Showing metabocard for DG(18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z)/0:0) (BMDB0007350)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 23:35:35 UTC
Update Date2020-05-21 16:27:58 UTC
BMDB IDBMDB0007350
Secondary Accession Numbers
  • BMDB07350
Metabolite Identification
Common NameDG(18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z)/0:0)
DescriptionDG(18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z)/0:0)[iso2], also known as DG(18:4/22:4) or dg(18:4(6z,9z,12z,15z)/22:4(7z,10z,13z,16z)/0:0)[iso2], belongs to the class of organic compounds known as 1,2-dg(18:4(6z,9z,12z,15z)/22:4(7z,10z,13z,16z)/0:0)[iso2]s. These are dg(18:4(6z,9z,12z,15z)/22:4(7z,10z,13z,16z)/0:0)[iso2]s containing a glycerol acylated at positions 1 and 2. Thus, DG(18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z)/0:0)[iso2] is considered to be a diradylglycerol lipid molecule. DG(18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z)/0:0)[iso2] is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. In cattle, DG(18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z)/0:0)[iso2] is involved in a few metabolic pathways, which include de novo triacylglycerol biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)) pathway, de novo triacylglycerol biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) pathway, and phosphatidylethanolamine biosynthesis pe(18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Stearidonoyl-2-adrenoyl-sn-glycerolHMDB
DG(18:4/22:4)HMDB
Diacylglycerol(40:8)HMDB
DAG(18:4/22:4)HMDB
DiglycerideHMDB
DiacylglycerolHMDB
DG(40:8)HMDB
DAG(40:8)HMDB
1-(6Z,9Z,12Z,15Z-Octadecatetraenoyl)-2-(7Z,10Z,13Z,16Z-docosatetraenoyl)-sn-glycerolHMDB
Diacylglycerol(18:4/22:4)HMDB
DG(18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z)/0:0)Lipid Annotator
Chemical FormulaC43H68O5
Average Molecular Weight664.997
Monoisotopic Molecular Weight664.506675286
IUPAC Name(2S)-1-hydroxy-3-[(6Z,9Z,12Z,15Z)-octadeca-6,9,12,15-tetraenoyloxy]propan-2-yl (7Z,10Z,13Z,16Z)-docosa-7,10,13,16-tetraenoate
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)CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC
InChI Identifier
InChI=1S/C43H68O5/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/h6,8,11-14,17-19,21-23,26-29,41,44H,3-5,7,9-10,15-16,20,24-25,30-40H2,1-2H3/b8-6-,13-11-,14-12-,19-17-,22-21-,23-18-,28-26-,29-27-/t41-/m0/s1
InChI KeyZSNDBPNFIXXECQ-ONRVWSTQSA-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
logP8.63ALOGPS
logP12.66ChemAxon
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
Refractivity213.44 m³·mol⁻¹ChemAxon
Polarizability81.15 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 (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, Positivesplash10-001i-0000009000-2a0a38172b9871dac0eeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001s-0009004000-1f18c9f0dbb29f86dda4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001r-0009004000-7ebad27dfeaf5214bddeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-1066009000-32a34038f2f9bc1ce622View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05di-6097000000-465c27ba778fc3e8332dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a7i-7196000000-a96bad77e71fbff78493View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000009000-19764e10c451fc22ee44View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001s-0009004000-068941a5fa589a6c8f6cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001r-0009004000-8a4a225503bb52d6b386View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-1127079000-f2fa7796619ee2cbb6f4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-066r-3139010000-df1c4aceda5d323107cfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014r-1559030000-e52c0a88e72ccb9ee37eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000009000-b2e0515299b50695a3aeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0000009000-b2e0515299b50695a3aeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0bt9-0019701000-644471c623a80c822879View 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 IDHMDB0007350
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB024543
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53478179
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(18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z)/0:0) → Cytidine monophosphate + PE(18:4(6Z,9Z,12Z,15Z)/22:4(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(18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z)/0:0) + Clupanodonyl CoA → TG(18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)) + Coenzyme Adetails