MADURAMICIN

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 Search

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

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

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	24 / 24
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/362738 | https://www.drugs.com/vet/cygro-1-premix-can.html | https://www.ncbi.nlm.nih.gov/pubmed/29241734 | https://www.ncbi.nlm.nih.gov/pubmed/30511398

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 Target	Pharmacology	Condition	Potency
Serine/threonine protein phosphatase 2A, catalytic subunit, alpha isoform 11 Target ID: CHEMBL4703 Sources: https://www.ncbi.nlm.nih.gov/pubmed/29241734	Activator 1430
Phosphatidylinositol 3,4,5-trisphosphate 3-phosphatase and dual-specificity protein phosphatase PTEN 2 Target ID: P60484 Gene ID: 5728.0 Gene Symbol: PTEN Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/30511398	Activator 1430

Substance Class	Chemical Created by `admin` on `Fri Dec 15 18:48:51 GMT 2023` Edited by `admin` on `Fri Dec 15 18:48:51 GMT 2023`
Record UNII	5U912U22T2
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

MADURAMICIN

Official Name

English

MADURAMICIN [MART.]

Common Name

English

MADURAMICIN AMMONIUM

Common Name

English

MADURAMICIN [USAN]

Common Name

English

CYGRO

Brand Name

English

CL 273,703

Code

English

PRINICIN AMMONIUM

Common Name

English

MADURAMICIN [GREEN BOOK]

Common Name

English

maduramicin [INN]

Common Name

English

MADURAMICIN [MI]

Common Name

English

LONOMYCIN A, 23,27-DIDEMETHOXY-2,6,22-TRIDEMETHYL-11-O-DEMETHYL-22-((2,6-DIDEOXY-3,4-DI-O-METHYL-.BETA.-L-ARABINO-HEXOPYRANOSYL)OXY)-6-METHOXY-, MONOAMMONIUM SALT, (3R,4S,5S,6R,7S,22S)-

Common Name

English

MADURAMYCIN AMMONIUM

Common Name

English

CL-273703

Code

English

Classification Tree Code System Code

CFR

21 CFR 558.340