P. aeruginosa Metabolome Database: 2-Heptyl-4-quinolinol 1-oxide (PAMDB100075)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes Transporters

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 11:54:54 AM

Metabolite ID

PAMDB100075

Identification

Name:

2-Heptyl-4-quinolinol 1-oxide

Description:

2-Heptyl-4-quinolinol 1 –oxide (HQNO) is an N-oxide ubiquinone analog that inhibits activity of cytochrome b1 complex, thus inhibiting respiration of Gram-Positive bacteria such as Staphylococcus aureus. HQNO has been shown to induce small colony variants (SCVs) and fermentative metabolism is S. aureus. HQNO is produced from the activity of the PqsL mono-oxygenase protein in Pseudomonas aeruginosa.

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

• 1-Oxyde de 2-heptyl-4-quinoléinol [French] [ACD/IUPAC Name]

• 2-Heptyl-4-chinolinol-1-oxid [German] [ACD/IUPAC Name]

• 2-Heptyl-4-quinolinol 1-oxide [ACD/IUPAC Name]

• 2-Heptylquinolin-4-ol 1-oxide

• 341-88-8 [RN] • 4-Quinolinol, 2-heptyl-, 1-oxide [ACD/Index Name]

• 1466419 [Beilstein]

• 2-(n-heptyl)-4-hydroxyquinoline N-oxide

• 2-HEPTYL-4-HYDROXY QUINOLINE N-OXIDE

• 2-heptyl-4-hydroxyquinolin-1-ium-1-olate

• 2-heptyl-4-hydroxyquinoline N-oxide

• 2-Heptyl-4-hydroxyquinoline oxide

• 2-Heptyl-4-hydroxyquinoline-1-oxide

• 2-Heptyl-4-Hydroxyquinoline-N-Oxide

• 2-Heptylquinolin-4-ol, 1-oxide

• HOQNO

• HQNO

• PYO 11

• UNII-1FU5S5CG6A

Chemical Formula:

C₁₆H₂₁NO₂

Average Molecular Weight:

259.343

Monoisotopic Molecular Weight:

259.157227

InChI Key:

NZPACTGCRWDXCJ-UHFFFAOYSA-N

InChI:

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

CAS number:

Not Available

IUPAC Name:

2-heptyl-4-hydroxyquinolin-1-ium-1-olate

Traditional IUPAC Name:

hoqno, HQNO

SMILES:

CCCCCCCC1=CC(O)=C2C=CC=CC2=[N+]1[O-]

Chemical Taxonomy

Taxonomy Description

This compound belongs to the class of organic compounds known as 4-hydroxy-2-alkylquinolines. These are organic compounds containing a quinoline moiety with a hydroxyl group attached to the C4 atom, and an alkyl chain attached to the C2 atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

4-hydroxy-2-alkylquinolines

Direct Parent

4-hydroxy-2-alkylquinolines

Alternative Parents

Substituents

4-hydroxy-2-alkylquinoline
Hydroxyquinoline
Hydroxypyridine
Pyridine
Pyridinium
Benzenoid
Heteroaromatic compound
Azacycle
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

monohydroxyquinoline, quinoline N-oxide (CHEBI:28362)

Physical Properties

State:

Solid, off white powder

Charge:

Melting point:

Not Available

Experimental Properties:

Not Available

Predicted Properties

Property	Value	Source
Water Solubility	2.103 mg/L	EPIsuite
logP	3.83	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	47.17 Å2	ChemAxon
Solvent Accessible surface area	431.86	ChemAxon
Rotatable Bond Count	6	ChemAxon
Molar Refractivity	76.7 cm3	ACD/Labs
Polarizability	30.4 10-24cm3	ACD/Labs
Density	1.1 g/cm3	ACD/Labs
Boiling point	445.8°C at 760 mmHg
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule		ChemAxon
Lead likeness	Yes	ChemAxon
Muegge Filter	Yes	ChemAxon

Biological Properties

Cellular Locations:

Not Available

Reactions:

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

Links

External Links:

Resource	Link
PubChem	1561
Chemspider	10649239

2-Heptyl-4-quinolinol 1-oxide (PAMDB100075)

Structure for 2-Heptyl-4-quinolinol 1-oxide (PAMDB100075)

Structure for
2-Heptyl-4-quinolinol 1-oxide
(PAMDB100075)