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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:40:53 UTC
Update Date2022-03-07 02:52:49 UTC
HMDB IDHMDB0031089
Secondary Accession Numbers
  • HMDB31089
Metabolite Identification
Common NameGlycerol triundecanoate
DescriptionGlycerol triundecanoate 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. Based on a literature review a significant number of articles have been published on Glycerol triundecanoate.
Structure
Data?1563862080
Synonyms
ValueSource
Glycerol triundecanoic acidGenerator
1,2,3-Propanetriyl undecanoate, 9ciHMDB
1,2,3-TriundecanoylglycerolHMDB
Captex 8227HMDB
Glyceryl triundecanoateHMDB
N-TrihendecanoinHMDB
Propane-1,2,3-triyl triundecanoateHMDB
Tri-undecanoinHMDB
TrihendecanoinHMDB
TriundecanoinHMDB
TriundecylinHMDB
Undecanoic acid, 1,1',1''-(1,2,3-propanetriyl) esterHMDB
Undecanoic acid, 1,2,3-propanetriyl esterHMDB
1,3-Bis(undecanoyloxy)propan-2-yl undecanoic acidGenerator
Chemical FormulaC36H68O6
Average Molecular Weight596.9215
Monoisotopic Molecular Weight596.501589908
IUPAC Name1,3-bis(undecanoyloxy)propan-2-yl undecanoate
Traditional Nametriundecanoin
CAS Registry Number13552-80-2
SMILES
CCCCCCCCCCC(=O)OCC(COC(=O)CCCCCCCCCC)OC(=O)CCCCCCCCCC
InChI Identifier
InChI=1S/C36H68O6/c1-4-7-10-13-16-19-22-25-28-34(37)40-31-33(42-36(39)30-27-24-21-18-15-12-9-6-3)32-41-35(38)29-26-23-20-17-14-11-8-5-2/h33H,4-32H2,1-3H3
InChI KeyMBXVIRZWSHICAV-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 DescriptorsNot Available
Ontology
Physiological effect
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point31.2 °CNot Available
Boiling Point611.60 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility3.9e-10 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP13.972 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.4e-05 g/LALOGPS
logP9.33ALOGPS
logP12.26ChemAxon
logS-7.6ALOGPS
pKa (Strongest Basic)-6.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area78.9 ŲChemAxon
Rotatable Bond Count35ChemAxon
Refractivity172.28 m³·mol⁻¹ChemAxon
Polarizability78.21 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+242.98631661259
DarkChem[M-H]-235.93931661259
DeepCCS[M+H]+259.49630932474
DeepCCS[M-H]-256.57130932474
DeepCCS[M-2H]-291.42930932474
DeepCCS[M+Na]+266.78530932474
AllCCS[M+H]+266.432859911
AllCCS[M+H-H2O]+266.032859911
AllCCS[M+NH4]+266.832859911
AllCCS[M+Na]+266.932859911
AllCCS[M-H]-242.732859911
AllCCS[M+Na-2H]-246.532859911
AllCCS[M+HCOO]-250.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Glycerol triundecanoateCCCCCCCCCCC(=O)OCC(COC(=O)CCCCCCCCCC)OC(=O)CCCCCCCCCC4577.1Standard polar33892256
Glycerol triundecanoateCCCCCCCCCCC(=O)OCC(COC(=O)CCCCCCCCCC)OC(=O)CCCCCCCCCC3752.0Standard non polar33892256
Glycerol triundecanoateCCCCCCCCCCC(=O)OCC(COC(=O)CCCCCCCCCC)OC(=O)CCCCCCCCCC4059.7Semi standard non polar33892256
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycerol triundecanoate 10V, Positive-QTOFsplash10-03di-0000009000-30e916903ee5e981141b2017-10-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycerol triundecanoate 20V, Positive-QTOFsplash10-03di-0000009000-30e916903ee5e981141b2017-10-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycerol triundecanoate 40V, Positive-QTOFsplash10-03dj-0000961000-f75fae0b79e1427d66732017-10-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycerol triundecanoate 10V, Positive-QTOFsplash10-03di-0000009000-2d2d79ae6f09f26f98902021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycerol triundecanoate 20V, Positive-QTOFsplash10-03di-0000009000-2d2d79ae6f09f26f98902021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycerol triundecanoate 40V, Positive-QTOFsplash10-03dj-0100961000-9a36feeee801d485ed022021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycerol triundecanoate 10V, Positive-QTOFsplash10-0002-0100190000-26fc805ae0b2afd1e7602021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycerol triundecanoate 20V, Positive-QTOFsplash10-014j-4901470000-fbc3f2a5dccbbd4fefa42021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycerol triundecanoate 40V, Positive-QTOFsplash10-0aos-9630100000-f6a440b189c208bda4382021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycerol triundecanoate 10V, Negative-QTOFsplash10-0002-0412490000-49e07694fd392510da1a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycerol triundecanoate 20V, Negative-QTOFsplash10-01pa-0950330000-69faa2189fc7cfca923d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycerol triundecanoate 40V, Negative-QTOFsplash10-01p9-0950300000-ecbf3e7dfd145a97c8ea2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycerol triundecanoate 10V, Positive-QTOFsplash10-014i-0000009000-8ea783391d20226c49cb2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycerol triundecanoate 20V, Positive-QTOFsplash10-014i-0000009000-8ea783391d20226c49cb2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycerol triundecanoate 40V, Positive-QTOFsplash10-014i-0000009000-8ea783391d20226c49cb2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycerol triundecanoate 10V, Positive-QTOFsplash10-0udi-0000009000-f0c1c15cb4e0ef240a4a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycerol triundecanoate 20V, Positive-QTOFsplash10-0udi-0000009000-f0c1c15cb4e0ef240a4a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycerol triundecanoate 40V, Positive-QTOFsplash10-0vi6-0900909000-75cb49a4829c7ea595e92021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB003094
KNApSAcK IDNot Available
Chemspider ID75404
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound83574
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1300291
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Pi-Sunyer FX, Conway JM, Lavau M, Campbell G, Eisenstein AB: Glucagon, insulin, and gluconeogenesis in fasted odd carbon fatty acid-enriched rats. Am J Physiol. 1976 Aug;231(2):366-9. [PubMed:961887 ]
  2. Pi-Sunyer FX: Resistance to ketosis during prolonged fasting by rats fed on a diet containing undecanoic acid, an odd-carbon-number fatty acid. Br J Nutr. 1976 Jan;35(1):41-6. [PubMed:1244841 ]
  3. Johnson W Jr: Final report on the safety assessment of trilaurin, triarachidin, tribehenin, tricaprin, tricaprylin, trierucin, triheptanoin, triheptylundecanoin, triisononanoin, triisopalmitin, triisostearin, trilinolein, trimyristin, trioctanoin, triolein, tripalmitin, tripalmitolein, triricinolein, tristearin, triundecanoin, glyceryl triacetyl hydroxystearate, glyceryl triacetyl ricinoleate, and glyceryl stearate diacetate. Int J Toxicol. 2001;20 Suppl 4:61-94. [PubMed:11800053 ]
  4. Dryden LP, Bitman J, Wrenn TR, Weyant JR, Miller RW, Edmondson LF: Effect of triundecanoin upon lipid metabolism in the cow. J Am Oil Chem Soc. 1974 Jul;51(7):302-6. [PubMed:4858621 ]
  5. Hartman AD: Adipocyte fatty acid mobilization in vivo: effects of age and anatomical location. Lipids. 1985 May;20(5):255-61. [PubMed:4010482 ]
  6. VanItallie TB, Khachadurian AK: Rats enriched with odd-carbon fatty acids: maintenance of liver glycogen during starvation. Science. 1969 Aug 22;165(3895):811-3. [PubMed:5796557 ]
  7. Bitman J, Weyant JR, Wood DL, Wrenn TR: Necessity of vitamin B12 for growth of rats fed on an odd- or even-carbon-number fat. Br J Nutr. 1978 May;39(3):615-26. [PubMed:638128 ]
  8. Kim S, Pi-Sunyer FX: Diminished ketosis and triglyceridemia during fasting in odd-carbon enriched pregnant rats. Endocrinology. 1977 Feb;100(2):373-9. [PubMed:832630 ]
  9. Anderson RL, Boggs RW: Glucogenic and ketogenic capacities of lard, safflower oil, and triumdecanoin in fasting rats. J Nutr. 1975 Feb;105(2):185-9. [PubMed:1113198 ]
  10. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  11. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  12. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  13. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  14. Ghosh S, Strum JC, Bell RM: Lipid biochemistry: functions of glycerolipids and sphingolipids in cellular signaling. FASEB J. 1997 Jan;11(1):45-50. [PubMed:9034165 ]
  15. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  16. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
  17. Linda T. Welson (2006). Triglycerides and Cholesterol Research. Nova Science Publishers Inc..