(4S)-2-{[(2R)-2-amino-2-(4-hydroxyphenyl)acetamido]methyl}-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid

• ChemBase ID: 160188
• Molecular Formular: C15H21N3O4S
• Molecular Mass: 339.40994
• Monoisotopic Mass: 339.12527717
• SMILES: c1c(ccc(c1)[C@@H](N)C(=O)NCC1N[C@H](C(S1)(C)C)C(=O)O)O
• Canonical SMILES: O=C([C@@H](c1ccc(cc1)O)N)NCC1N[C@H](C(S1)(C)C)C(=O)O
• InChI: InChI=1S/C15H21N3O4S/c1-15(2)12(14(21)22)18-10(23-15)7-17-13(20)11(16)8-3-5-9(19)6-4-8/h3-6,10-12,18-19H,7,16H2,1-2H3,(H,17,20)(H,21,22)/t10?,11-,12+/m1/s1
• InChIKey: HLJHSXSJKLJNKE-SAIIYOCFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-2-{[(2R)-2-amino-2-(4-hydroxyphenyl)acetamido]methyl}-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid
• IUPAC Traditional name: (4S)-2-{[(2R)-2-amino-2-(4-hydroxyphenyl)acetamido]methyl}-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid
• Synonyms: (4S)-2-[[[(2R)-2-Amino-2-(4-hydroxyphenyl)acetyl]amino]methyl]-5,5-dimethyl-4-thiazolidinecarboxylic Acid (Mixture of Diastereomers)

Database IDs

• PubChem SID: 162254323
• PubChem CID: 71313270

CALCULATED PROPERTIES

• Lipinski's Rule of Five: true
• Acid pKa: 2.9646614
• H Acceptors: 6
• H Donor: 5
• LogD (pH = 5.5): -3.172474
• LogD (pH = 7.4): -2.0552742
• Log P: -2.0966113
• Molar Refractivity: 86.7523 cm^3
• Polarizability: 34.65922 Å^3
• Polar Surface Area: 124.68 Å^2
• Rotatable Bonds: 5

DETAILS

Toronto Research Chemicals - A611620

Degradation product/impurity of Amoxicillin

REFERENCES

• Li, Y., et al.: J. Chromat., 812, 227 (1998)