(2-{[(4E)-3-hydroxy-2-octadecanamidooctadec-4-en-1-yl phosphonato]oxy}ethyl)trimethylazanium

• ChemBase ID: 131466
• Molecular Formular: C41H83N2O6P
• Molecular Mass: 731.081281
• Monoisotopic Mass: 730.59887502
• SMILES: CCCCCCCCCCCCCCCCCC(=O)NC(COP(=O)([O-])OCC[N+](C)(C)C)C(/C=C/CCCCCCCCCCCCC)O
• Canonical SMILES: CCCCCCCCCCCCCCCCCC(=O)NC(C(/C=C/CCCCCCCCCCCCC)O)COP(=O)(OCC[N+](C)(C)C)[O-]
• InChI: InChI=1S/C41H83N2O6P/c1-6-8-10-12-14-16-18-20-21-23-25-27-29-31-33-35-41(45)42-39(38-49-50(46,47)48-37-36-43(3,4)5)40(44)34-32-30-28-26-24-22-19-17-15-13-11-9-7-2/h32,34,39-40,44H,6-31,33,35-38H2,1-5H3,(H-,42,45,46,47)/b34-32+
• InChIKey: LKQLRGMMMAHREN-NWBJSICCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2-{[(4E)-3-hydroxy-2-octadecanamidooctadec-4-en-1-yl phosphonato]oxy}ethyl)trimethylazanium
• IUPAC Traditional name: (2-{[(4E)-3-hydroxy-2-octadecanamidooctadec-4-en-1-yl phosphonato]oxy}ethyl)trimethylazanium
• Synonyms: N-Octadecanoyl-D-sphingosine-1-phosphocholine; N-Stearoyl-D-sphingomyelin semisynthetic

Database IDs

• CAS Number: 58909-84-5
• MDL Number: MFCD00058390
• PubChem SID: 162225744
• PubChem CID: 5353953

CALCULATED PROPERTIES

• Acid pKa: 1.870915
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 9.888695
• LogD (pH = 7.4): 9.888795
• Log P: 8.954539
• Molar Refractivity: 223.1439 cm^3
• Polarizability: 84.2798 Å^3
• Polar Surface Area: 107.92 Å^2
• Rotatable Bonds: 38
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• German water hazard class: 3
• Storage Temperature: -20°C

DETAILS

Sigma Aldrich - S1388

Biochem/physiol Actions
Molecular species of sphingomyelin; blocks PLCδ1
Quality
A mixture of threo and erythro isomers.