Showing metabocard for DG(18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z)/0:0) (BMDB0007349)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 23:35:34 UTC
Update Date2020-05-21 16:27:58 UTC
BMDB IDBMDB0007349
Secondary Accession Numbers
  • BMDB07349
Metabolite Identification
Common NameDG(18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z)/0:0)
DescriptionDG(18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z)/0:0)[iso2], also known as dg(18:4(6z,9z,12z,15z)/22:2(13z,16z)/0:0)[iso2] or DG(18:4/22:2), belongs to the class of organic compounds known as 1,2-dg(18:4(6z,9z,12z,15z)/22:2(13z,16z)/0:0)[iso2]s. These are dg(18:4(6z,9z,12z,15z)/22:2(13z,16z)/0:0)[iso2]s containing a glycerol acylated at positions 1 and 2. Thus, DG(18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z)/0:0)[iso2] is considered to be a diradylglycerol lipid molecule. DG(18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z)/0:0)[iso2] is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. In cattle, DG(18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z)/0:0)[iso2] is involved in the metabolic pathway called de novo triacylglycerol biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
DAG(40:6)HMDB
DG(18:4/22:2)HMDB
DiglycerideHMDB
DG(40:6)HMDB
DiacylglycerolHMDB
Diacylglycerol(18:4/22:2)HMDB
1-Stearidonoyl-2-docosadienoyl-sn-glycerolHMDB
DAG(18:4/22:2)HMDB
1-(6Z,9Z,12Z,15Z-Octadecatetraenoyl)-2-(13Z,16Z-docosadienoyl)-sn-glycerolHMDB
Diacylglycerol(40:6)HMDB
DG(18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z)/0:0)Lipid Annotator
Chemical FormulaC43H72O5
Average Molecular Weight669.0288
Monoisotopic Molecular Weight668.537975414
IUPAC Name(2S)-1-hydroxy-3-[(6Z,9Z,12Z,15Z)-octadeca-6,9,12,15-tetraenoyloxy]propan-2-yl (13Z,16Z)-docosa-13,16-dienoate
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)CCCCCCCCCCC\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/h6,8,11-14,17-19,23,27,29,41,44H,3-5,7,9-10,15-16,20-22,24-26,28,30-40H2,1-2H3/b8-6-,13-11-,14-12-,19-17-,23-18-,29-27-/t41-/m0/s1
InChI KeyFUDGZBMOORLTCG-FCDTXGFCSA-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
logP9.66ALOGPS
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
Polarizability83.97 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, Positivesplash10-001u-2497012000-9efb1244dae03ad98b2bView 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, Positivesplash10-014i-1049004000-56b4146b9f302a568551View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0lfu-2069011000-97474f262624007e2943View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-017i-1094110000-3a21ab0945b117abe456View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-05r9-0096003000-107b8323ea532e92b17fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056r-1093000000-b364d4fdcc37dc0bc835View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0573-4095000000-b98699b73dd24b93367fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-1048009000-19c69f5ffe0cfe87f68dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05di-7097001000-b858792815d4d3e018feView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-4094000000-f75cae601c07fbb2c472View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-2116095000-9b29bf9f38c02f165e75View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-3119000000-6becd14a581d0094a706View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-3559000000-dc670b348e46a8cbc83aView 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, Positivesplash10-0f8f-0009004000-639b49de4fd9d4a69745View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001x-0009004000-997a5f70c86dcd92d9eaView 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, Positivesplash10-0aor-0019701000-f67687a0be947233f68cView 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 IDHMDB0007349
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB024542
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53478178
PDB IDNot Available
ChEBI ID88974
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)/22:2(13Z,16Z)/0:0) → Cytidine monophosphate + PE(18:4(6Z,9Z,12Z,15Z)/22:2(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(18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z)/0:0) + Clupanodonyl CoA → TG(18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)) + Coenzyme Adetails