CHEBI:146151 - marinobufagenin

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ChEBI Name marinobufagenin
ChEBI ID CHEBI:146151
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C24H32O5
Net Charge 0
Average Mass 400.515
Monoisotopic Mass 400.22497
InChI 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/t15-,16-,17+,18+,19+,21+,22+,23-,24+/m0/s1
InChIKey JMNQTHQLNRILMH-OBBGIPBRSA-N
SMILES [C@]12(CC[C@@H](C[C@]2(CC[C@]3([C@]45[C@](CC[C@]13[H])([C@H](C[C@H]4O5)C6=COC(C=C6)=O)C)[H])O)O)C
Metabolite of Species Details
Rhinella rubescens (NCBI:txid752686) See: PubMed
Rhinella marina (NCBI:txid8386) See: PubMed
Roles Classification
Biological Role(s): 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).
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.
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.
(via steroid hormone )
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ChEBI Ontology
Outgoing 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 Sources
(3beta,5beta,14alpha,15beta)-3,5-dihydroxy-14,15-epoxybufa-20,22-dienolide PDBeChem
Marinobufagin ChemIDplus
MBG ChEBI
Manual Xrefs Databases
Marinobufagenin Wikipedia
P4S PDBeChem
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Registry Number Type Source
470-42-8 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
11877366 PubMed citation Europe PMC
15804527 PubMed citation Europe PMC
29853035 PubMed citation Europe PMC
29993282 PubMed citation Europe PMC
30382957 PubMed citation Europe PMC
30817774 PubMed citation Europe PMC
31236418 PubMed citation Europe PMC
31879340 PubMed citation Europe PMC
Last Modified
22 August 2023