Structure Database (LMSD)
Common Name
6-pentadecyl salicylic acid
Systematic Name
2-hydroxy-6-pentadecylbenzoic acid
Synonyms
- 6-PDSA
3D model of 6-pentadecyl salicylic acid
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Category
Main Class
Sub Class
Biological Context
Anacardic acid, isolated from cashew shells or several other medicinal plants, is the general name given to a family of four different 6-alkyl salicyclic acids having varying degrees of unsaturation in the 15-carbon alkyl chain.1 These compounds are associated with anti-inflammatory, anti-tumor, molluscicidal, and anti-microbial activity. Literature frequently sites and gives the name anacardic acid to the completely-saturated compound (6-pentadecyl salicylic acid). Anacardic acid inhibits the histone acetyltransferase (HAT) activity of the transcription co-activators p300 and p300/CREB-binding protein-associated factor (PCAF) with IC50 values of 8.5 and 5 µM, respectively.2 At 25 µmol/L, anacardic acid suppresses NF-κB activation, inhibits IκB-α phosphorylation, and prohibits p65 nuclear translocation in KBM-5 cells.3
This information has been provided by Cayman Chemical
References
1. Satoh, M., Takeuchi, N., Fujita, T., et al. Synthesis of anacardic acids utilizing an annelation reaction of isoxazoles with ethyl acetoacetate. Chem. Pharm. Bull. (Tokyo) 46(10), 1501-1505 (1998).
References
Taxonomy Information
Curated from
NCBI taxonomy class
Reference
Anacardium occidentale
(#171929)
Magnoliopsida
(#3398)
Antibacterial agents from the cashew Anacardium occidentale (Anacardiaceae) nut shell oil,
J. Agric. Food Chem., 1991
J. Agric. Food Chem., 1991
DOI:
10.1021/jf00002a039
String Representations
InChiKey (Click to copy)
ADFWQBGTDJIESE-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C22H36O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-19-17-15-18-20(23)21(19)22(24)25/h15,17-18,23H,2-14,16H2,1H3,(H,24,25)
SMILES (Click to copy)
C1C=C(CCCCCCCCCCCCCCC)C(C(O)=O)=C(O)C=1
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
25
Rings
1
Aromatic Rings
1
Rotatable Bonds
15
Van der Waals Molecular Volume
381.71
Topological Polar Surface Area
57.53
Hydrogen Bond Donors
2
Hydrogen Bond Acceptors
3
logP
6.72
Molar Refractivity
104.47
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Updated at
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