propan-2-yl 4-(2-chlorophenyl)-1-ethyl-2-methyl-5-oxo-1H,4H,5H,7H-furo[3,4-b]pyridine-3-carboxylate

• ChemBase ID: 153990
• Molecular Formular: C20H22ClNO4
• Molecular Mass: 375.84598
• Monoisotopic Mass: 375.12373587
• SMILES: CCN1C(=C(C(C2=C1COC2=O)c1ccccc1Cl)C(=O)OC(C)C)C
• Canonical SMILES: CCN1C(=C(C(=O)OC(C)C)C(C2=C1COC2=O)c1ccccc1Cl)C
• InChI: InChI=1S/C20H22ClNO4/c1-5-22-12(4)16(20(24)26-11(2)3)17(13-8-6-7-9-14(13)21)18-15(22)10-25-19(18)23/h6-9,11,17H,5,10H2,1-4H3
• InChIKey: NPUSXSOBPNHOPH-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: propan-2-yl 4-(2-chlorophenyl)-1-ethyl-2-methyl-5-oxo-1H,4H,5H,7H-furo[3,4-b]pyridine-3-carboxylate
• IUPAC Traditional name: isopropyl 4-(2-chlorophenyl)-1-ethyl-2-methyl-5-oxo-4H,7H-furo[3,4-b]pyridine-3-carboxylate
• Synonyms: 4-(2-Chlorophenyl)-1-ethyl-2-methyl-5-oxo-1,4,5,7-tetrahydrofuro[3,4-b]pyridine-3-carboxylic acid isopropyl ester; BAY R3401

Database IDs

• CAS Number: 100276-03-7
• MDL Number: MFCD08705409
• PubChem SID: 24891741; 162248129
• PubChem CID: 9842599

CALCULATED PROPERTIES

• Acid pKa: 14.90389
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 3.4446347
• LogD (pH = 7.4): 3.4642055
• Log P: 3.4644608
• Molar Refractivity: 102.1379 cm^3
• Polarizability: 38.72693 Å^3
• Polar Surface Area: 55.84 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: soluble15 mg/mL
• Apperance: white solid

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C20H22ClNO4

DETAILS

Sigma Aldrich - B3936

Packaging
Light sensitive; store in amber vials.
Biochem/physiol Actions
BAY R3401 is a glycogen phosphorylase inhibitor. The racemic prodrug, BAY R3401, suppresses hepatic glycogenolysis. BAY W1807, the active metabolite of BAY R3401, inhibits muscle glycogen phosphorylase a and b. It has been investigated that the metabolites of BAY R3401 suppress hepatic glycogenolysis by allosteric inhibition and dephosphorylation of phosphorylase a.