Paspalinine (CHEM002716)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (27)XML
Record Information
Version1.0
Creation Date2010-05-10 17:05:17 UTC
Update Date2026-04-06 10:37:20 UTC
Accession NumberCHEM002716
Identification
Common NamePaspalinine
ClassSmall Molecule
DescriptionPaspalinine 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
MOLSDFPDBSMILESInChI
SynonymsNot Available
Chemical FormulaC27H31NO4
Average Molecular Mass433.539 g/mol
Monoisotopic Mass433.225 g/mol
CAS Registry Number63722-91-8
IUPAC Name19-hydroxy-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),8,10,12,20-pentaen-22-one
Traditional Name19-hydroxy-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),8,10,12,20-pentaen-22-one
SMILESCC1(C)OC23CCC4(C)C5(C)C(CC6=C5NC5=CC=CC=C65)CCC4(O)C2=CC(=O)C1O3
InChI IdentifierInChI=1S/C27H31NO4/c1-23(2)22-19(29)14-20-26(30)10-9-15-13-17-16-7-5-6-8-18(16)28-21(17)25(15,4)24(26,3)11-12-27(20,31-22)32-23/h5-8,14-15,22,28,30H,9-13H2,1-4H3
InChI KeyBPTIXFRJAOKMRK-UHFFFAOYSA-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
  • Naphthalene
  • 3-alkylindole
  • Indole
  • Indole or derivatives
  • Dihydropyranone
  • Ketal
  • Pyran
  • Benzenoid
  • Heteroaromatic compound
  • Tertiary alcohol
  • Pyrrole
  • Meta-dioxolane
  • Cyclic alcohol
  • Ketone
  • Acetal
  • Oxacycle
  • Azacycle
  • Organooxygen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Alcohol
  • Organonitrogen 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
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 Solubility0.00064 g/LALOGPS
logP4.24ALOGPS
logP4.37ChemAxon
logS-5.8ALOGPS
pKa (Strongest Acidic)13.62ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area71.55 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity121.28 m³·mol⁻¹ChemAxon
Polarizability48.61 ųChemAxon
Number of Rings7ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0159-0000900000-6e1ada03e37c784b3b01Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0159-0321900000-b7f92c83880a381e6d3eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gbc-2940100000-a7e118cb4d5ab9fe442cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0000900000-497730a462b952cb550dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01q9-0000900000-18255bea2beed0aa1770Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-1579800000-4bece89fc2e572030866Spectrum
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, paspalinine 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/SourcesPaspalinine 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 ID114727
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available