tert-butyl N-[(2R,3R,4E)-1-{[bis(2-cyanoethoxy)phosphoryl]oxy}-3-hydroxy(1,2-13C2,1,1-2H2)octadec-4-en-2-yl]carbamate

• ChemBase ID: 162252
• Molecular Formular: C29H52N3O7P
• Molecular Mass: 587.69815068
• Monoisotopic Mass: 587.36099733
• SMILES: [C@H](/C=C/CCCCCCCCCCCCC)(O)[13C@H]([13CH2]OP(=O)(OCCC#N)OCCC#N)NC(=O)OC(C)(C)C
• Canonical SMILES: CCCCCCCCCCCCC/C=C/[C@H]([13C@@H](NC(=O)OC(C)(C)C)[13CH2]OP(=O)(OCCC#N)OCCC#N)O
• InChI: InChI=1S/C29H52N3O7P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-20-27(33)26(32-28(34)39-29(2,3)4)25-38-40(35,36-23-18-21-30)37-24-19-22-31/h17,20,26-27,33H,5-16,18-19,23-25H2,1-4H3,(H,32,34)/b20-17+/t26-,27+/m0/s1/i25+1,26+1
• InChIKey: IOLHEZANZMTGKL-WEHPCQFSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: tert-butyl N-[(2R,3R,4E)-1-{[bis(2-cyanoethoxy)phosphoryl]oxy}-3-hydroxy(1,2-^1^3C₂,1,1-^2H₂)octadec-4-en-2-yl]carbamate
• IUPAC Traditional name: tert-butyl N-[(2R,3R,4E)-1-{[bis(2-cyanoethoxy)phosphoryl]oxy}-3-hydroxy(1,2-^1^3C₂,1,1-^2H₂)octadec-4-en-2-yl]carbamate
• Synonyms: Bis(2-cyanoethoxy)-1-(N-t-boc-sphingosine-1-phosphate-13C2, D2

Database IDs

• PubChem SID: 162256387
• PubChem CID: 45038367

CALCULATED PROPERTIES

• Acid pKa: 12.292418
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 6.2369227
• LogD (pH = 7.4): 6.2369175
• Log P: 6.2369227
• Molar Refractivity: 156.1291 cm^3
• Polarizability: 61.526085 Å^3
• Polar Surface Area: 150.9 Å^2
• Rotatable Bonds: 26
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: Off-White Solid With a Yellow Tinge

DETAILS

Toronto Research Chemicals - B419852

Intermediate for a labelled putative lipid second messenger; found to inhibit cellular mobility of melanoma cells at very low concentrations with no toxic effects thereby making it a possible agent for prevention of tumor cell metastasis and inflammator

REFERENCES

• Zhang, H., et al.: J. Cell Biol., 114, 155 (1991) Sadahira, Y., et al.: Proc. Natl. Acad. Sci. USA (1992)
• Cuvillier, O., et al.: Nature, 381, 800 (1996)