Verrucarin A (CED0012476)

Record Information

Version

1.0

Creation Date

2010-04-28 21:43:36 UTC

Update Date

2026-03-31 20:47:18 UTC

SynCED ID

CED0012476

Secondary Accession Numbers

CHEM002689
T3D3720

Identification

Common Name

Verrucarin A

Class

Small Molecule

Description

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.

Contaminant Type

Ester
Ether
Fungal Toxin
Lachrymator
Mycotoxin
Natural Compound
Organic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Verrucarin a	MeSH
Muconomycin a	MeSH

Chemical Formula

C₂₇H₃₄O₉

Average Molecular Mass

502.560 g/mol

Monoisotopic Mass

502.220 g/mol

CAS Registry Number

3148-09-2

IUPAC Name

(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

Traditional Name

(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

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

InChI Identifier

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+

InChI Key

NLUGUZJQJYVUHS-YDFGWWAZSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as trichothecenes. These are sesquiterpene mycotoxins structurally characterized by the presence of an epoxide ring and a benzopyran derivative with a variant number of hydroxyl, acetyl, or other substituents. The most important structural features causing the biological activities of trichothecenes are the 12,13-epoxy ring, the presence of hydroxyl or acetyl groups at appropriate positions on the trichothecene nucleus and the structure and position of the side-chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Trichothecenes

Alternative Parents

Substituents

Trichothecene skeleton
Macrolide
Tricarboxylic acid or derivatives
Oxepane
Oxane
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Secondary alcohol
Lactone
Carboxylic acid ester
Organoheterocyclic compound
Oxacycle
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organic oxygen compound
Carbonyl group
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.043 g/L	ALOGPS
logP	2.2	ALOGPS
logP	2.55	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	12.48	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	120.89 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	128.51 m³·mol⁻¹	ChemAxon
Polarizability	51.37 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0pb9-0146920000-44bc9a93a6d76fd43811	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-052k-9264100000-4a38072f75d7e4478dff	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0002-7390000000-99c85d374174b47c6915	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014i-9124320000-cfcf9f2fd9723b53c9f6	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a59-6778910000-523410537139d4211705	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0g4l-6900000000-05fb7572e18ed4e2066f	Not Available	View Spectrum

Toxicity Profile

Toxicity Values

Toxicity Value	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Toxicity Rating	Reference
0.8 mg/kg	Rat	LD50	Intravenous	experimental	Not Available	9
234.0 Log mg/kg [130:420]	Rat	LD50	oral	predicted	Not Available	Not Available

Toxicity / Toxin Class

Not Available

Mechanism of Toxicity

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. (8, 9, 2, 3, 4, 5)

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Minimum Risk Level

Not Available

Symptoms

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. (8, 9)

Treatment

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. (1)

Health Effects

Health Effect	Relationship	Direction	Description	Reference

Exposure Sources

Source ID	Source	Sector	Reference
CEDs000306	Antibiotics?Antibiotics are synthetic or semi-synthetic compounds used to treat bacterial infections in humans and animals.	Healthcare, pharmaceuticals & veterinary products	Not Available
CEDs000506	Antennas?Antennas, commonly used in communication technologies, can be a source of synthetic chemical contamination through the materials and coatings used in their construction.	Electrical & Electronic Equipment	PubChem
CEDs000511	Conductors Or Conductive Bodies Characterised By The Conductive Materials?Conductors, or conductive bodies, are materials that allow the flow of electrical current, typically made from metals such as copper, aluminum, or silver.	Electrical & Electronic Equipment	PubChem
CEDs000514	Discharge Lamps?Discharge lamps, including fluorescent and high-intensity discharge (HID) lamps, are commonly used for lighting applications due to their energy efficiency and brightness.	Electrical & Electronic Equipment	PubChem
CEDs000521	Fixed Capacitors And Their Manufacture?Fixed capacitors are passive electronic components used to store and release electrical energy, playing a critical role in various circuits.	Electrical & Electronic Equipment	PubChem
CEDs000545	Food Preservation?Food preservation often involves the use of synthetic chemicals, such as preservatives, flavor enhancers, and color additives, to extend shelf life and enhance the sensory qualities of food products.	Food, food processing & cookware	PubChem
CEDs000555	Bleaching Agents?Bleaching agents are chemical substances used to whiten or lighten materials, often employed in various cleaning products for their stain removal and disinfecting properties.	Household cleaning & consumer products	PubChem
CEDs000580	Manufacture Preparation Of Tobacco Products?The manufacture and preparation of tobacco products involve various processes that can result in the introduction of synthetic chemicals into the environment.	Industrial manufacturing & chemical processing	PubChem
CEDs000652	Ropes?Ropes manufactured from synthetic fibers, such as polypropylene, nylon, and polyester, are widely used in various applications, including marine, construction, and outdoor activities.	Textiles, leather & furnishings	PubChem
CEDs000691	Non Oxide Glass?Non-oxide glass refers to a category of glasses primarily composed of materials other than silicon dioxide, such as boron oxide or phosphorous oxide.	Building & Construction	PubChem
CEDs000696	Nanotechnology?Nanotechnology involves the manipulation of materials at the molecular or atomic level, typically within the range of 1 to 100 nanometers.	Industrial manufacturing & chemical processing	PubChem
CEDs000735	Explosives?Explosives are chemical compounds or mixtures designed to undergo rapid decomposition, releasing energy in the form of gas and heat.	Defense & military infrastructure	PubChem

Pathways

0 pathwaysPathway Source: PathBank

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Neurogenic locus notch homolog protein 1	Q01705	Mus musculus	Predicted (SEA)	Prediction Confidence Score 0.205 Applicability Domain 0.205 Low confidence Statistical Significance 9.70e-04 Supporting Reference Compounds 1 E-value 7.55137
Click to view 3D structure	Phospholipase A2 alpha	P00623	Crotalus adamanteus	Predicted (SEA)	Prediction Confidence Score 0.202 Applicability Domain 0.202 Low confidence Statistical Significance 2.60e-04 Supporting Reference Compounds 1 E-value 2.02408
Click to view 3D structure	Kappa-type opioid receptor	P41145	Humans	Predicted (SEA)	Prediction Confidence Score 0.198 Applicability Domain 0.212 Low confidence Statistical Significance 0.759 Supporting Reference Compounds 532 E-value 5908.52
Click to view 3D structure	Serine/threonine-protein phosphatase 2A 65 kDa regulatory subunit A alpha isoform	Q76MZ3	Mus musculus	Predicted (SEA)	Prediction Confidence Score 0.191 Applicability Domain 0.191 Low confidence Statistical Significance 2.10e-04 Supporting Reference Compounds 1 E-value 1.63483
Click to view 3D structure	Signal transducer and activator of transcription 3	P40763	Humans	Predicted (SEA)	Prediction Confidence Score 0.186 Applicability Domain 0.208 Low confidence Statistical Significance 0.5308 Supporting Reference Compounds 93 E-value 4132.16
Click to view 3D structure	Sex hormone-binding globulin	P04278	Humans	Predicted (SEA)	Prediction Confidence Score 0.185 Applicability Domain 0.2 Low confidence Statistical Significance 0.0135 Supporting Reference Compounds 33 E-value 105.408
Click to view 3D structure	Glucocorticoid receptor	P04150	Humans	Predicted (SEA)	Prediction Confidence Score 0.185 Applicability Domain 0.198 Low confidence Statistical Significance 0.5272 Supporting Reference Compounds 154 E-value 4104.37
Click to view 3D structure	Androgen receptor	P15207	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.185 Applicability Domain 0.198 Low confidence Statistical Significance 0.1292 Supporting Reference Compounds 73 E-value 1005.66
Click to view 3D structure	Progesterone receptor	Q690N0	Bos taurus	Predicted (SEA)	Prediction Confidence Score 0.185 Applicability Domain 0.198 Low confidence Statistical Significance 0.0248 Supporting Reference Compounds 40 E-value 193.222
Click to view 3D structure	Mu-type opioid receptor	P35372	Humans	Predicted (SEA)	Prediction Confidence Score 0.184 Applicability Domain 0.212 Low confidence Statistical Significance 0.8635 Supporting Reference Compounds 527 E-value 6722.44
Click to view 3D structure	G-protein coupled receptor 55	Q9Y2T6	Humans	Predicted (SEA)	Prediction Confidence Score 0.183 Applicability Domain 0.207 Low confidence Statistical Significance 0.6018 Supporting Reference Compounds 125 E-value 4685.28
Click to view 3D structure	Phospholipase A2	P00630	Apis mellifera	Predicted (SEA)	Prediction Confidence Score 0.182 Applicability Domain 0.204 Low confidence Statistical Significance 0.001 Supporting Reference Compounds 9 E-value 7.86277
Click to view 3D structure	Bile salt export pump	O95342	Humans	Predicted (SEA)	Prediction Confidence Score 0.181 Applicability Domain 0.208 Low confidence Statistical Significance 0.6016 Supporting Reference Compounds 104 E-value 4683.49
Click to view 3D structure	Tegument protein VP16	P06492	Herpes simplex virus (type 1 / strain 17)	Predicted (SEA)	Prediction Confidence Score 0.181 Applicability Domain 0.22 Low confidence Statistical Significance 0.5027 Supporting Reference Compounds 75 E-value 3913.32
Click to view 3D structure	Delta-type opioid receptor	P41143	Humans	Predicted (SEA)	Prediction Confidence Score 0.181 Applicability Domain 0.212 Low confidence Statistical Significance 0.8327 Supporting Reference Compounds 427 E-value 6482.19
Click to view 3D structure	Androgen receptor	P10275	Humans	Predicted (SEA)	Prediction Confidence Score 0.18 Applicability Domain 0.198 Low confidence Statistical Significance 0.6132 Supporting Reference Compounds 146 E-value 4773.4
Click to view 3D structure	ATP-dependent clpX-like chaperone, mitochondrial	O76031	Humans	Predicted (SEA)	Prediction Confidence Score 0.18 Applicability Domain 0.18 Low confidence Statistical Significance 0.004 Supporting Reference Compounds 1 E-value 30.9061
Click to view 3D structure	Mineralocorticoid receptor	P08235	Humans	Predicted (SEA)	Prediction Confidence Score 0.18 Applicability Domain 0.198 Low confidence Statistical Significance 0.4079 Supporting Reference Compounds 74 E-value 3175.16
Click to view 3D structure	Phospholipase A2, membrane associated	P14555	Humans	Predicted (SEA)	Prediction Confidence Score 0.18 Applicability Domain 0.202 Low confidence Statistical Significance 0.3146 Supporting Reference Compounds 49 E-value 2449.45
Click to view 3D structure	Delta-type opioid receptor	P32300	Mus musculus	Predicted (SEA)	Prediction Confidence Score 0.179 Applicability Domain 0.212 Low confidence Statistical Significance 0.3741 Supporting Reference Compounds 166 E-value 2912.65
Click to view 3D structure	Mu-type opioid receptor	P33535	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.179 Applicability Domain 0.212 Low confidence Statistical Significance 0.5184 Supporting Reference Compounds 229 E-value 4035.94
Click to view 3D structure	Phospholipase A2	B7UUK1	Apis mellifera	Predicted (SEA)	Prediction Confidence Score 0.179 Applicability Domain 0.202 Low confidence Statistical Significance 4.90e-04 Supporting Reference Compounds 3 E-value 3.81461
Click to view 3D structure	Progesterone receptor	P06401	Humans	Predicted (SEA)	Prediction Confidence Score 0.179 Applicability Domain 0.198 Low confidence Statistical Significance 0.6169 Supporting Reference Compounds 119 E-value 4802.67
Click to view 3D structure	Prostaglandin G/H synthase 2	P35354	Humans	Predicted (SEA)	Prediction Confidence Score 0.179 Applicability Domain 0.211 Low confidence Statistical Significance 0.7332 Supporting Reference Compounds 201 E-value 5707.59
Click to view 3D structure	Acidic phospholipase A2 2	P15445	Naja naja	Predicted (SEA)	Prediction Confidence Score 0.178 Applicability Domain 0.18 Low confidence Statistical Significance 4.70e-04 Supporting Reference Compounds 3 E-value 3.65891
Click to view 3D structure	Transient receptor potential cation channel subfamily A member 1	O75762	Humans	Known	Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

Not Available

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

Not Available

ChEBI ID

Not Available

PubChem Compound ID

6437060

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Grond S, Sablotzki A: Clinical pharmacology of tramadol. Clin Pharmacokinet. 2004;43(13):879-923. [PubMed: 15509185]
Pestka JJ: Mechanisms of deoxynivalenol-induced gene expression and apoptosis. Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2008 Sep;25(9):1128-40. [PubMed: 19238623]
Nusuetrong P, Pengsuparp T, Meksuriyen D, Tanitsu M, Kikuchi H, Mizugaki M, Shimazu K, Oshima Y, Nakahata N, Yoshida M: Satratoxin H generates reactive oxygen species and lipid peroxides in PC12 cells. Biol Pharm Bull. 2008 Jun;31(6):1115-20. [PubMed: 18520041]
Rocha O, Ansari K, Doohan FM: Effects of trichothecene mycotoxins on eukaryotic cells: a review. Food Addit Contam. 2005 Apr;22(4):369-78. [PubMed: 16019807]
Bae HK, Pestka JJ: Deoxynivalenol induces p38 interaction with the ribosome in monocytes and macrophages. Toxicol Sci. 2008 Sep;105(1):59-66. doi: 10.1093/toxsci/kfn102. Epub 2008 May 22. [PubMed: 18502741]
Peraica M, Domijan AM: Contamination of food with mycotoxins and human health. Arh Hig Rada Toksikol. 2001 Mar;52(1):23-35. [PubMed: 11370295]
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
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.

Verrucarin A (CED0012476)

Structure for CHEM002689: Verrucarin A

No pathways found

Structure