(2S,3R,4E)-2-acetamido-3-hydroxyoctadec-4-en-1-yl benzoate

• ChemBase ID: 161291
• Molecular Formular: C27H43NO4
• Molecular Mass: 445.63462
• Monoisotopic Mass: 445.31920886
• SMILES: C(CCCCCCCCCCC/C=C/[C@H]([C@H](COC(=O)c1ccccc1)NC(=O)C)O)C
• Canonical SMILES: CCCCCCCCCCCCC/C=C/[C@H]([C@@H](NC(=O)C)COC(=O)c1ccccc1)O
• InChI: InChI=1S/C27H43NO4/c1-3-4-5-6-7-8-9-10-11-12-13-14-18-21-26(30)25(28-23(2)29)22-32-27(31)24-19-16-15-17-20-24/h15-21,25-26,30H,3-14,22H2,1-2H3,(H,28,29)/b21-18+/t25-,26+/m0/s1
• InChIKey: VEPYGQXEUMTGOL-UHIBZTAXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3R,4E)-2-acetamido-3-hydroxyoctadec-4-en-1-yl benzoate
• IUPAC Traditional name: (2S,3R,4E)-2-acetamido-3-hydroxyoctadec-4-en-1-yl benzoate
• Synonyms: 1-O-benzoyl-N-[(1S,2R,3E)-2-hydroxy-1-(hydroxymethyl)-3-heptadecen-1-yl]acetamide; 1-O-benzoyl-N-acetyl-D-sphingosine; 1-O-benzoyl Acetyl Ceramide; 1-O-benzoyl N-Acetylsphingosine; 1-O-Benzoyl C2 Ceramide

Database IDs

• PubChem SID: 162255426
• PubChem CID: 71313708

CALCULATED PROPERTIES

• Acid pKa: 13.287695
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 6.8807263
• LogD (pH = 7.4): 6.880726
• Log P: 6.8807263
• Molar Refractivity: 131.1578 cm^3
• Polarizability: 51.327435 Å^3
• Polar Surface Area: 75.63 Å^2
• Rotatable Bonds: 19
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Methanol
• Apperance: Off-white Solid

DETAILS

Toronto Research Chemicals - B208030

C2 Ceramide (C262500) derivative.