Showing metabocard for DG(16:0/20:4(5Z,8Z,11Z,14Z)/0:0) (BMDB0007112)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 23:30:49 UTC
Update Date2020-05-21 16:27:40 UTC
BMDB IDBMDB0007112
Secondary Accession Numbers
  • BMDB07112
Metabolite Identification
Common NameDG(16:0/20:4(5Z,8Z,11Z,14Z)/0:0)
DescriptionDG(16:0/20:4(5Z,8Z,11Z,14Z)/0:0)[iso2], also known as dg(16:0/20:4(5z,8z,11z,14z)/0:0)[iso2] or DAG(16:0/20:4), belongs to the class of organic compounds known as 1,2-dg(16:0/20:4(5z,8z,11z,14z)/0:0)[iso2]s. These are dg(16:0/20:4(5z,8z,11z,14z)/0:0)[iso2]s containing a glycerol acylated at positions 1 and 2. Thus, DG(16:0/20:4(5Z,8Z,11Z,14Z)/0:0)[iso2] is considered to be a diradylglycerol lipid molecule. DG(16:0/20:4(5Z,8Z,11Z,14Z)/0:0)[iso2] is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. In cattle, DG(16:0/20:4(5Z,8Z,11Z,14Z)/0:0)[iso2] is involved in the metabolic pathway called phosphatidylcholine biosynthesis PC(16:0/20:4(5Z,8Z,11Z,14Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(2S)-1-Hydroxy-3-(palmitoyloxy)propan-2-yl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoateChEBI
1,2-DG 16:0/20:4(omega-6)ChEBI
1-Hexadecanoyl-2-(5Z,8Z,11Z,14Z)-icosatetraenoyl-sn-glycerolChEBI
1-Hexadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycerolChEBI
DAG(16:0/20:4)ChEBI
DAG(16:0/20:4N6)ChEBI
DAG(16:0/20:4OMEGA6)ChEBI
DAG(36:4)ChEBI
DG(16:0/20:4)ChEBI
DG(16:0/20:4/0:0)ChEBI
DG(16:0/20:4N6)ChEBI
DG(16:0/20:4OMEGA6)ChEBI
DG(36:4)ChEBI
Diacylglycerol(16:0/20:4)ChEBI
Diacylglycerol(16:0/20:4n6)ChEBI
Diacylglycerol(16:0/20:4omega6)ChEBI
Diacylglycerol(36:4)ChEBI
(2S)-1-Hydroxy-3-(palmitoyloxy)propan-2-yl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoic acidGenerator
1-palmitoyl-2-arachidonoyl-sn-glycerolLipid Annotator, HMDB
DiglycerideLipid Annotator, HMDB
DiacylglycerolLipid Annotator, HMDB
DG(16:0/20:4(5Z,8Z,11Z,14Z)/0:0)Lipid Annotator, ChEBI
DAG(16:0/20:4W6)HMDB
DG(16:0/20:4W6)HMDB
Diacylglycerol(16:0/20:4W6)HMDB
Chemical FormulaC39H68O5
Average Molecular Weight616.9542
Monoisotopic Molecular Weight616.506675286
IUPAC Name(2S)-1-(hexadecanoyloxy)-3-hydroxypropan-2-yl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate
Traditional Namediacylglycerol
CAS Registry NumberNot Available
SMILES
[H][C@](CO)(COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC
InChI Identifier
InChI=1S/C39H68O5/c1-3-5-7-9-11-13-15-17-18-19-20-22-24-26-28-30-32-34-39(42)44-37(35-40)36-43-38(41)33-31-29-27-25-23-21-16-14-12-10-8-6-4-2/h11,13,17-18,20,22,26,28,37,40H,3-10,12,14-16,19,21,23-25,27,29-36H2,1-2H3/b13-11-,18-17-,22-20-,28-26-/t37-/m0/s1
InChI KeyYJEMDFYSDGNQNM-NDUZERMISA-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
logP9.87ALOGPS
logP12.33ChemAxon
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
Refractivity190.57 m³·mol⁻¹ChemAxon
Polarizability78.37 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, Positivesplash10-08fr-2294040000-498e441a36b002204a93View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0239-3291104000-1fb20d35f464ac4e22d8View in MoNA
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(16:0/20:4(5Z,8Z,11Z,14Z)/0:0),1TMS,#1" TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-029i-1097013000-40ffec7c7a41e5e798c8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01p9-2194010000-cf7e428413316b179287View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06rb-1392120000-338da90d2b4945981b01View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0pvr-0095002000-884dcf475214869aef63View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4r-1093000000-75690641d26a39c18115View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4r-3092000000-62466e5fe70c7688a4a6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-1036009000-2057148792b36d71e0ffView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-3092000000-7602d34e3b5eaa08ebbbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pbi-3193000000-465499b72a0d32f67da1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000009000-c5201b03fd289f8bd404View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0000009000-c5201b03fd289f8bd404View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0019-0009000000-8d0a014387d332757ec1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-3098155000-d524c939acacfea3c6dbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-4094020000-9e1b9f388cd59261721dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08i9-5479000000-172fc8842c760ef48a14View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000009000-7da2b68332eda96bc7ddView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0009031000-243fc8eba4c1c26b866aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-0009003000-9a6ab64d806f2a3dd83dView 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 IDHMDB0007112
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 Compound9543736
PDB IDNot Available
ChEBI ID77096
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(16:0/20:4(5Z,8Z,11Z,14Z)/0:0) → Cytidine monophosphate + PE(16:0/20:4(5Z,8Z,11Z,14Z))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(16:0/20:4(5Z,8Z,11Z,14Z)/0:0) + 5Z,8Z,11Z,14Z-eicosatetraenonyl-CoA → TG(16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) + Coenzyme Adetails
DG(16:0/20:4(5Z,8Z,11Z,14Z)/0:0) + Docosanoyl-CoA → TG(16:0/20:4(5Z,8Z,11Z,14Z)/22:0) + Coenzyme Adetails
DG(16:0/20:4(5Z,8Z,11Z,14Z)/0:0) + Erucoyl-CoA → TG(16:0/20:4(5Z,8Z,11Z,14Z)/22:1(13Z)) + Coenzyme Adetails
DG(16:0/20:4(5Z,8Z,11Z,14Z)/0:0) + Clupanodonyl CoA → TG(16:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)) + Coenzyme Adetails
DG(16:0/20:4(5Z,8Z,11Z,14Z)/0:0) + Tetracosanoyl-CoA → TG(16:0/20:4(5Z,8Z,11Z,14Z)/24:0) + Coenzyme Adetails