Details
Stereochemistry | EPIMERIC |
Molecular Formula | C6H14N4O2.C4H7NO2S |
Molecular Weight | 307.37 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 2 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OC(=O)C1CSCN1.N[C@@H](CCCNC(N)=N)C(O)=O
InChI
InChIKey=JEOQACOXAOEPLX-WCCKRBBISA-N
InChI=1S/C6H14N4O2.C4H7NO2S/c7-4(5(11)12)2-1-3-10-6(8)9;6-4(7)3-1-8-2-5-3/h4H,1-3,7H2,(H,11,12)(H4,8,9,10);3,5H,1-2H2,(H,6,7)/t4-;/m0./s1
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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Enhanced potency of human Sonic hedgehog by hydrophobic modification. | 2001 Apr 10 |
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Oxidation of L-thiazolidine-4-carboxylate by delta1-pyrroline-5-carboxylate reductase in Escherichia coli. | 2001 Jun |
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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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Retinoic acid exacerbates experimental radiation nephropathy. | 2002 Feb |
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Novel dipeptide macrocycles from 4-oxo, -thio, and -amino-substituted proline derivatives. | 2002 May 31 |
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Improvement of the macrophage functions in prematurely ageing mice by a diet supplemented with thiolic antioxidants. | 2004 |
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Formaldehyde scavenging from peritoneal dialysis solutions using reduced aminothiol compounds. | 2004 Apr |
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Bombesin antagonists inhibit proangiogenic factors in human experimental breast cancers. | 2004 Jan 12 |
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Thioproline inhibits development of esophageal adenocarcinoma induced by gastroduodenal reflux in rats. | 2004 May |
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A one-pot total synthesis of crambin. | 2004 May 3 |
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Impact of cis-proline analogs on peptide conformation. | 2006 Apr 5 |
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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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Successful computer guided planned synthesis of (4R)-thiazolidine carboxylic acid and its 2-substituted analogues as urease inhibitors. | 2006 May |
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Conformational studies of proline-, thiaproline- and dimethylsilaproline-containing diketopiperazines. | 2006 Oct |
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Ingestion of thioproline suppresses rat esophageal adenocarcinogenesis caused by duodenogastroesophageal reflux. | 2007 Dec |
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Dietary thioproline decreases spontaneous food intake and increases survival and neurological function in mice. | 2007 Jan |
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Liver fluke induces cholangiocarcinoma. | 2007 Jul |
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Identification of gene markers for formaldehyde exposure in humans. | 2007 Oct |
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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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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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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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UIB16M6D10
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260-857-3
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DTXSID00973205
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9883032
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57631-15-9
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