2-amino-2-{2-[4-(8-hydroxyoctyl)phenyl]ethyl}propane-1,3-diol hydrochloride

• ChemBase ID: 170205
• Molecular Formular: C19H34ClNO3
• Molecular Mass: 359.93116
• Monoisotopic Mass: 359.22272163
• SMILES: c1c(ccc(c1)CCCCCCCCO)CCC(N)(CO)CO.Cl
• Canonical SMILES: OCCCCCCCCc1ccc(cc1)CCC(CO)(CO)N.Cl
• InChI: InChI=1S/C19H33NO3.ClH/c20-19(15-22,16-23)13-12-18-10-8-17(9-11-18)7-5-3-1-2-4-6-14-21;/h8-11,21-23H,1-7,12-16,20H2;1H
• InChIKey: OFOJNDCKDFZROS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-2-{2-[4-(8-hydroxyoctyl)phenyl]ethyl}propane-1,3-diol hydrochloride
• IUPAC Traditional name: 2-amino-2-{2-[4-(8-hydroxyoctyl)phenyl]ethyl}propane-1,3-diol hydrochloride
• Synonyms: 2-Amino-2-(2-[4-(8-hydroxyoctyl)phenyl]ethyl)propane-1,3-diol Hydrochloride; ω-Hydroxy FTY720 Hydrochloride

Database IDs

• PubChem SID: 164226115
• PubChem CID: 71748861

CALCULATED PROPERTIES

• Acid pKa: 14.411364
• H Acceptors: 4
• H Donor: 4
• LogD (pH = 5.5): -0.35070774
• LogD (pH = 7.4): 0.67949617
• Log P: 2.6242993
• Molar Refractivity: 95.2087 cm^3
• Polarizability: 37.500275 Å^3
• Polar Surface Area: 86.71 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H825310

A metabolite of FTY720 (M12) (F805000); formed by ω-hydroxylation of very long-chain saturated fatty acid in human liver microsomes (HLM).

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)