ampicillin   Click here for help

GtoPdb Ligand ID: 10896

Synonyms: aminobenzylpenicillin | KS-R1 | Penbritin® | Polycillin | Principen®
Approved drug PDB Ligand
ampicillin is an approved drug (FDA (1965))
Compound class: Synthetic organic
Comment: Ampicillin is a broad-spectrum, semi-synthetic, β-lactam penicillin class antibiotic. It is resistant to hydrolysis by a variety of β-lactamases, so can be to treat a diverse range of infections caused by Gram-positive and Gram-negative infections.
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 7
Hydrogen bond donors 3
Rotatable bonds 5
Topological polar surface area 138.03
Molecular weight 349.11
XLogP -1.73
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Click here for help
Canonical SMILES N[C@H](c1ccccc1)C(=O)N[C@@H]1C(=O)N2[C@@H]1SC([C@@H]2C(=O)O)(C)C
Isomeric SMILES N[C@H](c1ccccc1)C(=O)N[C@@H]1C(=O)N2[C@@H]1SC([C@@H]2C(=O)O)(C)C
InChI InChI=1S/C16H19N3O4S/c1-16(2)11(15(22)23)19-13(21)10(14(19)24-16)18-12(20)9(17)8-6-4-3-5-7-8/h3-7,9-11,14H,17H2,1-2H3,(H,18,20)(H,22,23)/t9-,10-,11+,14-/m1/s1
InChI Key AVKUERGKIZMTKX-NJBDSQKTSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1965))
WHO Essential Medicine WHO Model List of Essential Medicines (21st List, 2019). Access PDF version.
IUPAC Name Click here for help
(2S,5R,6R)-6-[[(2R)-2-amino-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
International Nonproprietary Names Click here for help
INN number INN
1339 ampicillin
Synonyms Click here for help
aminobenzylpenicillin | KS-R1 | Penbritin® | Polycillin | Principen®
Database Links Click here for help
BindingDB Ligand 50350465
CAS Registry No. 69-52-3 (source: WHO INN record)
ChEMBL Ligand CHEMBL174
DrugBank Ligand DB00415
DrugCentral Ligand 198
GtoPdb PubChem SID 405560337
PubChem CID 6249
RCSB PDB Ligand AIC
Search Google for chemical match using the InChIKey AVKUERGKIZMTKX-NJBDSQKTSA-N
Search Google for chemicals with the same backbone AVKUERGKIZMTKX
Search PubMed clinical trials ampicillin
Search PubMed titles ampicillin
Search PubMed titles/abstracts ampicillin
Search UniChem for chemical match using the InChIKey AVKUERGKIZMTKX-NJBDSQKTSA-N
Search UniChem for chemicals with the same backbone AVKUERGKIZMTKX