(2R)-2-amino-3-({3-[4-(carboxymethoxy)-2,3-dichlorophenyl]-2-ethyl-3-oxopropyl}sulfanyl)propanoic acid

• ChemBase ID: 168201
• Molecular Formular: C16H19Cl2NO6S
• Molecular Mass: 424.29616
• Monoisotopic Mass: 423.03101369
• SMILES: c1c(c(c(c(c1)C(=O)C(CC)CSC[C@H](N)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)N
• InChI: InChI=1S/C16H19Cl2NO6S/c1-2-8(6-26-7-10(19)16(23)24)15(22)9-3-4-11(14(18)13(9)17)25-5-12(20)21/h3-4,8,10H,2,5-7,19H2,1H3,(H,20,21)(H,23,24)/t8?,10-/m0/s1
• InChIKey: MBVLLFXKDHUWAH-HTLJXXAVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-amino-3-({3-[4-(carboxymethoxy)-2,3-dichlorophenyl]-2-ethyl-3-oxopropyl}sulfanyl)propanoic acid
• IUPAC Traditional name: (2R)-2-amino-3-({3-[4-(carboxymethoxy)-2,3-dichlorophenyl]-2-ethyl-3-oxopropyl}sulfanyl)propanoic acid
• Synonyms: S-[2-[4-(Carboxymethoxy)-2,3-dichlorobenzoyl]butyl]-L-cysteine, Cysteine-ethacrynic Acid; Cysteine-ethacrynic Acid Adduct; Ethacrynic Acid-cysteine Complex; Ethacrynic Acid L-Cysteine Adduct

Database IDs

• CAS Number: 51246-37-8
• PubChem SID: 162262333
• PubChem CID: 71316436

CALCULATED PROPERTIES

• Acid pKa: 1.6437618
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): -2.1439366
• LogD (pH = 7.4): -3.0276856
• Log P: 0.30584386
• Molar Refractivity: 98.8578 cm^3
• Polarizability: 39.115875 Å^3
• Polar Surface Area: 126.92 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - E676010

A metabolite of Ethacrynic Acid (E676000) that is a potent 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)