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CHEBI:3201 - bryotoxin A

ChEBI IDCHEBI:3201
ChEBI Namebryotoxin A
Stars
DefinitionA bufadienolide glycoside that is 3,5,11,14-tetrahydroxy-12,19-dioxobufa-20,22-dienolide attached to a 3-O-acetyl-4,6-dideoxy-β-D-arabino-hexopyranosyl residue at position 3 via a glycosidic linkage.
Last Modified6 February 2018
DownloadsMolfile
FormulaC32H42O12
Net Charge0
Average Mass618.676
Monoisotopic Mass618.26763
SMILES[H][C@@]12CC[C@]3(O)C[C@@H](O[C@@H]4O[C@H](C)C[C@@H](OC(C)=O)[C@@H]4O)CC[C@]3(C=O)[C@@]1([H])[C@H](O)C(=O)[C@@]1(C)[C@]2(O)CC[C@]1([H])c1ccc(=O)oc1
InChIInChI=1S/C32H42O12/c1-16-12-22(43-17(2)34)25(36)28(42-16)44-19-6-9-30(15-33)24-21(7-10-31(30,39)13-19)32(40)11-8-20(18-4-5-23(35)41-14-18)29(32,3)27(38)26(24)37/h4-5,14-16,19-22,24-26,28,36-37,39-40H,6-13H2,1-3H3/t16-,19+,20-,21-,22-,24-,25+,26+,28+,29+,30+,31+,32+/m1/s1
InChIKeyKWKQJZASURFCDP-ZPARAVGQSA-N
Species of MetaboliteComponentSourceComments
Bryophyllum tubiflorum (ncbitaxon:84209) - PubMed (3439945)
Roles Classification
Biological Role:
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
Application:
cardioprotective agent  Any protective agent that is able to prevent damage to the heart.
ChEBI Ontology
Outgoing Relation(s)
bryotoxin A (CHEBI:3201) has functional parent bufanolide (CHEBI:22934)
bryotoxin A (CHEBI:3201) has role plant metabolite (CHEBI:76924)
bryotoxin A (CHEBI:3201) is a 11α-hydroxy steroid (CHEBI:19129)
bryotoxin A (CHEBI:3201) is a 14β-hydroxy steroid (CHEBI:36862)
bryotoxin A (CHEBI:3201) is a 19-oxo steroid (CHEBI:38149)
bryotoxin A (CHEBI:3201) is a 5β-hydroxy steroid (CHEBI:38195)
bryotoxin A (CHEBI:3201) is a bufadienolide glycoside (CHEBI:83971)
bryotoxin A (CHEBI:3201) is a monosaccharide derivative (CHEBI:63367)
bryotoxin A (CHEBI:3201) is a secondary α-hydroxy ketone (CHEBI:2468)
bryotoxin A (CHEBI:3201) is a steroid aldehyde (CHEBI:131565)
IUPAC Name 
(3β,5β,11α)-3-[(3-O-acetyl-4,6-dideoxy-β-D-arabino-hexopyranosyl)oxy]-5,11,14-trihydroxy-12,19-dioxobufa-20,22-dienolide
Manual XrefsDatabases
C08853KEGG COMPOUND
C00003607KNApSAcK
Registry NumbersSources
Reaxys:7108097Reaxys
CAS:101329-50-4KEGG COMPOUND
CAS:101329-50-4ChemIDplus
Citations