digitonin (CHEBI:27729)

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CHEBI:27729 - digitonin

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ChEBI ID	CHEBI:27729
ChEBI Name	digitonin
Stars
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.
Secondary ChEBI IDs	CHEBI:4548, CHEBI:23727
Last Modified	17 August 2021
Downloads	Molfile

Formula	C56H92O29
Net Charge	0
Average Mass	1229.323
Monoisotopic Mass	1228.57243
SMILES	[H][C@@]12CC[C@]3([H])[C@]([H])(CC[C@@]4(C)[C@@]3([H])[C@H](O)[C@]3([H])O[C@]5(CC[C@@H](C)CO5)[C@@H](C)[C@]43[H])[C@@]1(C)C[C@@H](O)[C@H](O[C@@H]1O[C@H](CO)[C@H](O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O[C@@H]4OC[C@@H](O)[C@H](O)[C@H]4O)[C@H]3O[C@@H]3O[C@H](CO)[C@H](O)[C@H](O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)[C@H]3O)[C@H](O)[C@H]1O)C2
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

Wikipedia

Species of Metabolite	Component	Source	Comments
Digitalis purpurea (ncbitaxon:4164)	-	PubMed (32280324)

Roles Classification

Chemical Role:	detergent A surfactant (or a mixture containing one or more surfactants) having cleaning properties in dilute solutions.
Biological Roles:	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.
Application:	detergent A surfactant (or a mixture containing one or more surfactants) having cleaning properties in dilute solutions.

ChEBI Ontology

Outgoing Relation(s)
	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	Source
Digitonin	KEGG COMPOUND
Digitin	ChemIDplus

Manual Xrefs	Databases
C00765	KEGG COMPOUND
C00003574	KNApSAcK
LMST01080003	LIPID MAPS
CPD0-1629	MetaCyc
Digitonin	Wikipedia
4976216	ChemSpider
CN101829228	Patent

Registry Numbers	Sources
Beilstein:78654	Beilstein
CAS:11024-24-1	KEGG COMPOUND
CAS:11024-24-1	ChemIDplus

Citations