Record Information
Version1.0
Creation Date2010-06-10 15:41:04 UTC
Update Date2026-04-06 10:42:42 UTC
Accession NumberCHEM002742
Identification
Common NamePaspalitrem B
ClassSmall Molecule
DescriptionPaspalitrem B 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
  • Ester
  • Fungal Toxin
  • Mycotoxin
  • Natural Compound
  • Organic Compound
Chemical Structure
Thumb
SynonymsNot Available
Chemical FormulaC32H39NO5
Average Molecular Mass517.656 g/mol
Monoisotopic Mass517.283 g/mol
CAS Registry Number63764-58-9
IUPAC Name19-hydroxy-11-[(1E)-3-hydroxy-3-methylbut-1-en-1-yl]-4,5,24,24-tetramethyl-25,26-dioxa-7-azaheptacyclo[21.2.1.0¹,²⁰.0⁴,¹⁹.0⁵,¹⁶.0⁶,¹⁴.0⁸,¹³]hexacosa-6(14),8(13),9,11,20-pentaen-22-one
Traditional Name19-hydroxy-11-[(1E)-3-hydroxy-3-methylbut-1-en-1-yl]-4,5,24,24-tetramethyl-25,26-dioxa-7-azaheptacyclo[21.2.1.0¹,²⁰.0⁴,¹⁹.0⁵,¹⁶.0⁶,¹⁴.0⁸,¹³]hexacosa-6(14),8(13),9,11,20-pentaen-22-one
SMILESCC(C)(O)\C=C\C1=CC2=C(NC3=C2CC2CCC4(O)C5=CC(=O)C6OC5(CCC4(C)C32C)OC6(C)C)C=C1
InChI IdentifierInChI=1S/C32H39NO5/c1-27(2,35)11-9-18-7-8-22-20(15-18)21-16-19-10-12-31(36)24-17-23(34)26-28(3,4)38-32(24,37-26)14-13-29(31,5)30(19,6)25(21)33-22/h7-9,11,15,17,19,26,33,35-36H,10,12-14,16H2,1-6H3/b11-9+
InChI KeyBZJWARDOYGJZHQ-PKNBQFBNSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassNaphthopyrans
Sub ClassNot Available
Direct ParentNaphthopyrans
Alternative Parents
Substituents
  • Naphthopyran
  • 3-alkylindole
  • Naphthalene
  • Indole or derivatives
  • Indole
  • Styrene
  • Ketal
  • Dihydropyranone
  • Benzenoid
  • Pyran
  • Heteroaromatic compound
  • Tertiary alcohol
  • Pyrrole
  • Cyclic alcohol
  • Meta-dioxolane
  • Ketone
  • Oxacycle
  • Azacycle
  • Acetal
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Alcohol
  • 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
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00035 g/LALOGPS
logP4.62ALOGPS
logP4.91ChemAxon
logS-6.2ALOGPS
pKa (Strongest Acidic)13.6ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area91.78 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity147.48 m³·mol⁻¹ChemAxon
Polarizability59.82 ųChemAxon
Number of Rings7ChemAxon
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, Positivesplash10-0ue9-0000790000-719f5ac0539f9ab20e1dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f8c-0000930000-ce74e155e200e20b3207Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000x-0153900000-6748b97b456dbe005eb4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000390000-9fc838d96180fc0d2de2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014j-0000960000-d1dc74c2631107d37111Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ff0-1203920000-0404886b8453920de4aeSpectrum
Toxicity Profile
Route of ExposureOral, dermal, inhalation, and parenteral (contaminated drugs). (4)
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, paspalitrem B inhibits presynaptic high-conductance Ca+2 activated maxi-K+ channels in the smooth muscle. (2, 3)
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesPaspalitrem B 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 LinkNot Available
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound IDNot Available
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available