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L-에티오닌

L-Ethionine

HCID 25674
노트반응
기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
부분 구조 검색유사 구조 찾기

기본 정보

CAS
13073-35-3
표준 SMILES
CCSCC[C@H](N)C(=O)O
InChIKey
GGLZPLKKBSSKCX-YFKPBYRVSA-N
분자식
C6H13NO2S
평균 분자량
163.24 g/mol
단동위원소 질량
163.06669983

개요

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.

이름 및 식별자

우선 이름
L-Ethionine
IUPAC
(2S)-2-amino-4-ethylsulfanylbutanoic acid
현지명
L-에티오닌
영어명
L-Ethionine
분자식
C6H13NO2S
분자량
163.24

이름 및 동의어

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
이름 더 보기
L-에티오닌H-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

데이터베이스 식별자

CAS
13073-35-3
PubChem CID
25674
DTXSID
DTXSID5020578
ChEMBL
CHEMBL203187
ChEBI
CHEBI:4886
UNII
WX1BN24WZT

물성

구조 계산 물성

XLogP
-1.5
극성 표면적
88.6 Ų
수소 결합 공여자 수
2
수소 결합 수용자 수
4
회전 가능 결합 수
5
무거운 원자 수
10
형식 전하
0
복잡도
108

실험 및 물리화학적 성질

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 · 3건

DECOMP @ 257-260 DEG /DL-FORM/

CRYSTALS, /DL-FORM & L-FORM/

DECOMP @ 272-274 °C

물리화학적 성질

녹는점
280 °C · 280 °C (dec.)(lit.)
밀도
1.085 · 1.085 (estimate)
굴절률
22 ° · 22 ° (C=1, 1mol/L HCl)
저장 조건
2 · Keep in dark place,Sealed in dry,2-8°C
용해도
산성 수용액(약간), 물(약간) 에 용해됨
물리적 상태
고체
끓는 점
310.4 · 310.4±37.0 °C(Predicted)

안전 및 규제

안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.

GHS 분류

GHS Classification · 4건

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.

유해성 정보

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%)

안전 및 보호

Disposal Methods · 1건

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.

독성 정보

Interactions · 4건

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.

화학 및 산업

약리 정보

Mechanism of Action · 2건

/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 · 3건

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.

관련 반응

0건
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화합물 노트

불러오는 중…

이 페이지에서기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
EC Number
235-966-4
Nikkaji
J9.260F
산도 계수 (pKa)
2.23 · 2.23±0.10(Predicted)
색상
흰색에서 황백색까지
Merck
14 · 14,3738
InChI
1S/C6H13NO2S/c1-2-10-4-3-5(7)6(8)9/h5H,2-4,7H2,1H3,(H,8,9)/t5-/m0/s1
InChIKey
GGLZPLKKBSSKCX-YFKPBYRVSA-N
SMILES
CCSCC[C@H](N)C(O)=O
EPA
L-Ethionine (13073-35-3)

화학적 성질

White Solid

The effects of SA3443, a novel disulfide cmpd on acute liver injuries induced by carbon tetrachloride, D-galactosamine and DL-ethionine were studied in rats or mice. SA3443 (100-300 mg/kg, po) significantly suppressed the incr of serum transaminase activity and liver triglyceride content in the carbon tetrachloride or DL-ethionine induced model. ...

Adverse EffectsOccupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.
Human Toxicity Excerpts · 2건

WHEN GIVEN ORALLY TO SMALL SERIES OF PATIENTS WITH FAR ADVANCED NEOPLASIAS IN DOSES OF 0.67 TO 45 G/DAY (TOTAL DOSES 9.7 TO 55 G), ETHIONINE PRODUCED THE FOLLOWING SYMPTOMS WHEN THE DIET WAS DEFICIENT IN METHIONINE: IMPAIRMENT OF LIVER FUNCTION, PROTEINURIA, HEMATURIA, DERMATITIS, LEUKOPENIA, THROMBOCYTOPENIA AND DIARRHEA. DETERIORATION OF MENTAL STATUS & FRANK TOXIC PSYCHOSIS ... ALSO OCCURRED.

These agents /including ethionine/ cause hepatic damage by interfering with essential metabolic pathways, which leads to cytotoxic (necrosis or steatosis) and/or cholestatic (biliary stasis) injury patterns. /Ethionine/

Non-Human Toxicity Excerpts · 5건

ETHIONINE, A HEPATOCARCINOGEN, ETHYLATED CELLULAR CONSTITUENTS OF LIVER INCL DNA ON PROLONGED FEEDING TO RATS. SUGGESTED MECHANISM INVOLVES S-ADENOSYL-L-ETHIONINE AS /ETHYL/ DONOR... HOWEVER.../EXPECTATION /WOULD BE/ THAT 5-ETHYLCYTOSINE WOULD BE FORMED IN DNA... ONLY ETHYLATED BASE DETECTED WAS 7-ETHYLGUANINE.

OPTIMAL INDUCTION OF /RAT/ LIVER TUMORS REQUIRES CONTINUOUS FEEDING OF SYNTHETIC DL-ETHIONINE (0.25% IN DIET) FOR...5 MO. ... THOUGH ETHIONINE CAUSES ACUTE DEGENERATIVE LESIONS IN PANCREATIC ACINI & PREVENTS ALLOXAN DIABETES, NO PANCREATIC TUMORS...REPORTED. /DL-FORM/

CHEM TERATOGENS THAT REQUIRE METAB OR BIOACTIVATION TO ELECTROPHILIC REACTANTS INCL...ETHIONINE... MOST FREQUENTLY IT IS LIVER THAT PRODUCES VARIETY OF ELECTROPHILIC REACTANTS THAT, LIKE ALKYLATING AGENTS, COVALENTLY BIND TO MACROMOLECULES.

ETHIONINE...INTERFERENCE WITH METHIONINE FOR AVAILABLE ATP LEADS TO DIMINUTION OF LIPOPROTEIN-TRANSPORT MOLECULES & RETENTION OF FAT.

For more Non-Human Toxicity Excerpts (Complete) data for (L)-ETHIONINE (15 total), please visit the HSDB record page.

Antidote and Emergency TreatmentL-METHIONINE IS ANTAGONISTIC TO THE EFFECTS OF ETHIONINE.

안전 데이터

wgk
3
tsca
TSCA listed
rtecs
ES6825300
독성
rat,LD,intraperitoneal,> 1gm/kg (1000mg/kg),LIVER: OTHER CHANGESLIVER: CHANGES IN LIVER WEIGHT,Acta Pathologica Japonica. Vol. 39, Pg. 281, 1989.
HS 번호
2930.90.4950
risk_code
36/37/38
hazard_code
Xi
safety_code
26
Hazard Classifications
Eye Irrit. 2Skin Irrit. 2STOT SE 3
스토리지 클래스
11 - Combustible Solids
유해 물질 데이터
13073-35-3(Hazardous Substances Data)

용도 및 제조

Uses · 3건

An antimetabolite and methionine antagonist that interferes with amino acid incorporation into proteins and with cellular ATP utilization. It also produces liver neoplasms. [ChemIDplus] Toxic analogue of the essential amino acid methionine; Produced by various microorganisms such as E. coli; Used as an experimental carcinogen and in biological research; Not commercially produced in the US; [HSDB]

EXPTL CARCINOGEN

BIOLOGICAL RESEARCH CHEMICAL

U.S. Exports · 2건

(1977) No Data

(1979) No Data

U.S. Imports · 2건

(1977) No Data

(1979) No Data

U.S. Production · 3건

(1977) NOT PRODUCED COMMERCIALLY IN US

(1979) NOT PRODUCED COMMERCIALLY IN US

(1992) No data

Methods of Manufacturing · 2건

REACTION OF ETHANETHIOL WITH ACROLEIN FOLLOWED BY TREATMENT WITH HYDROGEN CYANIDE & AMMONIA AND HYDROLYSIS

...FROM ETHANETHIOL & ACROLEIN, PURIFICATION VIA ZN SALT: NORTON US PATENT 2,840,587 (1958 TO DOW). PREPN OF DL-...& L-FORM: ARMSTRONG, LEWIS, J ORG CHEM 16, 749 (1951).

General Manufacturing Information · 3건

L-Homocysteine, S-ethyl-: INACTIVE

.../ETHIONINE/ WAS SYNTHESIZED AS AN ANTIMETABOLITE TO L-METHIONINE & USED IN STUDY OF TRANSMETHYLATION REACTIONS IN RELATION TO THE BIOCHEMISTRY OF THIS ESSENTIAL AMINO ACID.

ETHIONINE...THE TOXIC ANALOGUE OF AMINO ACID METHIONINE, IS PRODUCED BY E COLI & VARIOUS OTHER MICROORGANISMS.

응용 분야

용도Ethionine-induced inhibition of protein synthesis and lowering of ATP level in the liver.

상·하류 제품 정보

상류 원료

N-아세틸-DL-에티오닌S-3,6-bis(2-chloroethyl)piperazine-2,5-dioneN-포르밀-DL-에티오닌O-Acetyl-L-homoserine hydrochlorideDL-EthionineNsc164657에틸메르캅탄요오드화에틸

하류 제품

2-Oxopentanoic acid

공급사67 곳

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추가 설명

정의ChEBI: An S-ethylhomocysteine that has S-configuration at the chiral centre.