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> Main
CHEBI:517248 - bufalin
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ChEBI Ontology
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ChEBI Name
bufalin
ChEBI ID
CHEBI:517248
Definition
A 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
.
Stars
This entity has been manually annotated by the ChEBI Team.
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Formula
C24H34O4
Net Charge
0
Average Mass
386.52440
Monoisotopic Mass
386.24571
InChI
InChI=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
InChIKey
QEEBRPGZBVVINN-BMPKRDENSA-N
SMILES
[H][C@]12CC[C@]3([H])[C@]([H])(CC[C@]4(C)[C@]([H])(CC[C@]34O)c3ccc(=O)oc3)[C@@]1(C)CC[C@H](O)C2
Metabolite of Species
Details
Bufo bufo
(NCBI:txid8384)
See:
PubMed
Roles Classification
Biological Role
(s):
animal metabolite
Any eukaryotic metabolite produced during a metabolic reaction in animals that include diverse creatures from sponges, insects to mammals.
Application
(s):
antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing
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
Sources
3,14-Dihydroxy-bufa-20,22-dienolide
ChemIDplus
3-beta,14-Dihydroxy-5-beta-bufa-20,22-dienolide
ChemIDplus
3β,14β-dihydroxy-5β-bufa-20,22-dienolide
LIPID MAPS
Manual Xrefs
Databases
C16922
KEGG COMPOUND
LMST01130001
LIPID MAPS
View more database links
Registry Numbers
Types
Sources
465-21-4
CAS Registry Number
ChemIDplus
96550
Beilstein Registry Number
Beilstein
96550
Reaxys Registry Number
Reaxys
Citations
Types
Sources
10438974
PubMed citation
Europe PMC
21185919
PubMed citation
Europe PMC
23949904
PubMed citation
Europe PMC
24484199
PubMed citation
Europe PMC
24515724
PubMed citation
Europe PMC
24719521
PubMed citation
Europe PMC
26111756
PubMed citation
Europe PMC
26133118
PubMed citation
Europe PMC
26381511
PubMed citation
Europe PMC
26446205
PubMed citation
Europe PMC
8282340
PubMed citation
Europe PMC
Last Modified
30 November 2015