1.0 2010-04-28 21:43:36 UTC 2026-03-31 20:47:18 UTC T3D3720 Verrucarin A SmallMolecule Verrucarin A is an exogenous solid with the formula C27H34O9. Verrucarin A belongs to the sesquiterpenoids, a subclass of prenol lipids within the organic compounds. With an average molecular weight of 502.56 g/mol, Verrucarin A is a heavy molecule. This compound is found in or released from healthcare, pharmaceuticals & veterinary products (antibiotics) and electrical & electronic equipment (antennas), with recorded exposure routes via oral and inhalation. The compound targets Transient receptor potential cation channel subfamily A member 1 (TRPA1) and an unnamed protein. As a trichothecene, it moves freely across the plasma membrane to bind specifically to ribosomes with high-affinity. It interferes with the active site of peptidyl transferase at the 3'-end of large 28S ribosomal RNA, inhibiting the initiation, elongation, or termination step of protein synthesis and causing polyribosomal disaggregation. Because protein synthesis is an essential function in all tissues, these actions render trichothecenes cytotoxic. Fungal Toxin Natural Toxin Organic Compound Ether Ester Mycotoxin Lachrymator Fungal Toxin Natural Compound Muconomycin A Spiro(16,18-methano-1H,3H,23H-(1,6,12)trioxacyclooctadecino(3,4-d)(1)benzopyran-17(18H),2'-oxirane)-3,9,14-trione, 4,5,6,7,16,16a,19a,22-octahydro-4-hydroxy-5,16a,21-trimethyl-, stereoisomer VER A Verrucarin a Verrucarin A (8CI) Verrucarin A (8CI)(9CI) C27H34O9 502.56 502.220282675 (18'E,20'E)-12'-hydroxy-5',13',25'-trimethyl-2',10',16',23'-tetraoxaspiro[oxirane-2,26'-tetracyclo[22.2.1.0³,⁸.0⁸,²⁵]heptacosane]-4',18',20'-triene-11',17',22'-trione (18'E,20'E)-12'-hydroxy-5',13',25'-trimethyl-2',10',16',23'-tetraoxaspiro[oxirane-2,26'-tetracyclo[22.2.1.0³,⁸.0⁸,²⁵]heptacosane]-4',18',20'-triene-11',17',22'-trione 3148-09-2 [H]/C1=C([H])\C(=O)OCCC(C)C(O)C(=O)OCC23CCC(C)=CC2OC2CC(OC(=O)\C([H])=C\1/[H])C3(C)C21CO1 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+ NLUGUZJQJYVUHS-YDFGWWAZSA-N Organic compounds Lipids and lipid-like molecules Prenol lipids Sesquiterpenoids Trichothecenes Carbonyl compounds Dialkyl ethers Enoate esters Epoxides Hydrocarbon derivatives Lactones Macrolides and analogues Organic oxides Oxacyclic compounds Oxanes Oxepanes Secondary alcohols Tricarboxylic acids and derivatives Alcohol Aliphatic heteropolycyclic compound Alpha,beta-unsaturated carboxylic ester Carbonyl group Carboxylic acid derivative Carboxylic acid ester Dialkyl ether Enoate ester Ether Hydrocarbon derivative Lactone Macrolide Organic oxide Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Oxane Oxepane Oxirane Secondary alcohol Tricarboxylic acid or derivatives Trichothecene skeleton Aliphatic heteropolycyclic compounds Detected and Not Quantified Exogenous Membrane Solid White powder. logp 2.20 ALOGPS logs -4.07 ALOGPS solubility 4.28e-02 g/l ALOGPS logp 2.55 ChemAxon pka_strongest_acidic 12.48 ChemAxon pka_strongest_basic -3.9 ChemAxon iupac (18'E,20'E)-12'-hydroxy-5',13',25'-trimethyl-2',10',16',23'-tetraoxaspiro[oxirane-2,26'-tetracyclo[22.2.1.0³,⁸.0⁸,²⁵]heptacosane]-4',18',20'-triene-11',17',22'-trione ChemAxon average_mass 502.56 ChemAxon mono_mass 502.220282675 ChemAxon smiles [H]/C1=C([H])\C(=O)OCCC(C)C(O)C(=O)OCC23CCC(C)=CC2OC2CC(OC(=O)\C([H])=C\1/[H])C3(C)C21CO1 ChemAxon formula C27H34O9 ChemAxon 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+ ChemAxon inchikey NLUGUZJQJYVUHS-YDFGWWAZSA-N ChemAxon polar_surface_area 120.89 ChemAxon refractivity 128.51 ChemAxon polarizability 51.37 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 6 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Oral, dermal, inhalation, and parenteral (contaminated drugs). (A3101) Unlike many other mycotoxins, trichothecenes do not require metabolic activation to exert their biological activity, instead directly reacting with cellular components. Trichothecenes are cytotoxic to most eukaryotic cells due to their powerful ability to inhibit protein synthesis. They do this by freely moving across the plasma membrane and binding specifically to ribosomes with high-affinity. Specifically, they interfere with the active site of peptidyl transferase at the 3'-end of large 28S ribosomal RNA and inhibit the initiation, elongation or termination step of protein synthesis, as well as cause polyribosomal disaggregation. Protein synthesis is an essential function in all tissues, but tissues where cells are actively and rapidly growing and dividing are very susceptible to the toxins. Additionally, binding to ribosomes is thought to activate proteins in downstream signalling events related to immune response and apoptosis, such as mitogen-activated protein kinases. This is known as ribotoxic stress response. Trichothecenes may also induce some alterations in membrane structure, leading to increased lipid peroxidation and inhibition of electron transport activity in the mitochondria. They can further induce apoptosis through generation of reactive oxygen species. Further secondary effects of trichothecenes include inhibition of RNA and DNA synthesis, and also inhibition of mitosis. (L1948, L1949, A2962, A2963, A2964, A2980) Trichothecenes are lipophilic and thus easily absorbed through the skin, gut, and pulmonary mucosa. They are metabolized mainly by cytochrome P-450 and trichothecene-specific carboxylesterase activity in the liver, although other tissues such as the kidney, spleen, and intestine also show some metabolic activity. Trichothecenes are metabolically transformed to less toxic metabolites by such reactions as hydrolysis, hydroxylation, de-epoxidation, and glucuronidation. Metabolites are excreted in the urine and feces. (L1910, L1949) LD50: 0.8 mg/kg (Intravenous, Rat) (L1949) No indication of carcinogenicity to humans (not listed by IARC). Trichothecenes are a very large family of chemically related mycotoxins produced by various species of Fusarium, Myrothecium, Trichoderma, Trichothecium, Cephalosporium, Verticimonosporium, and Stachybotrys. They are produced on many different grains like wheat, oats or maize by various Fusarium species such as F. graminearum, F. sporotrichioides, F. poae and F. equiseti. Some molds that produce trichothecene mycotoxins, such as Stachybotrys chartarum, can grow in damp indoor environments and may contribute to health problems among building occupants. (L1948) #<HealthEffect::ActiveRecord_Associations_CollectionProxy:0x00007f7227860dd0> After direct dermal application or oral ingestion, the trichothecene mycotoxins can cause rapid irritation to the skin or intestinal mucosa, including skin irritation, burning and itching, rash or blisters, and bleeding. Eye contact can cause tearing, eye pain, conjunctivitis, burning sensations about the eyes, and blurred vision for up to 1 week. Symptoms also include nausea, vomiting, fatigue, dyspnea, and acute vascular effects leading to hypotension and shock. (L1948, L1949) There are no known antidotes to trichothecene mycotoxins. Treatments are directed at supporting hemopoietic abnormalities, gastrointestinal damage, and skin damage. Administer charcoal as a slurry in case of acute oral exposure. In case of inhalation: Move patient to fresh air. Monitor for respiratory distress. If cough or difficulty breathing develops, evaluate for respiratory tract irritation, bronchitis, or pneumonitis. Administer oxygen and assist ventilation as required. Treat bronchospasm with inhaled beta2 agonist and oral or parenteral corticosteroids. In case of eye exposure, Irrigate exposed eyes with copious amounts of room temperature water for at least 15 minutes. In case of dermal exposure, Remove contaminated clothing and wash exposed area thoroughly with soap and water. (A704) 6437060 21171598 19238623 18520041 16019807 18502741 11370295 15509185 Rumack BH POISINDEX(R) Information System Micromedex, Inc., Englewood, CO, 2010; CCIS Volume 143, edition expires Feb, 2010. Hall AH & Rumack BH (Eds): TOMES(R) Information System Micromedex, Inc., Englewood, CO, 2010; CCIS Volume 143, edition expires Feb, 2010. WHO; Environ Health Criteria 105: Selected Mycotoxins: Ochratoxins, Trichothecenes, Ergot (1990).: http://www.inchem.org/documents/ehc/ehc/ehc105.htm Wikipedia. Trichothecene. Last Updated 30 March 2010.: http://en.wikipedia.org/wiki/Trichothecenes Wannemacher, R.W. JR., and Wiener, S.L. (1997). Chapter 34: Trichothecene Mycotoxins. In R. Zajtchuk (Ed.), Medical Aspects of Chemical and Biological Warfare. Maryland: Office of The Surgeon General.: http://leitl.org/docs/biowar/Ch-34.pdf BE0005432 Trichothecenes move freely across the plasma membrane and bind specifically to ribosomes with high-affinity. Specifically, they interfere with the active site of peptidyl transferase at the 3'-end of large 28S ribosomal RNA and inhibit the initiation, elongation or termination step of protein synthesis, as well as cause polyribosomal disaggregation. Trichothecenes are cytotoxic because protein synthesis is an essential function in all tissues. Additionally, binding to ribosomes is thought to activate proteins in downstream signalling events related to immune response and apoptosis, such as mitogen-activated protein kinases. This is known as ribotoxic stress response. (L1949, A2962, A2980) Wannemacher, R.W. JR., and Wiener, S.L. (1997). Chapter 34: Trichothecene Mycotoxins. In R. Zajtchuk (Ed.), Medical Aspects of Chemical and Biological Warfare. Maryland: Office of The Surgeon General.: http://leitl.org/docs/biowar/Ch-34.pdf BE0001122