Compound ID | 914

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Nocathiacin I

Synonym(s): BMS-249524  |  MJ347-81F4 A

Class: Antimicrobial peptide

Agent Type: Natural product; Direct acting;
Spectrum of activity: Gram-positive & Antimycobacterial
Mechanism of action: Protein synthesis inhibitor. Binds to the bacterial 50S ribosomal subunit
Target Pathogen: Active against Streptococcus strains, Enterococcus faecium, Staphylococcus aureus strains including methicillin resistant isolates, Mycobacterium tuberculosis, and Mycobacterium avium
Description: Ueda Y, Pucci MJ, Barrett JF, et al. In vitro antibacterial activity, mechanism of action, and resistance development of nocathiacins, new class of thiazolyl peptide antibiotics. 43rd-ICAAC 2003;260
Institute where first reported: Bristol-Myers Squibb, UK
Year first mentioned: 2003
Development status: Experimental
Reason dropped: Poor water solubility
Chemical structure(s):
Click here for structure editor
Molecular weight: 1437.54
Iso. SMILES: C[C@H]1[C@H]([C@@](C[C@@H](O1)O[C@H]2[C@@H]3[C@H]4C5=NC(=CS5)C(=O)N[C@@H](COC(=O)C6=C(CO3)C7=C(COC2=O)C=CC=C7N6O)C8=NC(=CS8)C9=NC(=C(C=C9C%10=NC(=CS%10)C(=O)N[C@H](C(=O)N/C(=C(\C)/OC)/C%11=NC(=CS%11)C(=O)N4)[C@@H](C)O)O)C%12=NC(=CS%12)C(=O)NC(=C)C(=O)N)(C)O)N(C)C
InChI Key: FFLJEMWVYVKPDW-UMNFMQIXSA-N
Can. SMILES: C=C(C(=O)N)NC(=O)C1=CSC(=N1)C2=C(C=C3C(=N2)C4=CSC(=N4)[C@@H]5COC(=O)C6=C7CO[C@@H]([C@@H](C8=NC(=CS8)C(=O)N5)NC(=O)C9=CSC(=N9)/C(=C(/C)\OC)/NC(=O)[C@H]([C@@H](C)O)NC(=O)C%10=CSC3=N%10)[C@@H](C(=O)OCC%11=CC=CC(=C%117)N6O)O[C@H]%12C[C@@](C)([C@@H]([C@H](C)O%12)N(C)C)O)O
InChI: InChI=1S/C61H60N14O18S5/c1-22(48(62)78)63-49(79)31-19-97-57(68-31)42-36(77)12-27-41(70-42)30-17-95-55(65-30)29-16-91-59(84)44-28-15-89-45(46(93-37-13-61(5,86)47(74(6)7)25(4)92-37)60(85)90-14-26-10-9-11-35(38(26)28)75(44)87)43(58-69-32(20-98-58)50(80)64-29)73-52(82)34-21-96-56(67-34)40(24(3)88-8)72-53(83)39(23(2)76)71-51(81)33-18-94-54(27)66-33/h9-12,17-21,23,25,29,37,39,43,45-47,76-77,86-87H,1,13-16H2,2-8H3,(H2,62,78)(H,63,79)(H,64,80)(H,71,81)(H,72,83)(H,73,82)/b40-24+/t23-,25+,29+,37+,39+,43+,45+,46+,47-,61+/m1/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/16142519
Citations:
  • https://doi.org/10.7164/antibiotics.56.226
  • https://journals.asm.org/doi/10.1128/aac.48.10.3697-3701.2004

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