(2S,5R,6R)-6-[(2R)-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

• ChemBase ID: 176753
• Molecular Formular: C23H27N5O7S
• Molecular Mass: 517.55478
• Monoisotopic Mass: 517.16311923
• SMILES: [C@H]1(C(=O)N2[C@@H]1SC([C@@H]2C(=O)O)(C)C)NC(=O)[C@H](NC(=O)N1C(=O)C(=O)N(CC1)CC)c1ccccc1
• 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
• 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
• InChIKey: IVBHGBMCVLDMKU-GXNBUGAJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,5R,6R)-6-[(2R)-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
• IUPAC Traditional name: piperacillin
• Synonyms: (2S,5R,6R)-6-[[(2R)-2-[[(4-Ethyl-2,3-dioxo-1-piperazinyl)carbonyl]amino]-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid; CL 227193; Isipen; Pentcillin; Pipracil; T 1220; Piperacillin

Database IDs

• CAS Number: 61477-96-1
• PubChem SID: 164232663
• PubChem CID: 43672

CALCULATED PROPERTIES

• Acid pKa: 3.4850655
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): -2.2645185
• LogD (pH = 7.4): -3.6383073
• Log P: -0.25849018
• Molar Refractivity: 126.2967 cm^3
• Polarizability: 49.296238 Å^3
• Polar Surface Area: 156.43 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: Crystalline Solid
• Melting Point: 162-165°C (dec.)

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - P479950

Broad spectrum semi-synthetic antibiotic related to Penicillin. Antibacterial.

REFERENCES

• Takai, A., et al.: Chemotherapy, 25, 816 (1977)
• Bodey, G.P., et al.: Antimicrob. Agents Chemother., 14, 78 (1977)
• Kuck, N.A., et al.: J. Antibiot., 31, 1175 (1977)