(2S)-2-[5-(dimethylamino)naphthalene-1-sulfonamido]propanoic acid; cyclohexanamine

• ChemBase ID: 133252
• Molecular Formular: C21H31N3O4S
• Molecular Mass: 421.55354
• Monoisotopic Mass: 421.20352749
• SMILES: C[C@@H](C(=O)O)NS(=O)(=O)c1cccc2c1cccc2N(C)C.C1CCC(CC1)N
• Canonical SMILES: OC(=O)[C@@H](NS(=O)(=O)c1cccc2c1cccc2N(C)C)C.NC1CCCCC1
• InChI: InChI=1S/C15H18N2O4S.C6H13N/c1-10(15(18)19)16-22(20,21)14-9-5-6-11-12(14)7-4-8-13(11)17(2)3;7-6-4-2-1-3-5-6/h4-10,16H,1-3H3,(H,18,19);6H,1-5,7H2/t10-;/m0./s1
• InChIKey: CZUBQNQWSOLSJH-PPHPATTJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-[5-(dimethylamino)naphthalene-1-sulfonamido]propanoic acid; cyclohexanamine
• IUPAC Traditional name: (2S)-2-[5-(dimethylamino)naphthalene-1-sulfonamido]propanoic acid; cyclohexylamine
• Synonyms: N-[[5-(Dimethylamino)-1-naphthalenyl]sulfonyl]- L-alanine cyclohexylammonium salt; Dansyl-L-alanine cyclohexylammonium salt

Database IDs

• CAS Number: 53332-27-7
• EC Number: 258-478-3
• MDL Number: MFCD00038927
• PubChem SID: 162227529
• PubChem CID: 6452802

CALCULATED PROPERTIES

• Acid pKa: 3.273566
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -0.25290018
• LogD (pH = 7.4): -1.472213
• Log P: 0.4901095
• Molar Refractivity: 84.5699 cm^3
• Polarizability: 33.97037 Å^3
• Polar Surface Area: 86.71 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• German water hazard class: 3
• Storage Temperature: -20°C

DETAILS

Sigma Aldrich - D0125

Application
Alanine conjugated to the fluorophore 5-(dimethylamino)naphthalene-1-sulfonyl (dansyl). The unnatural amino acid has been incorporated into expressed proteins by use of a mutated aminoacyl-tRNA synthetase specific for dansylalanine.1,2