Showing metabocard for TG(16:0/18:1(9Z)/18:1(9Z))[iso3] (BMDB0005382)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:16:08 UTC
Update Date2020-06-04 20:34:16 UTC
BMDB IDBMDB0005382
Secondary Accession Numbers
  • BMDB05382
Metabolite Identification
Common NameTG(16:0/18:1(9Z)/18:1(9Z))[iso3]
DescriptionTG(16:0/18:1(9Z)/18:1(9Z))[iso3], also known as tag(16:0/18:1/18:1) or glycerol dioleate palmitate, 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. TG(16:0/18:1(9Z)/18:1(9Z))[iso3] is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). TG(16:0/18:1(9Z)/18:1(9Z))[iso3] can be biosynthesized from DG(16:0/18:1(9Z)/0:0) and oleoyl-CoA; which is mediated by the enzyme diacylglycerol O-acyltransferase. In cattle, TG(16:0/18:1(9Z)/18:1(9Z))[iso3] is involved in the metabolic pathway called de novo triacylglycerol biosynthesis TG(16:0/18:1(9Z)/18:1(9Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1,2-Di-(9Z)-octadecenoyl-3-hexadecanoylglycerolChEBI
1-Hexadecanoyl-2,3-di-(9Z)-octadecenoylglycerolChEBI
Glycerol dioleate palmitateChEBI
PalmitodioleinChEBI
Palmitoyl-dioleylglycerolChEBI
TAG(16:0/18:1/18:1)ChEBI
TAG(52:2)ChEBI
TG(16:0/18:1/18:1)ChEBI
TG(16:0/18:1omega9/18:1omega9)ChEBI
TG(52:2)ChEBI
Triacylglycerol(16:0/18:1/18:1)ChEBI
Triacylglycerol(16:0/18:1omega9/18:1omega9)ChEBI
Triacylglycerol(52:2)ChEBI
Triglyceride OOPChEBI
Triglyceride pooChEBI
Glycerol dioleic acid palmitic acidGenerator
1,2-DO-3PGMeSH
1-Palmitoyl-2-oleoyl-3-oleoyl-glycerolHMDB
TAG(16:0/18:1n9/18:1n9)HMDB
TAG(16:0/18:1W9/18:1W9)HMDB
TG(16:0/18:1n9/18:1n9)HMDB
TG(16:0/18:1W9/18:1W9)HMDB
Tracylglycerol(16:0/18:1/18:1)HMDB
Tracylglycerol(16:0/18:1n9/18:1n9)HMDB
Tracylglycerol(16:0/18:1W9/18:1W9)HMDB
Tracylglycerol(52:2)HMDB
TriacylglycerolHMDB
TriglycerideHMDB
1,2-Dioleoyl-3-palmitoylglycerolMeSH
Chemical FormulaC55H102O6
Average Molecular Weight859.3948
Monoisotopic Molecular Weight858.767640996
IUPAC Name1-(hexadecanoyloxy)-3-[(9Z)-octadec-9-enoyloxy]propan-2-yl (9Z)-octadec-9-enoate
Traditional Name1-(hexadecanoyloxy)-3-[(9Z)-octadec-9-enoyloxy]propan-2-yl (9Z)-octadec-9-enoate
CAS Registry Number27071-84-7
SMILES
CCCCCCCCCCCCCCCC(=O)OCC(COC(=O)CCCCCCC\C=C/CCCCCCCC)OC(=O)CCCCCCC\C=C/CCCCCCCC
InChI Identifier
InChI=1S/C55H102O6/c1-4-7-10-13-16-19-22-25-27-30-33-36-39-42-45-48-54(57)60-51-52(50-59-53(56)47-44-41-38-35-32-29-24-21-18-15-12-9-6-3)61-55(58)49-46-43-40-37-34-31-28-26-23-20-17-14-11-8-5-2/h25-28,52H,4-24,29-51H2,1-3H3/b27-25-,28-26-
InChI KeyJFISYPWOVQNHLS-LBXGSASVSA-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
  • 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 Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Adiposome
  • 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
logP10.74ALOGPS
logP19.98ChemAxon
logS-8ALOGPS
pKa (Strongest Basic)-6.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area78.9 ŲChemAxon
Rotatable Bond Count52ChemAxon
Refractivity261.93 m³·mol⁻¹ChemAxon
Polarizability114.61 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Adiposome
  • Cell membrane
  • Membrane
Biospecimen Locations
  • Milk
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
MilkDetected and Quantified668 +/- 6 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified1072 +/- 59 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified3094 +/- 208 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified26 +/- 4 uMNot SpecifiedNot Specified
Normal		 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0303020
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB007308
KNApSAcK IDNot Available
Chemspider ID13628595
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound25240174
PDB IDNot Available
ChEBI ID75848
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Tang C, Zhang K, Zhan T, Zhao Q, Zhang J: Metabolic Characterization of Dairy Cows Treated with Gossypol by Blood Biochemistry and Body Fluid Untargeted Metabolome Analyses. J Agric Food Chem. 2017 Oct 25;65(42):9369-9378. doi: 10.1021/acs.jafc.7b03544. Epub 2017 Oct 17. [PubMed:28965405 ]
  2. 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.