2-thiobarbituric acid (CHEBI:33202)

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ChEBI Name	2-thiobarbituric acid

ChEBI ID	CHEBI:33202

Definition	A barbiturate, the structure of which is that of barbituric acid in which the oxygen at C-2 is replaced by sulfur.

Stars	This entity has been manually annotated by the ChEBI Team.

Supplier Information	ChemicalBook:CB5251676, eMolecules:884223, eMolecules:27678705, ZINC000008727446

Download	Molfile XML SDF

Wikipedia	License
Thiobarbituric acid is an organic compound and a heterocycle. It is used as a reagent in assaying malondialdehyde (the TBARS assay of lipid peroxidation). It is also used in Kodak Fogging Developer FD-70, part of the Kodak Direct Positive Film Developing Outfit for making black and white slides (positives).
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Formula

C4H4N2O2S

Net Charge

Average Mass

144.15284

Monoisotopic Mass

143.99935

InChI

InChI=1S/C4H4N2O2S/c7-2-1-3(8)6-4(9)5-2/h1H2,(H2,5,6,7,8,9)

InChIKey

RVBUGGBMJDPOST-UHFFFAOYSA-N

SMILES

O=C1CC(=O)NC(=S)N1

Roles Classification
Biological Role(s):	allergen A chemical compound, or part thereof, which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy. GABA modulator A substance that does not act as agonist or antagonist but does affect the gamma-aminobutyric acid receptor-ionophore complex. GABA-A receptors appear to have at least three allosteric sites at which modulators act: a site at which benzodiazepines act by increasing the opening frequency of gamma-aminobutyric acid-activated chloride channels; a site at which barbiturates act to prolong the duration of channel opening; and a site at which some steroids may act. (via barbiturates )

Application(s):	reagent A substance used in a chemical reaction to detect, measure, examine, or produce other substances. GABA modulator A substance that does not act as agonist or antagonist but does affect the gamma-aminobutyric acid receptor-ionophore complex. GABA-A receptors appear to have at least three allosteric sites at which modulators act: a site at which benzodiazepines act by increasing the opening frequency of gamma-aminobutyric acid-activated chloride channels; a site at which barbiturates act to prolong the duration of channel opening; and a site at which some steroids may act. (via barbiturates )

ChEBI Ontology
Outgoing	2-thiobarbituric acid (CHEBI:33202) has role allergen (CHEBI:50904) 2-thiobarbituric acid (CHEBI:33202) has role reagent (CHEBI:33893) 2-thiobarbituric acid (CHEBI:33202) is a barbiturates (CHEBI:22693)

Incoming	thiopental (CHEBI:102166) has functional parent 2-thiobarbituric acid (CHEBI:33202)

IUPAC Name

2-sulfanylidenedihydropyrimidine-4,6(1H,5H)-dione

Synonyms	Sources
2-thioxodihydropyrimidine-4,6(1H,5H)-dione	IUPAC
dihydro-2-thioxo-4,6(1H,5H)-pyrimidinedione	ChemIDplus
thiobarbituric acid	ChemIDplus

Citations

Last Modified

07 March 2019