Showing metabocard for DG(16:1(9Z)/20:0/0:0) (BMDB0007136)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 23:31:18 UTC
Update Date2020-05-21 16:27:44 UTC
BMDB IDBMDB0007136
Secondary Accession Numbers
  • BMDB07136
Metabolite Identification
Common NameDG(16:1(9Z)/20:0/0:0)
DescriptionDG(16:1(9Z)/20:0/0:0)[iso2], also known as DAG(16:1/20:0) or dg(16:1(9z)/20:0/0:0)[iso2], belongs to the class of organic compounds known as 1,2-dg(16:1(9z)/20:0/0:0)[iso2]s. These are dg(16:1(9z)/20:0/0:0)[iso2]s containing a glycerol acylated at positions 1 and 2. Thus, DG(16:1(9Z)/20:0/0:0)[iso2] is considered to be a diradylglycerol lipid molecule. DG(16:1(9Z)/20:0/0:0)[iso2] is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. In cattle, DG(16:1(9Z)/20:0/0:0)[iso2] is involved in a couple of metabolic pathways, which include de novo triacylglycerol biosynthesis TG(16:1(9Z)/20:0/20:3(5Z,8Z,11Z)) pathway and de novo triacylglycerol biosynthesis TG(16:1(9Z)/20:0/22:0) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-palmitoleoyl-2-arachidonyl-sn-glycerolLipid Annotator, HMDB
DAG(36:1)Lipid Annotator, HMDB
DAG(16:1/20:0)Lipid Annotator, HMDB
Diacylglycerol(36:1)Lipid Annotator, HMDB
DG(36:1)Lipid Annotator, HMDB
DiglycerideLipid Annotator, HMDB
DiacylglycerolLipid Annotator, HMDB
Diacylglycerol(16:1/20:0)Lipid Annotator, HMDB
DG(16:1(9Z)/20:0/0:0)Lipid Annotator
1-(9Z-hexadecenoyl)-2-eicosanoyl-sn-glycerolLipid Annotator, HMDB
DG(16:1/20:0)Lipid Annotator, HMDB
Chemical FormulaC39H74O5
Average Molecular Weight623.0019
Monoisotopic Molecular Weight622.553625478
IUPAC Name(2S)-1-[(9Z)-hexadec-9-enoyloxy]-3-hydroxypropan-2-yl icosanoate
Traditional Namediacylglycerol
CAS Registry NumberNot Available
SMILES
[H][C@](CO)(COC(=O)CCCCCCC\C=C/CCCCCC)OC(=O)CCCCCCCCCCCCCCCCCCC
InChI Identifier
InChI=1S/C39H74O5/c1-3-5-7-9-11-13-15-17-18-19-20-22-24-26-28-30-32-34-39(42)44-37(35-40)36-43-38(41)33-31-29-27-25-23-21-16-14-12-10-8-6-4-2/h14,16,37,40H,3-13,15,17-36H2,1-2H3/b16-14-/t37-/m0/s1
InChI KeyCJEAOBNZIRDIRB-KDKAWYBRSA-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
logP10.35ALOGPS
logP13.42ChemAxon
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 Count37ChemAxon
Refractivity187.22 m³·mol⁻¹ChemAxon
Polarizability82.34 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, Positivesplash10-00aa-4492247000-68a0e6c6a546ac92fd4bView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS ("DG(16:1(9Z)/20:0/0:0),1TMS,#1" TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000009000-fce9091ab20877af1859View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-09k9-0009004000-89fd09f496c20c135108View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-04i3-0009004000-a9178d374bddc5517123View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-006t-2194016000-9fe9f578b4fea9d253a8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-3293001000-1cf1c5758a2fafea9902View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-054k-9452000000-25e370deefe97244ba91View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0000009000-8b1291422a70b2640ab8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0000009000-8b1291422a70b2640ab8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001o-0009000000-d9b4a5aa97bc141234d0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0fk9-1087009000-4ff04be6f314162ea1f9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0h2r-3079001000-17ebca8b897c8e5749c5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0w2l-2294000000-fe32e48370bb8a6adae3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000009000-bab9e83f09359631bc8fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-09k9-0009004000-9f69dc10c85b33789d78View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-04i3-0009004000-a5be03d7b0fdbe55b83cView 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 IDHMDB0007136
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID7822664
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9543714
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(16:1(9Z)/20:0/0:0) → Cytidine monophosphate + PE(16:1(9Z)/20:0)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(16:1(9Z)/20:0/0:0) + Eicosanoyl-CoA → TG(16:1(9Z)/20:0/20:0) + Coenzyme Adetails
DG(16:1(9Z)/20:0/0:0) + Gondoyl-CoA → TG(16:1(9Z)/20:0/20:1(11Z)) + Coenzyme Adetails
DG(16:1(9Z)/20:0/0:0) + 5Z,8Z,11Z,14Z-eicosatetraenonyl-CoA → TG(16:1(9Z)/20:0/20:4(5Z,8Z,11Z,14Z)) + Coenzyme Adetails
DG(16:1(9Z)/20:0/0:0) + Erucoyl-CoA → TG(16:1(9Z)/20:0/22:1(13Z)) + Coenzyme Adetails
DG(16:1(9Z)/20:0/0:0) + Clupanodonyl CoA → TG(16:1(9Z)/20:0/22:5(7Z,10Z,13Z,16Z,19Z)) + Coenzyme Adetails