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

Item No. 24879

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-[(1S,2R,3E)-1-[[(O-α-D-galactopyranosyl-(1→4)-O-β-D-galactopyranosyl-(1→4)-β-D-glucopyranosyl)oxy]methyl]-2-hydroxy-3-heptadecenbr-1-yl]-tricyclo[3.3.1.13,7]decane-1-acetamide
CAS Number
261155-87-7
Synonyms
  • AdaGb3
  • Adamantyl Gb3
  • C2 Adamantanyl Ceramide Trihexoside (d18:1/2:0)
Molecular Formula
C48H83NO18
Formula Weight
962.2
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Chloroform:Methanol (2:1): solubleDMF: solubleMethanol: soluble
SMILES
O[C@H]1[C@H](O[C@]2([H])O[C@H](CO)[C@H](O[C@]3([H])[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O3)[C@H](O)[C@H]2O)[C@@H](CO)O[C@@H](OC[C@H](NC(CC45C[C@H](C[C@H](C5)C6)C[C@H]6C4)=O)[C@H](O)/C=C/CCCCCCCCCCCCC)[C@@H]1O
InChi Code
InChI=1S/C48H83NO18/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-31(53)30(49-35(54)22-48-19-27-16-28(20-48)18-29(17-27)21-48)26-62-45-41(60)38(57)43(33(24-51)64-45)67-47-42(61)39(58)44(34(25-52)65-47)66-46-40(59)37(56)36(55)32(23-50)63-46/h14-15,27-34,36-47,50-53,55-61H,2-13,16-26H2,1H3,(H,49,54)/b15-14+/t27-,28+,29-,30-,31+,32+,33+,34+,36-,37-,38+,39+,40+,41+,42+,43+,44-,45+,46+,47-,48?/m0/s1
InChi Key
ATWPTPSAHLZMMT-HJSAUABASA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $468

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    Product Description

    C2 Adamantanyl globotriaosylceramide (AdaGb3) is a bioactive sphingolipid and water-soluble form of globotriaosylceramide (Item Nos. 24870 | 24871 | 24872) that contains an adamantanyl group in place of the fatty acyl chain.1 It inhibits Vero toxin binding to globotriaosylceramide in an ELISA assay when used at a concentration of 10 μM. AdaGb3 decreases cell surface expression of P-glycoprotein (P-gp) and reduces efflux of rhodamine 123 (Item No. 16672) in MDCK cells.2 It also increases apical-to-basal transport of vinblastine (Item No. 11762) in human intestinal C2BBe1 cells. [Matreya, LLC. Catalog No. 1947]

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Mylvaganam, M., Hansen, H.C., Binnington, B., et al. Interaction of the verotoxin 1B subunit with soluble aminodeoxy analogues of globotriaosyl ceramides. Biochem J. 368(Pt 3), 769-776 (2002).

    2. De Rosa, M.F., Ackerley, C., Wang, B., et al. Inhibition of multidrug resistance by adamantylGb3, a globotriaosylceramide analog. The Journal of Biological Chemisty 283(8), 4501-4511 (2008).