MiMeDB: Showing metabocard for 2-Heptyl-4-quinolinol 1-oxide (MMDBc0032878)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-18 22:21:18 UTC

Update Date

2022-08-31 21:44:50 UTC

Metabolite ID

MMDBc0032878

Metabolite Identification

Common 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

Structure

MOL SDF PDB SMILES InChI

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>
MMDBc0032878

> <DATABASE_NAME>
MIME

> <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

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

Molecular Formula

C₁₆H₂₁NO₂

Average Mass

259.3434

Monoisotopic Mass

259.157228921

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

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 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.01 g/L	ALOGPS
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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0abc-9450000000-93f38f6322941ef1484a	2017-08-28	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0090000000-4e34a689710ed72ad430	2017-07-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-4290000000-33d556fd67167b8ac37e	2017-07-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9200000000-bd8d53ad60bb83c284df	2017-07-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0090000000-2454b42ad77acddc0323	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0090000000-b9275e5c37c7fdf029d8	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0zms-9450000000-16be32adc045347e5b0a	2017-07-26	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	1	Human ; Human sputum; Human subgingival plaque; Human feces	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

DB07918

Phenol Explorer Compound ID

Not Available

FooDB 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

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Huang W, Brewer LK, Jones JW, Nguyen AT, Marcu A, Wishart DS, Oglesby-Sherrouse AG, Kane MA, Wilks A: PAMDB: a comprehensive Pseudomonas aeruginosa metabolome database. Nucleic Acids Res. 2018 Jan 4;46(D1):D575-D580. doi: 10.1093/nar/gkx1061. [PubMed:29106626 ]

Showing metabocard for 2-Heptyl-4-quinolinol 1-oxide (MMDBc0032878)

MOL for #<Metabolite:0x00007f46d401ece0>

3D MOL for #<Metabolite:0x00007f46d401ece0>

3D SDF for #<Metabolite:0x00007f46d401ece0>

3D-SDF for #<Metabolite:0x00007f46d401ece0>

PDB for #<Metabolite:0x00007f46d401ece0>

3D PDB for #<Metabolite:0x00007f46d401ece0>

SMILES for #<Metabolite:0x00007f46d401ece0>

INCHI for #<Metabolite:0x00007f46d401ece0>

Structure for #<Metabolite:0x00007f46d401ece0>

3D Structure for #<Metabolite:0x00007f46d401ece0>