Showing metabocard for DG(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/0:0) (BMDB0007258)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 23:33:45 UTC
Update Date2020-05-21 16:27:53 UTC
BMDB IDBMDB0007258
Secondary Accession Numbers
  • BMDB07258
Metabolite Identification
Common NameDG(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/0:0)
DescriptionDG(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/0:0), also known as dg(18:2(9z,12z)/20:4(8z,11z,14z,17z)/0:0) or DG(18:2/20:4), belongs to the class of organic compounds known as 1,2-dg(18:2(9z,12z)/20:4(8z,11z,14z,17z)/0:0)s. These are dg(18:2(9z,12z)/20:4(8z,11z,14z,17z)/0:0)s containing a glycerol acylated at positions 1 and 2. DG(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/0:0) is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). DG(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/0:0) participates in a number of enzymatic reactions, within cattle. In particular, DG(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/0:0) can be biosynthesized from PA(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z)); which is catalyzed by the enzyme phosphatidate phosphatase. Furthermore, DG(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/0:0) and erucoyl-CoA can be converted into TG(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/22:1(13Z)); which is catalyzed by the enzyme dg(18:2(9z,12z)/20:4(8z,11z,14z,17z)/0:0) O-acyltransferase. Furthermore, DG(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/0:0) can be biosynthesized from PA(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z)) through its interaction with the enzyme phosphatidate phosphatase. Furthermore, DG(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/0:0) and nervonoyl-CoA can be converted into TG(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/24:1(15Z)) through the action of the enzyme dg(18:2(9z,12z)/20:4(8z,11z,14z,17z)/0:0) O-acyltransferase. Furthermore, DG(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/0:0) can be biosynthesized from PA(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z)); which is catalyzed by the enzyme phosphatidate phosphatase. Finally, DG(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/0:0) and docosanoyl-CoA can be converted into TG(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/22:0); which is catalyzed by the enzyme dg(18:2(9z,12z)/20:4(8z,11z,14z,17z)/0:0) O-acyltransferase. In cattle, DG(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/0:0) is involved in a few metabolic pathways, which include de novo triacylglycerol biosynthesis TG(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/22:1(13Z)) pathway, de novo triacylglycerol biosynthesis TG(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/24:1(15Z)) pathway, and de novo triacylglycerol biosynthesis TG(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/22:0) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Diacylglycerol(38:6)HMDB
DG(38:6)HMDB
1-Linoleoyl-2-eicsoatetraenoyl-sn-glycerolHMDB
DAG(38:6)HMDB
DiglycerideHMDB
DG(18:2/20:4)HMDB
DiacylglycerolHMDB
Diacylglycerol(18:2/20:4)HMDB
1-(9Z,12Z-Octadecadienoyl)-2-(8Z,11Z,14Z,17Z-eicosapentaenoyl)-sn-glycerolHMDB
DAG(18:2/20:4)HMDB
DG(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/0:0)Lipid Annotator
Chemical FormulaC41H68O5
Average Molecular Weight640.9756
Monoisotopic Molecular Weight640.506675286
IUPAC Name(2S)-1-hydroxy-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propan-2-yl (8Z,11Z,14Z,17Z)-icosa-8,11,14,17-tetraenoate
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/C\C=C/CC
InChI Identifier
InChI=1S/C41H68O5/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/h5,7,11-14,17-19,21-22,24,39,42H,3-4,6,8-10,15-16,20,23,25-38H2,1-2H3/b7-5-,13-11-,14-12-,19-17-,21-18-,24-22-/t39-/m0/s1
InChI KeyXQKXAZZSUMABAU-HKOSRXLCSA-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 DescriptorsNot Available
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
logP9.19ALOGPS
logP12.5ChemAxon
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
Refractivity202 m³·mol⁻¹ChemAxon
Polarizability79.17 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, Positivesplash10-000i-1494111000-019db4b76d5eb6b58b03View 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 GC-MSPredicted GC-MS Spectrum - GC-MS ("DG(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/0:0),1TMS,#1" TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-06rl-1098005000-a19d903f9331d745ea52View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01p9-2094011000-3b63ff024a15e589981cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1091110000-ec354b4eba770eb3a2baView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0gy9-0095003000-82bd99cbee6f5625d83eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01t9-1093000000-28412f11074f58869da9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0m2i-3092000000-5e82b0aa202cd909d131View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-1047009000-4e9e26e4a9b47e2de467View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00b9-5095001000-c45268ac6a644937bf1fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0m29-5193000000-02dcfff22a272d63ab49View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-06rf-4177089000-379d6fffe7f039f11012View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01p9-2294010000-499d2a8523139f398285View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01p9-1598000000-9f6129bd81101afc1ae4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0000009000-0697d21e1d6f73bcdbfeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03kr-0009004000-7ffbea8b11eed7c08883View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08g9-0009004000-777bb2457771df18712dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000009000-e8086b36c3df6f24dd64View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0000009000-e8086b36c3df6f24dd64View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a60-0009000000-ce78dc522fa40e0084e6View 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 IDHMDB0007258
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 Compound53478108
PDB IDNot Available
ChEBI ID89202
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)/20:4(8Z,11Z,14Z,17Z)/0:0) → Cytidine monophosphate + PE(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z))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)/20:4(8Z,11Z,14Z,17Z)/0:0) + Clupanodonyl CoA → TG(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z)) + Coenzyme Adetails