Janthitrem G (CHEM002733)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (47)XML
Record Information
Version1.0
Creation Date2010-05-20 15:21:17 UTC
Update Date2026-08-22 12:15:30 UTC
Accession NumberCHEM002733
Identification
Common NameJanthitrem G
ClassSmall Molecule
DescriptionJanthitrem G is an exogenous solid with the chemical formula C39H51NO6. Janthitrem G belongs to the naphthopyrans, a class of organoheterocyclic compounds within the organic compounds. With an average molecular weight of 629.83 g/mol, Janthitrem G is a heavy molecule. This tremorgenic mycotoxin is produced by Penicillium janthinellum. It has 22 recorded protein targets, including mitochondrial 4-aminobutyrate aminotransferase (ABAT) and Gamma-aminobutyric acid receptor subunits alpha-1 (GABRA1), alpha-2 (GABRA2), and alpha-3 (GABRA3), among 18 other proteins. Tremorgenic mycotoxins 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 mechanism would initially increase neurotransmitter levels, potentiating the GABA-induced chloride current, and subsequently lead to decreased levels of neurotransmitter in the synapse.
Contaminant Sources
  • FooDB Chemicals
  • T3DB toxins
Contaminant Type
  • Ester
  • Ether
  • Food Toxin
  • Fungal Toxin
  • Metabolite
  • Mycotoxin
  • Natural Compound
  • Organic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
9-L-Serinepolypeptin aHMDB
9-L-Serinepolypeptin a, 9ciHMDB
Antibiotic NLF-IIHMDB
NLF-IIHMDB
Permycin aHMDB
Polypeptin a, 9-L-serineHMDB
12-Hydroxy-8-(2-hydroxypropan-2-yl)-2,3,23,23,25,25-hexamethyl-7,24-dioxa-31-azaoctacyclo[15.14.0.0²,¹⁵.0³,¹².0⁶,¹¹.0¹⁸,³⁰.0²⁰,²⁸.0²²,²⁷]hentriaconta-1(17),10,18(30),19,26,28-hexaen-9-yl acetic acidHMDB
Chemical FormulaC39H51NO6
Average Molecular Mass629.825 g/mol
Monoisotopic Mass629.372 g/mol
CAS Registry Number90986-51-9
IUPAC Name[12-hydroxy-8-(2-hydroxypropan-2-yl)-2,3,23,23,25,25-hexamethyl-7,24-dioxa-31-azaoctacyclo[15.14.0.02,15.03,12.06,11.018,30.020,28.022,27]hentriaconta-1(17),10,18(30),19,26,28-hexaen-9-yl] acetate
Traditional Name12-hydroxy-8-(2-hydroxypropan-2-yl)-2,3,23,23,25,25-hexamethyl-7,24-dioxa-31-azaoctacyclo[15.14.0.0²,¹⁵.0³,¹².0⁶,¹¹.0¹⁸,³⁰.0²⁰,²⁸.0²²,²⁷]hentriaconta-1(17),10,18(30),19,26,28-hexaen-9-yl acetate
SMILESCC(=O)OC1C=C2C(CCC3(C)C4(C)C(CC5=C4NC4=C5C=C5CC6C(=CC(C)(C)OC6(C)C)C5=C4)CCC23O)OC1C(C)(C)O
InChI IdentifierInChI=1S/C39H51NO6/c1-20(41)44-31-18-28-30(45-33(31)35(4,5)42)11-12-37(8)38(9)22(10-13-39(28,37)43)16-25-24-14-21-15-27-26(19-34(2,3)46-36(27,6)7)23(21)17-29(24)40-32(25)38/h14,17-19,22,27,30-31,33,40,42-43H,10-13,15-16H2,1-9H3
InChI KeyPGYSJEQVCATFBQ-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
  • Indane
  • Indole
  • Indole or derivatives
  • Benzenoid
  • Pyran
  • Cyclic alcohol
  • Heteroaromatic compound
  • Tertiary alcohol
  • Pyrrole
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Dialkyl ether
  • Ether
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Azacycle
  • Organic oxide
  • Organopnictogen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Alcohol
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Extracellular
  • 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 Solubility0.00025 g/LALOGPS
logP6.16ALOGPS
logP5.12ChemAxon
logS-6.4ALOGPS
pKa (Strongest Acidic)13.61ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area101.01 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity178.79 m³·mol⁻¹ChemAxon
Polarizability74.83 ųChemAxon
Number of Rings8ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0c0u-6001396000-bcf00a7be951a3b83b97Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableSpectrum
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_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 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_1) - 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_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS ("Janthitrem G,1TMS,#1" TMS) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03e9-1000198000-9cc3c3fc759d71bd01f5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0000090000-5e79491898c50ee1f8c4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00xr-4002950000-df54d69583fda30f6b0dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-4000069000-768eacf04f771ce6d228Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-07y0-5000194000-dc72c776c640d64a3ae7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9100430000-2e7232a75660a0526512Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-05p9-2000093000-a7179a1ecad58edbd2b7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9000000000-c01bbbf5bed889264ddbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6u-9100030000-e223a97f62dc5c33ddb7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000049000-8fb9d34d8d88788e364dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0002197000-dd28a8307b7420127a90Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0api-9045581000-ea143d166d2d9fdbc23eSpectrum
Toxicity Profile
Route of ExposureOral, dermal, inhalation, and parenteral (contaminated drugs). (4)
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)
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesJanthitrems are tremorgenic mycotoxins that have been found in the fungus Penicillium janthinellum. They may be found in contaminated cereal crops such as oats, barley, millet, corn and rice. (2, 3)
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, hyperexcitability, convulsions and ataxia. (2)
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 IDHMDB0030531
FooDB IDFDB002404
Phenol Explorer IDNot Available
KNApSAcK IDC00018214
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID8569675
ChEBI IDNot Available
PubChem Compound ID10394234
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.