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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2006-05-22 14:17:31 UTC
Update Date2020-02-26 21:23:43 UTC
HMDB IDHMDB0002007
Secondary Accession Numbers
  • HMDB02007
Metabolite Identification
Common NameTetracosahexaenoic acid
DescriptionThe formation of docosahexaenoic acid(DHA) involves the production of tetracosahexaenoic acid C24:6n-3) from dietary linolenic acid (C18:3n-3) via a series of elongation and desaturation reactions, followed by beta-oxidation of C24:6n-3 to C22:6n-3. DHA is deficient in patients lacking peroxisomes.(PMID: 11734571 ).
Structure
Data?1582752223
Synonyms
ValueSource
6Z,9Z,12Z,15Z,18Z,21Z-Tetracosahexaenoic acidChEBI
all-cis-6,9,12,15,18,21-Tetracosahexaenoic acidChEBI
all-cis-Tetracosa-6,9,12,15,18,21-hexaenoic acidChEBI
C24:6N-3ChEBI
C24:6Omega-3ChEBI
Nisinic acidChEBI
THAChEBI
6Z,9Z,12Z,15Z,18Z,21Z-TetracosahexaenoateGenerator
all-cis-6,9,12,15,18,21-TetracosahexaenoateGenerator
all-cis-Tetracosa-6,9,12,15,18,21-hexaenoateGenerator
NisinateGenerator
TetracosahexaenoateGenerator
Chemical FormulaC24H36O2
Average Molecular Weight356.5414
Monoisotopic Molecular Weight356.271530396
IUPAC Name(6Z,9Z,12Z,15Z,18Z,21Z)-tetracosa-6,9,12,15,18,21-hexaenoic acid
Traditional Name(6Z,9Z,12Z,15Z,18Z,21Z)-tetracosa-6,9,12,15,18,21-hexaenoic acid
CAS Registry Number81247-23-6
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)/b4-3-,7-6-,10-9-,13-12-,16-15-,19-18-
InChI KeyYHGJECVSSKXFCJ-KUBAVDMBSA-N
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
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
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

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 Solubility0.0001 g/LALOGPS
logP7.28ALOGPS
logP7.64ChemAxon
logS-6.6ALOGPS
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
Polarizability42.83 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00kf-5392000000-b5445e76503fcfb65cb6Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00tr-9363100000-90495d16a7f5866e71e7Spectrum
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 (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
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
FooDB IDFDB022791
KNApSAcK IDNot Available
Chemspider ID9967286
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG ID2219657
Wikipedia LinkNisinic acid
METLIN ID6430
PubChem Compound11792612
PDB IDNot Available
ChEBI ID77366
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Ferdinandusse S, Denis S, Mooijer PA, Zhang Z, Reddy JK, Spector AA, Wanders RJ: Identification of the peroxisomal beta-oxidation enzymes involved in the biosynthesis of docosahexaenoic acid. J Lipid Res. 2001 Dec;42(12):1987-95. [PubMed:11734571 ]