TETRACENOMYCIN D


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	RZKZJERAFMFNMF-UHFFFAOYSA-N
Smiles	Cc1cc(O)cc2cc3C(=O)c4cc(O)cc(O)c4C(=O)c3c(O)c12
InChI	InChI=1S/C19H12O6/c1-7-2-9(20)3-8-4-11-16(18(24)14(7)8)19(25)15-12(17(11)23)5-10(21)6-13(15)22/h2-6,20-22,24H,1H3

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C19H12O6
Molecular Weight	336.29
AlogP	3.24
Hydrogen Bond Acceptor	6.0
Hydrogen Bond Donor	4.0
Number of Rotational Bond	0.0
Polar Surface Area	115.06
Molecular species	ACID
Aromatic Rings	3.0
Heavy Atoms	25.0

Reference

Journal : J Agric Food Chem

Title : Antifungal activities of metabolites produced by a termite-associated Streptomyces canus BYB02.

PubMed ID : 23360202

DOI : 10.1021/jf305210u

Year : 2013

Volume : 61

Issue : 7

First Page : 1521

Last Page : 1524

Authors : Zhang YL, Li S, Jiang DH, Kong LC, Zhang PH, Xu JD.

Abstract : Two main antifungal metabolites resistomycin and tetracenomycin D were isolated and purified from a termite-associated Streptomyces canus BYB02 by column chromatography. The structures of isolated compounds were determined on the basis of extensive spectroscopic analysis. Resistomycin possessed strong activities against mycelial growth of Valsa mali (IC(50) = 1.1 μg/mL) and Magnaporthe grisea (IC(50) = 3.8 μg/mL), which were comparable to those of referenced cycloheximide, with IC(50) values of 2.3 and 0.3 μg/mL, respectively. A further spore germination test showed that resistomycin exhibited potent reduction in spore germination for M. grisea , with an IC(50) value of 5.55 μg/mL. Finally, the in vivo antifungal activity experiment showed that resistomycin possessed significant preventive efficacy against rice blast, which was more potent than that of referenced carbendazim, with control efficacies of 66.8 and 58.7%, respectively. The present results suggest that resistomycin has potential to be used as a fungicide.

Reference

Journal : J Agric Food Chem

Title : Antifungal activities of metabolites produced by a termite-associated Streptomyces canus BYB02.

PubMed ID : 23360202

DOI : 10.1021/jf305210u

Year : 2013

Volume : 61

Issue : 7

First Page : 1521

Last Page : 1524

Authors : Zhang YL, Li S, Jiang DH, Kong LC, Zhang PH, Xu JD.

Reference

Journal : J Agric Food Chem

Title : Antifungal activities of metabolites produced by a termite-associated Streptomyces canus BYB02.

PubMed ID : 23360202

DOI : 10.1021/jf305210u

Year : 2013

Volume : 61

Issue : 7

First Page : 1521

Last Page : 1524

Authors : Zhang YL, Li S, Jiang DH, Kong LC, Zhang PH, Xu JD.

Reference

Journal : J Agric Food Chem

Title : Antifungal activities of metabolites produced by a termite-associated Streptomyces canus BYB02.

PubMed ID : 23360202

DOI : 10.1021/jf305210u

Year : 2013

Volume : 61

Issue : 7

First Page : 1521

Last Page : 1524

Authors : Zhang YL, Li S, Jiang DH, Kong LC, Zhang PH, Xu JD.

Reference

Journal : J Agric Food Chem

Title : Antifungal activities of metabolites produced by a termite-associated Streptomyces canus BYB02.

PubMed ID : 23360202

DOI : 10.1021/jf305210u

Year : 2013

Volume : 61

Issue : 7

First Page : 1521

Last Page : 1524

Authors : Zhang YL, Li S, Jiang DH, Kong LC, Zhang PH, Xu JD.

Reference

Journal : J Agric Food Chem

Title : Antifungal activities of metabolites produced by a termite-associated Streptomyces canus BYB02.

PubMed ID : 23360202

DOI : 10.1021/jf305210u

Year : 2013

Volume : 61

Issue : 7

First Page : 1521

Last Page : 1524

Authors : Zhang YL, Li S, Jiang DH, Kong LC, Zhang PH, Xu JD.

Reference

Journal : J Agric Food Chem

Title : Antifungal activities of metabolites produced by a termite-associated Streptomyces canus BYB02.

PubMed ID : 23360202

DOI : 10.1021/jf305210u

Year : 2013

Volume : 61

Issue : 7

First Page : 1521

Last Page : 1524

Authors : Zhang YL, Li S, Jiang DH, Kong LC, Zhang PH, Xu JD.

Assay Description	Organism	Bioactivity
Antifungal activity against Fusarium oxysporum f. sp. melongenae assessed as inhibition of mycelial growth	Fusarium oxysporum f. sp. melongenae	None
Antifungal activity against Fusarium oxysporum f. sp. cucumerinum assessed as inhibition of mycelial growth	Fusarium oxysporum f. sp. cucumerinum	None
Antifungal activity against Rhizoctonia solani assessed as inhibition of mycelial growth	Rhizoctonia solani	None
Antifungal activity against Dothiorella gregaria assessed as inhibition of mycelial growth	Dothiorella gregaria	None
Antifungal activity against Fusarium graminearum assessed as inhibition of mycelial growth	Fusarium graminearum	None
Antifungal activity against Valsa mali assessed as inhibition of mycelial growth	Valsa mali	25.0 ug.mL-1
Antifungal activity against Magnaporthe grisea assessed as inhibition of mycelial growth	Magnaporthe grisea	25.0 ug.mL-1

Cross References

Resources	Reference
ChEMBL	CHEMBL2289227
PubChem	443788

CONTENTS

Structure
Chemical and Physical Properties