A bioactive sphingolipid
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C2 Adamantanyl Glucosylceramide (d18:1/2:0)

Item No. 24623

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-((3S,5S,7S)-adamantan-1-yl)-N-((2S,3R,4E,8E)-3-hydroxy-1-(((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)octadeca-4,8-dien-2-yl)acetamide
Synonyms
  • N-(1-Adamantaneacetyl) Glucosylceramide
  • Adamantanyl GluCer(d18:1/2:0)
  • Adamantanyl Glucosylceramide (d18:1/2:0)
  • AdaGluCer(d18:1/2:0)
Molecular Formula
C36H61NO8
Formula Weight
635.9
Purity
≥98%
Formulation (Request formulation change)
A solid
SMILES
O[C@H]1[C@H](O)[C@@H](CO)O[C@@H](OC[C@H](NC(CC23C[C@H](C[C@H](C3)C4)C[C@H]4C2)=O)[C@H](O)/C=C/CC/C=C/CCCCCCCCC)[C@@H]1O
InChi Code
InChI=1S/C36H61NO8/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-29(39)28(24-44-35-34(43)33(42)32(41)30(23-38)45-35)37-31(40)22-36-19-25-16-26(20-36)18-27(17-25)21-36/h10-11,14-15,25-30,32-35,38-39,41-43H,2-9,12-13,16-24H2,1H3,(H,37,40)/b11-10+,15-14+/t25-,26+,27-,28-,29+,30+,32+,33-,34+,35+,36?/m0/s1
InChi Key
IZNODOFHHDPHST-MBCMVAOSSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $255

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    Product Description

    C2 Adamantanyl glucosylceramide (AdaGluCer) is a bioactive sphingolipid.1 It increases levels of glycosphingolipids in Vero cells at low concentrations (≤20 μM) but decreases them at high concentrations (≥40 μM). Pretreatment of microsomes with AdaGluCer increases production of adamantanyl lactosylceramide (AdaLacCer) and reduces synthesis of LacCer from exogenous GlcCer. AdaGluCer inhibits glucocerebrosidase activity in vitro in a pH-dependent manner. [Matreya, LLC. Catalog No. 1945]

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Kamani, M., Mylvaganam, M., Tian, R., et al. Adamantyl glycosphingolipids provide a new approach to the selective regulation of cellular glycosphingolipid metabolism. The Journal of Biological Chemisty 286(24), 21413-21426 (2011).