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 11 Target ID: GO:0090592 Sources: https://www.ncbi.nlm.nih.gov/pubmed/4860846	Inhibitor 8504
Escherichia coli 82 Target ID: CHEMBL354 Sources: https://www.ncbi.nlm.nih.gov/pubmed/4860846	Inhibitor 8504
Bacterial 70S ribosome 180 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 1076
28S ribosomal RNA 1 Target ID: 28S ribosomal RNA Sources: https://www.ncbi.nlm.nih.gov/pubmed/12970763	Binding Agent 1076

Conditions

Condition	Modality	Targets	Highest Phase	Product
Leukemia 72 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
New metabolic pathway for converting blasticidin S in Aspergillus flavus and inhibitory activity of aflatoxin production by blasticidin S metabolites.	2013-08-21	23879927
A mouse leukemia cell mutant resistant to blasticidin S.	1977-08-15	892936
Inhibition of protein synthesis by blasticidin S. II. Studies on the site of action in E. coli polypeptide synthesizing systems.	1966-12	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 `Mon Mar 31 19:22:56 GMT 2025` Edited by `admin` on `Mon Mar 31 19:22:56 GMT 2025`
Record UNII	83U64J9U23
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BLASTICIDIN S

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

Preferred Name

English

BLASTICIDIN S [MI]

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