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

• ChemBase ID: 135970
• Molecular Formular: C16H19N3O4S
• Molecular Mass: 350.3981689
• Monoisotopic Mass: 350.106662
• SMILES: CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)[C@@H](c1ccccc1)[15NH2])C(=O)O)C
• Canonical SMILES: [15NH2][C@H](c1ccccc1)C(=O)N[C@@H]1C(=O)N2[C@@H]1SC([C@@H]2C(=O)O)(C)C
• InChI: InChI=1S/C16H19N3O4S/c1-16(2)11(15(22)23)19-13(21)10(14(19)24-16)18-12(20)9(17)8-6-4-3-5-7-8/h3-7,9-11,14H,17H2,1-2H3,(H,18,20)(H,22,23)/t9-,10-,11+,14-/m1/s1/i17+1
• InChIKey: AVKUERGKIZMTKX-UEHSRBDYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,5R,6R)-6-[(2R)-2-amino-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• IUPAC Traditional name: ampicillin
• Synonyms: D-(-)-α-Aminobenzylpenicillin-15N; Ampicillin-(amine-15N); D-(-)-α-氨苄青霉素-15N; 氨苄西林-15N（胺-15N）; 氨苄西林-15N

Database IDs

• CAS Number: 1217467-27-0
• MDL Number: MFCD08702870
• PubChem SID: 162230241
• PubChem CID: 71309518

CALCULATED PROPERTIES

• Acid pKa: 3.2380536
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -2.0056438
• LogD (pH = 7.4): -2.2605202
• Log P: -2.0066502
• Molar Refractivity: 87.5235 cm^3
• Polarizability: 34.874416 Å^3
• Polar Surface Area: 112.73 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 198-200 °C (dec.)(lit.)
• Mass Shift: M+1

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38-42/43
• Safety Statements: 22-26-36/37
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H315-H317-H319-H334-H335
• GHS Precautionary statements: P261-P280-P305 + P351 + P338-P342 + P311

Product Information

• Purity: 97% (CP)
• Isotopic Purity: 98 atom % 15N
• Mol. Weight: mol wt 350.38 by atom % calculation
• Empirical Formula (Hill Notation): C16H1915NN2O4S

DETAILS

Sigma Aldrich - 609315

Packaging
This product may be available from bulk stock and can be packaged on demand. For information on pricing, availability and packaging, please contact Stable Isotopes Customer Service.