Showing metabocard for DG(14:1(9Z)/20:3(8Z,11Z,14Z)/0:0) (BMDB0007053)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 23:29:33 UTC
Update Date2020-05-21 16:27:28 UTC
BMDB IDBMDB0007053
Secondary Accession Numbers
  • BMDB07053
Metabolite Identification
Common NameDG(14:1(9Z)/20:3(8Z,11Z,14Z)/0:0)
DescriptionDG(14:1(9Z)/20:3(8Z,11Z,14Z)/0:0)[iso2], also known as dg(14:1(9z)/20:3(8z,11z,14z)/0:0)[iso2] or DG(14:1/20:3), belongs to the class of organic compounds known as 1,2-dg(14:1(9z)/20:3(8z,11z,14z)/0:0)[iso2]s. These are dg(14:1(9z)/20:3(8z,11z,14z)/0:0)[iso2]s containing a glycerol acylated at positions 1 and 2. Thus, DG(14:1(9Z)/20:3(8Z,11Z,14Z)/0:0)[iso2] is considered to be a diradylglycerol lipid molecule. DG(14:1(9Z)/20:3(8Z,11Z,14Z)/0:0)[iso2] is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. In cattle, DG(14:1(9Z)/20:3(8Z,11Z,14Z)/0:0)[iso2] is involved in a few metabolic pathways, which include de novo triacylglycerol biosynthesis TG(14:1(9Z)/20:3(8Z,11Z,14Z)/22:0) pathway, de novo triacylglycerol biosynthesis TG(14:1(9Z)/20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)) pathway, and phosphatidylethanolamine biosynthesis pe(14:1(9Z)/20:3(8Z,11Z,14Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Diacylglycerol(34:4)HMDB
DG(34:4)HMDB
Diacylglycerol(14:1/20:3)HMDB
1-Myristoleoyl-2-homo-g-linolenoyl-sn-glycerolHMDB
DiglycerideHMDB
DAG(34:4)HMDB
DiacylglycerolHMDB
DG(14:1/20:3)HMDB
DAG(14:1/20:3)HMDB
1-(9Z-Tetradecenoyl)-2-(8Z,11Z,14Z-eicosatrienoyl)-sn-glycerolHMDB
DG(14:1(9Z)/20:3(8Z,11Z,14Z)/0:0)Lipid Annotator
Chemical FormulaC37H64O5
Average Molecular Weight588.9011
Monoisotopic Molecular Weight588.475375158
IUPAC Name(2S)-1-hydroxy-3-[(9Z)-tetradec-9-enoyloxy]propan-2-yl (8Z,11Z,14Z)-icosa-8,11,14-trienoate
Traditional Namediacylglycerol
CAS Registry NumberNot Available
SMILES
[H][C@](CO)(COC(=O)CCCCCCC\C=C/CCCC)OC(=O)CCCCCC\C=C/C\C=C/C\C=C/CCCCC
InChI Identifier
InChI=1S/C37H64O5/c1-3-5-7-9-11-13-15-16-17-18-19-20-22-24-26-28-30-32-37(40)42-35(33-38)34-41-36(39)31-29-27-25-23-21-14-12-10-8-6-4-2/h10-13,16-17,19-20,35,38H,3-9,14-15,18,21-34H2,1-2H3/b12-10-,13-11-,17-16-,20-19-/t35-/m0/s1
InChI KeyIUUIEXFKBNBZAX-WHJULUMISA-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
logP9.36ALOGPS
logP11.44ChemAxon
logS-7.5ALOGPS
pKa (Strongest Acidic)14.58ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area72.83 ŲChemAxon
Rotatable Bond Count32ChemAxon
Refractivity181.37 m³·mol⁻¹ChemAxon
Polarizability74.36 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 (1 TMS) - 70eV, Positivesplash10-0abj-8893337000-8c86ae387cbef4984a9eView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS ("DG(14:1(9Z)/20:3(8Z,11Z,14Z)/0:0),1TMS,#1" TMS) - 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, Positivesplash10-0a4i-0000009000-b3b3c003f4a39cd41d77View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03lr-0099071000-ed973a7f85a7ce99390fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08h9-0099036000-fa817f19816a4242d08bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-1092070000-8ef6b49fc9b97033ebd2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0adi-3092010000-29dbf50535bb276fe54fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-4294000000-d01f7a2277d47e91561cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-1243190000-927ff1495c2c5ec674a1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-2392010000-fd5dec65f3ec6e90c535View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06tr-4975100000-2f598ff7f48fca07c0bfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0000009000-ef32778e747adcbc98abView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03lr-0099071000-d37e454a36c5eadb7f0dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08h9-0099036000-fcdb940f03eb31fb2050View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000009000-7aced06f5b39c28eb59fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0000009000-7aced06f5b39c28eb59fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a50-0009000000-84c1dd87a1edd707b833View 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 IDHMDB0007053
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 Compound53477988
PDB IDNot Available
ChEBI ID88722
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(14:1(9Z)/20:3(8Z,11Z,14Z)/0:0) → Cytidine monophosphate + PE(14:1(9Z)/20:3(8Z,11Z,14Z))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(14:1(9Z)/20:3(8Z,11Z,14Z)/0:0) + 5Z,8Z,11Z,14Z-eicosatetraenonyl-CoA → TG(14:1(9Z)/20:3n6/20:4(5Z,8Z,11Z,14Z)) + Coenzyme Adetails
DG(14:1(9Z)/20:3(8Z,11Z,14Z)/0:0) + Erucoyl-CoA → TG(14:1(9Z)/20:3n6/22:1(13Z)) + Coenzyme Adetails
DG(14:1(9Z)/20:3(8Z,11Z,14Z)/0:0) + Clupanodonyl CoA → TG(14:1(9Z)/20:3n6/22:5(7Z,10Z,13Z,16Z,19Z)) + Coenzyme Adetails