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Details

Stereochemistry ABSOLUTE
Molecular Formula C55H59N5O20
Molecular Weight 1110.0785
Optical Activity UNSPECIFIED
Defined Stereocenters 8 / 8
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of COUMERMYCIN

SMILES

CO[C@@H]1[C@@H](OC(=O)C2=CC=C(C)N2)[C@@H](O)[C@H](OC3=C(C)C4=C(C=C3)C(O)=C(NC(=O)C5=CNC(C(=O)NC6=C(O)C7=C(OC6=O)C(C)=C(O[C@@H]8OC(C)(C)[C@H](OC)[C@@H](OC(=O)C9=CC=C(C)N9)[C@H]8O)C=C7)=C5C)C(=O)O4)OC1(C)C

InChI

InChIKey=WTIJXIZOODAMJT-DHFGXMAYSA-N
InChI=1S/C55H59N5O20/c1-21-12-16-29(57-21)48(67)77-42-38(63)52(79-54(6,7)44(42)71-10)73-31-18-14-26-36(61)34(50(69)75-40(26)24(31)4)59-46(65)28-20-56-33(23(28)3)47(66)60-35-37(62)27-15-19-32(25(5)41(27)76-51(35)70)74-53-39(64)43(45(72-11)55(8,9)80-53)78-49(68)30-17-13-22(2)58-30/h12-20,38-39,42-45,52-53,56-58,61-64H,1-11H3,(H,59,65)(H,60,66)/t38-,39-,42+,43+,44-,45-,52-,53-/m1/s1

HIDE SMILES / InChI

Molecular Formula C55H59N5O20
Molecular Weight 1110.0785
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry
Defined Stereocenters 8 / 8
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Coumermycin is from the aminocoumarin class of antibiotic compounds which acts by inhibiting DNA gyrase. Coumermycin is effective against gram-positive bacteria, but not gram-negative bacteria. Coumermycin its derivatives have been studied since the 1950's as potential antibiotic. However, it has seen little to no clinical development because of its low water solubility, toxicity profile, and ineffectiveness against gram-negative bacteria.

CNS Activity

Target Info

Target Info

Primary TargetPharmacologyConditionPotency
Condition Info

Condition Info

ConditionModalityTargetsHighest PhaseProduct
Primary
PMID

PMID

TitleDatePMID
Novobiocin and coumermycin inhibit DNA supercoiling catalyzed by DNA gyrase.
1976 Dec
Efficacy of coumermycin, ofloxacin and vancomycin against methicillin-resistant Staphylococcus aureus in vitro and in experimental infections of mice.
1988 Mar
Combinatorial biosynthesis, metabolic engineering and mutasynthesis for the generation of new aminocoumarin antibiotics.
2008
A New-Class Antibacterial-Almost. Lessons in Drug Discovery and Development: A Critical Analysis of More than 50 Years of Effort toward ATPase Inhibitors of DNA Gyrase and Topoisomerase IV.
2015 Jan 9
Patent

Sample Use Guides

In Vivo Use Guide
Lethal septicemia was induced in mice by intraperitoneal administration of Methicillin-Resistant Staphylococcus. The infection was successfully treated in 50% of the animals (ED50) following a dose of 0.9 micro-g/g body weight. This was significantly better than ofloxacin and vancomycin.
Route of Administration: subcutaneous
In Vitro Use Guide
The antibiotic ability of coumermycin was evaluated against 232 bacterial strains. Minimal inhibitory concentrations (MIC) were determined in trypticase soy broth using twofold serial dilutions. The last tube in a series to show no visible growth after 18 hours at 37 deg-C was considered the MIC. Strain specific MIC's were reported between 0.002 micro-g/L and 100 micro-g/L.
Substance Class Chemical
Created
by admin
on Tue Mar 06 17:15:51 UTC 2018
Edited
by admin
on Tue Mar 06 17:15:51 UTC 2018
Record UNII
PCH9QZ1IIH
Record Status Validated (UNII)
Record Version
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Name Type Language
COUMERMYCIN
USAN  
USAN  
Official Name English
COUMAMYCIN
INN  
INN  
Official Name English
1H-PYRROLE-2,4-DICARBOXAMIDE, N2,N4-BIS(7-((6-DEOXY-5-C-METHYL-4-O-METHYL-3-O-((5-METHYL-1H-PYRROL-2-YL)CARBONYL)-.ALPHA.-L-LYXO-HEXOPYRANOSYL)OXY)-4-HYDROXY-8-METHYL-2-OXO-2H-1-BENZOPYRAN-3-YL)-3-METHYL-
Common Name English
5-METHYLPYYROLE-2-CARBOXYLIC ACID, DIESTER WITH 3,3'-((3-METHYLPYRROLE-2,4-DIYL)BIS(CARBONYLIMINO))BIS(4-HYDROXY-8-METHYL-7-((TETRAHYDRO-3,4-DIHYDROXY-5-METHOXY-6,6-DIMETHYLPYRAN-2-YL)OXY)COUMARIN)
Common Name English
NSC-107412
Code English
COUMAMYCIN [INN]
Common Name English
NOTOMYCIN A1
Common Name English
COUMERMYCIN [USAN]
Common Name English
Code System Code Type Description
PUBCHEM
54675768
Created by admin on Tue Mar 06 17:15:51 UTC 2018 , Edited by admin on Tue Mar 06 17:15:51 UTC 2018
PRIMARY SWITZERF
EVMPD
SUB06814MIG
Created by admin on Tue Mar 06 17:15:51 UTC 2018 , Edited by admin on Tue Mar 06 17:15:51 UTC 2018
PRIMARY
NCI_THESAURUS
C81447
Created by admin on Tue Mar 06 17:15:51 UTC 2018 , Edited by admin on Tue Mar 06 17:15:51 UTC 2018
PRIMARY
CAS
4434-05-3
Created by admin on Tue Mar 06 17:15:51 UTC 2018 , Edited by admin on Tue Mar 06 17:15:51 UTC 2018
PRIMARY
MESH
C004628
Created by admin on Tue Mar 06 17:15:51 UTC 2018 , Edited by admin on Tue Mar 06 17:15:51 UTC 2018
PRIMARY
ChEMBL
CHEMBL1908352
Created by admin on Tue Mar 06 17:15:51 UTC 2018 , Edited by admin on Tue Mar 06 17:15:51 UTC 2018
PRIMARY
INN
1948
Created by admin on Tue Mar 06 17:15:51 UTC 2018 , Edited by admin on Tue Mar 06 17:15:51 UTC 2018
PRIMARY
Related Record Type Details
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