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Merck
CN

C9270

Coumermycin A1

Synonym(s):

Notomycin A1

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About This Item

Empirical Formula (Hill Notation):
C55H59N5O20
CAS Number:
4434-05-3
Molecular Weight:
1110.08
UNSPSC Code:
51102829
NACRES:
NA.85
PubChem Substance ID:
329775201
MDL number:
MFCD00057312
Beilstein/REAXYS Number:
470805

Key Documents

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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

SMILES string

CO[C@@H]1[C@@H](OC(=O)c2ccc(C)[nH]2)[C@@H](O)[C@H](Oc3ccc4C(O)=C(NC(=O)c5c[nH]c(C(=O)NC6=C(O)c7ccc(O[C@@H]8OC(C)(C)[C@H](OC)[C@@H](OC(=O)c9ccc(C)[nH]9)[C@H]8O)c(C)c7OC6=O)c5C)C(=O)Oc4c3C)OC1(C)C

InChI key

WTIJXIZOODAMJT-DHFGXMAYSA-N

form

powder

solubility

DMSO: 50 mg/mL

antibiotic activity spectrum

Gram-negative bacteria, Gram-positive bacteria

mode of action

DNA synthesis | interferes, enzyme | inhibits

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General description

Chemical structure: coumarin-glycoside

Application

Coumermycin A1 is an aminocoumarin antibiotic used to study processes such as DNA replication, transcription, and recombination that involve DNA topoisomerase II activity. It has been used to treat Staphylococcus aureus endocarditis in the rat model and to study the effect of coumermycin A1 on the expression of 67 fusions in Salmonella typhimurium. .

Biochem/physiol Actions

Coumermycin A1 inhibits DNA Gyrase which thereby inhibits cell division in bacteria.

Other Notes

Keep container tightly closed in a dry and well-ventilated place. Keep in a dry place.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

涉药品监管产品
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Certificates of Analysis (COA)

Lot/Batch Number
SLBZ7154
SLBT5569
SLBN6743V
SLBC8762V
061M1846V

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Pieter C Dorrestein et al.
Biochemistry, 45(6), 1537-1546 (2006-02-08)
For screening a pool of potential substrates that load carrier domains found in nonribosomal peptide synthetases, large molecule mass spectrometry is shown to be a new, unbiased assay. Combining the high resolving power of Fourier transform mass spectrometry with the
Lutz Heide
Methods in enzymology, 459, 437-455 (2009-04-14)
The aminocoumarin antibiotics novobiocin, clorobiocin and coumermycin A(1) are formed by different Streptomyces strains and are potent inhibitors of bacterial gyrase. Their biosynthetic gene clusters have been analyzed in detail by genetic and biochemical investigations. Heterologous expression of these gene
C M Perronne et al.
Antimicrobial agents and chemotherapy, 31(4), 539-543 (1987-04-01)
The efficacy of a 5-day treatment with coumermycin A1 (hereafter referred to as coumermycin) (at three dosage regimens), with ciprofloxacin, or with coumermycin plus ciprofloxacin was tested in experimental aortic valve endocarditis induced in rats by a strain of methicillin-susceptible
Ryan C Chai et al.
Molecular oncology, 11(5), 567-583 (2017-03-18)
Heat shock protein 90 (HSP90) regulates multiple signalling pathways critical for tumour growth. As such, HSP90 inhibitors have been shown to act as effective anticancer agents in preclinical studies but, for a number of reasons, the same effect has not
S B Jovanovich et al.
Journal of bacteriology, 169(10), 4431-4435 (1987-10-01)
We have estimated the extent to which relaxation of supercoiling by the DNA gyrase inhibitor coumermycin A1 affects gene expression in vivo in Salmonella typhimurium. We isolated a set of Mu d1-8 Lac+ operon fusions to random promoters and measured
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