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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-05-22 14:17:31 UTC
Update Date2022-03-07 02:49:12 UTC
HMDB IDHMDB0002007
Secondary Accession Numbers
  • HMDB02007
Metabolite Identification
Common NameTetracosahexaenoic acid
DescriptionTetracosahexaenoic acid, also known as C24:6N-3 or C24:6omega-3, 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. Based on a literature review a significant number of articles have been published on Tetracosahexaenoic acid.
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
Physiological effectNot Available
Disposition
Process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+200.36431661259
DarkChem[M-H]-199.09831661259
DeepCCS[M+H]+193.27330932474
DeepCCS[M-H]-190.91530932474
DeepCCS[M-2H]-223.97130932474
DeepCCS[M+Na]+199.36630932474
AllCCS[M+H]+197.132859911
AllCCS[M+H-H2O]+194.432859911
AllCCS[M+NH4]+199.632859911
AllCCS[M+Na]+200.332859911
AllCCS[M-H]-195.432859911
AllCCS[M+Na-2H]-197.932859911
AllCCS[M+HCOO]-200.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Tetracosahexaenoic acidCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCC(O)=O4183.2Standard polar33892256
Tetracosahexaenoic acidCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCC(O)=O2405.4Standard non polar33892256
Tetracosahexaenoic acidCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCC(O)=O2721.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Tetracosahexaenoic acid,1TMS,isomer #1CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCCCC(=O)O[Si](C)(C)C2747.9Semi standard non polar33892256
Tetracosahexaenoic acid,1TBDMS,isomer #1CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCCCC(=O)O[Si](C)(C)C(C)(C)C3004.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Tetracosahexaenoic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-00kf-5392000000-b5445e76503fcfb65cb62017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tetracosahexaenoic acid GC-MS (1 TMS) - 70eV, Positivesplash10-00tr-9363100000-90495d16a7f5866e71e72017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tetracosahexaenoic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetracosahexaenoic acid 10V, Positive-QTOFsplash10-000i-0009000000-0aecad3f10eefdf7d1b12017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetracosahexaenoic acid 20V, Positive-QTOFsplash10-03ds-4559000000-d044187c05f199f03f752017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetracosahexaenoic acid 40V, Positive-QTOFsplash10-01p2-9673000000-fe0e36efc6429aef79142017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetracosahexaenoic acid 10V, Negative-QTOFsplash10-0a4i-0009000000-2a2103fe5e22d781b9b92017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetracosahexaenoic acid 20V, Negative-QTOFsplash10-0bti-0009000000-093b42344e6284ef767d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetracosahexaenoic acid 40V, Negative-QTOFsplash10-0a4l-9123000000-94c48fd43abe43b10fe72017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetracosahexaenoic acid 10V, Positive-QTOFsplash10-0a4r-1119000000-6b60214ee63c5d7a07ae2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetracosahexaenoic acid 20V, Positive-QTOFsplash10-05ar-7966000000-0bb0202f87452308f75b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetracosahexaenoic acid 40V, Positive-QTOFsplash10-053u-9710000000-e8579e42e6d94744c4492021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetracosahexaenoic acid 10V, Negative-QTOFsplash10-0a4i-0009000000-96a0c6d373c7eb7508602021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetracosahexaenoic acid 20V, Negative-QTOFsplash10-0a4r-1009000000-f3cf175eec093aa8f7842021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetracosahexaenoic acid 40V, Negative-QTOFsplash10-052f-9033000000-5d444b34f231862080c22021-09-23Wishart LabView Spectrum
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
MarkerDB IDNot Available
Good Scents 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 ]