Compound ID | 2107

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Capuramycin

Class: Natural product antibiotic

Agent Type: Natural product; Small molecule; Direct acting;
Spectrum of activity: Gram-positive & Antimycobacterial
Mechanism of action: Cell wall synthesis inhibitor. Interferes with cell-wall synthesis by inhibiting transfer of the peptidoglycan precursor moiety (MurNAc-pentapeptide) to the membrane lipid carrier, undecaprenyl phosphate; MraY inhibitor
Target Pathogen: Activity against Streptococcus pneumoniae, Mycobacterium tuberculosis and non-tuberculous Mycobacteria
Description: Natural product produced by Streptomyces; total synthesis and several analogues
Year first mentioned: 1986
Development status: Experimental
Chemical structure(s):
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Molecular weight: 569.52
Iso. SMILES: CO[C@H]1[C@H]([C@@H](O[C@@H]1[C@H](C(=O)N)O[C@@H]2[C@H]([C@H](C=C(O2)C(=O)N[C@H]3CCCCNC3=O)O)O)N4C=CC(=O)NC4=O)O
InChI Key: BISOEENGZHMDEO-RLXIHFJVSA-N
Can. SMILES: CO[C@H]1[C@H]([C@H](N2C=CC(=O)NC2=O)O[C@@H]1[C@H](C(=O)N)O[C@@H]3[C@H]([C@H](C=C(C(=O)N[C@H]4CCCCNC4=O)O3)O)O)O
InChI: InChI=1S/C23H31N5O12/c1-37-15-14(32)21(28-7-5-12(30)27-23(28)36)39-16(15)17(18(24)33)40-22-13(31)10(29)8-11(38-22)20(35)26-9-4-2-3-6-25-19(9)34/h5,7-10,13-17,21-22,29,31-32H,2-4,6H2,1H3,(H2,24,33)(H,25,34)(H,26,35)(H,27,30,36)/t9-,10-,13-,14+,15-,16-,17+,21+,22+/m0/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/5487121
Guide to Pharmacology: capuramycin
Citations:
  • https://academic.oup.com/jac/article/65/12/2590/755702
  • https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/ejoc.202100613

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