(2R,4S)-2-[(R)-carboxy[(2R)-2-[(4-ethyl-2,3-dioxopiperazine-1-carbonyl)amino]-2-phenylacetamido]methyl]-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid

• ChemBase ID: 176754
• Molecular Formular: C23H29N5O8S
• Molecular Mass: 535.57006
• Monoisotopic Mass: 535.17368391
• SMILES: N(C(=O)[C@H](NC(=O)N1C(=O)C(=O)N(CC1)CC)c1ccccc1)[C@@H]([C@@H]1N[C@H](C(S1)(C)C)C(=O)O)C(=O)O
• Canonical SMILES: CCN1CCN(C(=O)C1=O)C(=O)N[C@H](c1ccccc1)C(=O)N[C@@H]([C@@H]1N[C@H](C(S1)(C)C)C(=O)O)C(=O)O
• InChI: InChI=1S/C23H29N5O8S/c1-4-27-10-11-28(19(31)18(27)30)22(36)25-13(12-8-6-5-7-9-12)16(29)24-14(20(32)33)17-26-15(21(34)35)23(2,3)37-17/h5-9,13-15,17,26H,4,10-11H2,1-3H3,(H,24,29)(H,25,36)(H,32,33)(H,34,35)/t13-,14+,15+,17-/m1/s1
• InChIKey: OKSUEATVFIVTFV-WBTNSWJXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,4S)-2-[(R)-carboxy[(2R)-2-[(4-ethyl-2,3-dioxopiperazine-1-carbonyl)amino]-2-phenylacetamido]methyl]-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid
• IUPAC Traditional name: (2R,4S)-2-[(R)-carboxy[(2R)-2-(4-ethyl-2,3-dioxopiperazine-1-carbonylamino)-2-phenylacetamido]methyl]-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid
• Synonyms: [2R-[2α[R*(R*)],4β]]-4-Carboxy-α-[[[[(4-ethyl-2,3-dioxo-1-piperazinyl)carbonyl]amino]phenylacetyl]amino]-5,5-dimethyl-2-thiazolidineacetic Acid; α-(4-Ethyl-2,3-dioxo-1-piperazinecarboxamido)benzylpenicilloic Acid (T 1220 B); Piperacillin EP Impurity B; Piperacilloic Acid

Database IDs

• CAS Number: 64817-22-7
• PubChem SID: 164232664
• PubChem CID: 54669584

CALCULATED PROPERTIES

• Acid pKa: 2.6392198
• H Acceptors: 9
• H Donor: 5
• LogD (pH = 5.5): -4.4267683
• LogD (pH = 7.4): -6.5168524
• Log P: -2.5868757
• Molar Refractivity: 129.3745 cm^3
• Polarizability: 50.877766 Å^3
• Polar Surface Area: 185.45 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - P479970

A degradation product of Piperacillin (P479950), a new β-lactam antibiotic.

REFERENCES

• Waxman, D.J., et al.: J. Biol. Chem., 255, 3964 (1980)
• Waley, S.G., et al.: Biochem. J., et al.: 205, 631 (1980)