Showing metabocard for DG(14:0/18:1(9Z)/0:0) (BMDB0007015)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 23:28:47 UTC
Update Date2020-05-21 16:27:20 UTC
BMDB IDBMDB0007015
Secondary Accession Numbers
  • BMDB07015
Metabolite Identification
Common NameDG(14:0/18:1(9Z)/0:0)
DescriptionDG(14:0/18:1(9Z)/0:0), also known as diacylglycerol or DAG(14:0/18:1), 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(14:0/18:1(9Z)/0:0) is considered to be a diradylglycerol lipid molecule. DG(14:0/18:1(9Z)/0:0) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. DG(14:0/18:1(9Z)/0:0) exists in all living organisms, ranging from bacteria to humans. DG(14:0/18:1(9Z)/0:0) participates in a number of enzymatic reactions, within cattle. In particular, DG(14:0/18:1(9Z)/0:0) can be biosynthesized from PA(14:0/18:1(9Z)); which is mediated by the enzyme phosphatidate phosphatase. In addition, DG(14:0/18:1(9Z)/0:0) and oleoyl-CoA can be converted into TG(14:0/18:1(9Z)/18:1(9Z)); which is mediated by the enzyme diacylglycerol O-acyltransferase. In cattle, DG(14:0/18:1(9Z)/0:0) is involved in the metabolic pathway called de novo triacylglycerol biosynthesis TG(14:0/18:1(9Z)/18:1(9Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Tetradecanoyl-2-(9Z)-octadecenoyl-sn-glycerolChEBI
DAG(14:0/18:1)ChEBI
DG (14:0/18:1(N-9)/0:0)ChEBI
DG(14:0/18:1/0:0)ChEBI
DAG(32:1)Lipid Annotator, HMDB
DiglycerideLipid Annotator, HMDB
DG(14:0/18:1)Lipid Annotator, HMDB
DG(14:0/18:1(9Z)/0:0)Lipid Annotator
DiacylglycerolLipid Annotator, HMDB
DG(32:1)Lipid Annotator, HMDB
Diacylglycerol(14:0/18:1)Lipid Annotator, HMDB
Diacylglycerol(32:1)Lipid Annotator, HMDB
1-tetradecanoyl-2-(9Z-octadecenoyl)-sn-glycerolLipid Annotator, HMDB
1-myristoyl-2-oleoyl-sn-glycerolLipid Annotator, HMDB
DAG(14:0/18:1N9)HMDB
DAG(14:0/18:1W9)HMDB
DG(14:0/18:1N9)HMDB
DG(14:0/18:1W9)HMDB
Diacylglycerol(14:0/18:1n9)HMDB
Diacylglycerol(14:0/18:1W9)HMDB
Chemical FormulaC35H66O5
Average Molecular Weight566.8955
Monoisotopic Molecular Weight566.491025222
IUPAC Name(2S)-1-hydroxy-3-(tetradecanoyloxy)propan-2-yl (9Z)-octadec-9-enoate
Traditional Namediacylglycerol
CAS Registry NumberNot Available
SMILES
[H]\C(CCCCCCCC)=C(/[H])CCCCCCCC(=O)O[C@@]([H])(CO)COC(=O)CCCCCCCCCCCCC
InChI Identifier
InChI=1S/C35H66O5/c1-3-5-7-9-11-13-15-16-17-18-20-22-24-26-28-30-35(38)40-33(31-36)32-39-34(37)29-27-25-23-21-19-14-12-10-8-6-4-2/h16-17,33,36H,3-15,18-32H2,1-2H3/b17-16-/t33-/m0/s1
InChI KeyXEQQGHISHUGMIP-ASUORMEESA-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
logP9.82ALOGPS
logP11.64ChemAxon
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 Count33ChemAxon
Refractivity168.82 m³·mol⁻¹ChemAxon
Polarizability73.33 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, Positivesplash10-0fer-5973364000-be579c83467a1a430d4aView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS ("DG(14:0/18:1(9Z)/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, Positivesplash10-001i-0000090000-b10bae501036cc2e6a49View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0099090000-b52ed2072e40ba89d471View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0099090000-b891294f22488166d5f3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014r-1156190000-319208ff76f50ed134c9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014r-0290000000-e455dd22ef573081106cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4j-8900000000-1dc64aa42822050a92e9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000090000-42f8dfc382daebbac87bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0000090000-42f8dfc382daebbac87bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0bt9-0009000000-940a5f42e0441de0c049View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ge9-2095040000-a53e09418fa6b7c5fc39View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-2092010000-9675dee411fd61f6ac88View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-057i-1191000000-87774f928e124bf7c936View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000090000-e397b91a89d2222952f3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0088090000-0adc22fca8ff6c4ed1faView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0088090000-cf59c144cca4867b0207View 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 IDHMDB0007015
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID24765849
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID75465
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(14:0/18:1(9Z)/0:0) → Cytidine monophosphate + PE(14:0/18:1(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(14:0/18:1(9Z)/0:0) + Oleoyl-CoA → TG(14:0/18:1(9Z)/18:1(9Z))[iso3] + Coenzyme Adetails
DG(14:0/18:1(9Z)/0:0) + Gamma-linolenoyl-CoA → TG(14:0/18:1(9Z)/18:3(6Z,9Z,12Z))[iso6] + Coenzyme Adetails
DG(14:0/18:1(9Z)/0:0) + Eicosanoyl-CoA → TG(14:0/18:1(9Z)/20:0) + Coenzyme Adetails
DG(14:0/18:1(9Z)/0:0) + Gondoyl-CoA → TG(14:0/18:1(9Z)/20:1(11Z))[iso6] + Coenzyme Adetails
DG(14:0/18:1(9Z)/0:0) + 5Z,8Z,11Z,14Z-eicosatetraenonyl-CoA → TG(14:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))[iso6] + Coenzyme Adetails
DG(14:0/18:1(9Z)/0:0) + Docosanoyl-CoA → TG(14:0/18:1(9Z)/22:0) + Coenzyme Adetails
DG(14:0/18:1(9Z)/0:0) + Erucoyl-CoA → TG(14:0/18:1(9Z)/22:1(13Z)) + Coenzyme Adetails
DG(14:0/18:1(9Z)/0:0) + Clupanodonyl CoA → TG(14:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))[iso6] + Coenzyme Adetails
DG(14:0/18:1(9Z)/0:0) + Tetracosanoyl-CoA → TG(14:0/18:1(9Z)/24:0) + Coenzyme Adetails