2-[carboxy(2-phenoxyacetamido)methyl]-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid

• ChemBase ID: 176265
• Molecular Formular: C16H20N2O6S
• Molecular Mass: 368.4048
• Monoisotopic Mass: 368.10420737
• SMILES: C1(SC(NC1C(=O)O)C(NC(=O)COc1ccccc1)C(=O)O)(C)C
• Canonical SMILES: O=C(NC(C1NC(C(S1)(C)C)C(=O)O)C(=O)O)COc1ccccc1
• InChI: InChI=1S/C16H20N2O6S/c1-16(2)12(15(22)23)18-13(25-16)11(14(20)21)17-10(19)8-24-9-6-4-3-5-7-9/h3-7,11-13,18H,8H2,1-2H3,(H,17,19)(H,20,21)(H,22,23)
• InChIKey: FJTUHYOOCYRLJI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[carboxy(2-phenoxyacetamido)methyl]-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid
• IUPAC Traditional name: 2-[carboxy(2-phenoxyacetamido)methyl]-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid
• Synonyms: 4-Carboxy-5,5-dimethyl-α-[(2-phenoxyacetyl)amino]-2-thiazolidineacetic Acid; (Phenoxymethyl)penicilloic Acid; NSC 163496; NSC 74505; Penicilloic V Acid

Database IDs

• CAS Number: 1049-84-9
• PubChem SID: 164232175
• PubChem CID: 96439

CALCULATED PROPERTIES

• Acid pKa: 2.5369558
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): -3.4930577
• LogD (pH = 7.4): -5.488147
• Log P: -1.5946555
• Molar Refractivity: 88.8458 cm^3
• Polarizability: 35.64833 Å^3
• Polar Surface Area: 124.96 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Nodium Hydroxide and Water

DETAILS

Toronto Research Chemicals - P223515

Degradation product of Penicillin V.

REFERENCES

• Christensen, L., et al.: Biotechnol. Bioeng., 44, 165 (1994)
• Schiesel, S., et al.: Anal. Bioanal. Chem., 396, 1655 (1994)