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Structure Database (LMSD)

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Common Name

Digitonin

Systematic 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

Digitin
3-O-(Glcb1-3Galb1-2-(Xylb1-3)-Glcb1-4Galb)-(25R)-5alpha-spirostan-2alpha,3beta,15beta-triol

LM ID

LMST01080003

Formula

C₅₆H₉₂O₂₉

Exact Mass

Calculate m/z

1228.572435

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

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Classification

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Digitalis purpurea (#4164)

Magnoliopsida (#3398)

Über saponine der spirostanolreihe—IX : Die konstitution des digitonins,
Tetrahedron, 1963

DOI: 10.1016/S0040-4020(01)98548-5

String Representations

InChiKey (Click to copy)

UVYVLBIGDKGWPX-KUAJCENISA-N

InChi (Click to copy)

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

SMILES (Click to copy)

C1[C@@]2([H])[C@@](C)([C@@]3([H])CC[C@]4(C)[C@H]5[C@@H]([C@]6(OC[C@@H](CC6)C)O[C@H]5[C@@H](O)[C@@]4([H])[C@]3([H])CC2)C)C[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H](O[C@H]2[C@H](O[C@H]3[C@H](O)[C@@H](O[C@H]4[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O4)[C@@H](O)[C@@H](CO)O3)[C@@H](O[C@H]3[C@H](O)[C@@H](O)[C@H](O)CO3)[C@H](O)[C@@H](CO)O2)[C@@H](CO)O1