(4R,5S,6S)-3-{[(3S,5S)-5-[bis(2H3)methylcarbamoyl]pyrrolidin-3-yl]sulfanyl}-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid

• ChemBase ID: 172689
• Molecular Formular: C17H25N3O5S
• Molecular Mass: 383.4625
• Monoisotopic Mass: 383.15149192
• SMILES: [C@@H]1(C(=O)N2[C@@H]1[C@H](C(=C2C(=O)O)S[C@@H]1CN[C@@H](C1)C(=O)N(C)C)C)[C@@H](C)O
• Canonical SMILES: C[C@H]([C@H]1C(=O)N2[C@@H]1[C@@H](C)C(=C2C(=O)O)S[C@@H]1CN[C@@H](C1)C(=O)N(C)C)O
• InChI: InChI=1S/C17H25N3O5S/c1-7-12-11(8(2)21)16(23)20(12)13(17(24)25)14(7)26-9-5-10(18-6-9)15(22)19(3)4/h7-12,18,21H,5-6H2,1-4H3,(H,24,25)/t7-,8-,9+,10+,11-,12-/m1/s1
• InChIKey: DMJNNHOOLUXYBV-PQTSNVLCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R,5S,6S)-3-{[(3S,5S)-5-[bis(^2H₃)methylcarbamoyl]pyrrolidin-3-yl]sulfanyl}-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
• IUPAC Traditional name: (4R,5S,6S)-3-{[(3S,5S)-5-[bis(^2H₃)methylcarbamoyl]pyrrolidin-3-yl]sulfanyl}-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
• Synonyms: (4R,5S,6S)-3-[[3S,5S)-5-[(Dimethylamino-d6)carbonyl]-3-pyrrolidinyl]thio]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic Acid; ICI 194660-d6; Mepem-d6; Meronem-d6; Meropen-d6; Merrem-d6; Merrem IV-d6; SM 7338-d6; Meropenem-d6

Database IDs

• PubChem SID: 164228599
• PubChem CID: 46782127

CALCULATED PROPERTIES

• Acid pKa: 3.4704194
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): -4.3561654
• LogD (pH = 7.4): -4.3568015
• Log P: -4.353987
• Molar Refractivity: 97.8862 cm^3
• Polarizability: 37.879482 Å^3
• Polar Surface Area: 110.18 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Off-White to Pale Yellow Solid
• Melting Point: >200°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - M225623

Carbapenem antibiotic. Antibacterial.

REFERENCES

• Adams, M.D., et al.: J. Bacteriol., 190, 8053 (2008)
• Pattanaik, P., et al.: J. Biol. Chem., 284, 945 (2008)
• Mendes, R., et al.: J. Antimicrob. Chemother., 63, 55 (2008)