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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))
Compound class: Natural product
Comment: Phenoxymethylpenicillin is a β-lactam, natural penicillin antibacterial. It has broad-spectrum activity against Gram-positive aerobes, limited activity against Gram-negative organisms, and is not generally used against anaerobes.
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Natural product
Approved drug? Yes. UK MHRA (1998)  |  US FDA (1958)
WHO Essential Medicine WHO Essential Medicines List (EML) (23rd List, 2023). Access PDF version.
Click to view more information about the WHO Model Lists of Essential Medicines.
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
Specialist databases
Antibiotic DB Antibiotic DB Database logo Penicillin V
Other databases
BindingDB Ligand 50370584
CAS Registry No. 87-08-1 (source: WHO INN record)
ChEMBL Ligand CHEMBL615
DrugBank Ligand DB00417
DrugCentral Ligand 2083
GtoPdb PubChem SID 405560361
PubChem CID 6869
RCSB PDB Ligand PNV
Search Google for chemical match using the InChIKey BPLBGHOLXOTWMN-MBNYWOFBSA-N
Search Google for chemicals with the same backbone BPLBGHOLXOTWMN
Search PubMed clinical trials phenoxymethylpenicillin
Search PubMed titles phenoxymethylpenicillin
Search PubMed titles/abstracts phenoxymethylpenicillin
UniChem Compound Search for chemical match using the InChIKey BPLBGHOLXOTWMN-MBNYWOFBSA-N
UniChem Connectivity Search for chemical match using the InChIKey BPLBGHOLXOTWMN-MBNYWOFBSA-N