Coumermycin A1
Clinical data
Other namesCoumamycin
ATC code
  • none
Identifiers
  • 3-methyl-1H-pyrrole-2,4-diyl)bis[carbonylimino(4-hydroxy-8-methyl-2-oxo-2H-chromene-3,7-diyl)oxy(2R,3R,4S,5R)-3-hydroxy-5-methoxy-6,6-dimethyltetrahydro-2H-pyran-2,4-diyl] bis(5-methyl-1H-pyrrole-2-carboxylate
CAS Number
PubChem CID
ChemSpider
UNII
ChEBI
ChEMBL
ECHA InfoCard100.164.703
Chemical and physical data
FormulaC55H59N5O20
Molar mass1110.092 g·mol−1
3D model (JSmol)
  • CO[C@@H]1[C@H](OC(=O)c2ccc(C)[nH]2)[C@@H](O)[C@H](Oc2ccc3c(O)c(NC(=O)c4c[nH]c(C(=O)Nc5c(=O)oc6c(C)c(ccc6c5O)O[C@@H]5OC(C)(C)[C@H](OC)[C@H](OC(=O)c6ccc(C)[nH]6)[C@H]5O)c4C)c(=O)oc3c2C)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 ☒N
  • Key:WTIJXIZOODAMJT-DHFGXMAYSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

Coumermycin A1 is an aminocoumarin.[1][2] Its main target is the ATPase site of the DNA gyrase GyrB subunit.[3]

See also

References

  1. ↑ Heide L (2009). "Genetic engineering of antibiotic biosynthesis for the generation of new aminocoumarins". Biotechnology Advances. 27 (6): 1006–1014. doi:10.1016/j.biotechadv.2009.05.017. PMID 19463934.
  2. ↑ Heide L, Gust B, Anderle C, Li SM (2008). "Combinatorial biosynthesis, metabolic engineering and mutasynthesis for the generation of new aminocoumarin antibiotics". Current Topics in Medicinal Chemistry. 8 (8): 667–79. doi:10.2174/156802608784221505. PMID 18473891.
  3. ↑ Vanden Broeck A, McEwen AG, Chebaro Y, Potier N, Lamour V (April 2019). "Structural Basis for DNA Gyrase Interaction with Coumermycin A1". Journal of Medicinal Chemistry. 62 (8): 4225–4231. doi:10.1021/acs.jmedchem.8b01928. PMID 30920824.
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