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

• ChemBase ID: 160590
• Molecular Formular: C16H21N3O6S
• Molecular Mass: 383.41944
• Monoisotopic Mass: 383.11510641
• SMILES: c1c(ccc(c1)C(N)C(=O)N[C@H]([C@@H]1N[C@H](C(S1)(C)C)C(=O)O)C(=O)O)O
• Canonical SMILES: O=C(C(c1ccc(cc1)O)N)N[C@H]([C@@H]1N[C@H](C(S1)(C)C)C(=O)O)C(=O)O
• InChI: InChI=1S/C16H21N3O6S/c1-16(2)11(15(24)25)19-13(26-16)10(14(22)23)18-12(21)9(17)7-3-5-8(20)6-4-7/h3-6,9-11,13,19-20H,17H2,1-2H3,(H,18,21)(H,22,23)(H,24,25)/t9?,10-,11+,13-/m1/s1
• InChIKey: LHHKJQFIKHAUIA-JAUFEGHXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,4S)-2-[(S)-[2-amino-2-(4-hydroxyphenyl)acetamido](carboxy)methyl]-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid
• IUPAC Traditional name: (2R,4S)-2-[(S)-[2-amino-2-(4-hydroxyphenyl)acetamido](carboxy)methyl]-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid
• Synonyms: (αR,2R,4S)-α-[[Amino(4-hydroxyphenyl)acetyl]amino]-4-carboxy-5,5-dimethyl-2-thiazolidineacetic Acid; Amoxipenicilloic Acid; Amoxicillin Penilloic Acid; Amoxycilloic Acid (Mixture of Diastereomers)

Database IDs

• PubChem SID: 162254725
• PubChem CID: 71313389

CALCULATED PROPERTIES

• Acid pKa: 2.544552
• H Acceptors: 8
• H Donor: 6
• LogD (pH = 5.5): -4.427465
• LogD (pH = 7.4): -5.2912397
• Log P: -4.4086614
• Molar Refractivity: 92.5822 cm^3
• Polarizability: 37.103813 Å^3
• Polar Surface Area: 161.98 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: White Solid
• Melting Point: 203-205°C (dec.)

Safety Information

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

DETAILS

Toronto Research Chemicals - A634265

Degradation product/impurity of AmoxicillinContain small amount (~5%) of diastereomer.

REFERENCES

• Connor, S., et al.: J. Pharm. Pharmacol., 46, 128 (1994)
• Van G., et al.: J. Vet. Pharmacol. Ther., 26, 139 (1994)