(2S,5R,6R)-6-[2-amino-2-(4-hydroxyphenyl)(1,2-13C2)acetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

• ChemBase ID: 160573
• Molecular Formular: C16H19N3O5S
• Molecular Mass: 368.38287857
• Monoisotopic Mass: 368.10828629
• SMILES: [C@H]1(C(=O)N2[C@@H]1SC([C@@H]2C(=O)O)(C)C)N[13C](=O)[13CH](c1ccc(cc1)O)[15NH2]
• Canonical SMILES: O=[13C]([13CH](c1ccc(cc1)O)[15NH2])N[C@@H]1C(=O)N2[C@@H]1SC([C@@H]2C(=O)O)(C)C
• InChI: InChI=1S/C16H19N3O5S/c1-16(2)11(15(23)24)19-13(22)10(14(19)25-16)18-12(21)9(17)7-3-5-8(20)6-4-7/h3-6,9-11,14,20H,17H2,1-2H3,(H,18,21)(H,23,24)/t9?,10-,11+,14-/m1/s1/i9+1,12+1,17+1
• InChIKey: LSQZJLSUYDQPKJ-RNBHMYTQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,5R,6R)-6-[2-amino-2-(4-hydroxyphenyl)(1,2-^1^3C₂)acetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• IUPAC Traditional name: (2S,5R,6R)-6-[2-amino-2-(4-hydroxyphenyl)(1,2-^1^3C₂)acetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• Synonyms: (2S,5R,6R)-6-[[(2R)-2-Amino-2-(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid-13C2,15N; AMPC-13C2,15N; Amoxycillin-13C2,15N; Helvamox-13C2,15N; Pasetocin-13C2,15N; Amoxicillin-13C2,15N(Mixture of Diastereomers) see A634238 and A634237

Database IDs

• PubChem SID: 162254708
• PubChem CID: 46780380

CALCULATED PROPERTIES

• Acid pKa: 3.2314606
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -2.3092988
• LogD (pH = 7.4): -2.5697672
• Log P: -2.3101761
• Molar Refractivity: 89.5044 cm^3
• Polarizability: 35.524654 Å^3
• Polar Surface Area: 132.96 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A634236

Labelled semi-synthetic antibiotic related to Penicillin. Antibacterial.

REFERENCES

• Brogden, R.N., et al.: Drugs, 18, 169 (1979)
• Bird, A.E., et al.: Anal. Profiles Drug Subs. Excip., 23, 1 (1979)