2-[(acetyloxy)methyl]-4-(4-{[3-(benzyloxy)phenyl]sulfanyl}-2-chlorophenyl)-2-acetamidobutyl acetate

• ChemBase ID: 159059
• Molecular Formular: C30H32ClNO6S
• Molecular Mass: 570.09618
• Monoisotopic Mass: 569.16388643
• SMILES: c1c(c(cc(c1)Sc1cccc(c1)OCc1ccccc1)Cl)CCC(COC(=O)C)(COC(=O)C)NC(=O)C
• Canonical SMILES: CC(=O)NC(CCc1ccc(cc1Cl)Sc1cccc(c1)OCc1ccccc1)(COC(=O)C)COC(=O)C
• InChI: InChI=1S/C30H32ClNO6S/c1-21(33)32-30(19-37-22(2)34,20-38-23(3)35)15-14-25-12-13-28(17-29(25)31)39-27-11-7-10-26(16-27)36-18-24-8-5-4-6-9-24/h4-13,16-17H,14-15,18-20H2,1-3H3,(H,32,33)
• InChIKey: MTDPJCGQFNTZEZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(acetyloxy)methyl]-4-(4-{[3-(benzyloxy)phenyl]sulfanyl}-2-chlorophenyl)-2-acetamidobutyl acetate
• IUPAC Traditional name: 2-[(acetyloxy)methyl]-4-(4-{[3-(benzyloxy)phenyl]sulfanyl}-2-chlorophenyl)-2-acetamidobutyl acetate
• Synonyms: N-[1,1-Bis[(acetyloxy)methyl]-3-[2-chloro-4-[[3-(phenylmethoxy)phenyl]thio]phenyl]propyl]-acetamide; N-Acetyl-di-O-acetyl KRP-203

Database IDs

• CAS Number: 951238-25-8
• PubChem SID: 162253194
• PubChem CID: 71312779

CALCULATED PROPERTIES

• Acid pKa: 12.148605
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 5.4962687
• LogD (pH = 7.4): 5.4962626
• Log P: 5.496269
• Molar Refractivity: 152.3433 cm^3
• Polarizability: 59.941673 Å^3
• Polar Surface Area: 90.93 Å^2
• Rotatable Bonds: 15
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Dichloromethane
• Apperance: Colorless Oil

DETAILS

Toronto Research Chemicals - A167970

Protected KRP-203. A sphingosine-1-phosphate receptor agonists in the treatment of autoimmune diseases. 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)