(5R,6S)-6-[(1R)-1-hydroxyethyl]-3-[(2-methanimidamidoethyl)sulfanyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid hydrate

• ChemBase ID: 154047
• Molecular Formular: C12H19N3O5S
• Molecular Mass: 317.36136
• Monoisotopic Mass: 317.10454172
• SMILES: C[C@H]([C@@H]1[C@H]2CC(=C(N2C1=O)C(=O)O)SCCNC=N)O.O
• Canonical SMILES: C[C@H]([C@@H]1[C@H]2CC(=C(N2C1=O)C(=O)O)SCCNC=N)O.O
• InChI: InChI=1S/C12H17N3O4S.H2O/c1-6(16)9-7-4-8(20-3-2-14-5-13)10(12(18)19)15(7)11(9)17;/h5-7,9,16H,2-4H2,1H3,(H2,13,14)(H,18,19);1H2/t6-,7-,9-;/m1./s1
• InChIKey: GSOSVVULSKVSLQ-JJVRHELESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (5R,6S)-6-[(1R)-1-hydroxyethyl]-3-[(2-methanimidamidoethyl)sulfanyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid hydrate
• IUPAC Traditional name: imipenemum hydrate
• Synonyms: (5R,6S)-6-[(1R)-1-Hydroxyethyl]-3-[[2-[(iminomethyl)amino]ethyl]thio]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid monohydrate; Primaxin monohydrate; Tienam monohydrate; Imipenem monohydrate; Imipenem monohydrate

Database IDs

• CAS Number: 74431-23-5
• EC Number: 264-734-5
• MDL Number: MFCD09753321
• PubChem SID: 162248186
• PubChem CID: 5282372

CALCULATED PROPERTIES

• Acid pKa: 3.9336088
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -3.8067136
• LogD (pH = 7.4): -3.7972186
• Log P: -3.7971773
• Molar Refractivity: 86.1362 cm^3
• Polarizability: 28.549414 Å^3
• Polar Surface Area: 113.72 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: >5 mg/mL
• Apperance: white solid

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥98% (HPLC); 95+%
• Empirical Formula (Hill Notation): C12H17N3O4S · H2O

DETAILS

Sigma Aldrich - I0160

Biochem/physiol Actions
Imipenem monohydrate is a broad spectrum B-lactam antibiotic. It is a member of the carbapenem class of "magic bullet" antibiotics for severe infections.