Human Metabolome Database Version 3.5

Showing metabocard for TG(15:0/16:0/20:2(11Z,14Z))[iso6] (HMDB11700)

Record Information
Version 3.5
Creation Date 2009-02-19 16:38:59 -0700
Update Date 2013-02-08 17:27:11 -0700
HMDB ID HMDB11700
Secondary Accession Numbers None
Metabolite Identification
Common Name TG(15:0/16:0/20:2(11Z,14Z))[iso6]
Description TG(15:0/16:0/20:2(11Z,14Z)) is a monoeicosadienoic acid 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 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(15:0/16:0/20:2(11Z,14Z)), in particular, consists of one chain of pentadecanoic acid at the C-1 position, one chain of palmitic acid at the C-2 position and one chain of eicosadienoic 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
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 1-Pentadecanoyl-2-palmitoyl-3-eicosadienoyl-glycerol
  2. TAG(15:0/16:0/20:2)
  3. TAG(15:0/16:0/20:2n6)
  4. TAG(15:0/16:0/20:2w6)
  5. TAG(51:2)
  6. TG(15:0/16:0/20:2)
  7. TG(15:0/16:0/20:2n6)
  8. TG(15:0/16:0/20:2w6)
  9. TG(51:2)
  10. Tracylglycerol(15:0/16:0/20:2)
  11. Tracylglycerol(15:0/16:0/20:2n6)
  12. Tracylglycerol(15:0/16:0/20:2w6)
  13. Tracylglycerol(51:2)
  14. Triacylglycerol
  15. Triglyceride
Chemical Formula C54H100O6
Average Molecular Weight 845.3682
Monoisotopic Molecular Weight 844.751990932
IUPAC Name (2R)-2-(hexadecanoyloxy)-3-(pentadecanoyloxy)propyl (11Z,14Z)-icosa-11,14-dienoate
Traditional IUPAC Name (2R)-2-(hexadecanoyloxy)-3-(pentadecanoyloxy)propyl (11Z,14Z)-icosa-11,14-dienoate
CAS Registry Number Not Available
SMILES [H][C@@](COC(=O)CCCCCCCCCCCCCC)(COC(=O)CCCCCCCCC\C=C/C\C=C/CCCCC)OC(=O)CCCCCCCCCCCCCCC
InChI Identifier InChI=1S/C54H100O6/c1-4-7-10-13-16-19-22-25-26-27-28-30-32-35-38-41-44-47-53(56)59-50-51(49-58-52(55)46-43-40-37-34-31-24-21-18-15-12-9-6-3)60-54(57)48-45-42-39-36-33-29-23-20-17-14-11-8-5-2/h16,19,25-26,51H,4-15,17-18,20-24,27-50H2,1-3H3/b19-16-,26-25-/t51-/m1/s1
InChI Key VVCOWDFFHRITHU-AMOPXLHCSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Glycerolipids
Sub Class Triacylglycerols
Other Descriptors
  • Aliphatic Acyclic Compounds
Substituents
  • Acyclic Alkene
  • Carboxylic Acid Ester
  • Fatty Acid Ester
  • Tricarboxylic Acid Derivative
Direct Parent Triacylglycerols
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Energy source
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane component
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
LogP 10.74 ALOGPS
LogP 19.53 ChemAxon
LogS -8.06 ALOGPS
pKa (strongest basic) -6.6 ChemAxon
Hydrogen Acceptor Count 3 ChemAxon
Hydrogen Donor Count 0 ChemAxon
Polar Surface Area 78.9 A2 ChemAxon
Rotatable Bond Count 51 ChemAxon
Refractivity 257.33 ChemAxon
Polarizability 112.85 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations Not Available
Tissue Location
  • All Tissues
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Predicted Concentrations Help
Biofluid Value Original age Original sex Original condition Comments
Blood 0.003178167 +/- 0.001594253 uM Adult (>18 years old) Both Normal (Most Probable) Calculated using MetaboAnalyst
Blood 5.433333333 +/- 2.00333056 uM Adult (>18 years old) Both Normal (Upper Limit) Calculated using MetaboAnalyst
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB028386
KNApSAcK ID Not Available
Chemspider ID 24768314 Link_out
KEGG Compound ID Not Available
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB11700 Link_out
Metagene Link HMDB11700 Link_out
METLIN ID Not Available
PubChem Compound 53481032 Link_out
PDB ID Not Available
ChEBI ID Not Available
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References
  1. Ding J, Sorensen CM, Jaitly N, Jiang H, Orton DJ, Monroe ME, Moore RJ, Smith RD, Metz TO: Application of the accurate mass and time tag approach in studies of the human blood lipidome. J Chromatogr B Analyt Technol Biomed Life Sci. 2008 Aug 15;871(2):243-52. Epub 2008 May 7. Pubmed: 18502191 Link_out

Enzymes
Name: Pancreatic triacylglycerol lipase
Reactions: Not Available
Gene Name: PNLIP
Uniprot ID: P16233 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Hepatic triacylglycerol lipase
Reactions: Not Available
Gene Name: LIPC
Uniprot ID: P11150 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Inactive pancreatic lipase-related protein 1
Reactions: Not Available
Gene Name: PNLIPRP1
Uniprot ID: P54315 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Patatin-like phospholipase domain-containing protein 3
Reactions: Not Available
Gene Name: PNPLA3
Uniprot ID: Q9NST1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Gastric triacylglycerol lipase
Reactions: Not Available
Gene Name: LIPF
Uniprot ID: P07098 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Endothelial lipase
Reactions: Not Available
Gene Name: LIPG
Uniprot ID: Q9Y5X9 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Bile salt-activated lipase
Reactions: Not Available
Gene Name: CEL
Uniprot ID: P19835 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Diacylglycerol O-acyltransferase 1
Reactions: Not Available
Gene Name: DGAT1
Uniprot ID: O75907 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Pancreatic lipase-related protein 2
Reactions: Not Available
Gene Name: PNLIPRP2
Uniprot ID: P54317 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Lipoprotein lipase
Reactions: Not Available
Gene Name: LPL
Uniprot ID: P06858 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Monoglyceride lipase
Reactions: Not Available
Gene Name: MGLL
Uniprot ID: Q99685 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Liver carboxylesterase 1
Reactions: Not Available
Gene Name: CES1
Uniprot ID: P23141 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Hormone-sensitive lipase
Reactions: Not Available
Gene Name: LIPE
Uniprot ID: Q05469 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Protein disulfide-isomerase
Reactions: Not Available
Gene Name: P4HB
Uniprot ID: P07237 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 2-acylglycerol O-acyltransferase 2
Reactions: Not Available
Gene Name: MOGAT2
Uniprot ID: Q3SYC2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Patatin-like phospholipase domain-containing protein 4
Reactions: Not Available
Gene Name: PNPLA4
Uniprot ID: P41247 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Diacylglycerol O-acyltransferase 2
Reactions: Not Available
Gene Name: DGAT2
Uniprot ID: Q96PD7 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 2-acylglycerol O-acyltransferase 1
Reactions: Not Available
Gene Name: MOGAT1
Uniprot ID: Q96PD6 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 2-acylglycerol O-acyltransferase 3
Reactions: Not Available
Gene Name: MOGAT3
Uniprot ID: Q86VF5 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phospholipase B1, membrane-associated
Reactions: Not Available
Gene Name: PLB1
Uniprot ID: Q6P1J6 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Glycerol-3-phosphate acyltransferase 3
Reactions: Not Available
Gene Name: AGPAT9
Uniprot ID: Q53EU6 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Patatin-like phospholipase domain-containing protein 2
Reactions: Not Available
Gene Name: PNPLA2
Uniprot ID: Q96AD5 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Pancreatic lipase-related protein 3
Reactions: Not Available
Gene Name: PNLIPRP3
Uniprot ID: Q17RR3 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Perilipin-4
Reactions: Not Available
Gene Name: PLIN4
Uniprot ID: Q96Q06 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Apolipoprotein C-II
Reactions: Not Available
Gene Name: APOC2
Uniprot ID: P02655 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Transporters
Name: Microsomal triglyceride transfer protein large subunit
Reactions: Not Available
Gene Name: MTTP
Uniprot ID: P55157 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA