| 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 ). |
| Structure |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
|
| Synonyms |
- Lignocerate
- Lignoceric acid
- N-Tetracosanoate
- N-Tetracosanoic acid
- Tetracosanoate
- 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 |
|
| Direct Parent |
Straight Chain Fatty Acids |
| Ontology |
| Status |
Detected and Quantified |
| Origin |
|
| 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 |
|
| Spectra |
|
|
| Biological Properties |
| Cellular Locations |
- Cytoplasm
- Extracellular
- Membrane (predicted from logP)
- Peroxisome
|
| Biofluid Locations |
|
| Tissue Location |
|
| Pathways |
| Name |
SMPDB Link |
KEGG Link |
| Beta Oxidation of Very Long Chain Fatty Acids |
SMP00052
|
map01040
|
|
| Normal Concentrations |
|
| Blood |
Detected and Quantified |
|
0.262 +/- 0.014 uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Blood |
Detected and Quantified |
|
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 |
| External Links |
| DrugBank ID |
Not Available |
| Phenol Explorer Compound ID |
Not Available |
| Phenol Explorer Metabolite ID |
Not Available |
| FoodDB ID |
FDB021823 |
| KNApSAcK ID |
C00001223  |
| Chemspider ID |
10724  |
| KEGG Compound ID |
C08320  |
| BioCyc ID |
TETRACOSANOATE  |
| BiGG ID |
2218057  |
| Wikipedia Link |
Tetracosanoic acid  |
| NuGOwiki Link |
HMDB02003  |
| Metagene Link |
HMDB02003  |
| METLIN ID |
6427  |
| PubChem Compound |
11197  |
| PDB ID |
Not Available |
| ChEBI ID |
28866  |
| References |
| Synthesis Reference |
Not Available |
| Material Safety Data Sheet (MSDS) |
Download (PDF)
|
| General References |
- 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
- 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
- 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
|