Showing metabocard for TG(18:1(9Z)/18:1(9Z)/18:1(9Z))[iso] (BMDB0005453)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-09-30 23:17:34 UTC
Update Date2020-06-04 20:30:47 UTC
BMDB IDBMDB0005453
Secondary Accession Numbers
  • BMDB05453
Metabolite Identification
Common NameTG(18:1(9Z)/18:1(9Z)/18:1(9Z))[iso]
DescriptionTG(18:1(9Z)/18:1(9Z)/18:1(9Z)), also known as glycerol triolein or oleic acid triglyceride, 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)/18:1(9Z)) is considered to be a triradylglycerol lipid molecule. TG(18:1(9Z)/18:1(9Z)/18:1(9Z)) exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. TG(18:1(9Z)/18:1(9Z)/18:1(9Z)) exists in all eukaryotes, ranging from yeast to humans. In cattle, TG(18:1(9Z)/18:1(9Z)/18:1(9Z)) is involved in the metabolic pathway called de novo triacylglycerol biosynthesis TG(18:1(9Z)/18:1(9Z)/18:1(9Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(Z)-9-Octadecenoic acid, 1,2,3-propanetriyl esterChEBI
1,2,3-Tri-(9Z-octadecenoyl)-glycerolChEBI
Glycerin trioleateChEBI
Glycerol trioleateChEBI
Glycerol trioleinChEBI
Glycerol, tri(cis-9-octadecenoate)ChEBI
Glyceryl trioleateChEBI
Glyceryl-1,2,3-trioleateChEBI
Oleic acid triglycerideChEBI
Oleic triglycerideChEBI
OleinChEBI
Oleyl triglycerideChEBI
Propane-1,2,3-triyl (9Z,9'z,9''z)tris-octadec-9-enoateChEBI
TG(18:1(9Z)/18:1(9Z)/18:1(9Z))[iso]ChEBI
TrioleoylglycerideChEBI
TrioleoylglycerolChEBI
(Z)-9-Octadecenoate, 1,2,3-propanetriyl esterGenerator
Glycerin trioleic acidGenerator
Glycerol trioleic acidGenerator
Glycerol, tri(cis-9-octadecenoic acid)Generator
Glyceryl trioleic acidGenerator
Glyceryl-1,2,3-trioleic acidGenerator
Oleate triglycerideGenerator
Propane-1,2,3-triyl (9Z,9'z,9''z)tris-octadec-9-enoic acidGenerator
TrielaidinHMDB
Trioleate glycerinHMDB
Trioleyl glycerolHMDB
Glycerol, trioleylHMDB
Trioleate, glycerolHMDB
Trioleate-glycerinHMDB
TriacylglycerolHMDB
TG(18:1/18:1/18:1)HMDB
TG(54:3)HMDB
Tracylglycerol(18:1/18:1/18:1)HMDB
TriglycerideHMDB
Tracylglycerol(54:3)HMDB
1-Oleoyl-2-oleoyl-3-oleoyl-glycerolHMDB
TAG(54:3)HMDB
1-(9Z-Octadecenoyl)-2-(9Z-octadecenoyl)-3-(9Z-octadecenoyl)-glycerolHMDB
TAG(18:1/18:1/18:1)HMDB
TG(18:1(9Z)/18:1(9Z)/18:1(9Z))Lipid Annotator
TrioleinMeSH
Chemical FormulaC57H104O6
Average Molecular Weight885.4321
Monoisotopic Molecular Weight884.78329106
IUPAC Name1,3-bis[(9Z)-octadec-9-enoyloxy]propan-2-yl (9Z)-octadec-9-enoate
Traditional Nametriolein
CAS Registry Number122-32-7
SMILES
[H]C(COC(=O)CCCCCCC\C=C/CCCCCCCC)(COC(=O)CCCCCCC\C=C/CCCCCCCC)OC(=O)CCCCCCC\C=C/CCCCCCCC
InChI Identifier
InChI=1S/C57H104O6/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/h25-30,54H,4-24,31-53H2,1-3H3/b28-25-,29-26-,30-27-
InChI KeyPHYFQTYBJUILEZ-IUPFWZBJSA-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
StateLiquid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP10.82ALOGPS
logP20.51ChemAxon
logS-8.2ALOGPS
pKa (Strongest Basic)-6.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area78.9 ŲChemAxon
Rotatable Bond Count53ChemAxon
Refractivity272.25 m³·mol⁻¹ChemAxon
Polarizability116.96 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 30V, positivesplash10-000i-0000000090-91d6e8bb3820a2b9ebdeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 46V, positivesplash10-000i-0025004090-32e831ad9bb94e656965View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 61V, positivesplash10-00kr-4689024020-7527d97fb03536363c5bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 77V, positivesplash10-00lb-6942000000-37f17691e5732c6d232bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 93V, positivesplash10-000t-7920000000-8d53f79404c44a257cbcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 109V, positivesplash10-0532-9800000000-5ddd79d8af2c416bab4dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 123V, positivesplash10-0532-9700000000-e96406e89785ef71e711View in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 61V, positivesplash10-0udi-0000019030-5f72f64cb14b99025263View in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 61V, positivesplash10-03di-0158960000-bad288273f5f0ef006e8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 61V, positivesplash10-00or-0054190000-2d9cb5e1963a459c8830View in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 61V, positivesplash10-0002-3940000000-daf7601cc0abe13d83faView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 31V, positivesplash10-0udi-0000009000-6d75632a4c7e9871410cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 42V, positivesplash10-0uxr-5671009000-a4a6beef3d7f47884d90View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 53V, positivesplash10-015a-9830001000-493c7832f4a4288ca519View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 63V, positivesplash10-00l2-9510000000-48886ae654cd58f8e05dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 74V, positivesplash10-05o1-9400000000-50d3f5f119ff86e93d72View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 84V, positivesplash10-05o1-9300000000-c9f83ff0d877bf07548bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 95V, positivesplash10-067j-9200000000-362946f8ec43e2da1de6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 106V, positivesplash10-067j-9100000000-3cbc32304732b7cd617eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 127V, positivesplash10-067i-9100000000-975bad5ee71e2769d5a6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 61V, positivesplash10-014i-0094041000-972891f073da867b3319View in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 61V, positivesplash10-0072-2900000000-23da0caf841c568c5920View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0000000009-7ebc474373ce1c8c3388View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0000000009-7ebc474373ce1c8c3388View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udr-0000009061-c361cdac983d0cdffd59View in MoNA
1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Adiposome
  • Cell membrane
  • Membrane
Biospecimen Locations
  • Milk
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
MilkDetected and Quantified164 +/- 12 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified230 +/- 16 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified738 +/- 17 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified7.6 +/- 0.2 uMNot SpecifiedNot Specified
Normal		 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0005453
DrugBank IDDB13038
Phenol Explorer Compound IDNot Available
FooDB IDFDB094046
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDCPD-11691
BiGG IDNot Available
Wikipedia LinkTriolein
METLIN IDNot Available
PubChem Compound5497163
PDB IDNot Available
ChEBI ID53753
References
Synthesis ReferenceDesnuelle, P.; Naudet, M. Isomerization of oleic acid during the synthesis of triolein. Bull. soc. chim. (1945), 12 998-1001. CAN 40:19192 AN 1946:19192 CAPLUS
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) + Oleoyl-CoA → TG(18:1(9Z)/18:1(9Z)/18:1(9Z))[iso] + Coenzyme Adetails