Marinobufagenin (T3D2536)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationXML
Record Information
Version2.0
Creation Date2009-07-03 22:19:15 UTC
Update Date2014-12-24 20:25:40 UTC
Accession NumberT3D2536
Identification
Common NameMarinobufagenin
ClassSmall Molecule
DescriptionMarinobufagin is a cardiotoxic bufanolide steroid secreted by certain toads (Bufo rubescens, Bufo marinus). It is a vasoconstrictor. (3)
Compound Type
  • Animal Toxin
  • Ester
  • Ether
  • Frog/Toad Toxin
  • Natural Compound
  • Organic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Synonym
Marcinobufagin
Marinobufagin
Marinobufogenin
MBG
Chemical FormulaC24H32O5
Average Molecular Mass400.508 g/mol
Monoisotopic Mass400.225 g/mol
CAS Registry Number470-42-8
IUPAC Name5-{14,16-dihydroxy-7,11-dimethyl-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-6-yl}-2H-pyran-2-one
Traditional Namemarinobufagenin
SMILESCC12CCC3C(CCC4(O)CC(O)CCC34C)C11OC1CC2C1=COC(=O)C=C1
InChI IdentifierInChI=1S/C24H32O5/c1-21-8-5-15(25)12-23(21,27)10-7-17-16(21)6-9-22(2)18(11-19-24(17,22)29-19)14-3-4-20(26)28-13-14/h3-4,13,15-19,25,27H,5-12H2,1-2H3
InChI KeyInChIKey=JMNQTHQLNRILMH-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as bufanolides and derivatives. These are steroid lactones containing a pyran-2-one moiety linked to the C17 atom of a cyclopenta[a]phenanthrene derivative.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSteroid lactones
Direct ParentBufanolides and derivatives
Alternative Parents
Substituents
  • Bufanolide-skeleton
  • Naphthopyran
  • Naphthalene
  • Pyranone
  • Pyran
  • Oxane
  • Cyclic alcohol
  • Heteroaromatic compound
  • Tertiary alcohol
  • Lactone
  • Secondary alcohol
  • Dialkyl ether
  • Oxirane
  • Ether
  • Oxacycle
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • 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 Solubility0.023 g/LALOGPS
logP2.38ALOGPS
logP2.13ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)14.22ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area79.29 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity107.82 m³·mol⁻¹ChemAxon
Polarizability43.69 ųChemAxon
Number of Rings6ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0096-0119000000-35cabbfbac7e48d8fa0c2021-09-23View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fsi-0009200000-dfc184fd6a8f05c3bd422016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0159-0139100000-8ee4029d111166eb152c2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uxr-7911000000-c8b3b0bf1e41f9afda392016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0009000000-0477e193a109d06d13202016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001j-0009000000-351f5d6450f51379f43a2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f79-2029000000-9b33929d9f316d3a2f342016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0009000000-96850b9ae8e75893b7652021-10-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0009000000-686146051517647da8842021-10-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-1009000000-6948b5b52ae08868b90e2021-10-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f89-0009400000-dbcf08246b488c2fd8c82021-10-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fsi-0019200000-020143afb5d3d96388802021-10-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08fr-4950000000-fe7916c1fa6a6c0e32432021-10-12View Spectrum
Toxicity Profile
Route of ExposureIngestion (4)
Mechanism of ToxicityMarinobufagin blocks the sodium/potassium pump in heart tissue. (2, 3)
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesMarinobufagin is a cardiotoxic bufanolide steroid secreted by certain toads (Bufo rubescens, Bufo marinus). (3)
Minimum Risk LevelNot Available
Health EffectsMarinobufagin is cardiotoxic and also causes vasoconstriction. (3)
SymptomsSymptoms include nausea, vomiting, anorexia, diarrhoea, abdominal pain, wild hallucinations, delirium, and severe headache. Depending on the severity the victim may later suffer irregular and slow pulse, tremors, various cerebral disturbances, especially of a visual nature, convulsions, and deadly disturbances of the heart such as heart block, brachycardia, or tachycardia. (3, 2)
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
PubChem Compound ID11969465
ChEMBL IDNot Available
ChemSpider IDNot Available
KEGG IDNot Available
UniProt IDNot Available
OMIM ID
ChEBI IDNot Available
BioCyc IDNot Available
CTD IDC093896
Stitch IDMarinobufagenin
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
  1. The Physical and Theoretical Chemistry Laboratory of Oxford University (2005). Material Safety Data Sheet (MSDS) for barium oxide. [Link]
  2. Wikipedia. Digitalis. Last Updated 29 June 2009. [Link]
  3. Wikipedia. Marinobufagenin. Last Updated 23 January 2009. [Link]
  4. Wikipedia. Bacterial toxin. Last Updated 27 February 2009. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available