{2-amino-2-[2-(4-{[3-(benzyloxy)phenyl]sulfanyl}-2-chlorophenyl)ethyl]-3-hydroxypropoxy}phosphonic acid

• ChemBase ID: 172142
• Molecular Formular: C24H27ClNO6PS
• Molecular Mass: 523.966041
• Monoisotopic Mass: 523.0985229
• SMILES: c1c(c(cc(c1)Sc1cccc(c1)OCc1ccccc1)Cl)CCC(COP(=O)(O)O)(CO)N
• Canonical SMILES: OCC(COP(=O)(O)O)(CCc1ccc(cc1Cl)Sc1cccc(c1)OCc1ccccc1)N
• InChI: InChI=1S/C24H27ClNO6PS/c25-23-14-22(10-9-19(23)11-12-24(26,16-27)17-32-33(28,29)30)34-21-8-4-7-20(13-21)31-15-18-5-2-1-3-6-18/h1-10,13-14,27H,11-12,15-17,26H2,(H2,28,29,30)
• InChIKey: JZHXIFZZZFFZBQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {2-amino-2-[2-(4-{[3-(benzyloxy)phenyl]sulfanyl}-2-chlorophenyl)ethyl]-3-hydroxypropoxy}phosphonic acid
• IUPAC Traditional name: 2-amino-2-[2-(4-{[3-(benzyloxy)phenyl]sulfanyl}-2-chlorophenyl)ethyl]-3-hydroxypropoxyphosphonic acid
• Synonyms: 2-Amino-2-[2-[2-chloro-4-[[3-(phenylmethoxy)phenyl]thio]phenyl]ethyl]-1,3-propanediolMono(Dihydrogen Phosphate) (Ester); KRP-203-P; KRP-203 Monophosphate

Database IDs

• CAS Number: 749262-82-6
• PubChem SID: 164228052
• PubChem CID: 16051482

CALCULATED PROPERTIES

• Acid pKa: 1.6166292
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): 3.6320386
• LogD (pH = 7.4): 2.84462
• Log P: 3.6593368
• Molar Refractivity: 135.4694 cm^3
• Polarizability: 53.10464 Å^3
• Polar Surface Area: 122.24 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - K660305

It is used in the synthesis of sphingosine-1-phosphate receptor agonist KRP-203 (K660300). Immunosuppressant.

REFERENCES

• Yanagawa, Y., et al.: J. Immunol., 160, 5493 (1998)
• Takahashi, M., et al.: Cardiovasc. Res., 52, 438 (1998)
• Liu, G., et al.: J. Med. Chem., 43, 4025 (1998)
• Shimizu, H., et al.: Circulation, 111, 222 (2005)