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Merck
CN

C9270

Sigma-Aldrich

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
Beilstein:
470805
MDL number:
MFCD00057312
UNSPSC Code:
51102829
PubChem Substance ID:
329775201
NACRES:
NA.85

Key Documents

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form

powder

solubility

DMSO: 50 mg/mL

antibiotic activity spectrum

Gram-negative bacteria
Gram-positive bacteria

Mode of action

DNA synthesis | interferes
enzyme | inhibits

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

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

InChI key

WTIJXIZOODAMJT-DHFGXMAYSA-N

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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

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

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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H Shawn Je et al.
Molecular brain, 4, 1-1 (2011-01-08)
Neurotrophins elicit both acute and long-term modulation of synaptic transmission and plasticity. Previously, we demonstrated that the long-term synaptic modulation requires the endocytosis of neurotrophin-receptor complex, the activation of PI3K and Akt, and mTOR mediated protein synthesis. However, it is
Andreas I Papadakis et al.
Genesis (New York, N.Y. : 2000), 49(9), 743-749 (2011-03-26)
Phosphorylation of the alpha (α) subunit of the eukaryotic initiation factor 2 (eIF2) at serine 51 is an important mechanism of translational control in response to various forms of environmental stress. In metazoans, eIF2α phosphorylation is mediated by four kinases
Manuel Wolpert et al.
Chembiochem : a European journal of chemical biology, 9(4), 603-612 (2008-02-22)
Many secondary metabolites of clinical importance have been isolated from different Streptomyces species. As most of the natural producers remain difficult to handle genetically, heterologous expression of an entire biosynthetic gene cluster in a well characterised host allows improved possibilities
Michelle Pacholec et al.
Biochemistry, 44(45), 14969-14976 (2005-11-09)
During the biosynthesis of the streptomycete aminocoumarin antibiotics novobiocin and the dimeric coumermycin A(1), the bicyclic coumarin scaffold is C-methylated adjacent to the phenolic oxygen. The SAM-dependent C-methyltransferases NovO and CouO have been heterologously expressed and purified from Escherichia coli
Carl J Balibar et al.
Chemistry & biology, 14(6), 679-690 (2007-06-23)
The last stages of assembly of the aminocoumarin antibiotics, clorobiocin and coumermycin A(1), which target the GyrB subunits of bacterial DNA gyrase, involve enzymatic transfer of the pyrrolyl-2-carbonyl acyl group from a carrier protein (CloN1/CouN1) to the 3'-OH of the
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