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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2008-11-04 14:21:19 UTC
Update Date2017-12-20 21:22:58 UTC
HMDB IDHMDB0011188
Secondary Accession Numbers
  • HMDB11188
Metabolite Identification
Common NameTG(12:0/12:0/12:0)
DescriptionTG(12:0/12:0/12:0) or trilauric glyceride is a tridodecanoic 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(12:0/12:0/12:0), in particular, consists of one chain of dodecanoic acid at the C-1 position, one chain of dodecanoic acid at the C-2 position and one chain of dodecanoic 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
Thumb
Synonyms
ValueSource
1,2,3-TridodecanoylglycerolChEBI
1,2,3-TrilauroylglycerolChEBI
Dodecanoic acid 1,2,3-propanetriyl esterChEBI
Glycerin trilaurateChEBI
Glycerol trilaurateChEBI
Glyceryl tridodecanoateChEBI
Glyceryl trilaurateChEBI
Lauric acid triglycerideChEBI
Lauric acid triglycerin esterChEBI
Propane-1,2,3-triyl trilaurateChEBI
TG 12:0/12:0/12:0ChEBI
TG(12:0/12:0/12:0)ChEBI
TridodecanoinChEBI
Tridodecanoyl glycerolChEBI
TridodecanoylglycerolChEBI
TrilauroylglycerolChEBI
Dodecanoate 1,2,3-propanetriyl esterGenerator
Glycerin trilauric acidGenerator
Glycerol trilauric acidGenerator
Glyceryl tridodecanoic acidGenerator
Glyceryl trilauric acidGenerator
Laate triglycerideGenerator
Laic acid triglycerideGenerator
Laate triglycerin esterGenerator
Laic acid triglycerin esterGenerator
Propane-1,2,3-triyl trilauric acidGenerator
Glycerin trilaateGenerator
Glycerin trilaic acidGenerator
Glycerol trilaateGenerator
Glycerol trilaic acidGenerator
Glyceryl trilaateGenerator
Glyceryl trilaic acidGenerator
Propane-1,2,3-triyl trilaateGenerator
Propane-1,2,3-triyl trilaic acidGenerator
1-dodecanoyl-2-dodecanoyl-3-dodecanoyl-glycerol; TriacylglycerolLipid Annotator
Tracylglycerol(12:0/12:0/12:0)Lipid Annotator
Tracylglycerol(36:0)Lipid Annotator
1-dodecanoyl-2-dodecanoyl-3-dodecanoyl-glycerolLipid Annotator
TriglycerideLipid Annotator
TG(36:0)Lipid Annotator
TAG(36:0)Lipid Annotator
TAG(12:0/12:0/12:0)Lipid Annotator
TriacylglycerolLipid Annotator
Chemical FormulaC39H74O6
Average Molecular Weight639.0013
Monoisotopic Molecular Weight638.5485401
IUPAC Name1,3-bis(dodecanoyloxy)propan-2-yl dodecanoate
Traditional Name1,3-bis(dodecanoyloxy)propan-2-yl dodecanoate
CAS Registry NumberNot Available
SMILES
[H]C(COC(=O)CCCCCCCCCCC)(COC(=O)CCCCCCCCCCC)OC(=O)CCCCCCCCCCC
InChI Identifier
InChI=1S/C39H74O6/c1-4-7-10-13-16-19-22-25-28-31-37(40)43-34-36(45-39(42)33-30-27-24-21-18-15-12-9-6-3)35-44-38(41)32-29-26-23-20-17-14-11-8-5-2/h36H,4-35H2,1-3H3
InChI KeyVMPHSYLJUKZBJJ-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
Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

    Cellular process:

    Chemical reaction:

    Biochemical process:

    Multicellular process:

Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Tissue and substructures:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Role

Industrial application:

Biological role:

Physiological effect

Health effect:

  Health condition:

    Metabolism and nutrition disorders:

    Cancer:

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 Solubility1.3e-05 g/LALOGPS
logP9.73ALOGPS
logP13.59ChemAxon
logS-7.7ALOGPS
pKa (Strongest Basic)-6.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area78.9 ŲChemAxon
Rotatable Bond Count38ChemAxon
Refractivity186.08 m³·mol⁻¹ChemAxon
Polarizability82.63 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-001l-3751900000-186ab5f4aeb9dcd0e97bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0000009000-f0a58fa5fad480d99bafView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0000009000-f0a58fa5fad480d99bafView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0000907000-ab658a63ebc1bf1cb2e9View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB/PathwhizKEGG
De Novo Triacylglycerol Biosynthesis TG(12:0/12:0/12:0)Pw017052Pw017052 greyscalePw017052 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 IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10851
PDB IDNot Available
ChEBI ID77389
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Potta SG, Minemi S, Nukala RK, Peinado C, Lamprou DA, Urquhart A, Douroumis D: Development of solid lipid nanoparticles for enhanced solubility of poorly soluble drugs. J Biomed Nanotechnol. 2010 Dec;6(6):634-40. [PubMed:21361127 ]
  2. Kanda A, Namiki F, Hara S: Enzymatic preparation of structured oils containing short-chain fatty acids. J Oleo Sci. 2010;59(12):641-5. [PubMed:21099141 ]
  3. Gupta S, Dube A, Vyas SP: Antileishmanial efficacy of amphotericin B bearing emulsomes against experimental visceral leishmaniasis. J Drug Target. 2007 Jul;15(6):437-44. [PubMed:17613662 ]
  4. Pynn CJ, Picardi MV, Nicholson T, Wistuba D, Poets CF, Schleicher E, Perez-Gil J, Bernhard W: Myristate is selectively incorporated into surfactant and decreases dipalmitoylphosphatidylcholine without functional impairment. Am J Physiol Regul Integr Comp Physiol. 2010 Nov;299(5):R1306-16. doi: 10.1152/ajpregu.00380.2010. Epub 2010 Sep 1. [PubMed:20811010 ]
  5. Legrand P, Beauchamp E, Catheline D, Pedrono F, Rioux V: Short chain saturated fatty acids decrease circulating cholesterol and increase tissue PUFA content in the rat. Lipids. 2010 Nov;45(11):975-86. doi: 10.1007/s11745-010-3481-5. Epub 2010 Oct 6. [PubMed:20924709 ]
  6. Karabulut I, Durmaz G, Hayaloglu AA: Fatty acid selectivity of lipases during acidolysis reaction between oleic acid and monoacid triacylglycerols. J Agric Food Chem. 2009 Nov 11;57(21):10466-70. doi: 10.1021/jf902816e. [PubMed:19835376 ]
  7. Angkawidjaja C, Matsumura H, Koga Y, Takano K, Kanaya S: X-ray crystallographic and MD simulation studies on the mechanism of interfacial activation of a family I.3 lipase with two lids. J Mol Biol. 2010 Jul 2;400(1):82-95. doi: 10.1016/j.jmb.2010.04.051. Epub 2010 May 11. [PubMed:20438738 ]
  8. Liao CY, Su YC: Formation of biodegradable microcapsules utilizing 3D, selectively surface-modified PDMS microfluidic devices. Biomed Microdevices. 2010 Feb;12(1):125-33. doi: 10.1007/s10544-009-9367-8. [PubMed:19851872 ]
  9. Supakdamrongkul P, Bhumiratana A, Wiwat C: Characterization of an extracellular lipase from the biocontrol fungus, Nomuraea rileyi MJ, and its toxicity toward Spodoptera litura. J Invertebr Pathol. 2010 Nov;105(3):228-35. doi: 10.1016/j.jip.2010.06.011. Epub 2010 Jul 1. [PubMed:20600093 ]
  10. Pink DA, Hanna CB, Sandt C, MacDonald AJ, MacEachern R, Corkery R, Rousseau D: Modeling the solid-liquid phase transition in saturated triglycerides. J Chem Phys. 2010 Feb 7;132(5):054502. doi: 10.1063/1.3276108. [PubMed:20136317 ]
  11. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  12. 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 ]
  13. 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 ]
  14. 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 ]
  15. 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 ]
  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..

Only showing the first 10 proteins. There are 30 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 lipid metabolic process
Specific function:
Crucial for the intracellular hydrolysis of cholesteryl esters and triglycerides that have been internalized via receptor-mediated endocytosis of lipoprotein particles. Important in mediating the effect of LDL (low density lipoprotein) uptake on suppression of hydroxymethylglutaryl-CoA reductase and activation of endogenous cellular cholesteryl ester formation.
Gene Name:
LIPA
Uniprot ID:
P38571
Molecular weight:
45418.71
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

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 30 proteins in total.