NP-MRD: Showing NP-Card for 2-n-Heptyl-4-hydroxyquinoline N-oxide (NP0068440)

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Record Information

Version

2.0

Created at

2022-04-28 13:36:59 UTC

Updated at

2022-04-28 13:36:59 UTC

NP-MRD ID

NP0068440

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-n-Heptyl-4-hydroxyquinoline N-oxide

Description

2-HEPTYL-4-HYDROXY QUINOLINE N-OXIDE, also known as HQNO or 2-(N-heptyl)-4-hydroxyquinoline N-oxide, 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. 2-HEPTYL-4-HYDROXY QUINOLINE N-OXIDE is a moderately basic compound (based on its pKa). 2-n-Heptyl-4-hydroxyquinoline N-oxide is found in Pseudomonas aeruginosa and Pseudonocardia sp. KUH-001. An inhibitor of the mitochondrial respiratory chain at cytochrome bc1 and of photosynthetic electron flow immediately before cytochrome b559.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 40 41  0  0  0  0  0  0  0  0999 V2000
   -6.4802    0.2227    0.6201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0056    0.4676    0.3341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4960   -0.7625   -0.3788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0454   -0.6751   -0.7313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1481   -0.5033    0.4666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7154   -0.4320   -0.0689 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2139   -0.2592    1.1099 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6160   -0.1833    0.6596 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3520   -1.3378    0.5529 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6571   -1.3052    0.1380 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4444   -2.4336    0.0123 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2002   -0.0729   -0.1670 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5254   -0.0102   -0.5915 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0680    1.2146   -0.8955 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3499    2.3760   -0.7952 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0329    2.2768   -0.3693 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4551    1.0743   -0.0567 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1683    1.0021    0.3568 N   0  0  0  0  0  4  0  0  0  0  0  0
    1.3910    2.1326    0.4791 O   0  0  0  0  0  1  0  0  0  0  0  0
   -6.7004    0.4551    1.6919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7587   -0.8459    0.4751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1319    0.8735    0.0213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4790    0.6758    1.2700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9582    1.3620   -0.3157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7530   -1.6810    0.1868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0633   -0.8293   -1.3350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8898    0.1136   -1.4817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7606   -1.6329   -1.2130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3769    0.3641    1.0832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1707   -1.3997    1.1194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6353    0.4080   -0.7600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4522   -1.3579   -0.5761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0968    0.6564    1.6359 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1176   -1.1067    1.8032 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9393   -2.3215    0.7898 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0830   -3.3519    0.2259 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1220   -0.9034   -0.6826 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0980    1.2516   -1.2242 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8312    3.2937   -1.0465 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4523    3.1849   -0.2849 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8 18  2  0
 18 19  1  0
 18 17  1  0
 17 16  2  0
 16 15  1  0
 15 14  2  0
 14 13  1  0
 13 12  2  0
 12 10  1  0
 10 11  1  0
 10  9  2  0
  9  8  1  0
 12 17  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  2 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
  7 33  1  0
  7 34  1  0
 16 40  1  0
 15 39  1  0
 14 38  1  0
 13 37  1  0
 11 36  1  0
  9 35  1  0
M  CHG  2  18   1  19  -1
M  END

HQO
  Mrv0541 02241213442D          

 19 20  0  0  0  0            999 V2000
   -1.9315    0.2961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6460    0.7086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2170    0.7086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5026    0.2961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5026   -0.5289    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    0.2119   -0.9414    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -1.2170   -0.9414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2170   -1.7664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9315   -2.1789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6460   -1.7664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6460   -0.9414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9315   -0.5289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2119    0.7086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6408    0.7086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9264    0.2961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3553    0.2961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0698    0.7086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7843    0.2961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4987    0.7086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  1 12  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4 13  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7 12  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 13 15  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
M  CHG  2   5   1   6  -1
M  END
> <DATABASE_ID>
NP0068440

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
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

> <INCHI_KEY>
NZPACTGCRWDXCJ-UHFFFAOYSA-N

> <FORMULA>
C16H21NO2

> <MOLECULAR_WEIGHT>
259.3434

> <EXACT_MASS>
259.157228921

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
30.463343666155893

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-heptyl-4-hydroxyquinolin-1-ium-1-olate

> <ALOGPS_LOGP>
2.56

> <JCHEM_LOGP>
4.190829990999999

> <ALOGPS_LOGS>
-4.41

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.879815967085363

> <JCHEM_PKA_STRONGEST_BASIC>
1.2231291025504167

> <JCHEM_POLAR_SURFACE_AREA>
45.69

> <JCHEM_REFRACTIVITY>
78.51490000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.00e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
hoqno

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: HQO                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -3.605   0.553   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -4.939   1.323   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -2.272   1.323   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.938   0.553   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0      -0.938  -0.987   0.000  0.00  0.00           N+1
HETATM    6  O   UNK     0       0.396  -1.757   0.000  0.00  0.00           O-1
HETATM    7  C   UNK     0      -2.272  -1.757   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.272  -3.297   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.605  -4.067   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.939  -3.297   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.939  -1.757   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.605  -0.987   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.396   1.323   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.063   1.323   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.729   0.553   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.397   0.553   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.730   1.323   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.064   0.553   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.398   1.323   0.000  0.00  0.00           C+0
CONECT    1    2    3   12                                                  
CONECT    2    1                                                            
CONECT    3    1    4                                                       
CONECT    4    3    5   13                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12    1    7   11                                                  
CONECT   13    4   15                                                       
CONECT   14   15   16                                                       
CONECT   15   13   14                                                       
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

View in JSmol

Synonyms

Value	Source
2-(N-Heptyl)-4-hydroxyquinoline N-oxide	ChEBI
2-Heptyl-4-hydroxyquinoline-N-oxide	ChEBI
2-Heptyl-4-quinolinol 1-oxide	ChEBI
HOQNO	ChEBI
HQNO	ChEBI
2-HEPTYL-4-hydroxy quinoline N-oxide	ChEBI

Chemical Formula

C₁₆H₂₁NO₂

Average Mass

259.3434 Da

Monoisotopic Mass

259.15723 Da

IUPAC Name

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

Traditional Name

hoqno

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

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

InChI Key

NZPACTGCRWDXCJ-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Pseudomonas aeruginosa	Bacteria	KNApSAcK
Pseudonocardia sp. KUH-001	--	KNApSAcK

Chemical Taxonomy

Description

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 (CHEBI:28362 )
quinoline N-oxide (CHEBI:28362 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.56	ALOGPS
logP	4.19	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	7.88	ChemAxon
pKa (Strongest Basic)	1.22	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	45.69 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	78.51 m³·mol⁻¹	ChemAxon
Polarizability	30.46 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

DB07918

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00026381

Chemspider ID

Not Available

KEGG Compound ID

C04284

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

28362

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 2-n-Heptyl-4-hydroxyquinoline N-oxide (NP0068440)

MOL for NP0068440 (2-n-Heptyl-4-hydroxyquinoline N-oxide)

3D MOL for NP0068440 (2-n-Heptyl-4-hydroxyquinoline N-oxide)

3D SDF for NP0068440 (2-n-Heptyl-4-hydroxyquinoline N-oxide)

3D-SDF for NP0068440 (2-n-Heptyl-4-hydroxyquinoline N-oxide)

PDB for NP0068440 (2-n-Heptyl-4-hydroxyquinoline N-oxide)

3D PDB for NP0068440 (2-n-Heptyl-4-hydroxyquinoline N-oxide)

SMILES for NP0068440 (2-n-Heptyl-4-hydroxyquinoline N-oxide)

INCHI for NP0068440 (2-n-Heptyl-4-hydroxyquinoline N-oxide)

Structure for NP0068440 (2-n-Heptyl-4-hydroxyquinoline N-oxide)

3D Structure for NP0068440 (2-n-Heptyl-4-hydroxyquinoline N-oxide)