Fumitremorgin B (CHEM002711)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (23)XML
Record Information
Version1.0
Creation Date2010-05-10 14:51:52 UTC
Update Date2026-04-06 13:35:08 UTC
Accession NumberCHEM002711
Identification
Common NameFumitremorgin B
ClassSmall Molecule
DescriptionFumitremorgin B is a mycotoxin produced by Aspergillus fumigatus, Aspergillus caespitosus, Penicillium lanosum and Penicillium piscarium. Fumitremorgin B is isolated from A. fumigatus infected rice and miso Fumitremorgin b belongs to the family of Indoles. These are compounds containing an indole moiety, which consists of pyrrole ring fused to benzene to form 2,3-benzopyrrole.
Contaminant Sources
  • FooDB Chemicals
  • T3DB toxins
Contaminant Type
  • Amide
  • Amine
  • Ether
  • Food Toxin
  • Fungal Toxin
  • Metabolite
  • Mycotoxin
  • Natural Compound
  • Organic Compound
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
LanosulinHMDB
Chemical FormulaC27H33N3O5
Average Molecular Mass479.568 g/mol
Monoisotopic Mass479.242 g/mol
CAS Registry Number12626-17-4
IUPAC Name1,2-dihydroxy-7-methoxy-10-(3-methylbut-2-en-1-yl)-12-(2-methylprop-1-en-1-yl)-10,13,19-triazapentacyclo[11.7.0.0³,¹¹.0⁴,⁹.0¹⁵,¹⁹]icosa-3(11),4(9),5,7-tetraene-14,20-dione
Traditional Name1,2-dihydroxy-7-methoxy-10-(3-methylbut-2-en-1-yl)-12-(2-methylprop-1-en-1-yl)-10,13,19-triazapentacyclo[11.7.0.0³,¹¹.0⁴,⁹.0¹⁵,¹⁹]icosa-3(11),4(9),5,7-tetraene-14,20-dione
SMILESCOC1=CC2=C(C=C1)C1=C(C(C=C(C)C)N3C(=O)C4CCCN4C(=O)C3(O)C1O)N2CC=C(C)C
InChI IdentifierInChI=1S/C27H33N3O5/c1-15(2)10-12-28-20-14-17(35-5)8-9-18(20)22-23(28)21(13-16(3)4)30-25(32)19-7-6-11-29(19)26(33)27(30,34)24(22)31/h8-10,13-14,19,21,24,31,34H,6-7,11-12H2,1-5H3
InChI KeyWEIYXEFMCIRZHC-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
  • N-alkylindole
  • 3-alkylindole
  • Indole
  • Anisole
  • Dioxopiperazine
  • 2,5-dioxopiperazine
  • Alkyl aryl ether
  • N-alkylpiperazine
  • 1,4-diazinane
  • Piperazine
  • Substituted pyrrole
  • Benzenoid
  • Pyrrolidine
  • Pyrrole
  • Tertiary carboxylic acid amide
  • Heteroaromatic compound
  • Secondary alcohol
  • Lactam
  • Carboxamide group
  • Alkanolamine
  • Azacycle
  • Ether
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organopnictogen 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
  • Cytoplasm
  • Extracellular
  • 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 Point211 - 212°C
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.3 g/LALOGPS
logP2.16ALOGPS
logP2.74ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)10.13ChemAxon
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area95.24 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity133.33 m³·mol⁻¹ChemAxon
Polarizability52.99 ųChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0w31-5139500000-39a59034a27f4e4c8d48Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0apj-9014274000-4c5f595931915314386bSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS ("Fumitremorgin B,2TMS,#1" TMS) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-1000900000-e19d0bfd2e517960f36bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00xu-9070600000-3254bfcb3d70c62863bfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gi3-9000000000-62f3e147eb01d7a8a5aaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-1000900000-883706de0236f02775a9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ufu-4009300000-35dfd4c375bfb9276168Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-4092000000-31812038db5393ad0414Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000900000-28fdcd8d6f2aef27b884Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0000900000-16bc6def02ffcbcae235Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0296-9121700000-40edf0496ef962b765a9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000900000-32d1eaece5685ec03760Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0004900000-f00354422eba0d8cbf29Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-1391300000-4484b6e16e6127fff8f4Spectrum
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 B is a mycotoxin that has been found in the fungus 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". Fumitremorgin B is also genotoxic and causes DNA damage. (4, 6)
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. (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. (1)
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0030203
FooDB IDFDB002021
Phenol Explorer IDNot Available
KNApSAcK IDC00011297
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID94836
ChEBI ID64531
PubChem Compound ID105113
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.