Compound ID | 2738

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Sparsomycin

Class: Natural product antibiotic

Agent Type: Natural product; Small molecule; Direct acting;
Spectrum of activity: Gram-positive & Gram-negative
Mechanism of action: Protein synthesis inhibitor. Binds to the A-site of large ribosome unit preventing peptide bond formation
Description: Natural product from Streptomyces sparsogenes; shows selective antitumor activity
Year first mentioned: 1962
Development status: Inactive
Reason dropped: Strong retinotoxicity during Phase 1 clinical trial as anticancer drug
Chemical structure(s):
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Molecular weight: 361.44
Iso. SMILES: CC1=C(C(=O)NC(=O)N1)/C=C/C(=O)N[C@@H](CO)C[S@@](=O)CSC
InChI Key: XKLZIVIOZDNKEQ-CLQLPEFOSA-N
Can. SMILES: CC1=C(/C=C/C(=O)N[C@@H](CO)C[S@@](=O)CSC)C(=O)NC(=O)N1
InChI: InChI=1S/C13H19N3O5S2/c1-8-10(12(19)16-13(20)14-8)3-4-11(18)15-9(5-17)6-23(21)7-22-2/h3-4,9,17H,5-7H2,1-2H3,(H,15,18)(H2,14,16,19,20)/b4-3+/t9-,23+/m0/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/9543443
Citations:
  • https://pubs.acs.org/doi/10.1021/acschembio.5b00284#:~:text=Sparsomycin%20is%20a%20model%20protein,to%20the%20large%20ribosome%20subunit.
  • https://www.pnas.org/doi/full/10.1073/pnas.96.16.9003

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