Showing metabocard for TG(18:1(9Z)/18:1(9Z)/18:3(6Z,9Z,12Z))[iso3] (BMDB0063546)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2018-08-29 17:23:33 UTC
Update Date2020-06-04 20:26:23 UTC
BMDB IDBMDB0063546
Secondary Accession Numbers
  • BMDB63546
Metabolite Identification
Common NameTG(18:1(9Z)/18:1(9Z)/18:3(6Z,9Z,12Z))[iso3]
DescriptionTG(18:1(9Z)/18:1(9Z)/18:3(6Z,9Z,12Z))[iso6] belongs to the class of organic compounds known as triacylglycerols. These are glycerides consisting of three fatty acid chains covalently bonded to a glycerol molecule through ester linkages. Thus, TG(18:1(9Z)/18:1(9Z)/18:3(6Z,9Z,12Z))[iso6] is considered to be a triradylglycerol lipid molecule. TG(18:1(9Z)/18:1(9Z)/18:3(6Z,9Z,12Z))[iso6] is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. TG(18:1(9Z)/18:1(9Z)/18:3(6Z,9Z,12Z))[iso6] can be biosynthesized from DG(18:1(9Z)/18:1(9Z)/0:0) and gamma-linolenoyl-CoA; which is mediated by the enzyme diacylglycerol O-acyltransferase. In cattle, TG(18:1(9Z)/18:1(9Z)/18:3(6Z,9Z,12Z))[iso6] is involved in the metabolic pathway called de novo triacylglycerol biosynthesis TG(18:1(9Z)/18:1(9Z)/18:3(6Z,9Z,12Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Oleoyl-2-oleoyl-3-g-linolenoyl-glycerolHMDB
1-Oleoyl-2-oleoyl-3-gamma-linolenoyl-glycerolHMDB
TAG(18:1/18:1/18:3)HMDB
TAG(18:1n9/18:1n9/18:3n6)HMDB
TAG(18:1W9/18:1W9/18:3W6)HMDB
TAG(54:5)HMDB
TG(18:1/18:1/18:3)HMDB
TG(18:1n9/18:1n9/18:3n6)HMDB
TG(18:1W9/18:1W9/18:3W6)HMDB
TG(54:5)HMDB
Tracylglycerol(18:1/18:1/18:3)HMDB
Tracylglycerol(18:1n9/18:1n9/18:3n6)HMDB
Tracylglycerol(18:1W9/18:1W9/18:3W6)HMDB
Tracylglycerol(54:5)HMDB
TriacylglycerolHMDB
TriglycerideHMDB
1-(9Z-Octadecenoyl)-2-(9Z-octadecenoyl)-3-(6Z,9Z,12Z-octadecatrienoyl)-glycerolHMDB
TG(18:1(9Z)/18:1(9Z)/18:3(6Z,9Z,12Z))Lipid Annotator
Chemical FormulaC57H100O6
Average Molecular Weight881.421
Monoisotopic Molecular Weight880.75199094
IUPAC Name(2S)-2,3-bis[(9Z)-octadec-9-enoyloxy]propyl (6Z,9Z,12Z)-octadeca-6,9,12-trienoate
Traditional Name(2S)-2,3-bis[(9Z)-octadec-9-enoyloxy]propyl (6Z,9Z,12Z)-octadeca-6,9,12-trienoate
CAS Registry NumberNot Available
SMILES
[H][C@](COC(=O)CCCCCCC\C=C/CCCCCCCC)(COC(=O)CCCC\C=C/C\C=C/C\C=C/CCCCC)OC(=O)CCCCCCC\C=C/CCCCCCCC
InChI Identifier
InChI=1S/C57H100O6/c1-4-7-10-13-16-19-22-25-28-31-34-37-40-43-46-49-55(58)61-52-54(63-57(60)51-48-45-42-39-36-33-30-27-24-21-18-15-12-9-6-3)53-62-56(59)50-47-44-41-38-35-32-29-26-23-20-17-14-11-8-5-2/h16,19,25-30,34,37,54H,4-15,17-18,20-24,31-33,35-36,38-53H2,1-3H3/b19-16-,28-25-,29-26-,30-27-,37-34-/t54-/m1/s1
InChI KeyGOEUQPTVSLNGLY-BFAXNOOESA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as triacylglycerols. These are glycerides consisting of three fatty acid chains covalently bonded to a glycerol molecule through ester linkages.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerolipids
Sub ClassTriradylcglycerols
Direct ParentTriacylglycerols
Alternative Parents
Substituents
  • Triacyl-sn-glycerol
  • Octadecanoid
  • Tricarboxylic acid or derivatives
  • Fatty acid ester
  • Fatty acyl
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Adiposome
  • Cell membrane
  • Membrane
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP10.77ALOGPS
logP19.78ChemAxon
logS-8.2ALOGPS
pKa (Strongest Basic)-6.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area78.9 ŲChemAxon
Rotatable Bond Count51ChemAxon
Refractivity274.48 m³·mol⁻¹ChemAxon
Polarizability115.35 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0000000090-9db9af1b2aed84ebe94dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0000000090-9db9af1b2aed84ebe94dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f7k-0000099070-39b7a9311373124338eaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000000090-1b2b1dfad3b8fbc5fac4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0000000090-1b2b1dfad3b8fbc5fac4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f79-0090009090-ee72742aa945b994bd2cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0000000090-b4dbb72e481480e64ab8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0000000090-b4dbb72e481480e64ab8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f7k-0030099070-42dd3cc7674a2454bdfeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0000000009-598f2b31b774a5935ca4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0000000009-598f2b31b774a5935ca4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-0000000009-598f2b31b774a5935ca4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001j-2120040490-eb3e9816481f7009902eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-066r-7190000820-c70bdd0e715a6965ed4bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-0191002100-575634ac227779e075f2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0075063090-29fe4066ef1292ca2369View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-066r-0019010000-9f1d2209609130a2574cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0arr-1089010000-678501041aa4f1095783View in MoNA
Biological Properties
Cellular Locations
  • Adiposome
  • Cell membrane
  • Membrane
Biospecimen Locations
  • All Tissues
  • Milk
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
All TissuesExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
MilkDetected and Quantified39 +/- 3 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified91 +/- 3 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified314 +/- 11 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified1.3 +/- 0.1 uMNot SpecifiedNot Specified
Normal		 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0010459
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB027610
KNApSAcK IDNot Available
Chemspider ID24768233
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53480523
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.

Enzymes

Enzyme Details
1. 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(18:1(9Z)/18:1(9Z)/0:0) + Gamma-linolenoyl-CoA → TG(18:1(9Z)/18:1(9Z)/18:3(6Z,9Z,12Z))[iso3] + Coenzyme Adetails