Record Information
Version3.6
Creation Date2009-02-19 23:39:09 UTC
Update Date2013-02-09 00:27:12 UTC
HMDB IDHMDB11709
Secondary Accession NumbersNone
Metabolite Identification
Common NameTG(15:0/18:1(9Z)/18:3(9Z,12Z,15Z))[iso6]
DescriptionTG(15:0/18:1(9Z)/18:3(9Z,12Z,15Z)) is a monooleic 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(15:0/18:1(9Z)/18:3(9Z,12Z,15Z)), in particular, consists of one chain of pentadecanoic acid at the C-1 position, one chain of oleic acid at the C-2 position and one chain of a-linolenic 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
  1. 1-Pentadecanoyl-2-oleoyl-3-a-linolenoyl-glycerol
  2. 1-Pentadecanoyl-2-oleoyl-3-alpha-linolenoyl-glycerol
  3. TAG(15:0/18:1/18:3)
  4. TAG(15:0/18:1n9/18:3n3)
  5. TAG(15:0/18:1w9/18:3w3)
  6. TAG(51:4)
  7. TG(15:0/18:1/18:3)
  8. TG(15:0/18:1n9/18:3n3)
  9. TG(15:0/18:1w9/18:3w3)
  10. TG(51:4)
  11. Tracylglycerol(15:0/18:1/18:3)
  12. Tracylglycerol(15:0/18:1n9/18:3n3)
  13. Tracylglycerol(15:0/18:1w9/18:3w3)
  14. Tracylglycerol(51:4)
  15. Triacylglycerol
  16. Triglyceride
Chemical FormulaC54H96O6
Average Molecular Weight841.3364
Monoisotopic Molecular Weight840.720690804
IUPAC Name(2R)-2-[(9Z)-octadec-9-enoyloxy]-3-(pentadecanoyloxy)propyl (9Z,12Z,15Z)-octadeca-9,12,15-trienoate
Traditional IUPAC Name(2R)-2-[(9Z)-octadec-9-enoyloxy]-3-(pentadecanoyloxy)propyl (9Z,12Z,15Z)-octadeca-9,12,15-trienoate
CAS Registry NumberNot Available
SMILES
[H][C@@](COC(=O)CCCCCCCCCCCCCC)(COC(=O)CCCCCCC\C=C/C\C=C/C\C=C/CC)OC(=O)CCCCCCC\C=C/CCCCCCCC
InChI Identifier
InChI=1S/C54H96O6/c1-4-7-10-13-16-19-22-25-27-29-32-35-38-41-44-47-53(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)48-45-42-39-36-33-30-28-26-23-20-17-14-11-8-5-2/h7,10,16,19,25-28,51H,4-6,8-9,11-15,17-18,20-24,29-50H2,1-3H3/b10-7-,19-16-,27-25-,28-26-/t51-/m1/s1
InChI KeyAKXOSLAHFAWDCG-KQCPJNLHSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassLipids
ClassGlycerolipids
Sub ClassTriacylglycerols
Other Descriptors
  • Aliphatic Acyclic Compounds
Substituents
  • Acyclic Alkene
  • Carboxylic Acid Ester
  • Fatty Acid Ester
  • Octadecanoid
  • Tricarboxylic Acid Derivative
Direct ParentTriacylglycerols
Ontology
StatusExpected 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
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
water solubility6.940E-06 g/LALOGPS
logP10.74ALOGPS
logP18.81ChemAxon
logS-8.1ALOGPS
pKa (strongest basic)-6.6ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count3ChemAxon
hydrogen donor count0ChemAxon
polar surface area78.9ChemAxon
rotatable bond count49ChemAxon
refractivity259.56ChemAxon
polarizability109.55ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue Location
  • All Tissues
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Predicted Concentrations Help
BiofluidValueOriginal ageOriginal sexOriginal conditionComments
Blood0.014713143 +/- 0.003589562 uMAdult (>18 years old)BothNormal (Most Probable)Calculated using MetaboAnalyst
Blood8.066666667 +/- 1.594783162 uMAdult (>18 years old)BothNormal (Upper Limit)Calculated using MetaboAnalyst
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 IDFDB028395
KNApSAcK IDNot Available
Chemspider ID24768323
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB11709
Metagene LinkHMDB11709
METLIN IDNot Available
PubChem Compound53481041
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot 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

Enzymes

Gene Name:
PNLIP
Uniprot ID:
P16233
Gene Name:
LIPC
Uniprot ID:
P11150
Gene Name:
LIPF
Uniprot ID:
P07098
Gene Name:
LIPG
Uniprot ID:
Q9Y5X9
Gene Name:
CEL
Uniprot ID:
P19835
Gene Name:
DGAT1
Uniprot ID:
O75907
Gene Name:
PNLIPRP2
Uniprot ID:
P54317
Gene Name:
LPL
Uniprot ID:
P06858
Gene Name:
MGLL
Uniprot ID:
Q99685
Gene Name:
CES1
Uniprot ID:
P23141
Gene Name:
LIPE
Uniprot ID:
Q05469
Gene Name:
P4HB
Uniprot ID:
P07237
Gene Name:
MOGAT2
Uniprot ID:
Q3SYC2
Gene Name:
DGAT2
Uniprot ID:
Q96PD7
Gene Name:
MOGAT1
Uniprot ID:
Q96PD6
Gene Name:
MOGAT3
Uniprot ID:
Q86VF5
Gene Name:
AGPAT9
Uniprot ID:
Q53EU6
Gene Name:
PNLIPRP3
Uniprot ID:
Q17RR3
Gene Name:
PLIN4
Uniprot ID:
Q96Q06
Gene Name:
APOC2
Uniprot ID:
P02655

Transporters