2-(4-{[(3,5-dimethylphenyl)carbamoyl]methyl}phenoxy)-2-methylpropanoic acid

• ChemBase ID: 6098
• Molecular Formular: C20H23NO4
• Molecular Mass: 341.40092
• Monoisotopic Mass: 341.16270822
• SMILES: C(=O)(O)C(C)(C)Oc1ccc(cc1)CC(=O)Nc1cc(cc(c1)C)C
• Canonical SMILES: O=C(Nc1cc(C)cc(c1)C)Cc1ccc(cc1)OC(C(=O)O)(C)C
• InChI: InChI=1S/C20H23NO4/c1-13-9-14(2)11-16(10-13)21-18(22)12-15-5-7-17(8-6-15)25-20(3,4)19(23)24/h5-11H,12H2,1-4H3,(H,21,22)(H,23,24)
• InChIKey: BNFRJXLZYUTIII-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(4-{[(3,5-dimethylphenyl)carbamoyl]methyl}phenoxy)-2-methylpropanoic acid
• IUPAC Traditional name: efaproxiral
• Synonyms: 2-[4-[2-[(3,5-Dimethylphenyl)amino]-2-oxoethyl]phenoxy]-2-methylpropanoic Acid; RSR 13; Efaproxiral; 2-{4-[(3,5-DIMETHYLANILINO)-CARBONYL-METHYL]-PHENOXY}-2-METHYLPROPIONIC ACID

Database IDs

• CAS Number: 131179-95-8
• PubChem SID: 99444957; 160969523
• PubChem CID: 122335

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.561702
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 2.4616983
• LogD (pH = 7.4): 1.0379568
• Log P: 4.393981
• Molar Refractivity: 97.4803 cm^3
• Polarizability: 36.88254 Å^3
• Polar Surface Area: 75.63 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.12
• LOG S: -5.1
• Solubility (Water): 2.70e-03 g/l

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Off-White to Tan Solid
• Melting Point: 48-50°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

DrugBank - DB08486

Drug information: experimental

Toronto Research Chemicals - E415000

Allosteric modifier of hemoglobin (HB). Binds in the central water cavity of the Hb molecule causing a conformational change such that bound oxygen is released more readily. Antineoplastic adjunct (radiosensitizer).

REFERENCES

• Abraham, D.J., et al.: Biochemistry, 31, 9141 (1992)
• Pagel, P.S., et al.: J. Pharmacol. Exp. Ther., 285, 1 (1992)
• Kleinberg, L., et al.: J. Clin. Oncol., 17, 2593 (1992)