CAS 18404-43-8

(3β,5β)-3-[(2,6-Dideoxy-β-D-ribo-hexopyranosyl)oxy]-14-hydroxycard-20(22)-enolide

Description:

The chemical substance known as "(3β,5β)-3-[(2,6-Dideoxy-β-D-ribo-hexopyranosyl)oxy]-14-hydroxycard-20(22)-enolide," with the CAS number 18404-43-8, is a type of cardenolide, which is a class of compounds characterized by a steroid structure with a lactone ring. This particular compound features a hydroxyl group at the 14-position and a glycosidic linkage to a dideoxy sugar, contributing to its solubility and biological activity. Cardenolides are known for their potent effects on the cardiovascular system, often acting as inhibitors of the Na+/K+ ATPase enzyme, which can lead to increased cardiac contractility. The presence of the sugar moiety may enhance its pharmacological properties and bioavailability. Additionally, the specific stereochemistry indicated by the nomenclature suggests a complex three-dimensional arrangement that can influence its interaction with biological targets. Overall, this compound exemplifies the intricate relationship between structure and function in natural products, particularly in the context of medicinal chemistry and pharmacology.

Formula: C₂₉H₄₄O₇

InChI: InChI=1S/C29H44O7/c1-16-26(32)23(30)14-25(35-16)36-19-6-9-27(2)18(13-19)4-5-22-21(27)7-10-28(3)20(8-11-29(22,28)33)17-12-24(31)34-15-17/h12,16,18-23,25-26,30,32-33H,4-11,13-15H2,1-3H3/t16-,18-,19+,20-,21+,22-,23+,25+,26-,27+,28-,29+/m1/s1

InChI key: InChIKey=NQOMDNMTNVQXRR-WQLPVBBFSA-N

SMILES: O[C@@]12[C@@](C)([C@H](CC1)C3=CC(=O)OC3)CC[C@]4([C@]2(CC[C@]5([C@]4(C)CC[C@H](O[C@H]6C[C@H](O)[C@H](O)[C@@H](C)O6)C5)[H])[H])[H]

Synonyms:

• (3alpha,5beta,8xi,9xi)-3-[(2,6-dideoxy-beta-D-glycero-hexopyranosyl)oxy]-14-hydroxycard-20(22)-enolide
• (3beta,5beta)-3-[(2,6-dideoxy-beta-D-ribo-hexopyranosyl)oxy]-14-hydroxycard-20(22)-enolide
• (3β,5β)-3-[(2,6-Dideoxy-β-<span class="text-smallcaps">D</span>-ribo-hexopyranosyl)oxy]-14-hydroxycard-20(22)-enolide
• 5β-Card-20(22)-enolide, 3β-[(2,6-dideoxy-β-<span class="text-smallcaps">D</span>-ribo-hexopyranosyl)oxy]-14-hydroxy-
• <span class="text-smallcaps">D</span>-ribo-Hexopyranoside, digitoxigenin-3 2,6-dideoxy-, β-
• Card-20(22)-enolide, 3-[(2,6-dideoxy-β-<span class="text-smallcaps">D</span>-ribo-hexopyranosyl)oxy]-14-hydroxy-, (3β,5β)-
• Digitoxigenin 2,6-dideoxy-β-<span class="text-smallcaps">D</span>-ribo-hexopyranoside
• Digitoxigenin Monodigitoxoside
• Digitoxigenin digitoxoside
• Digitoxigenin-Monodigitoxosid
• Evatromonoside
• (3β,5β)-3-[(2,6-Dideoxy-β-D-ribo-hexopyranosyl)oxy]-14-hydroxycard-20(22)-enolide
• D-ribo-Hexopyranoside, digitoxigenin-3 2,6-dideoxy-, β-
• 5β-Card-20(22)-enolide, 3β-[(2,6-dideoxy-β-D-ribo-hexopyranosyl)oxy]-14-hydroxy-

Digitoxigenin Mono-β-D-digitoxoside

Controlled Product

CAS: 18404-43-8

Formula: C₂₉H₄₄O₇

Color and Shape: White To Off-White

Molecular weight: 504.66

Ref: TR-D450835

Digitoxigenin mono-β-D-digitoxoside

CAS: 18404-43-8

Digitoxigenin mono-β-D-digitoxoside is a potent inhibitor of tumor growth and cancer cell proliferation. It is an analog of the cardiac glycoside digitoxin, which is known for its anticancer properties. Digitoxigenin mono-β-D-digitoxoside has been shown to induce apoptosis in human cancer cells by inhibiting protein kinases such as AKT and ERK1/2. This drug also has potential therapeutic applications in the treatment of ghrelin-related diseases, as it has been shown to inhibit the activity of ghrelin, a hormone that stimulates appetite and promotes weight gain. Additionally, digitoxigenin mono-β-D-digitoxoside exhibits high water solubility due to its cellulose-based structure, making it ideal for use in urine-based diagnostic tests for cancer detection.

Formula: C₂₉H₄₄O₇

Purity: Min. 95%

Molecular weight: 504.7 g/mol

Ref: 3D-TAA40443