(2S,3R)-2-(octylamino)octadec-4-ene-1,3-diol

• ChemBase ID: 155617
• Molecular Formular: C26H53NO2
• Molecular Mass: 411.70452
• Monoisotopic Mass: 411.40762994
• SMILES: CCCCCCCCCCCCC/C=C/[C@H]([C@H](CO)NCCCCCCCC)O
• Canonical SMILES: CCCCCCCCCCCCC/C=C/[C@H]([C@@H](NCCCCCCCC)CO)O
• InChI: InChI=1S/C26H53NO2/c1-3-5-7-9-11-12-13-14-15-16-17-18-20-22-26(29)25(24-28)27-23-21-19-10-8-6-4-2/h20,22,25-29H,3-19,21,23-24H2,1-2H3/t25-,26+/m0/s1
• InChIKey: CSRGRGSMEUKQSD-IZZNHLLZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3R)-2-(octylamino)octadec-4-ene-1,3-diol
• IUPAC Traditional name: (2S,3R)-2-(octylamino)octadec-4-ene-1,3-diol
• Synonyms: N-Octyl-D-sphingosine; D-erythro-Ceramine C8

Database IDs

• MDL Number: MFCD01632747
• PubChem SID: 162249755
• PubChem CID: 16759361

CALCULATED PROPERTIES

• Acid pKa: 14.108702
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): 4.917669
• LogD (pH = 7.4): 5.950991
• Log P: 8.101335
• Molar Refractivity: 128.9442 cm^3
• Polarizability: 51.190536 Å^3
• Polar Surface Area: 52.49 Å^2
• Rotatable Bonds: 23
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: soluble25 mg/mL; ethanol: soluble25 mg/mL
• Apperance: white solid

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: 98% (TLC)
• Empirical Formula (Hill Notation): C26H53NO2

DETAILS

Sigma Aldrich - C8480

Biochem/physiol Actions
Inert to ceramidases; induces peak DNA fragmentation in 6 hrs; induces apoptosis in U937 cells.