2-HEPTYL-4-HYDROXYQUINOLINE N-OXIDE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C16H21NO2
Molecular Weight	259.3434
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of 2-HEPTYL-4-HYDROXYQUINOLINE N-OXIDE

Structure Search

SMILES

CCCCCCCC1=[N+]([O-])C2=CC=CC=C2C(O)=C1

InChI

InChIKey=NZPACTGCRWDXCJ-UHFFFAOYSA-N

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

HIDE SMILES / InChI

Molecular Formula	C16H21NO2
Molecular Weight	259.3434
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28708374

2-Heptyl-4-hydroxyquinoline N-oxide (HQNO), a component of the P. aeruginosa Pseudomonas quinolone signal (PQS) system, acts as a potent inhibitor of respiratory electron transfer and thereby affects host cells as well as microorganisms.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Dihydroorotate dehydrogenase B (NAD(+)), catalytic subunit 1 Target ID: Q636E2 Gene ID: NA Gene Symbol: pyrD Target Organism: Bacillus cereus (strain ZK / E33L) Sources: https://www.ncbi.nlm.nih.gov/pubmed/15607037	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2596

PubMed

Title	Date	PubMed
Lysine-91 of the tetraheme c-type cytochrome CymA is essential for quinone interaction and arsenate respiration in Shewanella sp. strain ANA-3.	2009-11	19760266
Investigation of the environment surrounding iron-sulfur cluster 4 of Escherichia coli dimethylsulfoxide reductase.	2005-06-07	15924426
Defining the Q-site of Escherichia coli fumarate reductase by site-directed mutagenesis, fluorescence quench titrations and EPR spectroscopy.	2005-01	15654871
Glutamate 87 is important for menaquinol binding in DmsC of the DMSO reductase (DmsABC) from Escherichia coli.	2004-01-28	14757221
Transient kinetic studies of heme reduction in Escherichia coli nitrate reductase A (NarGHI) by menaquinol.	2003-05-13	12731882
Electron transfer from heme bL to the [3Fe-4S] cluster of Escherichia coli nitrate reductase A (NarGHI).	2001-05-01	11318649
Generation of a proton potential by succinate dehydrogenase of Bacillus subtilis functioning as a fumarate reductase.	2001-05	11358526
[The role of Na+ ions in the respiration, formation of the membrane potential and movement of the alkali-resistant marine bacterium Vibrio alginolyticus].	1987-01	3814650

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Respiratory chain inhibitor 2-heptyl-4-hydroxyquinoline-N-oxide (HQNO) inhibited the activity of the NADH oxidase Bacillus cereus KCTC 3674 by about 90% at a concentration of 40 microM.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:29:16 GMT 2025` Edited by `admin` on `Mon Mar 31 19:29:16 GMT 2025`
Record UNII	1FU5S5CG6A
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

2-(N-HEPTYL)-4-HYDROXYQUINOLINE N-OXIDE

Preferred Name

English

2-HEPTYL-4-HYDROXYQUINOLINE N-OXIDE

Systematic Name

English

2-HEPTYL-4-QUINOLINOL 1-OXIDE

Systematic Name

English

4-QUINOLINOL, 2-HEPTYL-, 1-OXIDE

Systematic Name

English

HQNO [MI]

Common Name

English

Code System Code Type Description

EPA CompTox

DTXSID20955644