{[(2S,3R,4E)-3-hydroxy-2-octadecanamidooctadec-4-en-1-yl]oxy}phosphonic acid

• ChemBase ID: 132461
• Molecular Formular: C36H72NO6P
• Molecular Mass: 645.933741
• Monoisotopic Mass: 645.50972566
• SMILES: CCCCCCCCCCCCCCCCCC(=O)N[C@@H](COP(=O)(O)O)[C@@H](/C=C/CCCCCCCCCCCCC)O
• Canonical SMILES: CCCCCCCCCCCCCCCCCC(=O)N[C@H]([C@@H](/C=C/CCCCCCCCCCCCC)O)COP(=O)(O)O
• InChI: InChI=1S/C36H72NO6P/c1-3-5-7-9-11-13-15-17-18-20-22-24-26-28-30-32-36(39)37-34(33-43-44(40,41)42)35(38)31-29-27-25-23-21-19-16-14-12-10-8-6-4-2/h29,31,34-35,38H,3-28,30,32-33H2,1-2H3,(H,37,39)(H2,40,41,42)/b31-29+/t34-,35+/m0/s1
• InChIKey: ZQQLMECVOXKFJK-NXCSZAMKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[(2S,3R,4E)-3-hydroxy-2-octadecanamidooctadec-4-en-1-yl]oxy}phosphonic acid
• IUPAC Traditional name: C18 CerP
• Synonyms: Ceramide 1-phosphate from bovine brain

Database IDs

• CAS Number: 128543-23-7
• MDL Number: MFCD00678983
• PubChem SID: 162226738; 24892731
• PubChem CID: 5283583

CALCULATED PROPERTIES

• Acid pKa: 1.528374
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): 9.226857
• LogD (pH = 7.4): 8.347929
• Log P: 11.469102
• Molar Refractivity: 185.8506 cm^3
• Polarizability: 73.46301 Å^3
• Polar Surface Area: 116.09 Å^2
• Rotatable Bonds: 34
• 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: ~95%

DETAILS

Sigma Aldrich - C4832

Biochem/physiol Actions
Putative second messenger of agonist-stimulated sphingomyelin metabolism; may participate in cell regulation and transmembrane signaling.
Other Notes
Contains primarily stearic and nervonic acids.