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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 22.9898
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
Conformational change of elongation factor Tu (EF-Tu) induced by antibiotic binding. Crystal structure of the complex between EF-Tu.GDP and aurodox.
2001 May 18
A small-molecule inhibitor of the bacterial type III secretion system protects against in vivo infection with Citrobacter rodentium.
2011 Feb
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 Sat Dec 16 18:34:27 GMT 2023
Edited
by admin
on Sat Dec 16 18:34:27 GMT 2023
Record UNII
RQ94AW79K0
Record Status Validated (UNII)
Record Version
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Name Type Language
AURODOX SODIUM
Common Name English
AURODOX SODIUM SALT [MI]
Common Name English
1-METHYLMOCIMYCIN SODIUM SALT
Common Name English
Code System Code Type Description
MERCK INDEX
m2143
Created by admin on Sat Dec 16 18:34:27 GMT 2023 , Edited by admin on Sat Dec 16 18:34:27 GMT 2023
PRIMARY Merck Index
PUBCHEM
73425462
Created by admin on Sat Dec 16 18:34:27 GMT 2023 , Edited by admin on Sat Dec 16 18:34:27 GMT 2023
PRIMARY
FDA UNII
RQ94AW79K0
Created by admin on Sat Dec 16 18:34:27 GMT 2023 , Edited by admin on Sat Dec 16 18:34:27 GMT 2023
PRIMARY
CAS
74219-54-8
Created by admin on Sat Dec 16 18:34:27 GMT 2023 , Edited by admin on Sat Dec 16 18:34:27 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY