Showing metabocard for DG(18:4(6Z,9Z,12Z,15Z)/22:0/0:0) (BMDB0007347)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 23:35:31 UTC
Update Date2020-05-21 16:27:58 UTC
BMDB IDBMDB0007347
Secondary Accession Numbers
  • BMDB07347
Metabolite Identification
Common NameDG(18:4(6Z,9Z,12Z,15Z)/22:0/0:0)
DescriptionDG(18:4(6Z,9Z,12Z,15Z)/22:0/0:0)[iso2], also known as dg(18:4(6z,9z,12z,15z)/22:0/0:0)[iso2] or DAG(18:4/22:0), belongs to the class of organic compounds known as 1,2-dg(18:4(6z,9z,12z,15z)/22:0/0:0)[iso2]s. These are dg(18:4(6z,9z,12z,15z)/22:0/0:0)[iso2]s containing a glycerol acylated at positions 1 and 2. Thus, DG(18:4(6Z,9Z,12Z,15Z)/22:0/0:0)[iso2] is considered to be a diradylglycerol lipid molecule. DG(18:4(6Z,9Z,12Z,15Z)/22:0/0:0)[iso2] is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. In cattle, DG(18:4(6Z,9Z,12Z,15Z)/22:0/0:0)[iso2] is involved in a couple of metabolic pathways, which include de novo triacylglycerol biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:0/22:1(13Z)) pathway and de novo triacylglycerol biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:0/24:1(15Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Stearidonoyl-2-behenoyl-sn-glycerolHMDB
DAG(18:4/22:0)HMDB
DAG(18:4N3/22:0)HMDB
DAG(18:4W3/22:0)HMDB
DAG(40:4)HMDB
DG(18:4/22:0)HMDB
DG(18:4N3/22:0)HMDB
DG(18:4W3/22:0)HMDB
DG(40:4)HMDB
DiacylglycerolHMDB
Diacylglycerol(18:4/22:0)HMDB
Diacylglycerol(18:4n3/22:0)HMDB
Diacylglycerol(18:4W3/22:0)HMDB
Diacylglycerol(40:4)HMDB
DiglycerideHMDB
1-(6Z,9Z,12Z,15Z-Octadecatetraenoyl)-2-docosanoyl-sn-glycerolHMDB
DG(18:4(6Z,9Z,12Z,15Z)/22:0/0:0)Lipid Annotator
Chemical FormulaC43H76O5
Average Molecular Weight673.0605
Monoisotopic Molecular Weight672.569275542
IUPAC Name(2S)-1-hydroxy-3-[(6Z,9Z,12Z,15Z)-octadeca-6,9,12,15-tetraenoyloxy]propan-2-yl docosanoate
Traditional Namediacylglycerol
CAS Registry NumberNot Available
SMILES
[H][C@](CO)(COC(=O)CCCC\C=C/C\C=C/C\C=C/C\C=C/CC)OC(=O)CCCCCCCCCCCCCCCCCCCCC
InChI Identifier
InChI=1S/C43H76O5/c1-3-5-7-9-11-13-15-17-19-20-21-22-24-26-28-30-32-34-36-38-43(46)48-41(39-44)40-47-42(45)37-35-33-31-29-27-25-23-18-16-14-12-10-8-6-4-2/h6,8,12,14,18,23,27,29,41,44H,3-5,7,9-11,13,15-17,19-22,24-26,28,30-40H2,1-2H3/b8-6-,14-12-,23-18-,29-27-/t41-/m0/s1
InChI KeyGIMCDLCIXKQLOR-NPZKRYRUSA-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
logP10.44ALOGPS
logP14.11ChemAxon
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 Count38ChemAxon
Refractivity208.97 m³·mol⁻¹ChemAxon
Polarizability87.15 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, Positivesplash10-001s-4497001000-01c47ba7679dca273208View 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 LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05fr-1039003000-9ffdf0618755a3f559bcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05aj-3079001000-c8361a5fe7fa169f001eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ars-1093011000-a5fdb35188f82dd09f60View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-05dr-0096003000-8371f0c06ca8390de513View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056r-1093000000-fe9ef867cb8504ec3e33View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0570-4095000000-7e715a03954c321a1a7bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0000009000-d45cdcefb72f30be67fcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0000009000-d45cdcefb72f30be67fcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0b90-0019701000-f00d62ef00e176fe979eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-2009054000-3cb1ef5d37b54f8f3427View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05fr-4019010000-22423397c94002854d78View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05gj-9555010000-c8a12c7a7ab9f47c87b8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-1036009000-024d74f63915f01b4160View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00g0-4049001000-d61f882d8e9969c85648View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-4095000000-74fd290f1746cc21e961View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000009000-7879d85c13086e66b079View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-053t-0009004000-48045bb27a0ad1e58860View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001n-0009004000-fe3a6536c463b6966c72View 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 IDHMDB0007347
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB024540
KNApSAcK IDNot Available
Chemspider ID24766084
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53478176
PDB IDNot Available
ChEBI ID88975
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(18:4(6Z,9Z,12Z,15Z)/22:0/0:0) → Cytidine monophosphate + PE(18:4(6Z,9Z,12Z,15Z)/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(18:4(6Z,9Z,12Z,15Z)/22:0/0:0) + Clupanodonyl CoA → TG(18:4(6Z,9Z,12Z,15Z)/22:0/22:5(7Z,10Z,13Z,16Z,19Z)) + Coenzyme Adetails