Compound ID | 991

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Coumermycin A1

Class: Aminocoumarin

Agent Type: Natural product; Direct acting;
Spectrum of activity: Gram-positive
Mechanism of action: DNA synthesis inhibitor. Bacterial topoisomerase inhibitor
Target Pathogen: Active against Staphylococcus aureus
Combined with other compounds: Tested in combination with ciprofloxacin for the treatment of S.aures infections, no synergistic effect observed.
Propensity to select resistant mutants: Coumermycin resistant mutants could be selected in vitro in 15 S.aureus strains tested in
Description: Grunberg, E., R. Cleeland, and E. Titsworth. "Further observations on chemotherapeutic activity of coumermycin A1. I. Activity against Neisseria meningitidis type A and meningopneumonitis." Antimicrobial agents and chemotherapy 6 (1966): 397.
Year first mentioned: 1966
Highest development stage: Preclinical
Development status: Experimental
Reason dropped: Weak bactericidal activity at high concentration despite reasonable bacteriostatic activity at lower concentrations; poorly absorbed from gastrointestinal tract
Chemical structure(s):
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Molecular weight: 1110.08
Iso. SMILES: CC1=CC=C(N1)C(=O)O[C@H]2[C@H]([C@@H](OC([C@@H]2OC)(C)C)OC3=C(C4=C(C=C3)C(=C(C(=O)O4)NC(=O)C5=CNC(=C5C)C(=O)NC6=C(C7=C(C(=C(C=C7)O[C@H]8[C@@H]([C@@H]([C@H](C(O8)(C)C)OC)OC(=O)C9=CC=C(N9)C)O)C)OC6=O)O)O)C)O
InChI Key: WTIJXIZOODAMJT-DHFGXMAYSA-N
Can. SMILES: CC1=CC=C(C(=O)O[C@H]2[C@H]([C@H](OC3=C(C)C4=C(C=C3)C(=C(C(=O)O4)NC(=O)C5=CNC(=C5C)C(=O)NC6=C(C7=C(C(=C(C=C7)O[C@H]8[C@@H]([C@@H]([C@H](C(C)(C)O8)OC)OC(=O)C9=CC=C(C)N9)O)C)OC6=O)O)O)OC(C)(C)[C@@H]2OC)O)N1
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
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/54675768
Guide to Pharmacology: coumamycin
Citations:
  • https://doi.org/10.1128/aac.6.4.397
  • https://doi.org/10.1021/acs.jmedchem.8b01928

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