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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

2022-03-07 02:51:52 UTC

HMDB ID

HMDB0015141

Secondary Accession Numbers

HMDB15141

Metabolite Identification

Common Name

Letrozole

Description

Letrozole, also known as femara, belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups. Letrozole is a moderately basic compound (based on its pKa). Letrozole is a potentially toxic compound. However, letrozole is effective only in post-menopausal women, in whom estrogen is produced predominantly in peripheral tissues (i.e. in adipose tissue, like that of the breast) and a number of sites in the brain. A study of 150 babies following treatment with letrozole or letrozole and gonadotropins presented at the American Society of Reproductive Medicine 2005 Conference found no difference in overall abnormalities but did find a significantly higher rate of locomotor and cardiac abnormalities among the group having taken letrozole compared to natural conception. Generally, side effects include signs and symptoms of hypoestrogenism. When used in combination with growth hormone, letrozole has been shown effective in one adolescent boy with a short stature. A larger, follow-up study with 911 babies compared those born following treatment with letrozole to those born following treatment with clomiphene.

Structure

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

HMDB0015141
     RDKit          3D
Letrozole
 33 35  0  0  0  0  0  0  0  0999 V2000
   -5.9417    2.2160   -0.4993 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8957    1.7084   -0.5304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5977    1.0913   -0.5771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1707    0.2392    0.4377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9176   -0.3306    0.3515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0843   -0.0769   -0.7101 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2694   -0.7042   -0.7845 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2808    0.1439   -0.1367 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5687    0.0017    1.1997 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5286    0.8014    1.8308 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1894    1.7570    1.0490 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1806    2.5792    1.7113 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9729    3.2317    2.2493 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9060    1.9049   -0.2902 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9418    1.0894   -0.8872 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2531   -2.0639   -0.2559 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2454   -2.7479    0.3411 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7271   -3.9454    0.6398 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5557   -4.0226    0.2456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8324   -2.8337   -0.3129 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5133    0.7669   -1.7102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7537    1.3382   -1.6363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8513    0.0714    1.2423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5885   -0.9966    1.1484 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5160   -0.7815   -1.8718 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0787   -0.7248    1.8330 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7589    0.6933    2.8827 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4175    2.6413   -0.8855 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7393    1.2320   -1.9549 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2404   -2.3671    0.5209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1950   -4.8952    0.3766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8532    0.9738   -2.5605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0639    2.0092   -2.4561 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  3  0
 11 14  1  0
 14 15  2  0
  7 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
  6 21  1  0
 21 22  2  0
 22  3  1  0
 15  8  1  0
 20 16  1  0
  4 23  1  0
  5 24  1  0
  7 25  1  0
  9 26  1  0
 10 27  1  0
 14 28  1  0
 15 29  1  0
 17 30  1  0
 19 31  1  0
 21 32  1  0
 22 33  1  0
M  END

1006
  Mrv0541 02231215102D          

 22 24  0  0  0  0            999 V2000
    2.9558    1.4438    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8695    2.2643    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    1.7213    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6703   -3.0938    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2427    3.0938    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6703    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6703    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3847    1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9558   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0993    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3847   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3847    2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2021    1.1082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9558   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8137    1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3847   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0993    2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6703   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8137    2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    2.4358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6703   -2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5282    2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  1 13  1  0  0  0  0
  2 20  2  0  0  0  0
  3 13  2  0  0  0  0
  3 20  1  0  0  0  0
  4 21  3  0  0  0  0
  5 22  3  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  7  9  2  0  0  0  0
  7 11  1  0  0  0  0
  8 10  2  0  0  0  0
  8 12  1  0  0  0  0
  9 14  1  0  0  0  0
 10 15  1  0  0  0  0
 11 16  2  0  0  0  0
 12 17  2  0  0  0  0
 14 18  2  0  0  0  0
 15 19  2  0  0  0  0
 16 18  1  0  0  0  0
 17 19  1  0  0  0  0
 18 21  1  0  0  0  0
 19 22  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015141

> <DATABASE_NAME>
hmdb

> <SMILES>
N#CC1=CC=C(C=C1)C(N1C=NC=N1)C1=CC=C(C=C1)C#N

> <INCHI_IDENTIFIER>
InChI=1S/C17H11N5/c18-9-13-1-5-15(6-2-13)17(22-12-20-11-21-22)16-7-3-14(10-19)4-8-16/h1-8,11-12,17H

> <INCHI_KEY>
HPJKCIUCZWXJDR-UHFFFAOYSA-N

> <FORMULA>
C17H11N5

> <MOLECULAR_WEIGHT>
285.3027

> <EXACT_MASS>
285.101445377

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
29.58909479310946

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-[(4-cyanophenyl)(1H-1,2,4-triazol-1-yl)methyl]benzonitrile

> <ALOGPS_LOGP>
1.86

> <JCHEM_LOGP>
2.9354919133333333

> <ALOGPS_LOGS>
-3.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
2.1733026282717627

> <JCHEM_POLAR_SURFACE_AREA>
78.28999999999999

> <JCHEM_REFRACTIVITY>
94.4741

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.99e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
letrozole

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015141
     RDKit          3D
Letrozole
 33 35  0  0  0  0  0  0  0  0999 V2000
   -5.9417    2.2160   -0.4993 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8957    1.7084   -0.5304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5977    1.0913   -0.5771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1707    0.2392    0.4377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9176   -0.3306    0.3515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0843   -0.0769   -0.7101 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2694   -0.7042   -0.7845 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2808    0.1439   -0.1367 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5687    0.0017    1.1997 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5286    0.8014    1.8308 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1894    1.7570    1.0490 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1806    2.5792    1.7113 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9729    3.2317    2.2493 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9060    1.9049   -0.2902 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9418    1.0894   -0.8872 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2531   -2.0639   -0.2559 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2454   -2.7479    0.3411 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7271   -3.9454    0.6398 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5557   -4.0226    0.2456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8324   -2.8337   -0.3129 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5133    0.7669   -1.7102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7537    1.3382   -1.6363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8513    0.0714    1.2423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5885   -0.9966    1.1484 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5160   -0.7815   -1.8718 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0787   -0.7248    1.8330 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7589    0.6933    2.8827 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4175    2.6413   -0.8855 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7393    1.2320   -1.9549 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2404   -2.3671    0.5209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1950   -4.8952    0.3766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8532    0.9738   -2.5605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0639    2.0092   -2.4561 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  3  0
 11 14  1  0
 14 15  2  0
  7 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
  6 21  1  0
 21 22  2  0
 22  3  1  0
 15  8  1  0
 20 16  1  0
  4 23  1  0
  5 24  1  0
  7 25  1  0
  9 26  1  0
 10 27  1  0
 14 28  1  0
 15 29  1  0
 17 30  1  0
 19 31  1  0
 21 32  1  0
 22 33  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1006                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  N   UNK     0       5.517   2.695   0.000  0.00  0.00           N+0
HETATM    2  N   UNK     0       5.356   4.227   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0       3.080   3.213   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0       6.851  -5.775   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0      13.520   5.775   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       6.851   1.925   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.851   0.385   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.185   2.695   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.517  -0.385   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.519   1.925   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.185  -0.385   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.185   4.235   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.111   2.069   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.517  -1.925   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.852   2.695   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.185  -1.925   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.519   5.005   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.851  -2.695   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.852   4.235   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.850   4.547   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.851  -4.235   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      12.186   5.005   0.000  0.00  0.00           C+0
CONECT    1    2    6   13                                                  
CONECT    2    1   20                                                       
CONECT    3   13   20                                                       
CONECT    4   21                                                            
CONECT    5   22                                                            
CONECT    6    1    7    8                                                  
CONECT    7    6    9   11                                                  
CONECT    8    6   10   12                                                  
CONECT    9    7   14                                                       
CONECT   10    8   15                                                       
CONECT   11    7   16                                                       
CONECT   12    8   17                                                       
CONECT   13    1    3                                                       
CONECT   14    9   18                                                       
CONECT   15   10   19                                                       
CONECT   16   11   18                                                       
CONECT   17   12   19                                                       
CONECT   18   14   16   21                                                  
CONECT   19   15   17   22                                                  
CONECT   20    2    3                                                       
CONECT   21    4   18                                                       
CONECT   22    5   19                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

COMPND    HMDB0015141
HETATM    1  N1  UNL     1      -5.942   2.216  -0.499  1.00  0.00           N  
HETATM    2  C1  UNL     1      -4.896   1.708  -0.530  1.00  0.00           C  
HETATM    3  C2  UNL     1      -3.598   1.091  -0.577  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.171   0.239   0.438  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.918  -0.331   0.351  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.084  -0.077  -0.710  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.269  -0.704  -0.785  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.281   0.144  -0.137  1.00  0.00           C  
HETATM    9  C8  UNL     1       1.569   0.002   1.200  1.00  0.00           C  
HETATM   10  C9  UNL     1       2.529   0.801   1.831  1.00  0.00           C  
HETATM   11  C10 UNL     1       3.189   1.757   1.049  1.00  0.00           C  
HETATM   12  C11 UNL     1       4.181   2.579   1.711  1.00  0.00           C  
HETATM   13  N2  UNL     1       4.973   3.232   2.249  1.00  0.00           N  
HETATM   14  C12 UNL     1       2.906   1.905  -0.290  1.00  0.00           C  
HETATM   15  C13 UNL     1       1.942   1.089  -0.887  1.00  0.00           C  
HETATM   16  N3  UNL     1       0.253  -2.064  -0.256  1.00  0.00           N  
HETATM   17  C14 UNL     1       1.245  -2.748   0.341  1.00  0.00           C  
HETATM   18  N4  UNL     1       0.727  -3.945   0.640  1.00  0.00           N  
HETATM   19  C15 UNL     1      -0.556  -4.023   0.246  1.00  0.00           C  
HETATM   20  N5  UNL     1      -0.832  -2.834  -0.313  1.00  0.00           N  
HETATM   21  C16 UNL     1      -1.513   0.767  -1.710  1.00  0.00           C  
HETATM   22  C17 UNL     1      -2.754   1.338  -1.636  1.00  0.00           C  
HETATM   23  H1  UNL     1      -3.851   0.071   1.242  1.00  0.00           H  
HETATM   24  H2  UNL     1      -1.589  -0.997   1.148  1.00  0.00           H  
HETATM   25  H3  UNL     1       0.516  -0.782  -1.872  1.00  0.00           H  
HETATM   26  H4  UNL     1       1.079  -0.725   1.833  1.00  0.00           H  
HETATM   27  H5  UNL     1       2.759   0.693   2.883  1.00  0.00           H  
HETATM   28  H6  UNL     1       3.418   2.641  -0.886  1.00  0.00           H  
HETATM   29  H7  UNL     1       1.739   1.232  -1.955  1.00  0.00           H  
HETATM   30  H8  UNL     1       2.240  -2.367   0.521  1.00  0.00           H  
HETATM   31  H9  UNL     1      -1.195  -4.895   0.377  1.00  0.00           H  
HETATM   32  H10 UNL     1      -0.853   0.974  -2.560  1.00  0.00           H  
HETATM   33  H11 UNL     1      -3.064   2.009  -2.456  1.00  0.00           H  
CONECT    1    2    2    2
CONECT    2    3
CONECT    3    4    4   22
CONECT    4    5   23
CONECT    5    6    6   24
CONECT    6    7   21
CONECT    7    8   16   25
CONECT    8    9    9   15
CONECT    9   10   26
CONECT   10   11   11   27
CONECT   11   12   14
CONECT   12   13   13   13
CONECT   14   15   15   28
CONECT   15   29
CONECT   16   17   20
CONECT   17   18   18   30
CONECT   18   19
CONECT   19   20   20   31
CONECT   21   22   22   32
CONECT   22   33
END

HMDB0015141
     RDKit          3D
Letrozole
 33 35  0  0  0  0  0  0  0  0999 V2000
   -5.9417    2.2160   -0.4993 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8957    1.7084   -0.5304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5977    1.0913   -0.5771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1707    0.2392    0.4377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9176   -0.3306    0.3515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0843   -0.0769   -0.7101 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2694   -0.7042   -0.7845 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2808    0.1439   -0.1367 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5687    0.0017    1.1997 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5286    0.8014    1.8308 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1894    1.7570    1.0490 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1806    2.5792    1.7113 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9729    3.2317    2.2493 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9060    1.9049   -0.2902 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9418    1.0894   -0.8872 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2531   -2.0639   -0.2559 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2454   -2.7479    0.3411 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7271   -3.9454    0.6398 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5557   -4.0226    0.2456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8324   -2.8337   -0.3129 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5133    0.7669   -1.7102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7537    1.3382   -1.6363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8513    0.0714    1.2423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5885   -0.9966    1.1484 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5160   -0.7815   -1.8718 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0787   -0.7248    1.8330 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7589    0.6933    2.8827 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4175    2.6413   -0.8855 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7393    1.2320   -1.9549 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2404   -2.3671    0.5209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1950   -4.8952    0.3766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8532    0.9738   -2.5605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0639    2.0092   -2.4561 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  3  0
 11 14  1  0
 14 15  2  0
  7 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
  6 21  1  0
 21 22  2  0
 22  3  1  0
 15  8  1  0
 20 16  1  0
  4 23  1  0
  5 24  1  0
  7 25  1  0
  9 26  1  0
 10 27  1  0
 14 28  1  0
 15 29  1  0
 17 30  1  0
 19 31  1  0
 21 32  1  0
 22 33  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Femara	ChEBI
Letrozol	ChEBI
4,4'-(1H-1,2,4-Triazol-1-yl-methylene)-bis(benzonitrile)	HMDB
Fémara	HMDB
Novartis brand OF letrozole	HMDB

Chemical Formula

C₁₇H₁₁N₅

Average Molecular Weight

285.3027

Monoisotopic Molecular Weight

285.101445377

IUPAC Name

4-[(4-cyanophenyl)(1H-1,2,4-triazol-1-yl)methyl]benzonitrile

Traditional Name

letrozole

CAS Registry Number

112809-51-5

SMILES

N#CC1=CC=C(C=C1)C(N1C=NC=N1)C1=CC=C(C=C1)C#N

InChI Identifier

InChI=1S/C17H11N5/c18-9-13-1-5-15(6-2-13)17(22-12-20-11-21-22)16-7-3-14(10-19)4-8-16/h1-8,11-12,17H

InChI Key

HPJKCIUCZWXJDR-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Diphenylmethanes

Direct Parent

Diphenylmethanes

Alternative Parents

Substituents

Diphenylmethane
Benzonitrile
Heteroaromatic compound
1,2,4-triazole
Azole
Azacycle
Organoheterocyclic compound
Nitrile
Carbonitrile
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

nitrile (CHEBI:6413 )
triazoles (CHEBI:6413 )

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: HMDB0015141)

Source

Exogenous

Exogenous (HMDB: HMDB0015141)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	184 - 185 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.08 g/L	Not Available
LogP	2.5	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.08 g/L	ALOGPS
logP	1.86	ALOGPS
logP	2.94	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Basic)	2.17	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	78.29 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	94.47 m³·mol⁻¹	ChemAxon
Polarizability	29.59 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]+	164.88	31661259
DarkChem	[M-H]-	169.931	31661259
DeepCCS	[M+H]+	158.264	30932474
DeepCCS	[M-H]-	155.906	30932474
DeepCCS	[M-2H]-	189.17	30932474
DeepCCS	[M+Na]+	164.398	30932474
AllCCS	[M+H]+	167.6	32859911
AllCCS	[M+H-H2O]+	163.9	32859911
AllCCS	[M+NH4]+	171.0	32859911
AllCCS	[M+Na]+	172.0	32859911
AllCCS	[M-H]-	170.2	32859911
AllCCS	[M+Na-2H]-	169.5	32859911
AllCCS	[M+HCOO]-	168.8	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.	4.1 minutes	32390414
Predicted by Siyang on May 30, 2022	12.0876 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.68 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	28.5 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1672.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	325.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	157.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	203.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	145.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	453.7 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	564.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	97.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1018.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	432.5 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	1254.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	270.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	364.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	321.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	273.2 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	56.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Letrozole	N#CC1=CC=C(C=C1)C(N1C=NC=N1)C1=CC=C(C=C1)C#N	3840.9	Standard polar	33892256
Letrozole	N#CC1=CC=C(C=C1)C(N1C=NC=N1)C1=CC=C(C=C1)C#N	2846.9	Standard non polar	33892256
Letrozole	N#CC1=CC=C(C=C1)C(N1C=NC=N1)C1=CC=C(C=C1)C#N	2677.6	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 - Letrozole GC-MS (Non-derivatized) - 70eV, Positive	splash10-014i-5390000000-96e7cbf457562ce8f33a	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Letrozole GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Letrozole 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 - Letrozole LC-ESI-QFT , negative-QTOF	splash10-001i-0090000000-0fbd577a32ff572f7368	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Letrozole LC-ESI-QFT , negative-QTOF	splash10-001i-0190000000-dfcab9af789387521571	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Letrozole LC-ESI-QFT , negative-QTOF	splash10-0006-0390000000-dbc68fd6017abe6e8adc	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Letrozole LC-ESI-QFT , negative-QTOF	splash10-00kf-0490000000-c3fc389848a06a012234	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Letrozole LC-ESI-QFT , negative-QTOF	splash10-014l-0690000000-38ba597054b02b136ab6	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Letrozole LC-ESI-QFT , negative-QTOF	splash10-00kf-1980000000-13a8827cbc5c1b36a14f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Letrozole LC-ESI-QFT , negative-QTOF	splash10-00kf-3940000000-e01d63313ef1cfa7477a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Letrozole LC-ESI-QFT , negative-QTOF	splash10-014i-9410000000-83b93aed0756bd41adaf	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Letrozole LC-ESI-QFT , negative-QTOF	splash10-014i-9100000000-d1757f8c218d5dcc4809	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Letrozole LC-ESI-QFT , positive-QTOF	splash10-014i-0090000000-791121bd513899b7dfc0	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Letrozole LC-ESI-QFT , positive-QTOF	splash10-014i-0090000000-eb3996846ea4f036ccca	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Letrozole LC-ESI-QFT , positive-QTOF	splash10-014i-0390000000-a57ce4cfb24ba743c54b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Letrozole LC-ESI-QFT , positive-QTOF	splash10-0006-0950000000-303d99867511fe3a013b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Letrozole LC-ESI-QFT , positive-QTOF	splash10-0006-0930000000-77e720374927be5113ef	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Letrozole LC-ESI-QFT , positive-QTOF	splash10-0006-0920000000-4a93d8e76eb7d0d59481	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Letrozole LC-ESI-QFT , positive-QTOF	splash10-03du-0910000000-8ad9f37884e8686ef7ba	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Letrozole LC-ESI-QFT , positive-QTOF	splash10-03dr-2900000000-2274a3adb5e486f57001	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Letrozole LC-ESI-QFT , positive-QTOF	splash10-03dr-6900000000-74d56231c43250bc65ca	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Letrozole , positive-QTOF	splash10-014i-0490000000-7868daa9f0ec9ebda34a	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Letrozole 10V, Positive-QTOF	splash10-000i-0090000000-da3910c6e2a706e174c5	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Letrozole 20V, Positive-QTOF	splash10-001r-0090000000-f03b188334168da247e1	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Letrozole 40V, Positive-QTOF	splash10-003r-1970000000-d83cde690a839474f8d6	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Letrozole 10V, Negative-QTOF	splash10-001i-0090000000-f0fe35676feb362f0824	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Letrozole 20V, Negative-QTOF	splash10-001i-0090000000-b517dd9b4d5a4a7b26a2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Letrozole 40V, Negative-QTOF	splash10-053r-2290000000-f5f7a0dda898f84a52af	2016-08-03	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 DB01006	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01006	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

DB01006

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

3765

KEGG Compound ID

C08163

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Letrozole

METLIN ID

Not Available

PubChem Compound

3902

PDB ID

Not Available

ChEBI ID

6413

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

Tulandi T, Martin J, Al-Fadhli R, Kabli N, Forman R, Hitkari J, Librach C, Greenblatt E, Casper RF: Congenital malformations among 911 newborns conceived after infertility treatment with letrozole or clomiphene citrate. Fertil Steril. 2006 Jun;85(6):1761-5. Epub 2006 May 2. [PubMed:16650422 ]

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 19A1

General function:: Involved in monooxygenase activity
Specific function:: Catalyzes the formation of aromatic C18 estrogens from C19 androgens.
Gene Name:: CYP19A1
Uniprot ID:: P11511
Molecular weight:: 57882.48

References

Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Ebert AD, Bartley J, David M, Schweppe KW: [Aromatase inhibitors--theoretical concept and present experiences in the treatment of endometriosis]. Zentralbl Gynakol. 2003 Jul-Aug;125(7-8):247-51. [PubMed:14505258 ]
Long BJ, Jelovac D, Handratta V, Thiantanawat A, MacPherson N, Ragaz J, Goloubeva OG, Brodie AM: Therapeutic strategies using the aromatase inhibitor letrozole and tamoxifen in a breast cancer model. J Natl Cancer Inst. 2004 Mar 17;96(6):456-65. [PubMed:15026471 ]
Murphy MJ Jr: Molecular Action and Clinical Relevance of Aromatase Inhibitors. Oncologist. 1998;3(2):129-130. [PubMed:10388095 ]
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

3. Cytochrome P450 2A6

General function:: Involved in monooxygenase activity
Specific function:: Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. Constitutes the major nicotine C-oxidase. Acts as a 1,4-cineole 2-exo-monooxygenase. Possesses low phenacetin O-deethylation activity.
Gene Name:: CYP2A6
Uniprot ID:: P11509
Molecular weight:: 56517.005

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 Letrozole (HMDB0015141)

MOL for HMDB0015141 (Letrozole)

3D MOL for HMDB0015141 (Letrozole)

3D SDF for HMDB0015141 (Letrozole)

3D-SDF for HMDB0015141 (Letrozole)

PDB for HMDB0015141 (Letrozole)

3D PDB for HMDB0015141 (Letrozole)

SMILES for HMDB0015141 (Letrozole)

INCHI for HMDB0015141 (Letrozole)

Structure for HMDB0015141 (Letrozole)

3D Structure for HMDB0015141 (Letrozole)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References