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CHEBI:517248 - bufalin

ChEBI IDCHEBI:517248
ChEBI Namebufalin
Stars
DefinitionA 14β-hydroxy steroid that is bufan-20,22-dienolide having hydroxy substituents at the 5β- and 14β-positions. It has been isolated from the skin of the toad Bufo bufo.
Last Modified30 November 2015
DownloadsMolfile
FormulaC24H34O4
Net Charge0
Average Mass386.532
Monoisotopic Mass386.24571
SMILES[H][C@]12CC[C@]3([H])[C@]([H])(CC[C@@]4(C)[C@]3(O)CC[C@]4([H])c3ccc(=O)oc3)[C@@]1(C)CC[C@H](O)C2
InChIInChI=1S/C24H34O4/c1-22-10-7-17(25)13-16(22)4-5-20-19(22)8-11-23(2)18(9-12-24(20,23)27)15-3-6-21(26)28-14-15/h3,6,14,16-20,25,27H,4-5,7-13H2,1-2H3/t16-,17+,18-,19+,20-,22+,23-,24+/m1/s1
InChIKeyQEEBRPGZBVVINN-BMPKRDENSA-N
Species of MetaboliteComponentSourceComments
Bufo bufo (ncbitaxon:8384) - PubMed (21185919)
Roles Classification
Biological Role:
animal metabolite  Any eukaryotic metabolite produced during a metabolic reaction in animals that include diverse creatures from sponges, insects to mammals.
Applications:
cardiotonic drug  A drug that has a strengthening effect on the heart or that can increase cardiac output.
anti-inflammatory agent  Any compound that has anti-inflammatory effects.
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
bufalin (CHEBI:517248) has functional parent bufanolide (CHEBI:22934)
bufalin (CHEBI:517248) has role animal metabolite (CHEBI:75767)
bufalin (CHEBI:517248) has role anti-inflammatory agent (CHEBI:67079)
bufalin (CHEBI:517248) has role antineoplastic agent (CHEBI:35610)
bufalin (CHEBI:517248) has role cardiotonic drug (CHEBI:38147)
bufalin (CHEBI:517248) is a 14β-hydroxy steroid (CHEBI:36862)
bufalin (CHEBI:517248) is a 3β-hydroxy steroid (CHEBI:36836)
IUPAC Name 
(3β,5β)-3,14-dihydroxybufa-20,22-dienolide
Synonyms  Source
3-beta,14-Dihydroxy-5-beta-bufa-20,22-dienolideChemIDplus
3,14-Dihydroxy-bufa-20,22-dienolideChemIDplus
3β,14β-dihydroxy-5β-bufa-20,22-dienolideLIPID MAPS
Manual XrefsDatabases
LMST01130001LIPID MAPS
C16922KEGG COMPOUND
Registry NumbersSources
Reaxys:96550Reaxys
CAS:465-21-4KEGG COMPOUND
CAS:465-21-4ChemIDplus
Citations