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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:41:01 UTC
Update Date2022-03-07 02:52:49 UTC
HMDB IDHMDB0031110
Secondary Accession Numbers
  • HMDB31110
Metabolite Identification
Common NameGlycerol tritridecanoate
DescriptionGlycerol tritridecanoate is a probable constituent of fats. TG(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?1563862082
Synonyms
ValueSource
Glycerol tritridecanoic acidGenerator
1,2,3-Propanetriyl tritridecanoate, 9ciHMDB
Tritridecanoin, 8ciHMDB
Chemical FormulaC42H80O6
Average Molecular Weight681.081
Monoisotopic Molecular Weight680.595490292
IUPAC Name1,3-bis(tridecanoyloxy)propan-2-yl tridecanoate
Traditional Name1,3-bis(tridecanoyloxy)propan-2-yl tridecanoate
CAS Registry Number26536-12-9
SMILES
CCCCCCCCCCCCC(=O)OCC(COC(=O)CCCCCCCCCCCC)OC(=O)CCCCCCCCCCCC
InChI Identifier
InChI=1S/C42H80O6/c1-4-7-10-13-16-19-22-25-28-31-34-40(43)46-37-39(48-42(45)36-33-30-27-24-21-18-15-12-9-6-3)38-47-41(44)35-32-29-26-23-20-17-14-11-8-5-2/h39H,4-38H2,1-3H3
InChI KeyUDXANBFMQUOKTQ-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
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point44.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility3.3e-13 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.3e-05 g/LALOGPS
logP10.07ALOGPS
logP14.92ChemAxon
logS-7.7ALOGPS
pKa (Strongest Basic)-6.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area78.9 ŲChemAxon
Rotatable Bond Count41ChemAxon
Refractivity199.88 m³·mol⁻¹ChemAxon
Polarizability91.07 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+263.87231661259
DarkChem[M-H]-255.4631661259
DeepCCS[M+H]+276.75430932474
DeepCCS[M-H]-274.39630932474
DeepCCS[M-2H]-308.59130932474
DeepCCS[M+Na]+284.17730932474
AllCCS[M+H]+287.232859911
AllCCS[M+H-H2O]+287.032859911
AllCCS[M+NH4]+287.332859911
AllCCS[M+Na]+287.332859911
AllCCS[M-H]-264.732859911
AllCCS[M+Na-2H]-269.332859911
AllCCS[M+HCOO]-274.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Glycerol tritridecanoateCCCCCCCCCCCCC(=O)OCC(COC(=O)CCCCCCCCCCCC)OC(=O)CCCCCCCCCCCC4968.0Standard polar33892256
Glycerol tritridecanoateCCCCCCCCCCCCC(=O)OCC(COC(=O)CCCCCCCCCCCC)OC(=O)CCCCCCCCCCCC4210.1Standard non polar33892256
Glycerol tritridecanoateCCCCCCCCCCCCC(=O)OCC(COC(=O)CCCCCCCCCCCC)OC(=O)CCCCCCCCCCCC4689.6Semi standard non polar33892256
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycerol tritridecanoate 10V, Positive-QTOFsplash10-0002-0000009000-a44bb5f42de5a1ae200e2017-10-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycerol tritridecanoate 20V, Positive-QTOFsplash10-0002-0000009000-a44bb5f42de5a1ae200e2017-10-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycerol tritridecanoate 40V, Positive-QTOFsplash10-0159-0000907000-7583eb1a166c9e9b4b462017-10-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycerol tritridecanoate 10V, Positive-QTOFsplash10-0udi-0000000900-695da9e0d66dd1f66a592021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycerol tritridecanoate 20V, Positive-QTOFsplash10-0udi-0000000900-695da9e0d66dd1f66a592021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycerol tritridecanoate 40V, Positive-QTOFsplash10-0udi-0000000900-695da9e0d66dd1f66a592021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycerol tritridecanoate 10V, Positive-QTOFsplash10-001i-0100109000-5a76b64ac03f82d9efb12021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycerol tritridecanoate 20V, Positive-QTOFsplash10-06rt-2910328000-9b565062a7546e84dc082021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycerol tritridecanoate 40V, Positive-QTOFsplash10-0535-9320000000-280e7f7f318dff9d938c2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycerol tritridecanoate 10V, Positive-QTOFsplash10-000i-0000009000-63ad216e53297c6978a62021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycerol tritridecanoate 20V, Positive-QTOFsplash10-000i-0000009000-63ad216e53297c6978a62021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycerol tritridecanoate 40V, Positive-QTOFsplash10-00dr-0090909000-c0d611659287ec92097e2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycerol tritridecanoate 10V, Positive-QTOFsplash10-0002-0000009000-9396795dbc2df771836f2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycerol tritridecanoate 20V, Positive-QTOFsplash10-0002-0000009000-9396795dbc2df771836f2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycerol tritridecanoate 40V, Positive-QTOFsplash10-0159-0100907000-607bc789ee1208a482b22021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycerol tritridecanoate 10V, Negative-QTOFsplash10-004i-0060709000-85b8caf668e0968a7a7c2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycerol tritridecanoate 20V, Negative-QTOFsplash10-03di-0090202000-2f02257a20a93e6f2a2c2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycerol tritridecanoate 40V, Negative-QTOFsplash10-03di-0090110000-837af8d9ba6f782d14c82021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
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
FooDB IDFDB003117
KNApSAcK IDNot Available
Chemspider ID105278
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound117811
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1824771
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  7. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
  8. Linda T. Welson (2006). Triglycerides and Cholesterol Research. Nova Science Publishers Inc..