C2 Adamantanyl Globotriaosylceramide (d18:1/2:0)

C2 Adamantanyl globotriaosylceramide (AdaGb3) is a bioactive sphingolipid and water-soluble form of globotriaosylceramide (Cay-24870, Cay-24871, Cay-24872) that contains an adamantanyl group in place of the fatty acyl chain. 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 (Cay-16672) in MDCK cells. It also increases apical-to-basal transport of vinblastine (Cay-11762) in human intestinal C2BBe1 cells. [Matreya, LLC. Catalog No. 1947]Formal Name: N-[(1S,2R,3E)-1-[[(O-alpha-D-galactopyranosyl-(1->4)-O-beta-D-galactopyranosyl-(1->4)-beta-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: A solid. 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.