(2R,3R,4S,5S,6R)-2-{[(2S,3R,4E)-2-amino-3-hydroxyoctadec-4-en-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

• ChemBase ID: 169680
• Molecular Formular: C24H47NO7
• Molecular Mass: 461.63248
• Monoisotopic Mass: 461.33525285
• SMILES: O(C[C@@H]([C@@H](/C=C/CCCCCCCCCCCCC)O)N)[C@H]1[C@H]([C@H]([C@@H]([C@@H](O1)CO)O)O)O
• Canonical SMILES: CCCCCCCCCCCCC/C=C/[C@H]([C@H](CO[C@@H]1O[C@@H](CO)[C@H]([C@@H]([C@@H]1O)O)O)N)O
• InChI: InChI=1S/C24H47NO7/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19(27)18(25)17-31-24-23(30)22(29)21(28)20(16-26)32-24/h14-15,18-24,26-30H,2-13,16-17,25H2,1H3/b15-14+/t18-,19+,20+,21+,22-,23+,24+/m0/s1
• InChIKey: HHJTWTPUPVQKNA-JIAPQYILSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4S,5S,6R)-2-{[(2S,3R,4E)-2-amino-3-hydroxyoctadec-4-en-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol
• IUPAC Traditional name: D-glucosylsphingosine
• Synonyms: Glucosylsphingosine; 2-Amino-3-hydroxy-4-octadecenyl β-D-Glucopyranoside; (2S,3R,4E)-2-Amino-3-hydroxy-4-octadecenyl β-D-Glucopyranoside; Glucosyl-C18-sphingosine

Database IDs

• CAS Number: 52050-17-6
• PubChem SID: 162263812
• PubChem CID: 5280570

CALCULATED PROPERTIES

• Acid pKa: 12.206499
• H Acceptors: 8
• H Donor: 6
• LogD (pH = 5.5): -0.13794628
• LogD (pH = 7.4): 1.0860742
• Log P: 2.7957444
• Molar Refractivity: 124.3053 cm^3
• Polarizability: 49.999756 Å^3
• Polar Surface Area: 145.63 Å^2
• Rotatable Bonds: 18
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Light Brown Residue

DETAILS

Toronto Research Chemicals - G596840

A sphingosine derivative. A sphingolipid compound found in the the umbilical cord artery of women with preeclampsia.

REFERENCES

• Romanowicz, L. et al.: Mol. Cell. Biochem. 340, 81 (2010)