Record Information
Version1.0
Creation Date2010-05-05 17:05:00 UTC
Update Date2026-04-06 10:51:43 UTC
Accession NumberCHEM002702
Identification
Common NamePenitrem B
ClassSmall Molecule
DescriptionPenitrem B is a tremogenic toxin produced by by Penicillium aurantiogriseum
Contaminant Sources
  • T3DB toxins
Contaminant Type
  • Ether
  • Food Toxin
  • Fungal Toxin
  • Mycotoxin
  • Natural Compound
  • Organic Compound
Chemical Structure
Thumb
SynonymsNot Available
Chemical FormulaC37H45NO5
Average Molecular Mass583.757 g/mol
Monoisotopic Mass583.330 g/mol
CAS Registry Number11076-67-8
IUPAC Name15,16,33,33-tetramethyl-24-methylidene-10-(prop-1-en-2-yl)-7,11,32-trioxa-18-azadecacyclo[25.4.2.0²,¹⁶.0⁵,¹⁵.0⁶,⁸.0⁶,¹².0¹⁷,³¹.0¹⁹,³⁰.0²²,²⁹.0²⁵,²⁸]tritriaconta-17(31),19(30),20,22(29)-tetraene-5,9-diol
Traditional Name15,16,33,33-tetramethyl-24-methylidene-10-(prop-1-en-2-yl)-7,11,32-trioxa-18-azadecacyclo[25.4.2.0²,¹⁶.0⁵,¹⁵.0⁶,⁸.0⁶,¹².0¹⁷,³¹.0¹⁹,³⁰.0²²,²⁹.0²⁵,²⁸]tritriaconta-17(31),19(30),20,22(29)-tetraene-5,9-diol
SMILESCC(=C)C1OC2CCC3(C)C4(C)C(CCC3(O)C22OC2C1O)C1OC(C)(C)C2CC3C2C2=C(CC3=C)C=CC3=C2C1=C4N3
InChI IdentifierInChI=1S/C37H45NO5/c1-16(2)29-28(39)32-37(43-32)23(41-29)11-12-34(6)35(7)20(10-13-36(34,37)40)30-27-26-22(38-31(27)35)9-8-18-14-17(3)19-15-21(25(19)24(18)26)33(4,5)42-30/h8-9,19-21,23,25,28-30,32,38-40H,1,3,10-15H2,2,4-7H3
InChI KeyCRPJNVUYZRFGAK-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
  • Tetralin
  • 3-alkylindole
  • Indole
  • Indole or derivatives
  • 1,4-dioxepane
  • Dioxepane
  • Monosaccharide
  • Oxane
  • Pyran
  • Benzenoid
  • Pyrrole
  • Cyclic alcohol
  • Tertiary alcohol
  • Heteroaromatic compound
  • Secondary alcohol
  • Azacycle
  • Oxacycle
  • Dialkyl ether
  • Oxirane
  • Ether
  • Alcohol
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen 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 Solubility0.00047 g/LALOGPS
logP5.06ALOGPS
logP4.76ChemAxon
logS-6.1ALOGPS
pKa (Strongest Acidic)12.8ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area87.24 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity162.79 m³·mol⁻¹ChemAxon
Polarizability67.61 ųChemAxon
Number of Rings10ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000090000-fcc8aba7eac84b5011ceSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-2000090000-b92d5e5d2de0d128cf70Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01b9-9050230000-43c28e9df6ff4b0c1b33Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-2000390000-e40e61a51db4a95d11a6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-3000490000-1bedac3b68d1ff7d3db5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014l-9020400000-94a0bacb6d9b5a965e79Spectrum
Toxicity Profile
Route of ExposureOral, dermal, inhalation, and parenteral (contaminated drugs). (8)
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. Penitrems are also know to increase the spontaneous release of the neurotransmitters glutamate and aspartate from cerebrocortical synaptosomes. In addition, they inhibits presynaptic high-conductance Ca+2 activated maxi-K+ channels in the smooth muscle. (3, 6, 7)
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesPenitrem B is a tremorgenic mycotoxin and neurotoxin produced by certain species of Aspergillus, Claviceps, and Penicillium. Penicillium crustosum in particular is a common foodborne fungus that causes spoilage in a wide variety of foods, including meat, cereals, nuts, cheese, eggs, fruit, and processed and refrigerated foods. (9, 4)
Minimum Risk LevelNot Available
Health EffectsTremorgenic mycotoxins affect central nervous system activity. They cause a neurological disease of horses and cattle known as "staggers syndrome". (3)
SymptomsPenitrems cause an tremorgenic syndrom consisting of acute tremor followed by chronic ataxia. Other symptoms include severe muscle fasciculations, vomiting, convulsions, tachycardia, and seizures, possibly leading to massive liver necrosis and death. Tremorgenic mycotoxins cause a neurological disease of cattle known as "staggers syndrome", which is characterized by muscle tremors and hyperexcitability. (2, 9, 4, 5)
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 IDHMDB0256239
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 ID73153936
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.