Compounds > l 689560
Page last updated: 2024-12-11

l 689560

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 CID6604749
CHEMBL ID287327
CHEBI ID93308
SCHEMBL ID499151
MeSH IDM0201393

Synonyms (33)

Synonym
BRD-K74284736-001-01-5
tocris-0742
NCGC00024761-01
BIOMOL-NT_000205
BPBIO1_001262
NCGC00024761-02
l-689,560
l-689560
CHEMBL287327 ,
bdbm50005075
5,7-dichloro-4-(3-phenyl-ureido)-1,2,3,4-tetrahydro-quinoline-2-carboxylic acid
(2r,4s)-5,7-dichloro-4-(3-phenyl-ureido)-1,2,3,4-tetrahydro-quinoline-2-carboxylic acid
(2r,4s)-5,7-dichloro-4-(phenylcarbamoylamino)-1,2,3,4-tetrahydroquinoline-2-carboxylic acid
139051-78-8
SCHEMBL499151
trans-2-carboxy-5,7-dichloro-4-phenylaminocarbonylamino-1,2,3,4-tetrahydroquinoline
AKOS024458626
mfcd00672670
trans-2-carboxy-5,7-dichloro-4-phenylaminocarbonyl amino-1,2,3,4-tetrahydroquinoline
sr-01000597688
SR-01000597688-1
CHEBI:93308
trans-2-carboxy-5,7-dichloro-4-pheny-laminocarbonyl amino-1,2,3,4-tetrahydroquinoline
(2r,4s)-5,7-dichloro-4-(3-phenylureido)-1,2,3,4-tetrahydroquinoline-2-carboxylic acid
Q27165020
(2r,4s)-4-[[anilino(oxo)methyl]amino]-5,7-dichloro-1,2,3,4-tetrahydroquinoline-2-carboxylic acid
HMS3675F15
HY-101178
(2r,4s)-5,7-dichloro-4-[(phenylcarbamoyl)amino]-1,2,3,4-tetrahydroquinoline-2-carboxylic acid
QGM ,
HMS3411F15
CS-0020947
(2r,4s)-5,7-dichloro-4-(3-phenylureido)-1,2,3,4-tetrahydroquinoline-2-carboxylicacid
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
quinolinesA class of aromatic heterocyclic compounds each of which contains a benzene ring ortho fused to carbons 2 and 3 of a pyridine ring.
[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 (28)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
USP1 protein, partialHomo sapiens (human)Potency44.66840.031637.5844354.8130AID504865
cytochrome P450 2D6 isoform 1Homo sapiens (human)Potency12.58930.00207.533739.8107AID891
cytochrome P450 2C19 precursorHomo sapiens (human)Potency25.11890.00255.840031.6228AID899
vitamin D3 receptor isoform VDRAHomo sapiens (human)Potency59.66490.354828.065989.1251AID504847
cytochrome P450 3A4 isoform 1Homo sapiens (human)Potency25.11890.031610.279239.8107AID884; AID885
Gamma-aminobutyric acid receptor subunit piRattus norvegicus (Norway rat)Potency25.11891.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit beta-1Rattus norvegicus (Norway rat)Potency25.11891.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit deltaRattus norvegicus (Norway rat)Potency25.11891.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit gamma-2Rattus norvegicus (Norway rat)Potency25.11891.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-5Rattus norvegicus (Norway rat)Potency25.11891.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-3Rattus norvegicus (Norway rat)Potency25.11891.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit gamma-1Rattus norvegicus (Norway rat)Potency25.11891.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-2Rattus norvegicus (Norway rat)Potency25.11891.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-4Rattus norvegicus (Norway rat)Potency25.11891.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit gamma-3Rattus norvegicus (Norway rat)Potency25.11891.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-6Rattus norvegicus (Norway rat)Potency25.11891.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-1Rattus norvegicus (Norway rat)Potency25.11891.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit beta-3Rattus norvegicus (Norway rat)Potency25.11891.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit beta-2Rattus norvegicus (Norway rat)Potency25.11891.000012.224831.6228AID885
GABA theta subunitRattus norvegicus (Norway rat)Potency25.11891.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit epsilonRattus norvegicus (Norway rat)Potency25.11891.000012.224831.6228AID885
[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)0.00640.00071.600310.0000AID143068; AID143162; AID145260
Glutamate receptor ionotropic, NMDA 1 Rattus norvegicus (Norway rat)Ki0.00200.00030.86666.6900AID143084
Glutamate receptor ionotropic, NMDA 2A Rattus norvegicus (Norway rat)IC50 (µMol)0.00780.00071.630610.0000AID145260
Glutamate receptor ionotropic, NMDA 2A Rattus norvegicus (Norway rat)Ki0.00200.00030.68056.6900AID143084
Glutamate receptor ionotropic, NMDA 2BRattus norvegicus (Norway rat)IC50 (µMol)0.00780.00061.525710.0000AID145260
Glutamate receptor ionotropic, NMDA 2BRattus norvegicus (Norway rat)Ki0.00200.00030.70716.6900AID143084
Glutamate receptor ionotropic, NMDA 2CRattus norvegicus (Norway rat)IC50 (µMol)0.00780.00071.747210.0000AID145260
Glutamate receptor ionotropic, NMDA 2CRattus norvegicus (Norway rat)Ki0.00200.00030.81966.6900AID143084
Glutamate receptor ionotropic, NMDA 2DRattus norvegicus (Norway rat)IC50 (µMol)0.00780.00071.741110.0000AID145260
Glutamate receptor ionotropic, NMDA 2DRattus norvegicus (Norway rat)Ki0.00200.00030.70726.6900AID143084
Glutamate receptor ionotropic, NMDA 3BRattus norvegicus (Norway rat)IC50 (µMol)0.00780.00071.741110.0000AID145260
Glutamate receptor ionotropic, NMDA 3BRattus norvegicus (Norway rat)Ki0.00200.00030.70726.6900AID143084
Glutamate receptor ionotropic, NMDA 3ARattus norvegicus (Norway rat)IC50 (µMol)0.00780.00071.741110.0000AID145260
Glutamate receptor ionotropic, NMDA 3ARattus norvegicus (Norway rat)Ki0.00200.00030.70726.6900AID143084
[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)Kb0.13000.00592.09697.0000AID143250; AID186996
Glutamate receptor ionotropic, NMDA 2A Rattus norvegicus (Norway rat)Kb0.13000.00592.41137.0000AID143250; AID186996
Glutamate receptor ionotropic, NMDA 2BRattus norvegicus (Norway rat)Kb0.13000.00592.41137.0000AID143250; AID186996
Glutamate receptor ionotropic, NMDA 2CRattus norvegicus (Norway rat)Kb0.13000.00592.41137.0000AID143250; AID186996
Glutamate receptor ionotropic, NMDA 2DRattus norvegicus (Norway rat)Kb0.13000.00592.41137.0000AID143250; AID186996
Glutamate receptor ionotropic, NMDA 3BRattus norvegicus (Norway rat)Kb0.13000.00592.41137.0000AID143250; AID186996
Glutamate receptor ionotropic, NMDA 3ARattus norvegicus (Norway rat)Kb0.13000.00592.41137.0000AID143250; AID186996
[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 (15)

Assay IDTitleYearJournalArticle
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.
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.
AID112660In vivo antagonist activity against seizures elicited by audiogenic administered icv in mice1994Journal of medicinal chemistry, Nov-25, Volume: 37, Issue:24
The glycine site on the NMDA receptor: structure-activity relationships and therapeutic potential.
AID143610Inhibition of binding of [3H]glycine to N-methyl-D-aspartate glutamate receptor 1 from crude synaptic membranes prepared from adult rat cerebral cortex.1998Journal of medicinal chemistry, Mar-12, Volume: 41, Issue:6
(E)-3-(2-(N-phenylcarbamoyl)vinyl)pyrrole-2-carboxylic acid derivatives. A novel class of glycine site antagonists.
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.
AID143771Inhibition of [3H]glycine to glycine binding site, associated with the N-methyl-D-aspartate glutamate receptor 1 in crude synaptic membranes prepared from adult rat cerebral cortex.1997Journal of medicinal chemistry, Mar-14, Volume: 40, Issue:6
Substituted indole-2-carboxylates as in vivo potent antagonists acting as the strychnine-insensitive glycine binding site.
AID143162Inhibition of [3H]- glycine binding to NMDA receptor from rat cortical membranes.1992Journal of medicinal chemistry, May-29, Volume: 35, Issue:11
4-Amido-2-carboxytetrahydroquinolines. Structure-activity relationships for antagonism at the glycine site of the NMDA receptor.
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.
AID143084Affinity for the glycine binding site of NMDA receptor by inhibition of [3H]5,7-dichlorokynurenic acid ([3H]DCKA) binding to rat brain synaptic membrane1994Journal of medicinal chemistry, Nov-11, Volume: 37, Issue:23
Tricyclic quinoxalinediones: 5,6-dihydro-1H-pyrrolo[1,2,3-de] quinoxaline-2,3-diones and 6,7-dihydro-1H,5H-pyrido[1,2,3-de] quinoxaline-2,3-diones as potent antagonists for the glycine binding site of the NMDA receptor.
AID131549Protection from audiogenic seizure in the DBA/2 mouse 30 min after intraperitoneal administration1994Journal of medicinal chemistry, May-13, Volume: 37, Issue:10
3'-(Arylmethyl)- and 3'-(aryloxy)-3-phenyl-4-hydroxyquinolin-2(1H)-ones: orally active antagonists of the glycine site on the NMDA receptor.
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.
AID114334Effective dose to inhibit convulsions induced by NMDA in mice, when administered intravenous route.1997Journal of medicinal chemistry, Mar-14, Volume: 40, Issue:6
Substituted indole-2-carboxylates as in vivo potent antagonists acting as the strychnine-insensitive glycine binding site.
AID186995Blockade of NMDA-induced depolarizations on rat cortical slices1994Journal of medicinal chemistry, May-13, Volume: 37, Issue:10
3'-(Arylmethyl)- and 3'-(aryloxy)-3-phenyl-4-hydroxyquinolin-2(1H)-ones: orally active antagonists of the glycine site on the NMDA receptor.
AID186996Compound was evaluated for antagonism of depolarizations due to NMDA in a rat cortical slice preparation1992Journal of medicinal chemistry, May-29, Volume: 35, Issue:11
4-Amido-2-carboxytetrahydroquinolines. Structure-activity relationships for antagonism at the glycine site of the NMDA receptor.
AID143068Inhibition of the binding of [3H]L-689,560 ([3H]-4) to the strychnine-insensitive glycine site on rat brain membranes1994Journal of medicinal chemistry, May-13, Volume: 37, Issue:10
3'-(Arylmethyl)- and 3'-(aryloxy)-3-phenyl-4-hydroxyquinolin-2(1H)-ones: orally active antagonists of the glycine site on the NMDA receptor.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (8)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's6 (75.00)18.2507
2000's0 (0.00)29.6817
2010's0 (0.00)24.3611
2020's2 (25.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.47

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 Index12.47 (24.57)
Research Supply Index2.20 (2.92)
Research Growth Index4.66 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.47)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (12.50%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other7 (87.50%)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]		3.4920alpha-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]		3.4920quinoxaline 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.		3.0810organochlorine compound;
quinolinemonocarboxylic acid		neuroprotective agent;
NMDA receptor antagonist
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
4-trans-2-carboxy-5,7-dichloro-4-phenylaminocarbonylamino-1,2,3,4-tetrahydroquinoline
4-trans-2-carboxy-5,7-dichloro-4-phenylaminocarbonylamino-1,2,3,4-tetrahydroquinoline: structure given in first source; selective antagonist for the glycine site on the N-methyl-D-aspartate (NMDA) receptor		1.9810
rpr 104632
RPR 104632: structure given in first source		3.0810
mdl29,951
[no description available]		3.7830
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 701324
L 701324: a glycine/NMDA receptor antagonist		440quinolines
7-chloro-3-[cyclopropyl(oxo)methyl]-4-hydroxy-1H-quinolin-2-one
[no description available]		3.0810hydroxyquinoline;
quinolone
mdl 104653
3-phenyl-4-hydroxy-7-chloroquinolin-2(1H)-one: an NMDA/glycine site antagonist; structure given in first source		1.9810
ConditionIndicatedRelationship StrengthStudiesTrials
Absence Seizure
[description not available]		01.9910
Seizures
Clinical or subclinical disturbances of cortical function due to a sudden, abnormal, excessive, and disorganized discharge of brain cells. Clinical manifestations include abnormal motor, sensory and psychic phenomena. Recurrent seizures are usually referred to as EPILEPSY or seizure disorder.		01.9910
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