Compound ID | 603

Update compound information

Caprazamycin A

Class: MraY inhibitor (liponucleoside)

Details of activity: Interferes with cell-wall synthesis by inhibiting transfer of the peptidoglycan precursor moiety (MurNAc-pentapeptide) to the membrane lipid carrier, undecaprenyl phosphate. Activity against Mycobacterium tuberculosis
Institute where first reported: Meiji Seika Kaisha, Japan
Year first mentioned: 2002
Highest developmental phase: Preclinical
Development status: Inactive
Reason Dropped: IV only; modest anti-tubercular activity, low intracellular activity. Not great in vivo activity. Many analogues made. Permeability and efflux problems (2).
Chemical structure(s):
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Molecular weight: 1146.28
Iso. SMILES: CCCCCCCCCCCCC[C@@H](CC(=O)O[C@H]1CN([C@H](C(=O)N([C@@H]1C(=O)O)C)C([C@@H]2[C@H]([C@H]([C@@H](O2)N3C=CC(=O)NC3=O)O)O)O[C@H]4[C@@H]([C@@H]([C@H](O4)CN)O)O)C)OC(=O)C[C@H](C)CC(=O)O[C@H]5[C@@H]([C@@H]([C@@H]([C@H](O5)C)OC)OC)OC
InChI Key: JOXMICZHYUYJJD-AYLMBEEOSA-N
Can. SMILES: CCCCCCCCCCCCC[C@@H](CC(=O)O[C@H]1CN(C)[C@@H](C([C@@H]2[C@H]([C@H]([C@H](N3C=CC(=O)NC3=O)O2)O)O)O[C@H]4[C@@H]([C@@H]([C@@H](CN)O4)O)O)C(=O)N(C)[C@@H]1C(=O)O)OC(=O)C[C@H](C)CC(=O)O[C@H]5[C@@H]([C@@H]([C@@H]([C@@H](C)O5)OC)OC)OC
InChI: InChI=1S/C53H87N5O22/c1-9-10-11-12-13-14-15-16-17-18-19-20-30(75-34(60)23-28(2)24-35(61)78-52-47(73-8)46(72-7)43(71-6)29(3)74-52)25-36(62)76-32-27-56(4)38(48(67)57(5)37(32)50(68)69)44(80-51-42(66)39(63)31(26-54)77-51)45-40(64)41(65)49(79-45)58-22-21-33(59)55-53(58)70/h21-22,28-32,37-47,49,51-52,63-66H,9-20,23-27,54H2,1-8H3,(H,68,69)(H,55,59,70)/t28-,29+,30-,31+,32-,37-,38-,39+,40-,41+,42+,43+,44?,45-,46+,47+,49+,51-,52-/m0/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/139586657
Citations:
  • https://www.nature.com/articles/ja200541.pdf
  • https://www.ncbi.nlm.nih.gov/pubmed/21186194

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