ContaminantDB: Marinobufagenin

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2009-07-03 22:19:15 UTC

Update Date

2016-11-09 01:08:40 UTC

Accession Number

CHEM002077

Identification

Common Name

Marinobufagenin

Class

Small Molecule

Description

Marinobufagin is a cardiotoxic bufanolide steroid secreted by certain toads (Bufo rubescens, Bufo marinus). It is a vasoconstrictor. (3)

Contaminant Sources

T3DB toxins

Contaminant Type

Animal Toxin
Ester
Ether
Frog/Toad Toxin
Natural Compound
Organic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Marinobufogenin	MeSH

Chemical Formula

C₂₄H₃₂O₅

Average Molecular Mass

400.508 g/mol

Monoisotopic Mass

400.225 g/mol

CAS Registry Number

470-42-8

IUPAC Name

5-{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 Name

marinobufagenin

SMILES

CC12CCC3C(CCC4(O)CC(O)CCC34C)C11OC1CC2C1=COC(=O)C=C1

InChI Identifier

InChI=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 Key

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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroid lactones

Direct Parent

Bufanolides 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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.023 g/L	ALOGPS
logP	2.38	ALOGPS
logP	2.13	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	14.22	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	79.29 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	107.82 m³·mol⁻¹	ChemAxon
Polarizability	43.69 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0096-0119000000-35cabbfbac7e48d8fa0c	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0fsi-0009200000-dfc184fd6a8f05c3bd42	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0159-0139100000-8ee4029d111166eb152c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0uxr-7911000000-c8b3b0bf1e41f9afda39	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0009000000-0477e193a109d06d1320	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001j-0009000000-351f5d6450f51379f43a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0f79-2029000000-9b33929d9f316d3a2f34	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0009000000-96850b9ae8e75893b765	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-0009000000-686146051517647da884	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0002-1009000000-6948b5b52ae08868b90e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0f89-0009400000-dbcf08246b488c2fd8c8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0fsi-0019200000-020143afb5d3d9638880	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-08fr-4950000000-fe7916c1fa6a6c0e3243	Spectrum

Toxicity Profile

Route of Exposure

Ingestion (4)

Mechanism of Toxicity

Marinobufagin blocks the sodium/potassium pump in heart tissue. (2, 3)

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Marinobufagin is a cardiotoxic bufanolide steroid secreted by certain toads (Bufo rubescens, Bufo marinus). (3)

Minimum Risk Level

Not Available

Health Effects

Marinobufagin is cardiotoxic and also causes vasoconstriction. (3)

Symptoms

Symptoms 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)

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

Not Available

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Marinobufagenin

Chemspider ID

Not Available

ChEBI ID

Not Available

PubChem Compound ID

615793

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

Marinobufagenin (CHEM002077)

Structure for CHEM002077: Marinobufagenin