ChemFOnt: Showing chemical card for TG(18:0/18:0/20:4(5Z,8Z,11Z,14Z))[iso3] (CFc000337019)

Record Information

Version

1.0

Creation Date

Update Date

2022-09-14 05:30:30 UTC

Chemfont ID

CFc000337019

Molecule Identification

Common Name

TG(18:0/18:0/20:4(5Z,8Z,11Z,14Z))[iso3]

Definition

TG(18:0/18:0/20:4(5Z,8Z,11Z,14Z))[iso3] is a distearic 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 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(18:0/18:0/20:4(5Z,8Z,11Z,14Z))[iso3], in particular, consists of one chain of stearic acid at the C-1 position, one chain of stearic acid at the C-2 position and one chain of arachidonic 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. [HMDB]

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₅₉H₁₀₆O₆

Average Molecular Weight

911.4693

Monoisotopic Molecular Weight

910.798941124

IUPAC Name

(2R)-2,3-bis(octadecanoyloxy)propyl icosa-5,8,11,14-tetraenoate

Traditional Name

(2R)-2,3-bis(octadecanoyloxy)propyl icosa-5,8,11,14-tetraenoate

CAS Registry Number

Not Available

SMILES

[H][C@@](COC(=O)CCCCCCCCCCCCCCCCC)(COC(=O)CCCC=CCC=CCC=CCC=CCCCCC)OC(=O)CCCCCCCCCCCCCCCCC

InChI Identifier

InChI=1S/C59H106O6/c1-4-7-10-13-16-19-22-25-28-29-32-34-37-40-43-46-49-52-58(61)64-55-56(65-59(62)53-50-47-44-41-38-35-31-27-24-21-18-15-12-9-6-3)54-63-57(60)51-48-45-42-39-36-33-30-26-23-20-17-14-11-8-5-2/h16,19,25,28,32,34,40,43,56H,4-15,17-18,20-24,26-27,29-31,33,35-39,41-42,44-55H2,1-3H3/t56-/m1/s1

InChI Key

CIRJQIDEADRSMG-LXXIDKMWSA-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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerolipids

Sub Class

Triradylcglycerols

Direct Parent

Triacylglycerols

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 Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Exogenous (HMDB: HMDB05398)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	6.0e-06 g/L	ALOGPS
logP	10.9	ALOGPS
logP	21.03	ChemAxon
logS	-8.2	ALOGPS
pKa (Strongest Basic)	-6.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	78.9 Å²	ChemAxon
Rotatable Bond Count	54	ChemAxon
Refractivity	282.56 m³·mol⁻¹	ChemAxon
Polarizability	120.32 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023676

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for TG(18:0/18:0/20:4(5Z,8Z,11Z,14Z))[iso3] (CFc000337019)

MOL for CFc000337019 (TG(18:0/18:0/20:4(5Z,8Z,11Z,14Z))[iso3])

3D MOL for CFc000337019 (TG(18:0/18:0/20:4(5Z,8Z,11Z,14Z))[iso3])

3D SDF for CFc000337019 (TG(18:0/18:0/20:4(5Z,8Z,11Z,14Z))[iso3])

3D-SDF for CFc000337019 (TG(18:0/18:0/20:4(5Z,8Z,11Z,14Z))[iso3])

PDB for CFc000337019 (TG(18:0/18:0/20:4(5Z,8Z,11Z,14Z))[iso3])

3D PDB for CFc000337019 (TG(18:0/18:0/20:4(5Z,8Z,11Z,14Z))[iso3])

SMILES for CFc000337019 (TG(18:0/18:0/20:4(5Z,8Z,11Z,14Z))[iso3])

INCHI for CFc000337019 (TG(18:0/18:0/20:4(5Z,8Z,11Z,14Z))[iso3])

Structure for CFc000337019 (TG(18:0/18:0/20:4(5Z,8Z,11Z,14Z))[iso3])

3D Structure for CFc000337019 (TG(18:0/18:0/20:4(5Z,8Z,11Z,14Z))[iso3])