Aflatrem (CHEM002695)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (26)XML
Record Information
Version1.0
Creation Date2010-05-03 19:08:59 UTC
Update Date2026-04-06 14:00:54 UTC
Accession NumberCHEM002695
Identification
Common NameAflatrem
ClassSmall Molecule
DescriptionAflatrem is a tremorgenic mycotoxin that has been found in the fungus Aspergillus flavus. 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 FormulaC32H39NO4
Average Molecular Mass501.656 g/mol
Monoisotopic Mass501.288 g/mol
CAS Registry Number70553-75-2
IUPAC Name19-hydroxy-4,5,24,24-tetramethyl-12-(2-methylbut-3-en-2-yl)-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-12-(2-methylbut-3-en-2-yl)-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
SMILESCC(C)(C=C)C1=C2C3=C(NC2=CC=C1)C1(C)C(C3)CCC2(O)C3=CC(=O)C4OC3(CCC12C)OC4(C)C
InChI IdentifierInChI=1S/C32H39NO4/c1-8-27(2,3)20-10-9-11-21-24(20)19-16-18-12-13-31(35)23-17-22(34)26-28(4,5)37-32(23,36-26)15-14-29(31,6)30(18,7)25(19)33-21/h8-11,17-18,26,33,35H,1,12-16H2,2-7H3
InChI KeyYVDJBQQJIDPRKP-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 Solubility5.9e-05 g/LALOGPS
logP6.06ALOGPS
logP6.05ChemAxon
logS-6.9ALOGPS
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 Count2ChemAxon
Refractivity144.6 m³·mol⁻¹ChemAxon
Polarizability57.18 ųChemAxon
Number of Rings7ChemAxon
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, Positivesplash10-0f89-0000950000-93f66af1b4a515fabf97Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fsi-0101920000-9b63d32d60c80d45be2fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gbi-3196400000-48470ae2a83b4592f17dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000290000-01d062b347bad0871da5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ue9-0000890000-f6ed91eaae2ecca3c00aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05uu-1203900000-3805851f3bb678cfb4dbSpectrum
Toxicity Profile
Route of ExposureOral, dermal, inhalation, and parenteral (contaminated drugs). (6)
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, aflatrem inhibits presynaptic high-conductance Ca+2 activated maxi-K+ channels in the smooth muscle. (2, 3, 4, 5)
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesAflatrem is a tremorgenic mycotoxin that has been found in the fungus Aspergillus flavus. (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 and hyperexcitability. (2)
TreatmentTo control severe tremorscaused 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 ID107718
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available