Structure Database (LMSD)
Common Name
Anacardic acid
Systematic Name
2-hydroxy-6-[(8Z,11Z)-pentadeca-8,11,14-trienyl]benzoic acid
Synonyms
3D model of Anacardic 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 triene is a polyunsaturated form of anacardic acid that has been found in cashew nut shell liquid.1 It inhibits soybean lipoxygenase-1 (IC50 = 60 µM in an enzyme assay) and inhibits superoxide production by xanthine oxidase by 82% when used at a concentration of 88 µM.2,1 Anacardic acid triene is active against S. mutans and S. aureus, including the methicillin-resistant S. aureus (MRSA) strain ATCC 33591 (MICs = 1.56, 6.25, and 6.25 µg/ml, respectively).3 It also inhibits NADH oxidase (IC50 = 1.3 µg/ml), an enzyme involved in bacterial respiration. Anacardic acid triene is molluscicidal, inducing toxicity in B. glabrata (LC50 = 0.35 ppm), but is inactive against S. mansoni parasites.4,5
This information has been provided by Cayman Chemical
References
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)
QUVGEKPNSCFQIR-UTOQUPLUSA-N
InChi (Click to copy)
InChI=1S/C22H30O3/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/h2,4-5,7-8,15,17-18,23H,1,3,6,9-14,16H2,(H,24,25)/b5-4-,8-7-
SMILES (Click to copy)
C1C=C(CCCCCCC/C=C\C/C=C\CC=C)C(C(O)=O)=C(O)C=1
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
25
Rings
1
Aromatic Rings
1
Rotatable Bonds
13
Van der Waals Molecular Volume
373.79
Topological Polar Surface Area
57.53
Hydrogen Bond Donors
2
Hydrogen Bond Acceptors
3
logP
6.05
Molar Refractivity
104.18
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