5-[(2R)-2-{[3-(2-ethoxyphenoxy)propyl]amino}propyl]-2-methoxybenzene-1-sulfonamide

• ChemBase ID: 169944
• Molecular Formular: C21H30N2O5S
• Molecular Mass: 422.5383
• Monoisotopic Mass: 422.18754307
• SMILES: c1c(c(ccc1C[C@H](NCCCOc1c(cccc1)OCC)C)OC)S(=O)(=O)N
• Canonical SMILES: CCOc1ccccc1OCCCN[C@@H](Cc1ccc(c(c1)S(=O)(=O)N)OC)C
• InChI: InChI=1S/C21H30N2O5S/c1-4-27-18-8-5-6-9-19(18)28-13-7-12-23-16(2)14-17-10-11-20(26-3)21(15-17)29(22,24)25/h5-6,8-11,15-16,23H,4,7,12-14H2,1-3H3,(H2,22,24,25)/t16-/m1/s1
• InChIKey: SQOCZDWIAGIVEA-MRXNPFEDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-[(2R)-2-{[3-(2-ethoxyphenoxy)propyl]amino}propyl]-2-methoxybenzene-1-sulfonamide
• IUPAC Traditional name: 5-[(2R)-2-{[3-(2-ethoxyphenoxy)propyl]amino}propyl]-2-methoxybenzenesulfonamide
• Synonyms: (R)-5-[2-[(3-(2-Ethoxyphenoxy)propyl)amino]-2-methylethyl]-2-methoxybenzene-sulfonamide; AB289; 5-[(2R)-2-[[3-(2-Ethoxyphenoxy)propyl]amino]propyl]-2-methoxybenzenesulfonamide; Homo Tamsulosin

Database IDs

• CAS Number: 1217771-89-5
• PubChem SID: 162264076
• PubChem CID: 29981057

CALCULATED PROPERTIES

• Acid pKa: 9.4203615
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): -0.615448
• LogD (pH = 7.4): 0.26255205
• Log P: 2.0033293
• Molar Refractivity: 113.7303 cm^3
• Polarizability: 45.258278 Å^3
• Polar Surface Area: 99.88 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H653500

An analog of Tamsulosin.

REFERENCES

• Litchfield, J.T., et al.: J. Pharmacol. Exp. Ther., 96, 99 (1949)
• Greenwood, D.T., et al.: J. Med. Chem., 18, 573 (1949)