You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
Creation Date2008-11-04 14:19:10 UTC
Update Date2017-09-27 08:26:27 UTC
HMDB IDHMDB0011187
Secondary Accession Numbers
  • HMDB11187
Metabolite Identification
Common NameTG(8:0/8:0/8:0)
DescriptionTG(8:0/8:0/8:0) belongs to the family of triradyglycerols, which are glycerolipids lipids containing a common glycerol backbone to which at least one fatty acyl group is esterified. Their general formula is [R1]OCC(CO[R2])O[R3]. TG(8:0/8:0/8:0) is made up of one octanoyl(R1), one octanoyl(R2), and one octanoyl(R3).
Structure
Thumb
Synonyms
ValueSource
1,2,3-Propanetriol trioctanoateChEBI
1,2,3-TrioctanoylglycerolChEBI
AxonaChEBI
Caprylic acid triglycerideChEBI
Caprylic acid, 1,2,3-propanetriyl esterChEBI
Caprylic triglycerideChEBI
CaprylinChEBI
Glycerin tricaprylateChEBI
Glycerol tricaprylateChEBI
Glycerol trioctanoateChEBI
Glycerol trioctanoinChEBI
Glyceryl tricaprylateChEBI
Octanoic acid triglycerideChEBI
Octanoic acid, 1,1',1''-(1,2,3-propanetriyl) esterChEBI
Octanoic acid, 1,2,3-propanetriyl esterChEBI
TG(8:0/8:0/8:0)ChEBI
TricaprilinChEBI
Tricaprylic glycerideChEBI
TricaprylinChEBI
TricapryloylglycerolChEBI
Tricaprylyl glycerinChEBI
TrioctanoylglycerideChEBI
TrioctanoylglycerolChEBI
1,2,3-Propanetriol trioctanoic acidGenerator
Caprylate triglycerideGenerator
Caprylate, 1,2,3-propanetriyl esterGenerator
Glycerin tricaprylic acidGenerator
Glycerol tricaprylic acidGenerator
Glycerol trioctanoic acidGenerator
Glyceryl tricaprylic acidGenerator
Octanoate triglycerideGenerator
Octanoate, 1,1',1''-(1,2,3-propanetriyl) esterGenerator
Octanoate, 1,2,3-propanetriyl esterGenerator
Panasate 800MeSH
Glyceryl trioctanoateMeSH
1-capryloyl-2-capryloyl-3-capryloyl-glycerolLipid Annotator
TAG(8:0/8:0/8:0)Lipid Annotator
TAG(24:0)Lipid Annotator
Tracylglycerol(24:0)Lipid Annotator
TriacylglycerolLipid Annotator
TriglycerideLipid Annotator
TG(24:0)Lipid Annotator
1-octanoyl-2-octanoyl-3-octanoyl-glycerolLipid Annotator
Tracylglycerol(8:0/8:0/8:0)Lipid Annotator
Chemical FormulaC27H50O6
Average Molecular Weight470.6823
Monoisotopic Molecular Weight470.360739332
IUPAC Name1,3-bis(octanoyloxy)propan-2-yl octanoate
Traditional NameRato
CAS Registry NumberNot Available
SMILES
[H]C(COC(=O)CCCCCCC)(COC(=O)CCCCCCC)OC(=O)CCCCCCC
InChI Identifier
InChI=1S/C27H50O6/c1-4-7-10-13-16-19-25(28)31-22-24(33-27(30)21-18-15-12-9-6-3)23-32-26(29)20-17-14-11-8-5-2/h24H,4-23H2,1-3H3
InChI KeyVLPFTAMPNXLGLX-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as triacylglycerols. These are glycerides consisting of three fatty acid chains covalently bonded to a glycerol molecule through ester linkages.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassGlycerolipids
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
Disposition

Biological Location:

  Subcellular:

Source:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

    Cellular process:

    Chemical reaction:

    Biochemical process:

Role

Industrial application:

  Pharmaceutical industry:

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 Solubility6.4e-05 g/LALOGPS
logP7.41ALOGPS
logP8.25ChemAxon
logS-6.9ALOGPS
pKa (Strongest Basic)-6.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area78.9 ŲChemAxon
Rotatable Bond Count26ChemAxon
Refractivity130.87 m³·mol⁻¹ChemAxon
Polarizability57.31 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000900000-2ec19e7d19282502723bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0000900000-2ec19e7d19282502723bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00b9-0009700000-74eec0b6f556539a1960View in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB/PathwhizKEGG
De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/8:0)Pw017051Pw017051 greyscalePw017051 simpleNot Available
Displaying 1 entry
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB003135
KNApSAcK IDNot Available
Chemspider ID10393
KEGG Compound IDC13044
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10850
PDB IDNot Available
ChEBI ID930032
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]
  2. Fendri A, Louati H, Sellami M, Gargouri H, Smichi N, Zarai Z, Aissa I, Miled N, Gargouri Y: A thermoactive uropygial esterase from chicken: purification, characterisation and synthesis of flavour esters. Int J Biol Macromol. 2012 Jun 1;50(5):1238-44. doi: 10.1016/j.ijbiomac.2012.04.008. Epub 2012 Apr 13. [PubMed:22531158 ]
  3. Messaoudi A, Belguith H, Ben Hamida J: Three-Dimensional Structure of Arabidopsis thaliana Lipase Predicted by Homology Modeling Method. Evol Bioinform Online. 2011;7:99-105. doi: 10.4137/EBO.S7122. Epub 2011 Jun 28. [PubMed:21792274 ]
  4. Mateos-Diaz E, Rodriguez JA, de Los Angeles Camacho-Ruiz M, Mateos-Diaz JC: High-throughput screening method for lipases/esterases. Methods Mol Biol. 2012;861:89-100. doi: 10.1007/978-1-61779-600-5_5. [PubMed:22426713 ]
  5. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  6. 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 ]
  7. 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 ]
  8. 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 ]
  9. 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 ]

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
General function:
Lipid transport and metabolism
Specific function:
Converts monoacylglycerides to free fatty acids and glycerol. Hydrolyzes the endocannabinoid 2-arachidonoylglycerol, and thereby contributes to the regulation of endocannabinoid signaling, nociperception and perception of pain (By similarity). Regulates the levels of fatty acids that serve as signaling molecules and promote cancer cell migration, invasion and tumor growth.
Gene Name:
MGLL
Uniprot ID:
Q99685
Molecular weight:
Not Available
General function:
Lipid transport and metabolism
Specific function:
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.
Gene Name:
CES1
Uniprot ID:
P23141
Molecular weight:
62520.62
General function:
Involved in hydrolase activity
Specific function:
In adipose tissue and heart, it primarily hydrolyzes stored triglycerides to free fatty acids, while in steroidogenic tissues, it principally converts cholesteryl esters to free cholesterol for steroid hormone production.
Gene Name:
LIPE
Uniprot ID:
Q05469
Molecular weight:
116596.715
General function:
Involved in isomerase activity
Specific function:
This multifunctional protein catalyzes the formation, breakage and rearrangement of disulfide bonds. At the cell surface, seems to act as a reductase that cleaves disulfide bonds of proteins attached to the cell. May therefore cause structural modifications of exofacial proteins. Inside the cell, seems to form/rearrange disulfide bonds of nascent proteins. At high concentrations, functions as a chaperone that inhibits aggregation of misfolded proteins. At low concentrations, facilitates aggregation (anti-chaperone activity). May be involved with other chaperones in the structural modification of the TG precursor in hormone biogenesis. Also acts a structural subunit of various enzymes such as prolyl 4-hydroxylase and microsomal triacylglycerol transfer protein MTTP
Gene Name:
P4HB
Uniprot ID:
P07237
Molecular weight:
57115.8
General function:
Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:
Catalyzes the formation of diacylglycerol from 2-monoacylglycerol and fatty acyl-CoA. Has a preference toward monoacylglycerols containing unsaturated fatty acids in an order of C18:3 > C18:2 > C18:1 > C18:0. Plays a central role in absorption of dietary fat in the small intestine by catalyzing the resynthesis of triacylglycerol in enterocytes. May play a role in diet-induced obesity.
Gene Name:
MOGAT2
Uniprot ID:
Q3SYC2
Molecular weight:
38195.285
General function:
Involved in metabolic process
Specific function:
Lipid hydrolase.
Gene Name:
PNPLA4
Uniprot ID:
P41247
Molecular weight:
27980.17
General function:
Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:
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).
Gene Name:
DGAT2
Uniprot ID:
Q96PD7
Molecular weight:
39043.88
General function:
Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:
Catalyzes the formation of diacylglycerol from 2-monoacylglycerol and fatty acyl-CoA. Probably not involved in absorption of dietary fat in the small intestine (By similarity).
Gene Name:
MOGAT1
Uniprot ID:
Q96PD6
Molecular weight:
38812.19
General function:
Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:
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.
Gene Name:
MOGAT3
Uniprot ID:
Q86VF5
Molecular weight:
38729.84
General function:
Involved in hydrolase activity
Specific function:
Membrane-associated phospholipase. Exhibits a calcium-independent broad substrate specificity including phospholipase A2/lysophospholipase activity. Preferential hydrolysis at the sn-2 position of diacylphospholipids and diacyglycerol, whereas it shows no positional specificity toward triacylglycerol. Exhibits also esterase activity toward p-nitrophenyl. May act on the brush border membrane to facilitate the absorption of digested lipids (By similarity).
Gene Name:
PLB1
Uniprot ID:
Q6P1J6
Molecular weight:
161711.9
General function:
Involved in acyltransferase activity
Specific function:
Esterifies acyl-group from acyl-ACP to the sn-1 position of glycerol-3-phosphate, an essential step in glycerolipid biosynthesis. Overexpression activates the mTOR pathway.
Gene Name:
AGPAT9
Uniprot ID:
Q53EU6
Molecular weight:
48704.805
General function:
Involved in metabolic process
Specific function:
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.
Gene Name:
PNPLA2
Uniprot ID:
Q96AD5
Molecular weight:
55315.245
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
PNLIPRP3
Uniprot ID:
Q17RR3
Molecular weight:
52253.41
General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
May play a role in triacylglycerol packaging into adipocytes. May function as a coat protein involved in the biogenesis of lipid droplets
Gene Name:
PLIN4
Uniprot ID:
Q96Q06
Molecular weight:
134431.0
General function:
Involved in enzyme activator activity
Specific function:
Component of the very low density lipoprotein (VLDL) fraction in plasma, and is an activator of several triacylglycerol lipases. The association of APOC2 with plasma chylomicrons, VLDL, and HDL is reversible, a function of the secretion and catabolism of triglyceride-rich lipoproteins, and changes rapidly
Gene Name:
APOC2
Uniprot ID:
P02655
Molecular weight:
11283.8

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