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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 10:11:42 UTC

Update Date

2021-09-26 23:04:49 UTC

HMDB ID

HMDB0252316

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Flosequinan

Description

Flosequinan belongs to the class of organic compounds known as hydroquinolones. Hydroquinolones are compounds containing a hydrogenated quinoline bearing a ketone group. Flosequinan is an extremely weak basic (essentially neutral) compound (based on its pKa). It had been approved in 1992 in the US and UK to treat people with heart failure who could not tolerate ACE inhibitors or digitalis. Boots withdrew it from the market in July 1993. The study was terminated early in 1993 due to increased mortality in the drug arm of the trial; preliminary results were published in a conference abstract by the PI Milton Packer and others, which promised data and analysis would be forthcoming in a future paper, which was finally published in 2017. Boots initiated a clinical trial called PROFILE to see if the drug could be useful in a wider population. Flosequinan is a quinolone vasodilator that was discovered and developed by Boots UK and was sold for about a year under the trade name Manoplax. This compound has been identified in human blood as reported by (PMID: 31557052 ). Flosequinan is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Flosequinan is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv1572004221606212D          

 16 17  0  0  0  0            999 V2000
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  7  3  1  0  0  0  0
  7  5  2  0  0  0  0
  8  4  1  0  0  0  0
  9  5  1  0  0  0  0
  9  8  2  0  0  0  0
 10  6  2  0  0  0  0
 11  8  1  0  0  0  0
 11 10  1  0  0  0  0
 12  7  1  0  0  0  0
 13  1  1  0  0  0  0
 13  6  1  0  0  0  0
 13  9  1  0  0  0  0
 14 11  2  0  0  0  0
 16  2  1  0  0  0  0
 16 10  1  0  0  0  0
 16 15  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0252316

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1C=C(C(=O)C2=C1C=C(F)C=C2)S(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C11H10FNO2S/c1-13-6-10(16(2)15)11(14)8-4-3-7(12)5-9(8)13/h3-6H,1-2H3

> <INCHI_KEY>
UYGONJYYUKVHDD-UHFFFAOYSA-N

> <FORMULA>
C11H10FNO2S

> <MOLECULAR_WEIGHT>
239.26

> <EXACT_MASS>
239.041627903

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
22.88130453713848

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-fluoro-3-methanesulfinyl-1-methyl-1,4-dihydroquinolin-4-one

> <ALOGPS_LOGP>
1.13

> <JCHEM_LOGP>
0.7187198986666667

> <ALOGPS_LOGS>
-1.52

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3665969070493094

> <JCHEM_POLAR_SURFACE_AREA>
37.38

> <JCHEM_REFRACTIVITY>
63.818000000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.25e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
manoplax

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 22-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-APR-16         0                                  
HETATM    1  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   12  F   UNK     0       0.000   1.540   0.000  0.00  0.00           F+0
HETATM   13  N   UNK     0       5.335   1.540   0.000  0.00  0.00           N+0
HETATM   14  O   UNK     0       5.335   6.160   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       8.002   6.160   0.000  0.00  0.00           O+0
HETATM   16  S   UNK     0       8.002   4.620   0.000  0.00  0.00           S+0
CONECT    1   13                                                            
CONECT    2   16                                                            
CONECT    3    4    7                                                       
CONECT    4    3    8                                                       
CONECT    5    7    9                                                       
CONECT    6   10   13                                                       
CONECT    7    3    5   12                                                  
CONECT    8    4    9   11                                                  
CONECT    9    5    8   13                                                  
CONECT   10    6   11   16                                                  
CONECT   11    8   10   14                                                  
CONECT   12    7                                                            
CONECT   13    1    6    9                                                  
CONECT   14   11                                                            
CONECT   15   16                                                            
CONECT   16    2   10   15                                                  
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
7-Fluoro-1-methyl-3-methylsulfinyl-4-quinoline	MeSH
Flosequinan	MeSH
7-Fluoro-3-methanesulphinyl-1-methyl-1,4-dihydroquinolin-4-one	Generator

Chemical Formula

C₁₁H₁₀FNO₂S

Average Molecular Weight

239.26

Monoisotopic Molecular Weight

239.041627903

IUPAC Name

7-fluoro-3-methanesulfinyl-1-methyl-1,4-dihydroquinolin-4-one

Traditional Name

manoplax

CAS Registry Number

Not Available

SMILES

CN1C=C(C(=O)C2=C1C=C(F)C=C2)S(C)=O

InChI Identifier

InChI=1S/C11H10FNO2S/c1-13-6-10(16(2)15)11(14)8-4-3-7(12)5-9(8)13/h3-6H,1-2H3

InChI Key

UYGONJYYUKVHDD-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroquinolones. Hydroquinolones 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

Haloquinoline
Dihydroquinolone
Dihydroquinoline
Aryl fluoride
Aryl halide
Pyridine
Benzenoid
Heteroaromatic compound
Vinylogous amide
Sulfoxide
Sulfinyl compound
Azacycle
Hydrocarbon derivative
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organofluoride
Organohalogen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	1.13	ALOGPS
logP	0.72	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	37.38 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	63.82 m³·mol⁻¹	ChemAxon
Polarizability	22.88 Å³	ChemAxon
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	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	150.198	30932474
DeepCCS	[M-H]-	147.84	30932474
DeepCCS	[M-2H]-	181.348	30932474
DeepCCS	[M+Na]+	156.323	30932474
AllCCS	[M+H]+	150.4	32859911
AllCCS	[M+H-H2O]+	146.4	32859911
AllCCS	[M+NH4]+	154.1	32859911
AllCCS	[M+Na]+	155.2	32859911
AllCCS	[M-H]-	150.8	32859911
AllCCS	[M+Na-2H]-	150.8	32859911
AllCCS	[M+HCOO]-	150.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Flosequinan	CN1C=C(C(=O)C2=C1C=C(F)C=C2)S(C)=O	2508.0	Standard polar	33892256
Flosequinan	CN1C=C(C(=O)C2=C1C=C(F)C=C2)S(C)=O	2079.3	Standard non polar	33892256
Flosequinan	CN1C=C(C(=O)C2=C1C=C(F)C=C2)S(C)=O	2532.8	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Flosequinan GC-MS (Non-derivatized) - 70eV, Positive	splash10-00bi-1970000000-6f3b5f70b0b34fc93ccf	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Flosequinan GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Flosequinan 10V, Positive-QTOF	splash10-0006-0090000000-82af37210699854da382	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Flosequinan 20V, Positive-QTOF	splash10-0006-0190000000-d469b0f6eec420077528	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Flosequinan 40V, Positive-QTOF	splash10-0002-1940000000-366ded599c86b0a677d8	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Flosequinan 10V, Negative-QTOF	splash10-000i-0090000000-fdc5b0d2b640e2ed315c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Flosequinan 20V, Negative-QTOF	splash10-002r-0980000000-076b6a025276f24aa2d8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Flosequinan 40V, Negative-QTOF	splash10-0fb9-2900000000-a046f95d511ce0e0cbdc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Flosequinan 10V, Positive-QTOF	splash10-0006-0390000000-03ca118ba2eaa497bf31	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Flosequinan 20V, Positive-QTOF	splash10-0006-0090000000-ee853f3fdaa71507e17c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Flosequinan 40V, Positive-QTOF	splash10-0ffy-1910000000-591bcdb9aae1bddf049b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Flosequinan 10V, Negative-QTOF	splash10-000i-0090000000-c0cb14c565bc11a35a95	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Flosequinan 20V, Negative-QTOF	splash10-004r-2980000000-1e873373b8cbe57c93a9	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Flosequinan 40V, Negative-QTOF	splash10-024i-6900000000-0eb327d363f7debb8811	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB13228

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Flosequinan

METLIN ID

Not Available

PubChem Compound

4474062

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Flosequinan (HMDB0252316)

MOL for HMDB0252316 (Flosequinan)

3D MOL for HMDB0252316 (Flosequinan)

3D SDF for HMDB0252316 (Flosequinan)

3D-SDF for HMDB0252316 (Flosequinan)

PDB for HMDB0252316 (Flosequinan)

3D PDB for HMDB0252316 (Flosequinan)

SMILES for HMDB0252316 (Flosequinan)

INCHI for HMDB0252316 (Flosequinan)

Structure for HMDB0252316 (Flosequinan)

3D Structure for HMDB0252316 (Flosequinan)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra