Structure Database (LMSD)

Common Name
6-pentadecyl salicylic acid
Systematic Name
2-hydroxy-6-pentadecylbenzoic acid
Synonyms
  • 6-PDSA
LM ID
LMPK15040002
Formula
Exact Mass
Calculate m/z
348.266446
Status
Curated

Classification

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

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

KEGG ID
HMDB ID
CHEBI ID
PubChem CID
Cayman ID

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

Admin

Created at
-
Updated at
-