5-butanamido-2-hydroxybenzoic acid

• ChemBase ID: 163495
• Molecular Formular: C11H13NO4
• Molecular Mass: 223.22522
• Monoisotopic Mass: 223.0844579
• SMILES: c1c(ccc(c1C(=O)O)O)NC(=O)CCC
• Canonical SMILES: CCCC(=O)Nc1ccc(c(c1)C(=O)O)O
• InChI: InChI=1S/C11H13NO4/c1-2-3-10(14)12-7-4-5-9(13)8(6-7)11(15)16/h4-6,13H,2-3H2,1H3,(H,12,14)(H,15,16)
• InChIKey: WVUWWPZYZLFNQU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-butanamido-2-hydroxybenzoic acid
• IUPAC Traditional name: 5-butanamido-2-hydroxybenzoic acid
• Synonyms: 2-Hydroxy-5-[(1-oxobutyl)amino]benzoic Acid; N-Butyryl-5-ASA; N-Butyryl Mesalazine

Database IDs

• CAS Number: 93968-81-1
• PubChem SID: 162257630
• PubChem CID: 24284496

CALCULATED PROPERTIES

• Acid pKa: 2.6152651
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -0.4365183
• LogD (pH = 7.4): -1.1459148
• Log P: 2.3600783
• Molar Refractivity: 59.386 cm^3
• Polarizability: 21.884243 Å^3
• Polar Surface Area: 86.63 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - B693800

A metabolite of Mesalazine (M258100).

REFERENCES

• Allgayer, H., et al.: Arzneim.-Forsch., 35, 1457 (1985)
• Cui, F., et al.: J. Pharm. Biomed. Anal., 34, 189 (1985)