Showing metabocard for DG(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/0:0) (BMDB0007313)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 23:34:51 UTC
Update Date2020-05-21 16:27:56 UTC
BMDB IDBMDB0007313
Secondary Accession Numbers
  • BMDB07313
Metabolite Identification
Common NameDG(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/0:0)
DescriptionDG(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/0:0), also known as DAG(18:3/20:3) or dg(18:3(9z,12z,15z)/20:3(5z,8z,11z)/0:0), belongs to the class of organic compounds known as 1,2-dg(18:3(9z,12z,15z)/20:3(5z,8z,11z)/0:0)s. These are dg(18:3(9z,12z,15z)/20:3(5z,8z,11z)/0:0)s containing a glycerol acylated at positions 1 and 2. DG(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/0:0) is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). DG(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/0:0) participates in a number of enzymatic reactions, within cattle. In particular, DG(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/0:0) can be biosynthesized from PA(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)); which is mediated by the enzyme phosphatidate phosphatase. Furthermore, DG(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/0:0) and dihomo-gamma-linolenoyl-CoA can be converted into TG(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z)) through the action of the enzyme dg(18:3(9z,12z,15z)/20:3(5z,8z,11z)/0:0) O-acyltransferase. Furthermore, DG(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/0:0) can be biosynthesized from PA(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)); which is catalyzed by the enzyme phosphatidate phosphatase. Furthermore, DG(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/0:0) and erucoyl-CoA can be converted into TG(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/22:1(13Z)) through its interaction with the enzyme dg(18:3(9z,12z,15z)/20:3(5z,8z,11z)/0:0) O-acyltransferase. Furthermore, DG(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/0:0) can be biosynthesized from PA(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)); which is mediated by the enzyme phosphatidate phosphatase. Finally, DG(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/0:0) and adrenoyl-CoA can be converted into TG(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z)) through its interaction with the enzyme dg(18:3(9z,12z,15z)/20:3(5z,8z,11z)/0:0) O-acyltransferase. In cattle, DG(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/0:0) is involved in several metabolic pathways, some of which include de novo triacylglycerol biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z)) pathway, de novo triacylglycerol biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/22:1(13Z)) pathway, de novo triacylglycerol biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z)) pathway, and de novo triacylglycerol biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/24:1(15Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-[(9Z,12Z,15Z)-Octadeca-9,12,15-trienoyl]-2-[(5Z,8Z,11Z)-icosa-5,8,11-trienoyl]-sn-glycerolChEBI
1-[(9Z,12Z,15Z)-Octadecatrienoyl]-2-[(5Z,8Z,11Z)-icosatrienoyl]-sn-glycerolChEBI
DAG(18:3/20:3)ChEBI
DAG(18:3N3/20:3N9)ChEBI
DAG(18:3W3/20:3W9)ChEBI
DAG(38:6)ChEBI
DG(18:3/20:3)ChEBI
DG(18:3N3/20:3N9)ChEBI
DG(18:3W3/20:3W9)ChEBI
DG(38:6)ChEBI
Diacylglycerol(18:3/20:3)ChEBI
Diacylglycerol(18:3n3/20:3n9)ChEBI
Diacylglycerol(18:3W3/20:3W9)ChEBI
Diacylglycerol(38:6)ChEBI
1-a-Linolenoyl-2-meadoyl-sn-glycerolHMDB
1-alpha-Linolenoyl-2-meadoyl-sn-glycerolHMDB
DiacylglycerolHMDB
DiglycerideHMDB
1-(9Z,12Z,15Z-Octadeatrienoyl)-2-(5Z,8Z,11Z-eicosatrienoyl)-sn-glycerolHMDB
DG(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/0:0)Lipid Annotator
Chemical FormulaC41H68O5
Average Molecular Weight640.9756
Monoisotopic Molecular Weight640.506675286
IUPAC Name(2S)-1-hydroxy-3-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]propan-2-yl (5Z,8Z,11Z)-icosa-5,8,11-trienoate
Traditional Namediacylglycerol
CAS Registry NumberNot Available
SMILES
[H][C@](CO)(COC(=O)CCCCCCC\C=C/C\C=C/C\C=C/CC)OC(=O)CCC\C=C/C\C=C/C\C=C/CCCCCCCC
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/h6,8,12,14,17-19,21-22,24,28,30,39,42H,3-5,7,9-11,13,15-16,20,23,25-27,29,31-38H2,1-2H3/b8-6-,14-12-,19-17-,21-18-,24-22-,30-28-/t39-/m0/s1
InChI KeyXPXCMAYRPSSBKG-VRRKQHPASA-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
logP9.26ALOGPS
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
Polarizability80.06 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, Positivesplash10-03ei-4395111000-ebe9f608833cd63611b8View 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(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/0:0),1TMS,#1" TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01pc-1098005000-df3b4dd41ed394133176View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01p9-2094101000-a3366b8690b38bdb5e65View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03yr-1091110000-f744cad8dbfaf6505a58View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a70-0096003000-8ce4f36eb1870a5e2e6fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056r-1093000000-16615ab80ca0e7dec5d5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6r-3092000000-9321c10cc57cd72cb257View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-1242094000-ce47987150b9e43a0734View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-4393010000-407fe4a72a3007df8850View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-053i-3985000000-f7f17029cee9af0c4ee9View 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, Positivesplash10-0a50-0009000000-86f7c54f7b7513bb0186View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-2046009000-16532747160517de67a4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0adi-6095001000-fe1adc839965ca75501fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-4093000000-d368f4c2dbe63a083b80View 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-0009004000-1141ed4a7f7ef5095419View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08g9-0009004000-3421b93063de8949f081View 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 IDHMDB0007313
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB024506
KNApSAcK IDNot Available
Chemspider ID24766059
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53478151
PDB IDNot Available
ChEBI ID89238
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)/20:3(5Z,8Z,11Z)/0:0) → Cytidine monophosphate + PE(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z))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)/20:3(5Z,8Z,11Z)/0:0) + Clupanodonyl CoA → TG(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z)) + Coenzyme Adetails