Showing metabocard for DG(18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z)/0:0) (BMDB0007321)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 23:35:00 UTC
Update Date2020-05-21 16:27:57 UTC
BMDB IDBMDB0007321
Secondary Accession Numbers
  • BMDB07321
Metabolite Identification
Common NameDG(18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z)/0:0)
DescriptionDG(18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z)/0:0)[iso2], also known as dg(18:3(9z,12z,15z)/22:4(7z,10z,13z,16z)/0:0)[iso2] or DG(18:3/22:4), belongs to the class of organic compounds known as 1,2-dg(18:3(9z,12z,15z)/22:4(7z,10z,13z,16z)/0:0)[iso2]s. These are dg(18:3(9z,12z,15z)/22:4(7z,10z,13z,16z)/0:0)[iso2]s containing a glycerol acylated at positions 1 and 2. Thus, DG(18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z)/0:0)[iso2] is considered to be a diradylglycerol lipid molecule. DG(18:3(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(18:3(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(18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)) pathway, de novo triacylglycerol biosynthesis TG(18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z)/24:0) pathway, and phosphatidylethanolamine biosynthesis pe(18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
DG(18:3/22:4)HMDB
DAG(18:3/22:4)HMDB
DAG(40:7)HMDB
DiglycerideHMDB
DG(40:7)HMDB
1-a-Linolenoyl-2-adrenoyl-sn-glycerolHMDB
DiacylglycerolHMDB
Diacylglycerol(18:3/22:4)HMDB
1-(9Z,12Z,15Z-Octadeatrienoyl)-2-(7Z,10Z,13Z,16Z-docosatetraenoyl)-sn-glycerolHMDB
Diacylglycerol(40:7)HMDB
DG(18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z)/0:0)Lipid Annotator
Chemical FormulaC43H70O5
Average Molecular Weight667.0129
Monoisotopic Molecular Weight666.52232535
IUPAC Name(2S)-1-hydroxy-3-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]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)CCCCCCC\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/C43H70O5/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/h6,8,11-14,17-19,21-23,26,28,41,44H,3-5,7,9-10,15-16,20,24-25,27,29-40H2,1-2H3/b8-6-,13-11-,14-12-,19-17-,22-21-,23-18-,28-26-/t41-/m0/s1
InChI KeyGDGIKICQQQMUCS-BQSGGISSSA-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
logP9.07ALOGPS
logP13.03ChemAxon
logS-7.7ALOGPS
pKa (Strongest Acidic)14.58ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area72.83 ŲChemAxon
Rotatable Bond Count35ChemAxon
Refractivity212.32 m³·mol⁻¹ChemAxon
Polarizability82.4 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, Positivesplash10-0019-3398222000-c65c81edb7b6f6ad9225View 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, Positivesplash10-014r-1049004000-d10bd5030f3dcea410e4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02tj-2089121000-0b9d557b10468cd6198fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014r-1093120000-ec6fa136f5327f714c65View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-05q9-0096003000-5fba5dcb87e2780810a3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056r-1093000000-75b113275958e9977f40View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06w9-4095000000-8c885ca38640d83942eeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000009000-64b93739ea49f5c060aaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0009004000-6b57342bab6142a746f6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0009004000-bcb1f04ed145b6fd2efbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-3228098000-86b9c6dfd99d5bb9cfd7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014r-3129011000-095de295f974d9fb5c50View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00m0-1639010000-449977cdfdab641f5d52View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000009000-280b86e4414b53facf72View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0000009000-280b86e4414b53facf72View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0bt9-0009601000-91ecd845bbd7be329f35View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-1045009000-48c3d9c1204a20d9f505View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05di-7098001000-43df34f631a91dbbbad0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06w9-7196000000-f02230f61a8c82f33a5bView 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 IDHMDB0007321
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 Compound9543888
PDB IDNot Available
ChEBI ID89253
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(18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z)/0:0) → Cytidine monophosphate + PE(18:3(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(18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z)/0:0) + Clupanodonyl CoA → TG(18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)) + Coenzyme Adetails