2-heptyl-3-hydroxy-4-quinolone (PAMDB100069)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB100069
Identification
Name: 2-heptyl-3-hydroxy-4-quinolone
Description:

The Pseudomonas quinolone signal (PQS) is a quorum sensing molecule unique to Pseudomonas aeruginosa. This molecule is active when the density of bacterial cells reaches a quorum. PQS is an important signaling molecule that enhances the production of virulence factors by P. aeruginosa including the production of phenazines and elastases. PQS has also been reported to chelate ferric iron and induce vesicle formation at the membrane. PQS is produced from the hydroxylation of HHQ by mono-oxygenase PqsH.

Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:

• 2-Heptyl-3-hydroxy-4(1H)-chinolinon [German] [ACD/IUPAC Name]

• 2-Heptyl-3-hydroxy-4(1H)-quinoléinone [French] [ACD/IUPAC Name]

• 2-Heptyl-3-hydroxy-4(1H)-quinolinone [ACD/IUPAC Name]

• 2-heptyl-3-hydroxy-4-quinolone • 2-heptyl-3-hydroxyl-4(1H)-quinolone

• 2-Heptyl-3-hydroxyquinolin-4(1H)-one • 3,4-dihydroxy-2-heptylquinoline

• 4(1H)-Quinolinone, 2-heptyl-3-hydroxy- [ACD/Index Name]

• 10.1021/jm400830r

• 108985-27-9 [RN]

• 2-heptyl-3,4-dihydroxyquinoline

• 2-Heptyl-3-hydroxy-1H-quinolin-4-one

• 2-heptyl-3-hydroxy-4(1H)-quinolone

• 2-Heptyl-3-hydroxyl-4-chinolon

• 2-Heptyl-3-hydroxyl-4-quinolone

• 2-Heptyl-3-hydroxy-quinolone

• 521313-35-9 [RN]

• MFCD07437949 [MDL number]

• PQS

• Pseudomonas quinolone signal

Chemical Formula:

C16H21NO2

Average Molecular Weight: 259.3434
Monoisotopic Molecular Weight: 259.157227
InChI Key: CEIUIHOQDSVZJQ-UHFFFAOYSA-N
InChI:

InChI=1S/C16H21NO2/c1-2-3-4-5-6-11-14-16(19)15(18)12-9-7-8-10-13(12)17-14/h7-10,19H,2-6,11H2,1H3,(H,17,18)

CAS number: Not Available
IUPAC Name:

2-heptyl-3-hydroxy-1H-quinolin-4-one

Traditional IUPAC Name: Pseudomonas quinolone signal
SMILES:CCCCCCCc1c(c(=O)c2ccccc2[nH]1)O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as hydroxyquinolones. These are compounds containing a quinoline moiety bearing a hydroxyl group and a ketone. Quinoline or benzo[b]pyridine is a bicyclic compound that consists of benzene fused to a pyridine.
Kingdom Organic compounds
Super ClassOrganoheterocyclic compounds
Class Quinolines and derivatives
Sub ClassQuinolones and derivatives
Direct Parent Hydroxyquinolones
Alternative Parents
Substituents
  • Hydroxyquinolone
  • Dihydroquinolone
  • Hydroxyquinoline
  • Dihydroquinoline
  • Hydroxypyridine
  • Benzenoid
  • Pyridine
  • Heteroaromatic compound
  • Vinylogous amide
  • Azacycle
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular Framework Aromatic heteropolycyclic compounds
External Descriptors
  • quinolone (CHEBI:29472)
  • a tautomer (CPD-12838)
Physical Properties
State:

Solid, off white powder

Charge:0
Melting point:

Soluble in methanol

Experimental Properties: Not Available
Predicted Properties
PropertyValueSource

Water Solubility

 9.763 mg/L EPIsuite

logP

4.63

ChemAxon

logS

  

ALOGPS

pKa (Strongest Acidic)

  

ChemAxon

pKa (Strongest Basic)

  

ChemAxon

Physiological Charge

  

ChemAxon

Hydrogen Acceptor Count

  

ChemAxon

Hydrogen Donor Count

  

ChemAxon

Polar Surface Area

49.33 Å2

ChemAxon

Solvent  Accessible surface area

415.84

ChemAxon

Rotatable Bond Count

6

ChemAxon

Molar Refractivity

75.6 cm3

ACD/Labs

Polarizability

30 10-23cm3

ACD/Labs

Density

1.1 g/cm3

ACD/Labs

Boiling point

389°C AT 760 mmHg

ACD/Labs

Number of Rings

 

 

Bioavailability

Yes

ChemAxon

Rule of Five

Yes

ChemAxon

Ghose Filter

Yes

ChemAxon

Veber's Rule

Yes

ChemAxon

MDDR-like Rule

  

 

Lead likeness

No

ChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
HHQ + NADH + O2 → PQS + H2O + NAD+
Pathways:
    Spectra
    Spectra: Not Available
    References
    References:
    • Nguyen, A., Oglesby-Sherrouse, A. (2016). “Interactions between Pseudomonas aeruginosa and Staphylococcus aureus during co-cultivations and polymicrobial infections." Appl Microb and Biotech. Pubmed: 27236810
    Synthesis Reference: Not Available
    Material Safety Data Sheet (MSDS) Not Available
    External Links:
    Resource Link
    PubChem 2763159
    Chemspider 2043848