HYGROMYCIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C23H29NO12
Molecular Weight	511.4759
Optical Activity	UNSPECIFIED
Defined Stereocenters	10 / 10
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@]12OCO[C@@]1([H])[C@H](O)[C@H](NC(=O)C(\C)=C\C3=CC=C(O[C@@H]4O[C@@H]([C@@H](O)[C@@H]4O)C(C)=O)C(O)=C3)[C@H](O)[C@H]2O

InChI

InChIKey=YQYJSBFKSSDGFO-IIHALWDASA-N

InChI=1S/C23H29NO12/c1-8(22(32)24-13-14(27)16(29)21-20(15(13)28)33-7-34-21)5-10-3-4-12(11(26)6-10)35-23-18(31)17(30)19(36-23)9(2)25/h3-6,13-21,23,26-31H,7H2,1-2H3,(H,24,32)/b8-5+/t13-,14+,15-,16-,17+,18+,19-,20+,21-,23-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C23H29NO12
Molecular Weight	511.4759
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	10 / 10
E/Z Centers	1
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6156832 | https://www.ncbi.nlm.nih.gov/pubmed/12821448

Hygromycin A, an antibiotic produced by Streptomyces hiygroscopicus, is active against gram-positive bacteria including mycobacteria and actinomycetes, as well as against endomoeba, leptospira and pleuro- pneumonia-like organisms. Hygromycin A binds strongly to bacterial ribosomes and inhibits the ribosomal peptidyl transferase activity. The antibiotic binds to the ribosome in a distinct but overlapping manner with other antibiotics and offers a different template for generation of new agents effective against multidrug-resistant pathogens.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Bacterial 70S ribosome 179 Target ID: CHEMBL2363135 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6156832 \| https://www.ncbi.nlm.nih.gov/pubmed/26464437	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Dysentery, swine 1 Sources: https://www.google.com/patents/EP0243717A1	Curative		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Hygromycin A, a novel inhibitor of ribosomal peptidyltransferase.	1980 Jun	6156832
Structure-activity relationships of hygromycin A and its analogs: protein synthesis inhibition activity in a cell free system.	1997 Jun	9268009
Biosynthetic origin of hygromycin A.	2003 Jul	12821448
Crystallographic characterization of the ribosomal binding site and molecular mechanism of action of Hygromycin A.	2015 Nov 16	26464437

Patents

Sample Use Guides

In Vivo Use Guide

hygromycin A was confirmed to have a curative effect on swine dysentery even at low doses of 1 g/ton

Route of Administration: Oral

In Vitro Use Guide

Anti- S. hyodysenteriae activity of hygromycin A (MIC) is 0.78 ug/ml

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:02:07 GMT 2023` Edited by `admin` on `Fri Dec 15 15:02:07 GMT 2023`
Record UNII	3YJY415DDI
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

HYGROMYCIN

Common Name

English

HOMOMYCIN

Common Name

English

HYGROMYCIN [MI]

Common Name

English

ST-4331

Code

English

5-DEOXY-5-(((2E)-3-(4-((6-DEOXY-.BETA.-D-ARABINO-HEXOFURANOS-5-ULOS-1-YL)OXY)-3-HYDROXYPHENYL)-2-METHYL-1-OXO-2-PROPEN-1-YL)AMINO)-1,2-O-METHYLENE-D-NEO-INOSITOL

Common Name

English

HYGROMYCIN A

Common Name

English

Code System Code Type Description

WIKIPEDIA

Totomycin