N-[(2S,3R,4E)-1,3-dihydroxyoctadec-4-en-2-yl]icosanamide

• ChemBase ID: 164000
• Molecular Formular: C38H75NO3
• Molecular Mass: 594.007
• Monoisotopic Mass: 593.57469527
• SMILES: C(C/C=C/[C@H]([C@H](CO)NC(=O)CCCCCCCCCCCCCCCCCCC)O)CCCCCCCCCCC
• Canonical SMILES: CCCCCCCCCCCCCCCCCCCC(=O)N[C@H]([C@@H](/C=C/CCCCCCCCCCCCC)O)CO
• InChI: InChI=1S/C38H75NO3/c1-3-5-7-9-11-13-15-17-18-19-20-22-24-26-28-30-32-34-38(42)39-36(35-40)37(41)33-31-29-27-25-23-21-16-14-12-10-8-6-4-2/h31,33,36-37,40-41H,3-30,32,34-35H2,1-2H3,(H,39,42)/b33-31+/t36-,37+/m0/s1
• InChIKey: XWBWIAOWSABHFI-NUKVNZTCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(2S,3R,4E)-1,3-dihydroxyoctadec-4-en-2-yl]icosanamide
• IUPAC Traditional name: C20 cer
• Synonyms: N-Eicosanoylsphingosine; N-[(1S,2R,3E)-2-Hydroxy-1-(hydroxymethyl)-3-heptadecenyl]Eicosanamide; (E)-D-erythro- N-[2-Hydroxy-1-(hydroxymethyl)-3-heptadecenyl]Eicosanamide; [R-[R*,S*-(E)]]-N-[2-Hydroxy-1-(hydroxymethyl)-3-heptadecenyl]Eicosanamide; N-(Eicosanoyl)-D-erythro-1,3-dihydroxy-2-amino-4-trans-octadecene; N-(Eicosanoyl)sphingosine; N-Eicosanoyl-C18-sphingosine; C20 Ceramide

Database IDs

• CAS Number: 7344-02-7
• PubChem SID: 162258135
• PubChem CID: 5283566

CALCULATED PROPERTIES

• Acid pKa: 13.619749
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): 12.643628
• LogD (pH = 7.4): 12.643629
• Log P: 12.64363
• Molar Refractivity: 184.1797 cm^3
• Polarizability: 72.97441 Å^3
• Polar Surface Area: 69.56 Å^2
• Rotatable Bonds: 34
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: White Solid
• Melting Point: 89-90°C

Safety Information

• Storage Condition: -20°C Freezer