[(3S)-3-amino-3-[(3-hexylphenyl)carbamoyl]propyl]phosphonic acid hydrobromide

• ChemBase ID: 160162
• Molecular Formular: C16H28BrN2O4P
• Molecular Mass: 423.282281
• Monoisotopic Mass: 422.09700602
• SMILES: c1(cccc(c1)CCCCCC)NC(=O)[C@H](CCP(=O)(O)O)N.Br
• Canonical SMILES: CCCCCCc1cccc(c1)NC(=O)[C@H](CCP(=O)(O)O)N.Br
• InChI: InChI=1S/C16H27N2O4P.BrH/c1-2-3-4-5-7-13-8-6-9-14(12-13)18-16(19)15(17)10-11-23(20,21)22;/h6,8-9,12,15H,2-5,7,10-11,17H2,1H3,(H,18,19)(H2,20,21,22);1H/t15-;/m0./s1
• InChIKey: PIGJYNCMLIOKSN-RSAXXLAASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(3S)-3-amino-3-[(3-hexylphenyl)carbamoyl]propyl]phosphonic acid hydrobromide
• IUPAC Traditional name: (3S)-3-amino-3-[(3-hexylphenyl)carbamoyl]propylphosphonic acid hydrobromide
• Synonyms: (S)-W-146 Hydrobromide; [(3S)-3-Amino-4-[(3-hexylphenyl)amino]-4-oxobutyl]phosphonic Acid Hydrobromide

Database IDs

• PubChem SID: 162254297
• PubChem CID: 71313261

CALCULATED PROPERTIES

• Acid pKa: 1.7897012
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): 0.76330346
• LogD (pH = 7.4): 0.66015303
• Log P: 0.7640849
• Molar Refractivity: 92.2704 cm^3
• Polarizability: 35.580723 Å^3
• Polar Surface Area: 112.65 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A611070

Sphingosine-1-phosphate, analogs and antagonists for use as medicaments for treating and/or preventing cardiovascular conditions in patients with Fabry disease.

REFERENCES

• Dudek, S., et al.: J. Biol. Chem., 279, 24692 (2004)
• Alfonso, C., et al.: Eur. J. Immunol., 36, 149 (2004)
• Balatoni, B., et al.: Brain Res. Bull., 74, 307 (2004)
• Cherezov, V., et al.: Science, 318, 1258 (2004)
• Foss, F., et al.: Bioorg. Med. Chem., 15,