AURODOX

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C44H62N2O12
Molecular Weight	810.9693
Optical Activity	UNSPECIFIED
Defined Stereocenters	11 / 11
E/Z Centers	7
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC[C@H](C(=O)NC\C=C\C=C(/C)[C@@H](OC)[C@@H](C)[C@@H]1O[C@H](\C=C\C=C\C=C(/C)C(=O)C2=C(O)C=CN(C)C2=O)[C@H](O)[C@@H]1O)[C@@]3(O)O[C@@H](\C=C\C=C/C)C(C)(C)[C@@H](O)[C@H]3O

InChI

InChIKey=NTAHMPNXQOYXSX-WKSONYIQSA-N

InChI=1S/C44H62N2O12/c1-10-12-14-22-32-43(6,7)39(51)40(52)44(55,58-32)29(11-2)41(53)45-24-18-17-20-27(4)37(56-9)28(5)38-36(50)35(49)31(57-38)21-16-13-15-19-26(3)34(48)33-30(47)23-25-46(8)42(33)54/h10,12-23,25,28-29,31-32,35-40,47,49-52,55H,11,24H2,1-9H3,(H,45,53)/b12-10-,15-13+,18-17+,21-16+,22-14+,26-19+,27-20+/t28-,29-,31-,32+,35+,36+,37-,38+,39+,40-,44-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C44H62N2O12
Molecular Weight	810.9693
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	11 / 11
E/Z Centers	7
Optical Activity	UNSPECIFIED

Description
Sources: https://www.drugbank.ca/drugs/DB04124 | https://www.ncbi.nlm.nih.gov/pubmed/11278992
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/21139624 https://www.ncbi.nlm.nih.gov/pubmed/11278992

Aurodox is an antibiotic obtained from a streptomyces variant considered as possibly effective against streptococcus pyogenes infections. It may promote growth in poultry. Aurodox inhibits protein biosynthesis by binding to elongation factor Tu (EF-Tu). Aurodox has being shown to possess the ability to inhibit the secretion of type III-secreted proteins without affecting bacterial growth.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
protein secretion by the type III secretion system 2 Target ID: GO:0030254 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21139624	Inhibitor 8504
Elongation factor Tu-B 2 Target ID: P60339 Gene ID: 3168327.0 Gene Symbol: tufB Target Organism: Thermus thermophilus (strain HB8 / ATCC 27634 / DSM 579) Sources: https://www.ncbi.nlm.nih.gov/pubmed/11278992 \| https://www.ncbi.nlm.nih.gov/pubmed/12370016 \| https://www.ncbi.nlm.nih.gov/pubmed/6119303	Binding Agent 1076

Conditions

Condition	Modality	Targets	Highest Phase	Product
Gram-negative bacterial infections 4 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21139624 https://www.ncbi.nlm.nih.gov/pubmed/468738	Curative		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
A small-molecule inhibitor of the bacterial type III secretion system protects against in vivo infection with Citrobacter rodentium.	2011-02	21139624
Conformational change of elongation factor Tu (EF-Tu) induced by antibiotic binding. Crystal structure of the complex between EF-Tu.GDP and aurodox.	2001-05-18	11278992

Patents

Sample Use Guides

In Vivo Use Guide

oral administration of aurodox, 25 or 100 mg/kg

Route of Administration: Oral

In Vitro Use Guide

Aurodox strongly inhibited T3SS-mediated hemolysis with an IC(50) value of 1.5 ug/ml without affecting bacterial growth in liquid media.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 22:39:58 GMT 2025` Edited by `admin` on `Mon Mar 31 22:39:58 GMT 2025`
Record UNII	PGP5RZH64G
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

AURODOX

Common Name

English

NSC-233989

Preferred Name

English

GOLDINODOX

Common Name

English

GOLDINOMYCIN

Common Name

English

1-METHYLMOCIMYCIN

Common Name

English

AURODOX [MI]

Common Name

English

X-5108

Code

English

ANTIBIOTIC X-5108

Common Name

English

Code System Code Type Description

PUBCHEM

135509117