(2E)-but-2-enedioic acid; (2R)-2-{2-[(1S)-1-(4-chlorophenyl)-1-(2H5)phenylethoxy]ethyl}-1-methylpyrrolidine

• ChemBase ID: 164823
• Molecular Formular: C25H30ClNO5
• Molecular Mass: 459.9624
• Monoisotopic Mass: 459.18125075
• SMILES: C1C[C@@H](N(C1)C)CCOC(c1ccc(cc1)Cl)(C)c1ccccc1.C(=C\C(=O)O)/C(=O)O
• Canonical SMILES: Clc1ccc(cc1)C(c1ccccc1)(OCC[C@H]1CCCN1C)C.OC(=O)/C=C/C(=O)O
• InChI: InChI=1S/C21H26ClNO.C4H4O4/c1-21(17-7-4-3-5-8-17,18-10-12-19(22)13-11-18)24-16-14-20-9-6-15-23(20)2;5-3(6)1-2-4(7)8/h3-5,7-8,10-13,20H,6,9,14-16H2,1-2H3;1-2H,(H,5,6)(H,7,8)/b;2-1+/t20-,21-;/m1./s1
• InChIKey: PMGQWSIVQFOFOQ-YKVZVUFRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2E)-but-2-enedioic acid; (2R)-2-{2-[(1S)-1-(4-chlorophenyl)-1-(^2H₅)phenylethoxy]ethyl}-1-methylpyrrolidine
• IUPAC Traditional name: (2R)-2-{2-[(1S)-1-(4-chlorophenyl)-1-(^2H₅)phenylethoxy]ethyl}-1-methylpyrrolidine; fumaric acid
• Synonyms: (2R,3Z,5R)-3-(2-Hydroxyethylidene)-7-oxo-4-oxa-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid Methyl-d3 Ester; [2R-(2α,3Z,5α)]- 3-(2-Hydroxyethylidene)-7-oxo-4-oxa-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid Methyl-d3 Ester; Methyl-d3 Clavulanate; Clavulanic Acid Methyl-d3 Ester

Database IDs

• PubChem SID: 162258957
• PubChem CID: 71314889

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 1.5297673
• LogD (pH = 7.4): 2.7880056
• Log P: 4.923333
• Molar Refractivity: 101.6476 cm^3
• Polarizability: 39.87842 Å^3
• Polar Surface Area: 12.47 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - C563772

Labelled Clavulanic Acid Methyl Ester (C563770). Clavulanic Acid Methyl Ester is a substituted Clavulanic acid (C563750) as β-lactamase inhibitor.

REFERENCES

• Reading, C., et al.: J. Enzyme Inhibition, 1, 83 (1986)