ContaminantDB: Verrucosidin

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (48)XML

Record Information

Version

1.0

Creation Date

2010-06-10 15:41:05 UTC

Update Date

2026-04-06 11:59:40 UTC

Accession Number

CHEM002745

Identification

Common Name

Verrucosidin

Class

Small Molecule

Description

Verrucosidin is a solid exogenous organic compound with the formula C24H32O6 and an average molecular weight of 416.51 g/mol. Verrucosidin belongs to the pyranones and derivatives, a subclass of pyrans within the organic compounds. This compound is associated with 22 recorded protein targets, including 4-aminobutyrate aminotransferase, mitochondrial (ABAT), as well as Gamma-aminobutyric acid receptor subunits alpha-1 (GABRA1), alpha-2 (GABRA2), and alpha-3 (GABRA3). Tremorgenic mycotoxins are thought to inhibit gamma-aminobutyric acid (GABA) receptors, both pre- and postsynaptic, as well as inhibit transmitter breakdown at the GABA-T receptors. This mechanism would initially increase neurotransmitter levels, potentiating the GABA-induced chloride current, and subsequently lead to decreased levels of neurotransmitter in the synapse. Additionally, verrucosidin is genotoxic and causes DNA damage.

Contaminant Sources

T3DB toxins

Contaminant Type

Ester
Ether
Fungal Toxin
Mycotoxin
Natural Compound
Organic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₂₄H₃₂O₆

Average Molecular Mass

416.514 g/mol

Monoisotopic Mass

416.220 g/mol

CAS Registry Number

88389-71-3

IUPAC Name

Not Available

Traditional Name

4-methoxy-3,5-dimethyl-6-{2-methyl-3-[(2E,4E)-4-methyl-5-{2,4,5-trimethyl-3,6-dioxabicyclo[3.1.0]hexan-2-yl}penta-2,4-dien-2-yl]oxiran-2-yl}pyran-2-one

SMILES

[H]\C(\C(\C)=C(/[H])C1(C)OC(C)C2(C)OC12)=C(\C)C1OC1(C)C1=C(C)C(OC)=C(C)C(=O)O1

InChI Identifier

InChI=1S/C24H32O6/c1-12(11-22(6)21-23(7,30-21)16(5)28-22)10-13(2)18-24(8,29-18)19-14(3)17(26-9)15(4)20(25)27-19/h10-11,16,18,21H,1-9H3/b12-11+,13-10+

InChI Key

JSVLNARHSWZARV-JASOSIDASA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as pyranones and derivatives. Pyranones and derivatives are compounds containing a pyran ring which bears a ketone.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrans

Sub Class

Pyranones and derivatives

Direct Parent

Pyranones and derivatives

Alternative Parents

Substituents

Alkyl aryl ether
Pyranone
Para-dioxane
Tetrahydrofuran
Vinylogous ester
Heteroaromatic compound
Lactone
Ether
Oxirane
Dialkyl ether
Oxacycle
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

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	0.013 g/L	ALOGPS
logP	4.53	ALOGPS
logP	3.39	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	69.82 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	115.56 m³·mol⁻¹	ChemAxon
Polarizability	45.76 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0261900000-af7dba05b8ac480d577e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00p3-2892300000-a8c447be5c484b1c38e5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0aos-8930000000-aa5b160616b2ca779c74	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0222900000-fde5b532ccdd384115ec	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-05mk-5569400000-e27440ebbc7abf19b6e9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-056r-8569000000-c4c73330b859c2e718b6	Spectrum

Toxicity Profile

Route of Exposure

Oral, dermal, inhalation, and parenteral (contaminated drugs). (4)

Mechanism of Toxicity

Tremorgenic mycotoxins exert their toxic effects by interfering with neurotransmitter release, possibly by causing degeneration of nerve terminals. They are thought to inhibit gamma-aminobutyric acid (GABA) receptors, both pre- and postsynaptic, as well as inhibit transmitter breakdown at the GABA-T receptors. This would initially increase neurotransmitter levels, potentiating the GABA-induced chloride current, then lead to decreased levels of neurotransmitter in the synapse. Verrucosidin is also genotoxic and causes DNA damage. (2, 3)

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

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

Uses/Sources

Verrucosidin is a tremorgenic mycotoxin that has been found in fungi of the genera Penicillium and Aspergillus. It may be found in contaminated cereal crops such as oats, barley, millet, corn and rice. (2)

Minimum Risk Level

Not Available

Health Effects

Tremorgenic mycotoxins affect central nervous system activity. They cause a neurological disease of cattle known as "staggers syndrome". (2)

Symptoms

Tremorgenic mycotoxins affect central nervous system activity, inducing neurologic symptoms including mental confusion, paralysis, tremors, seizures, and death. They cause a neurological disease of cattle known as "staggers syndrome", which is characterized by muscle tremors, hyperexcitability, convulsions and ataxia. (2)

Treatment

To control severe tremors caused by tremorgenic mycotoxins, methocarbamol should be administered. Generalized seizures may be treated with diazepam followed by methocarbamol or a barbiturate such as pentobarbital sodium. Gastric lavage should be performed and activated charcoal administered to limit further absorption of toxins. (1)

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

10001967

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

Verrucosidin (CHEM002745)

Structure for CHEM002745: Verrucosidin