Showing metabocard for DG(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/0:0) (BMDB0007141)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 23:31:24 UTC
Update Date2020-05-21 16:27:44 UTC
BMDB IDBMDB0007141
Secondary Accession Numbers
  • BMDB07141
Metabolite Identification
Common NameDG(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/0:0)
DescriptionDG(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/0:0)[iso2], also known as DG(16:1/20:4) or dg(16:1(9z)/20:4(5z,8z,11z,14z)/0:0)[iso2], belongs to the class of organic compounds known as 1,2-dg(16:1(9z)/20:4(5z,8z,11z,14z)/0:0)[iso2]s. These are dg(16:1(9z)/20:4(5z,8z,11z,14z)/0:0)[iso2]s containing a glycerol acylated at positions 1 and 2. Thus, DG(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/0:0)[iso2] is considered to be a diradylglycerol lipid molecule. DG(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/0:0)[iso2] is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. In cattle, DG(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/0:0)[iso2] is involved in the metabolic pathway called de novo triacylglycerol biosynthesis TG(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
DG(16:1/20:4)Lipid Annotator, HMDB
DG(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/0:0)Lipid Annotator
Diacylglycerol(16:1/20:4)Lipid Annotator, HMDB
DiglycerideLipid Annotator, HMDB
DG(36:5)Lipid Annotator, HMDB
Diacylglycerol(36:5)Lipid Annotator, HMDB
DAG(36:5)Lipid Annotator, HMDB
DiacylglycerolLipid Annotator, HMDB
1-palmitoleoyl-2-arachidonoyl-sn-glycerolLipid Annotator, HMDB
1-(9Z-hexadecenoyl)-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycerolLipid Annotator, HMDB
DAG(16:1/20:4)Lipid Annotator, HMDB
Chemical FormulaC39H66O5
Average Molecular Weight614.9383
Monoisotopic Molecular Weight614.491025222
IUPAC Name(2S)-1-[(9Z)-hexadec-9-enoyloxy]-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)CCCCCCC\C=C/CCCCCC)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC
InChI Identifier
InChI=1S/C39H66O5/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/h11,13-14,16-18,20,22,26,28,37,40H,3-10,12,15,19,21,23-25,27,29-36H2,1-2H3/b13-11-,16-14-,18-17-,22-20-,28-26-/t37-/m0/s1
InChI KeyIVRNQYIPGILFPZ-SEKRGLSRSA-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
logP9.32ALOGPS
logP11.97ChemAxon
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 Count33ChemAxon
Refractivity191.69 m³·mol⁻¹ChemAxon
Polarizability76.96 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, Positivesplash10-0bt9-1394140000-2fa6b56dd7f7dd3ced25View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-05a9-4392205000-bb3cd75ce60567f0d056View 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(16:1(9Z)/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-d38c878bc4c463b85113View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01p9-1094020000-2870bb1091bd5312caa7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4s-1291220000-e94bec41b99fb632b1a1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udr-0095002000-2f0943e075870390f59eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udr-1093000000-398f8a4e260387a76685View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udr-3092000000-3fa02ae98c25e68c7f19View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000009000-76503681101bfbcc5bcfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0009031000-1caa76e48da7395e78d8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-0009003000-3b678ba302b23e136bc3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000009000-c292a667c0eda7d86f41View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0000009000-c292a667c0eda7d86f41View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-0009000000-ace8d150dd810d6267f6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ik9-1046009000-640937efd70b8fda5610View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udr-4093000000-ba8a88efdf19f9c601e3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udr-5193000000-2f6f9162afbc255663d3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-2296165000-f82c75d38fc79be95934View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052r-3294010000-076fd2f92d953d10345aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06ri-4596000000-26706eb0b508755a6cf2View 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 IDHMDB0007141
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID7822693
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9543743
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(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/0:0) → Cytidine monophosphate + PE(16:1(9Z)/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(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/0:0) + 5Z,8Z,11Z,14Z-eicosatetraenonyl-CoA → TG(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) + Coenzyme Adetails
DG(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/0:0) + Erucoyl-CoA → TG(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:1(13Z)) + Coenzyme Adetails
DG(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/0:0) + Clupanodonyl CoA → TG(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)) + Coenzyme Adetails