Compound ID | 3279

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Avilamycin

Synonym(s): Surmax

Class: Orthosomycin

Spectrum of activity: Gram-positive
Details of activity: Active against Clostridium perfringens, Staphylococcus sp., coagulase-negative Staphylococcus aureus, Enterococcus faecium, and Enterococcus faecalis; protein synthesis inhibitor (inhibits binding of formylmethionyl-tRNA to 30s ribosomal subunit)
Propensity to select resistant mutants: Yes, observed in Enterococcus faecium
Description: Natural product from Streptomyces viridochromogenes; orthosomycin-type antibiotic
Year first mentioned: 1968
Development status: Experimental
Chemical structure(s):
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Molecular weight: 1404.24
Iso. SMILES: C[C@@H]1[C@H]([C@@H](C[C@@H](O1)O[C@@H]2[C@H](OC3(C[C@H]2O)O[C@@H]4[C@H](O[C@H](C[C@]4(O3)C)O[C@@H]5[C@H]([C@@H](O[C@@H]([C@@H]5OC)C)O[C@@H]6[C@H](O[C@H]([C@H]([C@H]6O)OC)OC7[C@@H]([C@H]8[C@H](CO7)O[C@@]9(O8)[C@H]1[C@H]([C@@]([C@H](O9)C)(C(=O)C)O)OCO1)OC(=O)C(C)C)COC)O)C)C)O)OC(=O)C1=C(C(=C(C(=C1OC)Cl)O)Cl)C
InChI Key: XIRGHRXBGGPPKY-OTPQUNEMSA-N
Can. SMILES: CC(C)C(=O)O[C@@H]1[C@H]2[C@H](COC1O[C@H]3[C@H]([C@H]([C@@H]([C@@H](COC)O3)O[C@H]4[C@@H]([C@H]([C@H]([C@@H](C)O4)OC)O[C@H]5C[C@]6(C)[C@@H]([C@@H](C)O5)OC7(C[C@H]([C@@H]([C@@H](C)O7)O[C@H]8C[C@H]([C@@H]([C@@H](C)O8)OC(=O)C9=C(C(=C(C(=C9C)Cl)O)Cl)OC)O)O)O6)O)O)OC)O[C@]%10([C@H]%11[C@H]([C@](C(=O)C)([C@@H](C)O%10)O)OCO%11)O2
InChI: InChI=1S/C61H88Cl2O32/c1-21(2)53(70)87-49-45-32(92-61(93-45)52-51(78-20-79-52)60(72,27(8)64)28(9)91-61)19-77-56(49)89-57-48(76-14)39(68)44(31(83-57)18-73-11)88-55-40(69)47(43(74-12)24(5)82-55)85-34-17-58(10)50(26(7)81-34)94-59(95-58)16-30(66)42(25(6)90-59)84-33-15-29(65)41(23(4)80-33)86-54(71)35-22(3)36(62)38(67)37(63)46(35)75-13/h21,23-26,28-34,39-45,47-52,55-57,65-69,72H,15-20H2,1-14H3/t23-,24-,25-,26-,28-,29-,30-,31-,32+,33+,34+,39+,40-,41-,42-,43+,44-,45-,47-,48+,49-,50-,51-,52-,55+,56?,57+,58-,59?,60+,61-/m1/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/71674
Citations:
  • https://febs.onlinelibrary.wiley.com/doi/10.1016/0014-5793%2873%2980364-3
  • https://doi.org/10.7164/antibiotics.39.877

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