Showing metabocard for DG(14:0/20:3(8Z,11Z,14Z)/0:0) (BMDB0007024)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 23:28:58 UTC
Update Date2020-05-21 16:27:23 UTC
BMDB IDBMDB0007024
Secondary Accession Numbers
  • BMDB07024
Metabolite Identification
Common NameDG(14:0/20:3(8Z,11Z,14Z)/0:0)
DescriptionDG(14:0/20:3(8Z,11Z,14Z)/0:0), also known as DG(14:0/20:3) or diacylglycerol(14:0/20:3), belongs to the class of organic compounds known as 1,2-diacylglycerols. These are diacylglycerols containing a glycerol acylated at positions 1 and 2. Thus, DG(14:0/20:3(8Z,11Z,14Z)/0:0) is considered to be a diradylglycerol lipid molecule. DG(14:0/20:3(8Z,11Z,14Z)/0:0) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. CDP-Ethanolamine and DG(14:0/20:3(8Z,11Z,14Z)/0:0) can be converted into cytidine monophosphate and PE(14:0/20:3(8Z,11Z,14Z)) through its interaction with the enzyme choline/ethanolaminephosphotransferase. In cattle, DG(14:0/20:3(8Z,11Z,14Z)/0:0) is involved in the metabolic pathway called phosphatidylethanolamine biosynthesis pe(14:0/20:3(8Z,11Z,14Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
DG(14:0/20:3(8Z,11Z,14Z)/0:0)Lipid Annotator
DG(14:0/20:3)Lipid Annotator, HMDB
1-myristoyl-2-homo-g-linolenoyl-sn-glycerolLipid Annotator, HMDB
DiglycerideLipid Annotator, HMDB
Diacylglycerol(14:0/20:3)Lipid Annotator, HMDB
DAG(14:0/20:3)Lipid Annotator, HMDB
DiacylglycerolLipid Annotator, HMDB
DAG(34:3)Lipid Annotator, HMDB
DG(34:3)Lipid Annotator, HMDB
1-tetradecanoyl-2-(8Z,11Z,14Z-eicosatrienoyl)-sn-glycerolLipid Annotator, HMDB
Diacylglycerol(34:3)Lipid Annotator, HMDB
Chemical FormulaC37H66O5
Average Molecular Weight590.9169
Monoisotopic Molecular Weight590.491025222
IUPAC Name(2S)-1-hydroxy-3-(tetradecanoyloxy)propan-2-yl (8Z,11Z,14Z)-icosa-8,11,14-trienoate
Traditional Namediacylglycerol
CAS Registry NumberNot Available
SMILES
[H]\C(CCCCC)=C(/[H])C\C([H])=C(\[H])C\C([H])=C(\[H])CCCCCCC(=O)O[C@@]([H])(CO)COC(=O)CCCCCCCCCCCCC
InChI Identifier
InChI=1S/C37H66O5/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/h11,13,16-17,19-20,35,38H,3-10,12,14-15,18,21-34H2,1-2H3/b13-11-,17-16-,20-19-/t35-/m0/s1
InChI KeyMIOCZRAJMXIEKP-NYBWPXJJSA-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
logP9.77ALOGPS
logP11.81ChemAxon
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 Count33ChemAxon
Refractivity180.25 m³·mol⁻¹ChemAxon
Polarizability74.96 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, Positivesplash10-008i-5951314000-1ace4b21bee75794d2c9View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS ("DG(14:0/20:3(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-0000009000-2c9dba2a539fdca961d6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03kr-0099071000-1aa833c68d7bde42a520View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08g9-0099036000-33bbd1233b6f15c6305aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000009000-06c2ad30942913111b60View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0000009000-06c2ad30942913111b60View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a50-0009000000-cf03a6ece7aeedc61010View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0000009000-418bfe830d05946bacd1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03kr-0099071000-4904617a62442c3be3daView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08g9-0099036000-3b4310d126346d6fb53cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0kdr-2069050000-eec5e81fe9485ead2b3dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056r-3095010000-27fbd297de96b6eaea02View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6r-2295000000-bc847095f0c9fed4677dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01p6-1146090000-ce949fc4432440813b4fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0079-3390010000-3836c99579d3645232adView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001l-9310000000-e7b186354e49a91ee130View 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 IDHMDB0007024
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 Compound53477959
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(14:0/20:3(8Z,11Z,14Z)/0:0) → Cytidine monophosphate + PE(14:0/20:3(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(14:0/20:3(8Z,11Z,14Z)/0:0) + 5Z,8Z,11Z,14Z-eicosatetraenonyl-CoA → TG(14:0/20:3n6/20:4(5Z,8Z,11Z,14Z)) + Coenzyme Adetails
DG(14:0/20:3(8Z,11Z,14Z)/0:0) + Docosanoyl-CoA → TG(14:0/20:3n6/22:0) + Coenzyme Adetails
DG(14:0/20:3(8Z,11Z,14Z)/0:0) + Erucoyl-CoA → TG(14:0/20:3n6/22:1(13Z)) + Coenzyme Adetails
DG(14:0/20:3(8Z,11Z,14Z)/0:0) + Clupanodonyl CoA → TG(14:0/20:3n6/22:5(7Z,10Z,13Z,16Z,19Z)) + Coenzyme Adetails
DG(14:0/20:3(8Z,11Z,14Z)/0:0) + Tetracosanoyl-CoA → TG(14:0/20:3n6/24:0) + Coenzyme Adetails