Structure Database (LMSD)

Common Name
tomatine
Systematic Name
(22S,25S)-5α-spirosolan-3β-yl β-D-glucopyranosyl-(1-2)-[β-D-xylopyranosyl-(1-3)]-β-D-glucopyranosyl-(1-4)-β-D-galactopyranoside
Synonyms
  • (3beta,5alpha,22beta,25S)-spirosolan-3-yl O-beta-D-glucopyranosyl-(1->2)-O-(beta-D-xylopyranosyl)-(1->3)-O-beta-D-glucopyranosyl-(1->4)-beta-D-galactopyranoside
  • A''-Tomatidine
  • Tomatine
  • alpha-tomatine
  • lycopersicin
LM ID
LMST01150015
Formula
C50H83NO21
Exact Mass
Calculate m/z
1033.545764
Status
Active
Show lipids differing only in stereochemistry/bond geometry

Classification

Category
Main Class
Sub Class
Sterol Lipids [ST]
Sterols [ST01]
Solanidines and alkaloid derivatives [ST0115]

String Representations

InChiKey (Click to copy)
REJLGAUYTKNVJM-SGXCCWNXSA-N
InChi (Click to copy)
InChI=1S/C50H83NO21/c1-20-7-12-50(51-15-20)21(2)32-28(72-50)14-26-24-6-5-22-13-23(8-10-48(22,3)25(24)9-11-49(26,32)4)65-45-40(63)37(60)41(31(18-54)68-45)69-47-43(71-46-39(62)36(59)34(57)29(16-52)66-46)42(35(58)30(17-53)67-47)70-44-38(61)33(56)27(55)19-64-44/h20-47,51-63H,5-19H2,1-4H3/t20-,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-/m0/s1
SMILES (Click to copy)
O([C@H]1CC[C@@]2(C)[C@]([H])(C1)CC[C@@]1([H])[C@@]3([H])[C@@](C)([C@@]4([H])[C@H](C)[C@@]5(O[C@@]4([H])C3)CC[C@H](C)CN5)CC[C@@]12[H])[C@@H]1O[C@H](CO)[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O[C@@H]3OC[C@@H](O)[C@H](O)[C@H]3O)[C@H]2O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@H]1O

Other Databases

Wikipedia
tomatine
KEGG ID
C10827
CHEBI ID
9630
PubChem CID
28523
Cayman ID
16024

Calculated Physicochemical Properties

Heavy Atoms 72
Rings 10
Aromatic Rings 0
Rotatable Bonds 11
Van der Waals Molecular Volume 945.55
Topological Polar Surface Area 348.21
Hydrogen Bond Donors 13
Hydrogen Bond Acceptors 21
logP 5.03
Molar Refractivity 258.02

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Updated at
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