penicillin G   Click here for help

GtoPdb Ligand ID: 4796

Synonyms: penicillin G sodium | penicillin-G potassium
Approved drug PDB Ligand
penicillin G is an approved drug (FDA (1947))
Compound class: Synthetic organic
Comment: Penicillin G (benzylpenicillin) is a narrow spectrum penicillin antibacterial.
Penicillin G is is one of the access group antibacterials on the World Health Organization's Model List of Essential Medicines (link provided in the Classification table under the Summary tab).
Click here for help

Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

✖

View interactive charts of activity data across species
2D Structure
Click here for help

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.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. 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.

✖
Hydrogen bond acceptors 6
Hydrogen bond donors 2
Rotatable bonds 5
Topological polar surface area 112.01
Molecular weight 334.1
XLogP 1.49
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Click here for help

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.

✖
Canonical SMILES O=C(Cc1ccccc1)NC1C(=O)N2C1SC(C2C(=O)O)(C)C
Isomeric SMILES O=C(Cc1ccccc1)N[C@@H]1C(=O)N2[C@@H]1SC([C@@H]2C(=O)O)(C)C
InChI InChI=1S/C16H18N2O4S/c1-16(2)12(15(21)22)18-13(20)11(14(18)23-16)17-10(19)8-9-6-4-3-5-7-9/h3-7,11-12,14H,8H2,1-2H3,(H,17,19)(H,21,22)/t11-,12+,14-/m1/s1
InChI Key JGSARLDLIJGVTE-MBNYWOFBSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1947))
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.
Prodrug penamecillin
IUPAC Name Click here for help
(2S,5R,6R)-3,3-dimethyl-7-oxo-6-(2-phenylacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
International Nonproprietary Names Click here for help
INN number INN
221 benethamine penicillin
203 benzathine benzylpenicillin
58 benzylpenicillin
827 clemizole penicillin
736 phenyracillin
Synonyms Click here for help
penicillin G sodium | penicillin-G potassium
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Penicillin G (Benzylpenicillin)
Other databases
CAS Registry No. 61-33-6 (source: Scifinder)
ChEMBL Ligand CHEMBL29
DrugBank Ligand DB01053
DrugCentral Ligand 2082
GtoPdb PubChem SID 178101498
Immunopaedia Search penicillin
PubChem CID 5904
RCSB PDB Ligand PNN
Search Google for chemical match using the InChIKey JGSARLDLIJGVTE-MBNYWOFBSA-N
Search Google for chemicals with the same backbone JGSARLDLIJGVTE
Search PubMed clinical trials phenyracillin
Search PubMed titles phenyracillin
Search PubMed titles/abstracts phenyracillin
UniChem Compound Search for chemical match using the InChIKey JGSARLDLIJGVTE-MBNYWOFBSA-N
UniChem Connectivity Search for chemical match using the InChIKey JGSARLDLIJGVTE-MBNYWOFBSA-N
Wikipedia Penicillin_G