{[(2S,3S,4R)-2-amino-3,4-dihydroxyoctadecyl]oxy}phosphonic acid

• ChemBase ID: 176470
• Molecular Formular: C18H40NO6P
• Molecular Mass: 397.487061
• Monoisotopic Mass: 397.25932464
• SMILES: C(CCCCCCCCCCCC[C@H]([C@H]([C@H](COP(=O)(O)O)N)O)O)C
• Canonical SMILES: CCCCCCCCCCCCCC[C@H]([C@H]([C@H](COP(=O)(O)O)N)O)O
• InChI: InChI=1S/C18H40NO6P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-17(20)18(21)16(19)15-25-26(22,23)24/h16-18,20-21H,2-15,19H2,1H3,(H2,22,23,24)/t16-,17+,18-/m0/s1
• InChIKey: AYGOSKULTISFCW-KSZLIROESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[(2S,3S,4R)-2-amino-3,4-dihydroxyoctadecyl]oxy}phosphonic acid
• IUPAC Traditional name: phytosphingosine 1-phosphate
• Synonyms: (2S,3S,4R)-2-Amino-1,3,4-octadecanetriol 1-(Dihydrogen Phosphate); 4-D-Hydroxysphinganine 1-Phosphate; Methanol; D-ribo Phytosphingosine 1-Phosphate

Database IDs

• CAS Number: 38597-28-3
• PubChem SID: 164232380
• PubChem CID: 10883829

CALCULATED PROPERTIES

• Acid pKa: 1.5142212
• H Acceptors: 6
• H Donor: 5
• LogD (pH = 5.5): 2.5268817
• LogD (pH = 7.4): 1.6581664
• Log P: 2.561966
• Molar Refractivity: 103.1638 cm^3
• Polarizability: 41.56135 Å^3
• Polar Surface Area: 133.24 Å^2
• Rotatable Bonds: 18
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO (Sparingly); Methanol/Acetic acid; Methanol/HCl
• Apperance: White to Off-White Solid
• Melting Point: 135-139°C

Safety Information

• Storage Condition: Hygroscopic, Refrigerator, Under Inert Atmosphere
• Storage Warning: Hygroscopic

DETAILS

Toronto Research Chemicals - P399000

A potential modulator of cellular processes. A high affinity ligand for the S1P4/Edg-6 receptor.

REFERENCES

• Pyne, S., et al.: Biochem. J., 349, 385 (2000)
• Brinkmann, V., et al.: J. Biol. Chem., 277, 21453 (2000)
• Mandala, S., et al.: Science, 296, 346 (2000)