Compound ID | 2111

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Sansanmycin

Class: Natural product antibiotic

Agent Type: Natural product; Small molecule; Direct acting;
Spectrum of activity: 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: Active against Mycobacterium tuberculosis
Description: Natural product produced by Streptomyces; structurally similar to pacidamycin; synthetic dihydrosansanmycin, several synthetic analogues
Year first mentioned: 2007
Development status: Experimental
Chemical structure(s):
Click here for structure editor
Molecular weight: 863.94
Iso. SMILES: CC(C(C(=O)N/C=C/1\C[C@H]([C@@H](O1)N2C=CC(=O)NC2=O)O)NC(=O)C(CCSC)NC(=O)NC(CC3=CNC4=CC=CC=C43)C(=O)O)N(C)C(=O)C(CC5=CC(=CC=C5)O)N
InChI Key: JTNZPPUDLUHMKK-OXOXDDDLSA-N
Can. SMILES: CC(C(C(=O)N/C=C/1\C[C@H]([C@H](N2C=CC(=O)NC2=O)O1)O)NC(=O)C(CCSC)NC(=O)NC(CC3=CNC4=C3C=CC=C4)C(=O)O)N(C)C(=O)C(CC5=CC=CC(=C5)O)N
InChI: InChI=1S/C40H49N9O11S/c1-21(48(2)36(55)27(41)16-22-7-6-8-24(50)15-22)33(35(54)43-20-25-18-31(51)37(60-25)49-13-11-32(52)46-40(49)59)47-34(53)29(12-14-61-3)44-39(58)45-30(38(56)57)17-23-19-42-28-10-5-4-9-26(23)28/h4-11,13,15,19-21,27,29-31,33,37,42,50-51H,12,14,16-18,41H2,1-3H3,(H,43,54)(H,47,53)(H,56,57)(H2,44,45,58)(H,46,52,59)/b25-20+/t21?,27?,29?,30?,31-,33?,37-/m1/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/57395472
Guide to Pharmacology: sansanmycin A
Citations:
  • https://pubmed.ncbi.nlm.nih.gov/34845906/
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5337940/
  • https://www.nature.com/articles/ncomms14414

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