Showing metabocard for DG(16:1(9Z)/20:2(11Z,14Z)/0:0) (BMDB0007138)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 23:31:20 UTC
Update Date2020-05-21 16:27:44 UTC
BMDB IDBMDB0007138
Secondary Accession Numbers
  • BMDB07138
Metabolite Identification
Common NameDG(16:1(9Z)/20:2(11Z,14Z)/0:0)
DescriptionDG(16:1(9Z)/20:2(11Z,14Z)/0:0), also known as diacylglycerol or DAG(16:1/20:2), 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(16:1(9Z)/20:2(11Z,14Z)/0:0) is considered to be a diradylglycerol lipid molecule. DG(16:1(9Z)/20:2(11Z,14Z)/0:0) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. DG(16:1(9Z)/20:2(11Z,14Z)/0:0) participates in a number of enzymatic reactions, within cattle. In particular, DG(16:1(9Z)/20:2(11Z,14Z)/0:0) can be biosynthesized from PA(16:1(9Z)/20:2(11Z,14Z)) through the action of the enzyme phosphatidate phosphatase. Furthermore, DG(16:1(9Z)/20:2(11Z,14Z)/0:0) and meadoyl-CoA can be converted into TG(16:1(9Z)/20:2(11Z,14Z)/20:3(5Z,8Z,11Z)); which is mediated by the enzyme diacylglycerol O-acyltransferase. Furthermore, DG(16:1(9Z)/20:2(11Z,14Z)/0:0) can be biosynthesized from PA(16:1(9Z)/20:2(11Z,14Z)) through its interaction with the enzyme phosphatidate phosphatase. Furthermore, DG(16:1(9Z)/20:2(11Z,14Z)/0:0) and docosanoyl-CoA can be converted into TG(16:1(9Z)/20:2(11Z,14Z)/22:0); which is catalyzed by the enzyme diacylglycerol O-acyltransferase. Furthermore, DG(16:1(9Z)/20:2(11Z,14Z)/0:0) can be biosynthesized from PA(16:1(9Z)/20:2(11Z,14Z)); which is catalyzed by the enzyme phosphatidate phosphatase. Finally, DG(16:1(9Z)/20:2(11Z,14Z)/0:0) and docosadienoyl-CoA can be converted into TG(16:1(9Z)/20:2(11Z,14Z)/22:2(13Z,16Z)) through the action of the enzyme diacylglycerol O-acyltransferase. In cattle, DG(16:1(9Z)/20:2(11Z,14Z)/0:0) is involved in a few metabolic pathways, which include de novo triacylglycerol biosynthesis TG(16:1(9Z)/20:2(11Z,14Z)/20:3(5Z,8Z,11Z)) pathway, de novo triacylglycerol biosynthesis TG(16:1(9Z)/20:2(11Z,14Z)/22:0) pathway, and de novo triacylglycerol biosynthesis TG(16:1(9Z)/20:2(11Z,14Z)/22:2(13Z,16Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Palmitoleoyl-2-eicosadienoyl-sn-glycerolHMDB
DAG(16:1/20:2)HMDB
DAG(16:1N7/20:2N6)HMDB
DAG(16:1W7/20:2W6)HMDB
DAG(36:3)HMDB
DG(16:1/20:2)HMDB
DG(16:1N7/20:2N6)HMDB
DG(16:1W7/20:2W6)HMDB
DG(36:3)HMDB
DiacylglycerolHMDB
Diacylglycerol(16:1/20:2)HMDB
Diacylglycerol(16:1n7/20:2n6)HMDB
Diacylglycerol(16:1W7/20:2W6)HMDB
Diacylglycerol(36:3)HMDB
DiglycerideHMDB
1-(9Z-Hexadecenoyl)-2-(11Z,14Z-eicosadienoyl)-sn-glycerolHMDB
DG(16:1(9Z)/20:2(11Z,14Z)/0:0)Lipid Annotator
Chemical FormulaC39H70O5
Average Molecular Weight618.9701
Monoisotopic Molecular Weight618.52232535
IUPAC Name(2S)-1-[(9Z)-hexadec-9-enoyloxy]-3-hydroxypropan-2-yl (11Z,14Z)-icosa-11,14-dienoate
Traditional Namediacylglycerol
CAS Registry NumberNot Available
SMILES
[H]\C(CCCCCC)=C(/[H])CCCCCCCC(=O)OC[C@]([H])(CO)OC(=O)CCCCCCCCC\C([H])=C(\[H])C\C([H])=C(\[H])CCCCC
InChI Identifier
InChI=1S/C39H70O5/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/h11,13-14,16-18,37,40H,3-10,12,15,19-36H2,1-2H3/b13-11-,16-14-,18-17-/t37-/m0/s1
InChI KeyWPAJXHHVSWVZKN-YCGDJTGESA-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
logP10.05ALOGPS
logP12.7ChemAxon
logS-7.7ALOGPS
pKa (Strongest Acidic)14.58ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area72.83 ŲChemAxon
Rotatable Bond Count35ChemAxon
Refractivity189.45 m³·mol⁻¹ChemAxon
Polarizability80.02 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, Positivesplash10-00ac-5592327000-b9453ff95e17f11051c6View 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)/20:2(11Z,14Z)/0:0),1TMS,#1" TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000009000-8739cce7a1cf023acbb4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0i00-0009004000-e19a6a5e17867626228dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-02ti-0009004000-58fa630b548a1d45308fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000009000-16faae87ea495f60500aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0i00-0009004000-3824d8b2e87d4f7911f0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-02ti-0009004000-e7b4b627a1971e2b1a7fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0aor-2019003000-2a8463a4866cb89a35e4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0uk9-5095001000-96d0d0690fc13a1b8f5cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0zfr-3492000000-2d3b0c368a7ae9d85a7fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000009000-643d38840e80b534f39cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0000009000-643d38840e80b534f39cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001r-0009000000-5e2f6a1c08f5f178cd91View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-2049016000-9c0fa175b5effaab79e1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0296-3297001000-d72d05ba87053a41fedcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9521000000-294b227a06f89bd36863View 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 IDHMDB0007138
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB024332
KNApSAcK IDNot Available
Chemspider ID7822677
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9543727
PDB IDNot Available
ChEBI ID88496
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)/20:2(11Z,14Z)/0:0) → Cytidine monophosphate + PE(16:1(9Z)/20:2(11Z,14Z))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)/20:2(11Z,14Z)/0:0) + 5Z,8Z,11Z,14Z-eicosatetraenonyl-CoA → TG(16:1(9Z)/20:2n6/20:4(5Z,8Z,11Z,14Z)) + Coenzyme Adetails
DG(16:1(9Z)/20:2(11Z,14Z)/0:0) + Erucoyl-CoA → TG(16:1(9Z)/20:2n6/22:1(13Z)) + Coenzyme Adetails
DG(16:1(9Z)/20:2(11Z,14Z)/0:0) + Clupanodonyl CoA → TG(16:1(9Z)/20:2n6/22:5(7Z,10Z,13Z,16Z,19Z)) + Coenzyme Adetails