Structure Database (LMSD)

Common Name
5-((8Z,11Z)-pentadeca-8,11-dien-1-yl)resorcinol
Systematic Name
5-((8Z,11Z)-pentadeca-8,11-dien-1-yl)benzene-1,3-diol
Synonyms
LM ID
LMPK15030021
Formula
C21H32O2
Exact Mass
Calculate m/z
316.24023
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
View NP-MRD ID(NMR) spectrum

Classification

Category
Main Class
Sub Class
Polyketides [PK]
Phenolic lipids [PK15]
Alkyl resorcinols and derivatives [PK1503]

Biological Context

Cardol diene is a phenol found in cashew nut shell liquid.1 It is schistosomicidal, killing 50, 100, 100, and 100% of S. mansoni worms after 24 hours when used at concentrations of 25, 50, 100, or 200 µM, respectively.2 Cardol diene has an LC50 value of 32.2 µM after 24 and 48 hours against S. mansoni worms. It has been used as a starting material for the synthesis of bis-benzoxazines.3

This information has been provided by Cayman Chemical

References

1. Tyman, J.H., and Kiong, L.S. Long chain phenols: Part XI. Composition of natural cashew nutshell liquid (Anacardium occidentale) from various sources. Lipids 13(8), 525-532 (1978).
2. Attanasi, O.A., Behalo, M.S., Favi, G., et al. Solvent free synthesis of novel mono- and bis-benzoxazines from cashew nut shell liquid components. Curr. Org. Chem. 16(21), 2613-2621 (2012).
3. 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).

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)
UFMJCOLGRWKUKO-UTOQUPLUSA-N
InChi (Click to copy)
InChI=1S/C21H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19-16-20(22)18-21(23)17-19/h4-5,7-8,16-18,22-23H,2-3,6,9-15H2,1H3/b5-4-,8-7-
SMILES (Click to copy)
C1(O)C=C(CCCCCCC/C=C\C/C=C\CCC)C=C(O)C=1

Other Databases

HMDB ID
HMDB0038534
PubChem CID
11702450
Cayman ID
23373

Calculated Physicochemical Properties

Heavy Atoms 23
Rings 1
Aromatic Rings 1
Rotatable Bonds 12
Van der Waals Molecular Volume 352.98
Topological Polar Surface Area 40.46
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 2
logP 6.28
Molar Refractivity 98.98

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Created at
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Updated at
10th Mar 2024