ChemicalBook--->CAS DataBase List--->3148-09-2

3148-09-2

3148-09-2 Structure

3148-09-2 Structure
IdentificationBack Directory
[Name]

MUCONOMYCIN A
[CAS]

3148-09-2
[Synonyms]

vera
Verrucarin
NSC 126728
VERRUCARIN A
MUCONOMYCIN A
Muconomycin A, NSC 126728
16a,21-trimethyl--stereoisomer
verrucarin A from myrothecium sp
n-17(18h),2’-oxirane)-3,9,14-trione,4,5,6,7,16,16a,19a,22-octahydro-4-hydroxy
spiro(16,18-methano-1h,3h,23h-(1,6,12)trioxacyclooctadecino(3,4-d)(1)benzopyra
[Molecular Formula]

C27H34O9
[MDL Number]

MFCD00056759
[MOL File]

3148-09-2.mol
[Molecular Weight]

502.55
Chemical PropertiesBack Directory
[Melting point ]

>360° (dec)
[alpha ]

D23 +206° (c = 1.012 in chloroform)
[Boiling point ]

512.66°C (rough estimate)
[density ]

1.1922 (rough estimate)
[refractive index ]

1.5500 (estimate)
[storage temp. ]

−20°C
[solubility ]

Dichloromethane: soluble,DMSO: soluble,Ethanol: soluble,Methanol: soluble
[form ]

A solid
[pka]

12.76±0.70(Predicted)
Safety DataBack Directory
[Hazard Codes ]

T+
[Risk 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
[HS Code ]

2941900000
[Toxicity]

LD50 in mice, rats, rabbits (mg/kg): 1.5, 0.87, 0.54 i.v. (Rüsch, Sthlin)
Hazard InformationBack Directory
[Uses]

Verrucarin A from Myrothecium sp has been used:
  • as a translation initiation inhibitor in P. falciparum W2 strain
  • as a peptidyl transfer inhibitor to test sensitivity in methyltransferase knock-out S. cerevisiae cells
  • to test its cytotoxicity in renal cell carcinoma cells

[Definition]

ChEBI: A trichothecene antibiotic which incorporates a triester macrocyclic structure and an exocyclic methylene epoxide group.
[General Description]

Verrucarin derived from the Myrothecium verrucari, a fungal plant pathogen is a macrocyclic trichothecene compound.
[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
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