piperacillin   Click here for help

GtoPdb Ligand ID: 10921

Synonyms: CL 227,193 | CL-227193 | PIPC | T-1220 | Tazocin® (piperacillin + tazobactam)
Approved drug PDB Ligand
piperacillin is an approved drug (FDA (1981), UK (2011))
Compound class: Synthetic organic
Comment: Piperacillin is a broad-spectrum semisynthetic, ampicillin-derived antibacterial.
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 12
Hydrogen bond donors 3
Rotatable bonds 9
Topological polar surface area 181.73
Molecular weight 517.16
XLogP 0.33
No. Lipinski's rules broken 1

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 CCN1CCN(C(=O)C1=O)C(=O)N[C@@H](C(=O)N[C@@H]1C(=O)N2[C@@H]1SC([C@@H]2C(=O)O)(C)C)c1ccccc1
Isomeric SMILES CCN1CCN(C(=O)C1=O)C(=O)N[C@@H](C(=O)N[C@@H]1C(=O)N2[C@@H]1SC([C@@H]2C(=O)O)(C)C)c1ccccc1
InChI InChI=1S/C23H27N5O7S/c1-4-26-10-11-27(19(32)18(26)31)22(35)25-13(12-8-6-5-7-9-12)16(29)24-14-17(30)28-15(21(33)34)23(2,3)36-20(14)28/h5-9,13-15,20H,4,10-11H2,1-3H3,(H,24,29)(H,25,35)(H,33,34)/t13-,14-,15+,20-/m1/s1
InChI Key IVBHGBMCVLDMKU-GXNBUGAJSA-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 Synthetic organic
Approved drug? Yes (FDA (1981), UK (2011))
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.
IUPAC Name Click here for help
(2S,5R,6R)-6-[[(2R)-2-[(4-ethyl-2,3-dioxopiperazine-1-carbonyl)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
4296 piperacillin
Synonyms Click here for help
CL 227,193 | CL-227193 | PIPC | T-1220 | Tazocin® (piperacillin + tazobactam)
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Piperacillin
Other databases
BindingDB Ligand 50240426
CAS Registry No. 61477-96-1 (source: WHO INN record)
ChEMBL Ligand CHEMBL702
DrugBank Ligand DB00319
DrugCentral Ligand 2187
GtoPdb PubChem SID 405560362
PubChem CID 43672
RCSB PDB Ligand WPP
Search Google for chemical match using the InChIKey IVBHGBMCVLDMKU-GXNBUGAJSA-N
Search Google for chemicals with the same backbone IVBHGBMCVLDMKU
Search PubMed clinical trials piperacillin
Search PubMed titles piperacillin
Search PubMed titles/abstracts piperacillin
UniChem Compound Search for chemical match using the InChIKey IVBHGBMCVLDMKU-GXNBUGAJSA-N
UniChem Connectivity Search for chemical match using the InChIKey IVBHGBMCVLDMKU-GXNBUGAJSA-N