2-hydroxy-N-(2-hydroxyethyl)-3-methoxy-5-(prop-2-en-1-yl)benzamide

• ChemBase ID: 73244
• Molecular Formular: C13H17NO4
• Molecular Mass: 251.27838
• Monoisotopic Mass: 251.11575803
• SMILES: c1c(c(c(cc1CC=C)C(=O)NCCO)O)OC
• Canonical SMILES: OCCNC(=O)c1cc(CC=C)cc(c1O)OC
• InChI: InChI=1S/C13H17NO4/c1-3-4-9-7-10(13(17)14-5-6-15)12(16)11(8-9)18-2/h3,7-8,15-16H,1,4-6H2,2H3,(H,14,17)
• InChIKey: UMJHTFHIQDEGKB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-hydroxy-N-(2-hydroxyethyl)-3-methoxy-5-(prop-2-en-1-yl)benzamide
• IUPAC Traditional name: 2-hydroxy-N-(2-hydroxyethyl)-3-methoxy-5-(prop-2-en-1-yl)benzamide
• Synonyms: Alibendol; 2-Hydroxy-N-(2-hydroxyethyl)-3-methoxy-5-(2-propen-1-yl)benzamide; 5-Allyl-2-hydroxy-N-(2-hydroxyethyl)-m-anisamide; Cebera; EB 1856; FC 54; H 3774

Database IDs

• CAS Number: 26750-81-2
• PubChem SID: 162038164
• PubChem CID: 71916

CALCULATED PROPERTIES

• Acid pKa: 8.699345
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 1.6445221
• LogD (pH = 7.4): 1.6236992
• Log P: 1.6447943
• Molar Refractivity: 69.0568 cm^3
• Polarizability: 25.89555 Å^3
• Polar Surface Area: 78.79 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: White Solid
• Melting Point: 97-99°C

Safety Information

• Storage Condition: -20°C; Refrigerator

Product Information

• Salt Data: Free Base

DETAILS

Selleck Chemicals - S1928

Research Area: Metabolic Disease
Biological Activity:

Toronto Research Chemicals - A535930

An amide analog of Eugenol, and is used therapeutically as an antispasmodic.

REFERENCES

• Marrero-Ponce, Y., et al.: Bioorg. Med. Chem., 14, 6502 (2006)