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CAS 4434-05-3

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Coumermycin A1

Description:
Coumermycin A1 is a naturally occurring antibiotic that belongs to the class of compounds known as coumarins. It is produced by certain strains of the bacterium *Streptomyces* and exhibits significant antibacterial activity, particularly against Gram-positive bacteria. The compound is characterized by its complex structure, which includes a coumarin core and various functional groups that contribute to its biological activity. Coumermycin A1 functions primarily by inhibiting bacterial DNA gyrase, an essential enzyme involved in DNA replication and transcription, thereby disrupting bacterial growth and proliferation. Its mechanism of action is similar to that of other antibiotics in the fluoroquinolone class. In addition to its antibacterial properties, Coumermycin A1 has been studied for its potential applications in cancer therapy and as a tool in molecular biology research. Due to its natural origin, it is of interest for further development in pharmaceutical applications, although its clinical use may be limited by factors such as stability, solubility, and potential resistance mechanisms in target bacteria.
Formula:C55H59N5O20
InChI: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:InChIKey=WTIJXIZOODAMJT-DHFGXMAYSA-N
SMILES:OC=1C=2C(=C(C)C(O[C@H]3[C@H](O)[C@H](OC(=O)C=4NC(C)=CC4)[C@@H](OC)C(C)(C)O3)=CC2)OC(=O)C1NC(=O)C=5C(C)=C(C(NC6=C(O)C=7C(OC6=O)=C(C)C(O[C@H]8[C@H](O)[C@H](OC(=O)C=9NC(C)=CC9)[C@@H](OC)C(C)(C)O8)=CC7)=O)NC5
Synonyms:
  • (3-methyl-1H-pyrrole-2,4-diyl)bis[carbonylimino(2-hydroxy-8-methyl-4-oxo-4H-chromene-3,7-diyl)oxy(2S,3S,4R,5S)-3-hydroxy-5-methoxy-6,6-dimethyltetrahydro-2H-pyran-2,4-diyl] bis(5-methyl-1H-pyrrole-2-carboxylate) (non-preferred name)
  • (3-methyl-1H-pyrrole-2,4-diyl)bis[carbonylimino(2-hydroxy-8-methyl-4-oxo-4H-chromene-3,7-diyl)oxy-3-hydroxy-5-methoxy-6,6-dimethyltetrahydro-2H-pyran-2,4-diyl] bis(5-methyl-1H-pyrrole-2-carboxylate) (non-preferred name)
  • 1H-Pyrrole-2,4-dicarboxamide, N,N′-bis[7-[[6-deoxy-5-C-methyl-4-O-methyl-3-O-[(5-methyl-1H-pyrrol-2-yl)carbonyl]-α-<span class="text-smallcaps">L</span>-lyxo-hexopyranosyl]oxy]-4-hydroxy-8-methyl-2-oxo-2H-1-benzopyran-3-yl]-3-methyl-
  • 1H-Pyrrole-2,4-dicarboxamide, N<sup>2</sup>,N<sup>4</sup>-bis[7-[[6-deoxy-5-C-methyl-4-O-methyl-3-O-[(5-methyl-1H-pyrrol-2-yl)carbonyl]-α-<span class="text-smallcaps">L</span>-lyxo-hexopyranosyl]oxy]-4-hydroxy-8-methyl-2-oxo-2H-1-benzopyran-3-yl]-3-methyl-
  • 1H-Pyrrole-2-carboxylic acid, 5-methyl-, diester with N,N′-bis[7-[(6-deoxy-5-C-methyl-4-O-methyl-α-<span class="text-smallcaps">L</span>-lyxo-hexopyranosyl)oxy]-4-hydroxy-8-methyl-2-oxo-2H-1-benzopyran-3-yl]-3-methyl-1H-pyrrole-2,4-dicarboxamide
  • Coumamycin
  • Coumarin, 3,3′-[(3-methylpyrrole-2,4-diyl)bis(carbonylimino)]bis[7-[(5,5-di-C-methyl-4-O-methyl-α-<span class="text-smallcaps">L</span>-lyxopyranosyl)oxy]-4-hydroxy-8-methyl-, bis(5-methylpyrrole-2-carboxylate) (ester)
  • Coumermycin A<sub>1</sub>
  • N<sup>2</sup>,N<sup>4</sup>-Bis[7-[[6-deoxy-5-C-methyl-4-O-methyl-3-O-[(5-methyl-1H-pyrrol-2-yl)carbonyl]-α-<span class="text-smallcaps">L</span>-lyxo-hexopyranosyl]oxy]-4-hydroxy-8-methyl-2-oxo-2H-1-benzopyran-3-yl]-3-methyl-1H-pyrrole-2,4-dicarboxamide
  • NSC 107412
  • See more synonyms
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