Compound ID | 159

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SQ641

Class: Nucleoside analogue

Agent Type: Semisynthetic; Small molecule; Direct acting;
Spectrum of activity: Gram-positive
Mechanism of action: Cell wall synthesis inhibitor. MraY inhibitor / translocase I inhibitor (TLI 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 Clostridium difficile
Description: Semisynthetic derivative of the natural product capuramycin from Streptomyces griseus
Institute where first reported: Sequella, USA
Year first mentioned: 1986
Development status: Experimental
Chemical structure(s):
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Molecular weight: 739.81
Iso. SMILES: CCCCCCCCCC(=O)O[C@@H]1[C@@H]([C@H](O[C@H]1N2C=CC(=O)NC2=O)[C@H](C(=O)N)O[C@@H]3[C@H]([C@H](C=C(O3)C(=O)N[C@H]4CCC[C@H](NC4O)C)O)O)OC
InChI Key: GHMYTLUBNQSWIA-QPOYEQHISA-N
Can. SMILES: CCCCCCCCCC(=O)O[C@@H]1[C@@H]([C@@H]([C@H](C(=O)N)O[C@@H]2[C@H]([C@H](C=C(C(=O)N[C@H]3CCC[C@@H](C)NC3O)O2)O)O)O[C@H]1N4C=CC(=O)NC4=O)OC
InChI: InChI=1S/C34H53N5O13/c1-4-5-6-7-8-9-10-14-23(42)50-28-25(48-3)26(51-32(28)39-16-15-22(41)38-34(39)47)27(29(35)44)52-33-24(43)20(40)17-21(49-33)31(46)37-19-13-11-12-18(2)36-30(19)45/h15-20,24-28,30,32-33,36,40,43,45H,4-14H2,1-3H3,(H2,35,44)(H,37,46)(H,38,41,47)/t18-,19+,20+,24+,25-,26+,27-,28-,30?,32-,33-/m1/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/71589730
Guide to Pharmacology: SQ641
Citations:
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2224724/
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2976629/
  • http://www.abstractsonline.com/Plan/ViewAbstract.aspx?mID=3529&sKey=d062d52f-dbc1-4812-a8f5-43f97e8425a9&cKey=675b3e8c-1f80-41c2-9668-ed40c4db2bda&mKey=5d6b1802-e453-486b-bcbb-b11d1182d8bb
  • https://pmc.ncbi.nlm.nih.gov/articles/PMC3910727/

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