Showing metabocard for DG(20:5(5Z,8Z,11Z,14Z,17Z)/22:0/0:0) (BMDB0007579)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 23:40:11 UTC
Update Date2020-05-21 16:28:05 UTC
BMDB IDBMDB0007579
Secondary Accession Numbers
  • BMDB07579
Metabolite Identification
Common NameDG(20:5(5Z,8Z,11Z,14Z,17Z)/22:0/0:0)
DescriptionDG(20:5(5Z,8Z,11Z,14Z,17Z)/22:0/0:0)[iso2], also known as dg(20:5(5z,8z,11z,14z,17z)/22:0/0:0)[iso2] or DAG(20:5/22:0), belongs to the class of organic compounds known as 1,2-dg(20:5(5z,8z,11z,14z,17z)/22:0/0:0)[iso2]s. These are dg(20:5(5z,8z,11z,14z,17z)/22:0/0:0)[iso2]s containing a glycerol acylated at positions 1 and 2. Thus, DG(20:5(5Z,8Z,11Z,14Z,17Z)/22:0/0:0)[iso2] is considered to be a diradylglycerol lipid molecule. DG(20:5(5Z,8Z,11Z,14Z,17Z)/22:0/0:0)[iso2] is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. In cattle, DG(20:5(5Z,8Z,11Z,14Z,17Z)/22:0/0:0)[iso2] is involved in a couple of metabolic pathways, which include de novo triacylglycerol biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:0/22:0) pathway and de novo triacylglycerol biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:0/24:0) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Diacylglycerol(42:5)HMDB
DiglycerideHMDB
DAG(20:5/22:0)HMDB
1-Eicosapentaenoyl-2-behenoyl-sn-glycerolHMDB
DAG(42:5)HMDB
DiacylglycerolHMDB
DG(20:5/22:0)HMDB
Diacylglycerol(20:5/22:0)HMDB
1-(5Z,8Z,11Z,14Z,17Z-Eicosapentaenoyl)-2-docosanoyl-sn-glycerolHMDB
DG(42:5)HMDB
DG(20:5(5Z,8Z,11Z,14Z,17Z)/22:0/0:0)Lipid Annotator
Chemical FormulaC45H78O5
Average Molecular Weight699.0978
Monoisotopic Molecular Weight698.584925606
IUPAC Name(2S)-1-hydroxy-3-[(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoyloxy]propan-2-yl docosanoate
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)CCCCCCCCCCCCCCCCCCCCC
InChI Identifier
InChI=1S/C45H78O5/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/h6,8,12,14,18,20,25,27,31,33,43,46H,3-5,7,9-11,13,15-17,19,21-24,26,28-30,32,34-42H2,1-2H3/b8-6-,14-12-,20-18-,27-25-,33-31-/t43-/m0/s1
InChI KeyDKGGGFRIGQZDAN-FEXBNKBVSA-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
logP10.45ALOGPS
logP14.64ChemAxon
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 Count39ChemAxon
Refractivity219.29 m³·mol⁻¹ChemAxon
Polarizability90.3 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, Positivesplash10-014i-0000000900-106fba633af2f7bac685View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0532-0009003000-6d7bd1a76c7b85996b0aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05mk-0009001300-3246d105a964d886616aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-006t-3009047000-d8c549cd3be60051885dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-3019021000-5246bb198216befb3471View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00yi-7669000000-67a9a8a0111c7e0ba842View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0000000900-9de81be7e33732c423a4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0532-0009003000-31b0b6aa8c001b0cb1a2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05mk-0009001300-a6ce83b7f597287262d6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-1019008000-917196ee9bb7f62b0d7fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00dr-3019001000-c46f2c072ad164409107View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udr-3039000000-b3cc07c5c39a392a2102View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0000000900-05421be3ec5289cbf5d9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0000000900-05421be3ec5289cbf5d9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0160-0009600100-86a5b1af85e12bf9a565View 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 IDHMDB0007579
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 Compound9543909
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)/22:0/0:0) → Cytidine monophosphate + PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:0)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)/22:0/0:0) + Clupanodonyl CoA → TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:0/22:5(7Z,10Z,13Z,16Z,19Z)) + Coenzyme Adetails