Structure Database (LMSD)

Common Name
Anacardic acid
Systematic Name
2-hydroxy-6-[(8Z,11Z)-pentadeca-8,11,14-trienyl]benzoic acid
Synonyms
LM ID
LMPK15040001
Formula
Exact Mass
Calculate m/z
342.219496
Status
Curated

Classification

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

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

CHEBI ID
PubChem CID
Cayman ID

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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Updated at
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