ChemFOnt: Showing chemical card for 6,9,12,15,18,21-Tetracosahexaenoic acid (CFc000008164)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:54:49 UTC

Chemfont ID

CFc000008164

Molecule Identification

Common Name

6,9,12,15,18,21-Tetracosahexaenoic acid

Definition

6,9,12,15,18,21-Tetracosahexaenoic acid (24:6n-3) is one of the n-3 PUFA and is a very long chain fatty acid. Distribution of 24:6n-3 in marine organisms was investigated by several researchers. Takagi et al. reported relatively high contents of 24:6n-3 in sea lilies and brittle stars (4–10% of total fatty acids). High 24:6n-3 content was also found in marine coelenterates. In some edible fishes, 24:6n-3 was detected at significant levels (0–10% of total fatty acids).The existence of 24:6n-3 in mammalian tissues was reported with other very long chain fatty acids in the spermatozoa,the retina, and the brain. Voss et al. reported that 24:6n-3 is formed as an intermediate in the metabolic pathway from 20:5n-3 to 22:6n-3 in rat liver. Even though 24:6n-3 is a PUFA existing in fish and mammalian species, physiological functions of 24:6n-3 have not been studied. As functions to be studied, anti-inflammatory and antiallergic. effects of 24:6n-3 are noteworthy because these events are known to be closely related to the unsaturated fatty acid metabolism such as in the arachidonic acid cascade, and 20:5n-3 and 22:6n-3 were reported to suppress inflammatory actions by influencing arachidonic acid metabolism.s24:6n-3 could inhibit the antigen-stimulated production of LT-related compounds as well as other n-3 polyunsaturated fatty acids (PUFA) such as eicosapentaenoic. acid (20:5n-3) and docosahexaenoic acid (22:6n-3), which are major n-3 PUFA in fish oils; 24:6n-3 was also shown to reduce the histamine content in MC/9 cells at 25 uM (27% reduction from the control), and the effect was diminished with increase of the fatty acid concentration (up to 100 uM). These two n-3 PUFA, 20:5n-3 and 22:6n-3, also reduced the histamine content (16 and 20% reduction at 25 μM, respectively), whereas arachidonic acid (20:4n-6) increased it (18% increase at 25 μM).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
6,9,12,15,18,21-Tetracosahexaenoate	Generator
6Z,9Z,12Z,15Z,18Z,21Z-Tetracosahexaenoate	HMDB
6Z,9Z,12Z,15Z,18Z,21Z-Tetracosahexaenoic acid	HMDB
6Z,9Z,12Z,15Z,18Z,21Z-Tetracosahexaenoic acid anion	HMDB
all-cis-6,9,12,15,18,21-Tetracosahexaenoate	HMDB
all-cis-6,9,12,15,18,21-Tetracosahexaenoic acid	HMDB
C 24:6 (N-3)	HMDB
Nisinate	HMDB
Nisinic acid anion	HMDB
24-6(N-3) acid	MeSH

Chemical Formula

C₂₄H₃₅O₂

Average Molecular Weight

355.5335

Monoisotopic Molecular Weight

355.263705364

IUPAC Name

(6E,9E,12E,15E,18E,21E)-tetracosa-6,9,12,15,18,21-hexaenoate

Traditional Name

(6E,9E,12E,15E,18E,21E)-tetracosa-6,9,12,15,18,21-hexaenoate

CAS Registry Number

81247-23-6

SMILES

CC\C=C\C\C=C\C\C=C\C\C=C\C\C=C\C\C=C\CCCCC([O-])=O

InChI Identifier

InChI=1S/C24H36O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24(25)26/h3-4,6-7,9-10,12-13,15-16,18-19H,2,5,8,11,14,17,20-23H2,1H3,(H,25,26)/p-1/b4-3+,7-6+,10-9+,13-12+,16-15+,19-18+

InChI Key

YHGJECVSSKXFCJ-SFGLVEFQSA-M

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as very long-chain fatty acids. These are fatty acids with an aliphatic tail that contains at least 22 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Very long-chain fatty acids

Alternative Parents

Substituents

Very long-chain fatty acid
Unsaturated fatty acid
Straight chain fatty acid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Organic anion
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0013025)
Membrane (HMDB: HMDB0013025)

Source

Exogenous

Exogenous (HMDB: HMDB0013025)

Food

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Endogenous

Endogenous (HMDB: HMDB0013025)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	7.1e-05 g/L	ALOGPS
logP	7.18	ALOGPS
logP	7.64	ChemAxon
logS	-6.7	ALOGPS
pKa (Strongest Acidic)	4.92	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	40.13 Å²	ChemAxon
Rotatable Bond Count	16	ChemAxon
Refractivity	131.43 m³·mol⁻¹	ChemAxon
Polarizability	43.7 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

FDB029253

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

53481586

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 6,9,12,15,18,21-Tetracosahexaenoic acid (CFc000008164)

MOL for CFc000008164 (6,9,12,15,18,21-Tetracosahexaenoic acid)

3D MOL for CFc000008164 (6,9,12,15,18,21-Tetracosahexaenoic acid)

3D SDF for CFc000008164 (6,9,12,15,18,21-Tetracosahexaenoic acid)

3D-SDF for CFc000008164 (6,9,12,15,18,21-Tetracosahexaenoic acid)

PDB for CFc000008164 (6,9,12,15,18,21-Tetracosahexaenoic acid)

3D PDB for CFc000008164 (6,9,12,15,18,21-Tetracosahexaenoic acid)

SMILES for CFc000008164 (6,9,12,15,18,21-Tetracosahexaenoic acid)

INCHI for CFc000008164 (6,9,12,15,18,21-Tetracosahexaenoic acid)

Structure for CFc000008164 (6,9,12,15,18,21-Tetracosahexaenoic acid)

3D Structure for CFc000008164 (6,9,12,15,18,21-Tetracosahexaenoic acid)