Showing metabocard for DG(20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z)/0:0) (BMDB0007524)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 23:39:05 UTC
Update Date2020-05-21 16:28:04 UTC
BMDB IDBMDB0007524
Secondary Accession Numbers
  • BMDB07524
Metabolite Identification
Common NameDG(20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z)/0:0)
DescriptionDG(20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z)/0:0)[iso2], also known as dg(20:4(5z,8z,11z,14z)/22:4(7z,10z,13z,16z)/0:0)[iso2] or DG(20:4/22:4), belongs to the class of organic compounds known as 1,2-dg(20:4(5z,8z,11z,14z)/22:4(7z,10z,13z,16z)/0:0)[iso2]s. These are dg(20:4(5z,8z,11z,14z)/22:4(7z,10z,13z,16z)/0:0)[iso2]s containing a glycerol acylated at positions 1 and 2. Thus, DG(20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z)/0:0)[iso2] is considered to be a diradylglycerol lipid molecule. DG(20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z)/0:0)[iso2] is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. In cattle, DG(20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z)/0:0)[iso2] is involved in a couple of metabolic pathways, which include de novo triacylglycerol biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) pathway and phosphatidylethanolamine biosynthesis pe(20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
DiglycerideHMDB
Diacylglycerol(42:8)HMDB
DG(42:8)HMDB
1-Arachidonoyl-2-adrenoyl-sn-glycerolHMDB
DAG(42:8)HMDB
DG(20:4/22:4)HMDB
DiacylglycerolHMDB
Diacylglycerol(20:4/22:4)HMDB
1-(5Z,8Z,11Z,14Z-Eicosatetraenoyl)-2-(7Z,10Z,13Z,16Z-docosatetraenoyl)-sn-glycerolHMDB
DAG(20:4/22:4)HMDB
DG(20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z)/0:0)Lipid Annotator
Chemical FormulaC45H72O5
Average Molecular Weight693.0502
Monoisotopic Molecular Weight692.537975414
IUPAC Name(2S)-1-hydroxy-3-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]propan-2-yl (7Z,10Z,13Z,16Z)-docosa-7,10,13,16-tetraenoate
Traditional Namediacylglycerol
CAS Registry NumberNot Available
SMILES
[H][C@](CO)(COC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC)OC(=O)CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC
InChI Identifier
InChI=1S/C45H72O5/c1-3-5-7-9-11-13-15-17-19-21-22-24-26-28-30-32-34-36-38-40-45(48)50-43(41-46)42-49-44(47)39-37-35-33-31-29-27-25-23-20-18-16-14-12-10-8-6-4-2/h11-14,17-20,22,24-25,27-28,30-31,33,43,46H,3-10,15-16,21,23,26,29,32,34-42H2,1-2H3/b13-11-,14-12-,19-17-,20-18-,24-22-,27-25-,30-28-,33-31-/t43-/m0/s1
InChI KeyQLXRTSJYSJPTKX-HZCZZQGESA-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
logP9.01ALOGPS
logP13.55ChemAxon
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 Count36ChemAxon
Refractivity222.64 m³·mol⁻¹ChemAxon
Polarizability85.27 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, Positivesplash10-03di-0000000900-d1a79b8e5ecc54c92140View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03g0-0009003000-c381cf9c3ffbabdbb8d9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dr-0009001300-34e6c8ab9028692b30f3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00mo-4026029000-eeed2af475c2bd19518eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014r-2049011000-76b13d54f8c84423ef40View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014r-0459010000-f1b24ac149a80cac0241View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0019007000-28e6e4ffa1bf5282bd68View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0uk9-4019000000-27582cb70b2668c013aaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0zgr-5129000000-7108eed09cca4ad0f3f9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000000900-d218cf24b737f2cfc7baView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03g0-0009003000-f038f8c159eca085b819View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dr-0009001300-c1a71807b684b5336288View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0000000900-2c88940c120b6ce9d2f7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0000000900-2c88940c120b6ce9d2f7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03f0-0009600100-56239e179fc2df3ebf1dView 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 IDHMDB0007524
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9543933
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(20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z)/0:0) → Cytidine monophosphate + PE(20:4(5Z,8Z,11Z,14Z)/22:4(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(20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z)/0:0) + Clupanodonyl CoA → TG(20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)) + Coenzyme Adetails