Details
Stereochemistry | ACHIRAL |
Molecular Formula | C24H48O2 |
Molecular Weight | 368.6367 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCCCCCCCCCCCCCCCCCCCCCC(O)=O
InChI
InChIKey=QZZGJDVWLFXDLK-UHFFFAOYSA-N
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)
Molecular Formula | C24H48O2 |
Molecular Weight | 368.6367 |
Charge | 0 |
Count |
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Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/15565636Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/25702090 | https://www.ncbi.nlm.nih.gov/pubmed/15653672 | https://www.ncbi.nlm.nih.gov/pubmed/1194916 | https://www.ncbi.nlm.nih.gov/pubmed/18998246
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15565636
Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/25702090 | https://www.ncbi.nlm.nih.gov/pubmed/15653672 | https://www.ncbi.nlm.nih.gov/pubmed/1194916 | https://www.ncbi.nlm.nih.gov/pubmed/18998246
Lignoceric Acid (tetracosanoic acid) is a saturated fatty acid with a 24-carbon backbone, that occurs naturally in wood tar, various cerebrosides, and in small amount in most natural fats. In mammals, it is found in cerebrosides and is synthesized during brain development. The deficient peroxisomal oxidation of very-long-chain fatty acids, including lignoceric acid, contributes to certain syndromes, including Zellweger cerebro-hepato-renal syndrome and X chromosome-linked adrenoleukodystrophy. Lignoceric acid is also a product of lignin production.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL1287628 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15565636 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Diagnostic | Unknown Approved UseUnknown |
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Diagnostic | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Characterization of novel structures of mannosylinositolphosphorylceramides from the yeast forms of Sporothrix schenckii. | 2001 Aug |
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Stable ordering in Langmuir-Blodgett films. | 2001 Aug 17 |
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Diagnostic patterns of very-long-chain fatty acids in plasma of patients with X-linked adrenoleukodystrophy. | 2001 Aug 25 |
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Lupeol esters from the twig bark of Japanese pear (Pyrus serotina Rehd.) cv. Shinko. | 2001 May |
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Peroxisomal fatty acid oxidation and cellular redox. | 2002 |
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Constituents of Gnetum montanum. | 2002 Feb |
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Detection of tissues of the central nervous system (CNS) as specified risk material (SRM) in meat products by means of gas chromatography-mass spectrometry (GC-MS). | 2002 Mar-Apr |
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In-house validation of an improved sample extraction and clean-up method for GC determination of isomers of nervonic acid in meat products. | 2003 Jun |
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Expression of the Arabidopsis ADS1 gene in Brassica juncea results in a decreased level of total saturated fatty acids. | 2003 May |
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Structural elucidation of fritillahupehin from bulbs of Fritillaria hupehensis Hsiao et K.C. Hsia. | 2004 Mar |
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Natural killer T cells and rheumatoid arthritis: friend or foe? | 2005 |
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[Studies on chemical constituents from roots of Peucedanum praeruptorum II]. | 2006 Aug |
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Uptake of the glycosphingolipid sulfatide in the gastrointestinal tract and pancreas in vivo and in isolated islets of Langerhans. | 2006 Oct 17 |
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Induction of lipid peroxidation and decrease of antioxidant defenses in symptomatic and asymptomatic patients with X-linked adrenoleukodystrophy. | 2007 Nov |
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Fatty acid and carotenoid production by Sporobolomyces ruberrimus when using technical glycerol and ammonium sulfate. | 2007 Oct |
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Prolongation of cardiac allograft survival by rapamycin and the invariant natural killer T cell glycolipid agonist OCH. | 2008 Aug 15 |
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[Chemical constituents from dried sorophore of cultured Cordyceps militaris]. | 2008 Dec |
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Secondary metabolites of Cinnamosma madagascariensis and their alpha-glucosidase inhibitory properties. | 2008 Jan |
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[Chemical constituents from stems of Schisandra propinqua]. | 2008 Mar |
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Phage display-derived recombinant antibodies with TCR-like specificity against alpha-galactosylceramide and its analogues in complex with human CD1d molecules. | 2008 Mar |
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Petiveria alliacea extracts uses multiple mechanisms to inhibit growth of human and mouse tumoral cells. | 2008 Nov 18 |
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[Chemical constituents of Solanum cathayanum]. | 2008 Sep |
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Very long chain fatty acid levels in patients diagnosed with multiple sclerosis. | 2009 Dec |
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Engineering and validation of a novel lipid thin film for biomembrane modeling in lipophilicity determination of drugs and xenobiotics. | 2009 Sep 7 |
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Cytochrome P450 family member CYP704B2 catalyzes the {omega}-hydroxylation of fatty acids and is required for anther cutin biosynthesis and pollen exine formation in rice. | 2010 Jan |
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Synthesis and biological activity of alpha-L-fucosyl ceramides, analogues of the potent agonist, alpha-D-galactosyl ceramide KRN7000. | 2010 Jun 1 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18998246
Unknown
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15565636
Human skin fibroblasts were used for activity evaluation. Cell cultures were washed twice with serum-free DMEM F-12 and cultured for another 24 h in DMEM F-12 (supplemented with 1% FBS) medium before treatment with VLCFAs. Varying concentrations (0.5–10 mg/ml) of lignoceric acid (a 24-carbon compound) or cerotic acid (a 26-carbon compound) were added to the cell cultures and cells were further cultured for 48 h. Culture medium containing VLCFAs was changed once after 24 h. of treatment and replaced with fresh culture medium containing the same concentrations of VLCFAs as originally added. NADPH oxidase (NOX) activity was measured in cell homogenates at 37C using lucigenin and NADPH. Enzymic activity of NOX was significantly ( p<0.001) increased in dermal fibroblasts following treatment with lignoceric acid or cerotic acid.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 17:44:59 GMT 2023
by
admin
on
Fri Dec 15 17:44:59 GMT 2023
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Record UNII |
RK3VCW5Y1L
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C68439
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NCI_THESAURUS |
C68421
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DSLD |
1506 (Number of products:1)
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11197
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557-59-5
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DTXSID6021664
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C68387
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RK3VCW5Y1L
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28866
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LIGNOCERIC ACID
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209-180-7
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m6811
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PRIMARY | Merck Index |
Related Record | Type | Details | ||
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LIPID -> FATTY ACID |
TUNISIAN SOURCE
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LIPID -> FATTY ACID |
Value was not available.
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LIPID -> FATTY ACID |
Range values as of FAO/WHO Codex Alimentarius Committee on commercial fats and oils.(unspecified percent)
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