CHEBI:27729 - digitonin

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ChEBI Name digitonin
ChEBI ID CHEBI:27729
Definition A spirostanyl glycoside that is digitogenin in which the 3-hydroxy group is substituted by a β-D-glucopyranosyl-(1→3)-β-D-galactopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→3)]-β-D-glucopyranosyl-(1→4)-β-D-galactopyranosyl group. It is a steroidal saponin isolated from the foxglove plant, Digitalis purpurea. It is used extensively as a mild non-ionic detergent for extracting proteins from membranes for structure and function studies.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:4548, CHEBI:23727
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Formula C56H92O29
Net Charge 0
Average Mass 1229.323
Monoisotopic Mass 1228.57243
InChI InChI=1S/C56H92O29/c1-19-7-10-56(75-17-19)20(2)31-45(85-56)37(67)32-22-6-5-21-11-26(24(61)12-55(21,4)23(22)8-9-54(31,32)3)76-50-42(72)39(69)44(30(16-60)80-50)81-53-48(47(36(66)29(15-59)79-53)83-49-40(70)33(63)25(62)18-74-49)84-52-43(73)46(35(65)28(14-58)78-52)82-51-41(71)38(68)34(64)27(13-57)77-51/h19-53,57-73H,5-18H2,1-4H3/t19-,20+,21+,22-,23+,24-,25-,26-,27-,28-,29-,30-,31+,32-,33+,34-,35+,36-,37+,38+,39-,40-,41-,42-,43-,44+,45-,46+,47+,48-,49+,50-,51+,52+,53+,54-,55+,56-/m1/s1
InChIKey UVYVLBIGDKGWPX-KUAJCENISA-N
SMILES [H][C@@]12O[C@]3(CC[C@@H](C)CO3)[C@@H](C)[C@]1([H])[C@@]1(C)CC[C@@]3([H])[C@@]([H])(CC[C@@]4([H])C[C@@H](O[C@@H]5O[C@H](CO)[C@H](O[C@@H]6O[C@H](CO)[C@@H](O)[C@H](O[C@@H]7OC[C@@H](O)[C@H](O)[C@H]7O)[C@H]6O[C@@H]6O[C@H](CO)[C@H](O)[C@H](O[C@@H]7O[C@H](CO)[C@@H](O)[C@H](O)[C@H]7O)[C@H]6O)[C@H](O)[C@H]5O)[C@H](O)C[C@]34C)[C@]1([H])[C@@H]2O
Metabolite of Species Details
Digitalis purpurea (NCBI:txid4164) See: PubMed
Roles Classification
Chemical Role(s): detergent
A surfactant (or a mixture containing one or more surfactants) having cleaning properties in dilute solutions.
Biological Role(s): plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via saponin )
Application(s): detergent
A surfactant (or a mixture containing one or more surfactants) having cleaning properties in dilute solutions.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing digitonin (CHEBI:27729) has functional parent digitogenin (CHEBI:28431)
digitonin (CHEBI:27729) has role detergent (CHEBI:27780)
digitonin (CHEBI:27729) has role plant metabolite (CHEBI:76924)
digitonin (CHEBI:27729) is a pentasaccharide derivative (CHEBI:63566)
digitonin (CHEBI:27729) is a spirostanyl glycoside (CHEBI:38091)
IUPAC Name
(25R)-2α,15β-dihydroxy-5α-spirostan-3β-yl β-D-glucopyranosyl-(1→3)-β-D-galactopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→3)]-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside
Synonyms Sources
Digitin ChemIDplus
Digitonin KEGG COMPOUND
Manual Xrefs Databases
4976216 ChemSpider
C00003574 KNApSAcK
C00765 KEGG COMPOUND
CN101829228 Patent
CPD0-1629 MetaCyc
Digitonin Wikipedia
LMST01080003 LIPID MAPS
View more database links
Registry Numbers Types Sources
11024-24-1 CAS Registry Number KEGG COMPOUND
11024-24-1 CAS Registry Number ChemIDplus
78654 Beilstein Registry Number Beilstein
Citations Waiting for Citations Types Sources
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Last Modified
17 August 2021