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

• ChemBase ID: 163697
• Molecular Formular: C22H27N3O8S
• Molecular Mass: 493.53008
• Monoisotopic Mass: 493.15188584
• SMILES: N1=C(C([C@@H](C1[C@H]([C@H](O)C)C(=O)O)C)S[C@@H]1CN[C@@H](C1)C(=O)Nc1cc(ccc1)C(=O)O)C(=O)O
• Canonical SMILES: O=C([C@H]1NC[C@H](C1)SC1C(=NC([C@H]1C)[C@@H](C(=O)O)[C@H](O)C)C(=O)O)Nc1cccc(c1)C(=O)O
• InChI: InChI=1S/C22H27N3O8S/c1-9-16(15(10(2)26)21(30)31)25-17(22(32)33)18(9)34-13-7-14(23-8-13)19(27)24-12-5-3-4-11(6-12)20(28)29/h3-6,9-10,13-16,18,23,26H,7-8H2,1-2H3,(H,24,27)(H,28,29)(H,30,31)(H,32,33)/t9-,10-,13+,14+,15+,16?,18?/m1/s1
• InChIKey: MLCVCXYVRPDWBV-CLBDNALYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R)-2-[(1R,2R)-1-carboxy-2-hydroxypropyl]-4-{[(3S,5S)-5-[(3-carboxyphenyl)carbamoyl]pyrrolidin-3-yl]sulfanyl}-3-methyl-3,4-dihydro-2H-pyrrole-5-carboxylic acid
• IUPAC Traditional name: (4R)-5-[(1R,2R)-1-carboxy-2-hydroxypropyl]-3-{[(3S,5S)-5-[(3-carboxyphenyl)carbamoyl]pyrrolidin-3-yl]sulfanyl}-4-methyl-4,5-dihydro-3H-pyrrole-2-carboxylic acid
• Synonyms: (αS,2S,3R)-5-Carboxy-4-[[(3S,5S)-5-[[(3-carboxyphenyl)amino]carbonyl]-3-pyrrolidinyl]thio]-3,4-dihydro-α-[(1R)-1-hydroxyethyl]-3-methyl-2H-pyrrole-2-acetic Acid

Database IDs

• CAS Number: 1150883-75-2
• PubChem SID: 162257832
• PubChem CID: 71314524

CALCULATED PROPERTIES

• Acid pKa: 3.1516864
• H Acceptors: 10
• H Donor: 6
• LogD (pH = 5.5): -4.4626703
• LogD (pH = 7.4): -7.7900805
• Log P: -1.7660823
• Molar Refractivity: 122.5338 cm^3
• Polarizability: 47.186596 Å^3
• Polar Surface Area: 185.62 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - C177870

(αS,2S,3R)-5-Carboxy-4-[[(3S,5S)-5-[[(3-carboxyphenyl)amino]carbonyl]-3-pyrrolidinyl]thio]-3,4-dihydro-α-[(1R)-1-hydroxyethyl]-3-methyl-2H-pyrrole-2-acetic Acid is an impurity of Ertapenem (E635000).