You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
StatusExpected but not Quantified
Creation Date2009-07-25 00:11:52 UTC
Update Date2020-02-26 21:38:04 UTC
Secondary Accession Numbers
  • HMDB13025
Metabolite Identification
Common Name6,9,12,15,18,21-Tetracosahexaenoic acid
Description6,9,12,15,18,21-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).
Chemical FormulaC24H36O2
Average Molecular Weight356.55
Monoisotopic Molecular Weight356.271530399
IUPAC Nametetracosa-6,9,12,15,18,21-hexaenoic acid
Traditional Nametetracosa-6,9,12,15,18,21-hexaenoic acid
CAS Registry NumberNot Available
InChI Identifier
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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentVery long-chain fatty acids
Alternative Parents
  • 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
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available

Route of exposure:


Biological location:


Naturally occurring process:


Industrial application:

Biological role:

Physical Properties
Experimental Properties
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
Water Solubility7.1e-05 g/LALOGPS
pKa (Strongest Acidic)4.92ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count16ChemAxon
Refractivity120.59 m³·mol⁻¹ChemAxon
Polarizability44.15 ųChemAxon
Number of Rings0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0009000000-0aecad3f10eefdf7d1b1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03ds-4559000000-d044187c05f199f03f75Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01p2-9673000000-fe0e36efc6429aef7914Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0009000000-2a2103fe5e22d781b9b9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0bti-0009000000-093b42344e6284ef767dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9123000000-94c48fd43abe43b10fe7Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound54508254
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Nichols PD, Danaher KT, Koslow JA: Occurrence of high levels of tetracosahexaenoic acid in the jellyfish Aurelia sp. Lipids. 2003 Nov;38(11):1207-10. [PubMed:14733367 ]
  2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  3. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  4. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  5. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  6. (). Takagi, T., Kaneniwa, M., and Itabashi, Y. (1986) Fatty Acids in Crinoidea and Ophiuroidea: Occurrence of All-cis-6,9,12,15, 18,21-Tetracosahexaenoic Acid, Lipids 21, 430–433.. .
  7. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.