Record Information
Version1.0
Creation Date2010-05-20 16:06:57 UTC
Update Date2026-04-05 15:23:41 UTC
Accession NumberCHEM002734
Identification
Common NameLolitrem B
ClassSmall Molecule
DescriptionPaspalinine is a tremorgenic mycotoxin that is produced by the fungi Neotyphodium lolii and Acremonium lolii. 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" or “ryegrass staggers”. (1, 2, 4)
Contaminant Sources
  • T3DB toxins
Contaminant Type
  • Ester
  • Ether
  • Fungal Toxin
  • Mycotoxin
  • Natural Compound
  • Organic Compound
Chemical Structure
Thumb
SynonymsNot Available
Chemical FormulaC42H55NO7
Average Molecular Mass685.889 g/mol
Monoisotopic Mass685.398 g/mol
CAS Registry Number81771-19-9
IUPAC Name22-hydroxy-1,10,10,12,12,30,30,36-octamethyl-28-(2-methylprop-1-en-1-yl)-11,24,27,29,32-pentaoxa-3-azadecacyclo[17.17.0.0²,¹⁷.0⁴,¹⁶.0⁷,¹⁵.0⁹,¹³.0²²,³⁶.0²³,²⁵.0²³,³³.0²⁶,³¹]hexatriaconta-2(17),4(16),5,7(15)-tetraen-8-one
Traditional Name22-hydroxy-1,10,10,12,12,30,30,36-octamethyl-28-(2-methylprop-1-en-1-yl)-11,24,27,29,32-pentaoxa-3-azadecacyclo[17.17.0.0²,¹⁷.0⁴,¹⁶.0⁷,¹⁵.0⁹,¹³.0²²,³⁶.0²³,²⁵.0²³,³³.0²⁶,³¹]hexatriaconta-2(17),4(16),5,7(15)-tetraen-8-one
SMILESCC(C)=CC1OC2C3OC33C(CCC4(C)C5(C)C(CC6=C5NC5=C6C6=C(C=C5)C(=O)C5C(C6)C(C)(C)OC5(C)C)CCC34O)OC2C(C)(C)O1
InChI IdentifierInChI=1S/C42H55NO7/c1-20(2)17-28-47-32-34(38(7,8)48-28)46-27-14-15-39(9)40(10)21(13-16-41(39,45)42(27)35(32)49-42)18-24-29-23-19-25-30(37(5,6)50-36(25,3)4)31(44)22(23)11-12-26(29)43-33(24)40/h11-12,17,21,25,27-28,30,32,34-35,43,45H,13-16,18-19H2,1-10H3
InChI KeyHGBZMCXKHKZYBF-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
  • Naphthofuran
  • Naphthalene
  • Tetralin
  • 3-alkylindole
  • Indole
  • Indole or derivatives
  • Aryl alkyl ketone
  • Aryl ketone
  • 1,4-dioxepane
  • Dioxepane
  • Meta-dioxane
  • Monosaccharide
  • Oxane
  • Pyran
  • Benzenoid
  • Cyclic alcohol
  • Pyrrole
  • Tertiary alcohol
  • Tetrahydrofuran
  • Heteroaromatic compound
  • Ketone
  • Acetal
  • Dialkyl ether
  • Oxirane
  • Ether
  • Oxacycle
  • Azacycle
  • Organic nitrogen compound
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organooxygen compound
  • 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 Solubility0.00022 g/LALOGPS
logP5.75ALOGPS
logP6.51ChemAxon
logS-6.5ALOGPS
pKa (Strongest Acidic)13.15ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area102.54 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity189.22 m³·mol⁻¹ChemAxon
Polarizability79.94 ųChemAxon
Number of Rings10ChemAxon
Bioavailability0ChemAxon
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, Positivesplash10-000i-1000019000-66132e6b0615956284e7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004l-7500059000-911c3fa783cecc676d27Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-066r-9000161000-cc41dc0c2503d27116dbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0000019000-435251defe06ce871327Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0uyi-3100059000-7d2634584c9c4489b12dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0apl-9300052000-5c3596e8eb34d48ec6ccSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000009000-9ac32f594a0080abf166Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fri-2000019000-8744ed0236dca05eac59Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000f-9110035000-9bae12f1443f21c69d37Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0000009000-dd2f6c392bd7721a00f1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0000009000-e9e00ac78c08bd2e0a36Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-1120119000-9011ab8bd05cd587d4e7Spectrum
Toxicity Profile
Route of ExposureOral, dermal, inhalation, and parenteral (contaminated drugs). (5)
Mechanism of ToxicityThe neurological effects of Lolitrem B are a result of its ability to inhibit large conductance calcium-activated potassium channels (BK channels). Lolitrem B binds to the alpha subunit of the BK channel, inhibiting channel potassium currents. This causes tremorgenic effects either by directly affecting channels in the muscle or by acting on channels in the central nervous system. (2, 3)
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesLolitrem B is a tremorgenic mycotoxin that is produced by the fungi Neotyphodium lolii and Acremonium lolii. It may be found in contaminated cereal crops such as oats, barley, millet, corn and rice. (1, 2, 4)
Minimum Risk LevelSymptoms of "ryegrass staggers" develop in livestock when concentrations exceed 2.5 ug/g in dry matter. (4)
Health EffectsTremorgenic mycotoxins affect central nervous system activity. They cause a neurological disease of cattle known as "staggers syndrome" or “ryegrass staggers”. (1, 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" or “ryegrass staggers”, which is characterized by impaired motor coordination, muscle tremors, hyperexcitability, convulsions, and ataxia. Additional symptoms include increased blood pressure, heart rate and respiration rate. While the neurotoxic effects of lolitrem B have a long duration, they are also reversible. (1, 2, 3, 4)
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. (6)
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0242426
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkLolitrem B
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID73150453
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26.