BRUSSALEXIN A


Source	Gaulton A, Kale N, van Westen GJ, Bellis LJ, Bento AP, Davies M, Hersey A, Papadatos G, Forster M, Wege P, Overington JP. A large-scale crop protection bioassay data set. Sci Data. 2015 Jul 7;2:150032. Read more ...


Active Pharmaceutical Ingredients Bioactive chemicals	Exact Similarity SubStructure	Threshold (%) >= 70

Structure


InChI Key	OBOJQFIBBALTIN-UHFFFAOYSA-N
Smiles	C=CCNC(=O)SCc1c[nH]c2ccccc12
InChI	InChI=1S/C13H14N2OS/c1-2-7-14-13(16)17-9-10-8-15-12-6-4-3-5-11(10)12/h2-6,8,15H,1,7,9H2,(H,14,16)

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C13H14N2OS
Molecular Weight	246.33
AlogP	3.07
Hydrogen Bond Acceptor	2.0
Hydrogen Bond Donor	2.0
Number of Rotational Bond	5.0
Polar Surface Area	70.19
Molecular species	NEUTRAL
Aromatic Rings	2.0
Heavy Atoms	17.0

Reference

Journal : Bioorg. Med. Chem.

Title : The cruciferous phytoalexins rapalexin A, brussalexin A and erucalexin: chemistry and metabolism in Leptosphaeria maculans.

PubMed ID : 22672981

DOI : 10.1016/j.bmc.2012.05.020

Year : 2012

Volume : 20

Issue : 13

First Page : 3991

Last Page : 3996

Authors : Pedras MS, Sarma-Mamillapalle VK.

Abstract : The interactions of the cruciferous phytoalexins rapalexin A (1), brussalexin A (2) and erucalexin (3) with the fungal plant pathogen Leptosphaeria maculans were analyzed and their inhibitory activities against this pathogen were determined. The reaction of L. maculans to N-methyl S-(indolyl-3-methyl)carbamodithioate, an analogue of brussalexin A, was also investigated. Rapalexin A was resistant to metabolism and was the most inhibitory of all compounds tested, suggesting that increasing concentrations of rapalexin A in Brassica species would improve their disease resistance to L. maculans. By contrast, erucalexin was quickly detoxified by reduction to yield 3-dihydroerucalexins. The relative configurations of the diastereomeric mixture of dihydroerucalexins were established by 1D (1)H nuclear Overhauser enhancement spectroscopy (NOE). Brussalexin A was chemically unstable decomposing mainly to indolyl-3-methanol, a product with anti-cancer properties. For this reason, brussalexin A might be of interest to use as a prodrug.

Reference

Journal : Bioorg. Med. Chem.

Title : The cruciferous phytoalexins rapalexin A, brussalexin A and erucalexin: chemistry and metabolism in Leptosphaeria maculans.

PubMed ID : 22672981

DOI : 10.1016/j.bmc.2012.05.020

Year : 2012

Volume : 20

Issue : 13

First Page : 3991

Last Page : 3996

Authors : Pedras MS, Sarma-Mamillapalle VK.

Reference

Journal : Bioorg. Med. Chem.

Title : The cruciferous phytoalexins rapalexin A, brussalexin A and erucalexin: chemistry and metabolism in Leptosphaeria maculans.

PubMed ID : 22672981

DOI : 10.1016/j.bmc.2012.05.020

Year : 2012

Volume : 20

Issue : 13

First Page : 3991

Last Page : 3996

Authors : Pedras MS, Sarma-Mamillapalle VK.

Reference

Journal : Bioorg. Med. Chem.

Title : The cruciferous phytoalexins rapalexin A, brussalexin A and erucalexin: chemistry and metabolism in Leptosphaeria maculans.

PubMed ID : 22672981

DOI : 10.1016/j.bmc.2012.05.020

Year : 2012

Volume : 20

Issue : 13

First Page : 3991

Last Page : 3996

Authors : Pedras MS, Sarma-Mamillapalle VK.

Reference

Journal : Bioorg. Med. Chem.

Title : The cruciferous phytoalexins rapalexin A, brussalexin A and erucalexin: chemistry and metabolism in Leptosphaeria maculans.

PubMed ID : 22672981

DOI : 10.1016/j.bmc.2012.05.020

Year : 2012

Volume : 20

Issue : 13

First Page : 3991

Last Page : 3996

Authors : Pedras MS, Sarma-Mamillapalle VK.

Assay Description	Organism	Bioactivity
Half life in water	None	48.0 hr
Half life in potato dextrose agar medium	None	15.0 hr
Antifungal activity against Leptosphaeria maculans assessed as mycelial radial growth inhibition on potato dextrose agar at 0.10 mM relative to control	Leptosphaeria maculans	7.0 %
Antifungal activity against Leptosphaeria maculans assessed as mycelial radial growth inhibition on potato dextrose agar at 0.20 mM relative to control	Leptosphaeria maculans	25.0 %
Antifungal activity against Leptosphaeria maculans assessed as mycelial radial growth inhibition on potato dextrose agar at 0.50 mM relative to control	Leptosphaeria maculans	43.0 %

Cross References

Resources	Reference
ChEMBL	CHEMBL2253034
PubChem	16048626

CONTENTS

Structure
Chemical and Physical Properties