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

IdentificationTaxonomyPhysical propertiesSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:17:34 UTC
Update Date2020-06-04 20:30:47 UTC
MCDB ID BMDB0005453
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
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
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 30V, positivesplash10-000i-0000000090-91d6e8bb3820a2b9ebde2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 46V, positivesplash10-000i-0025004090-32e831ad9bb94e6569652020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 61V, positivesplash10-00kr-4689024020-7527d97fb03536363c5b2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 77V, positivesplash10-00lb-6942000000-37f17691e5732c6d232b2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 93V, positivesplash10-000t-7920000000-8d53f79404c44a257cbc2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 109V, positivesplash10-0532-9800000000-5ddd79d8af2c416bab4d2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 123V, positivesplash10-0532-9700000000-e96406e89785ef71e7112020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 61V, positivesplash10-0udi-0000019030-5f72f64cb14b990252632020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 61V, positivesplash10-03di-0158960000-bad288273f5f0ef006e82020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 61V, positivesplash10-00or-0054190000-2d9cb5e1963a459c88302020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 61V, positivesplash10-0002-3940000000-daf7601cc0abe13d83fa2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 31V, positivesplash10-0udi-0000009000-6d75632a4c7e9871410c2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 42V, positivesplash10-0uxr-5671009000-a4a6beef3d7f47884d902020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 53V, positivesplash10-015a-9830001000-493c7832f4a4288ca5192020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 63V, positivesplash10-00l2-9510000000-48886ae654cd58f8e05d2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 74V, positivesplash10-05o1-9400000000-50d3f5f119ff86e93d722020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 84V, positivesplash10-05o1-9300000000-c9f83ff0d877bf07548b2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 95V, positivesplash10-067j-9200000000-362946f8ec43e2da1de62020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 106V, positivesplash10-067j-9100000000-3cbc32304732b7cd617e2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 127V, positivesplash10-067i-9100000000-975bad5ee71e2769d5a62020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 61V, positivesplash10-014i-0094041000-972891f073da867b33192020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 61V, positivesplash10-0072-2900000000-23da0caf841c568c59202020-07-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0000000009-7ebc474373ce1c8c33882017-10-04View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0000000009-7ebc474373ce1c8c33882017-10-04View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udr-0000009061-c361cdac983d0cdffd592017-10-04View Spectrum
1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)Not Available2016-09-19View Spectrum
Concentrations
StatusValueReferenceDetails
Detected and Quantified164 +/- 12 uM details
Detected and Quantified230 +/- 16 uM details
Detected and Quantified738 +/- 17 uM details
Detected and Quantified7.6 +/- 0.2 uM details
HMDB IDHMDB0005453
DrugBank IDDB13038
Phenol Explorer Compound IDNot Available
FoodDB 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)Download (PDF)
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.