Skip Navigation
ChemIDplus A TOXNET DATABASE LiteBrowseAdvanced

Substance Name: Tomatine
RN: 17406-45-0
UNII: 31U6547O08
InChIKey: REJLGAUYTKNVJM-SGXCCWNXSA-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)

Molecular Formula

  • C50-H83-N-O21

Molecular Weight

  • 1034.1917
 

Classification Codes

  • Anti-Infective Agents
  • Antifungal Agents
  • Indicators and Reagents
  • Mutation Data
  • Natural Product
* denotes mobile formatted website

Links to Resources


Search for this InChIKey on the Web

Names and Synonyms

Name of Substance

  • Tomatine

MeSH Heading

  • Tomatine

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
  • 4-27-00-01954 (Beilstein Handbook Reference)
  • A''-Tomatidine
  • AI3-17141
  • alpha-Tomatine
  • 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)-
  • BRN 0078250
  • EINECS 241-429-5
  • HSDB 3558
  • Lycopersicin
  • NSC 234440
  • NSC 9223
  • Tomatidine, glycoside
  • Tomatin
  • Tomatine
  • UNII-31U6547O08

Systematic Names

  • 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)-
  • Tomatine

Registry Numbers

CAS Registry Number

  • 17406-45-0

FDA UNII

  • 31U6547O08

System Generated Number

  • 0017406450

Structure Descriptors

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

InChIKey

REJLGAUYTKNVJM-SGXCCWNXSA-N

Smiles

C[C@H]1CC[C@]2([C@H]([C@H]3[C@@H](O2)C[C@@H]4[C@@]3(CC[C@H]5[C@H]4CC[C@@H]6[C@@]5(CC[C@@H](C6)O[C@H]7[C@@H]([C@H]([C@H]([C@H](O7)CO)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O[C@H]9[C@@H]([C@H]([C@@H](CO9)O)O)O)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)O)O)C)C)C)NC1

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 25mg/kg (25mg/kg)   Schweizerische Zietschrift fuer Allgemeine Pathologie und Bakteriologie. Vol. 22, Pg. 557, 1959.
mouse LD50 oral 500mg/kg (500mg/kg)   Food and Cosmetics Toxicology. Vol. 17, Pg. 61, 1979.
mouse LD50 subcutaneous 1gm/kg (1000mg/kg)   "CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980Vol. 8(2), Pg. 218, 1982.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 270 deg C   EXP
log P (octanol-water) -1.700 (none)   EST
Atmospheric OH Rate Constant 3.66E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.