Showing metabocard for DG(18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)/0:0) (BMDB0007346)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 23:35:30 UTC
Update Date2020-05-21 16:27:58 UTC
BMDB IDBMDB0007346
Secondary Accession Numbers
  • BMDB07346
Metabolite Identification
Common NameDG(18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)/0:0)
DescriptionDG(18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)/0:0)[iso2], also known as dg(18:4(6z,9z,12z,15z)/20:5(5z,8z,11z,14z,17z)/0:0)[iso2] or DAG(18:4/20:5), belongs to the class of organic compounds known as 1,2-dg(18:4(6z,9z,12z,15z)/20:5(5z,8z,11z,14z,17z)/0:0)[iso2]s. These are dg(18:4(6z,9z,12z,15z)/20:5(5z,8z,11z,14z,17z)/0:0)[iso2]s containing a glycerol acylated at positions 1 and 2. Thus, DG(18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)/0:0)[iso2] is considered to be a diradylglycerol lipid molecule. DG(18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)/0:0)[iso2] is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. In cattle, DG(18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)/0:0)[iso2] is involved in a couple of metabolic pathways, which include de novo triacylglycerol biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z)) pathway and phosphatidylethanolamine biosynthesis pe(18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Stearidonoyl-2-eicosapentaenoyl-sn-glycerolHMDB
DAG(18:4/20:5)HMDB
DAG(18:4N3/20:5N3)HMDB
DAG(18:4W3/20:5W3)HMDB
DAG(38:9)HMDB
DG(18:4/20:5)HMDB
DG(18:4N3/20:5N3)HMDB
DG(18:4W3/20:5W3)HMDB
DG(38:9)HMDB
DiacylglycerolHMDB
Diacylglycerol(18:4/20:5)HMDB
Diacylglycerol(18:4n3/20:5n3)HMDB
Diacylglycerol(18:4W3/20:5W3)HMDB
Diacylglycerol(38:9)HMDB
DiglycerideHMDB
1-(6Z,9Z,12Z,15Z-Octadecatetraenoyl)-2-(5Z,8Z,11Z,14Z,17Z-eicosapentaenoyl)-sn-glycerolHMDB
DG(18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)/0:0)Lipid Annotator
Chemical FormulaC41H62O5
Average Molecular Weight634.928
Monoisotopic Molecular Weight634.459725094
IUPAC Name(2S)-1-hydroxy-3-[(6Z,9Z,12Z,15Z)-octadeca-6,9,12,15-tetraenoyloxy]propan-2-yl (5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoate
Traditional Namediacylglycerol
CAS Registry NumberNot Available
SMILES
[H][C@](CO)(COC(=O)CCCC\C=C/C\C=C/C\C=C/C\C=C/CC)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC
InChI Identifier
InChI=1S/C41H62O5/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/h5-8,11-14,17-19,21-22,24-25,27-28,30,39,42H,3-4,9-10,15-16,20,23,26,29,31-38H2,1-2H3/b7-5-,8-6-,13-11-,14-12-,19-17-,21-18-,24-22-,27-25-,30-28-/t39-/m0/s1
InChI KeyAMHBGJKUDUMUFD-BOUSCSLNSA-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
logP8.08ALOGPS
logP11.41ChemAxon
logS-7.3ALOGPS
pKa (Strongest Acidic)14.58ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area72.83 ŲChemAxon
Rotatable Bond Count31ChemAxon
Refractivity205.35 m³·mol⁻¹ChemAxon
Polarizability75.79 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(18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)/0:0),1TMS,#1" TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0000009000-6262e1d1e8c9932bfffaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0aq9-0009004000-4952b954842ed29bc43eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pcr-0009004000-f0c402be5858222540cdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-0155089000-3667c8d176fb860e5bb1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-2193020000-7b0de7c970c6a6e5ef4bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052r-0493010000-213e68801360574be792View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-1056009000-3143976eb357b47f61dbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05di-5095000000-21f8a8f778d367629dfbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6r-5193000000-4e09738feb9c55d59ecfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0000009000-83f4f1182df902c5177bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0aq9-0009004000-58c5c6cae63da53f1cb8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pcr-0009004000-655e11177c40ae133fb1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0000009000-f127c441698c59148432View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0000009000-f127c441698c59148432View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a59-0009000000-e2c5f7afd2df1180e93fView 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 IDHMDB0007346
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB024539
KNApSAcK IDNot Available
Chemspider ID24766083
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53478175
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(18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)/0:0) → Cytidine monophosphate + PE(18:4(6Z,9Z,12Z,15Z)/20:5(5Z,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(18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)/0:0) + Clupanodonyl CoA → TG(18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z)) + Coenzyme Adetails