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

• ChemBase ID: 168166
• Molecular Formular: C22H23N3Na2O7S
• Molecular Mass: 519.47846
• Monoisotopic Mass: 519.10520965
• SMILES: N12[C@H]([C@H](C(=C1C(=O)[O-])S[C@@H]1CN[C@@H](C1)C(=O)Nc1cc(ccc1)C(=O)[O-])C)[C@H](C2=O)[C@H](O)C.[Na+].[Na+]
• Canonical SMILES: O=C([C@H]1NC[C@H](C1)SC1=C(C(=O)[O-])N2[C@H]([C@H]1C)[C@H](C2=O)[C@H](O)C)Nc1cccc(c1)C(=O)[O-].[Na+].[Na+]
• InChI: InChI=1S/C22H25N3O7S.2Na/c1-9-16-15(10(2)26)20(28)25(16)17(22(31)32)18(9)33-13-7-14(23-8-13)19(27)24-12-5-3-4-11(6-12)21(29)30;;/h3-6,9-10,13-16,23,26H,7-8H2,1-2H3,(H,24,27)(H,29,30)(H,31,32);;/q;2*+1/p-2/t9-,10-,13+,14+,15-,16-;;/m1../s1
• InChIKey: KMVRATCHVMUJHM-SHZCTIMHSA-L

NAMES AND DATABASE IDS

Names

• IUPAC name: disodium (4R,5S,6S)-3-{[(3S,5S)-5-[(3-carboxylatophenyl)carbamoyl]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: disodium (4R,5S,6S)-3-{[(3S,5S)-5-[(3-carboxylatophenyl)carbamoyl]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-[[(3-Carboxyphenyl)amino]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; L 749; Ertapenem Disodium (85%)

Database IDs

• CAS Number: 153832-38-3
• PubChem SID: 162262298
• PubChem CID: 150611

CALCULATED PROPERTIES

• Polarizability: 45.937515 Å^3
• Polar Surface Area: 161.93 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false
• Acid pKa: 3.3674526
• H Acceptors: 8
• H Donor: 3
• LogD (pH = 5.5): -4.364522
• LogD (pH = 7.4): -6.0415206
• Log P: -3.2123687
• Molar Refractivity: 143.4783 cm^3

PROPERTIES

Physical Property

• Solubility: DMSO; Water
• Apperance: Pale Yellow Solid
• Melting Point: 230-234°C (dec.)

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - E635000

Group 1 carbapenem antibiotic. An antibacterial.

REFERENCES

• Sundelof, J.G., et al.: Antimicrob. Agents Chemother., 41, 1743 (1997)