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Record Information
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-12-20 21:14:44 UTC
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. (, 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.
1,2,3-Propanol tridecanoateChEBI
Capric acid triglycerideChEBI
Capric triglycerideChEBI
Decanoic acid, 1,2,3-propanetriyl esterChEBI
Glycerin tridecanoateChEBI
Glycerol tricaprateChEBI
Glycerol tridecanoateChEBI
Glyceryl tricaprateChEBI
Glyceryl tridecanoateChEBI
TG 10:0/10:0/10:0ChEBI
Tricapric glycerideChEBI
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
1,2, 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
1-animal fats-2-animal fats-3-animal fats-glycerolLipid Annotator
1-decanoic acid-2-decanoic acid-3-decanoic acid-glycerolLipid Annotator
TAG(10:0/10:0/10:0)Lipid Annotator
TriacylglycerolLipid Annotator
Tracylglycerol(30:0)Lipid Annotator
TriglycerideLipid Annotator
Tracylglycerol(10:0/10:0/10:0)Lipid Annotator
TAG(30:0)Lipid Annotator
TG(30:0)Lipid Annotator
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
InChI Identifier
Chemical Taxonomy
DescriptionThis compound 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
Sub ClassTriradylcglycerols
Direct ParentTriacylglycerols
Alternative Parents
  • 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

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Physical Properties
Experimental Properties
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
Water Solubility1.6e-05 g/LALOGPS
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
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a59-3958000000-f57192615ab610f32defView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0a4i-0000190000-62ceec1552f50a5d7886View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a4i-0175090000-8c7de03a1649bbcb9482View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0089-9010000000-4e7483739c7dcb61b0bcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-0a59-3958000000-f57192615ab610f32defView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0000090000-ce340e48f0c1c82582eaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0000090000-ce340e48f0c1c82582eaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-053r-0009070000-2c86bfc78962fbd6aa8dView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biofluid LocationsNot Available
Tissue LocationNot Available
De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/10:0)ThumbThumb?image type=greyscaleThumb?image type=simpleNot Available
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
PubChem Compound69310
PDB IDNot Available
ChEBI ID77388
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.


General function:
Involved in lipid metabolic process
Specific function:
Not Available
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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.
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Involved in catalytic activity
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Not Available
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Lipid transport and metabolism
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Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Hydrolyzes aromatic and aliphatic esters, but has no catalytic activity toward amides or a fatty acyl-CoA ester. Hydrolyzes the methyl ester group of cocaine to form benzoylecgonine. Catalyzes the transesterification of cocaine to form cocaethylene. Displays fatty acid ethyl ester synthase activity, catalyzing the ethyl esterification of oleic acid to ethyloleate.
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Involved in metabolic process
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Catalyzes the initial step in triglyceride hydrolysis in adipocyte and non-adipocyte lipid droplets. Also has acylglycerol transacylase activity. May act coordinately with LIPE/HLS within the lipolytic cascade. Regulates adiposome size and may be involved in the degradation of adiposomes. May play an important role in energy homeostasis. May play a role in the response of the organism to starvation, enhancing hydrolysis of triglycerides and providing free fatty acids to other tissues to be oxidized in situations of energy depletion.
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General function:
Involved in catalytic activity
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Not Available
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General function:
Involved in transferase activity, transferring acyl groups other than amino-acyl groups
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Essential acyltransferase that catalyzes the terminal and only committed step in triacylglycerol synthesis by using diacylglycerol and fatty acyl CoA as substrates. Required for synthesis and storage of intracellular triglycerides. Probably plays a central role in cytosolic lipid accumulation. In liver, is primarily responsible for incorporating endogenously synthesized fatty acids into triglycerides (By similarity). Functions also as an acyl-CoA retinol acyltransferase (ARAT).
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Involved in diacylglycerol O-acyltransferase activity
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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.
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Involved in transferase activity, transferring acyl groups other than amino-acyl groups
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Catalyzes the formation of diacylglycerol from 2-monoacylglycerol and fatty acyl-CoA. Also able to catalyze the terminal step in triacylglycerol synthesis by using diacylglycerol and fatty acyl-CoA as substrates. Has a preference toward palmitoyl-CoA and oleoyl-CoA. May be involved in absorption of dietary fat in the small intestine by catalyzing the resynthesis of triacylglycerol in enterocytes.
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Involved in metabolic process
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Multifunctional enzyme which has both triacylglycerol lipase and acylglycerol O-acyltransferase activities.
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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
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Only showing the first 10 proteins. There are 26 proteins in total.