2-[5-(4-hydroxyphenyl)-3,6-dioxopiperazin-2-yl]-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid

• ChemBase ID: 160572
• Molecular Formular: C16H19N3O5S
• Molecular Mass: 365.40416
• Monoisotopic Mass: 365.10454172
• SMILES: c1(ccc(cc1)C1NC(=O)C(NC1=O)C1NC(C(S1)(C)C)C(=O)O)O
• Canonical SMILES: Oc1ccc(cc1)C1NC(=O)C(NC1=O)C1NC(C(S1)(C)C)C(=O)O
• InChI: InChI=1S/C16H19N3O5S/c1-16(2)11(15(23)24)19-14(25-16)10-13(22)17-9(12(21)18-10)7-3-5-8(20)6-4-7/h3-6,9-11,14,19-20H,1-2H3,(H,17,22)(H,18,21)(H,23,24)
• InChIKey: IIZCCQJEPBWGJU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[5-(4-hydroxyphenyl)-3,6-dioxopiperazin-2-yl]-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid
• IUPAC Traditional name: 2-[5-(4-hydroxyphenyl)-3,6-dioxopiperazin-2-yl]-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid
• Synonyms: 2-[5-(4-Hydroxyphenyl)-3,6-dioxo-2-piperazinyl]-5,5-dimethyl-4-thiazolidinecarboxylic Acid; 2,5-Amoxipiperazinedione; Amoxicillin Piperazine-2,5-dione; Amoxicillin Diketopiperazine(Mixture of Diastereomers)

Database IDs

• CAS Number: 94659-47-9
• PubChem SID: 162254707
• PubChem CID: 46780379

CALCULATED PROPERTIES

• Acid pKa: 2.75702
• H Acceptors: 6
• H Donor: 5
• LogD (pH = 5.5): -2.087367
• LogD (pH = 7.4): -2.9981778
• Log P: -2.0404384
• Molar Refractivity: 89.3823 cm^3
• Polarizability: 35.524357 Å^3
• Polar Surface Area: 127.76 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Alkaline solution; DMSO
• Apperance: Pale Yellow Solid
• Melting Point: >218°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - A634234

The major metabolite of Amoxicillin (AMO)(A634235).

REFERENCES

• Dewdney, J., et al.: Food Chem. Toxic, 29, 477 (1991)
• Connor, S., et al.: J. Pharm. Pharmacol., 46, 128 (1991)
• Hernandez, E., et al.: Vet. J., 170, 237 (1991)