Showing metabocard for DG(18:2(9Z,12Z)/20:3(8Z,11Z,14Z)/0:0) (BMDB0007256)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 23:33:42 UTC
Update Date2020-05-21 16:27:53 UTC
BMDB IDBMDB0007256
Secondary Accession Numbers
  • BMDB07256
Metabolite Identification
Common NameDG(18:2(9Z,12Z)/20:3(8Z,11Z,14Z)/0:0)
DescriptionDG(18:2(9Z,12Z)/20:3(8Z,11Z,14Z)/0:0)[iso2], also known as dg(18:2(9z,12z)/20:3(8z,11z,14z)/0:0)[iso2] or Dg(18:2(9z,12z)/20:3(8z,11z,14z)/0:0)[iso2], belongs to the class of organic compounds known as 1,2-dg(18:2(9z,12z)/20:3(8z,11z,14z)/0:0)[iso2]s. These are dg(18:2(9z,12z)/20:3(8z,11z,14z)/0:0)[iso2]s containing a glycerol acylated at positions 1 and 2. Thus, DG(18:2(9Z,12Z)/20:3(8Z,11Z,14Z)/0:0)[iso2] is considered to be a diradylglycerol lipid molecule. DG(18:2(9Z,12Z)/20:3(8Z,11Z,14Z)/0:0)[iso2] is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. In cattle, DG(18:2(9Z,12Z)/20:3(8Z,11Z,14Z)/0:0)[iso2] is involved in several metabolic pathways, some of which include de novo triacylglycerol biosynthesis TG(18:2(9Z,12Z)/20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z)) pathway, de novo triacylglycerol biosynthesis TG(18:2(9Z,12Z)/20:3(8Z,11Z,14Z)/24:1(15Z)) pathway, de novo triacylglycerol biosynthesis TG(18:2(9Z,12Z)/20:3(8Z,11Z,14Z)/22:2(13Z,16Z)) pathway, and de novo triacylglycerol biosynthesis TG(18:2(9Z,12Z)/20:3(8Z,11Z,14Z)/24:0) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Linoleoyl-2-homo-g-linolenoyl-sn-glycerolHMDB
1-Linoleoyl-2-homo-gamma-linolenoyl-sn-glycerolHMDB
DAG(18:2/20:3)HMDB
DAG(18:2N6/20:3N6)HMDB
DAG(18:2W6/20:3W6)HMDB
DAG(38:5)HMDB
DG(18:2/20:3)HMDB
DG(18:2N6/20:3N6)HMDB
DG(18:2W6/20:3W6)HMDB
DG(38:5)HMDB
DiacylglycerolHMDB
Diacylglycerol(18:2/20:3)HMDB
Diacylglycerol(18:2n6/20:3n6)HMDB
Diacylglycerol(18:2W6/20:3W6)HMDB
Diacylglycerol(38:5)HMDB
DiglycerideHMDB
1-(9Z,12Z-Octadecadienoyl)-2-(8Z,11Z,14Z-eicosatrienoyl)-sn-glycerolHMDB
DG(18:2(9Z,12Z)/20:3(8Z,11Z,14Z)/0:0)Lipid Annotator
Chemical FormulaC41H70O5
Average Molecular Weight642.9915
Monoisotopic Molecular Weight642.52232535
IUPAC Name(2S)-1-hydroxy-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propan-2-yl (8Z,11Z,14Z)-icosa-8,11,14-trienoate
Traditional Namediacylglycerol
CAS Registry NumberNot Available
SMILES
[H][C@](CO)(COC(=O)CCCCCCC\C=C/C\C=C/CCCCC)OC(=O)CCCCCC\C=C/C\C=C/C\C=C/CCCCC
InChI Identifier
InChI=1S/C41H70O5/c1-3-5-7-9-11-13-15-17-19-20-22-24-26-28-30-32-34-36-41(44)46-39(37-42)38-45-40(43)35-33-31-29-27-25-23-21-18-16-14-12-10-8-6-4-2/h11-14,17-19,21-22,24,39,42H,3-10,15-16,20,23,25-38H2,1-2H3/b13-11-,14-12-,19-17-,21-18-,24-22-/t39-/m0/s1
InChI KeyYOCFNRCUDLNVHC-DEAWSBFVSA-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
logP9.74ALOGPS
logP12.86ChemAxon
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
Refractivity200.89 m³·mol⁻¹ChemAxon
Polarizability80.77 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 GC-MSPredicted GC-MS Spectrum - GC-MS ("DG(18:2(9Z,12Z)/20:3(8Z,11Z,14Z)/0:0),1TMS,#1" TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000009000-34b56338d5777ead4c29View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03g0-0009004000-d275a9edb64aa249aae0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dr-0009004000-e5e8edab420b30c9b63aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000009000-c42d84986800260de203View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03g0-0009004000-01afe348e95de3e9a402View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dr-0009004000-22e456971b44d3f346d3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0000009000-25d712cfd42c783e22f2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0000009000-25d712cfd42c783e22f2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a50-0009000000-6f36b9a1b7d442e44fa1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000f-4274069000-df60ad40e0994d66a601View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01p9-2493000000-0e5eff0880fbce1a7cccView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06ri-4597010000-8e3027b69d35828860ddView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f96-3059008000-68461fd20b9eef6b7a2bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0729-5095001000-5efd6f5163c19879818bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-3093000000-96c72dfa60355afd8dbdView 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 IDHMDB0007256
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB024449
KNApSAcK IDNot Available
Chemspider ID7822735
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9543785
PDB IDNot Available
ChEBI ID89200
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(18:2(9Z,12Z)/20:3(8Z,11Z,14Z)/0:0) → Cytidine monophosphate + PE(18:2(9Z,12Z)/20:3(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(18:2(9Z,12Z)/20:3(8Z,11Z,14Z)/0:0) + 5Z,8Z,11Z,14Z-eicosatetraenonyl-CoA → TG(18:2(9Z,12Z)/20:3n6/20:4(5Z,8Z,11Z,14Z)) + Coenzyme Adetails