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Details

Stereochemistry ABSOLUTE
Molecular Formula C44H61N2O12.Na
Molecular Weight 832.9511
Optical Activity UNSPECIFIED
Defined Stereocenters 11 / 11
E/Z Centers 7
Charge 0

SHOW SMILES / InChI
Structure of AURODOX SODIUM

SMILES

[Na+].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)[C-]2C(=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=WLVQSHSFCQUZBG-FMWOWYISSA-N
InChI=1S/C44H61N2O12.Na/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;/h10,12-23,25,28-29,31-32,35-40,49-52,55H,11,24H2,1-9H3,(H,45,53);/q-1;+1/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 C44H61N2O12
Molecular Weight 809.9613
Charge -1
Count
Stereochemistry EPIMERIC
Additional Stereochemistry No
Defined Stereocenters 11 / 12
E/Z Centers 7
Optical Activity UNSPECIFIED

Molecular Formula Na
Molecular Weight 22.98976928
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
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

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P60339
Gene ID: 3168327.0
Gene Symbol: tufB
Target Organism: Thermus thermophilus (strain HB8 / ATCC 27634 / DSM 579)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
A small-molecule inhibitor of the bacterial type III secretion system protects against in vivo infection with Citrobacter rodentium.
2011-02
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
Patents

Sample Use Guides

oral administration of aurodox, 25 or 100 mg/kg
Route of Administration: Oral
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 Wed Apr 02 11:35:28 GMT 2025
Edited
by admin
on Wed Apr 02 11:35:28 GMT 2025
Record UNII
RQ94AW79K0
Record Status Validated (UNII)
Record Version
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Name Type Language
AURODOX SODIUM
Common Name English
1-METHYLMOCIMYCIN SODIUM SALT
Preferred Name English
AURODOX SODIUM SALT [MI]
Common Name English
Code System Code Type Description
MERCK INDEX
m2143
Created by admin on Wed Apr 02 11:35:28 GMT 2025 , Edited by admin on Wed Apr 02 11:35:28 GMT 2025
PRIMARY Merck Index
PUBCHEM
73425462
Created by admin on Wed Apr 02 11:35:28 GMT 2025 , Edited by admin on Wed Apr 02 11:35:28 GMT 2025
PRIMARY
FDA UNII
RQ94AW79K0
Created by admin on Wed Apr 02 11:35:28 GMT 2025 , Edited by admin on Wed Apr 02 11:35:28 GMT 2025
PRIMARY
CAS
74219-54-8
Created by admin on Wed Apr 02 11:35:28 GMT 2025 , Edited by admin on Wed Apr 02 11:35:28 GMT 2025
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
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ACTIVE MOIETY