基本情報
- CAS
13073-35-3- 標準SMILES
CCSCC[C@H](N)C(=O)O- InChIKey
GGLZPLKKBSSKCX-YFKPBYRVSA-N- 分子式
- C6H13NO2S
- 平均分子量
- 163.24 g/mol
- 単同位体質量
- 163.06669983
概要
L-ethionine is an S-ethylhomocysteine that has S-configuration at the chiral centre. It has a role as an antimetabolite and a carcinogenic agent. It is an enantiomer of a D-ethionine.
名称と識別子
- 優先名称
- L-Ethionine
- IUPAC
- (2S)-2-amino-4-ethylsulfanylbutanoic acid
- 現地名
- L-エチオニン
- 英語名
- L-Ethionine
- 分子式
- C6H13NO2S
- 分子量
- 163.24
名称と別名
L-Ethionine13073-35-3EthionineS-Ethyl-L-homocysteineL-S-EthylhomocysteineL-2-Amino-4-(ethylthio)butyric acidWX1BN24WZTDTXSID5020578Butyric acid, 2-amino-4-(ethylene)-, L-CHEBI:4886HOMOCYSTEINE S-ETHYL ETHERNSC-82393
名称をさらに表示
L-エチオニン(S)-2-アミノ-4-(エチルチオ)ブタン酸エチオニン(+)-S-エチル-L-ホモシステイン(S)-4-(エチルチオ)-2-アミノ酪酸[S,(+)]-2-アミノ-4-(エチルチオ)酪酸(+)-エチオニン(S)-2-アミノ-4-(エチルチオ)酪酸S-エチル-L-ホモシステイン(2S)-2-アミノ-4-(エチルスルファニル)ブタン酸H-ETH-OHNsc82393l-butyricaciL-Ethionine>L-ETHIONINE 98+%L -ETHIONINE 99%s-ethyl-homocystein
RefChem:138409DTXCID30578235-966-4L-Homocysteine, S-ethyl-(S)-2-amino-4-(ethylthio)butanoic acid(+)-ethionine(2S)-2-amino-4-ethylsulfanylbutanoic acid(2S)-2-amino-4-(ethylsulfanyl)butanoic acid
データベース識別子
物性
構造計算による物性
- XLogP
- -1.5
- 極性表面積
- 88.6 Ų
- 水素結合供与体数
- 2
- 水素結合受容体数
- 4
- 回転可能結合数
- 5
- 重原子数
- 10
- 形式電荷
- 0
- 複雑度
- 108
実験および物理化学的性質
Chemical ClassesOther Uses -> Biochemical Research
Color/FormCrystals
Melting Point272-274 °C (decomposes)
Optical RotationSPECIFIC OPTICAL ROTATION +25.1 DEG @ 24 °C/D, +20.1 DEG @ 23 °C/D (1 N HCL)
Physical DescriptionSolid; [Merck Index]
Other Experimental Properties
DECOMP @ 257-260 DEG /DL-FORM/
CRYSTALS, /DL-FORM & L-FORM/
DECOMP @ 272-274 °C
物理化学的性質
- 融点
- 280 °C · 280 °C (dec.)(lit.)
- 比旋光度
- 24 · D24 +25.1°; D23 +20.1° (1N HCl) (Armstrong, Lewis)
- 比重(密度)
- 1.085 · 1.085 (estimate)
- 屈折率
- 22 ° · 22 ° (C=1, 1mol/L HCl)
- 貯蔵温度
- 2 · Keep in dark place,Sealed in dry,2-8°C
- 溶解性
- 水性酸（わずかに）、水（わずかに）
- 外見
- 個体
- 沸点
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
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 39 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
危険有害性情報
Hazards SummaryCauses diffuse hepatitis and acute renal failure in acute oral studies of rats; Causes hepatitis in 35-day constant oral studies of rats; [RTECS] A hepatotoxin; [HSDB] A skin and strong eye irritant; Targets the liver; [Sigma-Aldrich MSDS]
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
安全と保護具
Disposal Methods
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
毒性情報
Interactions
DL-METHIONINE @ 0.6-0.8% IN DIET FED SIMULTANEOUSLY WITH ETHIONINE PREVENTS DEVELOPMENT OF LIVER TUMORS /IN RATS/. /ETHIONINE/
IN RATS...LABELLING IN VIVO OF LIVER PROTEINS BY TRITIATED DIMETHYLNITROSAMINE WAS...LARGELY INHIBITED BY...ETHIONINE... /ETHIONINE/
...TUMOR OF THE IRIS HAS BEEN OBSERVED IN RATS' EYES AFTER REPEATED SYSTEMIC ADMIN IN COMBINATION WITH N-2-FLUORENYLACETAMIDE.
化学と産業
薬理情報
Mechanism of Action
/ETHIONINE/ INHIBITS THE INCORPORATION OF METHIONINE AND GLYCINE INTO RAT PROTEIN IN VIVO AND THE CONVERSION OF METHIONINE INTO CYSTEINE. ETHIONINE IS DEETHYLATED, AND THE ETHYL GROUP APPEARS IN ANALOGUES OF METABOLITES KNOWN TO PARTICIPATE IN TRANSMETHYLATION REACTIONS, EG ETHYL CHOLINE. IN THE RAT IT IS ITSELF INCORPORATED INTO ABNORMAL PROTEINS COMPETITIVELY, BUT ITS AFFINITY IS ONLY 1/600 THAT OF METHIONINE. /ETHIONINE/
... The mechanism by which ethionine induces fatty liver is thought to be due to the inhibition of synthesis of very low density lipoprotein. ... The synthesis of lipoprotein is correlated with liver estradiol receptor concn, /an examination/ of the effect of ethionine on estradiol receptor concn in rat liver /was examined/. Estradiol receptor concn in both cytosolic and nuclear fractions were greatly decr by a single injection of ethionine at a dose of 0.5 mg/kg bw. In particular, the decr in nuclear receptor concn was observed a few hr after the injection and correlated with the decr in triglyceride content in the very low density lipoprotein fraction. /Data suggests/ that liver estradiol receptor is involved in the pathogenesis of ethionine induced fatty liver of rats.
Metabolism/Metabolites
S-ADENOSYLETHIONINE IS A SUGGESTED ALKYLATING METABOLITE OF CARCINOGEN ETHIONINE. /FROM TABLE/
ETHIONINE IS BIOACTIVATED IN LIVER TO S-ADENOSYL-L-ETHIONINE, WHICH CAN ETHYLATE MACROMOLECULES CAUSING CELL ABNORMALITIES. ADENOSYLETHIONINE IS CHEM STABLE & CAN PENETRATE TO EMBRYONIC TISSUES & CAUSE TERATOGENIC EFFECTS.
IN URINE OF TREATED RATS, 4 PRINCIPAL ETHIONINE EXCRETORY PRODUCTS WERE IDENTIFIED...N-ACETYLETHIONINE SULFOXIDE, S-ADENOSYLETHIONINE, ETHIONINE SULFOXIDE, & FREE ETHIONINE.
MeSH Pharmacological ClassificationDrugs that are chemically similar to naturally occurring metabolites, but differ enough to interfere with normal metabolic pathways. (From AMA Drug Evaluations Annual, 1994, p2033)
Absorption, Distribution and ExcretionIN RAT KIDNEY RADIOACTIVITY WAS MAINLY LOCALIZED IN MEDULLA FOLLOWING INJECTION WITH (14)C-ETHIONINE, WHEREAS (14)C-METHIONINE WAS HOMOGENEOUSLY DISTRIBUTED THROUGHOUT WHOLE PARENCHYMA IN RATS.
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