6-(3-phenylpropanamido)hexanoic acid

• ChemBase ID: 167550
• Molecular Formular: C15H21NO3
• Molecular Mass: 263.33214
• Monoisotopic Mass: 263.15214354
• SMILES: c1cccc(c1)CCC(=O)NCCCCCC(=O)O
• Canonical SMILES: O=C(CCc1ccccc1)NCCCCCC(=O)O
• InChI: InChI=1S/C15H21NO3/c17-14(11-10-13-7-3-1-4-8-13)16-12-6-2-5-9-15(18)19/h1,3-4,7-8H,2,5-6,9-12H2,(H,16,17)(H,18,19)
• InChIKey: ZIHJXSNRVVFXCZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-(3-phenylpropanamido)hexanoic acid
• IUPAC Traditional name: 6-(3-phenylpropanamido)hexanoic acid
• Synonyms: 6-[(1-Oxo-3-phenylpropyl)amino]hexanoic Acid; 6-[(3-Phenylpropanoyl)amino]hexanoic Acid; 6-[(3-Phenylpropionyl)amino]hexanoic Acid; N-Dihydrocinnamoylaminocaproic Acid

Database IDs

• CAS Number: 178622-38-3
• PubChem SID: 162261683
• PubChem CID: 4573507

CALCULATED PROPERTIES

• Acid pKa: 4.471866
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 1.2994117
• LogD (pH = 7.4): -0.46650237
• Log P: 2.3650908
• Molar Refractivity: 73.4265 cm^3
• Polarizability: 28.622763 Å^3
• Polar Surface Area: 66.4 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; DMF; Methanol
• Apperance: White Solid

DETAILS

Toronto Research Chemicals - D448800

N-Dihydrocinnamoylaminocaproic acid is used in the synthesis of a novel class of hedgehog antagonists derived from Cyclopamine (C988400).

REFERENCES

• Kumar, S., et al.: Bioorg. Med. Chem., 16, 2764 (2004)
• Nagata, R., et al.: J. Pharmacol., 55, 129 91991), Kubo, M., et al.: Cancer Res., 64, 6071 (2004)
• Dwyer, J., et al.: J. Biol. Chem., 282, 8959 (2004)