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

• ChemBase ID: 160594
• Molecular Formular: C16H21N3O5S
• Molecular Mass: 367.42004
• Monoisotopic Mass: 367.12019179
• SMILES: c1ccc(cc1)[C@H](C(=O)N[C@@H]([C@@H]1N[C@H](C(S1)(C)C)C(=O)O)C(=O)O)N
• Canonical SMILES: 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/C16H21N3O5S/c1-16(2)11(15(23)24)19-13(25-16)10(14(21)22)18-12(20)9(17)8-6-4-3-5-7-8/h3-7,9-11,13,19H,17H2,1-2H3,(H,18,20)(H,21,22)(H,23,24)/t9-,10+,11+,13-/m1/s1
• InChIKey: KDAWOPKDXRJNHV-MPPDQPJWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,4S)-2-[(R)-[(2R)-2-amino-2-phenylacetamido](carboxy)methyl]-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid
• IUPAC Traditional name: (2R,4S)-2-[(R)-[(2R)-2-amino-2-phenylacetamido](carboxy)methyl]-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid
• Synonyms: (2R)-(2R)-2-Phenylglycyl-2-[(2R,4S)-4-carboxy-5,5-dimethyl-2-thiazolidinyl]glycine; α-(2-Amino-2-phenylacetamido)-4-carboxy-5,5-dimethyl-2-thiazolidineacetic Acid; [2R-[2α[R*(R*)],4β]]-α-[(Aminophenylacetyl)amino]-4-carboxy-5,5-dimethyl-2-thiazolidineacetic Acid; α-Aminobenzylpenicilloic Acid; Ampicillin EP Impurity D; Ampicilloic Acid

Database IDs

• CAS Number: 32746-94-4
• PubChem SID: 162254729
• PubChem CID: 6914605

CALCULATED PROPERTIES

• Acid pKa: 2.630011
• H Acceptors: 7
• H Donor: 5
• LogD (pH = 5.5): -4.100973
• LogD (pH = 7.4): -4.955114
• Log P: -4.0844855
• Molar Refractivity: 90.6013 cm^3
• Polarizability: 36.45022 Å^3
• Polar Surface Area: 141.75 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A634320

Ampicilloic Acid is a metabolite and impurity of the semi-synthetic antibiotic Ampicillin (A634300).

REFERENCES

• Miyazaki, K. et al.: Chem. Pharmac. Bull., 22, 1910 (1974)
• Komatsu, T. et al.: Rins. Yak., 8, 35 (1974)
• Bird, A.E. et al.: J. Pharm. Pharmacol., 35, 138 (1974)
• Yongxin, Z. et al.: J. Liq. Chrom. Rel Technol., 22, 1403 (1974)