N-METHYL-S-(INDOLYL-3-METHYL)CARBAMODITHIOATE


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	NIXSRAWVFMDSBC-UHFFFAOYSA-N
Smiles	CNC(=S)SCc1c[nH]c2ccccc12
InChI	InChI=1S/C11H12N2S2/c1-12-11(14)15-7-8-6-13-10-5-3-2-4-9(8)10/h2-6,13H,7H2,1H3,(H,12,14)

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C11H12N2S2
Molecular Weight	236.36
AlogP	3.55
Hydrogen Bond Acceptor	2.0
Hydrogen Bond Donor	2.0
Number of Rotational Bond	4.0
Polar Surface Area	85.21
Molecular species	NEUTRAL
Aromatic Rings	2.0
Heavy Atoms	15.0

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	20.0 hr
Half life in potato dextrose agar medium	None	24.0 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	17.0 %
Antifungal activity against Leptosphaeria maculans assessed as mycelial radial growth inhibition on potato dextrose agar at 0.20 mM relative to control	Leptosphaeria maculans	35.0 %
Antifungal activity against Leptosphaeria maculans assessed as mycelial radial growth inhibition on potato dextrose agar at 0.50 mM relative to control	Leptosphaeria maculans	61.0 %

Cross References

Resources	Reference
ChEMBL	CHEMBL2253036
PubChem	76330012

CONTENTS

Structure
Chemical and Physical Properties