[(2-hexadecanamido-3-hydroxyoctadec-4-en-1-yl)oxy][2-(trimethylamino)ethoxy]phosphinic acid

• ChemBase ID: 155343
• Molecular Formular: C39H80N2O6P
• Molecular Mass: 704.036061
• Monoisotopic Mass: 703.57539992
• SMILES: CCCCCCCCCCCCCCCC(=O)NC(COP(=O)(O)OCC[N](C)(C)C)C(/C=C/CCCCCCCCCCCCC)O
• Canonical SMILES: CCCCCCCCCCCCCCCC(=O)NC(C(/C=C/CCCCCCCCCCCCC)O)COP(=O)(OCC[N](C)(C)C)O
• InChI: InChI=1S/C39H80N2O6P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-38(42)37(36-47-48(44,45)46-35-34-41(3,4)5)40-39(43)33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h30,32,37-38,42H,6-29,31,33-36H2,1-5H3,(H,40,43)(H,44,45)
• InChIKey: MZIMPDIVZFCRCW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2-hexadecanamido-3-hydroxyoctadec-4-en-1-yl)oxy][2-(trimethylamino)ethoxy]phosphinic acid
• IUPAC Traditional name: (2-hexadecanamido-3-hydroxyoctadec-4-en-1-yl)oxy(2-(trimethylamino)ethoxy)phosphinic acid
• Synonyms: N-Hexadecanoyl-D-sphingosine-1-phosphocholine; N-Palmitoyl-D-sphingomyelin semisynthetic from bovine brain sphingomyelin

Database IDs

• CAS Number: 6254-89-3
• MDL Number: MFCD00063521
• PubChem SID: 24898797; 162249481
• PubChem CID: 6033706

CALCULATED PROPERTIES

• Acid pKa: 1.9061377
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 3.6480815
• LogD (pH = 7.4): 3.6288505
• Log P: 5.798094
• Molar Refractivity: 215.0636 cm^3
• Polarizability: 80.7058 Å^3
• Polar Surface Area: 105.09 Å^2
• Rotatable Bonds: 36
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• 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: ~97%
• Empirical Formula (Hill Notation): C39H79N2O6P

DETAILS

Sigma Aldrich - P6778

Biochem/physiol Actions
Molecular species of sphingomyelin; blocks PLC delta 1; converted to ceramide via phospholipase C.
Other Notes
Mixture of erythro- and threo- isomers.