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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2019-07-23 05:44:16 UTC
HMDB IDHMDB0000548
Secondary Accession Numbers
  • HMDB00548
Metabolite Identification
Common NameTG(10:0/10:0/10:0)
DescriptionTG(10:0/10:0/10:0) or tricapric glyceride is a tridecanoic acid triglyceride or medium chain triglyceride. Triglycerides (TGs) are also known as triacylglycerols or triacylglycerides, meaning that they are glycerides in which the glycerol is esterified with three fatty acid groups (i.e. fatty acid tri-esters of glycerol). TGs may be divided into three general types with respect to their acyl substituents. They are simple or monoacid if they contain only one type of fatty acid, diacid if they contain two types of fatty acids and triacid if three different acyl groups. Chain lengths of the fatty acids in naturally occurring triglycerides can be of varying lengths and saturations but 16, 18 and 20 carbons are the most common. TG(10:0/10:0/10:0), in particular, consists of one chain of decanoic acid at the C-1 position, one chain of decanoic acid at the C-2 position and one chain of decanoic acid acid at the C-3 position. TGs are the main constituent of vegetable oil and animal fats. TGs are major components of very low density lipoprotein (VLDL) and chylomicrons, play an important role in metabolism as energy sources and transporters of dietary fat. They contain more than twice the energy (9 kcal/g) of carbohydrates and proteins. In the intestine, triglycerides are split into glycerol and fatty acids (this process is called lipolysis) with the help of lipases and bile secretions, which can then move into blood vessels. The triglycerides are rebuilt in the blood from their fragments and become constituents of lipoproteins, which deliver the fatty acids to and from fat cells among other functions. Various tissues can release the free fatty acids and take them up as a source of energy. Fat cells can synthesize and store triglycerides. When the body requires fatty acids as an energy source, the hormone glucagon signals the breakdown of the triglycerides by hormone-sensitive lipase to release free fatty acids. As the brain cannot utilize fatty acids as an energy source, the glycerol component of triglycerides can be converted into glucose for brain fuel when it is broken down. (www.cyberlipid.org, www.wikipedia.org). TAGs can serve as fatty acid stores in all cells, but primarily in adipocytes of adipose tissue. The major building block for the synthesis of triacylglycerides, in non-adipose tissue, is glycerol. Adipocytes lack glycerol kinase and so must use another route to TAG synthesis. Specifically, dihydroxyacetone phosphate (DHAP), which is produced during glycolysis, is the precursor for TAG synthesis in adipose tissue. DHAP can also serve as a TAG precursor in non-adipose tissues, but does so to a much lesser extent than glycerol. The use of DHAP for the TAG backbone depends on whether the synthesis of the TAGs occurs in the mitochondria and ER or the ER and the peroxisomes. The ER/mitochondria pathway requires the action of glycerol-3-phosphate dehydrogenase to convert DHAP to glycerol-3-phosphate. Glycerol-3-phosphate acyltransferase then esterifies a fatty acid to glycerol-3-phosphate thereby generating lysophosphatidic acid. The ER/peroxisome reaction pathway uses the peroxisomal enzyme DHAP acyltransferase to acylate DHAP to acyl-DHAP which is then reduced by acyl-DHAP reductase. The fatty acids that are incorporated into TAGs are activated to acyl-CoAs through the action of acyl-CoA synthetases. Two molecules of acyl-CoA are esterified to glycerol-3-phosphate to yield 1,2-diacylglycerol phosphate (also known as phosphatidic acid). The phosphate is then removed by phosphatidic acid phosphatase (PAP1), to generate 1,2-diacylglycerol. This diacylglycerol serves as the substrate for addition of the third fatty acid to make TAG. Intestinal monoacylglycerols, derived from dietary fats, can also serve as substrates for the synthesis of 1,2-diacylglycerols.
Structure
Data?1563860656
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
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.6e-05 g/LALOGPS
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 FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a59-3958000000-f57192615ab610f32defJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a59-3958000000-f57192615ab610f32defJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0a4i-0000190000-62ceec1552f50a5d7886JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a4i-0175090000-8c7de03a1649bbcb9482JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0089-9010000000-4e7483739c7dcb61b0bcJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-0a59-3958000000-f57192615ab610f32defJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0000090000-ce340e48f0c1c82582eaJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0000090000-ce340e48f0c1c82582eaJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-053r-0009070000-2c86bfc78962fbd6aa8dJSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
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
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. Troller JA, Bozeman MA: Isolation and characterization of a staphylococcal lipase. Appl Microbiol. 1970 Sep;20(3):480-4. [PubMed:5485729 ]
  2. Fujikawa H, Ibe A, Wauke T, Morozumi S, Mori H: Flavor production from edible oils and their constituents by Penicillium corylophilum. Shokuhin Eiseigaku Zasshi. 2002 Jun;43(3):160-4. [PubMed:12238154 ]
  3. Tetrick MA, Greer FR, Benevenga NJ: Blood D-(-)-3-hydroxybutyrate concentrations after oral administration of trioctanoin, trinonanoin, or tridecanoin to newborn rhesus monkeys (Macaca mulatta). Comp Med. 2010 Dec;60(6):486-90. [PubMed:21262136 ]
  4. Kuksis A, Stachnyk O, Holub BJ: Improved quantitation of plasma lipids by direct gas-liquid chromatography. J Lipid Res. 1969 Nov;10(6):660-7. [PubMed:5348124 ]
  5. Kuksis A, Marai L: Determination of the complete structure of natural lecithins. Lipids. 1967 May;2(3):217-24. [PubMed:17805770 ]
  6. Brasiello A, Crescitelli S, Milano G: Development of a coarse-grained model for simulations of tridecanoin liquid-solid phase transitions. Phys Chem Chem Phys. 2011 Oct 6;13(37):16618-28. doi: 10.1039/c1cp20604d. Epub 2011 Aug 22. [PubMed:21858376 ]
  7. Litchfield C, Miller E, Harlow RD, Reiser R: The triglyceride composition of 17 seed fats rich in octanoic, decanoic, or lauric acid. Lipids. 1967 Jul;2(4):345-50. [PubMed:17805764 ]
  8. Straarup EM, Danielsen V, Hoy CE, Jakobsen K: Dietary structured lipids for post-weaning piglets: fat digestibility, nitrogen retention and fatty acid profiles of tissues. J Anim Physiol Anim Nutr (Berl). 2006 Apr;90(3-4):124-35. [PubMed:16519757 ]
  9. Straarup EM, Hoy CE: Structured lipids improve fat absorption in normal and malabsorbing rats. J Nutr. 2000 Nov;130(11):2802-8. [PubMed:11053524 ]

Only showing the first 10 proteins. There are 26 proteins in total.

Enzymes

General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
PNLIP
Uniprot ID:
P16233
Molecular weight:
51156.48
General function:
Involved in catalytic activity
Specific function:
Hepatic lipase has the capacity to catalyze hydrolysis of phospholipids, mono-, di-, and triglycerides, and acyl-CoA thioesters. It is an important enzyme in HDL metabolism. Hepatic lipase binds heparin.
Gene Name:
LIPC
Uniprot ID:
P11150
Molecular weight:
55914.1
General function:
Involved in catalytic activity
Specific function:
May function as inhibitor of dietary triglyceride digestion. Lacks detectable lipase activity towards triglycerides, diglycerides, phosphatidylcholine, galactolipids or cholesterol esters (in vitro) (By similarity).
Gene Name:
PNLIPRP1
Uniprot ID:
P54315
Molecular weight:
Not Available
General function:
Involved in metabolic process
Specific function:
Multifunctional enzyme which has both triacylglycerol lipase and acylglycerol O-acyltransferase activities.
Gene Name:
PNPLA3
Uniprot ID:
Q9NST1
Molecular weight:
52864.64
General function:
Involved in lipid metabolic process
Specific function:
Not Available
Gene Name:
LIPF
Uniprot ID:
P07098
Molecular weight:
45237.375
General function:
Involved in catalytic activity
Specific function:
Has phospholipase and triglyceride lipase activities. Hydrolyzes high density lipoproteins (HDL) more efficiently than other lipoproteins. Binds heparin.
Gene Name:
LIPG
Uniprot ID:
Q9Y5X9
Molecular weight:
56794.275
General function:
Lipid transport and metabolism
Specific function:
Catalyzes fat and vitamin absorption. Acts in concert with pancreatic lipase and colipase for the complete digestion of dietary triglycerides.
Gene Name:
CEL
Uniprot ID:
P19835
Molecular weight:
79666.385
General function:
Involved in diacylglycerol O-acyltransferase activity
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. In liver, plays a role in esterifying exogenous fatty acids to glycerol. 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.
Gene Name:
DGAT1
Uniprot ID:
O75907
Molecular weight:
55277.735
General function:
Involved in catalytic activity
Specific function:
Lipase with broad substrate specificity. Can hydrolyze both phospholipids and galactolipids. Acts preferentially on monoglycerides, phospholipids and galactolipids. Contributes to milk fat hydrolysis.
Gene Name:
PNLIPRP2
Uniprot ID:
P54317
Molecular weight:
52077.475
General function:
Involved in catalytic activity
Specific function:
The primary function of this lipase is the hydrolysis of triglycerides of circulating chylomicrons and very low density lipoproteins (VLDL). Binding to heparin sulfate proteogylcans at the cell surface is vital to the function. The apolipoprotein, APOC2, acts as a coactivator of LPL activity in the presence of lipids on the luminal surface of vascular endothelium (By similarity).
Gene Name:
LPL
Uniprot ID:
P06858
Molecular weight:
53162.07

Transporters

General function:
Involved in lipid transporter activity
Specific function:
Catalyzes the transport of triglyceride, cholesteryl ester, and phospholipid between phospholipid surfaces. Required for the secretion of plasma lipoproteins that contain apolipoprotein B
Gene Name:
MTTP
Uniprot ID:
P55157
Molecular weight:
99350.3

Only showing the first 10 proteins. There are 26 proteins in total.