Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2) Show 2 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2022-03-07 02:51:46 UTC

HMDB ID

HMDB0014862

Secondary Accession Numbers

HMDB14862

Metabolite Identification

Common Name

Imiquimod

Description

Imiquimod is an immune response modifier that acts as a toll-like receptor 7 agonist. Imiquimod is commonly used topically to treat warts on the skin of the genital and anal areas. Imiquimod does not cure warts, and new warts may appear during treatment. Imiquimod does not fight the viruses that cause warts directly, however, it does help to relieve and control wart production. miquimod is also used to treat a skin condition of the face and scalp called actinic keratoses and certain types of skin cancer called superficial basal cell carcinoma.

Structure

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

HMDB0014862
     RDKit          3D
Imiquimod
 34 36  0  0  0  0  0  0  0  0999 V2000
    3.2786    0.3388    0.8347 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3882   -0.7624    0.3166 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3102   -1.9289   -0.0393 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6018   -0.4215   -0.8786 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6770    0.6631   -0.8050 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0102    1.9525   -1.1723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0375    2.7396   -1.0327 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0744    2.0372   -0.5832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3713    2.3362   -0.2709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8014    3.6873   -0.4316 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2216    1.4116    0.1704 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8031    0.1380    0.3190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6873   -0.8171    0.7858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2749   -2.1185    0.9514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0005   -2.5014    0.6650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0946   -1.5517    0.1928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5089   -0.2569    0.0278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6107    0.7210   -0.4408 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9276    0.6889    0.0130 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9657   -0.1424    1.5738 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7439    1.1244    1.3642 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7691   -1.0878    1.1767 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6545   -2.8224   -0.1343 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8304   -1.6867   -0.9825 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0206   -2.0632    0.7980 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1955   -1.2991   -1.3641 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4196   -0.1175   -1.6722 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0242    2.2309   -1.5236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5647    3.8899   -1.1173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3417    4.4321    0.1394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6929   -0.5542    1.0207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9600   -2.8790    1.3172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6591   -3.5049    0.7863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1125   -1.8759   -0.0046 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18  5  1  0
 18  8  1  0
 17 12  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  6 28  1  0
 10 29  1  0
 10 30  1  0
 13 31  1  0
 14 32  1  0
 15 33  1  0
 16 34  1  0
M  END

724
  Mrv0541 02231214572D          

 18 20  0  0  0  0            999 V2000
    3.2646    0.4156    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2646   -0.9122    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4742   -0.6608    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7597   -1.8983    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0082    1.1998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2010    1.3699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0452    0.1642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7597    0.5767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0452   -0.6608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7831   -0.2483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.7559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9447    2.1541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4742    0.1642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7597   -1.0733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7464    1.4359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2249    0.5823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4873    1.8714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2315    1.4416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  1  0  0  0  0
  1  7  1  0  0  0  0
  1 10  1  0  0  0  0
  2  9  1  0  0  0  0
  2 10  2  0  0  0  0
  3 13  1  0  0  0  0
  3 14  2  0  0  0  0
  4 14  1  0  0  0  0
  5  6  1  0  0  0  0
  6 11  1  0  0  0  0
  6 12  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  8 13  1  0  0  0  0
  8 15  2  0  0  0  0
  9 14  1  0  0  0  0
 13 16  2  0  0  0  0
 15 17  1  0  0  0  0
 16 18  1  0  0  0  0
 17 18  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014862

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)CN1C=NC2=C1C1=CC=CC=C1N=C2N

> <INCHI_IDENTIFIER>
InChI=1S/C14H16N4/c1-9(2)7-18-8-16-12-13(18)10-5-3-4-6-11(10)17-14(12)15/h3-6,8-9H,7H2,1-2H3,(H2,15,17)

> <INCHI_KEY>
DOUYETYNHWVLEO-UHFFFAOYSA-N

> <FORMULA>
C14H16N4

> <MOLECULAR_WEIGHT>
240.3036

> <EXACT_MASS>
240.137496532

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
26.667390856253917

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine

> <ALOGPS_LOGP>
2.83

> <JCHEM_LOGP>
2.6506694719999997

> <ALOGPS_LOGS>
-2.99

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
5.397918887205608

> <JCHEM_POLAR_SURFACE_AREA>
56.730000000000004

> <JCHEM_REFRACTIVITY>
72.5446

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.47e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
imiquimod

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014862
     RDKit          3D
Imiquimod
 34 36  0  0  0  0  0  0  0  0999 V2000
    3.2786    0.3388    0.8347 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3882   -0.7624    0.3166 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3102   -1.9289   -0.0393 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6018   -0.4215   -0.8786 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6770    0.6631   -0.8050 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0102    1.9525   -1.1723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0375    2.7396   -1.0327 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0744    2.0372   -0.5832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3713    2.3362   -0.2709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8014    3.6873   -0.4316 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2216    1.4116    0.1704 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8031    0.1380    0.3190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6873   -0.8171    0.7858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2749   -2.1185    0.9514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0005   -2.5014    0.6650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0946   -1.5517    0.1928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5089   -0.2569    0.0278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6107    0.7210   -0.4408 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9276    0.6889    0.0130 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9657   -0.1424    1.5738 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7439    1.1244    1.3642 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7691   -1.0878    1.1767 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6545   -2.8224   -0.1343 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8304   -1.6867   -0.9825 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0206   -2.0632    0.7980 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1955   -1.2991   -1.3641 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4196   -0.1175   -1.6722 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0242    2.2309   -1.5236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5647    3.8899   -1.1173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3417    4.4321    0.1394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6929   -0.5542    1.0207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9600   -2.8790    1.3172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6591   -3.5049    0.7863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1125   -1.8759   -0.0046 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18  5  1  0
 18  8  1  0
 17 12  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  6 28  1  0
 10 29  1  0
 10 30  1  0
 13 31  1  0
 14 32  1  0
 15 33  1  0
 16 34  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 724                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  N   UNK     0       6.094   0.776   0.000  0.00  0.00           N+0
HETATM    2  N   UNK     0       6.094  -1.703   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0      10.219  -1.233   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0       8.885  -3.543   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       5.615   2.240   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.109   2.557   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.551   0.307   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.885   1.077   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.551  -1.233   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.195  -0.463   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.080   1.411   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.630   4.021   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.219   0.307   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.885  -2.003   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.860   2.680   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.620   1.087   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.243   3.493   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.632   2.691   0.000  0.00  0.00           C+0
CONECT    1    5    7   10                                                  
CONECT    2    9   10                                                       
CONECT    3   13   14                                                       
CONECT    4   14                                                            
CONECT    5    1    6                                                       
CONECT    6    5   11   12                                                  
CONECT    7    1    8    9                                                  
CONECT    8    7   13   15                                                  
CONECT    9    2    7   14                                                  
CONECT   10    1    2                                                       
CONECT   11    6                                                            
CONECT   12    6                                                            
CONECT   13    3    8   16                                                  
CONECT   14    3    4    9                                                  
CONECT   15    8   17                                                       
CONECT   16   13   18                                                       
CONECT   17   15   18                                                       
CONECT   18   16   17                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   40    0
END

COMPND    HMDB0014862
HETATM    1  C1  UNL     1       3.279   0.339   0.835  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.388  -0.762   0.317  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.310  -1.929  -0.039  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.602  -0.422  -0.879  1.00  0.00           C  
HETATM    5  N1  UNL     1       0.677   0.663  -0.805  1.00  0.00           N  
HETATM    6  C5  UNL     1       1.010   1.953  -1.172  1.00  0.00           C  
HETATM    7  N2  UNL     1      -0.037   2.740  -1.033  1.00  0.00           N  
HETATM    8  C6  UNL     1      -1.074   2.037  -0.583  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.371   2.336  -0.271  1.00  0.00           C  
HETATM   10  N3  UNL     1      -2.801   3.687  -0.432  1.00  0.00           N  
HETATM   11  N4  UNL     1      -3.222   1.412   0.170  1.00  0.00           N  
HETATM   12  C8  UNL     1      -2.803   0.138   0.319  1.00  0.00           C  
HETATM   13  C9  UNL     1      -3.687  -0.817   0.786  1.00  0.00           C  
HETATM   14  C10 UNL     1      -3.275  -2.119   0.951  1.00  0.00           C  
HETATM   15  C11 UNL     1      -2.001  -2.501   0.665  1.00  0.00           C  
HETATM   16  C12 UNL     1      -1.095  -1.552   0.193  1.00  0.00           C  
HETATM   17  C13 UNL     1      -1.509  -0.257   0.028  1.00  0.00           C  
HETATM   18  C14 UNL     1      -0.611   0.721  -0.441  1.00  0.00           C  
HETATM   19  H1  UNL     1       3.928   0.689   0.013  1.00  0.00           H  
HETATM   20  H2  UNL     1       3.966  -0.142   1.574  1.00  0.00           H  
HETATM   21  H3  UNL     1       2.744   1.124   1.364  1.00  0.00           H  
HETATM   22  H4  UNL     1       1.769  -1.088   1.177  1.00  0.00           H  
HETATM   23  H5  UNL     1       2.655  -2.822  -0.134  1.00  0.00           H  
HETATM   24  H6  UNL     1       3.830  -1.687  -0.982  1.00  0.00           H  
HETATM   25  H7  UNL     1       4.021  -2.063   0.798  1.00  0.00           H  
HETATM   26  H8  UNL     1       1.195  -1.299  -1.364  1.00  0.00           H  
HETATM   27  H9  UNL     1       2.420  -0.118  -1.672  1.00  0.00           H  
HETATM   28  H10 UNL     1       2.024   2.231  -1.524  1.00  0.00           H  
HETATM   29  H11 UNL     1      -3.565   3.890  -1.117  1.00  0.00           H  
HETATM   30  H12 UNL     1      -2.342   4.432   0.139  1.00  0.00           H  
HETATM   31  H13 UNL     1      -4.693  -0.554   1.021  1.00  0.00           H  
HETATM   32  H14 UNL     1      -3.960  -2.879   1.317  1.00  0.00           H  
HETATM   33  H15 UNL     1      -1.659  -3.505   0.786  1.00  0.00           H  
HETATM   34  H16 UNL     1      -0.112  -1.876  -0.005  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3    4   22
CONECT    3   23   24   25
CONECT    4    5   26   27
CONECT    5    6   18
CONECT    6    7    7   28
CONECT    7    8
CONECT    8    9    9   18
CONECT    9   10   11
CONECT   10   29   30
CONECT   11   12   12
CONECT   12   13   17
CONECT   13   14   14   31
CONECT   14   15   32
CONECT   15   16   16   33
CONECT   16   17   34
CONECT   17   18   18
END

HMDB0014862
     RDKit          3D
Imiquimod
 34 36  0  0  0  0  0  0  0  0999 V2000
    3.2786    0.3388    0.8347 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3882   -0.7624    0.3166 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3102   -1.9289   -0.0393 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6018   -0.4215   -0.8786 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6770    0.6631   -0.8050 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0102    1.9525   -1.1723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0375    2.7396   -1.0327 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0744    2.0372   -0.5832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3713    2.3362   -0.2709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8014    3.6873   -0.4316 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2216    1.4116    0.1704 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8031    0.1380    0.3190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6873   -0.8171    0.7858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2749   -2.1185    0.9514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0005   -2.5014    0.6650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0946   -1.5517    0.1928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5089   -0.2569    0.0278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6107    0.7210   -0.4408 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9276    0.6889    0.0130 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9657   -0.1424    1.5738 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7439    1.1244    1.3642 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7691   -1.0878    1.1767 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6545   -2.8224   -0.1343 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8304   -1.6867   -0.9825 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0206   -2.0632    0.7980 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1955   -1.2991   -1.3641 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4196   -0.1175   -1.6722 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0242    2.2309   -1.5236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5647    3.8899   -1.1173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3417    4.4321    0.1394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6929   -0.5542    1.0207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9600   -2.8790    1.3172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6591   -3.5049    0.7863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1125   -1.8759   -0.0046 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18  5  1  0
 18  8  1  0
 17 12  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  6 28  1  0
 10 29  1  0
 10 30  1  0
 13 31  1  0
 14 32  1  0
 15 33  1  0
 16 34  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-Isobutyl-1H-imidazo[4,5-c]quinolin-4-amine	ChEBI
4-Amino-1-isobutyl-1H-imidazo(4,5-c)quinoline	ChEBI
Imiquimodum	ChEBI
R 837	ChEBI
Aldara	Kegg
Zyclara	Kegg
Imiquimod acetate	HMDB
1-Isobutyl-1H-imidazo(4,5-c)quinolin-4-amine	HMDB

Chemical Formula

C₁₄H₁₆N₄

Average Molecular Weight

240.3036

Monoisotopic Molecular Weight

240.137496532

IUPAC Name

1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine

Traditional Name

imiquimod

CAS Registry Number

99011-02-6

SMILES

CC(C)CN1C=NC2=C1C1=CC=CC=C1N=C2N

InChI Identifier

InChI=1S/C14H16N4/c1-9(2)7-18-8-16-12-13(18)10-5-3-4-6-11(10)17-14(12)15/h3-6,8-9H,7H2,1-2H3,(H2,15,17)

InChI Key

DOUYETYNHWVLEO-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as imidazoquinolines. These are aromatic heterocyclic compounds containing an imidazole ring fused to a quinoline ring system. In some configurations, the imidazole ring shares a nitrogen atom with the quinoline moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Imidazoquinolines

Direct Parent

Imidazoquinolines

Alternative Parents

Substituents

Imidazoquinoline
Aminoquinoline
Imidazopyridine
Imidazo-[4,5-c]pyridine
Aminopyridine
N-substituted imidazole
Pyridine
Imidolactam
Benzenoid
Azole
Imidazole
Heteroaromatic compound
Azacycle
Organopnictogen compound
Hydrocarbon derivative
Organic nitrogen compound
Amine
Organonitrogen compound
Primary amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

imidazoquinoline (CHEBI:36704 )

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: HMDB0014862)

Source

Exogenous

Exogenous (HMDB: HMDB0014862)

Process

Naturally occurring process

Biological process

Biochemical pathway

Protein pathway

Toll-Like Receptor Pathway 2 (PathBank: SMP0120937)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	292 - 294 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.25 g/L	Not Available
LogP	2.7	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.25 g/L	ALOGPS
logP	2.83	ALOGPS
logP	2.65	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Basic)	5.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	56.73 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	72.54 m³·mol⁻¹	ChemAxon
Polarizability	26.67 Å³	ChemAxon
Number of Rings	3	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]+	154.511	31661259
DarkChem	[M-H]-	156.036	31661259
DeepCCS	[M+H]+	150.099	30932474
DeepCCS	[M-H]-	147.741	30932474
DeepCCS	[M-2H]-	181.171	30932474
DeepCCS	[M+Na]+	156.265	30932474
AllCCS	[M+H]+	154.9	32859911
AllCCS	[M+H-H2O]+	151.0	32859911
AllCCS	[M+NH4]+	158.5	32859911
AllCCS	[M+Na]+	159.5	32859911
AllCCS	[M-H]-	161.4	32859911
AllCCS	[M+Na-2H]-	161.1	32859911
AllCCS	[M+HCOO]-	160.9	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.	3.18 minutes	32390414
Predicted by Siyang on May 30, 2022	10.5736 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.47 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	34.8 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1801.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	275.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	123.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	172.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	150.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	371.5 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	335.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	95.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	713.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	353.9 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	1097.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	210.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	288.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	346.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	215.5 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	8.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Imiquimod	CC(C)CN1C=NC2=C1C1=CC=CC=C1N=C2N	3104.7	Standard polar	33892256
Imiquimod	CC(C)CN1C=NC2=C1C1=CC=CC=C1N=C2N	2207.7	Standard non polar	33892256
Imiquimod	CC(C)CN1C=NC2=C1C1=CC=CC=C1N=C2N	2382.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Imiquimod,1TMS,isomer #1	CC(C)CN1C=NC2=C(N[Si](C)(C)C)N=C3C=CC=CC3=C21	2471.4	Semi standard non polar	33892256
Imiquimod,1TMS,isomer #1	CC(C)CN1C=NC2=C(N[Si](C)(C)C)N=C3C=CC=CC3=C21	2310.7	Standard non polar	33892256
Imiquimod,1TMS,isomer #1	CC(C)CN1C=NC2=C(N[Si](C)(C)C)N=C3C=CC=CC3=C21	3176.9	Standard polar	33892256
Imiquimod,2TMS,isomer #1	CC(C)CN1C=NC2=C(N([Si](C)(C)C)[Si](C)(C)C)N=C3C=CC=CC3=C21	2434.4	Semi standard non polar	33892256
Imiquimod,2TMS,isomer #1	CC(C)CN1C=NC2=C(N([Si](C)(C)C)[Si](C)(C)C)N=C3C=CC=CC3=C21	2441.4	Standard non polar	33892256
Imiquimod,2TMS,isomer #1	CC(C)CN1C=NC2=C(N([Si](C)(C)C)[Si](C)(C)C)N=C3C=CC=CC3=C21	2838.5	Standard polar	33892256
Imiquimod,1TBDMS,isomer #1	CC(C)CN1C=NC2=C(N[Si](C)(C)C(C)(C)C)N=C3C=CC=CC3=C21	2673.7	Semi standard non polar	33892256
Imiquimod,1TBDMS,isomer #1	CC(C)CN1C=NC2=C(N[Si](C)(C)C(C)(C)C)N=C3C=CC=CC3=C21	2513.9	Standard non polar	33892256
Imiquimod,1TBDMS,isomer #1	CC(C)CN1C=NC2=C(N[Si](C)(C)C(C)(C)C)N=C3C=CC=CC3=C21	3259.7	Standard polar	33892256
Imiquimod,2TBDMS,isomer #1	CC(C)CN1C=NC2=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=C3C=CC=CC3=C21	2823.5	Semi standard non polar	33892256
Imiquimod,2TBDMS,isomer #1	CC(C)CN1C=NC2=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=C3C=CC=CC3=C21	2825.6	Standard non polar	33892256
Imiquimod,2TBDMS,isomer #1	CC(C)CN1C=NC2=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=C3C=CC=CC3=C21	2992.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Imiquimod GC-MS (Non-derivatized) - 70eV, Positive	splash10-0c04-3940000000-1662afa92a44e20e76ba	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Imiquimod 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Imiquimod , positive-QTOF	splash10-000f-2970000000-08cb009f804dd3b43f69	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Imiquimod , positive-QTOF	splash10-000i-2910000000-58faefee0903c8967370	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Imiquimod 10V, Positive-QTOF	splash10-0006-2090000000-6f9d6e2f4d7747ae95db	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Imiquimod 20V, Positive-QTOF	splash10-0a4l-9580000000-d31c7988dbae6085a29d	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Imiquimod 40V, Positive-QTOF	splash10-0a4i-9400000000-503227ffe338b6a8d185	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Imiquimod 10V, Negative-QTOF	splash10-000i-0390000000-44a8c5b2ac2cd485d2f2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Imiquimod 20V, Negative-QTOF	splash10-001i-0940000000-5f1b9952a672997a0b4e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Imiquimod 40V, Negative-QTOF	splash10-001i-0900000000-d71208eb00e043d7e84f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Imiquimod 10V, Positive-QTOF	splash10-0006-0390000000-d88591b18aaba14469cd	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Imiquimod 20V, Positive-QTOF	splash10-000f-0690000000-71a9a845a947ea2d2862	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Imiquimod 40V, Positive-QTOF	splash10-05as-0910000000-a9b321d2938173c4f73f	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Imiquimod 10V, Negative-QTOF	splash10-000i-0090000000-7474f6fc851ae052786c	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Imiquimod 20V, Negative-QTOF	splash10-000i-0090000000-d514bde35ff30a0c785c	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Imiquimod 40V, Negative-QTOF	splash10-001i-0910000000-946992964c1e54432a88	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

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 DB00724	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00724	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00724

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

51809

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Imiquimod

METLIN ID

Not Available

PubChem Compound

57469

PDB ID

Not Available

ChEBI ID

36704

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

Miller RL, Gerster JF, Owens ML, Slade HB, Tomai MA: Imiquimod applied topically: a novel immune response modifier and new class of drug. Int J Immunopharmacol. 1999 Jan;21(1):1-14. [PubMed:10411278 ]
Hemmi H, Kaisho T, Takeuchi O, Sato S, Sanjo H, Hoshino K, Horiuchi T, Tomizawa H, Takeda K, Akira S: Small anti-viral compounds activate immune cells via the TLR7 MyD88-dependent signaling pathway. Nat Immunol. 2002 Feb;3(2):196-200. Epub 2002 Jan 22. [PubMed:11812998 ]
Bilu D, Sauder DN: Imiquimod: modes of action. Br J Dermatol. 2003 Nov;149 Suppl 66:5-8. [PubMed:14616337 ]
van Egmond S, Hoedemaker C, Sinclair R: Successful treatment of perianal Bowen's disease with imiquimod. Int J Dermatol. 2007 Mar;46(3):318-9. [PubMed:17343595 ]
3M [Link]

Enzymes

Enzyme Details

1. Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

2. Cytochrome P450 1A2

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:: CYP1A2
Uniprot ID:: P05177
Molecular weight:: 58406.915

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Showing metabocard for Imiquimod (HMDB0014862)

MOL for HMDB0014862 (Imiquimod)

3D MOL for HMDB0014862 (Imiquimod)

3D SDF for HMDB0014862 (Imiquimod)

3D-SDF for HMDB0014862 (Imiquimod)

PDB for HMDB0014862 (Imiquimod)

3D PDB for HMDB0014862 (Imiquimod)

SMILES for HMDB0014862 (Imiquimod)

INCHI for HMDB0014862 (Imiquimod)

Structure for HMDB0014862 (Imiquimod)

3D Structure for HMDB0014862 (Imiquimod)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References