alpha-Galactosylceramide, NKT cell stimulator

Key facts

CAS number

158021-47-7

Purity

>96%

Form

Solid

form

Molecular weight

858.3 Da

Molecular formula

C₅₀H₉₉NO₉

PubChem

2826713

Nature

Synthetic

Biochemical name

alpha-GalCer

Biological description

Potent NKT cell stimulator. Selective CD1d ligand. Stimulates lymphocyte proliferation and enhances antibody production. Shows antiangiogenic, antitumor and potent immunoregulatory effects in vivo.

Canonical smiles

CCCCCCCCCCCCCCCCCCCCCCCCCC(=O)NC(COC1C(C(C(C(O1)CO)O)O)O)C(C(CCCCCCCCCCCCCC)O)O

Isomeric smiles

CCCCCCCCCCCCCCCCCCCCCCCCCC(=O)N[C@@H](CO[C@@H]1[C@@H]([C@H]([C@H]([C@H](O1)CO)O)O)O)[C@@H]([C@@H](CCCCCCCCCCCCCC)O)O

InChi

InChI=1S/C50H99NO9/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-23-24-25-26-27-29-31-33-35-37-39-45(54)51-42(41-59-50-49(58)48(57)47(56)44(40-52)60-50)46(55)43(53)38-36-34-32-30-28-16-14-12-10-8-6-4-2/h42-44,46-50,52-53,55-58H,3-41H2,1-2H3,(H,51,54)/t42-,43+,44+,46-,47-,48-,49+,50-/m0/s1

InChiKey

VQFKFAKEUMHBLV-BYSUZVQFSA-N

IUPAC Name

N-[(2S,3S,4R)-3,4-dihydroxy-1-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoctadecan-2-yl]hexacosanamide