Showing metabocard for DG(22:0/22:5(4Z,7Z,10Z,13Z,16Z)/0:0) (BMDB0007612)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 23:40:51 UTC
Update Date2020-05-21 16:28:06 UTC
BMDB IDBMDB0007612
Secondary Accession Numbers
  • BMDB07612
Metabolite Identification
Common NameDG(22:0/22:5(4Z,7Z,10Z,13Z,16Z)/0:0)
DescriptionDG(22:0/22:5(4Z,7Z,10Z,13Z,16Z)/0:0), also known as dg(22:0/22:5(4z,7z,10z,13z,16z)/0:0) or DAG(22:0/22:5), belongs to the class of organic compounds known as 1,2-dg(22:0/22:5(4z,7z,10z,13z,16z)/0:0)s. These are dg(22:0/22:5(4z,7z,10z,13z,16z)/0:0)s containing a glycerol acylated at positions 1 and 2. DG(22:0/22:5(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(22:0/22:5(4Z,7Z,10Z,13Z,16Z)/0:0) participates in a number of enzymatic reactions, within cattle. In particular, DG(22:0/22:5(4Z,7Z,10Z,13Z,16Z)/0:0) can be biosynthesized from PA(22:0/22:5(4Z,7Z,10Z,13Z,16Z)) through its interaction with the enzyme phosphatidate phosphatase. In addition, DG(22:0/22:5(4Z,7Z,10Z,13Z,16Z)/0:0) and docosahexaenoyl-CoA can be converted into TG(22:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)); which is catalyzed by the enzyme dg(22:0/22:5(4z,7z,10z,13z,16z)/0:0) O-acyltransferase. In cattle, DG(22:0/22:5(4Z,7Z,10Z,13Z,16Z)/0:0) is involved in the metabolic pathway called de novo triacylglycerol biosynthesis TG(22:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Behenoyl-2-docosapentaenoyl-sn-glycerolHMDB
1-Behenoyl-2-osbondoyl-sn-glycerolHMDB
DAG(22:0/22:5)HMDB
DAG(22:0/22:5N6)HMDB
DAG(22:0/22:5W6)HMDB
DAG(44:5)HMDB
DG(22:0/22:5)HMDB
DG(22:0/22:5N6)HMDB
DG(22:0/22:5W6)HMDB
DG(44:5)HMDB
DiacylglycerolHMDB
Diacylglycerol(22:0/22:5)HMDB
Diacylglycerol(22:0/22:5n6)HMDB
Diacylglycerol(22:0/22:5W6)HMDB
Diacylglycerol(44:5)HMDB
DiglycerideHMDB
1-Docosanoyl-2-(4Z,7Z,10Z,13Z,16Z-docosapentaenoyl)-sn-glycerolHMDB
DG(22:0/22:5(4Z,7Z,10Z,13Z,16Z)/0:0)Lipid Annotator
Chemical FormulaC47H82O5
Average Molecular Weight727.151
Monoisotopic Molecular Weight726.616225734
IUPAC Name(2S)-1-(docosanoyloxy)-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)CCCCCCCCCCCCCCCCCCCCC)OC(=O)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCC
InChI Identifier
InChI=1S/C47H82O5/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-35-37-39-41-46(49)51-44-45(43-48)52-47(50)42-40-38-36-34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h12,14,18,20,24,26,30,32,36,38,45,48H,3-11,13,15-17,19,21-23,25,27-29,31,33-35,37,39-44H2,1-2H3/b14-12-,20-18-,26-24-,32-30-,38-36-/t45-/m0/s1
InChI KeyKACLHCRWXDJTBX-AKMAWJOXSA-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
logP10.67ALOGPS
logP15.53ChemAxon
logS-7.8ALOGPS
pKa (Strongest Acidic)14.58ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area72.83 ŲChemAxon
Rotatable Bond Count41ChemAxon
Refractivity228.49 m³·mol⁻¹ChemAxon
Polarizability94.34 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 (TMS_1_1) - 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, Positivesplash10-0006-0000000900-aa684ea5cc6c399a8aa0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052t-0009000400-42957b98a830ca32e665View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000n-0009000400-e8ffcb339745b5db1122View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-1005200900-5d534e277b512e269ec4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0079-2009000000-8d951d67271b1d603559View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05g0-2009000000-5b87d75937c1e07ff9bfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-06vr-0019000400-f5e86f49057212419815View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03k9-0019000000-1b0cb236c4edd5e26641View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-1119000000-45ca3ac39af899ced313View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0000000900-b2fdc7efe6f34978ef3bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0000000900-b2fdc7efe6f34978ef3bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0b90-0001900000-77667ca63df3118aa3e5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000000900-b0329d2fbde3d7843971View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052t-0009000400-921f909ce0db66dc0d3bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000n-0009000400-d47efd18407ac19f6e84View 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 IDHMDB0007612
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB024805
KNApSAcK IDNot Available
Chemspider ID24766287
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53478379
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(22:0/22:5(4Z,7Z,10Z,13Z,16Z)/0:0) → Cytidine monophosphate + PE(22:0/22:5(4Z,7Z,10Z,13Z,16Z))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(22:0/22:5(4Z,7Z,10Z,13Z,16Z)/0:0) + Clupanodonyl CoA → TG(22:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)) + Coenzyme Adetails
DG(22:0/22:5(4Z,7Z,10Z,13Z,16Z)/0:0) + Tetracosanoyl-CoA → TG(22:0/22:5(4Z,7Z,10Z,13Z,16Z)/24:0) + Coenzyme Adetails