Page last updated: 2024-12-09

2-heptyl-3-hydroxy-4-quinolone

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

Description

2-heptyl-3-hydroxy-4-quinolone: structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

2-heptyl-3-hydroxy-4-quinolone : A quinolone consisting of quinolin-4(1H)-one carrying a heptyl substituent at position 2 and a hydroxy group at position 3. [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]

Cross-References

ID SourceID
PubMed CID2763159
CHEMBL ID2426244
CHEBI ID29472
SCHEMBL ID130919
MeSH IDM0362594

Synonyms (27)

Synonym
2-heptyl-3-hydroxy-4-quinolone
2-heptyl-3-hydroxy-4(1h)-quinolone
2-heptyl-3-hydroxy-quinolone
2-heptyl-3-hydroxy-1h-quinolin-4-one
pqs ,
pseudomonas quinolone signal
2-heptyl-3-hydroxy-4(1h)-quinolinone
CHEBI:29472 ,
FT-0647383
AKOS015897030
chembl2426244 ,
bdbm50440134
SCHEMBL130919
DTXSID00376772
2-heptylquinoline-3,4-diol
J-002218
2-heptyl-3-hydroxy-4(1h)-quinolone, >=96.0% (hplc)
4(1h)-quinolinone, 2-heptyl-3-hydroxy-
2-heptyl-3-hydroxyl-4-quinolone
mfcd07437949
3,4-dihydroxy-2-heptylquinoline
FT-0761545
F16823
Q27110090
JWW ,
SB71720
PD096092
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
signalling moleculeA molecular messenger in which the molecule is specifically involved in transmitting information between cells. Such molecules are released from the cell sending the signal, cross over the gap between cells by diffusion, and interact with specific receptors in another cell, triggering a response in that cell by activating a series of enzyme controlled reactions which lead to changes inside the cell.
[role 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]

Drug Classes (1)

ClassDescription
quinolone
[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]

Pathways (2)

PathwayProteinsCompounds
2-heptyl-3-hydroxy-4(1H)-quinolone biosynthesis319
superpathway of quinolone and alkylquinolone biosynthesis724

Protein Targets (1)

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
LysR family transcriptional regulator Pseudomonas aeruginosaKd0.21000.21000.93671.8000AID770032
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (30)

Assay IDTitleYearJournalArticle
AID1752221Inhibition of glutamate-induced apoptosis in mouse HT-22 cells assessed as necrotic cells at 0.2 uM pretreated with glutamate for 2 hrs followed by incubation with compound for 8 hrs by Annexin-V FITC and propidium iodide staining based flow cytometric an2021Bioorganic & medicinal chemistry letters, 10-01, Volume: 49Neuroprotective effects of 2-heptyl-3-hydroxy-4-quinolone in HT22 mouse hippocampal neuronal cells.
AID1752214Inhibition of glutamate-induced ERK activation in mouse HT-22 cells assessed as reduction in phosphorylated ERK protein level at 1 to 10 uM in presence of glutamate by Western blot analysis2021Bioorganic & medicinal chemistry letters, 10-01, Volume: 49Neuroprotective effects of 2-heptyl-3-hydroxy-4-quinolone in HT22 mouse hippocampal neuronal cells.
AID1752222Inhibition of glutamate-induced apoptosis in mouse HT-22 cells assessed as early apoptotic cells at 1.85 uM pretreated with glutamate for 2 hrs followed by incubation with compound for 8 hrs by Annexin-V FITC and propidium iodide staining based flow cytom2021Bioorganic & medicinal chemistry letters, 10-01, Volume: 49Neuroprotective effects of 2-heptyl-3-hydroxy-4-quinolone in HT22 mouse hippocampal neuronal cells.
AID1752212Inhibition of glutamate-induced Ca2+ influx in mouse HT-22 cells assessed as reduction in intracellular Ca2+ concentration in presence of glutamate by Fluo3-AM staining based fluorescence microscopic method2021Bioorganic & medicinal chemistry letters, 10-01, Volume: 49Neuroprotective effects of 2-heptyl-3-hydroxy-4-quinolone in HT22 mouse hippocampal neuronal cells.
AID1752218Inhibition of glutamate-induced AIF nuclear translocation in mouse HT-22 cells assessed as decrease in translocation of AIF from mitochondria to nucleus at 1 to 10 uM in presence of glutamate by Western blot analysis2021Bioorganic & medicinal chemistry letters, 10-01, Volume: 49Neuroprotective effects of 2-heptyl-3-hydroxy-4-quinolone in HT22 mouse hippocampal neuronal cells.
AID1752226Inhibition of glutamate-induced apoptosis in mouse HT-22 cells assessed as viable cells at 0.2 uM pretreated with glutamate for 2 hrs followed by incubation with compound for 8 hrs by Annexin-V FITC and propidium iodide staining based flow cytometric anal2021Bioorganic & medicinal chemistry letters, 10-01, Volume: 49Neuroprotective effects of 2-heptyl-3-hydroxy-4-quinolone in HT22 mouse hippocampal neuronal cells.
AID1453673Inhibition of NF-kappaB (unknown origin) expressed in human L428 cells after 2 hrs by luciferase reporter gene assay2017Bioorganic & medicinal chemistry letters, 07-01, Volume: 27, Issue:13
Quorum sensing modulators exhibit cytotoxicity in Hodgkin's lymphoma cells and interfere with NF-κB signaling.
AID1752215Inhibition of glutamate-induced p38 MAPK activation in mouse HT-22 cells assessed as reduction in phosphorylated p38 MAPK protein level at 1 to 10 uM in presence of glutamate by Western blot analysis2021Bioorganic & medicinal chemistry letters, 10-01, Volume: 49Neuroprotective effects of 2-heptyl-3-hydroxy-4-quinolone in HT22 mouse hippocampal neuronal cells.
AID1752233Inhibition of glutamate-induced AIF nuclear translocation in mouse HT-22 cells assessed as decrease in translocation of AIF from mitochondria to nucleus in presence of glutamate by immunostaining analysis2021Bioorganic & medicinal chemistry letters, 10-01, Volume: 49Neuroprotective effects of 2-heptyl-3-hydroxy-4-quinolone in HT22 mouse hippocampal neuronal cells.
AID1752216Inhibition of glutamate-induced apoptosis in mouse HT-22 cells assessed as reduction in Bax protein level at 1 to 10 uM incubated for 10 hrs in presence of glutamate by Western blot analysis2021Bioorganic & medicinal chemistry letters, 10-01, Volume: 49Neuroprotective effects of 2-heptyl-3-hydroxy-4-quinolone in HT22 mouse hippocampal neuronal cells.
AID1752213Inhibition of glutamate-induced JNK activation in mouse HT-22 cells assessed as reduction in phosphorylated JNK protein level at 1 to 10 uM in presence of glutamate by Western blot analysis2021Bioorganic & medicinal chemistry letters, 10-01, Volume: 49Neuroprotective effects of 2-heptyl-3-hydroxy-4-quinolone in HT22 mouse hippocampal neuronal cells.
AID1752230Cytoprotective activity against glutamate-induced cytotoxicity in rat RGC-5 cells assessed as reduction in cell death2021Bioorganic & medicinal chemistry letters, 10-01, Volume: 49Neuroprotective effects of 2-heptyl-3-hydroxy-4-quinolone in HT22 mouse hippocampal neuronal cells.
AID1752231Antioxidant activity assessed as DPPH radical scavenging activity2021Bioorganic & medicinal chemistry letters, 10-01, Volume: 49Neuroprotective effects of 2-heptyl-3-hydroxy-4-quinolone in HT22 mouse hippocampal neuronal cells.
AID1752211Inhibition of glutamate-induced oxidative stress in mouse HT-22 cells assessed as reduction in intracellular ROS accumulation at 0.2 to 3.6 uM in presence of glutamate by DCF-DA staining based fluorescence microscopic analysis2021Bioorganic & medicinal chemistry letters, 10-01, Volume: 49Neuroprotective effects of 2-heptyl-3-hydroxy-4-quinolone in HT22 mouse hippocampal neuronal cells.
AID1551081Agonist activity at Pseudomonas aeruginosa pqsA delta frame deletion mutant2019European journal of medicinal chemistry, Jun-15, Volume: 172Anti-PqsR compounds as next-generation antibacterial agents against Pseudomonas aeruginosa: A review.
AID1752232Inhibition of glutamate-induced Ca2+ influx in mouse HT-22 cells assessed as reduction in intracellular Ca2+ concentration at 0.6 to 1.8 uM in presence of glutamate by Fluo3-AM staining based fluorescence microscopic method relative to control2021Bioorganic & medicinal chemistry letters, 10-01, Volume: 49Neuroprotective effects of 2-heptyl-3-hydroxy-4-quinolone in HT22 mouse hippocampal neuronal cells.
AID1752210Inhibition of glutamate-induced oxidative stress in mouse HT-22 cells assessed as reduction in intracellular ROS accumulation at 0.2 to 1.8 uM in presence of glutamate by FACS analysis2021Bioorganic & medicinal chemistry letters, 10-01, Volume: 49Neuroprotective effects of 2-heptyl-3-hydroxy-4-quinolone in HT22 mouse hippocampal neuronal cells.
AID1752219Inhibition of glutamate-induced apoptosis in mouse HT-22 cells assessed as early apoptotic cells at 0.2 uM pretreated with glutamate for 2 hrs followed by incubation with compound for 8 hrs by Annexin-V FITC and propidium iodide staining based flow cytome2021Bioorganic & medicinal chemistry letters, 10-01, Volume: 49Neuroprotective effects of 2-heptyl-3-hydroxy-4-quinolone in HT22 mouse hippocampal neuronal cells.
AID770027Agonist activity at Pseudomonas aeruginosa PA14 PqsR expressed in Eschericia coli DH5-alpha at 50 nM by beta-galactosidase reporter gene assay relative to control2013Journal of medicinal chemistry, Sep-12, Volume: 56, Issue:17
Discovery and biophysical characterization of 2-amino-oxadiazoles as novel antagonists of PqsR, an important regulator of Pseudomonas aeruginosa virulence.
AID1752229Neuroprotective activity against glutamate-induced cytotoxicity in mouse HT-22 cells assessed as reduction in cell death pretreated with glutamate followed by incubation with compound for 8 hrs and measured at 16 hrs post-glutamate treatment2021Bioorganic & medicinal chemistry letters, 10-01, Volume: 49Neuroprotective effects of 2-heptyl-3-hydroxy-4-quinolone in HT22 mouse hippocampal neuronal cells.
AID1752227Neuroprotective activity against glutamate-induced cytotoxicity in mouse HT-22 cells assessed as reduction in cell death and morphological changes at 0.6 to 1.8 uM incubated for 12 hrs in presence of glutamate by phase contrast microscopic analysis2021Bioorganic & medicinal chemistry letters, 10-01, Volume: 49Neuroprotective effects of 2-heptyl-3-hydroxy-4-quinolone in HT22 mouse hippocampal neuronal cells.
AID1752228Neuroprotective activity against glutamate-induced cytotoxicity in mouse HT-22 cells assessed as reduction in cell death pretreated with glutamate followed by incubation with compound for 6 hrs and measured at 16 hrs post-glutamate treatment2021Bioorganic & medicinal chemistry letters, 10-01, Volume: 49Neuroprotective effects of 2-heptyl-3-hydroxy-4-quinolone in HT22 mouse hippocampal neuronal cells.
AID1752209Neuroprotective activity against glutamate-induced cytotoxicity in mouse HT-22 cells assessed as increase in cell viability at 1.85 to 5.5 uM in presence of glutamate by calcein-AM dye/propidium iodide staining based microscopic analysis2021Bioorganic & medicinal chemistry letters, 10-01, Volume: 49Neuroprotective effects of 2-heptyl-3-hydroxy-4-quinolone in HT22 mouse hippocampal neuronal cells.
AID1752223Inhibition of glutamate-induced apoptosis in mouse HT-22 cells assessed as late apoptotic cells at 1.85 uM pretreated with glutamate for 2 hrs followed by incubation with compound for 8 hrs by Annexin-V FITC and propidium iodide staining based flow cytome2021Bioorganic & medicinal chemistry letters, 10-01, Volume: 49Neuroprotective effects of 2-heptyl-3-hydroxy-4-quinolone in HT22 mouse hippocampal neuronal cells.
AID1752220Inhibition of of glutamate-induced apoptosis in mouse HT-22 cells assessed as late apoptotic cells at 0.2 uM pretreated with glutamate for 2 hrs followed by incubation with compound for 8 hrs by Annexin-V FITC and propidium iodide staining based flow cyto2021Bioorganic & medicinal chemistry letters, 10-01, Volume: 49Neuroprotective effects of 2-heptyl-3-hydroxy-4-quinolone in HT22 mouse hippocampal neuronal cells.
AID1752217Inhibition of glutamate-induced apoptosis in mouse HT-22 cells assessed as increase in Bcl2 protein level at 1 to 10 uM incubated for 10 hrs in presence of glutamate by Western blot analysis2021Bioorganic & medicinal chemistry letters, 10-01, Volume: 49Neuroprotective effects of 2-heptyl-3-hydroxy-4-quinolone in HT22 mouse hippocampal neuronal cells.
AID1752208Neuroprotective activity against glutamate-induced cytotoxicity in mouse HT-22 cells assessed as increase in cell viability at 0.6 uM in presence of glutamate by calcein-AM dye/propidium iodide staining based microscopic analysis2021Bioorganic & medicinal chemistry letters, 10-01, Volume: 49Neuroprotective effects of 2-heptyl-3-hydroxy-4-quinolone in HT22 mouse hippocampal neuronal cells.
AID1752225Inhibition of glutamate-induced apoptosis in mouse HT-22 cells assessed as viable cells at 1.85 uM pretreated with glutamate for 2 hrs followed by incubation with compound for 8 hrs by Annexin-V FITC and propidium iodide staining based flow cytometric ana2021Bioorganic & medicinal chemistry letters, 10-01, Volume: 49Neuroprotective effects of 2-heptyl-3-hydroxy-4-quinolone in HT22 mouse hippocampal neuronal cells.
AID1752224Inhibition of glutamate-induced apoptosis in mouse HT-22 cells assessed as necrotic cells at 1.85 uM pretreated with glutamate for 2 hrs followed by incubation with compound for 8 hrs by Annexin-V FITC and propidium iodide staining based flow cytometric a2021Bioorganic & medicinal chemistry letters, 10-01, Volume: 49Neuroprotective effects of 2-heptyl-3-hydroxy-4-quinolone in HT22 mouse hippocampal neuronal cells.
AID770032Binding affinity to Pseudomonas aeruginosa PA14 biotinylated His6SUMO-tagged PqsR expressed in Eschericia coli BL21 (DE3) by surface plasmon resonance spectroscopic analysis2013Journal of medicinal chemistry, Sep-12, Volume: 56, Issue:17
Discovery and biophysical characterization of 2-amino-oxadiazoles as novel antagonists of PqsR, an important regulator of Pseudomonas aeruginosa virulence.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (135)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's41 (30.37)29.6817
2010's74 (54.81)24.3611
2020's20 (14.81)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 28.43

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 moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index28.43 (24.57)
Research Supply Index4.91 (2.92)
Research Growth Index6.72 (4.65)
Search Engine Demand Index22.26 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (28.43)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews8 (5.93%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other127 (94.07%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]