2-{4-[3-amino-4-hydroxy-3-(hydroxymethyl)butyl]phenyl}acetic acid hydrochloride

• ChemBase ID: 169477
• Molecular Formular: C13H20ClNO4
• Molecular Mass: 289.7552
• Monoisotopic Mass: 289.10808581
• SMILES: c1c(ccc(c1)CC(=O)O)CCC(N)(CO)CO.Cl
• Canonical SMILES: OCC(CCc1ccc(cc1)CC(=O)O)(CO)N.Cl
• InChI: InChI=1S/C13H19NO4.ClH/c14-13(8-15,9-16)6-5-10-1-3-11(4-2-10)7-12(17)18;/h1-4,15-16H,5-9,14H2,(H,17,18);1H
• InChIKey: SBZJCQIDSYQGIU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-{4-[3-amino-4-hydroxy-3-(hydroxymethyl)butyl]phenyl}acetic acid hydrochloride
• IUPAC Traditional name: {4-[3-amino-4-hydroxy-3-(hydroxymethyl)butyl]phenyl}acetic acid hydrochloride
• Synonyms: 4-[3-Amino-4-hydroxy-3-(hydroxymethyl)butyl]benzeneacetic Acid Hydrochloride; FTY720 Acetic Acid Hydrochloride

Database IDs

• PubChem SID: 162263609
• PubChem CID: 71316989

CALCULATED PROPERTIES

• Acid pKa: 3.9767594
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): -2.1996248
• LogD (pH = 7.4): -2.1933908
• Log P: -2.1910079
• Molar Refractivity: 67.3394 cm^3
• Polarizability: 26.437946 Å^3
• Polar Surface Area: 103.78 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - F805015

A metabolite of FTY720 (M4) (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)