Showing metabocard for DG(18:2(9Z,12Z)/22:0/0:0) (BMDB0007260)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 23:33:47 UTC
Update Date2020-05-21 16:27:54 UTC
BMDB IDBMDB0007260
Secondary Accession Numbers
  • BMDB07260
Metabolite Identification
Common NameDG(18:2(9Z,12Z)/22:0/0:0)
DescriptionDG(18:2(9Z,12Z)/22:0/0:0)[iso2], also known as dg(18:2(9z,12z)/22:0/0:0)[iso2] or DAG(18:2/22:0), belongs to the class of organic compounds known as 1,2-dg(18:2(9z,12z)/22:0/0:0)[iso2]s. These are dg(18:2(9z,12z)/22:0/0:0)[iso2]s containing a glycerol acylated at positions 1 and 2. Thus, DG(18:2(9Z,12Z)/22:0/0:0)[iso2] is considered to be a diradylglycerol lipid molecule. DG(18:2(9Z,12Z)/22:0/0:0)[iso2] is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. In cattle, DG(18:2(9Z,12Z)/22:0/0:0)[iso2] is involved in the metabolic pathway called de novo triacylglycerol biosynthesis TG(18:2(9Z,12Z)/22:0/22:5(4Z,7Z,10Z,13Z,16Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Linoleoyl-2-behenoyl-sn-glycerolHMDB
DAG(18:2/22:0)HMDB
DAG(18:2N6/22:0)HMDB
DAG(18:2W6/22:0)HMDB
DAG(40:2)HMDB
DG(18:2/22:0)HMDB
DG(18:2N6/22:0)HMDB
DG(18:2W6/22:0)HMDB
DG(40:2)HMDB
DiacylglycerolHMDB
Diacylglycerol(18:2/22:0)HMDB
Diacylglycerol(18:2n6/22:0)HMDB
Diacylglycerol(18:2W6/22:0)HMDB
Diacylglycerol(40:2)HMDB
DiglycerideHMDB
1-(9Z,12Z-Octadecadienoyl)-2-docosanoyl-sn-glycerolHMDB
DG(18:2(9Z,12Z)/22:0/0:0)Lipid Annotator
Chemical FormulaC43H80O5
Average Molecular Weight677.0923
Monoisotopic Molecular Weight676.60057567
IUPAC Name(2S)-1-hydroxy-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propan-2-yl docosanoate
Traditional Namediacylglycerol
CAS Registry NumberNot Available
SMILES
[H][C@](CO)(COC(=O)CCCCCCC\C=C/C\C=C/CCCCC)OC(=O)CCCCCCCCCCCCCCCCCCCCC
InChI Identifier
InChI=1S/C43H80O5/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/h12,14,18,23,41,44H,3-11,13,15-17,19-22,24-40H2,1-2H3/b14-12-,23-18-/t41-/m0/s1
InChI KeyMUGMVAWNRXSCNZ-MBAZWWNYSA-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
logP10.65ALOGPS
logP14.84ChemAxon
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 Count40ChemAxon
Refractivity206.74 m³·mol⁻¹ChemAxon
Polarizability88.35 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, Positivesplash10-0006-0000009000-5ae7078e1cb8cf60ee8eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052t-0009004000-4931009469bc75b5fadbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000n-0009004000-c282ec464d4421684795View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000009000-f547193af50bcd23c837View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052t-0009004000-cc80842d4e616fa1fe5aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000n-0009004000-057ec19621aae5d44793View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05i0-2119025000-b4b2356e865217875d10View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05fr-2019001000-936822bbe3b03836e1c8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05fs-9617000000-71e46cb97e6e70b5d908View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-2087109000-1e2646495ad583cf476aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0109-3049001000-60674e89b52ef5866e2aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-2095000000-d29ad68460e08d86e08eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0000009000-7723839093719bf0ca85View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0000009000-7723839093719bf0ca85View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0b90-0009601000-baba90cf1c30806f19afView 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 IDHMDB0007260
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB024453
KNApSAcK IDNot Available
Chemspider ID7822783
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9543833
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(18:2(9Z,12Z)/22:0/0:0) → Cytidine monophosphate + PE(18:2(9Z,12Z)/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(18:2(9Z,12Z)/22:0/0:0) + Docosanoyl-CoA → TG(18:2(9Z,12Z)/22:0/22:0) + Coenzyme Adetails
DG(18:2(9Z,12Z)/22:0/0:0) + Erucoyl-CoA → TG(18:2(9Z,12Z)/22:0/22:1(13Z)) + Coenzyme Adetails
DG(18:2(9Z,12Z)/22:0/0:0) + Clupanodonyl CoA → TG(18:2(9Z,12Z)/22:0/22:5(7Z,10Z,13Z,16Z,19Z)) + Coenzyme Adetails