(2S)-3-({3-[4-(carboxymethoxy)-2,3-dichlorophenyl]-2-ethyl-3-oxopropyl}sulfanyl)-2-acetamidopropanoic acid

• ChemBase ID: 168202
• Molecular Formular: C18H21Cl2NO7S
• Molecular Mass: 466.33284
• Monoisotopic Mass: 465.04157838
• SMILES: c1c(c(c(c(c1)C(=O)C(CC)CSC[C@@H](NC(=O)C)C(=O)O)Cl)Cl)OCC(=O)O
• Canonical SMILES: CCC(C(=O)c1ccc(c(c1Cl)Cl)OCC(=O)O)CSC[C@H](C(=O)O)NC(=O)C
• InChI: InChI=1S/C18H21Cl2NO7S/c1-3-10(7-29-8-12(18(26)27)21-9(2)22)17(25)11-4-5-13(16(20)15(11)19)28-6-14(23)24/h4-5,10,12H,3,6-8H2,1-2H3,(H,21,22)(H,23,24)(H,26,27)/t10?,12-/m1/s1
• InChIKey: FFUBZDLDJQLBLZ-TVKKRMFBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-3-({3-[4-(carboxymethoxy)-2,3-dichlorophenyl]-2-ethyl-3-oxopropyl}sulfanyl)-2-acetamidopropanoic acid
• IUPAC Traditional name: (2S)-3-({3-[4-(carboxymethoxy)-2,3-dichlorophenyl]-2-ethyl-3-oxopropyl}sulfanyl)-2-acetamidopropanoic acid
• Synonyms: N-Acetyl-S-[2-[4-(carboxymethoxy)-2,3-dichlorobenzoyl]butyl]-L-cysteine; Ethacrynic Acid Mercapturate

Database IDs

• CAS Number: 54546-23-5
• PubChem SID: 162262334
• PubChem CID: 71316437

CALCULATED PROPERTIES

• Acid pKa: 2.7019665
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): -2.132765
• LogD (pH = 7.4): -4.3270845
• Log P: 2.5571098
• Molar Refractivity: 108.3016 cm^3
• Polarizability: 42.544277 Å^3
• Polar Surface Area: 130.0 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - E676020

A metabolite of Ethacrynic Acid (E676000) that is an inhibitor of sodium-potassium-dichloride cotransport and bumetanide binding. Also an inhibitor of human hepatic glutathione S-transferase isozymes.

REFERENCES

• Palfrey, H. et al.: Am. J. Physiol., 264, C1270 (1993)
• Klaassen, C.D. et al.: J. Pharmacol. Exp. Therap., 191, 548(1993)
• Takamatsu, Y. et al.: Toxicol. Lett., 62, 241 (1993)