(2R)-2-[5-(dimethylamino)naphthalene-1-sulfonamido]-3-phenylpropanoic acid

• ChemBase ID: 165372
• Molecular Formular: C21H22N2O4S
• Molecular Mass: 398.47538
• Monoisotopic Mass: 398.13002819
• SMILES: c1cccc(c1)C[C@@H](NS(=O)(=O)c1c2c(ccc1)c(ccc2)N(C)C)C(=O)O
• Canonical SMILES: OC(=O)[C@H](NS(=O)(=O)c1cccc2c1cccc2N(C)C)Cc1ccccc1
• InChI: InChI=1S/C21H22N2O4S/c1-23(2)19-12-6-11-17-16(19)10-7-13-20(17)28(26,27)22-18(21(24)25)14-15-8-4-3-5-9-15/h3-13,18,22H,14H2,1-2H3,(H,24,25)/t18-/m1/s1
• InChIKey: GPIOGTIFRDHWSB-GOSISDBHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-[5-(dimethylamino)naphthalene-1-sulfonamido]-3-phenylpropanoic acid
• IUPAC Traditional name: (2R)-2-[5-(dimethylamino)naphthalene-1-sulfonamido]-3-phenylpropanoic acid
• Synonyms: N-[[5-(Dimethylamino)-1-naphthalenyl]sulfonyl]-D-phenylalanine; D-Dansylphenylalanine; Dansyl-(R)-phenylalanine; Dansyl-D-Phe; Dansyl-D-phenylalanine; N-Dansyl-D-phenylalanine; N-Dansyl-D-phenylalanine

Database IDs

• CAS Number: 56176-31-9
• PubChem SID: 162259505
• PubChem CID: 13734200

CALCULATED PROPERTIES

• Acid pKa: 3.4470248
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 1.5647538
• LogD (pH = 7.4): 0.2285311
• Log P: 2.2788696
• Molar Refractivity: 109.1889 cm^3
• Polarizability: 43.555206 Å^3
• Polar Surface Area: 86.71 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D180500

Used for the preparation of N-sulfonylamino acid derivatives as metalloproteinase inhibitors.

REFERENCES

• Reed, R., et al.: Biochem. J., 191, 867 (1980)
• Fehske, K., et al.: Biochem. Pharm., 30, 687 (1980)