Rubratoxin B (CHEM002699)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (20)XML
Record Information
Version1.0
Creation Date2010-05-04 21:13:54 UTC
Update Date2026-04-04 23:56:36 UTC
Accession NumberCHEM002699
Identification
Common NameRubratoxin B
ClassSmall Molecule
DescriptionRubratoxin B is a mycotoxin produced by fungi such as Penicillum rubrum and Penicillum purpurogenum, which are common soil fungi that sometimes contaminate animal feeds. Rubratoxin B has been shown to be hepatotoxic, nephrotoxic, and splenotoxic. (2)
Contaminant Sources
  • T3DB toxins
Contaminant Type
  • Ester
  • Ether
  • Fungal Toxin
  • Mycotoxin
  • Natural Compound
  • Organic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
RubratoxinMeSH
RubratoxinsMeSH
Chemical FormulaC26H30O11
Average Molecular Mass518.510 g/mol
Monoisotopic Mass518.179 g/mol
CAS Registry Number21794-01-4
IUPAC Name2-hydroxy-10-[hydroxy(6-oxo-3,6-dihydro-2H-pyran-2-yl)methyl]-3-(1-hydroxyheptyl)-6,14-dioxatricyclo[10.3.0.0⁴,⁸]pentadeca-1(12),4(8)-diene-5,7,13,15-tetrone
Traditional Namerubratoxin B
SMILESCCCCCCC(O)C1C(O)C2=C(CC(CC3=C1C(=O)OC3=O)C(O)C1CC=CC(=O)O1)C(=O)OC2=O
InChI IdentifierInChI=1S/C26H30O11/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/h6,9,12,15-16,20-22,27,29-30H,2-5,7-8,10-11H2,1H3
InChI KeyZJTBTDVZNGBSNG-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as pentacarboxylic acids and derivatives. These are carboxylic acids containing exactly five carboxyl groups.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassPentacarboxylic acids and derivatives
Direct ParentPentacarboxylic acids and derivatives
Alternative Parents
Substituents
  • Pentacarboxylic 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
  • Lactone
  • Secondary alcohol
  • Organoheterocyclic compound
  • Oxacycle
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxide
  • Carbonyl group
  • Organooxygen compound
  • Organic oxygen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic 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
Predicted Properties
PropertyValueSource
Water Solubility0.14 g/LALOGPS
logP1.52ALOGPS
logP2.38ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)3.08ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area173.73 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity126.17 m³·mol⁻¹ChemAxon
Polarizability52.08 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, Positivesplash10-0ue9-0000960000-5a611ed1d9835cb0c661Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fh9-2002910000-64b43b8694a362ca75fcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fxy-8007900000-3430846a09e3a75b7b34Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00xr-0000930000-0be53125a6e059a12ff2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00fs-1103900000-7ba191ed9f227c47b5deSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-7009600000-549934362a01c46622d9Spectrum
Toxicity Profile
Route of ExposureOral, dermal, inhalation, and parenteral (contaminated drugs). (6)
Mechanism of ToxicityRubratoxin B is cytotoxic, hinders cell proliferation, and induces apoptosis. It also inhibits the activity of matrix metalloproteinase-2 and -9. Rubratoxin B causes disaggregation of the polyribosome complex, likely by inhibiting an enzyme associated with the site of polyribosome binding to the membrane. It has also been shown to bind to some hepatic microsomes and inhibit Na+/K+-transporting ATPases. Rubratoxin B can inhibit 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. Mycotoxins are often able to enter the liver and kidney by human organic anion transporters (hOATs) and human organic cation transporters (hOCTs). They can also inhibit uptake of anions and cations by these transporters, interefering with the secretion of endogenous metabolites, drugs, and xenobiotics including themselves. This results in increased cellular accumulation of toxic compounds causing nephro- and hepatotoxicity. (2, 3, 4, 5)
MetabolismNot Available
Toxicity ValuesLD50: 0.22-0.43 mg/kg (Intraperitoneal, Mouse) (1)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesRubratoxin B is a mycotoxin produced by fungi such as Penicillum rubrum and Penicillum purpurogenum, which are common soil fungi that sometimes contaminate animal feeds. (2)
Minimum Risk LevelNot Available
Health EffectsRubratoxin B is hepatotoxic, nephrotoxic, and splenotoxic, causing congestive, hemorrhagic and degenerative lesions. (2, 3)
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0257359
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkRubratoxin B
Chemspider ID28591
ChEBI IDNot Available
PubChem Compound ID30816
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available