Rubratoxin A (CHEM002700)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (37)XML
Record Information
Version1.0
Creation Date2010-05-05 14:57:46 UTC
Update Date2026-04-06 13:51:16 UTC
Accession NumberCHEM002700
Identification
Common NameRubratoxin A
ClassSmall Molecule
DescriptionRubratoxin A is an exogenous compound that exists as a solid at room temperature. It has the chemical formula C26H32O11. Rubratoxin A belongs to the tetracarboxylic acids and derivatives, a subclass of carboxylic acids and derivatives within the organic compounds. With an average molecular weight of 520.53 g/mol, Rubratoxin A is a heavy molecule. The compound acts as a potent inhibitor of protein phosphatase 2A, specifically targeting the serine/threonine-protein phosphatase 2A catalytic subunit alpha isoform (PPP2CA), the serine/threonine-protein phosphatase 2A catalytic subunit beta isoform (PPP2CB), and the serine/threonine-protein phosphatase 2A 65 kDa regulatory subunit A alpha isoform (PPP2R1A). This inhibition exerts antitumor and antimetastatic effects. These antimetastatic effects may be attributed to the phosphorylation of CREB and subsequent activation of natural killer cells via the stimulation of interleukin-2 release from T cells, as well as the phosphorylation of focal adhesion kinase and paxillin, which interferes with cell adhesion. Additionally, Rubratoxin A inhibits Na+/K+-transporting ATPases in the brain. The recorded protein targets for this action include the sodium/potassium-transporting ATPase subunit gamma (FXYD2), sodium/potassium-transporting ATPase subunit alpha-1 (ATP1A1), sodium/potassium-transporting ATPase subunit alpha-2 (ATP1A2), sodium/potassium-transporting ATPase subunit alpha-3 (ATP1A3), and four other proteins.
Contaminant Sources
  • T3DB toxins
Contaminant Type
  • Ester
  • Fungal Toxin
  • Mycotoxin
  • Natural Compound
  • Organic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
SynonymsNot Available
Chemical FormulaC26H32O11
Average Molecular Mass520.526 g/mol
Monoisotopic Mass520.194 g/mol
CAS Registry Number22467-31-8
IUPAC NameNot Available
Traditional Namerubratoxin A
SMILESCCCCCCC(O)C1C(O)C2=C(CC(CC3=C1C(=O)OC3O)C(O)C1CC=CC(=O)O1)C(=O)OC2=O
InChI IdentifierInChI=1S/C26H32O11/c1-2-3-4-5-7-15(27)20-18-13(23(31)36-25(18)33)10-12(21(29)16-8-6-9-17(28)35-16)11-14-19(22(20)30)26(34)37-24(14)32/h6,9,12,15-16,20-23,27,29-31H,2-5,7-8,10-11H2,1H3
InChI KeyXOEFANNJIKAWGX-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as tetracarboxylic acids and derivatives. These are carboxylic acids containing exactly four carboxyl groups.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassTetracarboxylic acids and derivatives
Direct ParentTetracarboxylic acids and derivatives
Alternative Parents
Substituents
  • Tetracarboxylic acid or derivatives
  • Fatty alcohol
  • Dihydropyranone
  • 2-furanone
  • Fatty acyl
  • Pyran
  • Carboxylic acid anhydride
  • Dihydrofuran
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Carboxylic acid ester
  • Hemiacetal
  • Lactone
  • Secondary alcohol
  • Organoheterocyclic compound
  • Oxacycle
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
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 Solubility0.51 g/LALOGPS
logP1.03ALOGPS
logP1.84ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)5.82ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area176.89 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity126.97 m³·mol⁻¹ChemAxon
Polarizability52.8 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uki-0000950000-7dab2fb6e40a70c46ab9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fbi-2002920000-eb130d29e6a6b2f8c4bcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00or-8009700000-6d3e8e7485ab269744ddSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00or-0000950000-15f346a9acb50bd3c156Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-1104920000-2776f3274c8bf8769f48Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06rf-9007700000-03fc72dc99c97d1eba36Spectrum
Toxicity Profile
Route of ExposureOral, dermal, inhalation, and parenteral (contaminated drugs). (5)
Mechanism of ToxicityRubratoxin A is a potent inhibitor of protein phosphatase 2A, exerting antitumor and antimetastatic effects. Inhibition may cause the phosphorylation of CREB and subsequent activation of natural killer cells via the stimulation of interleukin-2 release from T cells, contributing to antimetastatic effects. Focal adhesion kinase phosphorylation and paxillin phosphorylation that interfere with cell adhesion could be another antimetastatic effect. Rubratoxin A has also been shown to inhibit Na+/K+-transporting ATPases. (3, 4)
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesRubratoxin A is a mycotoxin produced by fungi such as Penicillum rubrum and Penicillum purpurogenum, which are common soil fungi that sometimes contaminate animal feeds. (1, 4)
Minimum Risk LevelNot Available
Health EffectsRubratoxins are hepatotoxic, nephrotoxic, and splenotoxic, causing congestive, hemorrhagic and degenerative lesions. (1, 2)
SymptomsNot Available
TreatmentNot Available
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 ID31181
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available