Showing metabocard for DG(16:1(9Z)/18:1(11Z)/0:0) (BMDB0007130)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 23:31:11 UTC
Update Date2020-05-21 16:27:42 UTC
BMDB IDBMDB0007130
Secondary Accession Numbers
  • BMDB07130
Metabolite Identification
Common NameDG(16:1(9Z)/18:1(11Z)/0:0)
DescriptionDG(16:1(9Z)/18:1(11Z)/0:0), also known as dg(16:1(9z)/18:1(11z)/0:0) or DAG(16:1/18:1), belongs to the class of organic compounds known as 1,2-dg(16:1(9z)/18:1(11z)/0:0)s. These are dg(16:1(9z)/18:1(11z)/0:0)s containing a glycerol acylated at positions 1 and 2. DG(16:1(9Z)/18:1(11Z)/0:0) is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). DG(16:1(9Z)/18:1(11Z)/0:0) participates in a number of enzymatic reactions, within cattle. In particular, DG(16:1(9Z)/18:1(11Z)/0:0) can be biosynthesized from PA(16:1(9Z)/18:1(11Z)); which is mediated by the enzyme phosphatidate phosphatase. In addition, DG(16:1(9Z)/18:1(11Z)/0:0) and stearidonoyl-CoA can be converted into TG(16:1(9Z)/18:1(11Z)/18:4(6Z,9Z,12Z,15Z)); which is catalyzed by the enzyme dg(16:1(9z)/18:1(11z)/0:0) O-acyltransferase. In cattle, DG(16:1(9Z)/18:1(11Z)/0:0) is involved in the metabolic pathway called de novo triacylglycerol biosynthesis TG(16:1(9Z)/18:1(11Z)/18:4(6Z,9Z,12Z,15Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
DiglycerideLipid Annotator, HMDB
Diacylglycerol(16:1/18:1)Lipid Annotator, HMDB
DAG(16:1/18:1)Lipid Annotator, HMDB
1-palmitoleoyl-2-vaccenoyl-sn-glycerolLipid Annotator, HMDB
DiacylglycerolLipid Annotator, HMDB
DAG(34:2)Lipid Annotator, HMDB
DG(34:2)Lipid Annotator, HMDB
DG(16:1/18:1)Lipid Annotator, HMDB
DG(16:1(9Z)/18:1(11Z)/0:0)Lipid Annotator
1-(9Z-hexadecenoyl)-2-(11Z-octadecenoyl)-sn-glycerolLipid Annotator, HMDB
Diacylglycerol(34:2)Lipid Annotator, HMDB
Chemical FormulaC37H68O5
Average Molecular Weight592.9328
Monoisotopic Molecular Weight592.506675286
IUPAC Name(2S)-1-[(9Z)-hexadec-9-enoyloxy]-3-hydroxypropan-2-yl (11Z)-octadec-11-enoate
Traditional Namediacylglycerol
CAS Registry NumberNot Available
SMILES
[H][C@](CO)(COC(=O)CCCCCCC\C=C/CCCCCC)OC(=O)CCCCCCCCC\C=C/CCCCCC
InChI Identifier
InChI=1S/C37H68O5/c1-3-5-7-9-11-13-15-17-18-20-22-24-26-28-30-32-37(40)42-35(33-38)34-41-36(39)31-29-27-25-23-21-19-16-14-12-10-8-6-4-2/h13-16,35,38H,3-12,17-34H2,1-2H3/b15-13-,16-14-/t35-/m0/s1
InChI KeyZLSFIDLWXKZYAS-QPFMYUCOSA-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 DescriptorsNot Available
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
logP9.97ALOGPS
logP12.17ChemAxon
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 Count34ChemAxon
Refractivity179.13 m³·mol⁻¹ChemAxon
Polarizability76.41 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, Positivesplash10-000j-5494576000-6d7589e442658945d187View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS ("DG(16:1(9Z)/18:1(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, Negativesplash10-0f6x-1092070000-34eaf2e94eb3f50a1881View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0uki-3093010000-470dcf0eee58e7ab9158View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0uei-2390000000-87dbf657bb68cf55c07fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000009000-f509faf22d917fb30fd3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03g0-0009030000-0ecdddc832226829347dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dr-0009013000-9af45603db7fc3a32630View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0000009000-5799a9dd05585a00daf0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0000009000-5799a9dd05585a00daf0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03f0-0009000000-b75025027ed3a8a213d2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000009000-9c0b9b803bf5ae3e9b28View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03g0-0009030000-9b69a460af4cc814f35bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dr-0009013000-c363a5f2ca5174046e90View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014l-2394280000-6512defa1ad70bad25c9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014r-4693010000-4ca35da39e535121a323View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0699-9652000000-8fb233b17ccd74176195View 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 IDHMDB0007130
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID24765942
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53478037
PDB IDNot Available
ChEBI ID88501
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)/18:1(11Z)/0:0) → Cytidine monophosphate + PE(16:1(9Z)/18:1(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(16:1(9Z)/18:1(11Z)/0:0) + Oleoyl-CoA → TG(16:1(9Z)/18:1(11Z)/18:1(9Z)) + Coenzyme Adetails
DG(16:1(9Z)/18:1(11Z)/0:0) + Gamma-linolenoyl-CoA → TG(16:1(9Z)/18:1(11Z)/18:3(6Z,9Z,12Z)) + Coenzyme Adetails
DG(16:1(9Z)/18:1(11Z)/0:0) + Gondoyl-CoA → TG(16:1(9Z)/18:1(11Z)/20:1(11Z)) + Coenzyme Adetails
DG(16:1(9Z)/18:1(11Z)/0:0) + 5Z,8Z,11Z,14Z-eicosatetraenonyl-CoA → TG(16:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)) + Coenzyme Adetails
DG(16:1(9Z)/18:1(11Z)/0:0) + Erucoyl-CoA → TG(16:1(9Z)/18:1(11Z)/22:1(13Z)) + Coenzyme Adetails
DG(16:1(9Z)/18:1(11Z)/0:0) + Clupanodonyl CoA → TG(16:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)) + Coenzyme Adetails