Xanthomegnin (T3D3693)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationXML
Record Information
Version2.0
Creation Date2010-04-24 23:57:44 UTC
Update Date2014-12-24 20:26:22 UTC
Accession NumberT3D3693
Identification
Common NameXanthomegnin
ClassSmall Molecule
DescriptionXanthomegnin is a mutagenic mycotoxin isolated from Penicillium citreo-viride. It is known to cause nephropathy and death in farm animals exposed to food-borne Penicillium (and Aspergillus fungi). In humans and animals, oral intake of xanthomegnin leads to kidney and liver abnormalities, often first presenting as jaundice. Death may result. The compound has been shown to interfere with cellular respiratory processes and has given positive results in tests for genotoxic potential.
Compound Type
  • Ester
  • Ether
  • Food Toxin
  • Fungal Toxin
  • Mycotoxin
  • Natural Compound
  • Organic Compound
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
Synonym
Xanthomegnine
Chemical FormulaC30H22O12
Average Molecular Mass574.489 g/mol
Monoisotopic Mass574.111 g/mol
CAS Registry Number1685-91-2
IUPAC Name10-hydroxy-8-{10-hydroxy-7-methoxy-3-methyl-1,6,9-trioxo-1H,3H,4H,6H,9H-naphtho[2,3-c]pyran-8-yl}-7-methoxy-3-methyl-1H,3H,4H,6H,9H-naphtho[2,3-c]pyran-1,6,9-trione
Traditional Name10-hydroxy-8-{10-hydroxy-7-methoxy-3-methyl-1,6,9-trioxo-3H,4H-naphtho[2,3-c]pyran-8-yl}-7-methoxy-3-methyl-3H,4H-naphtho[2,3-c]pyran-1,6,9-trione
SMILESCOC1=C(C(=O)C2=C(O)C3=C(CC(C)OC3=O)C=C2C1=O)C1=C(OC)C(=O)C2=CC3=C(C(=O)OC(C)C3)C(O)=C2C1=O
InChI IdentifierInChI=1S/C30H22O12/c1-9-5-11-7-13-17(23(33)15(11)29(37)41-9)25(35)19(27(39-3)21(13)31)20-26(36)18-14(22(32)28(20)40-4)8-12-6-10(2)42-30(38)16(12)24(18)34/h7-10,33-34H,5-6H2,1-4H3
InChI KeyInChIKey=WICHONPZVIYWIJ-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as isochromanequinones. These are polycyclic compounds containing an isochromanequinone, which is structurally characterized by a quinone fused to an isochromane, and forming a naphtho[2,3-c]pyran-6,9-dione skeleton.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassIsochromanequinones
Sub ClassNot Available
Direct ParentIsochromanequinones
Alternative Parents
Substituents
  • Isochromanequinone
  • Naphthopyranone
  • Naphthopyran
  • Naphthoquinone
  • Benzopyran
  • Isochromane
  • Naphthalene
  • 2-benzopyran
  • Aryl ketone
  • Quinone
  • 1-hydroxy-4-unsubstituted benzenoid
  • Pyranone
  • Dicarboxylic acid or derivatives
  • Benzenoid
  • Pyran
  • Vinylogous ester
  • Vinylogous acid
  • Lactone
  • Ketone
  • Carboxylic acid ester
  • Organoheterocyclic compound
  • Oxacycle
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen 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
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.014 g/LALOGPS
logP3.24ALOGPS
logP4.13ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)8.88ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area179.8 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity146.98 m³·mol⁻¹ChemAxon
Polarizability57.06 ųChemAxon
Number of Rings6ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0000090000-be64286698fe2606f00f2016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0kdj-0012090000-92d56dbf1810e826186a2016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0bvu-3594470000-759739ae4893126721372016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00fr-0000090000-d1441ffccb35649c222d2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00dr-0050090000-bb0a59fcf9d80bd41dcf2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-059f-2090120000-74a5054fdc37713221aa2016-08-03View Spectrum
Toxicity Profile
Route of ExposureOral, dermal, inhalation, and parenteral (contaminated drugs). (1)
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesXanthomegnin is a mutagenic mycotoxin isolated from Penicillium citreo-viride.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
PubChem Compound ID15519
ChEMBL IDNot Available
ChemSpider ID14766
KEGG IDNot Available
UniProt IDNot Available
OMIM ID
ChEBI IDNot Available
BioCyc IDNot Available
CTD IDNot Available
Stitch IDNot Available
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
  1. Peraica M, Domijan AM: Contamination of food with mycotoxins and human health. Arh Hig Rada Toksikol. 2001 Mar;52(1):23-35. [11370295 ]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available