Showing metabocard for DG(18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/0:0) (BMDB0007263)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 23:33:50 UTC
Update Date2020-05-21 16:27:54 UTC
BMDB IDBMDB0007263
Secondary Accession Numbers
  • BMDB07263
Metabolite Identification
Common NameDG(18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/0:0)
DescriptionDG(18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/0:0)[iso2], also known as dg(18:2(9z,12z)/22:4(7z,10z,13z,16z)/0:0)[iso2] or DAG(18:2/22:4), belongs to the class of organic compounds known as 1,2-dg(18:2(9z,12z)/22:4(7z,10z,13z,16z)/0:0)[iso2]s. These are dg(18:2(9z,12z)/22:4(7z,10z,13z,16z)/0:0)[iso2]s containing a glycerol acylated at positions 1 and 2. Thus, DG(18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/0:0)[iso2] is considered to be a diradylglycerol lipid molecule. DG(18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/0:0)[iso2] is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. In cattle, DG(18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/0:0)[iso2] is involved in a couple of metabolic pathways, which include de novo triacylglycerol biosynthesis TG(18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/24:0) pathway and de novo triacylglycerol biosynthesis TG(18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/24:1(15Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Linoleoyl-2-adrenoyl-sn-glycerolHMDB
DAG(18:2/22:4)HMDB
DAG(18:2N6/22:4N6)HMDB
DAG(18:2W6/22:4W6)HMDB
DAG(40:6)HMDB
DG(18:2/22:4)HMDB
DG(18:2N6/22:4N6)HMDB
DG(18:2W6/22:4W6)HMDB
DG(40:6)HMDB
DiacylglycerolHMDB
Diacylglycerol(18:2/22:4)HMDB
Diacylglycerol(18:2n6/22:4n6)HMDB
Diacylglycerol(18:2W6/22:4W6)HMDB
Diacylglycerol(40:6)HMDB
DiglycerideHMDB
1-(9Z,12Z-Octadecadienoyl)-2-(7Z,10Z,13Z,16Z-docosatetraenoyl)-sn-glycerolHMDB
DG(18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/0:0)Lipid Annotator
Chemical FormulaC43H72O5
Average Molecular Weight669.0288
Monoisotopic Molecular Weight668.537975414
IUPAC Name(2S)-1-hydroxy-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]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/CCCCC)OC(=O)CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC
InChI Identifier
InChI=1S/C43H72O5/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/h11-14,17-19,21-23,26,28,41,44H,3-10,15-16,20,24-25,27,29-40H2,1-2H3/b13-11-,14-12-,19-17-,22-21-,23-18-,28-26-/t41-/m0/s1
InChI KeyREWOPMLGNOGDCI-IUTJGAPQSA-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
logP9.65ALOGPS
logP13.39ChemAxon
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 Count36ChemAxon
Refractivity211.21 m³·mol⁻¹ChemAxon
Polarizability83.48 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, Positivesplash10-01p9-1296033000-3ac47e97b83e4b1ced2bView 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, Negativesplash10-040r-0096003000-d3d9fd0d9300fb80d0f2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01t9-1093000000-e6d7446760d428feb96eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03gi-4095000000-5f035f28cd9807de8ea0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-1047009000-08cda64530360e2b16d1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0200-6097001000-31c6f7c6ea448e5f9df3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06w9-6196000000-de1e95182e12940ff4d6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014r-1049004000-69e88c226b4581f57debView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02g9-2098031000-463928e03cdfe4b74975View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00ri-1092030000-2aa3514206cd69c4cf6cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-3129046000-ebcabde4c1f09cc4242eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0670-2249000000-c640c87b6533562dd92aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kr-1449100000-b3568968a2be23b01080View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000009000-e2329eb25be3f42c3a5dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0009004000-8f85c25bd00937eb2ce0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0009004000-21e4faf10fefcf3a55faView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000009000-d8fc180957e9e2b5f8d1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0000009000-d8fc180957e9e2b5f8d1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0bt9-0009601000-ff2f39827158b8213e71View 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 IDHMDB0007263
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB024456
KNApSAcK IDNot Available
Chemspider ID7822829
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9543879
PDB IDNot Available
ChEBI ID89176
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)/22:4(7Z,10Z,13Z,16Z)/0:0) → Cytidine monophosphate + PE(18:2(9Z,12Z)/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(18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/0:0) + Clupanodonyl CoA → TG(18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)) + Coenzyme Adetails