Term: | digitonin |
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Accession: | CHEBI:27729
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Definition: | A spirostanyl glycoside that is digitogenin in which the 3-hydroxy group is substituted by a beta-D-glucopyranosyl-(1->3)-beta-D-galactopyranosyl-(1->2)-[beta-D-xylopyranosyl-(1->3)]-beta-D-glucopyranosyl-(1->4)-beta-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. |
Synonyms: | exact_synonym: | (25R)-2alpha,15beta-dihydroxy-5alpha-spirostan-3beta-yl beta-D-glucopyranosyl-(1->3)-beta-D-galactopyranosyl-(1->2)-[beta-D-xylopyranosyl-(1->3)]-beta-D-glucopyranosyl-(1->4)-beta-D-galactopyranoside |
| related_synonym: | Digitin; Formula=C56H92O29; 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 |
| alt_id: | CHEBI:23727; CHEBI:4548 |
| xref: | Beilstein:78654; CAS:11024-24-1; Chemspider:4976216; KEGG:C00765; KNApSAcK:C00003574; LIPID_MAPS_instance:LMST01080003 |
| xref_mesh: | MESH:D004072 |
| xref: | MetaCyc:CPD0-1629; PMID:11603432; PMID:19049416; PMID:20072627; PMID:21752631; PMID:21951169; PMID:22480420; PMID:23062361; PMID:23146422; PMID:25412206; PMID:25555589; PMID:26349826; PMID:26569199; PMID:27147060; PMID:27518122; PMID:28333465; PMID:28551523; PMID:30240438; PMID:32280324; PMID:33333059; PMID:33428933; PMID:34330992; PMID:34351328; Patent:CN101829228; Wikipedia:Digitonin |
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