Fumitremorgin A (CHEM002710)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (22)XML
Record Information
Version1.0
Creation Date2010-05-10 14:30:53 UTC
Update Date2026-04-06 10:14:48 UTC
Accession NumberCHEM002710
Identification
Common NameFumitremorgin A
ClassSmall Molecule
DescriptionFumitremorgin A (FTA) is a potent neurotropic and tremorgenic mycotoxin isolated from Aspergillus fumigatus. Tremorgenic mycotoxins affect the central nervous system causing sustained tremors, convulsions, and death and have been implicated in a number of neurologic diseases of cattle collectively known as "staggers syndromes". FTA also severely affects the autonomic nervous system, likely through abnormal excitation of the central nervous system. (4, 5)
Contaminant Sources
  • T3DB toxins
Contaminant Type
  • Amide
  • Amine
  • Ether
  • Fungal Toxin
  • Mycotoxin
  • Natural Compound
  • Organic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
SynonymsNot Available
Chemical FormulaC32H41N3O7
Average Molecular Mass579.684 g/mol
Monoisotopic Mass579.294 g/mol
CAS Registry Number12626-18-5
IUPAC Name23-hydroxy-5-methoxy-12,12-dimethyl-24-[(3-methylbut-2-en-1-yl)oxy]-9-(2-methylprop-1-en-1-yl)-10,11-dioxa-8,15,21-triazahexacyclo[12.10.1.0²,⁷.0⁸,²⁵.0¹⁵,²³.0¹⁷,²¹]pentacosa-1(25),2(7),3,5-tetraene-16,22-dione
Traditional Name23-hydroxy-5-methoxy-12,12-dimethyl-24-[(3-methylbut-2-en-1-yl)oxy]-9-(2-methylprop-1-en-1-yl)-10,11-dioxa-8,15,21-triazahexacyclo[12.10.1.0²,⁷.0⁸,²⁵.0¹⁵,²³.0¹⁷,²¹]pentacosa-1(25),2(7),3,5-tetraene-16,22-dione
SMILESCOC1=CC2=C(C=C1)C1=C3C(CC(C)(C)OOC(C=C(C)C)N23)N2C(=O)C3CCCN3C(=O)C2(O)C1OCC=C(C)C
InChI IdentifierInChI=1S/C32H41N3O7/c1-18(2)12-14-40-28-26-21-11-10-20(39-7)16-23(21)34-25(15-19(3)4)41-42-31(5,6)17-24(27(26)34)35-29(36)22-9-8-13-33(22)30(37)32(28,35)38/h10-12,15-16,22,24-25,28,38H,8-9,13-14,17H2,1-7H3
InChI KeyACGHJVZDNQZJOV-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as beta carbolines. Beta carbolines are compounds containing a 9H-pyrido[3,4-b]indole moiety.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassPyridoindoles
Direct ParentBeta carbolines
Alternative Parents
Substituents
  • Beta-carboline
  • Alpha-amino acid or derivatives
  • 3-alkylindole
  • Indole
  • Anisole
  • Dioxopiperazine
  • 2,5-dioxopiperazine
  • Alkyl aryl ether
  • N-alkylpiperazine
  • 1,4-diazinane
  • Piperazine
  • Benzenoid
  • Heteroaromatic compound
  • Tertiary carboxylic acid amide
  • Pyrrolidine
  • Pyrrole
  • Carboxamide group
  • Lactam
  • Dialkyl peroxide
  • Azacycle
  • Ether
  • Oxacycle
  • Dialkyl ether
  • Carboxylic acid derivative
  • Alkanolamine
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organopnictogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organic oxygen 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 Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.08 g/LALOGPS
logP3.03ALOGPS
logP4.43ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)10.13ChemAxon
pKa (Strongest Basic)-4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area102.7 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity156.9 m³·mol⁻¹ChemAxon
Polarizability63.28 ųChemAxon
Number of Rings6ChemAxon
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, Positivesplash10-001i-2000190000-1724f0a3765dfb8a58fbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-030u-9000260000-2251cc421622f07e5a31Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0g4l-9210000000-3b266cf743b5334ee84dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-1000190000-a040bcbcad4e17925497Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0w2i-2002920000-2f06f5dc72dc54dd6c00Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9006000000-b9a098482bb580b8d698Spectrum
Toxicity Profile
Route of ExposureOral, dermal, inhalation, and parenteral (contaminated drugs). (7)
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. (2, 3, 4)
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesFumitremorgin A (FTA) is mycotoxin isolated from Aspergillus fumigatus. (5)
Minimum Risk LevelNot Available
Health EffectsTremorgenic mycotoxins affect central nervous system activity. They cause a neurological disease of cattle known as "staggers syndrome". (4)
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. Fumitremorgin A exposure has also been shown to cause bradycardia, arrhythmia, and hypertension. (2, 6)
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 ID14654100
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available