Showing metabocard for DG(18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/0:0) (BMDB0007201)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 23:32:36 UTC
Update Date2020-05-21 16:27:49 UTC
BMDB IDBMDB0007201
Secondary Accession Numbers
  • BMDB07201
Metabolite Identification
Common NameDG(18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/0:0)
DescriptionDG(18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/0:0), also known as dg(18:1(11z)/20:5(5z,8z,11z,14z,17z)/0:0) or DAG(18:1/20:5), belongs to the class of organic compounds known as 1,2-dg(18:1(11z)/20:5(5z,8z,11z,14z,17z)/0:0)s. These are dg(18:1(11z)/20:5(5z,8z,11z,14z,17z)/0:0)s containing a glycerol acylated at positions 1 and 2. DG(18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/0:0) is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). DG(18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/0:0) participates in a number of enzymatic reactions, within cattle. In particular, DG(18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/0:0) can be biosynthesized from PA(18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)); which is mediated by the enzyme phosphatidate phosphatase. Furthermore, DG(18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/0:0) and erucoyl-CoA can be converted into TG(18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z)); which is catalyzed by the enzyme dg(18:1(11z)/20:5(5z,8z,11z,14z,17z)/0:0) O-acyltransferase. Furthermore, DG(18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/0:0) can be biosynthesized from PA(18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)); which is mediated by the enzyme phosphatidate phosphatase. Furthermore, DG(18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/0:0) and nervonoyl-CoA can be converted into TG(18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z)); which is catalyzed by the enzyme dg(18:1(11z)/20:5(5z,8z,11z,14z,17z)/0:0) O-acyltransferase. Furthermore, DG(18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/0:0) can be biosynthesized from PA(18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)); which is catalyzed by the enzyme phosphatidate phosphatase. Finally, DG(18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/0:0) and docosanoyl-CoA can be converted into TG(18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:0); which is catalyzed by the enzyme dg(18:1(11z)/20:5(5z,8z,11z,14z,17z)/0:0) O-acyltransferase. In cattle, DG(18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/0:0) is involved in a few metabolic pathways, which include de novo triacylglycerol biosynthesis TG(18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z)) pathway, de novo triacylglycerol biosynthesis TG(18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z)) pathway, and de novo triacylglycerol biosynthesis TG(18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:0) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Vaccenoyl-2-eicosapentaenoyl-sn-glycerolHMDB
DAG(18:1/20:5)HMDB
DAG(18:1N7/20:5N3)HMDB
DAG(18:1W7/20:5W3)HMDB
DAG(38:6)HMDB
DG(18:1/20:5)HMDB
DG(18:1N7/20:5N3)HMDB
DG(18:1W7/20:5W3)HMDB
DG(38:6)HMDB
DiacylglycerolHMDB
Diacylglycerol(18:1/20:5)HMDB
Diacylglycerol(18:1n7/20:5n3)HMDB
Diacylglycerol(18:1W7/20:5W3)HMDB
Diacylglycerol(38:6)HMDB
DiglycerideHMDB
1-(11Z-Octadecenoyl)-2-(5Z,8Z,11Z,14Z,17Z-eicosapentaenoyl)-sn-glycerolHMDB
DG(18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/0:0)Lipid Annotator
Chemical FormulaC41H68O5
Average Molecular Weight640.9756
Monoisotopic Molecular Weight640.506675286
IUPAC Name(2S)-1-hydroxy-3-[(11Z)-octadec-11-enoyloxy]propan-2-yl (5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoate
Traditional Namediacylglycerol
CAS Registry NumberNot Available
SMILES
[H][C@](CO)(COC(=O)CCCCCCCCC\C=C/CCCCCC)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC
InChI Identifier
InChI=1S/C41H68O5/c1-3-5-7-9-11-13-15-17-19-20-22-24-26-28-30-32-34-36-41(44)46-39(37-42)38-45-40(43)35-33-31-29-27-25-23-21-18-16-14-12-10-8-6-4-2/h5,7,11,13-14,16-17,19,22,24,28,30,39,42H,3-4,6,8-10,12,15,18,20-21,23,25-27,29,31-38H2,1-2H3/b7-5-,13-11-,16-14-,19-17-,24-22-,30-28-/t39-/m0/s1
InChI KeyVOMWZIOQFOWIQI-MKRDPDFLSA-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
logP9.27ALOGPS
logP12.5ChemAxon
logS-7.6ALOGPS
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
Refractivity202 m³·mol⁻¹ChemAxon
Polarizability80.04 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 (Non-derivatized) - 70eV, Positivesplash10-0550-2294010000-a71b0e06db551a40ab18View in MoNA
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 GC-MSPredicted GC-MS Spectrum - GC-MS ("DG(18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/0:0),1TMS,#1" TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-059l-1098005000-be417c62cca509a970c6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kr-2094011000-1679660b7fff47b45e2dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kr-1092020000-1565a53d2c78b35653bcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01qi-0095003000-1a3d14f8f7c66b7db3c3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-1093000000-f02d93a6f7981d986b73View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-3092000000-f707b7204cb9d38d7247View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000009000-e8086b36c3df6f24dd64View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0000009000-e8086b36c3df6f24dd64View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03e9-0009000000-27d5b6d9dd04bde704a2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0045009000-243b8d2bbcd2cccc0e91View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01x0-4095001000-352d7b9ff867ce86a062View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0lz9-3192000000-b277fb3757b8806893acView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052o-3096068000-f0361a24f1ffe44c79bdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-2193000000-c4af0ab950db4f303735View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052r-1398000000-73f68ad26782c853eb57View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0000009000-0697d21e1d6f73bcdbfeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0abi-0009004000-362e41d13bed8df166c4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4r-0009004000-2a69aebf8acdb4bb73c9View 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 IDHMDB0007201
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB024395
KNApSAcK IDNot Available
Chemspider ID24765981
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53478076
PDB IDNot Available
ChEBI ID88547
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(18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/0:0) → Cytidine monophosphate + PE(18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))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(18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/0:0) + Erucoyl-CoA → TG(18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z)) + Coenzyme Adetails
DG(18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/0:0) + Clupanodonyl CoA → TG(18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z)) + Coenzyme Adetails