phenoxymethylpenicillin   Click here for help

GtoPdb Ligand ID: 10920

Synonyms: Oracillin® | PC Pen VK® | Pen-V® | penicillin V | Penicillin VK | PNV
Approved drug PDB Ligand
phenoxymethylpenicillin is an approved drug (FDA (1958), UK (1998))
Comment: Phenoxymethylpenicillin is a β-lactam, natural penicillin antibiotic. It has broad-spectrum activity against Gram-positive aerobes, limited activity against Gram-negative organisms, and is not generally used against anaerobes.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 6
Hydrogen bond donors 2
Rotatable bonds 6
Topological polar surface area 121.24
Molecular weight 350.09
XLogP 1.36
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES O=C(N[C@@H]1C(=O)N2[C@@H]1SC([C@@H]2C(=O)O)(C)C)COc1ccccc1
Isomeric SMILES O=C(N[C@@H]1C(=O)N2[C@@H]1SC([C@@H]2C(=O)O)(C)C)COc1ccccc1
InChI InChI=1S/C16H18N2O5S/c1-16(2)12(15(21)22)18-13(20)11(14(18)24-16)17-10(19)8-23-9-6-4-3-5-7-9/h3-7,11-12,14H,8H2,1-2H3,(H,17,19)(H,21,22)/t11-,12+,14-/m1/s1
InChI Key BPLBGHOLXOTWMN-MBNYWOFBSA-N
References
1. Jacobs MR, Good CE, Windau AR, Bajaksouzian S, Biek D, Critchley IA, Sader HS, Jones RN. (2010)
Activity of ceftaroline against recent emerging serotypes of Streptococcus pneumoniae in the United States.
Antimicrob Agents Chemother, 54 (6): 2716-9. [PMID:20308374]