sodium (4R,5S,6S)-3-{[(3S,5S)-5-(dimethylcarbamoyl)pyrrolidin-3-yl]sulfanyl}-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

• ChemBase ID: 172688
• Molecular Formular: C17H24N3NaO5S
• Molecular Mass: 405.44433
• Monoisotopic Mass: 405.13343616
• 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.[Na+]
• 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.[Na+]
• InChI: InChI=1S/C17H25N3O5S.Na/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);/q;+1/p-1/t7-,8-,9+,10+,11-,12-;/m1./s1
• InChIKey: UBQRNADYCUXRBD-NACOAMSHSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (4R,5S,6S)-3-{[(3S,5S)-5-(dimethylcarbamoyl)pyrrolidin-3-yl]sulfanyl}-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
• IUPAC Traditional name: sodium (4R,5S,6S)-3-{[(3S,5S)-5-(dimethylcarbamoyl)pyrrolidin-3-yl]sulfanyl}-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
• Synonyms: (4R,5S,6S)-3-[[3S,5S)-5-[(Dimethylamino)carbonyl]-3-pyrrolidinyl]thio]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic Acid Sodium Salt; Meropenem Sodium Salt

Database IDs

• CAS Number: 211238-34-5
• PubChem SID: 164228598
• PubChem CID: 23718739

CALCULATED PROPERTIES

• Acid pKa: 3.4704194
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): -4.3561654
• LogD (pH = 7.4): -4.3568015
• Log P: -4.353987
• Molar Refractivity: 108.7233 cm^3
• Polarizability: 37.762764 Å^3
• Polar Surface Area: 113.01 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Water
• Apperance: Pale Yellow Solid
• Melting Point: >170°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - M225620

Carbapenem antibiotic. Antibacterial.

REFERENCES

• Sunagawa, M., et al.: J. Antibiot., 43, 519 (1990)
• Hurst, M., et al.: Drugs, 59, 653 (1990)