BLASTICIDIN S

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C17H26N8O5
Molecular Weight	422.4389
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN(CC[C@H](N)CC(=O)N[C@@H]1C=C[C@H](O[C@H]1C(O)=O)N2C=CC(N)=NC2=O)C(N)=N

InChI

InChIKey=CXNPLSGKWMLZPZ-GIFSMMMISA-N

InChI=1S/C17H26N8O5/c1-24(16(20)21)6-4-9(18)8-12(26)22-10-2-3-13(30-14(10)15(27)28)25-7-5-11(19)23-17(25)29/h2-3,5,7,9-10,13-14H,4,6,8,18H2,1H3,(H3,20,21)(H,22,26)(H,27,28)(H2,19,23,29)/t9-,10+,13-,14+/m0/s1

HIDE SMILES / InChI

Molecular Formula	C17H26N8O5
Molecular Weight	422.4389
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23879927
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/4860846 | https://www.ncbi.nlm.nih.gov/pubmed/892936

Blasticidin S is a metabolite of Streptomyces griseochromogenes and was formerly used in practice as a fungicide against a phytopathogenic fungus, Pyricularia oryzae. Blasticidin S inhibits protein synthesis of both prokaryotic and eukaryotic organisms by interacting with their ribosomes. Blasticidin S, a protein synthesis inhibitor, inhibits aflatoxin production of Aspergillus flavus without affecting fungal growth. It has been demonstrated that blasticidin S also exhibits antibacterial activity, toxicity to mammalians and tumor-inhibitory activity.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
DNA synthesis involved in DNA replication 7 Target ID: GO:0090592 Sources: https://www.ncbi.nlm.nih.gov/pubmed/4860846	Inhibitor 8297
Escherichia coli 82 Target ID: CHEMBL354 Sources: https://www.ncbi.nlm.nih.gov/pubmed/4860846	Inhibitor 8297
Bacterial 70S ribosome 179 Target ID: CHEMBL2363135 Sources: https://www.ncbi.nlm.nih.gov/pubmed/4860846 \| https://www.ncbi.nlm.nih.gov/pubmed/23824292 \| https://www.ncbi.nlm.nih.gov/pubmed/27739094	Binding Agent 1064
28S ribosomal RNA 1 Target ID: 28S ribosomal RNA Sources: https://www.ncbi.nlm.nih.gov/pubmed/12970763	Binding Agent 1064

Conditions

Condition	Modality	Targets	Highest Phase	Product
Leukemia 87 Sources: https://www.ncbi.nlm.nih.gov/pubmed/892936 https://www.ncbi.nlm.nih.gov/pubmed/718932 https://www.ncbi.nlm.nih.gov/pubmed/12970763	Primary		Basic research	Unknown Approved Use Unknown
Escherichia coli Infections 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/4860846	Curative		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Inhibition of protein synthesis by blasticidin S. II. Studies on the site of action in E. coli polypeptide synthesizing systems.	1966 Dec	4860846

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Increase of E. coli cell number was completely suppressed at 2.3 X 10(-4) M of Blasticidin S and the viable cell number was markedly decreased at 9.2 x 10(-4 ) M. 2.3X 10(-4) M was regarded as the minimal growth-inhibitory concentration against E. coli and B. megaterium.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 18:51:38 GMT 2023` Edited by `admin` on `Fri Dec 15 18:51:38 GMT 2023`
Record UNII	83U64J9U23
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BLASTICIDIN S

Common Name

English

BLASTICIDIN S [MI]

Common Name

English

1-(1'-CYTOSINYL)-4-(L-3'-AMINO-5'-(1''-N-METHYLGUANIDINO)-VALERYLAMINO)-1,2,3,4-TETRADEOXY-.BETA.-D-ERYTHRO-HEX-2-ENURONIC ACID

Common Name

English

CYTOSININE-BLASTIDIC ACID CONJUGATE

Common Name

English

BLASTICIDIN-S [HSDB]

Common Name

English

Classification Tree Code System Code

EPA PESTICIDE CODE

6326