Showing metabocard for DG(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)/0:0) (BMDB0007583)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 23:40:15 UTC
Update Date2020-05-21 16:28:05 UTC
BMDB IDBMDB0007583
Secondary Accession Numbers
  • BMDB07583
Metabolite Identification
Common NameDG(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)/0:0)
DescriptionDG(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)/0:0), also known as DAG(20:5/22:5) or dg(20:5(5z,8z,11z,14z,17z)/22:5(4z,7z,10z,13z,16z)/0:0), belongs to the class of organic compounds known as 1,2-dg(20:5(5z,8z,11z,14z,17z)/22:5(4z,7z,10z,13z,16z)/0:0)s. These are dg(20:5(5z,8z,11z,14z,17z)/22:5(4z,7z,10z,13z,16z)/0:0)s containing a glycerol acylated at positions 1 and 2. DG(20:5(5Z,8Z,11Z,14Z,17Z)/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(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)/0:0) participates in a number of enzymatic reactions, within cattle. In particular, DG(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)/0:0) can be biosynthesized from PA(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)) through the action of the enzyme phosphatidate phosphatase. Furthermore, DG(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)/0:0) and clupanodonoyl-CoA can be converted into TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)) through the action of the enzyme dg(20:5(5z,8z,11z,14z,17z)/22:5(4z,7z,10z,13z,16z)/0:0) O-acyltransferase. Furthermore, DG(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)/0:0) can be biosynthesized from PA(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)) through its interaction with the enzyme phosphatidate phosphatase. Furthermore, DG(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)/0:0) and tetracosanoyl-CoA can be converted into TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:0); which is catalyzed by the enzyme dg(20:5(5z,8z,11z,14z,17z)/22:5(4z,7z,10z,13z,16z)/0:0) O-acyltransferase. Finally, CDP-Ethanolamine and DG(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)/0:0) can be converted into cytidine monophosphate and PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)); which is catalyzed by the enzyme choline/ethanolaminephosphotransferase. In cattle, DG(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)/0:0) is involved in several metabolic pathways, some of which include de novo triacylglycerol biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)) pathway, de novo triacylglycerol biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:0) pathway, phosphatidylethanolamine biosynthesis pe(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)) pathway, and de novo triacylglycerol biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
DiglycerideHMDB
DAG(20:5/22:5)HMDB
1-Eicosapentaenoyl-2-osbondoyl-sn-glycerolHMDB
Diacylglycerol(42:10)HMDB
Diacylglycerol(20:5/22:5)HMDB
DAG(42:10)HMDB
DG(42:10)HMDB
DiacylglycerolHMDB
1-(5Z,8Z,11Z,14Z,17Z-Eicosapentaenoyl)-2-(4Z,7Z,10Z,13Z,16Z-docosapentaenoyl)-sn-glycerolHMDB
DG(20:5/22:5)HMDB
DG(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)/0:0)Lipid Annotator
Chemical FormulaC45H68O5
Average Molecular Weight689.0184
Monoisotopic Molecular Weight688.506675286
IUPAC Name(2S)-1-hydroxy-3-[(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoyloxy]propan-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)CCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC)OC(=O)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCC
InChI Identifier
InChI=1S/C45H68O5/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/h6,8,11-14,17-20,22,24-25,27-28,30-31,33-34,36,43,46H,3-5,7,9-10,15-16,21,23,26,29,32,35,37-42H2,1-2H3/b8-6-,13-11-,14-12-,19-17-,20-18-,24-22-,27-25-,30-28-,33-31-,36-34-/t43-/m0/s1
InChI KeySTFDXSFZJYFVLD-WKAQRXBLSA-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
logP8.45ALOGPS
logP12.83ChemAxon
logS-7.5ALOGPS
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
Refractivity224.87 m³·mol⁻¹ChemAxon
Polarizability83.01 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, Positivesplash10-0a4i-0000000900-4d54919a524ef91c6f8fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0abr-0009003000-56cfcd32236dfd1dbe88View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4r-0009001300-b09726c88490dc2fce64View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0015029000-02913d34eb76f6d0704aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-1029011000-470cb4615937ca636158View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08gr-0269010000-586d2aa51b8d0d3c6434View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000000900-4f89aa3e58d4acf53579View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0000000900-4f89aa3e58d4acf53579View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a60-0009600100-97360fd2a6b0b171b4a0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0029007000-17aca4fcf2c168d85132View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0uk9-4029000000-288951bd01f7f563c9aaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0kdi-5169000000-b8b882cbe5910c124caaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0000000900-e9c6fca1c39c4d12b999View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0abr-0009003000-166ecb511617acdd793aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4r-0009001300-03c5dab1eb4c3e2ecbf4View 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 IDHMDB0007583
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 Compound53478356
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)/22:5(4Z,7Z,10Z,13Z,16Z)/0:0) → Cytidine monophosphate + PE(20:5(5Z,8Z,11Z,14Z,17Z)/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(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)/0:0) + Clupanodonyl CoA → TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)) + Coenzyme Adetails