基本情報
- CAS
17406-45-0- 標準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- 分子式
- C50H83NO21
- 平均分子量
- 1,034.2 g/mol
- 単同位体質量
- 1,033.54575866
概要
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.
名称と識別子
- 優先名称
- 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
- 現地名
- トマチン
- 英語名
- TOMATINE
- 分子式
- C50H83NO21
- 分子量
- 1034.19
名称と別名
TomatineLycopersicinalpha-Tomatine17406-45-0TomatinA''-TomatidineTomatidine, glycosideDTXSID5040413CHEBI:9630NSC-23444031U6547O08DTXCID3020413
名称をさらに表示
トマチン[(22S,25S)-5α-スピロソラン-3β-イル]4-O-[2-O-(β-D-グルコピラノシル)-3-O-(β-D-キシロピラノシル)-β-D-グルコピラノシル]-β-D-ガラクトピラノシドα-トマチンリコペルシシントマチン (トマト由来)α-トマチン (トマト由来)リコペルシシン (トマト由来)リコペルシシン(SEE TOMATトマチン(2S,3R,4S,5S,6R)-2-{[(2S,3R,4S,5R,6R)-2-{[(2R,3R,4R,5R,6R)-4,5-ジヒドロキシ-2-(ヒドロキシメチル)-6-[(1R,2S,4S,5'S,6S,7S,8R,9S,12S,13S,16S,18S)-5',7,9,13-テトラメチル-5-オキサスピロ[ペンタシクロ[10.8.0.02,9.04,8.013,18]イコサン-6,2'-ピペリジン]オキシ]オキサン-3-イル]オキシ}-5-ヒドロキシ-6-(ヒドロキシメチル)-4-{[(2S,3R,4S,5R)-3,4,5-トリヒドロキシオキサン-2-イル]オキシ}オキサン-3-イル]オキシ}-6-(ヒドロキシメチル)オキサン-3,4,5-トリオールTomatine [for Cholesterol assay]omatineTomatie
物性
構造計算による物性
- XLogP
- -0.7
- 極性表面積
- 338 Ų
- 水素結合供与体数
- 13
- 水素結合受容体数
- 22
- 回転可能結合数
- 11
- 重原子数
- 72
- 形式電荷
- 0
- 複雑度
- 1,840
実験および物理化学的性質
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]
物理化学的性質
- 融点
- 300 · 300-305°C
安全と法規制
安全情報は参考情報です。供給元の安全データシート（SDS）、適用法令、専門家による評価に代わるものではありません。
GHS分類
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.
危険有害性情報
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%)
毒性情報
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.
TOMATINE FORMED A COMPLEX WITH CHOLESTEROL IN VIVO IN RAT INTESTINE. TOMATINE (1% IN DIET) DECREASED THE UPTAKE OF DIETARY CHOLESTEROL BY THE LIVERS AND INCREASED THE RATES OF HEPATIC AND INTESTINAL CHOLESTEROL SYNTHESIS AND THE STEROL EXCRETION WITHOUT AFFECTING THE BILE ACID SECRETION.
化学と産業
薬理情報
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)
用途と製造
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
PRECIPITATING AGENT FOR STEROIDS; PROPOSED AS AN ALTERNATE PRECIPITANT TO DIGITONIN
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