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Record Information
Version1.0
Creation Date2016-10-03 18:40:51 UTC
Update Date2020-06-04 20:33:22 UTC
BMDB IDBMDB0006323
Secondary Accession Numbers
  • BMDB06323
Metabolite Identification
Common NameTetracosapentaenoic acid (24:5n-3)
DescriptionTetracosapentaenoic acid (24:5N-3), also known as 9Z,12Z,15Z,18Z,21Z-tetracosapentaenoate or 24:5 (N-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. Tetracosapentaenoic acid (24:5N-3) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Tetracosapentaenoic acid (24:5N-3) participates in a number of enzymatic reactions, within cattle. In particular, Tetracosapentaenoic acid (24:5N-3) can be biosynthesized from docosapentaenoic acid (22N-3) through the action of the enzyme elongation OF very long chain fatty acids protein 4. In addition, Tetracosapentaenoic acid (24:5N-3) can be converted into tetracosahexaenoic acid; which is catalyzed by the enzyme fatty acid desaturase 2. In cattle, tetracosapentaenoic acid (24:5N-3) is involved in the metabolic pathway called the Alpha linolenic Acid and linoleic Acid metabolism pathway.
Structure
Thumb
Synonyms
ValueSource
24:5 (N-3)ChEBI
24:5 (Omega-3)ChEBI
9Z,12Z,15Z,18Z,21Z-Tetracosapentaenoic acidChEBI
all-cis-Tetracosa-9,12,15,18,21-pentaenoic acidChEBI
9Z,12Z,15Z,18Z,21Z-TetracosapentaenoateGenerator
all-cis-Tetracosa-9,12,15,18,21-pentaenoateGenerator
Tetracosapentaenoate (24:5N-3)Generator
(9Z,12Z,15Z,18Z,21Z)-TetracosapentaenateHMDB
(9Z,12Z,15Z,18Z,21Z)-TetracosapentaenoateHMDB
(9Z,12Z,15Z,18Z,21Z)-Tetracosapentaenoic acidHMDB
TetracosapentaenateHMDB
Chemical FormulaC24H38O2
Average Molecular Weight358.5573
Monoisotopic Molecular Weight358.28718046
IUPAC Name(9Z,12Z,15Z,18Z,21Z)-tetracosa-9,12,15,18,21-pentaenoic acid
Traditional Name(9Z,12Z,15Z,18Z,21Z)-tetracosa-9,12,15,18,21-pentaenoic acid
CAS Registry NumberNot Available
SMILES
CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O
InChI Identifier
InChI=1S/C24H38O2/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/h3-4,6-7,9-10,12-13,15-16H,2,5,8,11,14,17-23H2,1H3,(H,25,26)/b4-3-,7-6-,10-9-,13-12-,16-15-
InChI KeyNPTIBOCVSPURCS-JLNKQSITSA-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
StatusDetected and Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Adiposome
  • Cell membrane
  • Cytoplasm
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP7.59ALOGPS
logP8ChemAxon
logS-6.8ALOGPS
pKa (Strongest Acidic)4.99ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count17ChemAxon
Refractivity119.47 m³·mol⁻¹ChemAxon
Polarizability44.67 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0573-4291000000-6ea1ffbff016c500f881View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00bi-8592200000-44739218ec66d2cd0c9eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0009000000-4db308c9cea35a6a7145View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dm-4449000000-f4b29814b97a0684aa6bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01p5-9772000000-4427f74dace33638a7c1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0009000000-9983909c1bd7f6f6f639View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0bti-0009000000-68af15c6bf0d9194cf35View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9122000000-d4f99830ed97426002daView in MoNA
Biological Properties
Cellular Locations
  • Adiposome
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Milk
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
MilkDetected and Quantified2203.276 +/- 529.902 uMNot SpecifiedNot Specified
Normal
    • M. Ferrand et al....
details
MilkDetected and Quantified948.245 +/- 390.454 uMNot SpecifiedNot Specified
Normal
    • M. Ferrand et al....
details
MilkDetected and Quantified2091.718 +/- 446.233 uMNot SpecifiedNot Specified
Normal
    • M. Ferrand et al....
details
Abnormal Concentrations
Not Available
HMDB IDHMDB0006323
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023890
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDCPD-7421
BiGG ID2219655
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound52921801
PDB IDNot Available
ChEBI ID77360
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. M. Ferrand, B. Huquet. S. Barbey, F. Barillet, F. Faucon, H. Larroque, O. Leray, J.M. Trommenschlager, M. Brochard (2011). M. Ferrand et al. Determination of fatty acid profile in cow's milk using mid-infrared spectrometry: Interest of applying a variable selection by genetic algorithms before a PLS regression. Chemometrics and Intelligent Laboratory Systems 106 (2011) 183?189. Chemometrics and Intelligent Laboratory Systems.

Enzymes

General function:
Not Available
Specific function:
Catalyzes the first and rate-limiting reaction of the four reactions that constitute the long-chain fatty acids elongation cycle. This endoplasmic reticulum-bound enzymatic process allows the addition of 2 carbons to the chain of long- and very long-chain fatty acids (VLCFAs) per cycle. Condensing enzyme that acts specifically toward polyunsaturated acyl-CoA with the higher activity toward C18:3(n-6) acyl-CoA. May participate in the production of monounsaturated and of polyunsaturated VLCFAs of different chain lengths that are involved in multiple biological processes as precursors of membrane lipids and lipid mediators (By similarity). In conditions where the essential linoleic and alpha linoleic fatty acids are lacking it is also involved in the synthesis of Mead acid from oleic acid (By similarity).
Gene Name:
ELOVL5
Uniprot ID:
Q2KJD9
Molecular weight:
35377.0
Reactions
Clupanodonic acid → Tetracosapentaenoic acid (24:5n-3)details