(2S,3R,4E)-2-amino-1-({bis[1-(2-nitrophenyl)ethoxy]phosphoryl}oxy)octadec-4-en-3-ol

• ChemBase ID: 163536
• Molecular Formular: C34H52N3O9P
• Molecular Mass: 677.765141
• Monoisotopic Mass: 677.34411689
• SMILES: C([C@@H]([C@@H](/C=C/CCCCCCCCCCCCC)O)N)OP(=O)(OC(c1c(cccc1)[N+](=O)[O-])C)OC(c1c(cccc1)[N+](=O)[O-])C
• Canonical SMILES: CCCCCCCCCCCCC/C=C/[C@H]([C@H](COP(=O)(OC(c1ccccc1[N+](=O)[O-])C)OC(c1ccccc1[N+](=O)[O-])C)N)O
• InChI: InChI=1S/C34H52N3O9P/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-25-34(38)31(35)26-44-47(43,45-27(2)29-21-17-19-23-32(29)36(39)40)46-28(3)30-22-18-20-24-33(30)37(41)42/h16-25,27-28,31,34,38H,4-15,26,35H2,1-3H3/b25-16+/t27?,28?,31-,34+,47?/m0/s1
• InChIKey: RMOWUMVOVFOKDL-CORYLZCXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3R,4E)-2-amino-1-({bis[1-(2-nitrophenyl)ethoxy]phosphoryl}oxy)octadec-4-en-3-ol
• IUPAC Traditional name: (2S,3R,4E)-2-amino-1-({bis[1-(2-nitrophenyl)ethoxy]phosphoryl}oxy)octadec-4-en-3-ol
• Synonyms: (2S,3R,4E)-2-Amino-3-hydroxy-4-octadecenyl Phosphoric Acid Bis[1-(2-nitrophenyl)ethyl]ester; Caged SPN-1-P; Caged D-erythro-Sphingosine-1-phosphate

Database IDs

• CAS Number: 207516-11-8
• PubChem SID: 162257671
• PubChem CID: 45038535

CALCULATED PROPERTIES

• Acid pKa: 14.170336
• H Acceptors: 7
• H Donor: 2
• LogD (pH = 5.5): 6.36021
• LogD (pH = 7.4): 7.179382
• Log P: 9.361
• Molar Refractivity: 184.4417 cm^3
• Polarizability: 71.445045 Å^3
• Polar Surface Area: 182.65 Å^2
• Rotatable Bonds: 25
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: Brown Thick Oil

Safety Information

• Storage Condition: Hygroscopic, Store under Inert atmosphere -20°C Freezer

DETAILS

Toronto Research Chemicals - C085000

A photolyzable sphingosine 1-phosphate derivative. Caged SPP provides a method to elevate intracellular level of SPP upon ultraviolet irradiation and thus can be utilized as a new tool in studies of SPP-mediated intracellular events. Wavelength 254nm.

REFERENCES

• Mattie, M., et al.: J. Biol .Chem., 269, 3181 (1994)
• Cuvillier, O., et al.: Nature, 381, 800 (1994)
• Hannun, Y., et al.: Science, 274, 1855 (1994)
• Qiao, L., et al.: Bioorg. Med. Chem. Lett., 8, 711 (1994)