Showing metabocard for TG(18:0/18:0/18:0) (BMDB0005393)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-09-30 23:16:21 UTC
Update Date2020-05-21 16:27:45 UTC
BMDB IDBMDB0005393
Secondary Accession Numbers
  • BMDB05393
Metabolite Identification
Common NameTG(18:0/18:0/18:0)
DescriptionTG(18:0/18:0/18:0), also known as stearin or glyceryl tristearate, 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(18:0/18:0/18:0) is considered to be a triradylglycerol lipid molecule. TG(18:0/18:0/18:0) exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. TG(18:0/18:0/18:0) exists in all eukaryotes, ranging from yeast to humans. TG(18:0/18:0/18:0) can be biosynthesized from DG(18:0/18:0/0:0) and stearoyl-CoA through its interaction with the enzyme diacylglycerol O-acyltransferase. In cattle, TG(18:0/18:0/18:0) is involved in the metabolic pathway called de novo triacylglycerol biosynthesis TG(18:0/18:0/18:0) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2,3-Di(octadecanoyloxy)propyl octadecanoateChEBI
Glyceryl tristearateChEBI
Stearic acid triglycerin esterChEBI
StearinChEBI
TrioctadecanoinChEBI
TrioctadecanoylglycerolChEBI
TristearinChEBI
Tristearoyl-sn-glycerolChEBI
2,3-Di(octadecanoyloxy)propyl octadecanoic acidGenerator
Glyceryl tristearic acidGenerator
Stearate triglycerin esterGenerator
1-Stearoyl-2-stearoyl-3-stearoyl-glycerolHMDB
TAG(18:0/18:0/18:0)HMDB
TAG(54:0)HMDB
TG(54:0)HMDB
Tracylglycerol(18:0/18:0/18:0)HMDB
Tracylglycerol(54:0)HMDB
TriacylglycerolHMDB
TriglycerideHMDB
Stearic acid triglycerideHMDB
TristearoylglycerolHMDB
1-Octadecanoyl-2-octadecanoyl-3-octadecanoyl-glycerolHMDB
TG(18:0/18:0/18:0)Lipid Annotator
Chemical FormulaC57H110O6
Average Molecular Weight891.4797
Monoisotopic Molecular Weight890.830241252
IUPAC Name1,3-bis(octadecanoyloxy)propan-2-yl octadecanoate
Traditional Namestearin
CAS Registry Number555-43-1
SMILES
[H]C(COC(=O)CCCCCCCCCCCCCCCCC)(COC(=O)CCCCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCCCC
InChI Identifier
InChI=1S/C57H110O6/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/h54H,4-53H2,1-3H3
InChI KeyDCXXMTOCNZCJGO-UHFFFAOYSA-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 but not 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
logP10.68ALOGPS
logP21.59ChemAxon
logS-7.9ALOGPS
pKa (Strongest Basic)-6.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area78.9 ŲChemAxon
Rotatable Bond Count56ChemAxon
Refractivity268.9 m³·mol⁻¹ChemAxon
Polarizability122.4 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0aor-1268019000-bea2c9645ee3c4900166View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0aor-1268019000-bea2c9645ee3c4900166View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0aor-1268019000-bea2c9645ee3c4900166View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0aor-1268019000-bea2c9645ee3c4900166View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0000000009-2e72f9bb2fcaaf828b27View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0000000009-2e72f9bb2fcaaf828b27View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-0000009061-f9334cb97067aff8107cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-053i-0043006090-aeaea3ab6b0a4236072aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0bu0-0049003010-e3bfb827784335c5edd2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-2095012000-957fb0240d12665dad8eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0000000090-79fc8ab666c6e84b1368View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0000000090-79fc8ab666c6e84b1368View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dq-0090009090-e13cd3f8ab7c7e9c1b7bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-5120003390-7c67e17e3ae00ed1084fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0avi-9140102310-25b723724b97b6004b57View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014l-5397211000-3ff6387ac1ed487a7280View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0000000009-1ad7310063865c7c08aeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0000000009-1ad7310063865c7c08aeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-0010009061-4c61e1bfc065714b1855View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000000009-b360d413a092fefef62eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0000000009-b360d413a092fefef62eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-0000000009-b360d413a092fefef62eView in MoNA
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 22.53 MHz, CDCl3, experimental)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Adiposome
  • Cell membrane
  • Membrane
Biospecimen Locations
  • Milk
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
HMDB IDHMDB0005393
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB002912
KNApSAcK IDNot Available
Chemspider ID10673
KEGG Compound IDC00422
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkStearin
METLIN ID4701
PubChem Compound11146
PDB IDNot Available
ChEBI ID45956
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Mottram HR, Evershed RP: Elucidation of the composition of bovine milk fat triacylglycerols using high-performance liquid chromatography-atmospheric pressure chemical ionisation mass spectrometry. J Chromatogr A. 2001 Aug 17;926(2):239-53. [PubMed:11556330 ]
  2. 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 ]

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(18:0/18:0/0:0) + Stearoyl-CoA → TG(18:0/18:0/18:0) + Coenzyme Adetails