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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2023-02-21 17:18:28 UTC

HMDB ID

HMDB0015319

Secondary Accession Numbers

HMDB15319

Metabolite Identification

Common Name

Ciclopirox

Description

Ciclopirox is only found in individuals that have used or taken this drug. It is a synthetic antifungal agent for topical dermatologic use. [Wikipedia ] Unlike antifungals such as itraconazole and terbinafine, which affect sterol synthesis, ciclopirox is thought to act through the chelation of polyvalent metal cations, such as Fe³⁺ and Al³⁺. These cations inhibit many enzymes, including cytochromes, thus disrupting cellular activities such as mitochondrial electron transport processes and energy production. Ciclopirox also appears to modify the plasma membrane of fungi, resulting in the disorganization of internal structures. The anti-inflammatory action of ciclopirox is most likely due to inhibition of 5-lipoxygenase and cyclooxygenase. Ciclopirox may exert its effect by disrupting DNA repair, cell division signals and structures (mitotic spindles) as well as some elements of intracellular transport.

Structure

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

HMDB0015319
     RDKit          3D
Ciclopirox
 32 33  0  0  0  0  0  0  0  0999 V2000
   -2.8888    2.2566    0.7917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4083    0.8756    0.5421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0802    0.5873    0.3269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6547   -0.7175    0.0949 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7930   -1.0222   -0.1376 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5533   -0.7686    1.1034 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3419    0.4831    1.1841 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1856    0.6132   -0.0625 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2488    0.7280   -1.2284 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2921   -0.3805   -1.3771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6078   -1.6670    0.0936 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1741   -2.9692   -0.1391 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9151   -1.4052    0.3024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6921   -2.4043    0.2711 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3401   -0.1389    0.5293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3347    2.9623    0.1414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9696    2.3327    0.5958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7216    2.4987    1.8642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3527    1.3938    0.3384 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8238   -2.1376   -0.3131 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8385   -0.7702    1.9792 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2540   -1.6215    1.3463 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7881    1.3944    1.4142 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0803    0.3585    2.0315 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8856   -0.2227   -0.1196 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7535    1.5630    0.0158 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7474    1.7221   -1.1562 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8983    0.8077   -2.1496 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7368   -1.1239   -2.1053 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3937    0.0159   -1.9394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0759   -3.2728   -1.0957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3988    0.0291    0.6924 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  4 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 13 15  1  0
 15  2  2  0
 10  5  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  3 19  1  0
  5 20  1  0
  6 21  1  0
  6 22  1  0
  7 23  1  0
  7 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 12 31  1  0
 15 32  1  0
M  END

1188
  Mrv0541 02231215182D          

 15 16  0  0  0  0            999 V2000
    4.5080   -1.4438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -0.6188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.6188    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  1  0  0  0  0
  2 13  2  0  0  0  0
  3 10  1  0  0  0  0
  3 13  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  4 10  1  0  0  0  0
  5  7  1  0  0  0  0
  6  8  1  0  0  0  0
  7  9  1  0  0  0  0
  8  9  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 14  2  0  0  0  0
 12 15  1  0  0  0  0
 13 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015319

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=CC(=O)N(O)C(=C1)C1CCCCC1

> <INCHI_IDENTIFIER>
InChI=1S/C12H17NO2/c1-9-7-11(13(15)12(14)8-9)10-5-3-2-4-6-10/h7-8,10,15H,2-6H2,1H3

> <INCHI_KEY>
SCKYRAXSEDYPSA-UHFFFAOYSA-N

> <FORMULA>
C12H17NO2

> <MOLECULAR_WEIGHT>
207.2689

> <EXACT_MASS>
207.125928793

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
23.117942047063018

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-cyclohexyl-1-hydroxy-4-methyl-1,2-dihydropyridin-2-one

> <ALOGPS_LOGP>
2.15

> <JCHEM_LOGP>
2.216589469333334

> <ALOGPS_LOGS>
-2.17

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.842140564132407

> <JCHEM_PKA_STRONGEST_BASIC>
-6.194129902384247

> <JCHEM_POLAR_SURFACE_AREA>
40.54

> <JCHEM_REFRACTIVITY>
60.907399999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.41e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
penlac

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015319
     RDKit          3D
Ciclopirox
 32 33  0  0  0  0  0  0  0  0999 V2000
   -2.8888    2.2566    0.7917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4083    0.8756    0.5421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0802    0.5873    0.3269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6547   -0.7175    0.0949 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7930   -1.0222   -0.1376 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5533   -0.7686    1.1034 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3419    0.4831    1.1841 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1856    0.6132   -0.0625 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2488    0.7280   -1.2284 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2921   -0.3805   -1.3771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6078   -1.6670    0.0936 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1741   -2.9692   -0.1391 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9151   -1.4052    0.3024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6921   -2.4043    0.2711 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3401   -0.1389    0.5293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3347    2.9623    0.1414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9696    2.3327    0.5958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7216    2.4987    1.8642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3527    1.3938    0.3384 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8238   -2.1376   -0.3131 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8385   -0.7702    1.9792 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2540   -1.6215    1.3463 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7881    1.3944    1.4142 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0803    0.3585    2.0315 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8856   -0.2227   -0.1196 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7535    1.5630    0.0158 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7474    1.7221   -1.1562 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8983    0.8077   -2.1496 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7368   -1.1239   -2.1053 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3937    0.0159   -1.9394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0759   -3.2728   -1.0957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3988    0.0291    0.6924 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  4 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 13 15  1  0
 15  2  2  0
 10  5  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  3 19  1  0
  5 20  1  0
  6 21  1  0
  6 22  1  0
  7 23  1  0
  7 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 12 31  1  0
 15 32  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1188                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       8.415  -2.695   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      11.082  -1.155   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0       8.415  -1.155   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       5.748  -1.155   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.748  -2.695   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.414  -0.385   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.414  -3.465   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.080  -1.155   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.080  -2.695   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.081  -0.385   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.081   1.155   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.415   1.925   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.748  -0.385   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.748   1.155   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.415   3.465   0.000  0.00  0.00           C+0
CONECT    1    3                                                            
CONECT    2   13                                                            
CONECT    3    1   10   13                                                  
CONECT    4    5    6   10                                                  
CONECT    5    4    7                                                       
CONECT    6    4    8                                                       
CONECT    7    5    9                                                       
CONECT    8    6    9                                                       
CONECT    9    7    8                                                       
CONECT   10    3    4   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   14   15                                                  
CONECT   13    2    3   14                                                  
CONECT   14   12   13                                                       
CONECT   15   12                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

COMPND    HMDB0015319
HETATM    1  C1  UNL     1      -2.889   2.257   0.792  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.408   0.876   0.542  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.080   0.587   0.327  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.655  -0.718   0.095  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.793  -1.022  -0.138  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.553  -0.769   1.103  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.342   0.483   1.184  1.00  0.00           C  
HETATM    8  C8  UNL     1       3.186   0.613  -0.063  1.00  0.00           C  
HETATM    9  C9  UNL     1       2.249   0.728  -1.228  1.00  0.00           C  
HETATM   10  C10 UNL     1       1.292  -0.381  -1.377  1.00  0.00           C  
HETATM   11  N1  UNL     1      -1.608  -1.667   0.094  1.00  0.00           N  
HETATM   12  O1  UNL     1      -1.174  -2.969  -0.139  1.00  0.00           O  
HETATM   13  C11 UNL     1      -2.915  -1.405   0.302  1.00  0.00           C  
HETATM   14  O2  UNL     1      -3.692  -2.404   0.271  1.00  0.00           O  
HETATM   15  C12 UNL     1      -3.340  -0.139   0.529  1.00  0.00           C  
HETATM   16  H1  UNL     1      -2.335   2.962   0.141  1.00  0.00           H  
HETATM   17  H2  UNL     1      -3.970   2.333   0.596  1.00  0.00           H  
HETATM   18  H3  UNL     1      -2.722   2.499   1.864  1.00  0.00           H  
HETATM   19  H4  UNL     1      -0.353   1.394   0.338  1.00  0.00           H  
HETATM   20  H5  UNL     1       0.824  -2.138  -0.313  1.00  0.00           H  
HETATM   21  H6  UNL     1       0.838  -0.770   1.979  1.00  0.00           H  
HETATM   22  H7  UNL     1       2.254  -1.622   1.346  1.00  0.00           H  
HETATM   23  H8  UNL     1       1.788   1.394   1.414  1.00  0.00           H  
HETATM   24  H9  UNL     1       3.080   0.359   2.032  1.00  0.00           H  
HETATM   25  H10 UNL     1       3.886  -0.223  -0.120  1.00  0.00           H  
HETATM   26  H11 UNL     1       3.754   1.563   0.016  1.00  0.00           H  
HETATM   27  H12 UNL     1       1.747   1.722  -1.156  1.00  0.00           H  
HETATM   28  H13 UNL     1       2.898   0.808  -2.150  1.00  0.00           H  
HETATM   29  H14 UNL     1       1.737  -1.124  -2.105  1.00  0.00           H  
HETATM   30  H15 UNL     1       0.394   0.016  -1.939  1.00  0.00           H  
HETATM   31  H16 UNL     1      -1.076  -3.273  -1.096  1.00  0.00           H  
HETATM   32  H17 UNL     1      -4.399   0.029   0.692  1.00  0.00           H  
CONECT    1    2   16   17   18
CONECT    2    3   15   15
CONECT    3    4    4   19
CONECT    4    5   11
CONECT    5    6   10   20
CONECT    6    7   21   22
CONECT    7    8   23   24
CONECT    8    9   25   26
CONECT    9   10   27   28
CONECT   10   29   30
CONECT   11   12   13
CONECT   12   31
CONECT   13   14   14   15
CONECT   15   32
END

HMDB0015319
     RDKit          3D
Ciclopirox
 32 33  0  0  0  0  0  0  0  0999 V2000
   -2.8888    2.2566    0.7917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4083    0.8756    0.5421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0802    0.5873    0.3269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6547   -0.7175    0.0949 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7930   -1.0222   -0.1376 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5533   -0.7686    1.1034 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3419    0.4831    1.1841 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1856    0.6132   -0.0625 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2488    0.7280   -1.2284 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2921   -0.3805   -1.3771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6078   -1.6670    0.0936 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1741   -2.9692   -0.1391 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9151   -1.4052    0.3024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6921   -2.4043    0.2711 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3401   -0.1389    0.5293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3347    2.9623    0.1414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9696    2.3327    0.5958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7216    2.4987    1.8642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3527    1.3938    0.3384 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8238   -2.1376   -0.3131 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8385   -0.7702    1.9792 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2540   -1.6215    1.3463 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7881    1.3944    1.4142 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0803    0.3585    2.0315 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8856   -0.2227   -0.1196 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7535    1.5630    0.0158 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7474    1.7221   -1.1562 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8983    0.8077   -2.1496 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7368   -1.1239   -2.1053 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3937    0.0159   -1.9394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0759   -3.2728   -1.0957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3988    0.0291    0.6924 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  4 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 13 15  1  0
 15  2  2  0
 10  5  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  3 19  1  0
  5 20  1  0
  6 21  1  0
  6 22  1  0
  7 23  1  0
  7 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 12 31  1  0
 15 32  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
6-Cyclohexyl-1-hydroxy-4-methyl-2(1H)-pyridinone	ChEBI
Ciclopiroxum	ChEBI
Loprox	Kegg
Penlac	Kegg
Ciclopirox olamin	HMDB
Ciclopirox-olamin	HMDB
Ciclopiroxolamine	HMDB
HOE 296b	HMDB
HOE-296b	HMDB
HOE 296	HMDB
Cyclopirox	HMDB
Cyclopyroxolamine	HMDB
Batrafen	HMDB
Dafnegin-CSC	HMDB
Ciclopirox olamine	HMDB
6-Cyclohexyl-1-hydroxy-4-methyl-2(1H)-pyridone ethanolamine salt	HMDB
HOE-296	HMDB
Dafnegin CSC	HMDB

Chemical Formula

C₁₂H₁₇NO₂

Average Molecular Weight

207.2689

Monoisotopic Molecular Weight

207.125928793

IUPAC Name

6-cyclohexyl-1-hydroxy-4-methyl-1,2-dihydropyridin-2-one

Traditional Name

penlac

CAS Registry Number

29342-05-0

SMILES

CC1=CC(=O)N(O)C(=C1)C1CCCCC1

InChI Identifier

InChI=1S/C12H17NO2/c1-9-7-11(13(15)12(14)8-9)10-5-3-2-4-6-10/h7-8,10,15H,2-6H2,1H3

InChI Key

SCKYRAXSEDYPSA-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyridinones. Pyridinones are compounds containing a pyridine ring, which bears a ketone.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyridines and derivatives

Sub Class

Hydropyridines

Direct Parent

Pyridinones

Alternative Parents

Substituents

Methylpyridine
Pyridinone
Dihydropyridine
Heteroaromatic compound
Lactam
Azacycle
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

hydroxypyridone antifungal drug (CHEBI:453011 )
pyridone (CHEBI:453011 )
cyclic hydroxamic acid (CHEBI:453011 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0015319)

Source

Exogenous

Exogenous (HMDB: HMDB0015319)

Process

Not Available

Role

Industrial application

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	144 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	1.41 g/L	Not Available
LogP	2.3	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.41 g/L	ALOGPS
logP	2.15	ALOGPS
logP	2.22	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	6.84	ChemAxon
pKa (Strongest Basic)	-6.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	40.54 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	60.91 m³·mol⁻¹	ChemAxon
Polarizability	23.12 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	147.395	31661259
DarkChem	[M-H]-	144.123	31661259
DeepCCS	[M+H]+	148.109	30932474
DeepCCS	[M-H]-	145.714	30932474
DeepCCS	[M-2H]-	179.385	30932474
DeepCCS	[M+Na]+	154.145	30932474
AllCCS	[M+H]+	146.8	32859911
AllCCS	[M+H-H2O]+	142.6	32859911
AllCCS	[M+NH4]+	150.8	32859911
AllCCS	[M+Na]+	151.9	32859911
AllCCS	[M-H]-	152.0	32859911
AllCCS	[M+Na-2H]-	152.4	32859911
AllCCS	[M+HCOO]-	152.9	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	4.88 minutes	32390414
Predicted by Siyang on May 30, 2022	10.6691 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.82 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1376.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	269.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	142.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	169.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	211.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	415.5 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	314.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	181.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	897.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	400.8 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1136.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	266.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	288.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	494.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	193.2 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	247.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Ciclopirox	CC1=CC(=O)N(O)C(=C1)C1CCCCC1	2234.0	Standard polar	33892256
Ciclopirox	CC1=CC(=O)N(O)C(=C1)C1CCCCC1	1849.6	Standard non polar	33892256
Ciclopirox	CC1=CC(=O)N(O)C(=C1)C1CCCCC1	1869.0	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 - Ciclopirox GC-MS (Non-derivatized) - 70eV, Positive	splash10-02vi-1900000000-b0302ddc025a747a3484	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ciclopirox 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 - Ciclopirox 10V, Positive-QTOF	splash10-0a4i-0390000000-1d9227c74bcc86583df3	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ciclopirox 20V, Positive-QTOF	splash10-0a4i-2690000000-963d9e37afedc3b4a600	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ciclopirox 40V, Positive-QTOF	splash10-05mo-9600000000-de9b944829cc25a5681b	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ciclopirox 10V, Negative-QTOF	splash10-0a4i-3090000000-ac55f8f5496920dc9ca4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ciclopirox 20V, Negative-QTOF	splash10-0a4i-0490000000-6cd8e595360c6bddf33a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ciclopirox 40V, Negative-QTOF	splash10-0a6r-5900000000-7869913422c2e64d2101	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ciclopirox 10V, Positive-QTOF	splash10-0a4i-0090000000-69c98b0c95a4f7a6ef58	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ciclopirox 20V, Positive-QTOF	splash10-0a4i-4490000000-d28507b6dbcfe8f98141	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ciclopirox 40V, Positive-QTOF	splash10-066r-9700000000-4dafee1a9eed2bbabe7b	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ciclopirox 10V, Negative-QTOF	splash10-0a4i-0090000000-bc1578d935014f0ac50f	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ciclopirox 20V, Negative-QTOF	splash10-05is-6930000000-c7140620c24b41758ee7	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ciclopirox 40V, Negative-QTOF	splash10-0f6x-9400000000-8c3e2f33da6d3911ea34	2021-10-11	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01188	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01188	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01188

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2647

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Ciclopirox

METLIN ID

Not Available

PubChem Compound

2749

PDB ID

Not Available

ChEBI ID

453011

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

Niewerth M, Kunze D, Seibold M, Schaller M, Korting HC, Hube B: Ciclopirox olamine treatment affects the expression pattern of Candida albicans genes encoding virulence factors, iron metabolism proteins, and drug resistance factors. Antimicrob Agents Chemother. 2003 Jun;47(6):1805-17. [PubMed:12760852 ]
Sigle HC, Thewes S, Niewerth M, Korting HC, Schafer-Korting M, Hube B: Oxygen accessibility and iron levels are critical factors for the antifungal action of ciclopirox against Candida albicans. J Antimicrob Chemother. 2005 May;55(5):663-73. Epub 2005 Mar 24. [PubMed:15790671 ]
Qadripur SA: [Antimycotic therapy. 2. Antimycotic chemotherapeutic agents: imidazole derivatives, tolciclate, haloprogin, ciclopiroxolamin]. Fortschr Med. 1983 Mar 10;101(9):355-63. [PubMed:6303928 ]
Beikert FC, Le MT, Koeninger A, Technau K, Clad A: Recurrent vulvovaginal candidosis: focus on the vulva. Mycoses. 2011 Nov;54(6):e807-10. doi: 10.1111/j.1439-0507.2011.02030.x. Epub 2011 May 25. [PubMed:21615545 ]

Showing metabocard for Ciclopirox (HMDB0015319)

MOL for HMDB0015319 (Ciclopirox)

3D MOL for HMDB0015319 (Ciclopirox)

3D SDF for HMDB0015319 (Ciclopirox)

3D-SDF for HMDB0015319 (Ciclopirox)

PDB for HMDB0015319 (Ciclopirox)

3D PDB for HMDB0015319 (Ciclopirox)

SMILES for HMDB0015319 (Ciclopirox)

INCHI for HMDB0015319 (Ciclopirox)

Structure for HMDB0015319 (Ciclopirox)

3D Structure for HMDB0015319 (Ciclopirox)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra