Apoptolidin

Base Information

• Chemical Name: Apoptolidin
• CAS No.: 194874-06-1
• Molecular Formula: C₅₈H₉₆O₂₁
• Molecular Weight: 1129.39
• UNII: SAO6WVQ23I
• ChEMBL ID: CHEMBL4096158
• Metabolomics Workbench ID: 106117
• Nikkaji Number: J1.230.355F
• Wikidata: Q27289111
• Mol file: 194874-06-1.mol

Synonyms:apoptolidin

Chemical Property of Apoptolidin

Chemical Property:

• Melting Point: 128-130°
• Flash Point: 87℃
• PSA: 289.67000
• LogP: 3.58730
• Storage Temp.: ?20°C
• Solubility.: Soluble in DMSO, DMF, ethanol, or methanol.
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 8
• Hydrogen Bond Acceptor Count: 21
• Rotatable Bond Count: 15
• Exact Mass: 1128.64441007
• Heavy Atom Count: 79
• Complexity: 2080

Purity/Quality:

97% ^*data from raw suppliers

Apoptolidin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C=C(C=C(C=C(C(=O)OC(CC(C(CCC=C(C=CC1OC2C(C(C(C(O2)C)OC)O)O)C)O)OC)C(C3(C(C(C(C(O3)CC(COC)OC4CC(C(C(O4)C)OC5CC(C(C(O5)C)O)OC)(C)O)C)O)C)O)O)C)C)C
• Isomeric SMILES: C[C@@H]1/C=C(/C=C(/C=C(/C(=O)O[C@@H](C[C@@H]([C@H](CC/C=C(/C=C/[C@H]1O[C@H]2[C@H]([C@@H]([C@H]([C@@H](O2)C)OC)O)O)\C)O)OC)[C@H]([C@]3([C@@H]([C@H]([C@H]([C@H](O3)C[C@H](COC)O[C@H]4C[C@]([C@H]([C@@H](O4)C)O[C@H]5C[C@H]([C@@H]([C@H](O5)C)O)OC)(C)O)C)O)C)O)O)\C)\C)\C
• Description: Apoptolidin (194874-06-1) is a powerful inducer of apoptosis in a variety of cancer cell lines.1?Is believed to act via inhibition of F0F1-ATPase2?but correlation studies indicate that a second mechanism may be the actual mode of action3.? Cell permeable.
• Uses: Apoptolidin, originally isolated from a Nocardiopsis sp., induces apoptotic cell death in rat glial cells transformed with the adenovirus E1A oncogene (IC50 = 11 ng/ml). Apoptolidin is among the most selective cytotoxic agents tested by the NCI in human cancer cell lines. Although the apoptotic activity of apoptolidin correlates with F0F1-ATPase inhibition, recent evidence suggests the existence of a secondary biological target or more complex mode of action.

Technology Process of Apoptolidin

There total 3 articles about Apoptolidin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 71.0%

4'''-O-tert-butyldimethylsilyl-21-O-methyl-23O,2'O,3'O,3''O-tetrakis(triethylsilyl)apoptolidin A (795290-14-1) → apoptolidin (194874-06-1) + 27-hydroxy apoptolidin A

Guidance literature:

With fluorosilicic acid; In acetonitrile; at -35 - -5 ℃; for 72h;

DOI:10.1002/chem.200600462

Reference yield:

apoptolidin-C21-methyl ketal (502156-06-1) → apoptolidin (194874-06-1)

Guidance literature:

With toluene-4-sulfonic acid; In tetrahydrofuran; water; at 25 ℃; for 2.5h;

DOI:10.1002/1521-3773(20011015)40:20<3854::AID-ANIE3854>3.0.CO;2-D

Reference yield:

isoapoptolidin A (476647-30-0) → apoptolidin (194874-06-1)

Guidance literature:

In various solvent(s); at 37 ℃; Kinetics;

DOI:10.1021/ol0266222

upstream raw materials:

apoptolidin-C₂₁-methyl ketal

isoapoptolidin A

4'''-O-tert-butyldimethylsilyl-21-O-methyl-23O,2'O,3'O,3''O-tetrakis(triethylsilyl)apoptolidin A

Downstream raw materials:

isoapoptolidin A