Verrucarin A

Verrucarin A
Names
	Other names Muconomycin A
Identifiers
CAS Number	3148-09-2;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:230243;
ChEMBL	ChEMBL136985;
ChemSpider	10210056;
ECHA InfoCard	100.164.324
EC Number	636-535-7;
KEGG	C09746;
PubChem CID	6326658;
UNII	OL62X66O4I;
CompTox Dashboard (EPA)	DTXSID101017607 ;
	InChI InChI=1S/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 Key: NLUGUZJQJYVUHS-IDXDZYHTSA-N;
	SMILES C[C@@H]1CCOC(=O)/C=C/C=C\C(=O)O[C@@H]2C[C@@H]3[C@]4([C@]2([C@]5(CCC(=C[C@H]5O3)C)COC(=O)[C@H]1O)C)CO4;
Properties
Chemical formula	C27H34O9
Molar mass	502.560 g·mol−1
Related compounds
Related compounds	Roridin E
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Verrucarin A is a chemical compound that belongs in the class of trichothecenes, a group of sesquiterpene toxins produced by several fungi, namely from the Fusarium species, that are responsible for infecting food grains. It was first described in 1962. Within the skeleton of the basic trichothecene structure, the olefin and epoxide are crucial for toxicity; ester functionalities and hydroxyl groups often contribute to the toxicity, thereby rendering verrucarin A as one of the most lethal examples. The mechanism of action for this class of toxins mainly inhibits protein biosynthesis by preventing peptidyl transferase activity. Although initially thought to be potentially useful as anticancer therapeutics, numerous examples of trichothecene derivatives were shown to be too toxic for clinical use.