Showing metabocard for DG(20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z)/0:0) (BMDB0007580)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 23:40:12 UTC
Update Date2020-05-21 16:28:05 UTC
BMDB IDBMDB0007580
Secondary Accession Numbers
  • BMDB07580
Metabolite Identification
Common NameDG(20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z)/0:0)
DescriptionDG(20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z)/0:0)[iso2], also known as DG(20:5/22:1) or dg(20:5(5z,8z,11z,14z,17z)/22:1(13z)/0:0)[iso2], belongs to the class of organic compounds known as 1,2-dg(20:5(5z,8z,11z,14z,17z)/22:1(13z)/0:0)[iso2]s. These are dg(20:5(5z,8z,11z,14z,17z)/22:1(13z)/0:0)[iso2]s containing a glycerol acylated at positions 1 and 2. Thus, DG(20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z)/0:0)[iso2] is considered to be a diradylglycerol lipid molecule. DG(20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z)/0:0)[iso2] is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. In cattle, DG(20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z)/0:0)[iso2] is involved in a few metabolic pathways, which include de novo triacylglycerol biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z)) pathway, de novo triacylglycerol biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) pathway, and phosphatidylethanolamine biosynthesis pe(20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
DG(42:6)HMDB
DG(20:5/22:1)HMDB
DiglycerideHMDB
Diacylglycerol(42:6)HMDB
DiacylglycerolHMDB
DAG(42:6)HMDB
Diacylglycerol(20:5/22:1)HMDB
DAG(20:5/22:1)HMDB
1-(5Z,8Z,11Z,14Z,17Z-Eicosapentaenoyl)-2-(13Z-docosenoyl)-sn-glycerolHMDB
1-Eicosapentaenoyl-2-erucoyl-sn-glycerolHMDB
DG(20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z)/0:0)Lipid Annotator
Chemical FormulaC45H76O5
Average Molecular Weight697.0819
Monoisotopic Molecular Weight696.569275542
IUPAC Name(2S)-1-hydroxy-3-[(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoyloxy]propan-2-yl (13Z)-docos-13-enoate
Traditional Namediacylglycerol
CAS Registry NumberNot Available
SMILES
[H][C@](CO)(COC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC)OC(=O)CCCCCCCCCCC\C=C/CCCCCCCC
InChI Identifier
InChI=1S/C45H76O5/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/h6,8,12,14,17-20,25,27,31,33,43,46H,3-5,7,9-11,13,15-16,21-24,26,28-30,32,34-42H2,1-2H3/b8-6-,14-12-,19-17-,20-18-,27-25-,33-31-/t43-/m0/s1
InChI KeyRBNQMECWIQORFH-ONNHQCRXSA-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
logP10.1ALOGPS
logP14.28ChemAxon
logS-7.9ALOGPS
pKa (Strongest Acidic)14.58ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area72.83 ŲChemAxon
Rotatable Bond Count38ChemAxon
Refractivity220.41 m³·mol⁻¹ChemAxon
Polarizability88.04 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-0000000900-4d1a8fb2902d0b1a9641View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-054k-0009003000-987ade475b72dc7277a2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06r2-0009001300-1f65e7146c455cc84344View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0000000900-8a1c6226c0719bd2dacdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0000000900-8a1c6226c0719bd2dacdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0159-0009600100-f62dea66e5281281d9a7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000000900-0e123f184b57ffebfcd6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-054k-0009003000-b3518babc2020b8d0a3eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06r2-0009001300-f76a286c9224a5eedd92View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0019008000-ddd24e09ec35842e250eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fk9-4019000000-20bbce309009f189684fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f79-4049000000-7a5fb4f341ba1db8d260View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-006t-2009057000-07632e58d741b43e6c68View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-2019011000-67144c6b9a900db6abdbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05gi-5859010000-f784fe8134112902c132View 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 IDHMDB0007580
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 Compound9543917
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(20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z)/0:0) → Cytidine monophosphate + PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))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(20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z)/0:0) + Clupanodonyl CoA → TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z)) + Coenzyme Adetails