Piperacillin
Athanor · official
C23H27N5O7S · 517.6 g/mol
IUPAC name: 6-[[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
Also called Zosyn, Tazocin, ureidopenicillin
Names and identifiers
- IUPAC name
- 6-[[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
- Synonyms
- Zosyn, Tazocin, ureidopenicillin
+ 13 more
SCHEMBL4486297, 6-{2-[(4-ethyl-2,3-dioxopiperazine-1-carbonyl)amino]-2-phenylacetamido}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, CHEMBL1616926, EBC-13282, STK397060, AKOS005434036, DB-017799, ST50891174, EN300-27694695, 6-(2-(4-ethyl-2,3-dioxopiperazine-1-carboxamido)-2-phenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-{[{[(4-ethyl-2,3-dioxopiperazin-1-yl)carbonyl]amino}(phenyl)acetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-{2-[(4-ethyl-2,3-dioxo(1,4-diazaperhydroinyl))carbonylamino]-2-phenylacetyla mino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6beta-[(R)-2-(4-ethyl-2,3-dioxo-piperazine-1-carbonylamino)-2-phenyl-acetylamino]-penicillanic acid
- Molecular formula
- C23H27N5O7S
- Empirical formula
- C23H27N5O7S
- Molecular weight
- 517.6 g/mol
- Exact mass
- 517.16312
- CAS number
- 61477-96-1
- PubChem CID
- 4835
- Canonical SMILES
- CCN1CCN(C(=O)C1=O)C(=O)NC(C2=CC=CC=C2)C(=O)NC3C4N(C3=O)C(C(S4)(C)C)C(=O)O
- Isomeric SMILES
- CCN1CCN(C(=O)C1=O)C(=O)NC(C2=CC=CC=C2)C(=O)NC3C4N(C3=O)C(C(S4)(C)C)C(=O)O
- 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)
- InChIKey
- IVBHGBMCVLDMKU-UHFFFAOYSA-N
- Molfile
Names, InChI and the identifiers from PubChem, retrieved 2026-10-14.
Calculated
- Heavy atoms
- 36
- Rings
- 4
- Aromatic rings
- 1
- Fraction sp³ carbons (Fsp3)
- 0.48
- H-bond donors
- 3
- H-bond acceptors
- 7 computed here · PubChem 8
- Rotatable bonds
- 6
- TPSA (Ų)
- 156.4 computed here · PubChem 182
- Formal charge
- 0
- XLogP3
- 0.5 PubChem
- Complexity
- 982 PubChem
- Stereocenters
- 0 defined, 4 undefinedCIP: C10: undefined · C14: undefined · C18: undefined · C26: undefined
- Double-bond geometry
- None specified
- Point group
- C1 of one 3D conformer with its hydrogens, by Athanor’s engine (as in the app)
Elemental analysis
- C53.38%
- H5.26%
- N13.53%
- O21.64%
- S6.20%
Isotope pattern
Each peak is a nominal mass with its abundance-weighted exact mass, as a percentage of the tallest, from IUPAC natural isotope abundances.
Computed from the structure with RDKit 2026.09 when this page was built, beside PubChem's own computed values from its record; where the two differ, both are shown.
Predicted
- log P
- -0.24 Crippen (Wildman and Crippen 1999)
- log S (water solubility)
- -2.62 ESOL (Delaney 2004), log mol/L
- Synthetic accessibility
- 3.95 SA score, 1 easy to 10 hard (Ertl and Schuffenhauer 2009)
Drug-likeness: Lipinski’s rule of five
- Molecular weight ≤ 500: 517.56
- log P ≤ 5 (Crippen): -0.24
- H-bond donors ≤ 5: 3
- H-bond acceptors ≤ 10: 7
Breaks 1 of the four rules.
¹³C NMR shifts, predicted
Predictions, not measurements; each names its method. A measured log P, where a source reports one, is under Physical properties.
Safety
No GHS hazard classification was found in the sources.
Safety data sheets on the supplier’s page: Mcule, A2B Chem, SynHet - Synthetic Heterocycles.
Always read the supplier’s safety data sheet before working with it.
Spectra
- LC-MSMassBank Europe (TQD, Waters · LC-ESI-QQ · POSITIVE) · MassBank Europe (TQD, Waters · LC-ESI-QQ · POSITIVE) · MassBank Europe (TQD, Waters · LC-ESI-QQ · POSITIVE) · MassBank Europe (TQD, Waters · LC-ESI-QQ · POSITIVE) · MassBank Europe (TQD, Waters · LC-ESI-QQ · POSITIVE) · MassBank Europe (TQD, Waters · LC-ESI-QQ · POSITIVE)
Experimental spectra held by these sources; each link opens the source's own record.
Literature
Reading PubChem, OpenAlex and GSRS…
Bioactivity
Reading ChEMBL…
References
- [1]MassBank Europe · Linked only · via PubChem · retrieved 2026-10-14
- [2]SpectraBase · Linked only · via PubChem · retrieved 2026-10-14
- ·Calculated values: computed by Athanor with RDKit 2026.09 from the structure.
- ·Literature on PubChem
Data last updated 2026-10-14.