Showing metabocard for DG(14:0/18:2(9Z,12Z)/0:0) (BMDB0007016)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 23:28:49 UTC
Update Date2020-05-21 16:27:21 UTC
BMDB IDBMDB0007016
Secondary Accession Numbers
  • BMDB07016
Metabolite Identification
Common NameDG(14:0/18:2(9Z,12Z)/0:0)
DescriptionDG(14:0/18:2(9Z,12Z)/0:0), also known as diacylglycerol(32:2) or DG(14:0/18:2), belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions. Thus, DG(14:0/18:2(9Z,12Z)/0:0) is considered to be a diradylglycerol lipid molecule. DG(14:0/18:2(9Z,12Z)/0:0) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. DG(14:0/18:2(9Z,12Z)/0:0) participates in a number of enzymatic reactions, within cattle. In particular, CDP-Ethanolamine and DG(14:0/18:2(9Z,12Z)/0:0) can be converted into cytidine monophosphate and PE(14:0/18:2(9Z,12Z)); which is catalyzed by the enzyme choline/ethanolaminephosphotransferase. In addition, CDP-Choline and DG(14:0/18:2(9Z,12Z)/0:0) can be converted into cytidine monophosphate and PC(14:0/18:2(9Z,12Z)); which is catalyzed by the enzyme choline/ethanolaminephosphotransferase. In cattle, DG(14:0/18:2(9Z,12Z)/0:0) is involved in the metabolic pathway called phosphatidylcholine biosynthesis PC(14:0/18:2(9Z,12Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Tetradecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycerolChEBI
DG(14:0/18:2(9Z,12Z)/0:0)[iso2]ChEBI
DG(14:0/18:2/0:0)ChEBI
Diacylglycerol(32:2)Lipid Annotator, HMDB
DG(14:0/18:2)Lipid Annotator, HMDB
DG(14:0/18:2(9Z,12Z)/0:0)Lipid Annotator
Diacylglycerol(14:0/18:2)Lipid Annotator, HMDB
DAG(32:2)Lipid Annotator, HMDB
DiacylglycerolLipid Annotator, HMDB
1-myristoyl-2-linoleoyl-sn-glycerolLipid Annotator, HMDB
DG(32:2)Lipid Annotator, HMDB
DAG(14:0/18:2)Lipid Annotator, HMDB
DiglycerideLipid Annotator, HMDB
Chemical FormulaC35H64O5
Average Molecular Weight564.8797
Monoisotopic Molecular Weight564.475375158
IUPAC Name(2S)-1-hydroxy-3-(tetradecanoyloxy)propan-2-yl (9Z,12Z)-octadeca-9,12-dienoate
Traditional Namediacylglycerol
CAS Registry NumberNot Available
SMILES
[H]C(CCCCC)=C([H])C\C([H])=C(\[H])CCCCCCCC(=O)O[C@@]([H])(CO)COC(=O)CCCCCCCCCCCCC
InChI Identifier
InChI=1S/C35H64O5/c1-3-5-7-9-11-13-15-16-17-18-20-22-24-26-28-30-35(38)40-33(31-36)32-39-34(37)29-27-25-23-21-19-14-12-10-8-6-4-2/h11,13,16-17,33,36H,3-10,12,14-15,18-32H2,1-2H3/b13-11-,17-16-/t33-/m0/s1
InChI KeyWVBVUWWRPSWGDS-JWVBYZEHSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassLineolic acids and derivatives
Direct ParentLineolic acids and derivatives
Alternative Parents
Substituents
  • Octadecanoid
  • 1,2-acyl-sn-glycerol
  • Diacylglycerol
  • Diradylglycerol
  • Fatty acid ester
  • Glycerolipid
  • Dicarboxylic acid or derivatives
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic oxide
  • Carbonyl group
  • Primary alcohol
  • 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
  • Cytoplasm
  • 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
logP11.28ChemAxon
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 Count32ChemAxon
Refractivity169.93 m³·mol⁻¹ChemAxon
Polarizability71.75 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, Positivesplash10-0fl9-5962233000-035cd06b6e57a7e5c8efView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS ("DG(14:0/18:2(9Z,12Z)/0:0),1TMS,#1" TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
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, Positivesplash10-001i-0000090000-51d305f10f90afe4eb07View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0099090000-ef133878726b0ad1e768View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0099090000-ddbc32971365816cd383View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000090000-ec1b73afc18d0387d07fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0000090000-ec1b73afc18d0387d07fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-0009000000-3aac7d370d455cedd573View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000090000-279f8e7a1315590373dcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0088090000-d4cf5a08dd344d604d07View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0088090000-2f63ff044dd55a3aed2aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0h00-2095050000-e627606cecf1f19b002fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-3092010000-0567121a677e36916a4eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-1191000000-0c0cad94d33021787e93View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014r-3246290000-09b73ad114dc61089dcbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03ei-5691010000-120ff15affae499ec56bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0564-9300000000-3bcb16757bcff66a6db8View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • 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 IDHMDB0007016
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID24765850
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound14275352
PDB IDNot Available
ChEBI ID84392
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(14:0/18:2(9Z,12Z)/0:0) → Cytidine monophosphate + PE(14:0/18:2(9Z,12Z))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(14:0/18:2(9Z,12Z)/0:0) + Gamma-linolenoyl-CoA → TG(14:0/18:2(9Z,12Z)/18:3(6Z,9Z,12Z)) + Coenzyme Adetails
DG(14:0/18:2(9Z,12Z)/0:0) + Eicosanoyl-CoA → TG(14:0/18:2(9Z,12Z)/20:0)[iso6] + Coenzyme Adetails
DG(14:0/18:2(9Z,12Z)/0:0) + Gondoyl-CoA → TG(14:0/18:2(9Z,12Z)/20:1(11Z))[iso6] + Coenzyme Adetails
DG(14:0/18:2(9Z,12Z)/0:0) + 5Z,8Z,11Z,14Z-eicosatetraenonyl-CoA → TG(14:0/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)) + Coenzyme Adetails
DG(14:0/18:2(9Z,12Z)/0:0) + Docosanoyl-CoA → TG(14:0/18:2(9Z,12Z)/22:0)[iso6] + Coenzyme Adetails
DG(14:0/18:2(9Z,12Z)/0:0) + Erucoyl-CoA → TG(14:0/18:2(9Z,12Z)/22:1(13Z)) + Coenzyme Adetails
DG(14:0/18:2(9Z,12Z)/0:0) + Clupanodonyl CoA → TG(14:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)) + Coenzyme Adetails
DG(14:0/18:2(9Z,12Z)/0:0) + Tetracosanoyl-CoA → TG(14:0/18:2(9Z,12Z)/24:0) + Coenzyme Adetails