Compound ID | 604

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Caprazamycin B

Class: Natural product antibiotic

Agent Type: Natural product; Direct acting;
Spectrum of activity: Antimycobacterial
Mechanism of action: Mycolic acid synthesis inhibitor. MraY inhibitor; interferes with cell-wall synthesis by inhibiting transfer of the peptidoglycan precursor moiety (MurNAc-pentapeptide) to the membrane lipid carrier, undecaprenyl phosphate
Target Pathogen: Active against Mycobacterium tuberculosis
Description: Natural product from Streptomyces sp.
Institute where first reported: Meiji Seika Kaisha, Japan
Year first mentioned: 2002
Development status: Experimental
Reason dropped: IV only; modest anti-tubercular activity, low intracellular activity. Not great in vivo activity. Many analogues made. Permeability and efflux problems
Chemical structure(s):
Click here for structure editor
Molecular weight: 1146.28
Iso. SMILES: CC1C(C(C(C(O1)OC(=O)CC(C)CC(=O)OC(CCCCCCCCCCC(C)C)CC(=O)OC2CN(C(C(=O)N(C2C(=O)O)C)C(C3C(C(C(O3)N4C=CC(=O)NC4=O)O)O)OC5C(C(C(O5)CN)O)O)C)OC)OC)OC
InChI Key: IDKBSYZJTHLMLI-UHFFFAOYSA-N
Can. SMILES: CC(C)CCCCCCCCCCC(CC(=O)OC1CN(C)C(C(C2C(C(C(N3C=CC(=O)NC3=O)O2)O)O)OC4C(C(C(CN)O4)O)O)C(=O)N(C)C1C(=O)O)OC(=O)CC(C)CC(=O)OC5C(C(C(C(C)O5)OC)OC)OC
InChI: InChI=1S/C53H87N5O22/c1-27(2)18-16-14-12-10-11-13-15-17-19-30(75-34(60)22-28(3)23-35(61)78-52-47(73-9)46(72-8)43(71-7)29(4)74-52)24-36(62)76-32-26-56(5)38(48(67)57(6)37(32)50(68)69)44(80-51-42(66)39(63)31(25-54)77-51)45-40(64)41(65)49(79-45)58-21-20-33(59)55-53(58)70/h20-21,27-32,37-47,49,51-52,63-66H,10-19,22-26,54H2,1-9H3,(H,68,69)(H,55,59,70)
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/9854993
Guide to Pharmacology: caprazamycin B
Citations:
  • https://www.nature.com/articles/ja200541.pdf
  • https://doi.org/10.1016/j.ejmech.2019.01.071

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