Compound ID | 336

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OCP 9-176

Synonym(s): L656575

Class: Beta-lactam

Agent Type: Semisynthetic; Small molecule; Direct acting;
Spectrum of activity: Gram-positive & Gram-negative
Mechanism of action: Cell wall synthesis inhibitor
Target Pathogen: Broad spectrum activity
Description: Slightly hydrolysed by TEM-1, PSE-1, K-1, and P99; generally has two fold less activity compared ME1228
Institute where first reported: Meiji Seika Kaisha (Meiji Seika Pharma., Japan)
Year first mentioned: 1987
Development status: Experimental
Reason dropped: Activity generally less than ME1228
Chemical structure(s):
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Molecular weight: 590.63
Iso. SMILES: C[C@H]1C(=C(N2[C@H](O1)[C@@H](C2=O)NC(=O)/C(=N/OC(C)(C)C(=O)O)/C3=CSC(=N3)N)C(=O)[O-])CSC4=CC=[N+](C=C4)C
InChI Key: AXPAGQFNDQXHIX-SHEAVQNQSA-N
Can. SMILES: C[C@H]1C(=C(C(=O)[O-])N2C(=O)[C@H]([C@H]2O1)NC(=O)/C(=N/OC(C)(C)C(=O)O)/C3=CSC(=N3)N)CSC4=CC=[N+](C)C=C4
InChI: InChI=1S/C24H26N6O8S2/c1-11-13(9-39-12-5-7-29(4)8-6-12)17(21(33)34)30-19(32)16(20(30)37-11)27-18(31)15(14-10-40-23(25)26-14)28-38-24(2,3)22(35)36/h5-8,10-11,16,20H,9H2,1-4H3,(H4-,25,26,27,31,33,34,35,36)/b28-15+/t11-,16+,20+/m0/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/9576861
Citations:
  • https://doi.org/10.1016/0732-8893(91)90048-K
  • https://doi.org/10.7164/antibiotics.41.1137
  • https://doi.org/10.7164/antibiotics.41.1154
  • https://doi.org/10.7164/antibiotics.41.1130

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