Details
Stereochemistry | RACEMIC |
Molecular Formula | C4H7NO2S |
Molecular Weight | 133.169 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OC(=O)C1CSCN1
InChI
InChIKey=DZLNHFMRPBPULJ-UHFFFAOYSA-N
InChI=1S/C4H7NO2S/c6-4(7)3-1-8-2-5-3/h3,5H,1-2H2,(H,6,7)
Timonacic or thioproline (4-Thiazolidinecarboxylic acid) is the product of condensation between cysteine and formaldehyde. Dietary timonacic slows the aging process in mammals and prolongs their life span. It exerts antioxidant and antineoplastic actions however its mechanism of action is elusive. Timonacic (brand names Heparegen or Arbitol) is used for the treatment of liver diseases.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17115892
Curator's Comment: Timonacic (thioproline) is CNS active in animals. No human data available.
Originator
Sources: http://pubs.acs.org/doi/abs/10.1021/ja01280a050
Curator's Comment: reference retrieved from http://www.drugfuture.com/chemdata/timonacic.html
Approval Year
PubMed
Title | Date | PubMed |
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Screening for new compounds with antiherpes activity. | 1984 Oct |
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New water-soluble prodrugs of HIV protease inhibitors based on O-->N intramolecular acyl migration. | 2002 Dec |
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The amount of thiolic antioxidant ingestion needed to improve several immune functions is higher in aged than in adult mice. | 2002 Feb |
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A diet supplemented with thiolic anti-oxidants improves leucocyte function in two strains of prematurely ageing mice. | 2002 Nov |
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Formaldehyde scavenging from peritoneal dialysis solutions using reduced aminothiol compounds. | 2004 Apr |
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Synthesis, calpain inhibitory activity, and cytotoxicity of P2-substituted proline and thiaproline peptidyl aldehydes and peptidyl alpha-ketoamides. | 2006 Aug 24 |
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Thioproline prevents carcinogenesis in the remnant stomach induced by duodenal reflux. | 2006 Jun 18 |
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Ingestion of thioproline suppresses rat esophageal adenocarcinogenesis caused by duodenogastroesophageal reflux. | 2007 Dec |
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An expanded set of amino acid analogs for the ribosomal translation of unnatural peptides. | 2007 Oct 3 |
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Determination of thiazolidine-4-carboxylates in urine by chloroformate derivatization and gas chromatography-electron impact mass spectrometry. | 2007 Sep |
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Investigation toward multi-epitope vaccine candidates using native chemical ligation. | 2008 |
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Lithium thiazolidine-4-carboxylate: synthesis, spectroscopic characterization and preliminary in vitro cytotoxic studies in human HeLa cells. | 2008 Dec 1 |
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Detection of endogenous DNA adducts, O-carboxymethyl-2'-deoxyguanosine and 3-ethanesulfonic acid-2'-deoxycytidine, in the rat stomach after duodenal reflux. | 2008 Sep |
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An atom economic synthesis and antitubercular evaluation of novel spiro-cyclohexanones. | 2009 Jul 1 |
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Synthesis, structure and structure-activity relationship analysis of 3-tert-butoxycarbonyl-2-arylthiazolidine-4-carboxylic acid derivatives as potential antibacterial agents. | 2009 Oct |
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A regio- and stereoselective 1,3-dipolar cycloaddition for the synthesis of novel spiro-pyrrolothiazolyloxindoles and their antitubercular evaluation. | 2010 Dec |
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A facile 1,3-dipolar cycloaddition of azomethine ylides to 2-arylidene-1,3-indanediones: synthesis of dispiro-oxindolylpyrrolothiazoles and their antimycobacterial evaluation. | 2010 Dec 15 |
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A highly atom economic, chemo-, regio- and stereoselective synthesis and evaluation of spiro-pyrrolothiazoles as antitubercular agents. | 2010 Jan 1 |
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Murine models of premature ageing for the study of diet-induced immune changes: improvement of leucocyte functions in two strains of old prematurely ageing mice by dietary supplementation with sulphur-containing antioxidants. | 2010 Nov |
Patents
Sample Use Guides
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6318968
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NCI_THESAURUS |
C2132
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C2354
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C003438
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m10872
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)