Compounds > 7-chloro-3-[cyclopropyl(oxo)methyl]-4-hydroxy-1H-quinolin-2-one
Page last updated: 2024-11-13

7-chloro-3-[cyclopropyl(oxo)methyl]-4-hydroxy-1H-quinolin-2-one

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Cross-References

ID SourceID
PubMed CID54687453
CHEMBL ID115225
CHEBI ID92179
SCHEMBL ID1997392

Synonyms (37)

Synonym
HMS3266L13
BRD-K10176267-001-01-7
NCGC00024741-01 ,
tocris-0705
BIOMOL-NT_000184
NCGC00024741-02
BPBIO1_001180
l-701252 ,
CHEMBL115225
7-chloro-3-(cyclopropanecarbonyl)-2-hydroxy-1h-quinolin-4-one
A809114
7-chloranyl-3-cyclopropylcarbonyl-2-oxidanyl-1h-quinolin-4-one
7-chloro-3-[cyclopropyl(oxo)methyl]-2-hydroxy-1h-quinolin-4-one
151057-13-5
7-chloro-3-(cyclopropanecarbonyl)-4-hydroxyquinolin-2(1h)-one
FT-0643463
l-701,252
SCHEMBL1997392
7-chloro-3-(cyclopropylcarbonyl)-4-hydroxy-2(1h)-quinolinone
AKOS024458613
2(1h)-quinolinone,7-chloro-3-(cyclopropylcarbonyl)-4-hydroxy-
7-chloro-3-(cyclopropyl-carbonyl)-4-hydroxy-2(1h)-quinolinone
DTXSID60715805
SR-01000597630-1
sr-01000597630
CHEBI:92179
7-chloro-3-(cyclopropanecarbonyl)-4-hydroxy-1h-quinolin-2-one
J-008775
7-chloro-3-[cyclopropyl(oxo)methyl]-4-hydroxy-1h-quinolin-2-one
Q27163953
HMS3675B19
HMS3411B19
BRD-K10176267-001-02-5
MS-23720
SB70336
HY-101101
CS-0020826
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (2)

ClassDescription
quinolone
hydroxyquinoline
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (29)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
phosphopantetheinyl transferaseBacillus subtilisPotency44.66840.141337.9142100.0000AID1490
aldehyde dehydrogenase 1 family, member A1Homo sapiens (human)Potency25.11890.011212.4002100.0000AID1030
regulator of G-protein signaling 4Homo sapiens (human)Potency26.67950.531815.435837.6858AID504845
cytochrome P450 2D6 isoform 1Homo sapiens (human)Potency0.10000.00207.533739.8107AID891
cytochrome P450 3A4 isoform 1Homo sapiens (human)Potency0.00320.031610.279239.8107AID884; AID885
Gamma-aminobutyric acid receptor subunit piRattus norvegicus (Norway rat)Potency0.00321.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit beta-1Rattus norvegicus (Norway rat)Potency0.00321.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit deltaRattus norvegicus (Norway rat)Potency0.00321.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit gamma-2Rattus norvegicus (Norway rat)Potency0.00321.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-5Rattus norvegicus (Norway rat)Potency0.00321.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-3Rattus norvegicus (Norway rat)Potency0.00321.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit gamma-1Rattus norvegicus (Norway rat)Potency0.00321.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-2Rattus norvegicus (Norway rat)Potency0.00321.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-4Rattus norvegicus (Norway rat)Potency0.00321.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit gamma-3Rattus norvegicus (Norway rat)Potency0.00321.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-6Rattus norvegicus (Norway rat)Potency0.00321.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-1Rattus norvegicus (Norway rat)Potency0.00321.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit beta-3Rattus norvegicus (Norway rat)Potency0.00321.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit beta-2Rattus norvegicus (Norway rat)Potency0.00321.000012.224831.6228AID885
Inositol monophosphatase 1Rattus norvegicus (Norway rat)Potency22.38721.000010.475628.1838AID1457
GABA theta subunitRattus norvegicus (Norway rat)Potency0.00321.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit epsilonRattus norvegicus (Norway rat)Potency0.00321.000012.224831.6228AID885
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Glutamate receptor ionotropic, NMDA 1 Rattus norvegicus (Norway rat)IC50 (µMol)0.41970.00071.600310.0000AID143473; AID145257; AID145260
Glutamate receptor ionotropic, NMDA 2A Rattus norvegicus (Norway rat)IC50 (µMol)0.41970.00071.630610.0000AID143473; AID145257; AID145260
Glutamate receptor ionotropic, NMDA 2BRattus norvegicus (Norway rat)IC50 (µMol)0.41970.00061.525710.0000AID143473; AID145257; AID145260
Glutamate receptor ionotropic, NMDA 2CRattus norvegicus (Norway rat)IC50 (µMol)0.41970.00071.747210.0000AID143473; AID145257; AID145260
Glutamate receptor ionotropic, NMDA 2DRattus norvegicus (Norway rat)IC50 (µMol)0.41970.00071.741110.0000AID143473; AID145257; AID145260
Glutamate receptor ionotropic, NMDA 3BRattus norvegicus (Norway rat)IC50 (µMol)0.41970.00071.741110.0000AID143473; AID145257; AID145260
Glutamate receptor ionotropic, NMDA 3ARattus norvegicus (Norway rat)IC50 (µMol)0.41970.00071.741110.0000AID143473; AID145257; AID145260
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Other Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Glutamate receptor ionotropic, NMDA 1 Rattus norvegicus (Norway rat)Kb3.40000.00592.09697.0000AID143250
Glutamate receptor ionotropic, NMDA 2A Rattus norvegicus (Norway rat)Kb3.40000.00592.41137.0000AID143250
Glutamate receptor ionotropic, NMDA 2BRattus norvegicus (Norway rat)Kb3.40000.00592.41137.0000AID143250
Glutamate receptor ionotropic, NMDA 2CRattus norvegicus (Norway rat)Kb3.40000.00592.41137.0000AID143250
Glutamate receptor ionotropic, NMDA 2DRattus norvegicus (Norway rat)Kb3.40000.00592.41137.0000AID143250
Glutamate receptor ionotropic, NMDA 3BRattus norvegicus (Norway rat)Kb3.40000.00592.41137.0000AID143250
Glutamate receptor ionotropic, NMDA 3ARattus norvegicus (Norway rat)Kb3.40000.00592.41137.0000AID143250
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Ceullar Components (2)

Processvia Protein(s)Taxonomy
plasma membraneGamma-aminobutyric acid receptor subunit gamma-2Rattus norvegicus (Norway rat)
endoplasmic reticulum membraneGlutamate receptor ionotropic, NMDA 1 Rattus norvegicus (Norway rat)
plasma membraneGlutamate receptor ionotropic, NMDA 1 Rattus norvegicus (Norway rat)
plasma membraneGamma-aminobutyric acid receptor subunit alpha-1Rattus norvegicus (Norway rat)
plasma membraneGamma-aminobutyric acid receptor subunit beta-2Rattus norvegicus (Norway rat)
endoplasmic reticulum membraneGlutamate receptor ionotropic, NMDA 2A Rattus norvegicus (Norway rat)
plasma membraneGlutamate receptor ionotropic, NMDA 2A Rattus norvegicus (Norway rat)
endoplasmic reticulum membraneGlutamate receptor ionotropic, NMDA 2BRattus norvegicus (Norway rat)
plasma membraneGlutamate receptor ionotropic, NMDA 2BRattus norvegicus (Norway rat)
endoplasmic reticulum membraneGlutamate receptor ionotropic, NMDA 2CRattus norvegicus (Norway rat)
plasma membraneGlutamate receptor ionotropic, NMDA 2CRattus norvegicus (Norway rat)
endoplasmic reticulum membraneGlutamate receptor ionotropic, NMDA 2DRattus norvegicus (Norway rat)
plasma membraneGlutamate receptor ionotropic, NMDA 2DRattus norvegicus (Norway rat)
endoplasmic reticulum membraneGlutamate receptor ionotropic, NMDA 3BRattus norvegicus (Norway rat)
plasma membraneGlutamate receptor ionotropic, NMDA 3BRattus norvegicus (Norway rat)
endoplasmic reticulum membraneGlutamate receptor ionotropic, NMDA 3ARattus norvegicus (Norway rat)
plasma membraneGlutamate receptor ionotropic, NMDA 3ARattus norvegicus (Norway rat)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (13)

Assay IDTitleYearJournalArticle
AID145260In vitro inhibition of [3H]glycine at NMDA receptor1994Journal of medicinal chemistry, Nov-25, Volume: 37, Issue:24
The glycine site on the NMDA receptor: structure-activity relationships and therapeutic potential.
AID143473Affinity for the glycine binding site on rat N-methyl-D-aspartate glutamate receptor 1, determined by displacement of the glycine site antagonist [3H]L-689,560 from rat cortical membranes1997Journal of medicinal chemistry, Dec-05, Volume: 40, Issue:25
Effect of plasma protein binding on in vivo activity and brain penetration of glycine/NMDA receptor antagonists.
AID113804Anticonvulsant activity measured by its ability to protect against audiogenic seizure in DBA/2 mice when dosed intraperitoneally 30 min prior to seizure induction.1997Journal of medicinal chemistry, Dec-05, Volume: 40, Issue:25
Effect of plasma protein binding on in vivo activity and brain penetration of glycine/NMDA receptor antagonists.
AID203505Human serum albumin index was measured by retention time on an HPLC column containing human albumin1997Journal of medicinal chemistry, Dec-05, Volume: 40, Issue:25
Effect of plasma protein binding on in vivo activity and brain penetration of glycine/NMDA receptor antagonists.
AID145257Binding affinity towards NMDA receptor to displace [3H]-L-689,560 from rat cortical membranes1993Journal of medicinal chemistry, Oct-29, Volume: 36, Issue:22
3-Acyl-4-hydroxyquinolin-2(1H)-ones. Systemically active anticonvulsants acting by antagonism at the glycine site of the N-methyl-D-aspartate receptor complex.
AID143250In vitro inhibition of cortical slice at NMDA receptor1994Journal of medicinal chemistry, Nov-25, Volume: 37, Issue:24
The glycine site on the NMDA receptor: structure-activity relationships and therapeutic potential.
AID186990Antagonistic activity against NMDA-induced response in rat cortical slice1993Journal of medicinal chemistry, Oct-29, Volume: 36, Issue:22
3-Acyl-4-hydroxyquinolin-2(1H)-ones. Systemically active anticonvulsants acting by antagonism at the glycine site of the N-methyl-D-aspartate receptor complex.
AID19623Partition coefficient (logP)1997Journal of medicinal chemistry, Dec-05, Volume: 40, Issue:25
Effect of plasma protein binding on in vivo activity and brain penetration of glycine/NMDA receptor antagonists.
AID112661In vivo antagonist activity against seizures elicited by audiogenic administered intra peritoneally in mice1994Journal of medicinal chemistry, Nov-25, Volume: 37, Issue:24
The glycine site on the NMDA receptor: structure-activity relationships and therapeutic potential.
AID131696Effective dose of compound required to protect audiogenic seizure in DBA/2 mice administered ip1993Journal of medicinal chemistry, Oct-29, Volume: 36, Issue:22
3-Acyl-4-hydroxyquinolin-2(1H)-ones. Systemically active anticonvulsants acting by antagonism at the glycine site of the N-methyl-D-aspartate receptor complex.
AID1347154Primary screen GU AMC qHTS for Zika virus inhibitors2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1508630Primary qHTS for small molecule stabilizers of the endoplasmic reticulum resident proteome: Secreted ER Calcium Modulated Protein (SERCaMP) assay2021Cell reports, 04-27, Volume: 35, Issue:4
A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome.
AID493017Wombat Data for BeliefDocking1993Journal of medicinal chemistry, Oct-29, Volume: 36, Issue:22
3-Acyl-4-hydroxyquinolin-2(1H)-ones. Systemically active anticonvulsants acting by antagonism at the glycine site of the N-methyl-D-aspartate receptor complex.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (5)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's3 (60.00)18.2507
2000's0 (0.00)29.6817
2010's0 (0.00)24.3611
2020's2 (40.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.87

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index12.87 (24.57)
Research Supply Index1.79 (2.92)
Research Growth Index4.66 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.87)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (20.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other4 (80.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
1-aminocyclopropane-1-carboxylic acid
1-aminocyclopropanecarboxylic acid : A non-proteinogenic alpha-amino acid consisting of cyclopropane having amino and carboxy substituents both at the 1-position.		3.0810amino acid zwitterion;
monocarboxylic acid;
non-proteinogenic alpha-amino acid		ethylene releasers;
plant metabolite
glycine
[no description available]		3.0810alpha-amino acid;
amino acid zwitterion;
proteinogenic amino acid;
serine family amino acid		EC 2.1.2.1 (glycine hydroxymethyltransferase) inhibitor;
fundamental metabolite;
hepatoprotective agent;
micronutrient;
neurotransmitter;
NMDA receptor agonist;
nutraceutical
5,7-dichlorokynurenic acid
5,7-dichlorokynurenic acid: potent antagonist at the N-methyl-D-aspartate receptor-associated glycine binding site		3.4920quinolines
6,7-dichloroquinoxaline-2,3-dione
[no description available]		3.0810quinoxaline derivative
7-chlorokynurenic acid
7-chlorokynurenic acid: selective antagonist at the glycine modulatory site of the N-methyl-D-aspartate receptor complex; structure given in first source. 7-chlorokynurenic acid : A quinolinemonocarboxylic acid that is quinaldic acid which is substituted by a hydroxy group at position 4 and by a chlorine at position 7. It is a potent NMDA glutamate receptor antagonist which antagonizes the strychnine-insensitive glycine site of the NMDA receptor. It also prevents neurodegeneration produced by quinolinic acid.		3.4920organochlorine compound;
quinolinemonocarboxylic acid		neuroprotective agent;
NMDA receptor antagonist
diazepam
Diazepam: A benzodiazepine with anticonvulsant, anxiolytic, sedative, muscle relaxant, and amnesic properties and a long duration of action. Its actions are mediated by enhancement of GAMMA-AMINOBUTYRIC ACID activity.. diazepam : A 1,4-benzodiazepinone that is 1,3-dihydro-2H-1,4-benzodiazepin-2-one substituted by a chloro group at position 7, a methyl group at position 1 and a phenyl group at position 5.		1.99101,4-benzodiazepinone;
organochlorine compound		anticonvulsant;
anxiolytic drug;
environmental contaminant;
sedative;
xenobiotic
kynurenic acid
Kynurenic Acid: A broad-spectrum excitatory amino acid antagonist used as a research tool.. kynurenic acid : A quinolinemonocarboxylic acid that is quinoline-2-carboxylic acid substituted by a hydroxy group at C-4.		3.0810monohydroxyquinoline;
quinolinemonocarboxylic acid		G-protein-coupled receptor agonist;
human metabolite;
neuroprotective agent;
nicotinic antagonist;
NMDA receptor antagonist;
Saccharomyces cerevisiae metabolite
cycloserine
Cycloserine: Antibiotic substance produced by Streptomyces garyphalus.. D-cycloserine : A 4-amino-1,2-oxazolidin-3-one that has R configuration. It is an antibiotic produced by Streptomyces garyphalus or S. orchidaceus and is used as part of a multi-drug regimen for the treatment of tuberculosis when resistance to, or toxicity from, primary drugs has developed. An analogue of D-alanine, it interferes with bacterial cell wall synthesis in the cytoplasm by competitive inhibition of L-alanine racemase (which forms D-alanine from L-alanine) and D-alanine--D-alanine ligase (which incorporates D-alanine into the pentapeptide required for peptidoglycan formation and bacterial cell wall synthesis).		3.08104-amino-1,2-oxazolidin-3-one;
organonitrogen heterocyclic antibiotic;
organooxygen heterocyclic antibiotic;
zwitterion		antiinfective agent;
antimetabolite;
antitubercular agent;
metabolite;
NMDA receptor agonist
2,3-dihydroxyquinoxaline
2,3-dihydroxyquinoxaline: fluorescent oxalic acid deriv.		3.0810
D-serine
[no description available]		3.0810D-alpha-amino acid;
serine zwitterion;
serine		Escherichia coli metabolite;
human metabolite;
NMDA receptor agonist
1-aminocyclobutanecarboxylic acid
1-aminocyclobutanecarboxylic acid: RN given refers to unlabeled cpd		3.0810L-alpha-amino acid
rpr 104632
RPR 104632: structure given in first source		3.0810
mdl29,951
[no description available]		3.0810
6,7-dichloro-3-hydroxy-2-quinoxalinecarboxylic acid
6,7-dichloro-3-hydroxy-2-quinoxalinecarboxylic acid: antagonist of N-methyl-D-aspartic acid and kainate receptors; structure given in first source		3.0810quinoxaline derivative
7-chloro-thiokynurenate
7-chlorothiokynurenic acid: glycine site antagonist of NMDA receptor		3.0810
fg 9041
FG 9041: structure given in first source		3.0810quinoxaline derivative
licostinel
licostinel: a glycine site NMDA receptor antagonist; structure given in first source		3.4920
gavestinel
[no description available]		1.9910
l 689560
[no description available]		3.0810quinolines
l 701324
L 701324: a glycine/NMDA receptor antagonist		3.4920quinolines
mdl 104653
3-phenyl-4-hydroxy-7-chloroquinolin-2(1H)-one: an NMDA/glycine site antagonist; structure given in first source		1.9910
ConditionIndicatedRelationship StrengthStudiesTrials
Congenital Zika Syndrome
[description not available]		02.2510
Disease Models, Animal
Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.		02.2510
Zika Virus Infection
A viral disease transmitted by the bite of AEDES mosquitoes infected with ZIKA VIRUS. Its mild DENGUE-like symptoms include fever, rash, headaches and ARTHRALGIA. The viral infection during pregnancy, in rare cases, is associated with congenital brain and ocular abnormalities, called Congenital Zika Syndrome, including MICROCEPHALY and may also lead to GUILLAIN-BARRE SYNDROME.		02.2510