Basic information
- CAS
17406-45-0- Standard SMILES
C[C@H]1CC[C@]2(NC1)O[C@H]1C[C@H]3[C@@H]4CC[C@H]5C[C@@H](O[C@@H]6O[C@H](CO)[C@H](O[C@@H]7O[C@H](CO)[C@@H](O)[C@H](O[C@@H]8OC[C@@H](O)[C@H](O)[C@H]8O)[C@H]7O[C@@H]7O[C@H](CO)[C@@H](O)[C@H](O)[C@H]7O)[C@H](O)[C@H]6O)CC[C@]5(C)[C@H]4CC[C@]3(C)[C@H]1[C@@H]2C- InChIKey
REJLGAUYTKNVJM-SGXCCWNXSA-N- Molecular formula
- C50H83NO21
- Average molar mass
- 1,034.2 g/mol
- Monoisotopic mass
- 1,033.54575866
Overview
Tomatine is a steroid alkaloid that is tomatidine in which the hydroxy group at position 3 is linked to lycotetraose, a tetrasaccharide composed of two units of D-glucose, one unit of D-xylose, and one unit of D-galactose. It has a role as an antifungal agent, a phytotoxin and an immunological adjuvant. It is a glycoalkaloid, a glycoside, a steroid alkaloid, a tetrasaccharide derivative and an alkaloid antibiotic. It is functionally related to a tomatidine.
Names & identifiers
- Preferred name
- Tomatine
- IUPAC
- (2S,3R,4S,5S,6R)-2-[(2S,3R,4S,5R,6R)-2-[(2R,3R,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-[(1R,2S,4S,5'S,6S,7S,8R,9S,12S,13S,16S,18S)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-piperidine]-16-yl]oxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)-4-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
- English name
- TOMATINE
- Molecular formula
- C50H83NO21
- Molecular weight
- 1034.19
Names & synonyms
TomatineLycopersicinalpha-Tomatine17406-45-0TomatinA''-TomatidineTomatidine, glycosideDTXSID5040413CHEBI:9630NSC-23444031U6547O08DTXCID3020413
Show more names
Tomatine [for Cholesterol assay]omatineTomatieNSC 9223a-TomatineNSC 234440LYOCPERSICIN
NSC-9223beta-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)-(22S,25S)-5alpha-spirosolan-3beta-yl beta-D-glucopyranosyl-(1-2)-[beta-D-xylopyranosyl-(1-3)]-beta-D-glucopyranosyl-(1-4)-beta-D-galactopyranoside(22S,25S)-5alpha-spirosolan-3beta-yl beta-D-glucopyranosyl-(1-2)-(beta-D-xylopyranosyl-(1-3))-beta-D-glucopyranosyl-(1-4)-beta-D-galactopyranosideRefChem:1903612-(2-(4,5-dihydroxy-2-(hydroxymethyl)-6-(5',7,9,13-tetramethylspiro(5-oxapentacyclo(10.8.0.02,9.04,8.013,18)icosane-6,2'-piperidine)-16-yl)oxyoxan-3-yl)oxy-5-hydroxy-6-(hydroxymethyl)-4-(3,4,5-trihydroxyoxan-2-yl)oxyoxan-3-yl)oxy-6-(hydroxymethyl)oxane-3,4,5-triol241-429-5(2S,3R,4S,5S,6R)-2-((2S,3R,4S,5R,6R)-2-((2R,3R,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-((1R,2S,4S,5'S,6S,7S,8R,9S,12S,13S,16S,18S)-5',7,9,13-tetramethylspiro(5-oxapentacyclo(10.8.0.02,9.04,8.013,18)icosane-6,2'-piperidine)-16-yl)oxyoxan-3-yl)oxy-5-hydroxy-6-(hydroxymethyl)-4-((2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl)oxyoxan-3-yl)oxy-6-(hydroxymethyl)oxane-3,4,5-triol
Properties
Computed structural properties
- XLogP
- -0.7
- Topological polar surface area
- 338 Ų
- Hydrogen bond donors
- 13
- Hydrogen bond acceptors
- 22
- Rotatable bonds
- 11
- Heavy atoms
- 72
- Formal charge
- 0
- Complexity
- 1,840
Experimental & physicochemical properties
Chemical ClassesBiological Agents -> Plant Toxins
LipidsLipids -> Sterol Lipids [ST] -> Sterols [ST01] -> Solanidines and alkaloid derivatives [ST0115]
Color/Form
NEEDLES FROM METHANOL
WHITE CRYSTALS
SolubilitySOLUBLE IN ETHANOL, METHANOL, DIOXANE, PROPYLENE GLYCOL; PRACTICALLY INSOLUBLE IN WATER, ETHER, PETROLEUM ETHER
Melting Point263-268 °C
Optical Rotation
SPECIFIC OPTICAL ROTATION: -18 DEG @ 22 °C/D (C= 0.55 IN PYRIDINE)
SPECIFIC OPTICAL ROTATION: -30 DEG @ 20 °C/D (PYRIDINE)
Physical DescriptionWhite solid; [HSDB] Faintly beige powder; [MSDSonline]
Collision Cross Section311.78 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 5 reports by companies from 1 notifications to the ECHA C&L Inventory.
Hazard information
Regulatory Information
.beta.-D-Galactopyranoside, (3.beta.,5.alpha.,22.beta.,25S)-spirosolan-3-yl O-.beta.-D-glucopyranosyl-(1â2)-O-[.beta.-D-xylopyranosyl-(1â3)]-O-.beta.-D-glucopyranosyl-(1â4)-: Does not have an individual approval but may be used under an appropriate group standard
Hazards SummaryHas demonstrated growth inhibition of some fungi and bacteria; [Merck Index] Emergency treatment: Irritants; [HSDB] May cause irritation; [MSDSonline]
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Toxicology
InteractionsTOMATINE REDUCED THE GROWTH ENHANCED BY 10-4 MOLAR INDOLE-3-ACETIC ACID.
Natural Pollution SourcesOCCURS IN THE EXTRACT OF LEAVES OF WILD TOMATO PLANTS.
Non-Human Toxicity Excerpts
...IRRITANT PROPERTIES /OF TOMATINE/ HAVE BEEN EVALUATED IN RABBITS BY APPLYING A 5% OINTMENT TO THE EYE. IT PROVED TO BE IRRITATING, AND ON REPEATED APPLICATION AFFECTED PARTICULARLY THE CONJUNCTIVA OF THE LIDS, MAKING THE LIDS EDEMATOUS. HOWEVER, THE EYES RECOVERED COMPLETELY A FEW DAYS AFTER EXPOSURE WAS DISCONTINUED.
Chemistry & industry
Pharmacology
Mechanism of Action
SIX GLYCOALKALOIDS AND ONE AGLYCONE WERE TESTED FOR CARDIOTONIC ACTIVITIES AND COMPARED WITH K-STROPHANTHOSIDE BY USE OF THE ISOLATED FROG HEART. THE DECREASING ORDER OF POTENCY WAS AS FOLLOWS: K-STROPHANTHOSIDE GREATER THAN TOMATINE GREATER THAN ALPHA-CHACONINE EQUAL TO ALPHA-SOLANINE GREATER THAN DEMISSINE EQUAL TO COMMERSONINE GREATER THAN BETA-CHACONINE GREATER THAN SOLANIDINE. CARDIOTONIC ACTIVITY WAS DIRECTLY RELATED TO THE NUMBER OF SUGARS IN THE MOLECULE IN WHICH THE GLYCOALKALOIDS HAD A COMMON AGLYCONE.
REMOVAL OF 1 OR MORE SUGAR RESIDUES FROM THE ALPHA-TOMATINE MOLECULE MARKEDLY DECREASED ITS FUNGITOXICITY. ALTHOUGH THE PARTIAL HYDROLYSIS OF ALPHA-TOMATINE DID NOT GREATLY AFFECT ITS SURFACTANT PROPERTIES, IT DID DESTROY THE ABILITY OF THE ALKALOID TO FORM A COMPLEX WITH CHOLESTEROL.
MeSH Pharmacological Classification
Substances that prevent infectious agents or organisms from spreading or kill infectious agents in order to prevent the spread of infection.
Substances that destroy fungi by suppressing their ability to grow or reproduce. They differ from FUNGICIDES, INDUSTRIAL because they defend against fungi present in human or animal tissues.
Substances used for the detection, identification, analysis, etc. of chemical, biological, or pathologic processes or conditions. Indicators are substances that change in physical appearance, e.g., color, at or approaching the endpoint of a chemical titration, e.g., on the passage between acidity and alkalinity. Reagents are substances used for the detection or determination of another substance by chemical or microscopical means, especially analysis. Types of reagents are precipitants, solvents, oxidizers, reducers, fluxes, and colorimetric reagents. (From Grant & Hackh's Chemical Dictionary, 5th ed, p301, p499)
Uses & manufacturing
Uses
Extracted from leaves of wild tomato plants; [Merck Index] Used as precipitating agent for steroids, a plant fungicide, and a therapeutic antifungal and anti-infective agent; [HSDB]
Farming (Pesticides) [Category: Industry]
MEDICATION
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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