CAS 17754-44-8

Atractyloside

Description:

Atractyloside is a naturally occurring glycoside derived from the plant Atractylis gummifera, which is part of the Asteraceae family. It is known for its potent biological activity, particularly as an inhibitor of the adenine nucleotide translocator in mitochondria, which disrupts ATP transport and can lead to cellular energy depletion. This compound is characterized by its ability to induce apoptosis in certain cell types and has been studied for its potential therapeutic applications, as well as its toxic effects. Atractyloside is typically encountered as a white to off-white crystalline powder and is soluble in polar solvents. Its chemical structure features a sugar moiety linked to an aglycone, contributing to its biological activity. Due to its toxicity, it is important to handle atractyloside with care in laboratory settings, and its use is often restricted to research purposes. Overall, atractyloside serves as a significant compound in pharmacological studies, particularly in the context of mitochondrial function and cellular metabolism.

Formula: C₃₀H₄₆O₁₆S₂·2K

InChI: InChI=1S/C30H46O16S2.2K/c1-14(2)9-22(32)44-25-24(46-48(39,40)41)23(45-47(36,37)38)20(13-31)43-28(25)42-17-10-18(27(34)35)19-7-8-30-11-16(15(3)26(30)33)5-6-21(30)29(19,4)12-17;;/h14,16-21,23-26,28,31,33H,3,5-13H2,1-2,4H3,(H,34,35)(H,36,37,38)(H,39,40,41);;/t16-,17-,18-,19-,20-,21+,23-,24+,25-,26+,28-,29-,30-;;/m1../s1

InChI key: InChIKey=NGDIKNWBAWZRRJ-FNAJZLPOSA-N

SMILES: O[C@@H]1[C@]23[C@]([C@@]4(C)[C@](CC2)([C@H](C(O)=O)C[C@@H](O[C@H]5[C@H](OC(CC(C)C)=O)[C@@H](OS(=O)(=O)O)[C@H](OS(=O)(=O)O)[C@@H](CO)O5)C4)[H])(CC[C@](C3)(C1=C)[H])[H].[K]

Synonyms:

• (2b,4a,15a)-15-Hydroxy-2-[[2-O-(3-methyl-1-oxobutyl)-3,4-di-O-sulfo-b-D-glucopyranosyl]oxy]-19-norkaur-16-en-18-oic Acid Dipotassium Salt
• Atractyloside
• Atractylin (C30 glucoside)
• 1H-2,10a-Ethanophenanthrene, 19-norkaur-16-en-18-oic acid deriv.
• 17754-44-8
• Potassium atractylate
• 19-Norkaur-16-en-18-oic acid, 15-hydroxy-2-[[2-O-(3-methyl-1-oxobutyl)-3,4-di-O-sulfo-β-D-glucopyranosyl]oxy]-, potassium salt (1:2), (2β,4α,15α)-
• 19-Norkaur-16-en-18-oic acid, 15-hydroxy-2-[[2-O-(3-methyl-1-oxobutyl)-3,4-di-O-sulfo-β-D-glucopyranosyl]oxy]-, dipotassium salt, (2β,4α,15α)-

Atractyloside

CAS: 17754-44-8

Natural glycoside

Formula: C₃₀H₄₄O₁₆S₂K₂

Purity: ≥ 90.0 % (HPLC)

Color and Shape: Powder

Molecular weight: 802.99

Ref: 5G-84195

Atractyloside

CAS: 17754-44-8

Atractyloside is a diterpene glycoside, which is a naturally occurring compound primarily extracted from the plant Atractylis gummifera. This compound acts as a potent inhibitor of the adenine nucleotide translocase (ANT) located in the mitochondrial inner membrane. Its mode of action involves binding to the ANT, thereby obstructing the exchange of ADP and ATP across the mitochondrial membrane, a crucial process in cellular energy metabolism.

Formula: C₃₀H₄₄K₂O₁₆S₂

Purity: Min. 95%

Molecular weight: 803 g/mol

Ref: 3D-SAA75444