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Record Information
Version1.0
Creation Date2016-09-30 23:31:32 UTC
Update Date2020-05-21 16:27:45 UTC
BMDB IDBMDB0007148
Secondary Accession Numbers
  • BMDB07148
Metabolite Identification
Common NameDG(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/0:0)
DescriptionDG(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/0:0), also known as dg(16:1(9z)/22:5(4z,7z,10z,13z,16z)/0:0) or DAG(16:1/22:5), belongs to the class of organic compounds known as 1,2-dg(16:1(9z)/22:5(4z,7z,10z,13z,16z)/0:0)s. These are dg(16:1(9z)/22:5(4z,7z,10z,13z,16z)/0:0)s containing a glycerol acylated at positions 1 and 2. DG(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/0:0) is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). DG(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/0:0) participates in a number of enzymatic reactions, within cattle. In particular, DG(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/0:0) can be biosynthesized from PA(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)); which is catalyzed by the enzyme phosphatidate phosphatase. Furthermore, DG(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/0:0) and tetracosanoyl-CoA can be converted into TG(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:0); which is catalyzed by the enzyme dg(16:1(9z)/22:5(4z,7z,10z,13z,16z)/0:0) O-acyltransferase. Furthermore, DG(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/0:0) can be biosynthesized from PA(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)); which is mediated by the enzyme phosphatidate phosphatase. Finally, DG(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/0:0) and nervonoyl-CoA can be converted into TG(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z)) through its interaction with the enzyme dg(16:1(9z)/22:5(4z,7z,10z,13z,16z)/0:0) O-acyltransferase. In cattle, DG(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/0:0) is involved in a couple of metabolic pathways, which include de novo triacylglycerol biosynthesis TG(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:0) pathway and de novo triacylglycerol biosynthesis TG(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z)) pathway.
Structure
Thumb
Synonyms
ValueSource
1-Palmitoleoyl-2-docosapentaenoyl-sn-glycerolHMDB
1-Palmitoleoyl-2-osbondoyl-sn-glycerolHMDB
DAG(16:1/22:5)HMDB
DAG(16:1N7/22:5N6)HMDB
DAG(16:1W7/22:5W6)HMDB
DAG(38:6)HMDB
DG(16:1/22:5)HMDB
DG(16:1N7/22:5N6)HMDB
DG(16:1W7/22:5W6)HMDB
DG(38:6)HMDB
DiacylglycerolHMDB
Diacylglycerol(16:1/22:5)HMDB
Diacylglycerol(16:1n7/22:5n6)HMDB
Diacylglycerol(16:1W7/22:5W6)HMDB
Diacylglycerol(38:6)HMDB
DiglycerideHMDB
1-(9Z-Hexadecenoyl)-2-(4Z,7Z,10Z,13Z,16Z-docosapentaenoyl)-sn-glycerolHMDB
DG(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/0:0)Lipid Annotator
Chemical FormulaC41H68O5
Average Molecular Weight640.9756
Monoisotopic Molecular Weight640.506675286
IUPAC Name(2S)-1-[(9Z)-hexadec-9-enoyloxy]-3-hydroxypropan-2-yl (4Z,7Z,10Z,13Z,16Z)-docosa-4,7,10,13,16-pentaenoate
Traditional Namediacylglycerol
CAS Registry NumberNot Available
SMILES
[H][C@](CO)(COC(=O)CCCCCCC\C=C/CCCCCC)OC(=O)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCC
InChI Identifier
InChI=1S/C41H68O5/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-24-26-28-30-32-34-36-41(44)46-39(37-42)38-45-40(43)35-33-31-29-27-25-23-16-14-12-10-8-6-4-2/h11,13-14,16-18,20-21,24,26,30,32,39,42H,3-10,12,15,19,22-23,25,27-29,31,33-38H2,1-2H3/b13-11-,16-14-,18-17-,21-20-,26-24-,32-30-/t39-/m0/s1
InChI KeyGIZFOGBABDKCFB-STFOQGSXSA-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
logP9.29ALOGPS
logP12.5ChemAxon
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
Refractivity202 m³·mol⁻¹ChemAxon
Polarizability79.91 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01p9-2497150000-d4dcccefad48b5e2e050View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03du-1059004000-a9290f05a2b8b7c47609View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dr-3189031000-fa4980e10b53ff92b353View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06rj-1393140000-fbe05acf53a869bb35c4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f9i-0096003000-dcba734d9b907d8361c0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udr-1093000000-4a9ea59976467a8c025cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-1170-4095000000-fd962abb56f3f2527c6bView 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 IDHMDB0007148
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB024342
KNApSAcK IDNot Available
Chemspider ID24765947
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53478042
PDB IDNot Available
ChEBI ID88480
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

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)/22:5(4Z,7Z,10Z,13Z,16Z)/0:0) → Cytidine monophosphate + PE(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))details
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)/22:5(4Z,7Z,10Z,13Z,16Z)/0:0) + Clupanodonyl CoA → TG(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)) + Coenzyme Adetails