Compound ID | 2646

Update compound information

Nigericin

Synonym(s): Azalomycin M  |  helixin C

Class: Natural product antibiotic

Agent Type: Natural product; Small molecule; Direct acting;
Spectrum of activity: Gram-positive
Mechanism of action: Membrane-active agent. Disrupts integrity of cytoplasmic membrane
Target Pathogen: Active against multi-drug resistant Staphylococcus aureus, Staphylococcus epidermidis, Enterococcus faecium, and Streptococcus pneumoniae
Description: Natural product from Streptomyces hygroscopicus; analogues with reduced toxicity to eukaryotic cells reported elsewhere; shows synergism with tigecycline, oxacillin, and moxifloxacin; reduces Staphylococcus aureus USA300 load to up to 10^3-fold in mouse infection; a polyether ionophore
Year first mentioned: 1951
Development status: Experimental
Chemical structure(s):
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Molecular weight: 724.96
Iso. SMILES: C[C@H]1CC[C@@H](O[C@H]1[C@@H](C)C(=O)O)C[C@@H]2C[C@H]([C@H]([C@@]3(O2)[C@@H](C[C@@](O3)(C)[C@H]4CC[C@@](O4)(C)[C@H]5[C@H](C[C@@H](O5)[C@@H]6[C@H](C[C@H]([C@@](O6)(CO)O)C)C)C)C)C)OC
InChI Key: DANUORFCFTYTSZ-SJSJOXFOSA-N
Can. SMILES: C[C@H]1CC[C@H](C[C@@H]2C[C@H]([C@@H](C)[C@]3([C@H](C)C[C@@](C)([C@H]4CC[C@@](C)([C@H]5[C@@H](C)C[C@H]([C@@H]6[C@@H](C)C[C@@H](C)[C@@](CO)(O)O6)O5)O4)O3)O2)OC)O[C@H]1[C@@H](C)C(=O)O
InChI: InChI=1S/C40H68O11/c1-21-11-12-28(46-33(21)26(6)36(42)43)17-29-18-30(45-10)27(7)40(48-29)25(5)19-38(9,51-40)32-13-14-37(8,49-32)35-23(3)16-31(47-35)34-22(2)15-24(4)39(44,20-41)50-34/h21-35,41,44H,11-20H2,1-10H3,(H,42,43)/t21-,22-,23-,24+,25+,26+,27+,28+,29+,30+,31+,32+,33+,34-,35+,37-,38-,39-,40+/m0/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/34230
Citations:
  • https://pubs.rsc.org/en/content/articlelanding/2020/ra/d0ra05137c
  • https://www.frontiersin.org/articles/10.3389/fcimb.2022.1055929/full

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