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
Classification Click here for help
Compound class Natural product or derivative
Approved drug? Yes (FDA (1958), UK (1998))
WHO Essential Medicine WHO Model List of Essential Medicines (21st List, 2019). Access PDF version.
International Nonproprietary Names Click here for help
INN number INN
518 phenoxymethylpenicillin
Synonyms Click here for help
Oracillin® | PC Pen VK® | Pen-V® | penicillin V | Penicillin VK | PNV
Database Links Click here for help
BindingDB Ligand 50370584
CAS Registry No. 87-08-1 (source: WHO INN record)
ChEMBL Ligand CHEMBL615
DrugBank Ligand DB00417
GtoPdb PubChem SID 405560361
PubChem CID 6869
RCSB PDB Ligand PNV
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