2-{2,3-dichloro-4-[2-methylidene(2H5)butanoyl]phenoxy}acetic acid

• ChemBase ID: 168200
• Molecular Formular: C13H12Cl2O4
• Molecular Mass: 303.13798
• Monoisotopic Mass: 302.01126422
• SMILES: c1c(c(c(c(c1)C(=O)C(=C)CC)Cl)Cl)OCC(=O)O
• Canonical SMILES: CCC(=C)C(=O)c1ccc(c(c1Cl)Cl)OCC(=O)O
• InChI: InChI=1S/C13H12Cl2O4/c1-3-7(2)13(18)8-4-5-9(12(15)11(8)14)19-6-10(16)17/h4-5H,2-3,6H2,1H3,(H,16,17)
• InChIKey: AVOLMBLBETYQHX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-{2,3-dichloro-4-[2-methylidene(^2H₅)butanoyl]phenoxy}acetic acid
• IUPAC Traditional name: 2,3-dichloro-4-[2-methylidene(^2H₅)butanoyl]phenoxyacetic acid
• Synonyms: 2-[2,3-Dichloro-4-(2-methylene-1-oxobutyl)phenoxy-d5]acetic Acid; [4-(2-Methylenebutyryl)-2,3-dichlorophenoxy-d5]acetic Acid; Crinuril-d5; Edecril-d5; Edecrin-d5; Edecrina-d5; Endecril-d5; Etacrynic Acid-d5; Etakrinic Acid-d5; Hidromedin-d5; Hydromedin-d5; MK 595-d5; Mingit-d5; NSC 624008-d5; NSC 85791-d5; Otacril-d5; Reomax-d5; Taladren-d5; Uregit-d5; Ethacrynic Acid-d5

Database IDs

• PubChem SID: 162262332
• PubChem CID: 71316435

CALCULATED PROPERTIES

• Acid pKa: 2.796934
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 1.0121546
• LogD (pH = 7.4): 0.16142255
• Log P: 3.655707
• Molar Refractivity: 72.224 cm^3
• Polarizability: 28.14986 Å^3
• Polar Surface Area: 63.6 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - E676002

Labelled Ethacrynic Acid (E676000). Diuretic.

REFERENCES

• Beyer, et al.: J. Pharmacol. Exp. Ther., 147, 1 (1965)
• Kim., et al.: Am. J. Cardiol., 27, 407 (1965)
• Williamson, H.E., et al.: J. Clin. Pharmacol., 17, 663 (1965)