4-{4-[3-amino-4-hydroxy-3-(hydroxymethyl)butyl]phenyl}butanoic acid hydrochloride

• ChemBase ID: 169479
• Molecular Formular: C15H24ClNO4
• Molecular Mass: 317.80836
• Monoisotopic Mass: 317.13938593
• SMILES: c1c(ccc(c1)CCCC(=O)O)CCC(N)(CO)CO.Cl
• Canonical SMILES: OCC(CCc1ccc(cc1)CCCC(=O)O)(CO)N.Cl
• InChI: InChI=1S/C15H23NO4.ClH/c16-15(10-17,11-18)9-8-13-6-4-12(5-7-13)2-1-3-14(19)20;/h4-7,17-18H,1-3,8-11,16H2,(H,19,20);1H
• InChIKey: RIUMQYSOPOCQNO-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-{4-[3-amino-4-hydroxy-3-(hydroxymethyl)butyl]phenyl}butanoic acid hydrochloride
• IUPAC Traditional name: 4-{4-[3-amino-4-hydroxy-3-(hydroxymethyl)butyl]phenyl}butanoic acid hydrochloride
• Synonyms: 4-[3-Amino-4-hydroxy-3-(hydroxymethyl)butyl]benzenebutanoic Acid Hydrochloride; FTY720 Butanoic Acid Hydrochloride

Database IDs

• CAS Number: 896472-93-8
• PubChem SID: 162263611
• PubChem CID: 71316993

CALCULATED PROPERTIES

• Acid pKa: 4.384936
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): -1.3258686
• LogD (pH = 7.4): -1.3039732
• Log P: -1.30191
• Molar Refractivity: 76.5414 cm^3
• Polarizability: 30.11098 Å^3
• Polar Surface Area: 103.78 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - F805025

A metabolite of FTY720 (M3) (F805000).

REFERENCES

• Billich, A., et al.: J. Biol. Chem., 278, 47408 (2003)
• Bjornsson, T.D., Drug Metab. Dispos., 31, 815 (2003)
• Albert, R., et al.: J. Med. Chem., 48, 5373 (2003)