3148-09-2

Basic information

• Product Name: MUCONOMYCIN A
• Synonyms: spiro(16,18-methano-1h,3h,23h-(1,6,12)trioxacyclooctadecino(3,4-d)(1)benzopyra;vera;verrucarin A from myrothecium sp;Verrucarin;Muconomycin A, NSC 126728;NSC 126728;MUCONOMYCIN A;VERRUCARIN A
• CAS NO: 3148-09-2
• Molecular Formula: C₂₇H₃₄O₉
• Molecular Weight: 488.53
• Mol File: 3148-09-2.mol
• Article Data: 2

Chemical Properties

• Melting Point: >360° (dec)
• Boiling Point: 512.66°C (rough estimate)
• Flash Point: 250.2°C
• Appearance: /
• Density: 1.1922 (rough estimate)
• Vapor Pressure: 8.74E-26mmHg at 25°C
• Refractive Index: 1.5500 (estimate)
• Storage Temp.: −20°C
• PKA: 12.76±0.70(Predicted)
• CAS DataBase Reference: MUCONOMYCIN A(CAS DataBase Reference)
• NIST Chemistry Reference: MUCONOMYCIN A(3148-09-2)
• EPA Substance Registry System: MUCONOMYCIN A(3148-09-2)

Safety Data

• Hazard Codes: T+
• Statements: 26/27/28
• Safety Statements: 22-36/37/39-45
• RIDADR: UN 2811 6.1/PG 1
• WGK Germany: 3
• RTECS: WH1314900
• HazardClass: 6.1(a)
• PackingGroup: I
• Hazardous Substances Data: 3148-09-2(Hazardous Substances Data)

Usage

Description

MUCONOMYCIN A is a macrocyclic trichothecene compound derived from the fungal plant pathogen Myrothecium verrucari. It is characterized by a unique triester macrocyclic structure and an exocyclic methylene epoxide group, which contribute to its diverse biological activities.

Uses

Used in Pharmaceutical Industry:
MUCONOMYCIN A is used as a translation initiation inhibitor for targeting the P. falciparum W2 strain, a causative agent of malaria. This property makes it a potential candidate for the development of antimalarial drugs.
Used in Genetic Research:
MUCONOMYCIN A is used as a peptidyl transfer inhibitor to test the sensitivity of methyltransferase knock-out S. cerevisiae cells. This application aids in understanding the role of peptidyl transferase in protein synthesis and its regulation.
Used in Oncology Research:
MUCONOMYCIN A is used to test its cytotoxicity in renal cell carcinoma cells. This helps in evaluating its potential as an anticancer agent and contributes to the development of novel therapeutic strategies for renal cancer treatment.

Biochem/physiol Actions

Verrucarin A binds to the P and A sites in ribosomes and blocks peptide-bond and translation initiation. It inhibits the clear cell renal cell carcinoma (CCRCC) proliferation. Verrucarin A blocks the peptidyl transferase activity and favors apoptosis induction in cancer cells

InChI:InChI=1/C27H34O9/c1-16-8-10-26-14-33-24(31)23(30)17(2)9-11-32-21(28)6-4-5-7-22(29)36-18-13-20(35-19(26)12-16)27(15-34-27)25(18,26)3/h4-7,12,17-20,23,30H,8-11,13-15H2,1-3H3/b6-4-,7-5-/t17-,18-,19-,20-,23+,25-,26-,27-/m1/s1

Upstream product

• 76739-70-3 trichoverrin A 
• 76685-82-0 trichoverrin B 
• 76685-82-0 trichoverrin B 

Downstream Products

• 74516-69-1 4β,8α,15-trihydroxy-12,13-epoxytrichothecene 
• 74516-63-5 8-oxoverrucarin A 
• 63783-99-3 4β,8β,15-trihydroxy-12,13-epoxytrichothecene 
• 74516-62-4 8α-hydroxyverrucarin A 
• 74516-64-6 16-hydroxyverrucarin A 
• 74608-63-2 8β-hydroxyverrucarin A 
• 2198-92-7 verrucarol 

Relevant articles and documents

Isolation and Characterization of the Trichoverroids and New Roridins and Verrucarins

Myrothecium verrucaria grown on a large scale (760 L) has yielded a variety of new trichothecenes including the nonmacrocyclic trichoverroids 13-19, which contain a pendant C4 cis,trans-dienic ester side chain normally common only to the macrocyclic roridins and verrucarins.Several novel macrocyclic trichothecenes (roridins J and K acetate) and verrucarins L and L acetate also were isolated and characterized.