82026-06-0

Basic information

• Product Name: 3-ketoaphidicolin
• Synonyms: 3-ketoaphidicolin
• CAS NO: 82026-06-0
• Molecular Formula: C20H32O4
• Molecular Weight: 336.47
• Mol File: 82026-06-0.mol

Chemical Properties

• Boiling Point: 506.9°C at 760 mmHg
• Flash Point: 274.5°C
• Appearance: /
• Density: 1.22g/cm³
• Vapor Pressure: 2.13E-12mmHg at 25°C
• Refractive Index: 1.577
• CAS DataBase Reference: 3-ketoaphidicolin(CAS DataBase Reference)
• NIST Chemistry Reference: 3-ketoaphidicolin(82026-06-0)
• EPA Substance Registry System: 3-ketoaphidicolin(82026-06-0)

Safety Data

• Hazardous Substances Data: 82026-06-0(Hazardous Substances Data)

Usage

Source

Derived from the fungus Phoma sp.

Potential properties

Antitumor and cancer-fighting

Structural similarity

to aphidicolin, a known inhibitor of DNA polymerases

Cytotoxic effects

Exhibits cytotoxic effects against various cancer cell lines

Mechanism of action

Inhibits DNA synthesis and induces cell cycle arrest

Potential use

Promising candidate for the development of new anti-cancer drugs

Future prospects

Further research may lead to the development of novel cancer treatments and therapies

InChI:InChI=1/C20H32O4/c1-17(11-21)15-4-3-13-9-14-10-19(13,7-8-20(14,24)12-22)18(15,2)6-5-16(17)23/h13-15,21-22,24H,3-12H2,1-2H3/t13-,14+,15-,17+,18-,19-,20-/m1/s1

Upstream product

• 38966-21-1 aphidicolin 

Relevant articles and documents

Microbial Transformations of Natural Antitumor Agents. 21. Conversions of Aphidicolin

Microbial transformations have been employed as a means of preparing analogues of the diterpene aphidicolin.Microbial transformation products were initially identified by thin-layer chromatography of fermentation extracts and then were prepared by larger scale incubations.Each microbial metabolite was subjected to structure elucidation employing carbon-13 and proton NMR, high-resolution mass spectrometry, and infrared analysis.Metabolites were identified as 3α-acetoxy-16,17,18-trihydroxyaphidicolane, 18-acetoxy-3α,16,17-trihydroxyaphidicolane,3α,16,17-trihydroxyaphidicolan-18-oate, 16,17,18-trihydroxyaphidicolan-3-one, 3β,16,17,18-tetrahydroxyaphidicolane, and 3α,6β,16,17,18-pentahydroxyaphidicolane.The availability of the microbial metabolites enabled the near complete elucidation of the carbon-13 NMR spectrum of aphidicolin.Biological evaluations of these compounds were made by using in vivo and in vitro techniques.None of the metabolites were active in an in vivo antitumor test system, while all of the compounds inhibited the uptake of the thymidine to P-388 leukemic cells in vitro.