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CHEBI:146151 - marinobufagenin

ChEBI IDCHEBI:146151
ChEBI Namemarinobufagenin
Stars
DefinitionA cardiotonic steroid secreted by the toad Bufo rubescens and other related species such as Bufo marinus. An endogenous Na/K-ATPase inhibitor, it is a vasoconstrictor with effects similar to digitalis.
Last Modified22 August 2023
SubmitterMarcus Ennis
DownloadsMolfile
FormulaC24H32O5
Net Charge0
Average Mass400.515
Monoisotopic Mass400.22497
SMILES[H][C@]12CC[C@]3(C)[C@@H](c4ccc(=O)oc4)C[C@H]4O[C@]43[C@]1([H])CC[C@]1(O)C[C@@H](O)CC[C@@]12C
InChIInChI=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/t15-,16-,17+,18+,19+,21+,22+,23-,24+/m0/s1
InChIKeyJMNQTHQLNRILMH-OBBGIPBRSA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Rhinella rubescens (ncbitaxon:752686) - PubMed (31879340)
Rhinella marina (ncbitaxon:8386) - PubMed (31879340)
Roles Classification
Biological Roles:
epitope  The biological role played by a material entity when bound by a receptor of the adaptive immune system. Specific site on an antigen to which an antibody binds.
EC 3.6.3.9 (Na(+)/K(+)-transporting ATPase) inhibitor  An EC 3.6.3.* (acid anhydride hydrolase catalysing transmembrane movement of substances) inhibitor that interferes with the action of Na+/K+-transporting ATPase (EC 3.6.3.9).
hormone  Originally referring to an endogenous compound that is formed in specialized organ or group of cells and carried to another organ or group of cells, in the same organism, upon which it has a specific regulatory function, the term is now commonly used to include non-endogenous, semi-synthetic and fully synthetic analogues of such compounds.
ChEBI Ontology
Outgoing Relation(s)
marinobufagenin (CHEBI:146151) has functional parent (5β)-bufadienolide (CHEBI:83977)
marinobufagenin (CHEBI:146151) has role EC 3.6.3.9 (Na+/K+-transporting ATPase) inhibitor (CHEBI:63510)
marinobufagenin (CHEBI:146151) has role epitope (CHEBI:53000)
marinobufagenin (CHEBI:146151) is a epoxy steroid (CHEBI:145217)
marinobufagenin (CHEBI:146151) is a steroid hormone (CHEBI:26764)
IUPAC Name 
3β,5-dihydroxy-5β,15β-14,15-epoxybufa-20,22-dienolide
Synonyms  Source
(3beta,5beta,14alpha,15beta)-3,5-dihydroxy-14,15-epoxybufa-20,22-dienolidePDBeChem
MarinobufaginChemIDplus
MBGChEBI
Manual XrefsDatabases
P4SPDBeChem
MarinobufageninWikipedia
Registry NumbersSources
CAS:470-42-8ChemIDplus
Citations