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Substance Name: alpha-Tomatine, hydrochloride
RN: 17605-83-3
InChIKey: GBMIDMBWAJHPIS-UQDWSYJXSA-N

Note

  • An alkaloid that occurs in the extract of leaves of wild tomato plants. It has been found to inhibit the growth of various fungi and bacteria. It is used as a precipitating agent for steroids. (From The Merck Index, 11th ed)

Classification Code

  • Skin / Eye Irritant

Molecular Formula

  • C50-H83-N-O21.Cl-H

Molecular Weight

  • 1070.65
 
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Names and Synonyms

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 hydrochloride
  • Tomatine hydrochloride

Systematic Names

  • alpha-Tomatine, hydrochloride
  • beta-D-Galactopyranoside, (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)-, hydrochloride

Registry Numbers

CAS Registry Number

  • 17605-83-3

System Generated Number

  • 0017605833

Molecular Formulas

Molecular Formula

  • C50-H83-N-O21.Cl-H

Molecular Formula Fragments

  • C50-H83-N-O21
  • Cl-H
  • COMPONENT

Structure Descriptors

InChI

1S/C50H83NO21.ClH/c1-20-7-12-49(51-15-20)21(2)32-28(70-49)14-26-24-6-5-22-13-23(8-10-47(22,3)25(24)9-11-48(26,32)4)50(72-46-41(64)38(61)35(58)30(17-53)67-46)43(69-44-39(62)33(56)27(55)19-65-44)42(36(59)31(18-54)71-50)68-45-40(63)37(60)34(57)29(16-52)66-45;/h20-46,51-64H,5-19H2,1-4H3;1H/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+;/m1./s1

InChIKey

GBMIDMBWAJHPIS-UQDWSYJXSA-N

Smiles

O([C@]1([C@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)CO2)[C@@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)[C@H](O2)CO)[C@@H](O)[C@@H](O1)CO)[C@@H]1CC[C@@]2([C@@H]3CC[C@@]4([C@@H]5[C@H](C[C@@H]4[C@@H]3CC[C@@H]2C1)O[C@@]1([C@@H]5C)NC[C@@H](CC1)C)C)C)[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO.Cl

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intravenous 18mg/kg (18mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: EXCITEMENT
Toxicology and Applied Pharmacology. Vol. 3, Pg. 39, 1961.