Verruculogen (CHEM002746)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (28)XML
Record Information
Version1.0
Creation Date2010-06-10 15:41:06 UTC
Update Date2026-04-06 02:27:01 UTC
Accession NumberCHEM002746
Identification
Common NameVerruculogen
ClassSmall Molecule
DescriptionVerruculogen 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. Tremorgenic mycotoxins affect central nervous system activity and have been implicated in a number of neurologic diseases of cattle collectively known as "staggers syndromes". (2)
Contaminant Sources
  • T3DB toxins
Contaminant Type
  • Amide
  • Amine
  • Ether
  • Fungal Toxin
  • Mycotoxin
  • Natural Compound
  • Organic Compound
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
SynonymsNot Available
Chemical FormulaC27H33N3O7
Average Molecular Mass511.567 g/mol
Monoisotopic Mass511.232 g/mol
CAS Registry Number12771-72-1
IUPAC Name23,24-dihydroxy-5-methoxy-12,12-dimethyl-9-(2-methylprop-1-en-1-yl)-10,11-dioxa-8,15,21-triazahexacyclo[12.10.1.0²,⁷.0⁸,²⁵.0¹⁵,²³.0¹⁷,²¹]pentacosa-1(25),2(7),3,5-tetraene-16,22-dione
Traditional Name23,24-dihydroxy-5-methoxy-12,12-dimethyl-9-(2-methylprop-1-en-1-yl)-10,11-dioxa-8,15,21-triazahexacyclo[12.10.1.0²,⁷.0⁸,²⁵.0¹⁵,²³.0¹⁷,²¹]pentacosa-1(25),2(7),3,5-tetraene-16,22-dione
SMILESCOC1=CC2=C(C=C1)C1=C3C(CC(C)(C)OOC(C=C(C)C)N23)N2C(=O)C3CCCN3C(=O)C2(O)C1O
InChI IdentifierInChI=1S/C27H33N3O7/c1-14(2)11-20-29-18-12-15(35-5)8-9-16(18)21-22(29)19(13-26(3,4)37-36-20)30-24(32)17-7-6-10-28(17)25(33)27(30,34)23(21)31/h8-9,11-12,17,19-20,23,31,34H,6-7,10,13H2,1-5H3
InChI KeyLRXYHMMJJCTUMY-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as beta carbolines. Beta carbolines are compounds containing a 9H-pyrido[3,4-b]indole moiety.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassPyridoindoles
Direct ParentBeta carbolines
Alternative Parents
Substituents
  • Beta-carboline
  • Alpha-amino acid or derivatives
  • 3-alkylindole
  • Indole
  • Anisole
  • Dioxopiperazine
  • 2,5-dioxopiperazine
  • Alkyl aryl ether
  • N-alkylpiperazine
  • 1,4-diazinane
  • Piperazine
  • Benzenoid
  • Tertiary carboxylic acid amide
  • Pyrrolidine
  • Pyrrole
  • Heteroaromatic compound
  • Secondary alcohol
  • Dialkyl peroxide
  • Lactam
  • Carboxamide group
  • Oxacycle
  • Alkanolamine
  • Azacycle
  • Ether
  • Carboxylic acid derivative
  • Organooxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.18 g/LALOGPS
logP1.72ALOGPS
logP2.43ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)10.13ChemAxon
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area113.7 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity133.03 m³·mol⁻¹ChemAxon
Polarizability54.71 ųChemAxon
Number of Rings6ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-1000390000-06960e48023870a5a6fdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01vo-9000720000-54a03b1c30fee56ff7aaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0g4m-9000000000-ef61f644fec3fdce5974Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-1000390000-682343583a758eb772c6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-06sc-9008410000-b0d20ddea1ac07aea0d8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9001000000-e322e9b4e4ce3f9875f1Spectrum
Toxicity Profile
Route of ExposureOral, dermal, inhalation, and parenteral (contaminated drugs). (5)
Mechanism of ToxicityTremorgenic 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. In addition, verruculogen inhibits presynaptic high-conductance Ca+2 activated maxi-K+ channels in the smooth muscle. Verruculogen is also genotoxic and causes DNA damage. (2, 3, 4)
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesVerruculogen 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 LevelNot Available
Health EffectsTremorgenic mycotoxins affect central nervous system activity. They cause a neurological disease of cattle known as "staggers syndrome". (2)
SymptomsTremorgenic 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)
TreatmentTo 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
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkVerruculogen
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID104862
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available