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Details

Stereochemistry ABSOLUTE
Molecular Formula C6H13NO2S
Molecular Weight 163.238
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ETHIONINE, D-

SMILES

CCSCC[C@@H](N)C(O)=O

InChI

InChIKey=GGLZPLKKBSSKCX-RXMQYKEDSA-N
InChI=1S/C6H13NO2S/c1-2-10-4-3-5(7)6(8)9/h5H,2-4,7H2,1H3,(H,8,9)/t5-/m1/s1

HIDE SMILES / InChI

Molecular Formula C6H13NO2S
Molecular Weight 163.238
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Ethionine is a non-proteinogenic amino acid structurally related to methionine, with an ethyl group in place of the methyl group. Ethionine is an antimetabolite and methionine antagonist. It prevents amino acid incorporation into proteins and interferes with cellular use of adenosine triphosphate (ATP). Ethionine is a far more potent inhibitor of RNA synthesis than of protein synthesis. While both stereoisomers were active, the L isomer was a more potent inhibitor of RNA synthesis than was the D isomer. In male mice, 3 hr after 20 mg/kg L-ethionine, RNA synthesis was inhibited 80%, while after D-ethionine it was inhibited only 51%. Ethionine was a potent inhibitor of wool growth in sheep; the L- and D-isomers appeared equally effective. Because of these pharmacological effects, ethionine is highly toxic and is a potent carcinogen. L and D-ethionine have being shown to be equally effective in producing tissue damage in rats and mice. The L- and ID-isomers of ethionine are equally effective in producing pancreatic and renal changes in the rat as well as fatty infiltration of the liver and pancreatic damage in the albino mouse.

Originator

Curator's Comment: Ethionine was first synthesized by Dyer in 1938

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P53634|||Q7Z3G7
Gene ID: 1075.0
Gene Symbol: CTSC
Target Organism: Homo sapiens (Human)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Silencing MAT2A gene by RNA interference inhibited cell growth and induced apoptosis in human hepatoma cells.
2007 May
Patents

Sample Use Guides

In Vivo Use Guide
The acute, 7-day LD50 in Swiss mice of D-ethionine administered intraperitoneally, was determined as 185 mg/kg with 95% confidence limits of 163 and 210 mg/kg.
Route of Administration: Intraperitoneal
20 mM L-ethionine and D-ethionine enhanced the activities of prolidase I and prolidase II from normal human erythrocytes, and prolidase activity in erythrocyte lysates from a patient with prolidase deficiency against the iminodipeptides tested. The enhancing effect of D-ethionine was more significant than that of L-ethionine.
Substance Class Chemical
Created
by admin
on Sat Dec 16 08:52:43 GMT 2023
Edited
by admin
on Sat Dec 16 08:52:43 GMT 2023
Record UNII
91GB0NN2T6
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ETHIONINE, D-
Systematic Name English
D-ETHIONINE
Systematic Name English
BUTYRIC ACID, 2-AMINO-4-(ETHYLTHIO)-, D-
Systematic Name English
NSC-97927
Code English
D-HOMOCYSTEINE, S-ETHYL-
Systematic Name English
Code System Code Type Description
HSDB
3570
Created by admin on Sat Dec 16 08:52:43 GMT 2023 , Edited by admin on Sat Dec 16 08:52:43 GMT 2023
PRIMARY
EPA CompTox
DTXSID80102149
Created by admin on Sat Dec 16 08:52:43 GMT 2023 , Edited by admin on Sat Dec 16 08:52:43 GMT 2023
PRIMARY
NSC
97927
Created by admin on Sat Dec 16 08:52:43 GMT 2023 , Edited by admin on Sat Dec 16 08:52:43 GMT 2023
PRIMARY
CAS
535-32-0
Created by admin on Sat Dec 16 08:52:43 GMT 2023 , Edited by admin on Sat Dec 16 08:52:43 GMT 2023
PRIMARY
PUBCHEM
92124
Created by admin on Sat Dec 16 08:52:43 GMT 2023 , Edited by admin on Sat Dec 16 08:52:43 GMT 2023
PRIMARY
FDA UNII
91GB0NN2T6
Created by admin on Sat Dec 16 08:52:43 GMT 2023 , Edited by admin on Sat Dec 16 08:52:43 GMT 2023
PRIMARY
ECHA (EC/EINECS)
208-612-1
Created by admin on Sat Dec 16 08:52:43 GMT 2023 , Edited by admin on Sat Dec 16 08:52:43 GMT 2023
PRIMARY