(2-{[(2S,3R,4E)-2-amino-3-hydroxyoctadec-4-en-1-yl phosphonato]oxy}ethyl)trimethylazanium

• ChemBase ID: 134173
• Molecular Formular: C23H49N2O5P
• Molecular Mass: 464.619321
• Monoisotopic Mass: 464.33790931
• SMILES: CCCCCCCCCCCCC/C=C/[C@H]([C@H](COP(=O)([O-])OCC[N+](C)(C)C)N)O
• Canonical SMILES: CCCCCCCCCCCCC/C=C/[C@H]([C@H](COP(=O)(OCC[N+](C)(C)C)[O-])N)O
• InChI: InChI=1S/C23H49N2O5P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-23(26)22(24)21-30-31(27,28)29-20-19-25(2,3)4/h17-18,22-23,26H,5-16,19-21,24H2,1-4H3/b18-17+/t22-,23+/m0/s1
• InChIKey: JLVSPVFPBBFMBE-HXSWCURESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2-{[(2S,3R,4E)-2-amino-3-hydroxyoctadec-4-en-1-yl phosphonato]oxy}ethyl)trimethylazanium; (2-{[(2S,3R)-2-amino-3-hydroxyoctadec-4-en-1-yl phosphonato]oxy}ethyl)trimethylazanium
• IUPAC Traditional name: sphingosylphosphorylcholine; (2-{[(2S,3R)-2-amino-3-hydroxyoctadec-4-en-1-yl phosphonato]oxy}ethyl)trimethylazanium
• Synonyms: (2S,3R,4E)-2-Amino-4-octadecene-3-hydroxy-1-phosphocholine; 2-[[[(2-Amino-3-hydroxy-4-octadecenyl)oxy]hydroxy-phosphinyl]oxy]-N,N,N-trimethylethanaminium inner salt; D-erythro-Sphingosine phosphocholine; Lyso SM (d18:1); Lysosphingomyelin; Sphingosylphosphorylcholine; 2-[[[[(2S,3R,4E)-2-Amino-3-hydroxy-4-octadecen-1-yl]oxy]hydroxyphosphinyl]oxy]-N,N,N-trimethyl-ethanaminium; Sphingenyl-1-phosphorylcholine; D-erythro-Sphingosylphosphorylcholine (Synthetic)

Database IDs

• CAS Number: 1670-26-4
• MDL Number: MFCD02259287
• Beilstein Number: 7342520
• PubChem SID: 162228450; 24899596
• PubChem CID: 9847290

CALCULATED PROPERTIES

• Acid pKa: 1.8297435
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -0.30242163
• LogD (pH = 7.4): 0.48946673
• Log P: -0.2439917
• Molar Refractivity: 140.0582 cm^3
• Polarizability: 51.45731 Å^3
• Polar Surface Area: 104.84 Å^2
• Rotatable Bonds: 21
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: light yellow powder; Yellowish Waxy Solid
• Melting Point: 90-102°C

Safety Information

• Storage Condition: -20°C Freezer
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥96% (TLC); ≥98%
• Impurities: ≤6% water
• Empirical Formula (Hill Notation): C23H49N2O5P

DETAILS

Sigma Aldrich - S4257

Biochem/physiol Actions
Mobilizes Ca2+ from intracellular stores via an IP3-independent pathway.

Sigma Aldrich - 85624

Other Notes
Preparation of D-erythro sphingomyelins1

Toronto Research Chemicals - S681700

Involved in cell regulation, and transmembrane signaling. A putative lipid second messenger, connected via Protein Kinase C to the phosphatidylinositol-derived second messengers for signal transduction.

REFERENCES

• Kratzer, B. and Schmidt, R.R.: Liebigs Ann., 955-963 (1995)