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Details

Stereochemistry ABSOLUTE
Molecular Formula C47H79O17.H4N
Molecular Weight 934.1584
Optical Activity UNSPECIFIED
Defined Stereocenters 24 / 24
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MADURAMICIN

SMILES

[NH4+].[H][C@@]1(C[C@H](O[C@]2([H])C[C@H](OC)[C@@H](OC)[C@H](C)O2)[C@@]([H])(O1)[C@]3(C)CC[C@@]([H])(O3)[C@]4(C)CC[C@]5(C[C@H](O)[C@@H](C)[C@]([H])(O5)[C@@H](C)[C@]6([H])O[C@](O)(CC([O-])=O)[C@@H](C)[C@H](OC)[C@H]6OC)O4)[C@@]7([H])O[C@](C)(O)[C@H](C)C[C@@H]7C

InChI

InChIKey=WQGJEAMPBSZCIF-HKSLRPGUSA-N
InChI=1S/C47H80O17.H3N/c1-23-18-24(2)45(9,51)61-36(23)31-19-32(58-35-20-30(53-10)40(55-12)28(6)57-35)42(59-31)44(8)15-14-33(60-44)43(7)16-17-46(64-43)21-29(48)25(3)37(62-46)26(4)38-41(56-13)39(54-11)27(5)47(52,63-38)22-34(49)50;/h23-33,35-42,48,51-52H,14-22H2,1-13H3,(H,49,50);1H3/t23-,24+,25+,26+,27-,28-,29-,30-,31+,32-,33+,35+,36-,37-,38-,39-,40-,41-,42+,43-,44-,45-,46+,47+;/m0./s1

HIDE SMILES / InChI

Molecular Formula H3N
Molecular Weight 17.0305
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C47H80O17
Molecular Weight 917.1279
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 24 / 24
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Maduramicin is antibiotic isolated from actinobacteria Actinomadura rubra. Maduramicin is used in veterinary as an aid in the prevention of coccidiosis in broiler chickens and turkeys. The compound is reported to be toxic to animals and humans if improperly used or by accident, resulting in heart failure, skeletal muscle degeneration, and even death. Studies have shown that toxicity is due to activation of protein phosphatase 2A, and the manipulation of the ROS-PTEN-Akt-Erk1/2 pathway may be a potential approach to prevent maduramicin -induced cardiotoxicity.

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
Substance Class Chemical
Record UNII
5U912U22T2
Record Status Validated (UNII)
Record Version