(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: 171572
• Molecular Formular: C12H19N3O5S
• Molecular Mass: 317.36136
• Monoisotopic Mass: 317.10454172
• SMILES: [C@@H]1(C(=O)N2C1CC(=C2C(=O)O)SCCNC=N)[C@@H](C)O.O
• Canonical SMILES: C[C@H]([C@@H]1C2CC(=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-JGJCRCBPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (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: (6S)-6-[(1R)-1-hydroxyethyl]-3-[(2-methanimidamidoethyl)sulfanyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid hydrate
• Synonyms: MK-787; Imipenem, Monohydrate

Database IDs

• CAS Number: 74431-23-5
• PubChem SID: 164227482
• PubChem CID: 71749470

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: DMSO; Methanol; Water
• Apperance: Off-White to Pale Yellow Solid
• Melting Point: 193-198°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - I465200

An extremely broad-spectrum semi-synthetic antibiotic.

REFERENCES

• Oberholtzer, E.R.: Anal. Profiles Drug Subs., 17, 73 (1988)