Roquefortine (CHEM002631)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (23)XML
Record Information
Version1.0
Creation Date2009-12-17 22:23:05 UTC
Update Date2026-04-03 05:06:07 UTC
Accession NumberCHEM002631
Identification
Common NameRoquefortine
ClassSmall Molecule
DescriptionRoquefortine is found in milk and milk products. Roquefortine is a metabolite of Penicillium roquefortii, Penicillium commune, Penicillium cyclopium, Penicillium farinosum and many other Penicillium species Common constituent of blue cheese Roquefortine belongs to the family of Pyrroloindoles. These are compounds containing a pyrroloindole moiety, which is a tricyclic heterocycle which consists of a pyrrole ring fused to an indole.
Contaminant Sources
  • FooDB Chemicals
  • T3DB toxins
Contaminant Type
  • Amide
  • Amine
  • Ester
  • Food Toxin
  • Fungal Toxin
  • Industrial/Workplace Toxin
  • Lachrymator
  • Metabolite
  • Mycotoxin
  • Natural Compound
  • Organic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Isoroquefortine CMeSH
RoquefortinMeSH
Roquefortine CMeSH
Chemical FormulaC22H23N5O2
Average Molecular Mass389.450 g/mol
Monoisotopic Mass389.185 g/mol
CAS Registry Number58735-64-1
IUPAC Name(4Z)-6-hydroxy-4-(1H-imidazol-5-ylmethylidene)-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one
Traditional Name(4Z)-6-hydroxy-4-(3H-imidazol-4-ylmethylidene)-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one
SMILES[H]\C(C1=CN=CN1)=C1\N=C(O)C2CC3(C(NC4=CC=CC=C34)N2C1=O)C(C)(C)C=C
InChI IdentifierInChI=1S/C22H23N5O2/c1-4-21(2,3)22-10-17-18(28)25-16(9-13-11-23-12-24-13)19(29)27(17)20(22)26-15-8-6-5-7-14(15)22/h4-9,11-12,17,20,26H,1,10H2,2-3H3,(H,23,24)(H,25,28)/b16-9-
InChI KeySPWSUFUPTSJWNG-SXGWCWSVSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as pyrroloindoles. Pyrroloindoles are compounds containing a pyrroloindole moiety, which is a tricyclic heterocycle which consists of a pyrrole ring fused to an indole. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. Indole is a bicyclic compound consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassPyrroloindoles
Direct ParentPyrroloindoles
Alternative Parents
Substituents
  • Pyrroloindole
  • Alpha-amino acid or derivatives
  • Indole
  • Dihydroindole
  • Dioxopiperazine
  • 2,5-dioxopiperazine
  • Secondary aliphatic/aromatic amine
  • N-alkylpiperazine
  • 1,4-diazinane
  • Piperazine
  • Benzenoid
  • Heteroaromatic compound
  • Pyrrolidine
  • Pyrrole
  • Tertiary carboxylic acid amide
  • Azole
  • Imidazole
  • Secondary carboxylic acid amide
  • Amino acid or derivatives
  • Lactam
  • Carboxamide group
  • Secondary amine
  • Azacycle
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic oxide
  • Carbonyl group
  • Organonitrogen compound
  • Organooxygen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginEndogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder (12)
Experimental Properties
PropertyValue
Melting Point195 - 200°C
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.12 g/LALOGPS
logP2.48ALOGPS
logP1.24ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)3.32ChemAxon
pKa (Strongest Basic)7.57ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area93.61 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity112.02 m³·mol⁻¹ChemAxon
Polarizability41.5 ųChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0009000000-7866e3fc8e5fe3e2109eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-006x-0009000000-b7e693f9dd6fa39c3baeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-016r-9340000000-abf5ac70591c22dc2272Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0009000000-ebbc3981ceee0028fcefSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-3493000000-1463e19758f42a16a417Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6r-5960000000-35389d6eecd5bb26cfb1Spectrum
Toxicity Profile
Route of ExposureOral, dermal, inhalation, and parenteral (contaminated drugs). (9)
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. Roquefortine C also interacts with different forms of the cytochromes. (4, 6)
MetabolismNot Available
Toxicity ValuesLD50: 15-20 mg/kg (Intraperitoneal, Mouse) (5)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesRoquefortine C is a tremorgenic mycotoxin produced primarily by Penicillium roquefortii, but also by other Penicillium species. Penicillium roquefortii is used in the production of Roquefort and similar types of blue cheese, and has also been found growing in corn silage and mixed grains. Penicillium elaborated mycotoxins are well recognized as contaminants of many foods. These toxins, including mycophenolic acid (MPA), roquefortine (ROQ), penicillic acid (PA) and patulin (PAT) are reported to be toxic to several mammalian species. (2, 7)
Minimum Risk LevelNot Available
Health EffectsTremorgenic mycotoxins affect central nervous system activity. They cause a neurological disease of cattle known as "staggers syndrome". In severe cases roquefortine C can cause respiratory tract irritation, which can progress to ARDS/acute lung injury. Irritation or burns of the esophagus or gastrointestinal tract are also possible. Prostration, seizures, and death can also follow after absorption. (1, 5, 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, hyperexcitability, convulsions and ataxia. Roquefortine C may also cause irritation of the eyes, skin, and respiratory tract. (1, 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. (3)
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 LinkRoquefortine C
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID5358951
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available