CHEBI:45030 - 5-(2-ethoxyethyl)-5-[4-(4-fluorophenoxy)phenoxy]barbituric acid

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ChEBI Name 5-(2-ethoxyethyl)-5-[4-(4-fluorophenoxy)phenoxy]barbituric acid
ChEBI ID CHEBI:45030
Definition A member of the class of barbiturates that is barbituric acid in which the hydrogens at position 5 are replaced by 2-ethoxyethyl and 4-(4-fluorophenoxy)phenoxy groups. It is a potent and selective inhibitor of matrix MMP-13 (metalloproteinase-13, collagenase 3).
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:33201, CHEBI:45025
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Formula C20H19FN2O6
Net Charge 0
Average Mass 402.37310
Monoisotopic Mass 402.12271
InChI InChI=1S/C20H19FN2O6/c1-2-27-12-11-20(17(24)22-19(26)23-18(20)25)29-16-9-7-15(8-10-16)28-14-5-3-13(21)4-6-14/h3-10H,2,11-12H2,1H3,(H2,22,23,24,25,26)
InChIKey XRSYNYGEEYTXJV-UHFFFAOYSA-N
SMILES CCOCCC1(Oc2ccc(Oc3ccc(F)cc3)cc2)C(=O)NC(=O)NC1=O
Roles Classification
Biological Role(s): matrix metalloproteinase inhibitor

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 )
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ChEBI Ontology
Outgoing 5-(2-ethoxyethyl)-5-[4-(4-fluorophenoxy)phenoxy]barbituric acid (CHEBI:45030) has role matrix metalloproteinase inhibitor (CHEBI:50664)
5-(2-ethoxyethyl)-5-[4-(4-fluorophenoxy)phenoxy]barbituric acid (CHEBI:45030) is a barbiturates (CHEBI:22693)
IUPAC Name
5-(2-ethoxyethyl)-5-[4-(4-fluorophenoxy)phenoxy]pyrimidine-2,4,6(1H,3H,5H)-trione
Manual Xrefs Databases
DB08388 DrugBank
PFD PDBeChem
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Registry Numbers Types Sources
9950446 Beilstein Registry Number Beilstein
9950446 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
15780611 PubMed citation Europe PMC
Last Modified
02 September 2013