(3R,4S)-2-[(1S,2R)-1-carboxy-2-hydroxypropyl]-4-{[(3S,5S)-5-(dimethylcarbamoyl)pyrrolidin-3-yl]sulfanyl}-3-methyl-3,4-dihydro-2H-pyrrole-5-carboxylic acid; (4R)-5-[(1S,2R)-1-carboxy-2-hydroxypropyl]-3-{[(3S,5S)-5-(dimethylcarbamoyl)pyrrolidin-3-yl]sulfanyl}-4-methyl-4,5-dihydro-1H-pyrrole-2-carboxylic acid

• ChemBase ID: 179644
• Molecular Formular: C34H54N6O12S2
• Molecular Mass: 802.95556
• Monoisotopic Mass: 802.3241132
• SMILES: N1=C([C@H]([C@@H](C1[C@@H]([C@H](O)C)C(=O)O)C)S[C@@H]1CN[C@@H](C1)C(=O)N(C)C)C(=O)O.N1C(=C([C@@H](C1[C@@H]([C@H](O)C)C(=O)O)C)S[C@@H]1CN[C@@H](C1)C(=O)N(C)C)C(=O)O
• Canonical SMILES: O=C([C@H]1NC[C@H](C1)SC1=C(NC([C@H]1C)[C@H](C(=O)O)[C@H](O)C)C(=O)O)N(C)C.O=C([C@H]1NC[C@H](C1)S[C@H]1[C@H](C)C(N=C1C(=O)O)[C@H](C(=O)O)[C@H](O)C)N(C)C
• InChI: InChI=1S/2C17H27N3O6S/c2*1-7-12(11(8(2)21)16(23)24)19-13(17(25)26)14(7)27-9-5-10(18-6-9)15(22)20(3)4/h7-12,18-19,21H,5-6H2,1-4H3,(H,23,24)(H,25,26);7-12,14,18,21H,5-6H2,1-4H3,(H,23,24)(H,25,26)/t7-,8-,9+,10+,11-,12?;7-,8-,9+,10+,11-,12?,14+/m11/s1
• InChIKey: CZRMYGNALAXOKS-RJMJPBFUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R,4S)-2-[(1S,2R)-1-carboxy-2-hydroxypropyl]-4-{[(3S,5S)-5-(dimethylcarbamoyl)pyrrolidin-3-yl]sulfanyl}-3-methyl-3,4-dihydro-2H-pyrrole-5-carboxylic acid; (4R)-5-[(1S,2R)-1-carboxy-2-hydroxypropyl]-3-{[(3S,5S)-5-(dimethylcarbamoyl)pyrrolidin-3-yl]sulfanyl}-4-methyl-4,5-dihydro-1H-pyrrole-2-carboxylic acid
• IUPAC Traditional name: (3S,4R)-5-[(1S,2R)-1-carboxy-2-hydroxypropyl]-3-{[(3S,5S)-5-(dimethylcarbamoyl)pyrrolidin-3-yl]sulfanyl}-4-methyl-4,5-dihydro-3H-pyrrole-2-carboxylic acid; (4R)-5-[(1S,2R)-1-carboxy-2-hydroxypropyl]-3-{[(3S,5S)-5-(dimethylcarbamoyl)pyrrolidin-3-yl]sulfanyl}-4-methyl-4,5-dihydro-1H-pyrrole-2-carboxylic acid
• Synonyms: (αS,2S,3R,4S)-5-Carboxy-4-[[(3S,5S)-5-[(dimethylamino)carbonyl]-3-pyrrolidinyl]thio]-3,4-dihydro-α-[(1R)-hydroxyethyl]-3-methyl-2H-pyrrole-2-acetic Acid; H 4295; ICI 213689; UK 1a; ZM 213689 (Meropenem impurity)(Mixture of double bond isomers)

Database IDs

• PubChem SID: 164235554
• PubChem CID: 71753023

CALCULATED PROPERTIES

• Acid pKa: 3.2039967
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -4.399915
• LogD (pH = 7.4): -6.05493
• Log P: -3.2151482
• Molar Refractivity: 98.6159 cm^3
• Polarizability: 38.92072 Å^3
• Polar Surface Area: 139.53 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - Z486500

The major metabolite of Meropenem (M225620) - a carbapenem antibiotic - in plasma and urine. This metabolite existed as a mixture of 1-pyrroline and its 2-pyrroline isomer, and the coexistence of the two isomers at equilibrium in aqueous solutions was obs

REFERENCES

• Takeuchi, Y., et al.: J. Antibiotics, 46, 827 (1993)
• Wiseman, L., et al.: Drugs, 50, 73 (1993)
• Valtonen, M., et al.: J. Antimicrob. Chemother., 45, 701 (1993)