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2503-80-2 | 4-Quinolinol, 2-heptyl-
CAS No: 2503-80-2 Catalog No: AG002Q83 MDL No:
Product Description
Catalog Number:
AG002Q83
Chemical Name:
4-Quinolinol, 2-heptyl-
CAS Number:
2503-80-2
Molecular Formula:
C16H21NO
Molecular Weight:
243.3440
IUPAC Name:
2-heptyl-1H-quinolin-4-one
InChI:
InChI=1S/C16H21NO/c1-2-3-4-5-6-9-13-12-16(18)14-10-7-8-11-15(14)17-13/h7-8,10-12H,2-6,9H2,1H3,(H,17,18)
InChI Key:
UYRHHBXYXSYGHA-UHFFFAOYSA-N
SMILES:
CCCCCCCc1cc(O)c2c(n1)cccc2
Properties
Complexity:
308
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
243.162g/mol
Formal Charge:
0
Heavy Atom Count:
18
Hydrogen Bond Acceptor Count:
2
Hydrogen Bond Donor Count:
1
Isotope Atom Count:
0
Molecular Weight:
243.35g/mol
Monoisotopic Mass:
243.162g/mol
Rotatable Bond Count:
6
Topological Polar Surface Area:
29.1A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
4.9
Literature
| Title | Journal |
|---|---|
| Structure-function analysis of the C-3 position in analogues of microbial behavioural modulators HHQ and PQS. | Organic & biomolecular chemistry 20121128 |
| Repertoire of intensive care unit pneumonia microbiota. | PloS one 20120101 |
| Quorum sensing modulates colony morphology through alkyl quinolones in Pseudomonas aeruginosa. | BMC microbiology 20120101 |
| A bilayer-couple model of bacterial outer membrane vesicle biogenesis. | mBio 20120101 |
| Honey's Ability to Counter Bacterial Infections Arises from Both Bactericidal Compounds and QS Inhibition. | Frontiers in microbiology 20120101 |
| Pseudomonas aeruginosa overrides the virulence inducing effect of opioids when it senses an abundance of phosphate. | PloS one 20120101 |
| Social Behaviours under Anaerobic Conditions in Pseudomonas aeruginosa. | International journal of microbiology 20120101 |
| Quorum sensing signaling molecules produced by reference and emerging soft-rot bacteria (Dickeya and Pectobacterium spp.). | PloS one 20120101 |
| Quorum quenching revisited--from signal decays to signalling confusion. | Sensors (Basel, Switzerland) 20120101 |
| The Pseudomonas quinolone signal (PQS), and its precursor HHQ, modulate interspecies and interkingdom behaviour. | FEMS microbiology ecology 20110801 |
| A quorum sensing regulated small volatile molecule reduces acute virulence and promotes chronic infection phenotypes. | PLoS pathogens 20110801 |
| C-type natriuretic peptide modulates quorum sensing molecule and toxin production in Pseudomonas aeruginosa. | Microbiology (Reading, England) 20110701 |
| Quinolones: from antibiotics to autoinducers. | FEMS microbiology reviews 20110301 |
| Positive signature-tagged mutagenesis in Pseudomonas aeruginosa: tracking patho-adaptive mutations promoting airways chronic infection. | PLoS pathogens 20110201 |
| Detection of 2-alkyl-4-quinolones using biosensors. | Methods in molecular biology (Clifton, N.J.) 20110101 |
| Quantifying Pseudomonas aeruginosa quinolones and examining their interactions with lipids. | Methods in molecular biology (Clifton, N.J.) 20110101 |
| Simultaneous quantitative profiling of N-acyl-L-homoserine lactone and 2-alkyl-4(1H)-quinolone families of quorum-sensing signaling molecules using LC-MS/MS. | Analytical and bioanalytical chemistry 20110101 |
| Exploring the metabolic network of the epidemic pathogen Burkholderia cenocepacia J2315 via genome-scale reconstruction. | BMC systems biology 20110101 |
| Quorum sensing and Bacterial Pathogenicity: From Molecules to Disease. | Journal of laboratory physicians 20110101 |
| MexEF-OprN efflux pump exports the Pseudomonas quinolone signal (PQS) precursor HHQ (4-hydroxy-2-heptylquinoline). | PloS one 20110101 |
| Phenotypic and genome-wide analysis of an antibiotic-resistant small colony variant (SCV) of Pseudomonas aeruginosa. | PloS one 20110101 |
| Candida albicans-produced farnesol stimulates Pseudomonas quinolone signal production in LasR-defective Pseudomonas aeruginosa strains. | Microbiology (Reading, England) 20101001 |
| Oxygen levels rapidly modulate Pseudomonas aeruginosa social behaviours via substrate limitation of PqsH. | Molecular microbiology 20100901 |
| Transcriptomic analysis reveals a global alkyl-quinolone-independent regulatory role for PqsE in facilitating the environmental adaptation of Pseudomonas aeruginosa to plant and animal hosts. | Environmental microbiology 20100601 |
| HHQ and PQS, two Pseudomonas aeruginosa quorum-sensing molecules, down-regulate the innate immune responses through the nuclear factor-kappaB pathway. | Immunology 20100401 |
| Homeostatic interplay between bacterial cell-cell signaling and iron in virulence. | PLoS pathogens 20100301 |
| Nutrient availability as a mechanism for selection of antibiotic tolerant Pseudomonas aeruginosa within the CF airway. | PLoS pathogens 20100101 |
| Staphylococcus aureus sigma B-dependent emergence of small-colony variants and biofilm production following exposure to Pseudomonas aeruginosa 4-hydroxy-2-heptylquinoline-N-oxide. | BMC microbiology 20100101 |
| Dioxygenase-mediated quenching of quinolone-dependent quorum sensing in Pseudomonas aeruginosa. | Chemistry & biology 20091224 |
| Subinhibitory concentrations of the cationic antimicrobial peptide colistin induce the pseudomonas quinolone signal in Pseudomonas aeruginosa. | Microbiology (Reading, England) 20090901 |
| Effects of osmotic stress on rhamnolipid synthesis and time-course production of cell-to-cell signal molecules by Pseudomonas aeruginosa. | The open microbiology journal 20090101 |
| Burkholderia thailandensis harbors two identical rhl gene clusters responsible for the biosynthesis of rhamnolipids. | BMC microbiology 20090101 |
| Quorum sensing by 2-alkyl-4-quinolones in Pseudomonas aeruginosa and other bacterial species. | Molecular bioSystems 20080901 |
| The pseudomonas quinolone signal (PQS) balances life and death in Pseudomonas aeruginosa populations. | PLoS pathogens 20080901 |
| Interaction of quorum signals with outer membrane lipids: insights into prokaryotic membrane vesicle formation. | Molecular microbiology 20080701 |
| Multiple roles of Pseudomonas aeruginosa TBCF10839 PilY1 in motility, transport and infection. | Molecular microbiology 20080201 |
| Use of the lambda Red recombinase system to rapidly generate mutants in Pseudomonas aeruginosa. | BMC molecular biology 20080101 |
| Fitness of isogenic colony morphology variants of Pseudomonas aeruginosa in murine airway infection. | PloS one 20080101 |
| Bioactive compound synthetic capacity and ecological significance of marine bacterial genus pseudoalteromonas. | Marine drugs 20071201 |
| A dual biosensor for 2-alkyl-4-quinolone quorum-sensing signal molecules. | Environmental microbiology 20071101 |
| Inhibitors of pathogen intercellular signals as selective anti-infective compounds. | PLoS pathogens 20070901 |
| Iron- and 4-hydroxy-2-alkylquinoline-containing periplasmic inclusion bodies of Pseudomonas aeruginosa: a chemical analysis. | Bioorganic chemistry 20070401 |
| Growth phenotypes of Pseudomonas aeruginosa lasR mutants adapted to the airways of cystic fibrosis patients. | Molecular microbiology 20070401 |
| Dynorphin activates quorum sensing quinolone signaling in Pseudomonas aeruginosa. | PLoS pathogens 20070301 |
| The Pseudomonas aeruginosa 4-quinolone signal molecules HHQ and PQS play multifunctional roles in quorum sensing and iron entrapment. | Chemistry & biology 20070101 |
| Biosensor-based assays for PQS, HHQ and related 2-alkyl-4-quinolone quorum sensing signal molecules. | Nature protocols 20070101 |
| MvfR, a key Pseudomonas aeruginosa pathogenicity LTTR-class regulatory protein, has dual ligands. | Molecular microbiology 20061201 |
| Functional genetic analysis reveals a 2-Alkyl-4-quinolone signaling system in the human pathogen Burkholderia pseudomallei and related bacteria. | Chemistry & biology 20060701 |
| 4-quinolone signalling in Pseudomonas aeruginosa: old molecules, new perspectives. | International journal of medical microbiology : IJMM 20060401 |
| Purification and characterization of succinate:menaquinone oxidoreductase from Corynebacterium glutamicum. | Archives of microbiology 20050801 |
| Succinate:quinone oxidoreductase in the bacteria Paracoccus denitrificans and Bacillus subtilis. | Biochimica et biophysica acta 20020117 |
| 4-hydroxy-2-nonylquinoline: a novel iron chelator isolated from a bacterial cell membrane. | Bioorganic chemistry 20011201 |
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