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 antibiotic.
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2D Structure
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Physico-chemical Properties
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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
SMILES / InChI / InChIKey
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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
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1981), UK (2011))
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-[(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
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
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