N-[(2S,3R,4E)-1-{[(2S,3R,4S,5R,6R)-6-(aminomethyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-3-hydroxyoctadec-4-en-2-yl]octadecanamide

• ChemBase ID: 159984
• Molecular Formular: C42H82N2O7
• Molecular Mass: 727.10968
• Monoisotopic Mass: 726.61220297
• SMILES: O(C[C@@H]([C@@H](/C=C/CCCCCCCCCCCCC)O)NC(=O)CCCCCCCCCCCCCCCCC)[C@@H]1[C@H]([C@H]([C@H]([C@@H](O1)CN)O)O)O
• Canonical SMILES: CCCCCCCCCCCCCCCCCC(=O)N[C@H]([C@@H](/C=C/CCCCCCCCCCCCC)O)CO[C@H]1O[C@@H](CN)[C@@H]([C@@H]([C@@H]1O)O)O
• InChI: InChI=1S/C42H82N2O7/c1-3-5-7-9-11-13-15-17-18-20-22-24-26-28-30-32-38(46)44-35(34-50-42-41(49)40(48)39(47)37(33-43)51-42)36(45)31-29-27-25-23-21-19-16-14-12-10-8-6-4-2/h29,31,35-37,39-42,45,47-49H,3-28,30,32-34,43H2,1-2H3,(H,44,46)/b31-29+/t35-,36+,37+,39-,40-,41+,42-/m0/s1
• InChIKey: DNEDNDNJRARMDD-XNQSXISPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(2S,3R,4E)-1-{[(2S,3R,4S,5R,6R)-6-(aminomethyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-3-hydroxyoctadec-4-en-2-yl]octadecanamide
• IUPAC Traditional name: N-[(2S,3R,4E)-1-{[(2S,3R,4S,5R,6R)-6-(aminomethyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-3-hydroxyoctadec-4-en-2-yl]octadecanamide
• Synonyms: 6-Amino-6-deoxy α-Galactosyl-C18-ceramide

Database IDs

• PubChem SID: 162254119
• PubChem CID: 71313193

CALCULATED PROPERTIES

• Acid pKa: 12.191527
• H Acceptors: 8
• H Donor: 6
• LogD (pH = 5.5): 7.0325055
• LogD (pH = 7.4): 8.473258
• Log P: 9.876775
• Molar Refractivity: 209.0485 cm^3
• Polarizability: 83.7091 Å^3
• Polar Surface Area: 154.5 Å^2
• Rotatable Bonds: 35
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - A603900

α-Galactosyl-C18-ceramide derivative. A potent stimulator of human T cells.