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Human Metabolome Database Version 3.5

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Showing metabocard for Tetracosanoic acid (HMDB02003)

Record Information
Version 3.5
Creation Date 2006-05-22 08:17:31 -0600
Update Date 2013-02-08 17:11:10 -0700
HMDB ID HMDB02003
Secondary Accession Numbers None
Metabolite Identification
Common Name Tetracosanoic acid
Description Lignoceric acid, also tetracosanoic acid, is a normal carboxylic acid, a very long chain fatty acid (VLCFA). Very long chain fatty acids (VLCFAs) are exclusively oxidized in peroxisomes and their levels are significantly increased in tissues of patients with peroxisomal disorders. (PMID 15565636 Link_out).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. Lignocerate
  2. Lignoceric acid
  3. N-Tetracosanoate
  4. N-Tetracosanoic acid
  5. Tetracosanoate
  6. Tetracosanoic acid
Chemical Formula C24H48O2
Average Molecular Weight 368.6367
Monoisotopic Molecular Weight 368.36543078
IUPAC Name tetracosanoic acid
Traditional IUPAC Name lignoceric acid
CAS Registry Number 557-59-5
SMILES CCCCCCCCCCCCCCCCCCCCCCCC(O)=O
InChI Identifier InChI=1S/C24H48O2/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/h2-23H2,1H3,(H,25,26)
InChI Key QZZGJDVWLFXDLK-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Fatty Acids and Conjugates
Sub Class Straight Chain Fatty Acids
Other Descriptors
  • Aliphatic Acyclic Compounds
  • Organic Compounds
  • Saturated fatty acids(KEGG)
  • Straight chain fatty acids(KEGG)
  • Straight chain fatty acids(Lipidmaps)
  • straight-chain saturated fatty acid(ChEBI)
  • very long-chain fatty acid(ChEBI)
Substituents
  • Carboxylic Acid
Direct Parent Straight Chain Fatty Acids
Ontology
Status Detected and Quantified
Origin
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
  • Peroxisome
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 84.2 °C Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 2.270E-05 g/L ALOGPS
LogP 9.56 ALOGPS
LogP 9.81 ChemAxon
LogS -7.21 ALOGPS
pKa (strongest acidic) 4.95 ChemAxon
Hydrogen Acceptor Count 2 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 37.3 A2 ChemAxon
Rotatable Bond Count 22 ChemAxon
Refractivity 113.89 ChemAxon
Polarizability 51.57 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
Gas-MS Spectrum
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum EI-B (HITACHI M-80B)
MS/MS Spectrum GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies )
MS/MS Spectrum LC-ESI-QTOF (UPLC Q-Tof Premier, Waters)
MS/MS Spectrum GC-MS
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
  • Peroxisome
Biofluid Locations
  • Blood
Tissue Location
  • Fibroblasts
Pathways
Name SMPDB Link KEGG Link
Beta Oxidation of Very Long Chain Fatty Acids SMP00052 map01040 Link_out
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
Article_icon
0.262 +/- 0.014 uM Adult (>18 years old) Both Normal Not Available
Blood Detected and Quantified
Article_icon
0.930 +/- 0.194 uM Adult (>18 years old) Both Normal Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB021823
KNApSAcK ID C00001223 Link_out
Chemspider ID 10724 Link_out
KEGG Compound ID C08320 Link_out
BioCyc ID TETRACOSANOATE Link_out
BiGG ID 2218057 Link_out
Wikipedia Link Tetracosanoic acid Link_out
NuGOwiki Link HMDB02003 Link_out
Metagene Link HMDB02003 Link_out
METLIN ID 6427 Link_out
PubChem Compound 11197 Link_out
PDB ID Not Available
ChEBI ID 28866 Link_out
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Download (PDF)
General References
  1. Galloway JH, Cartwright IJ, Bennett MJ: Abnormal myocardial lipid composition in an infant with type II glutaric aciduria. J Lipid Res. 1987 Mar;28(3):279-84. Pubmed: 3572253 Link_out
  2. Dhaunsi GS, Kaur J, Alsaeid K, Turner RB, Bitar MS: Very long chain fatty acids activate NADPH oxidase in human dermal fibroblasts. Cell Biochem Funct. 2005 Jan-Feb;23(1):65-8. Pubmed: 15565636 Link_out
  3. Petroni A, Blasevich M, Uziel G: Effects of the testosterone metabolite dihydrotestosterone and 5 alpha-androstan-3 alpha,17 beta-diol on very long chain fatty acid metabolism in X-adrenoleukodystrophic fibroblasts. Life Sci. 2003 Aug 8;73(12):1567-75. Pubmed: 12865096 Link_out
Enzymes
Name: Long-chain-fatty-acid--CoA ligase 1
Reactions:
    Gene Name: ACSL1
    Uniprot ID: P33121 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA