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
C22H30O3
Exact Mass
Calculate m/z
342.219496
Status
Curated
Show lipids differing only in stereochemistry/bond geometry

Classification

Category
Main Class
Sub Class
Polyketides [PK]
Phenolic lipids [PK15]
Anacardic acids and derivatives [PK1504]

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

1. Alvarenga, T.A., de Oliveira, P.F., de Souza, J.M., et al. Schistosomicidal activity of alkyl-phenols from the cashew Anacardium occidentale against Schistosoma mansoni adult worms. J. Agric. Food Chem. 64(46), 8821-8827 (2016).
2. Kubo, I., Nihei, K., and Tsujimoto, K. Antibacterial action of anacardic acids against methicillin resistant Staphylococcus aureus (MRSA). J. Agric. Food Chem. 51(26), 7624-7628 (2003).
3. Masuoka, N., and Kubo, I. Characterization of xanthine oxidase inhibition by anacardic acids. Biochim. Biophys. Acta 1688(3), 245-249 (2004).
4. Shobha, S.V., Ramadoss, C.S., and Ravindranath, B. Inhibition of soybean lipoxygenase-1 by anacardic acids, cardols, and cardanols. J. Nat. Prod. 57(12), 1755-1757 (1994).
5. Sullivan, J.T., Richards, C.S., Lloyd, H.A., et al. Anacardic acid: Molluscicide in cashew nut shell liquid. Planta Med. 44(3), 175-177 (1982).

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
183726
PubChem CID
9875131
Cayman ID
26611

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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