Showing metabocard for DG(14:1(9Z)/18:0/0:0) (BMDB0007042)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 23:29:20 UTC
Update Date2020-05-21 16:27:26 UTC
BMDB IDBMDB0007042
Secondary Accession Numbers
  • BMDB07042
Metabolite Identification
Common NameDG(14:1(9Z)/18:0/0:0)
DescriptionDG(14:1(9Z)/18:0/0:0), also known as diacylglycerol or DAG(14:1/18:0), 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(14:1(9Z)/18:0/0:0) is considered to be a diradylglycerol lipid molecule. DG(14:1(9Z)/18:0/0:0) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. DG(14:1(9Z)/18:0/0:0) participates in a number of enzymatic reactions, within cattle. In particular, DG(14:1(9Z)/18:0/0:0) can be biosynthesized from PA(14:1(9Z)/18:0); which is catalyzed by the enzyme phosphatidate phosphatase. Furthermore, DG(14:1(9Z)/18:0/0:0) and alpha-linolenoyl-CoA can be converted into TG(14:1(9Z)/18:0/18:3(9Z,12Z,15Z)); which is catalyzed by the enzyme diacylglycerol O-acyltransferase. Furthermore, DG(14:1(9Z)/18:0/0:0) can be biosynthesized from PA(14:1(9Z)/18:0); which is mediated by the enzyme phosphatidate phosphatase. Furthermore, DG(14:1(9Z)/18:0/0:0) and meadoyl-CoA can be converted into TG(14:1(9Z)/18:0/20:3(5Z,8Z,11Z)) through the action of the enzyme diacylglycerol O-acyltransferase. Furthermore, DG(14:1(9Z)/18:0/0:0) can be biosynthesized from PA(14:1(9Z)/18:0) through the action of the enzyme phosphatidate phosphatase. Finally, DG(14:1(9Z)/18:0/0:0) and arachidonyl-CoA can be converted into TG(14:1(9Z)/18:0/20:4(5Z,8Z,11Z,14Z)); which is mediated by the enzyme diacylglycerol O-acyltransferase. In cattle, DG(14:1(9Z)/18:0/0:0) is involved in several metabolic pathways, some of which include de novo triacylglycerol biosynthesis TG(14:1(9Z)/18:0/18:3(9Z,12Z,15Z)) pathway, de novo triacylglycerol biosynthesis TG(14:1(9Z)/18:0/20:3(5Z,8Z,11Z)) pathway, de novo triacylglycerol biosynthesis TG(14:1(9Z)/18:0/20:4(5Z,8Z,11Z,14Z)) pathway, and de novo triacylglycerol biosynthesis TG(14:1(9Z)/18:0/22:2(13Z,16Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Myristoleoyl-2-stearoyl-sn-glycerolHMDB
DAG(14:1/18:0)HMDB
DAG(14:1N5/18:0)HMDB
DAG(14:1W5/18:0)HMDB
DAG(32:1)HMDB
DG(14:1/18:0)HMDB
DG(14:1N5/18:0)HMDB
DG(14:1W5/18:0)HMDB
DG(32:1)HMDB
DiacylglycerolHMDB
Diacylglycerol(14:1/18:0)HMDB
Diacylglycerol(14:1n5/18:0)HMDB
Diacylglycerol(14:1W5/18:0)HMDB
Diacylglycerol(32:1)HMDB
DiglycerideHMDB
1-(9Z-Tetradecenoyl)-2-octadecanoyl-sn-glycerolHMDB
DG(14:1(9Z)/18:0/0:0)Lipid Annotator
Chemical FormulaC35H66O5
Average Molecular Weight566.8955
Monoisotopic Molecular Weight566.491025222
IUPAC Name(2S)-1-hydroxy-3-[(9Z)-tetradec-9-enoyloxy]propan-2-yl octadecanoate
Traditional Namediacylglycerol
CAS Registry NumberNot Available
SMILES
[H]\C(CCCC)=C(/[H])CCCCCCCC(=O)OC[C@]([H])(CO)OC(=O)CCCCCCCCCCCCCCCCC
InChI Identifier
InChI=1S/C35H66O5/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/h10,12,33,36H,3-9,11,13-32H2,1-2H3/b12-10-/t33-/m0/s1
InChI KeyPAHKOLCUPPSBEU-ZUMVFQCASA-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
logP9.82ALOGPS
logP11.64ChemAxon
logS-7.4ALOGPS
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
Refractivity168.82 m³·mol⁻¹ChemAxon
Polarizability73.36 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, Positivesplash10-05g0-8595364000-51f35911a8585ea5ab25View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS ("DG(14:1(9Z)/18:0/0:0),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, Positivesplash10-001i-0000090000-b10bae501036cc2e6a49View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001m-0099090000-0d8727f63b35d6d3f279View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001l-0099090000-e1fb881367d958f24f00View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00lr-2092030000-1992f679cb08b581a114View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00w9-3093000000-fe8e70d5aec19dce70e3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-2790000000-afb63304ef27604e3e31View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014l-1197060000-0cc3ac0cd3ed747ec6c5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01bc-3695010000-f3e5e4622eeca2287d48View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-015a-9200000000-288043ad561aaa85a90eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000090000-e397b91a89d2222952f3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001m-0088090000-3489fe4d1a9072ea95d6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001l-0088090000-5b8397ab8ce6af0e5bb1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000090000-42f8dfc382daebbac87bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0000090000-42f8dfc382daebbac87bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0bt9-0009000000-d3f2e215dbab1372b64aView 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 IDHMDB0007042
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB024236
KNApSAcK IDNot Available
Chemspider ID24765876
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53477977
PDB IDNot Available
ChEBI ID88786
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)/18:0/0:0) → Cytidine monophosphate + PE(14:1(9Z)/18:0)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)/18:0/0:0) + Stearoyl-CoA → TG(14:1(9Z)/18:0/18:0)[iso3] + Coenzyme Adetails
DG(14:1(9Z)/18:0/0:0) + Oleoyl-CoA → TG(14:1(9Z)/18:0/18:1(9Z))[iso6] + Coenzyme Adetails
DG(14:1(9Z)/18:0/0:0) + Gamma-linolenoyl-CoA → TG(14:1(9Z)/18:0/18:3(6Z,9Z,12Z))[iso6] + Coenzyme Adetails
DG(14:1(9Z)/18:0/0:0) + Gondoyl-CoA → TG(14:1(9Z)/18:0/20:1(11Z))[iso6] + Coenzyme Adetails
DG(14:1(9Z)/18:0/0:0) + 5Z,8Z,11Z,14Z-eicosatetraenonyl-CoA → TG(14:1(9Z)/18:0/20:4(5Z,8Z,11Z,14Z))[iso6] + Coenzyme Adetails
DG(14:1(9Z)/18:0/0:0) + Erucoyl-CoA → TG(14:1(9Z)/18:0/22:1(13Z)) + Coenzyme Adetails
DG(14:1(9Z)/18:0/0:0) + Clupanodonyl CoA → TG(14:1(9Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z))[iso6] + Coenzyme Adetails