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

• ChemBase ID: 153501
• Molecular Formular: C34H67NO3
• Molecular Mass: 537.90068
• Monoisotopic Mass: 537.51209501
• SMILES: CCCCCCCCCCCCCCCC(=O)N[C@@H](CO)[C@@H](/C=C/CCCCCCCCCCCCC)O
• Canonical SMILES: CCCCCCCCCCCCCCCC(=O)N[C@H]([C@@H](/C=C/CCCCCCCCCCCCC)O)CO
• InChI: InChI=1S/C34H67NO3/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-33(37)32(31-36)35-34(38)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h27,29,32-33,36-37H,3-26,28,30-31H2,1-2H3,(H,35,38)/t32-,33+/m0/s1
• InChIKey: YDNKGFDKKRUKPY-JHOUSYSJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(2S,3R)-1,3-dihydroxyoctadec-4-en-2-yl]hexadecanamide
• IUPAC Traditional name: N-[(2S,3R)-1,3-dihydroxyoctadec-4-en-2-yl]hexadecanamide
• Synonyms: C16 ceramide; N-Hexadecanoyl-D-sphingosine; N-Palmitoyl-D-erythro-sphingosine; Palmitoyl ceramide; N-Palmitoyl-D-sphingosine semisynthetic from bovine brain D-sphingosine

Database IDs

• CAS Number: 24696-26-2
• MDL Number: MFCD00056205
• PubChem SID: 162247640
• PubChem CID: 5283564

CALCULATED PROPERTIES

• Acid pKa: 13.619749
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): 10.865354
• LogD (pH = 7.4): 10.865355
• Log P: 10.8653555
• Molar Refractivity: 165.7757 cm^3
• Polarizability: 65.59229 Å^3
• Polar Surface Area: 69.56 Å^2
• Rotatable Bonds: 30
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: ethanol: soluble (warm)
• Apperance: white powder

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: ≥99% (TLC)
• Empirical Formula (Hill Notation): C34H67NO3

DETAILS

Sigma Aldrich - P9157

Biochem/physiol Actions
Naturally occurring ceramide; induces EGF receptor phosphorylation in A-431 cells; activates phospholipase A2.