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 antibiotic.
Penicillin G is on the World Health Organisation's List of Essential Medicines. Click here to access the pdf version of the WHO's 21st Essential Medicines list (2019).
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
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
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 Model List of Essential Medicines (21st List, 2019). Access PDF version.
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
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
Search UniChem for chemical match using the InChIKey JGSARLDLIJGVTE-MBNYWOFBSA-N
Search UniChem for chemicals with the same backbone JGSARLDLIJGVTE
Wikipedia Penicillin_G