Adetails
DG(14:1(9Z)/14:1(9Z)/0:0) + 5Z,8Z,11Z,14Z-eicosatetraenonyl-CoA → TG(14:1(9Z)/14:1(9Z)/20:4(5Z,8Z,11Z,14Z)) + Coenzyme Adetails
DG(14:1(9Z)/14:1(9Z)/0:0) + Docosanoyl-CoA → TG(14:1(9Z)/14:1(9Z)/22:0)[iso3] + Coenzyme Adetails
DG(14:1(9Z)/14:1(9Z)/0:0) + Erucoyl-CoA → TG(14:1(9Z)/14:1(9Z)/22:1(13Z)) + Coenzyme Adetails
DG(14:1(9Z)/14:1(9Z)/0:0) + Clupanodonyl CoA → TG(14:1(9Z)/14:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)) + Coenzyme Adetails