Tetracosahexaenoic acid

PUFA24:6Ω-3

  Overview

Stats

PUFA
Type
24
Carbons
6
Double bonds
5
Bis-allylic sites
356.5
Weight · g/mol
—
Melting point
C24H36O2
Formula

Also known as

IUPAC (6Z,9Z,12Z,15Z,18Z,21Z)-tetracosa-6,9,12,15,18,21-hexaenoic acid
Traditional Nisinic acid

  At a Glance

Key Points

Also called nisinic acid; a very-long-chain omega-3 involved in the body's final step of making DHA.

Source

Found in fish & seafood. Also made by the body.

Type

Very-long-chain polyunsaturated fatty acid with 24 carbons and six cis double bonds, an omega-3 fatty acid. Its multiple bis-allylic sites make it prone to oxidation.

Identification

  Synonyms

Common Name Tetracosahexaenoic acid
IUPAC Name (6Z,9Z,12Z,15Z,18Z,21Z)-tetracosa-6,9,12,15,18,21-hexaenoic acid
Traditional Name Nisinic acid
Other Synonyms No other synonyms recorded.

  External IDs

General References
Wikipedia Nisinic_acid
Lipids
Lipid Maps LMFA01030822
Lipid Bank —
Swiss Lipids 000001212
PlantFA ID —
Food & Nutrition
FooDB FDB022791
INFOODS —
Chemistry / Compounds
PubChem CID 11792612
CAS 68378-49-4
ChEBI 77366
ChEMBL —
ChemSpider 9967286
InChIKey —
ZINC ID ZINC000036440830
NIKKAJI ID —
PDBe —
UCI (UniChem) —
SureChEMBL 454567
CCDC —
NMRShiftDB —
Metabolites & Pathways
HMDB HMDB0002007
METLIN —
RefMet ID —
RefMet Name —
MetaboLights ID MTBLS6578
BioCyc/MetaCyc —
MetaNetX ID MNXM83807
BiGG ID —
KEGG —
KNApSAcK —
Reactome ID —
Drugs & Pharmacology
DrugBank —
DrugCentral —
BindingDB —
Guide to Pharm —
Probes & Drugs —
Clinical & Medical
SNOMED-CT —
MeSH —
NCIt Code —
Regulatory
NIH UNII (USA) L8L6GYZ1ZX
FDA SRS (USA) L8L6GYZ1ZX
NHPID (Canada) —
DTXSID (USA) DTXSID801318739
TGA Ing ID (Australia) —
Commercial Suppliers
MolPort —
eMolecules —
Mcule —
ChemicalBook —
MedChemExpress —

Isomers of 24:6 (1)

Other fatty acids sharing the 24:6 notation — differing by double-bond position, geometry (cis/trans), or conjugation.

Name Geometry Trans Structure PubChem
Current Fatty Acid
Tetracosahexaenoic acid
(6Z,9Z,12Z,15Z,18Z,21Z)-tetracosa-6,9,12,15,18,21-hexaenoic acid
 6Z,9Z,12Z,15Z,18Z,21Z —
11792612
Category —
Conjugation Type Isolated
SMILES CC\C=C/C\C=C/C/C=C\C/C=C\C/C=C\C/C=C\CCCCC(=O)O
Description —
Origin Details

No origin information recorded.

Chemical Properties

Name(s):
Common Name Tetracosahexaenoic acid
Simple Notation 24:6
Notation 24:6(n-3)
IUPAC Name (6Z,9Z,12Z,15Z,18Z,21Z)-tetracosa-6,9,12,15,18,21-hexaenoic acid
Traditional Name Nisinic acid
Semi-systematic Tetracosahexaenoic acid
Structure:
Molecular C24H36O2
SMILES CC\C=C/C\C=C/C/C=C\C/C=C\C/C=C\C/C=C\CCCCC(=O)O
Cis / Trans cis
E-Z 6Z,9Z,12Z,15Z,18Z,21Z
Physical:
Weight 356.5 g/mol
Reactivity
Double Bonds 6
Bis-Allylic Carbons 5 (High Reactivity)
Beta-Oxidation
Beta Oxidation Cycles 11
ATP Yield (Net) 153 ATP