Showing metabocard for DG(16:0/16:1(9Z)/0:0) (BMDB0007099)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 23:30:34 UTC
Update Date2020-05-21 16:27:37 UTC
BMDB IDBMDB0007099
Secondary Accession Numbers
  • BMDB07099
Metabolite Identification
Common NameDG(16:0/16:1(9Z)/0:0)
DescriptionDG(16:0/16:1(9Z)/0:0), also known as diacylglycerol or DAG(16:0/16:1), 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(16:0/16:1(9Z)/0:0) is considered to be a diradylglycerol lipid molecule. DG(16:0/16:1(9Z)/0:0) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. DG(16:0/16:1(9Z)/0:0) exists in all living organisms, ranging from bacteria to humans. DG(16:0/16:1(9Z)/0:0) participates in a number of enzymatic reactions, within cattle. In particular, CDP-Ethanolamine and DG(16:0/16:1(9Z)/0:0) can be converted into cytidine monophosphate and PE(16:0/16:1(9Z)); which is mediated by the enzyme choline/ethanolaminephosphotransferase. In addition, CDP-Choline and DG(16:0/16:1(9Z)/0:0) can be converted into cytidine monophosphate and PC(16:0/16:1(9Z)); which is mediated by the enzyme choline/ethanolaminephosphotransferase. In cattle, DG(16:0/16:1(9Z)/0:0) is involved in the metabolic pathway called phosphatidylcholine biosynthesis PC(16:0/16:1(9Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Hexadecanoyl-2-(9Z-hexadecenoyl)-sn-glycerolChEBI
DG(16:0/16:1(9Z)/0:0)[iso2]ChEBI
DG(16:0/16:1/0:0)ChEBI
1-Palmitoyl-2-palmitoleoyl-sn-glycerolHMDB
DAG(16:0/16:1)HMDB
DAG(16:0/16:1N7)HMDB
DAG(16:0/16:1W7)HMDB
DAG(32:1)HMDB
DG(16:0/16:1)HMDB
DG(16:0/16:1N7)HMDB
DG(16:0/16:1W7)HMDB
DG(32:1)HMDB
DiacylglycerolHMDB
Diacylglycerol(16:0/16:1)HMDB
Diacylglycerol(16:0/16:1n7)HMDB
Diacylglycerol(16:0/16:1W7)HMDB
Diacylglycerol(32:1)HMDB
DiglycerideHMDB
DG(16:0/16:1(9Z)/0:0)Lipid Annotator
Chemical FormulaC35H66O5
Average Molecular Weight566.8955
Monoisotopic Molecular Weight566.491025222
IUPAC Name(2S)-1-(hexadecanoyloxy)-3-hydroxypropan-2-yl (9Z)-hexadec-9-enoate
Traditional Namediacylglycerol
CAS Registry NumberNot Available
SMILES
[H]\C(CCCCCC)=C(/[H])CCCCCCCC(=O)O[C@@]([H])(CO)COC(=O)CCCCCCCCCCCCCCC
InChI Identifier
InChI=1S/C35H66O5/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-34(37)39-32-33(31-36)40-35(38)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h14,16,33,36H,3-13,15,17-32H2,1-2H3/b16-14-/t33-/m0/s1
InChI KeyADLOEVQMJKYKSR-YAIMUBSCSA-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
Polarizability73.74 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, Positivesplash10-02mr-4494243000-a2801af8a2bc289fee6dView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS ("DG(16:0/16:1(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, Positivesplash10-03di-0009040000-3c1791947011276d636bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-0009040000-119a2afcb7ba02ef3e20View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-02t9-3147190000-d918fde303823d259855View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000l-3982000000-3ea933d8296f60ffa09eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05ne-9300000000-587a099e2a74c0fda4d2View 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, Positivesplash10-03di-0009040000-93ce060af4d8747b5574View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-0009040000-bb79d66b7eef0c685dcfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0gdi-3079070000-10ce2f87c203861ebc41View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-11p1-2093010000-d325a0d00d948b93854aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0zfr-0090000000-6c6c0f9030b111cad233View 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, Positivesplash10-0019-0019000000-c2f7fd217157a6cb34a1View 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 IDHMDB0007099
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB024293
KNApSAcK IDNot Available
Chemspider ID7822628
KEGG Compound IDC00165
BioCyc IDDIACYLGLYCEROL
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID4264
PubChem Compound9543678
PDB IDNot Available
ChEBI ID84394
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(16:0/16:1(9Z)/0:0) → Cytidine monophosphate + PE(16:0/16:1(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(16:0/16:1(9Z)/0:0) + Palmitoleyl CoA → TG(16:0/16:1(9Z)/16:1(9Z)) + Coenzyme Adetails
DG(16:0/16:1(9Z)/0:0) + Stearoyl-CoA → TG(16:0/16:1(9Z)/18:0) + Coenzyme Adetails
DG(16:0/16:1(9Z)/0:0) + Oleoyl-CoA → TG(16:0/16:1(9Z)/18:1(9Z)) + Coenzyme Adetails
DG(16:0/16:1(9Z)/0:0) + Gamma-linolenoyl-CoA → TG(16:0/16:1(9Z)/18:3(6Z,9Z,12Z))[iso6] + Coenzyme Adetails
DG(16:0/16:1(9Z)/0:0) + Eicosanoyl-CoA → TG(16:0/16:1(9Z)/20:0) + Coenzyme Adetails
DG(16:0/16:1(9Z)/0:0) + Gondoyl-CoA → TG(16:0/16:1(9Z)/20:1(11Z)) + Coenzyme Adetails
DG(16:0/16:1(9Z)/0:0) + 5Z,8Z,11Z,14Z-eicosatetraenonyl-CoA → TG(16:0/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)) + Coenzyme Adetails
DG(16:0/16:1(9Z)/0:0) + Docosanoyl-CoA → TG(16:0/16:1(9Z)/22:0) + Coenzyme Adetails
DG(16:0/16:1(9Z)/0:0) + Erucoyl-CoA → TG(16:0/16:1(9Z)/22:1(13Z))[iso6] + Coenzyme Adetails
DG(16:0/16:1(9Z)/0:0) + Clupanodonyl CoA → TG(16:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))[iso6] + Coenzyme Adetails
DG(16:0/16:1(9Z)/0:0) + Tetracosanoyl-CoA → TG(16:0/16:1(9Z)/24:0) + Coenzyme Adetails