P. aeruginosa Metabolome Database: 2-heptyl-4-quinolone (PAMDB100072)

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

PAMDB100072

Identification

Name:

2-heptyl-4-quinolone

Description:

2-heptyl-4-quinolone (HHQ) is an important quorum signaling molecule in P. aeruginosa. HHQ is involved in modulating swarming motility and inducing virulence gene expression in P. aeruginosa. HHQ is the precursor of PQS (Pseudomonas quinolone signal).

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

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

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

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

• 2-heptyl-4-quinolone

• 2-Heptylquinolin-4(1H)-one

• 2-n-heptyl-4-quinolinol

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

• 4-hydroxy-2-heptylquinoline

• tcmdc-132026

• [40522-46-1]

• 2503-80-2 [RN]

• 2-heptyl-1H-quinolin-4-one

• 2-heptyl-4(1H)-quinoline

• 2-heptyl-4(1H)-quinolone

• 2-Heptyl-4-hydroxyquinoline

• 2-heptylquinolin-4-ol

• 40522-46-1 [RN]

• HHQ

• MFCD16619170 [MDL number]

• MY 12-62c

• MY-12-62c

• pseudan VII

Chemical Formula:

C₁₆H₂₁N

Average Molecular Weight:

243.344

Monoisotopic Molecular Weight:

243.162308

InChI Key:

UYRHHBXYXSYGHA-UHFFFAOYSA-N

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)

CAS number:

2503-80-2

IUPAC Name:

2-heptyl-1,4-dihydroquinolin-4-one

Traditional IUPAC Name:

Not Available

SMILES:

CCCCCCCc1cc(=O)c2ccccc2[nH]1

Chemical Taxonomy

Taxonomy Description

This compound belongs to the class of organic compounds known as hydroquinolones. These are compounds containing a hydrogenated quinoline bearing a ketone group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Quinolones and derivatives

Direct Parent

Hydroquinolones

Alternative Parents

Substituents

Dihydroquinolone
Dihydroquinoline
Benzenoid
Pyridine
Heteroaromatic compound
Vinylogous amide
Azacycle
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

quinolone (CHEBI:62219)
a tautomer (CPD-12836)

Physical Properties

State:

Solid, off white powder

Charge:

Melting point:

Not Available

Experimental Properties:

Soluble in DMSO 5 mg/mL

Predicted Properties

Property	Value	Source
Water Solubility	2.1 mg/L	EPIsuite
logP	4.90	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	29.10 Å2	ChemAxon
Solvent Accessible surface area	404.99	ChemAxon
Rotatable Bond Count	6	ChemAxon
Molar Refractivity	74.0 cm3	ACD/Labs
Polarizability	29.3 10-24cm3	ACD/Labs
Density	1.0 g/cm3	ACD/Labs
Boiling point	361.5°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	No	ChemAxon
Muegge Filter	Yes	ChemAxon

Biological Properties

Cellular Locations:

Not Available

Reactions:

2-aminobenzoylacetate + Octanoyl-CoA → H2O + CO2 + Coenzyme A+HHQ
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

Links

External Links:

Resource	Link
Resource	Link
PubChem	164974
Chemspider	144633

2-heptyl-4-quinolone (PAMDB100072)

Structure for 2-heptyl-4-quinolone (PAMDB100072)

Structure for
2-heptyl-4-quinolone
(PAMDB100072)