(4R,5S,6S)-3-{[(3S,5S)-5-[(3-carboxyphenyl)carbamoyl]-1-[(4R,5S,6S)-3-{[(3S,5S)-5-[(3-carboxyphenyl)carbamoyl]pyrrolidin-3-yl]sulfanyl}-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carbonyl]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: 168168
• Molecular Formular: C44H48N6O13S2
• Molecular Mass: 933.01432
• Monoisotopic Mass: 932.27207763
• SMILES: [C@@H]12N(C(=C([C@@H]1C)S[C@H]1C[C@H](NC1)C(=O)Nc1cc(ccc1)C(=O)O)C(=O)N1C[C@H](C[C@H]1C(=O)Nc1cc(ccc1)C(=O)O)SC1=C(N3[C@H]([C@H]1C)[C@H](C3=O)[C@H](O)C)C(=O)O)C(=O)[C@@H]2[C@H](O)C
• Canonical SMILES: C[C@H]([C@H]1C(=O)N2[C@@H]1[C@@H](C)C(=C2C(=O)N1C[C@H](C[C@H]1C(=O)Nc1cccc(c1)C(=O)O)SC1=C(C(=O)O)N2[C@H]([C@H]1C)[C@H](C2=O)[C@H](O)C)S[C@@H]1CN[C@@H](C1)C(=O)Nc1cccc(c1)C(=O)O)O
• InChI: InChI=1S/C44H48N6O13S2/c1-17-31-29(19(3)51)39(55)49(31)33(35(17)64-25-13-27(45-15-25)37(53)46-23-9-5-7-21(11-23)42(58)59)41(57)48-16-26(14-28(48)38(54)47-24-10-6-8-22(12-24)43(60)61)65-36-18(2)32-30(20(4)52)40(56)50(32)34(36)44(62)63/h5-12,17-20,25-32,45,51-52H,13-16H2,1-4H3,(H,46,53)(H,47,54)(H,58,59)(H,60,61)(H,62,63)/t17-,18-,19-,20-,25+,26+,27+,28+,29-,30-,31-,32-/m1/s1
• InChIKey: GIKZHKCNSVCAIT-BNCIILEKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R,5S,6S)-3-{[(3S,5S)-5-[(3-carboxyphenyl)carbamoyl]-1-[(4R,5S,6S)-3-{[(3S,5S)-5-[(3-carboxyphenyl)carbamoyl]pyrrolidin-3-yl]sulfanyl}-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carbonyl]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-[(3-carboxyphenyl)carbamoyl]-1-[(4R,5S,6S)-3-{[(3S,5S)-5-[(3-carboxyphenyl)carbamoyl]pyrrolidin-3-yl]sulfanyl}-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carbonyl]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-[[(3-Carboxyphenyl)amino]carbonyl]-1-[[(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-en-2-yl]carbonyl]-3-pyrrolidinyl]thio]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic Acid; Ertapenem Dimer Impurity

Database IDs

• CAS Number: 402955-37-7
• PubChem SID: 162262300
• PubChem CID: 71316412

CALCULATED PROPERTIES

• Lipinski's Rule of Five: false
• Acid pKa: 3.183702
• H Acceptors: 14
• H Donor: 8
• LogD (pH = 5.5): -6.4982867
• LogD (pH = 7.4): -9.835046
• Log P: -3.8405404
• Molar Refractivity: 240.5304 cm^3
• Polarizability: 90.70814 Å^3
• Polar Surface Area: 283.52 Å^2
• Rotatable Bonds: 14

DETAILS

Toronto Research Chemicals - E635015

Ertapenem Dimer is an impurity of Ertapenem (E635000).

REFERENCES

• Smith, G., et al.: J. Pharm. Sci., 79, 732 (1990)
• Mendez, R., et al.: J .Chem. Pharm. Bull., 40, 2044 (1990)
• Takeuchi, Y., et al.: J. Antibiot., 46, 827 (1990)
• Kohler, J., et al.: Antimicrob. Agents Chemother., 43, 1170 (1990)