CHEBI:16294 - barbituric acid

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ChEBI Name barbituric acid
ChEBI ID CHEBI:16294
Definition A barbiturate, the structure of which is that of perhydropyrimidine substituted at C-2, -4 and -6 by oxo groups. Barbituric acid is the parent compound of barbiturate drugs, although it is not itself pharmacologically active.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:2993, CHEBI:22692
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Formula C4H4N2O3
Net Charge 0
Average Mass 128.08620
Monoisotopic Mass 128.022
InChI InChI=1S/C4H4N2O3/c7-2-1-3(8)6-4(9)5-2/h1H2,(H2,5,6,7,8,9)
InChIKey HNYOPLTXPVRDBG-UHFFFAOYSA-N
SMILES O=C1CC(=O)NC(=O)N1
Roles Classification
Biological Role(s): xenobiotic
A xenobiotic (Greek, xenos "foreign"; bios "life") is a compound that is foreign to a living organism. Principal xenobiotics include: drugs, carcinogens and various compounds that have been introduced into the environment by artificial means.
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): 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 )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing barbituric acid (CHEBI:16294) has role xenobiotic (CHEBI:35703)
barbituric acid (CHEBI:16294) is a barbiturates (CHEBI:22693)
barbituric acid (CHEBI:16294) is conjugate acid of barbiturate (CHEBI:29745)
barbituric acid (CHEBI:16294) is conjugate acid of barbiturate(1−) (CHEBI:77938)
barbituric acid (CHEBI:16294) is conjugate acid of barbiturate(2−) (CHEBI:57718)
Incoming 6-oxouridine 5'-phosphate (CHEBI:41150) has functional parent barbituric acid (CHEBI:16294)
alloxan (CHEBI:76451) has functional parent barbituric acid (CHEBI:16294)
butalbital (CHEBI:102524) has functional parent barbituric acid (CHEBI:16294)
dialuric acid (CHEBI:76452) has functional parent barbituric acid (CHEBI:16294)
hexobarbital (CHEBI:5706) has functional parent barbituric acid (CHEBI:16294)
secobarbital (CHEBI:9073) has functional parent barbituric acid (CHEBI:16294)
barbiturate (CHEBI:29745) is conjugate base of barbituric acid (CHEBI:16294)
barbiturate(1−) (CHEBI:77938) is conjugate base of barbituric acid (CHEBI:16294)
barbiturate(2−) (CHEBI:57718) is conjugate base of barbituric acid (CHEBI:16294)
IUPAC Name
pyrimidine-2,4,6(1H,3H,5H)-trione
Synonyms Sources
2,4,6(1H,3H,5H)-pyrimidinetrione NIST Chemistry WebBook
Barbituric acid KEGG COMPOUND
Barbitursäure ChEBI
Malonylharnstoff ChEBI
Malonylurea KEGG COMPOUND
Database Links Databases
Barbituric_acid Wikipedia
C00813 KEGG COMPOUND
HMDB0041833 HMDB
View more database links
Registry Numbers Types Sources
101571 Gmelin Registry Number Gmelin
120502 Beilstein Registry Number Beilstein
120502 Reaxys Registry Number Reaxys
67-52-7 CAS Registry Number KEGG COMPOUND
67-52-7 CAS Registry Number NIST Chemistry WebBook
67-52-7 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
22139480 PubMed citation Europe PMC
23038042 PubMed citation Europe PMC
23915243 PubMed citation Europe PMC
3654008 PubMed citation Europe PMC
Last Modified
16 July 2015