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Showing metabocard for Chloroxine (HMDB0015373)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2022-03-07 02:51:58 UTC
HMDB IDHMDB0015373
Secondary Accession Numbers
  • HMDB15373
Metabolite Identification
Common NameChloroxine
DescriptionChloroxine is only found in individuals that have used or taken this drug. It is a synthetic antibacterial compound. Chloroxine is a compound used in some shampoos for the treatment of dandruff and seborrheic dermatitis of the scalp.Although the mechanism of action is not understood, chloroxine may slow down mitotic activity in the epidermis, thereby reducing excessive scaling associated with dandruff or seborrheic dermatitis of the scalp. Chloroxine induces SOS-DNA repair in E. coli, so chloroxine may be genotoxic to bacteria.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0015373 (Chloroxine)

1243
  Mrv0541 02231215212D          

 13 14  0  0  0  0            999 V2000
    3.0786    1.7777    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.6498   -0.6970    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.0786   -1.5219    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5303   -0.7257    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7929    0.5403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7929   -0.2846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0786   -0.6970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0786    0.9528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5303    0.9814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3641   -0.2846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3641    0.5403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2777    0.5574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2777   -0.3018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  8  1  0  0  0  0
  2 10  1  0  0  0  0
  3  7  1  0  0  0  0
  4  6  1  0  0  0  0
  4 13  2  0  0  0  0
  5  6  2  0  0  0  0
  5  8  1  0  0  0  0
  5  9  1  0  0  0  0
  6  7  1  0  0  0  0
  7 10  2  0  0  0  0
  8 11  2  0  0  0  0
  9 12  2  0  0  0  0
 10 11  1  0  0  0  0
 12 13  1  0  0  0  0
M  END
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3D MOL for HMDB0015373 (Chloroxine)

HMDB0015373
     RDKit          3D
Chloroxine
 18 19  0  0  0  0  0  0  0  0999 V2000
    1.8972   -2.1712   -0.1791 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4109   -0.8684   -0.1206 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2456    0.2376   -0.1647 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9736    0.0059   -0.2983 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.7252    1.5146   -0.1041 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3711    1.6877    0.0005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3540    3.3003    0.0822 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.4549    0.5756    0.0439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8341    0.7843    0.1510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6639   -0.3161    0.1948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1215   -1.5821    0.1327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7946   -1.7736    0.0298 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0529   -0.7043   -0.0158 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9069   -2.2872   -0.2569 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3824    2.3638   -0.1391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2064    1.7902    0.1959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7276   -0.1343    0.2777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8088   -2.4229    0.1702 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13  2  1  0
 13  8  1  0
  1 14  1  0
  5 15  1  0
  9 16  1  0
 10 17  1  0
 11 18  1  0
M  END
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3D SDF for HMDB0015373 (Chloroxine)

1243
  Mrv0541 02231215212D          

 13 14  0  0  0  0            999 V2000
    3.0786    1.7777    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.6498   -0.6970    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.0786   -1.5219    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5303   -0.7257    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7929    0.5403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7929   -0.2846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0786   -0.6970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0786    0.9528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5303    0.9814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3641   -0.2846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3641    0.5403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2777    0.5574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2777   -0.3018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  8  1  0  0  0  0
  2 10  1  0  0  0  0
  3  7  1  0  0  0  0
  4  6  1  0  0  0  0
  4 13  2  0  0  0  0
  5  6  2  0  0  0  0
  5  8  1  0  0  0  0
  5  9  1  0  0  0  0
  6  7  1  0  0  0  0
  7 10  2  0  0  0  0
  8 11  2  0  0  0  0
  9 12  2  0  0  0  0
 10 11  1  0  0  0  0
 12 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015373

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=C(Cl)C=C(Cl)C2=C1N=CC=C2

> <INCHI_IDENTIFIER>
InChI=1S/C9H5Cl2NO/c10-6-4-7(11)9(13)8-5(6)2-1-3-12-8/h1-4,13H

> <INCHI_KEY>
WDFKMLRRRCGAKS-UHFFFAOYSA-N

> <FORMULA>
C9H5Cl2NO

> <MOLECULAR_WEIGHT>
214.048

> <EXACT_MASS>
212.974819201

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
19.322074782592896

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5,7-dichloroquinolin-8-ol

> <ALOGPS_LOGP>
3.44

> <JCHEM_LOGP>
3.035424502333333

> <ALOGPS_LOGS>
-3.19

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.954170972705197

> <JCHEM_PKA_STRONGEST_BASIC>
3.3963142832284525

> <JCHEM_POLAR_SURFACE_AREA>
33.120000000000005

> <JCHEM_REFRACTIVITY>
51.56980000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.38e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
chloroxine

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0015373 (Chloroxine)

HMDB0015373
     RDKit          3D
Chloroxine
 18 19  0  0  0  0  0  0  0  0999 V2000
    1.8972   -2.1712   -0.1791 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4109   -0.8684   -0.1206 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2456    0.2376   -0.1647 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9736    0.0059   -0.2983 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.7252    1.5146   -0.1041 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3711    1.6877    0.0005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3540    3.3003    0.0822 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.4549    0.5756    0.0439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8341    0.7843    0.1510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6639   -0.3161    0.1948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1215   -1.5821    0.1327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7946   -1.7736    0.0298 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0529   -0.7043   -0.0158 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9069   -2.2872   -0.2569 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3824    2.3638   -0.1391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2064    1.7902    0.1959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7276   -0.1343    0.2777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8088   -2.4229    0.1702 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13  2  1  0
 13  8  1  0
  1 14  1  0
  5 15  1  0
  9 16  1  0
 10 17  1  0
 11 18  1  0
M  END
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PDB for HMDB0015373 (Chloroxine)

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1243                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Cl   UNK     0       5.747   3.318   0.000  0.00  0.00          Cl+0
HETATM    2 Cl   UNK     0       3.080  -1.301   0.000  0.00  0.00          Cl+0
HETATM    3  O   UNK     0       5.747  -2.841   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       8.457  -1.355   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       7.080   1.009   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.080  -0.531   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.747  -1.301   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.747   1.779   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.457   1.832   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.413  -0.531   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.413   1.009   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.852   1.041   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.852  -0.563   0.000  0.00  0.00           C+0
CONECT    1    8                                                            
CONECT    2   10                                                            
CONECT    3    7                                                            
CONECT    4    6   13                                                       
CONECT    5    6    8    9                                                  
CONECT    6    4    5    7                                                  
CONECT    7    3    6   10                                                  
CONECT    8    1    5   11                                                  
CONECT    9    5   12                                                       
CONECT   10    2    7   11                                                  
CONECT   11    8   10                                                       
CONECT   12    9   13                                                       
CONECT   13    4   12                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END
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3D PDB for HMDB0015373 (Chloroxine)

COMPND    HMDB0015373
HETATM    1  O1  UNL     1       1.897  -2.171  -0.179  1.00  0.00           O  
HETATM    2  C1  UNL     1       1.411  -0.868  -0.121  1.00  0.00           C  
HETATM    3  C2  UNL     1       2.246   0.238  -0.165  1.00  0.00           C  
HETATM    4 CL1  UNL     1       3.974   0.006  -0.298  1.00  0.00          CL  
HETATM    5  C3  UNL     1       1.725   1.515  -0.104  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.371   1.688   0.001  1.00  0.00           C  
HETATM    7 CL2  UNL     1      -0.354   3.300   0.082  1.00  0.00          CL  
HETATM    8  C5  UNL     1      -0.455   0.576   0.044  1.00  0.00           C  
HETATM    9  C6  UNL     1      -1.834   0.784   0.151  1.00  0.00           C  
HETATM   10  C7  UNL     1      -2.664  -0.316   0.195  1.00  0.00           C  
HETATM   11  C8  UNL     1      -2.121  -1.582   0.133  1.00  0.00           C  
HETATM   12  N1  UNL     1      -0.795  -1.774   0.030  1.00  0.00           N  
HETATM   13  C9  UNL     1       0.053  -0.704  -0.016  1.00  0.00           C  
HETATM   14  H1  UNL     1       2.907  -2.287  -0.257  1.00  0.00           H  
HETATM   15  H2  UNL     1       2.382   2.364  -0.139  1.00  0.00           H  
HETATM   16  H3  UNL     1      -2.206   1.790   0.196  1.00  0.00           H  
HETATM   17  H4  UNL     1      -3.728  -0.134   0.278  1.00  0.00           H  
HETATM   18  H5  UNL     1      -2.809  -2.423   0.170  1.00  0.00           H  
CONECT    1    2   14
CONECT    2    3    3   13
CONECT    3    4    5
CONECT    5    6    6   15
CONECT    6    7    8
CONECT    8    9    9   13
CONECT    9   10   16
CONECT   10   11   11   17
CONECT   11   12   18
CONECT   12   13   13
END
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SMILES for HMDB0015373 (Chloroxine)

OC1=C(Cl)C=C(Cl)C2=C1N=CC=C2
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INCHI for HMDB0015373 (Chloroxine)

InChI=1S/C9H5Cl2NO/c10-6-4-7(11)9(13)8-5(6)2-1-3-12-8/h1-4,13H
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View in JSmolView Stereo Labels
Synonyms
Chemical FormulaC9H5Cl2NO
Average Molecular Weight214.048
Monoisotopic Molecular Weight212.974819201
IUPAC Name5,7-dichloroquinolin-8-ol
Traditional Namechloroxine
CAS Registry Number773-76-2
SMILES
OC1=C(Cl)C=C(Cl)C2=C1N=CC=C2
InChI Identifier
InChI=1S/C9H5Cl2NO/c10-6-4-7(11)9(13)8-5(6)2-1-3-12-8/h1-4,13H
InChI KeyWDFKMLRRRCGAKS-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as chloroquinolines. Chloroquinolines are compounds containing a quinoline moiety, which carries one or more chlorine atoms.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassQuinolines and derivatives
Sub ClassHaloquinolines
Direct ParentChloroquinolines
Alternative Parents
Substituents
  • 8-hydroxyquinoline
  • Chloroquinoline
  • Aryl chloride
  • Aryl halide
  • Pyridine
  • Benzenoid
  • Heteroaromatic compound
  • Azacycle
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Organic oxygen compound
  • Organic nitrogen 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 Point179.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.14 g/LNot Available
LogP3Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01243 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01243 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01243
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2621
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkChloroxine
METLIN IDNot Available
PubChem Compound2722
PDB IDNot Available
ChEBI ID59477
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 References
  1. Malaveille C, Brun G, Bartsch H: Genotoxicity of ochratoxin A and structurally related compounds in Escherichia coli strains: studies on their mode of action. IARC Sci Publ. 1991;(115):261-6. [PubMed:1820340 ]
  2. Malaveille C, Brun G, Bartsch H: Structure-activity studies in E. coli strains on ochratoxin A (OTA) and its analogues implicate a genotoxic free radical and a cytotoxic thiol derivative as reactive metabolites. Mutat Res. 1994 May 1;307(1):141-7. [PubMed:7513790 ]