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Record Information
Version1.0
Creation Date2016-09-30 22:32:35 UTC
Update Date2020-04-21 18:15:55 UTC
MCDB ID BMDB0000548
Secondary Accession Numbers
  • BMDB00548
Metabolite Identification
Common NameTG(10:0/10:0/10:0)[iso]
DescriptionTG(10:0/10:0/10:0), also known as caprin or glycerol tridecanoate, 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(10:0/10:0/10:0) is considered to be a triradylglycerol lipid molecule. TG(10:0/10:0/10:0) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. TG(10:0/10:0/10:0) exists in all eukaryotes, ranging from yeast to humans. TG(10:0/10:0/10:0) can be biosynthesized from DG(10:0/10:0/0:0) and decanoyl-CoA; which is catalyzed by the enzyme diacylglycerol O-acyltransferase. In cattle, TG(10:0/10:0/10:0) is involved in the metabolic pathway called de novo triacylglycerol biosynthesis TG(10:0/10:0/10:0) pathway.
Structure
Thumb
Synonyms
ValueSource
1,2,3-Propanol tridecanoateChEBI
1,2,3-TridecanoylglycerolChEBI
Capric acid triglycerideChEBI
Capric triglycerideChEBI
CaprinChEBI
Decanoic acid, 1,2,3-propanetriyl esterChEBI
Glycerin tridecanoateChEBI
Glycerol tricaprateChEBI
Glycerol tridecanoateChEBI
Glyceryl tricaprateChEBI
Glyceryl tridecanoateChEBI
TG 10:0/10:0/10:0ChEBI
Tri-N-caprinChEBI
Tricapric glycerideChEBI
TridecanoinChEBI
TridecanoylglycerolChEBI
1,2,3-Propanol tridecanoic acidGenerator
Caprate triglycerideGenerator
Decanoate, 1,2,3-propanetriyl esterGenerator
Glycerin tridecanoic acidGenerator
Glycerol tricapric acidGenerator
Glycerol tridecanoic acidGenerator
Glyceryl tricapric acidGenerator
Glyceryl tridecanoic acidGenerator
1-Animal fats-2-animal fats-3-animal fats-glycerolHMDB
1-Decanoic acid-2-decanoic acid-3-decanoic acid-glycerolHMDB
TAG(10:0/10:0/10:0)HMDB
TriacylglycerolHMDB
Tracylglycerol(30:0)HMDB
TriglycerideHMDB
Tracylglycerol(10:0/10:0/10:0)HMDB
TAG(30:0)HMDB
TG(30:0)HMDB
1,2, 3-Propanetriyl-decanoateHMDB
1,2, 3-Propanetriyl-decanoic acidHMDB
2,3-Bis(decanoyloxy)propyl decanoateHMDB
2,3-Bis(decanoyloxy)propyl decanoate (acd/name 4.0)HMDB
2,3-Bis(decanoyloxy)propyl decanoic acidHMDB
Glycerol tricaprinHMDB
Tri-decanoinHMDB
TricaprinHMDB
TG(10:0/10:0/10:0)Lipid Annotator, ChEBI
Chemical FormulaC33H62O6
Average Molecular Weight554.853
Monoisotopic Molecular Weight554.454639716
IUPAC Name1,3-bis(decanoyloxy)propan-2-yl decanoate
Traditional Nametricaprin
CAS Registry Number621-71-6
SMILES
[H]C(COC(=O)CCCCCCCCC)(COC(=O)CCCCCCCCC)OC(=O)CCCCCCCCC
InChI Identifier
InChI=1S/C33H62O6/c1-4-7-10-13-16-19-22-25-31(34)37-28-30(39-33(36)27-24-21-18-15-12-9-6-3)29-38-32(35)26-23-20-17-14-11-8-5-2/h30H,4-29H2,1-3H3
InChI KeyLADGBHLMCUINGV-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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP8.78ALOGPS
logP10.92ChemAxon
logS-7.5ALOGPS
pKa (Strongest Basic)-6.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area78.9 ŲChemAxon
Rotatable Bond Count32ChemAxon
Refractivity158.47 m³·mol⁻¹ChemAxon
Polarizability70.75 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a59-3958000000-f57192615ab610f32def2017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a59-3958000000-f57192615ab610f32def2018-05-18View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0a4i-0000190000-62ceec1552f50a5d78862012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a4i-0175090000-8c7de03a1649bbcb94822012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0089-9010000000-4e7483739c7dcb61b0bc2012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-0a59-3958000000-f57192615ab610f32def2012-08-31View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0000090000-ce340e48f0c1c82582ea2017-10-04View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0000090000-ce340e48f0c1c82582ea2017-10-04View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-053r-0009070000-2c86bfc78962fbd6aa8d2017-10-04View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000090000-2a5a4f209f02f40b110f2021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0000090000-2a5a4f209f02f40b110f2021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03ii-0909090000-c6a9641978779d1182b02021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ue9-0527090000-00cdfe845f15d4b6a6612021-09-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000t-0933010000-de250ac1d1f0d8fcdca22021-09-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00dj-0912000000-3aa31014b1eb3b307c922021-09-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0000090000-add7d9098153c7a00e9a2021-09-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0000090000-add7d9098153c7a00e9a2021-09-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-0000090000-add7d9098153c7a00e9a2021-09-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0102090000-747370baaa832594f1b22021-09-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a59-5727790000-91d904d103a37903b33b2021-09-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0bu0-3591100000-2da6107e763a64b2df762021-09-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0000090000-d6cd7cf63c9fb0b8a2662021-09-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0000090000-d6cd7cf63c9fb0b8a2662021-09-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-053r-0109070000-6b4138a13a27d3e873082021-09-25View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)Not Available2012-12-04View Spectrum
1D NMR1H NMR Spectrum (1D, CDCl3, experimental)Not Available2016-10-22View Spectrum
1D NMR13C NMR Spectrum (1D, CDCl3, experimental)Not Available2016-10-22View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)Not Available2022-08-21View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Not Available2022-08-21View Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)Not Available2022-08-21View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Not Available2022-08-21View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)Not Available2022-08-21View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Not Available2022-08-21View Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)Not Available2022-08-21View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Not Available2022-08-21View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)Not Available2022-08-21View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Not Available2022-08-21View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)Not Available2022-08-21View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Not Available2022-08-21View Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)Not Available2022-08-21View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Not Available2022-08-21View Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)Not Available2022-08-21View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Not Available2022-08-21View Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)Not Available2022-08-21View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Not Available2022-08-21View Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)Not Available2022-08-21View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Not Available2022-08-21View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)Not Available2012-12-05View Spectrum
Concentrations
StatusValueReferenceDetails
Detected but not QuantifiedNot Applicable details
HMDB IDHMDB0000548
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB003134
KNApSAcK IDNot Available
Chemspider ID62521
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5532
PubChem Compound69310
PDB IDNot Available
ChEBI ID77388
References
Synthesis ReferenceSelmi, B.; Gontier, E.; Ergan, F.; Thomas, D. Effects of fatty acid chain length and unsaturation number on triglyceride synthesis catalyzed by immobilized lipase in solvent-free medium. Enzyme and Microbial Technology (1998), 23(3/4), 182-186.
Material Safety Data Sheet (MSDS)Download (PDF)
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 ]