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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-14 22:29:32 UTC
Update Date2022-11-30 19:04:37 UTC
HMDB IDHMDB0042989
Secondary Accession Numbers
  • HMDB42989
Metabolite Identification
Common NameTG(15:0/15:0/15:0)
DescriptionTG(15:0/15:0/15:0) is a tripentadecanoic acid triglyceride. Triglycerides (TGs or TAGs) are also known as glycerol tripentadecanoate or triacylglycerols or triacylglycerides, meaning that they are glycerides in which the glycerol is esterified with three fatty acid groups (i.e. fatty acid trimesters 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(15:0/15:0/15:0), in particular, consists of one chain of pentadecanoic acid at the C-1 position, one chain of pentadecanoic acid at the C-2 position and one chain of pentadecanoic 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
Structure
Data?1563863834
Synonyms
ValueSource
1,2,3-Propanetriyl tripentadecanoate, 9ciHMDB
1-Pentadecanoyl-2-pentadecanoyl-3-pentadecanoyl-glycerolHMDB
Glycerol tripentadecanoateHMDB
TAG(15:0/15:0/15:0)HMDB
TAG(45:0)HMDB
TG(45:0)HMDB
Tracylglycerol(15:0/15:0/15:0)HMDB
Tracylglycerol(45:0)HMDB
TriacylglycerolHMDB
TriglycerideHMDB
Tripentadecanoin, 8ciHMDB
TG(15:0/15:0/15:0)Lipid Annotator
Chemical FormulaC48H92O6
Average Molecular Weight765.2405
Monoisotopic Molecular Weight764.689390676
IUPAC Name1,3-bis(pentadecanoyloxy)propan-2-yl pentadecanoate
Traditional Name1,3-bis(pentadecanoyloxy)propan-2-yl pentadecanoate
CAS Registry Number30719-27-8
SMILES
[H]C(COC(=O)CCCCCCCCCCCCCC)(COC(=O)CCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCC
InChI Identifier
InChI=1S/C48H92O6/c1-4-7-10-13-16-19-22-25-28-31-34-37-40-46(49)52-43-45(54-48(51)42-39-36-33-30-27-24-21-18-15-12-9-6-3)44-53-47(50)41-38-35-32-29-26-23-20-17-14-11-8-5-2/h45H,4-44H2,1-3H3
InChI KeyCLJLWABDLPQTHL-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 Point55 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP17.59Extrapolated
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.2e-05 g/LALOGPS
logP10.49ALOGPS
logP17.59ChemAxon
logS-7.8ALOGPS
pKa (Strongest Basic)-6.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area78.9 ŲChemAxon
Rotatable Bond Count47ChemAxon
Refractivity227.49 m³·mol⁻¹ChemAxon
Polarizability103.32 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]+286.53431661259
DarkChem[M-H]-274.64431661259
DeepCCS[M+H]+295.91130932474
DeepCCS[M-H]-293.55330932474
DeepCCS[M-2H]-326.43930932474
DeepCCS[M+Na]+302.00430932474
AllCCS[M+H]+304.932859911
AllCCS[M+H-H2O]+305.032859911
AllCCS[M+NH4]+304.832859911
AllCCS[M+Na]+304.832859911
AllCCS[M-H]-290.032859911
AllCCS[M+Na-2H]-295.132859911
AllCCS[M+HCOO]-300.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
TG(15:0/15:0/15:0)[H]C(COC(=O)CCCCCCCCCCCCCC)(COC(=O)CCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCC5160.6Standard polar33892256
TG(15:0/15:0/15:0)[H]C(COC(=O)CCCCCCCCCCCCCC)(COC(=O)CCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCC4950.5Standard non polar33892256
TG(15:0/15:0/15:0)[H]C(COC(=O)CCCCCCCCCCCCCC)(COC(=O)CCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCC5299.5Semi standard non polar33892256
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - TG(15:0/15:0/15:0) 10V, Positive-QTOFsplash10-001i-0000000900-a4d2ee80ca7c3e155be82017-10-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - TG(15:0/15:0/15:0) 20V, Positive-QTOFsplash10-001i-0000000900-a4d2ee80ca7c3e155be82017-10-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - TG(15:0/15:0/15:0) 40V, Positive-QTOFsplash10-00xr-0000090700-4cb3298a98e089c7d2bc2017-10-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - TG(15:0/15:0/15:0) 10V, Positive-QTOFsplash10-001i-0000000900-ff24e7a6b2a2a0f76d7f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - TG(15:0/15:0/15:0) 20V, Positive-QTOFsplash10-001i-0000000900-ff24e7a6b2a2a0f76d7f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - TG(15:0/15:0/15:0) 40V, Positive-QTOFsplash10-00xr-0010090700-d133131a2b3111baa7bc2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - TG(15:0/15:0/15:0) 10V, Positive-QTOFsplash10-000i-0000000900-a70bfb7c161cdcd59cc22021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - TG(15:0/15:0/15:0) 20V, Positive-QTOFsplash10-000i-0000000900-a70bfb7c161cdcd59cc22021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - TG(15:0/15:0/15:0) 40V, Positive-QTOFsplash10-000i-0000000900-a70bfb7c161cdcd59cc22021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - TG(15:0/15:0/15:0) 10V, Positive-QTOFsplash10-00di-0000000900-d67d8405be9ea658402f2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - TG(15:0/15:0/15:0) 20V, Positive-QTOFsplash10-00di-0000000900-d67d8405be9ea658402f2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - TG(15:0/15:0/15:0) 40V, Positive-QTOFsplash10-00i2-0090090900-07ba1451081a5da98b972021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - TG(15:0/15:0/15:0) 10V, Positive-QTOFsplash10-014i-5020044900-b55b7753908e26369dfb2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - TG(15:0/15:0/15:0) 20V, Positive-QTOFsplash10-05i0-9151026200-9c423367b82b944988752021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - TG(15:0/15:0/15:0) 40V, Positive-QTOFsplash10-0059-3294012000-33f66fdba750a257e26e2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - TG(15:0/15:0/15:0) 10V, Negative-QTOFsplash10-03k9-0060070900-456a89ea9bc145e367072021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - TG(15:0/15:0/15:0) 20V, Negative-QTOFsplash10-01bc-0090020000-e218fcc14e2c31bd4c9a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - TG(15:0/15:0/15:0) 40V, Negative-QTOFsplash10-05mo-0190020000-2fb46252533ef29d81d82021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 +/- 0.000 uMAdult (>18 years old)BothNormal (Most Probable)Calculated using MetaboAnalyst
Blood2.689 +/- 0.532 uMAdult (>18 years old)BothNormal (Upper Limit)Calculated using MetaboAnalyst
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB003116
KNApSAcK IDNot Available
Chemspider ID3496974
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound4290702
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
  7. Linda T. Welson (2006). Triglycerides and Cholesterol Research. Nova Science Publishers Inc..

Only showing the first 10 proteins. There are 39 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
References
  1. Sharp D, Ricci B, Kienzle B, Lin MC, Wetterau JR: Human microsomal triglyceride transfer protein large subunit gene structure. Biochemistry. 1994 Aug 9;33(31):9057-61. [PubMed:7545943 ]
General function:
Involved in lipid binding
Specific function:
Involved in the transfer of insoluble cholesteryl esters in the reverse transport of cholesterol
Gene Name:
CETP
Uniprot ID:
P11597
Molecular weight:
54755.7
References
  1. Swenson TL, Brocia RW, Tall AR: Plasma cholesteryl ester transfer protein has binding sites for neutral lipids and phospholipids. J Biol Chem. 1988 Apr 15;263(11):5150-7. [PubMed:2833496 ]
  2. Sarich TC, Connelly MA, Schranz DB, Ghosh A, Manitpisitkul P, Leary ET, Rothenberg P, Demarest KT, Damiano BP: Phase 0 study of the inhibition of cholesteryl ester transfer protein activity by JNJ-28545595 in plasma from normolipidemic and dyslipidemic humans. Int J Clin Pharmacol Ther. 2012 Aug;50(8):584-94. doi: 10.5414/CP201627. [PubMed:22578199 ]
General function:
Not Available
Specific function:
Inhibits lipoprotein lipase and hepatic lipase and decreases the uptake of lymph chylomicrons by hepatic cells. This suggests that it delays the catabolism of triglyceride-rich particles
Gene Name:
APOC3
Uniprot ID:
P02656
Molecular weight:
10852.0
References
  1. Hidaka H, Takiwaki M, Yamashita M, Kawasaki K, Sugano M, Honda T: Consumption of nonfat milk results in a less atherogenic lipoprotein profile: a pilot study. Ann Nutr Metab. 2012;61(2):111-6. [PubMed:22907079 ]
General function:
Replication, recombination and repair
Specific function:
May have a role in chylomicrons and VLDL secretion and catabolism. Required for efficient activation of lipoprotein lipase by ApoC-II; potent activator of LCAT. Apoa-IV is a major component of HDL and chylomicrons
Gene Name:
APOA4
Uniprot ID:
P06727
Molecular weight:
45400.0
References
  1. Kohan AB, Wang F, Li X, Bradshaw S, Yang Q, Caldwell JL, Bullock TM, Tso P: Apolipoprotein A-IV regulates chylomicron metabolism-mechanism and function. Am J Physiol Gastrointest Liver Physiol. 2012 Mar 15;302(6):G628-36. doi: 10.1152/ajpgi.00225.2011. Epub 2011 Dec 29. [PubMed:22207575 ]
General function:
Not Available
Specific function:
Seems to have numerous potential physiological functions. Binds to collagen, thrombospondin, anionic phospholipids and oxidized LDL. May function as a cell adhesion molecule. Directly mediates cytoadherence of Plasmodium falciparum parasitized erythrocytes. Binds long chain fatty acids and may function in the transport and/or as a regulator of fatty acid transport
Gene Name:
CD36
Uniprot ID:
P16671
Molecular weight:
53054.0
References
  1. Feingold KR, Shigenaga JK, Kazemi MR, McDonald CM, Patzek SM, Cross AS, Moser A, Grunfeld C: Mechanisms of triglyceride accumulation in activated macrophages. J Leukoc Biol. 2012 Oct;92(4):829-39. doi: 10.1189/jlb.1111537. Epub 2012 Jun 29. [PubMed:22753953 ]
General function:
Lipid transport and metabolism
Specific function:
Involved in translocation of long-chain fatty acids (LFCA) across the plasma membrane. The LFCA import appears to be hormone-regulated in a tissue-specific manner. In adipocytes, but not myocytes, insulin induces a rapid translocation of FATP1 from intracellular compartments to the plasma membrane, paralleled by increased LFCA uptake. May act directly as a bona fide transporter, or alternatively, in a cytoplasmic or membrane- associated multimeric protein complex to trap and draw fatty acids towards accumulation. Plays a pivotal role in regulating available LFCA substrates from exogenous sources in tissues undergoing high levels of beta-oxidation or triglyceride synthesis. May be involved in regulation of cholesterol metabolism. Has acyl-CoA ligase activity for long-chain and very-long-chain fatty acids
Gene Name:
SLC27A1
Uniprot ID:
Q6PCB7
Molecular weight:
71107.5
References
  1. Hatch GM, Smith AJ, Xu FY, Hall AM, Bernlohr DA: FATP1 channels exogenous FA into 1,2,3-triacyl-sn-glycerol and down-regulates sphingomyelin and cholesterol metabolism in growing 293 cells. J Lipid Res. 2002 Sep;43(9):1380-9. [PubMed:12235169 ]

Only showing the first 10 proteins. There are 39 proteins in total.