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Showing metabocard for Nitroxoline (HMDB0015491)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2023-02-21 17:18:30 UTC
HMDB IDHMDB0015491
Secondary Accession Numbers
  • HMDB15491
Metabolite Identification
Common NameNitroxoline
DescriptionNitroxoline is only found in individuals that have used or taken this drug. It is a urinary antibacterial agent active against susceptible gram-positive and gram-negative organisms commonly found in urinary tract infections. It is a fluorquinolone that is active against bacterial gyrases.This drug may also have antitumor activity by inhibition of ype 2 methionine aminopeptidase (MetAP2) protein which is involved in angiogenesis. Its antibacterial activity may stem from the metal ion complexation vital for bacterial growth.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0015491 (Nitroxoline)

1422
  Mrv0541 02231215292D          

 14 15  0  0  0  0            999 V2000
    2.3641    1.7282    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6498   -1.9838    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    3.0786   -1.9838    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8160    0.9319    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3641   -1.5714    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    3.0786   -0.3341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0786    0.4908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3641   -0.7465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3641    0.9033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6498   -0.3341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8160   -0.7752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6498    0.4908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5634   -0.3513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5634    0.5079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  9  1  0  0  0  0
  2  5  1  0  0  0  0
  3  5  2  0  0  0  0
  4  7  1  0  0  0  0
  4 14  2  0  0  0  0
  5  8  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  6 11  1  0  0  0  0
  7  9  2  0  0  0  0
  8 10  1  0  0  0  0
  9 12  1  0  0  0  0
 10 12  2  0  0  0  0
 11 13  2  0  0  0  0
 13 14  1  0  0  0  0
M  CHG  2   2  -1   5   1
M  END
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3D MOL for HMDB0015491 (Nitroxoline)

HMDB0015491
     RDKit          3D
Nitroxoline
 20 21  0  0  0  0  0  0  0  0999 V2000
    3.0911   -1.9993   -0.2735 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5302   -0.9223    0.1373 N   0  0  0  0  0  4  0  0  0  0  0  0
    3.3877    0.0530    0.4901 O   0  0  0  0  0  1  0  0  0  0  0  0
    1.1287   -0.9364    0.1493 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4772   -2.1573    0.3414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8873   -2.2249    0.3582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6162   -1.0742    0.1833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0005   -1.0797    0.1907 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9786    0.1535   -0.0103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6955    1.2779   -0.1878 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1556    2.4894   -0.3856 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2101    2.6219   -0.4141 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9791    1.4692   -0.2320 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4170    0.2274   -0.0285 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0817   -3.0557    0.4775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4394   -3.1440    0.5037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4927   -0.2149    0.0578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7727    3.3911   -0.5264 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6922    3.5732   -0.5707 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0435    1.5521   -0.2603 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  4  1  0
 14  9  1  0
  5 15  1  0
  6 16  1  0
  8 17  1  0
 11 18  1  0
 12 19  1  0
 13 20  1  0
M  CHG  2   2   1   3  -1
M  END
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3D SDF for HMDB0015491 (Nitroxoline)

1422
  Mrv0541 02231215292D          

 14 15  0  0  0  0            999 V2000
    2.3641    1.7282    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6498   -1.9838    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    3.0786   -1.9838    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8160    0.9319    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3641   -1.5714    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    3.0786   -0.3341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0786    0.4908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3641   -0.7465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3641    0.9033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6498   -0.3341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8160   -0.7752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6498    0.4908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5634   -0.3513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5634    0.5079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  9  1  0  0  0  0
  2  5  1  0  0  0  0
  3  5  2  0  0  0  0
  4  7  1  0  0  0  0
  4 14  2  0  0  0  0
  5  8  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  6 11  1  0  0  0  0
  7  9  2  0  0  0  0
  8 10  1  0  0  0  0
  9 12  1  0  0  0  0
 10 12  2  0  0  0  0
 11 13  2  0  0  0  0
 13 14  1  0  0  0  0
M  CHG  2   2  -1   5   1
M  END
> <DATABASE_ID>
HMDB0015491

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=C2N=CC=CC2=C(C=C1)[N+]([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C9H6N2O3/c12-8-4-3-7(11(13)14)6-2-1-5-10-9(6)8/h1-5,12H

> <INCHI_KEY>
RJIWZDNTCBHXAL-UHFFFAOYSA-N

> <FORMULA>
C9H6N2O3

> <MOLECULAR_WEIGHT>
190.1555

> <EXACT_MASS>
190.037842068

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
17.163202295729285

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-nitroquinolin-8-ol

> <ALOGPS_LOGP>
1.90

> <JCHEM_LOGP>
1.767319339

> <ALOGPS_LOGS>
-1.84

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.8755887406986

> <JCHEM_PKA_STRONGEST_BASIC>
2.08166459790019

> <JCHEM_POLAR_SURFACE_AREA>
78.94

> <JCHEM_REFRACTIVITY>
49.284900000000015

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.73e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
nitroxoline

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0015491 (Nitroxoline)

HMDB0015491
     RDKit          3D
Nitroxoline
 20 21  0  0  0  0  0  0  0  0999 V2000
    3.0911   -1.9993   -0.2735 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5302   -0.9223    0.1373 N   0  0  0  0  0  4  0  0  0  0  0  0
    3.3877    0.0530    0.4901 O   0  0  0  0  0  1  0  0  0  0  0  0
    1.1287   -0.9364    0.1493 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4772   -2.1573    0.3414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8873   -2.2249    0.3582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6162   -1.0742    0.1833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0005   -1.0797    0.1907 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9786    0.1535   -0.0103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6955    1.2779   -0.1878 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1556    2.4894   -0.3856 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2101    2.6219   -0.4141 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9791    1.4692   -0.2320 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4170    0.2274   -0.0285 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0817   -3.0557    0.4775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4394   -3.1440    0.5037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4927   -0.2149    0.0578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7727    3.3911   -0.5264 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6922    3.5732   -0.5707 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0435    1.5521   -0.2603 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  4  1  0
 14  9  1  0
  5 15  1  0
  6 16  1  0
  8 17  1  0
 11 18  1  0
 12 19  1  0
 13 20  1  0
M  CHG  2   2   1   3  -1
M  END
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PDB for HMDB0015491 (Nitroxoline)

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1422                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       4.413   3.226   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       3.080  -3.703   0.000  0.00  0.00           O-1
HETATM    3  O   UNK     0       5.747  -3.703   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       7.123   1.739   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0       4.413  -2.933   0.000  0.00  0.00           N+1
HETATM    6  C   UNK     0       5.747  -0.624   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.747   0.916   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.413  -1.393   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.413   1.686   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.080  -0.624   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.123  -1.447   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.080   0.916   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.518  -0.656   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.518   0.948   0.000  0.00  0.00           C+0
CONECT    1    9                                                            
CONECT    2    5                                                            
CONECT    3    5                                                            
CONECT    4    7   14                                                       
CONECT    5    2    3    8                                                  
CONECT    6    7    8   11                                                  
CONECT    7    4    6    9                                                  
CONECT    8    5    6   10                                                  
CONECT    9    1    7   12                                                  
CONECT   10    8   12                                                       
CONECT   11    6   13                                                       
CONECT   12    9   10                                                       
CONECT   13   11   14                                                       
CONECT   14    4   13                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END
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3D PDB for HMDB0015491 (Nitroxoline)

COMPND    HMDB0015491
HETATM    1  O1  UNL     1       3.091  -1.999  -0.274  1.00  0.00           O  
HETATM    2  N1  UNL     1       2.530  -0.922   0.137  1.00  0.00           N1+
HETATM    3  O2  UNL     1       3.388   0.053   0.490  1.00  0.00           O1-
HETATM    4  C1  UNL     1       1.129  -0.936   0.149  1.00  0.00           C  
HETATM    5  C2  UNL     1       0.477  -2.157   0.341  1.00  0.00           C  
HETATM    6  C3  UNL     1      -0.887  -2.225   0.358  1.00  0.00           C  
HETATM    7  C4  UNL     1      -1.616  -1.074   0.183  1.00  0.00           C  
HETATM    8  O3  UNL     1      -3.000  -1.080   0.191  1.00  0.00           O  
HETATM    9  C5  UNL     1      -0.979   0.154  -0.010  1.00  0.00           C  
HETATM   10  N2  UNL     1      -1.696   1.278  -0.188  1.00  0.00           N  
HETATM   11  C6  UNL     1      -1.156   2.489  -0.386  1.00  0.00           C  
HETATM   12  C7  UNL     1       0.210   2.622  -0.414  1.00  0.00           C  
HETATM   13  C8  UNL     1       0.979   1.469  -0.232  1.00  0.00           C  
HETATM   14  C9  UNL     1       0.417   0.227  -0.028  1.00  0.00           C  
HETATM   15  H1  UNL     1       1.082  -3.056   0.478  1.00  0.00           H  
HETATM   16  H2  UNL     1      -1.439  -3.144   0.504  1.00  0.00           H  
HETATM   17  H3  UNL     1      -3.493  -0.215   0.058  1.00  0.00           H  
HETATM   18  H4  UNL     1      -1.773   3.391  -0.526  1.00  0.00           H  
HETATM   19  H5  UNL     1       0.692   3.573  -0.571  1.00  0.00           H  
HETATM   20  H6  UNL     1       2.044   1.552  -0.260  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    4    5    5   14
CONECT    5    6   15
CONECT    6    7    7   16
CONECT    7    8    9
CONECT    8   17
CONECT    9   10   10   14
CONECT   10   11
CONECT   11   12   12   18
CONECT   12   13   19
CONECT   13   14   14   20
END
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SMILES for HMDB0015491 (Nitroxoline)

OC1=C2N=CC=CC2=C(C=C1)[N+]([O-])=O
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INCHI for HMDB0015491 (Nitroxoline)

InChI=1S/C9H6N2O3/c12-8-4-3-7(11(13)14)6-2-1-5-10-9(6)8/h1-5,12H
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
5-Nitro-8-hydroxyquinolineChEBI
5-Nitro-8-oxyquinolineChEBI
5-Nitro-8-quinolinolChEBI
5-NitroxChEBI
5-NOKChEBI
5NOKChEBI
8-Hydroxy-5-nitroquinolineChEBI
NitroxolinaChEBI
NitroxolinumChEBI
5-NitroksHMDB
5-NitroxineHMDB
Cysto-saar plusHMDB
Nitroxoline monofluorideHMDB
Nitroxoline, potassium saltHMDB
5-Nitroquinolin-8-olHMDB
NibiolHMDB
Chemical FormulaC9H6N2O3
Average Molecular Weight190.1555
Monoisotopic Molecular Weight190.037842068
IUPAC Name5-nitroquinolin-8-ol
Traditional Namenitroxoline
CAS Registry Number4008-48-4
SMILES
OC1=C2N=CC=CC2=C(C=C1)[N+]([O-])=O
InChI Identifier
InChI=1S/C9H6N2O3/c12-8-4-3-7(11(13)14)6-2-1-5-10-9(6)8/h1-5,12H
InChI KeyRJIWZDNTCBHXAL-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as nitroquinolines and derivatives. Nitroquinolines and derivatives are compounds containing a nitro group attached to a quinoline moiety.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassQuinolines and derivatives
Sub ClassNitroquinolines and derivatives
Direct ParentNitroquinolines and derivatives
Alternative Parents
Substituents
  • Nitroquinoline
  • 8-hydroxyquinoline
  • Nitroaromatic compound
  • 1-hydroxy-2-unsubstituted benzenoid
  • Pyridine
  • Benzenoid
  • Heteroaromatic compound
  • C-nitro compound
  • Organic nitro compound
  • Organic oxoazanium
  • Azacycle
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Allyl-type 1,3-dipolar organic compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic zwitterion
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point180 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility2.73 g/LNot Available
LogP1.99HANSCH,C ET AL. (1995)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01422 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01422 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01422
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID18756
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNitroxoline
METLIN IDNot Available
PubChem Compound19910
PDB IDHNQ
ChEBI ID67121
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Methionine aminopeptidase 1
General function:
Involved in aminopeptidase activity
Specific function:
Removes the amino-terminal methionine from nascent proteins. Required for normal progression through the cell cycle
Gene Name:
METAP1
Uniprot ID:
P53582
Molecular weight:
43214.9
References
  1. Shim JS, Matsui Y, Bhat S, Nacev BA, Xu J, Bhang HE, Dhara S, Han KC, Chong CR, Pomper MG, So A, Liu JO: Effect of nitroxoline on angiogenesis and growth of human bladder cancer. J Natl Cancer Inst. 2010 Dec 15;102(24):1855-73. doi: 10.1093/jnci/djq457. Epub 2010 Nov 18. [PubMed:21088277 ]