viridicatumtoxin

Base Information

• Chemical Name: viridicatumtoxin
• CAS No.: 39277-41-3
• Molecular Formula: C₃₀H₃₁NO₁₀
• Molecular Weight: 565.577
• Mol file: 39277-41-3.mol

Synonyms:Spiro[2-cyclohexene-1,2'(1'H)-cyclopenta[de]naphthacene]-9'-carboxamide,7',7'a,8',11',11'a,12'-hexahydro-5',6',7'a,10',11'a,12'-hexahydroxy-3'-methoxy-2,6,6-trimethyl-7',8'-dioxo-,(2'a,7'ab,11'ab,12'b)-(-)-; NSC 159628;Viridicatumtoxin

Chemical Property of viridicatumtoxin

Chemical Property:

• Melting Point: 235°C (rough estimate)
• Refractive Index: 1.6310 (estimate)
• Boiling Point: 711.8°Cat760mmHg
• Flash Point: 384.3°C
• PSA: 207.84000
• Density: 1.64g/cm³
• LogP: 2.48220

Purity/Quality:

99% ^*data from raw suppliers

Viridicatumtoxin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: Viridicatumtoxin in a mycotoxin originally isolated from Penicillium that has diverse biological activities, including antimicrobial, cytotoxic, and toxic properties. It inhibits the growth of B. subtilis, M. luteus, C. perfringens, B. fragilis, and methicillin-resistant S. aureus (MRSA; MICs = 0.39-1.56 μg/ml), as well as C. albicans, S. cerevisiae, M. racemosus, A. niger, and P. chrysogenum (MICs = 6.2-25 μg/ml), but has no activity against M. smegmatis, E. coli, K. pneumoniae, P. aeruginosa, or S. marcescens (MICs = >100 μg/ml). Viridicatumtoxin inhibits the production of polyprenyl alcohols by S. aureus undecaprenyl pyrophosphate (UPP) synthase, E. coli octaprenyl pyrophosphate synthase (OPS), and S. cerevisiae dehydrodolichyl pyrophosphate (DedoIPP) synthase in vitro (IC50s = 3.1, 21, and 71 μM, respectively). It has cytotoxic effects against human Jurkat T (IC50 = 4.92 μM), chronic lymphocytic leukemia (CLL; LC50 = 0.7-3.5 nM), and bone marrow-derived HS-5 stromal cells. Viridicatumtoxin is toxic to rats and mice when administered intraperitoneally (LD50s = 80 and 90 mg/kg, respectively) and to rats when administered via gastric intubation (LD50 = 122.4 mg/kg), but not to rats or mice when administered orally or through subcutaneous injection.
• Uses: Viridicatumtoxin is a tetracycline-like metabolite produced by several species of Penicillium. Viridicatumtoxin is a tetracycline-like metabolite produced by several species of Penicillium, first isolated in 1976 as a mycotoxin. Initial testing revealed that viridicatumtoxin caused myocardial deterioration, renal tubule necrosis and spleen atrophy. Analogous to the related tetracyclines, viridicatumtoxin was found to be a potent antibacterial, with activity against S. aureus including MRSA and QRSA strains. Little has been published on the mode of action of viridicatumtoxin.

Technology Process of viridicatumtoxin

There total 1 articles about viridicatumtoxin 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:

previridicatumtoxin → viridicatumtoxin (39277-41-3)

Guidance literature:

With cytochrome P₄₅₀ enzyme VrtK; Enzymatic reaction;

DOI:10.1021/ja408966t

Refernces