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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:00:26 UTC

Update Date

2020-02-26 21:39:13 UTC

HMDB ID

HMDB0013912

Secondary Accession Numbers

HMDB13912

Metabolite Identification

Common Name

2-Hydroxynevirapine

Description

N-Desmethylcitalopram belongs to the class of organic compounds known as phenylbutylamines. Phenylbutylamines are compounds containing a phenylbutylamine moiety, which consists of a phenyl group substituted at the fourth carbon by an butan-1-amine. N-Desmethylcitalopram is a very strong basic compound (based on its pKa). N-Desmethylcitalopram exists in all living organisms, ranging from bacteria to humans. Within humans, N-desmethylcitalopram participates in a number of enzymatic reactions. In particular, N-desmethylcitalopram can be converted into citalopram aldehyde and methylammonium; which is catalyzed by the enzymes amine oxidase [flavin-containing] a and amine oxidase [flavin-containing] b. In addition, N-desmethylcitalopram and formaldehyde can be biosynthesized from citalopram; which is mediated by the enzymes cytochrome P450 2D6, cytochrome P450 3A7, and cytochrome P450 2C19. In humans, N-desmethylcitalopram is involved in citalopram metabolism pathway. N-Desmethylcitalopram is only found in individuals that have used or taken Citalopram.

Structure

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

HMDB0013912
     RDKit          3D
2-Hydroxynevirapine
 35 38  0  0  0  0  0  0  0  0999 V2000
    3.8503    0.8543    0.3579 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7935   -0.1411    0.1283 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0553   -1.4913   -0.1099 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9962   -2.3651   -0.3167 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3528   -3.7068   -0.5495 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7125   -1.9792   -0.3002 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4481   -0.6828   -0.0717 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4765    0.2451    0.1432 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3634    1.6377    0.3824 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2842    2.4722   -0.0573 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4819    3.6916   -0.0229 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0341    2.0579   -0.5462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7928    3.0936   -1.0380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0576    2.8135   -1.5228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5771    1.5324   -1.5272 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7803    0.5625   -1.0305 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5576    0.7817   -0.5532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9543   -0.4497   -0.0896 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8518   -1.4622    0.3403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3122   -2.6355    1.0840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3179   -1.6880    1.7033 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9392    1.1778    1.4031 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7460    1.7589   -0.2938 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8171    0.3847    0.0293 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0701   -1.8344   -0.1298 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2332   -4.4150    0.1681 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1366    2.0686    0.9216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3702    4.0777   -1.0247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6752    3.6184   -1.9167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5616    1.3454   -1.9097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6169   -1.7322   -0.4725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6619   -3.6584    0.8147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3273   -2.6613    1.5760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3339   -2.1421    1.8561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9741   -1.1291    2.5745 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  4  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
  8  2  1  0
 17 12  1  0
 21 19  1  0
 18  7  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  5 26  1  0
  9 27  1  0
 13 28  1  0
 14 29  1  0
 15 30  1  0
 19 31  1  0
 20 32  1  0
 20 33  1  0
 21 34  1  0
 21 35  1  0
M  END


  Mrv0541 06191310302D          

 21 24  0  0  0  0            999 V2000
    9.6933   -1.7777    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9231   -4.3279    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5106   -2.5208    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5590   -4.5641    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.2870   -4.5641    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.9231   -5.1529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5106   -5.8671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3355   -5.8671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1799   -3.9700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6662   -3.9700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9963   -3.1659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8498   -3.1659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1793   -2.8999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3355   -2.5208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6668   -2.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5449   -3.4794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7360   -4.3172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1100   -4.3172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0051   -2.0937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3013   -3.4794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1335   -4.8807    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1 14  2  0  0  0  0
  2  6  1  0  0  0  0
  2  9  1  0  0  0  0
  2 10  1  0  0  0  0
  3 11  1  0  0  0  0
  3 14  1  0  0  0  0
  4  9  2  0  0  0  0
  4 17  1  0  0  0  0
  5 10  1  0  0  0  0
  5 18  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  7  8  1  0  0  0  0
  9 11  1  0  0  0  0
 10 12  2  0  0  0  0
 11 13  2  0  0  0  0
 12 14  1  0  0  0  0
 12 15  1  0  0  0  0
 13 16  1  0  0  0  0
 13 19  1  0  0  0  0
 15 20  2  0  0  0  0
 16 17  2  0  0  0  0
 18 20  1  0  0  0  0
 17 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0013912

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=C2NC(=O)C3=C(N=CC=C3)N(C3CC3)C2=NC(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H14N4O2/c1-8-7-11(20)17-14-12(8)18-15(21)10-3-2-6-16-13(10)19(14)9-4-5-9/h2-3,6-7,9H,4-5H2,1H3,(H,17,20)(H,18,21)

> <INCHI_KEY>
LFZSOJABLBVGRJ-UHFFFAOYSA-N

> <FORMULA>
C15H14N4O2

> <MOLECULAR_WEIGHT>
282.2973

> <EXACT_MASS>
282.111675712

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
28.827336558411808

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-cyclopropyl-5-hydroxy-7-methyl-2,4,9,15-tetraazatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3,5,7,12,14-hexaen-10-one

> <ALOGPS_LOGP>
1.68

> <JCHEM_LOGP>
2.778934987

> <ALOGPS_LOGS>
-2.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.146859485728053

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.27472347862628

> <JCHEM_PKA_STRONGEST_BASIC>
3.4357909283949564

> <JCHEM_POLAR_SURFACE_AREA>
78.35000000000001

> <JCHEM_REFRACTIVITY>
79.77640000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.50e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-cyclopropyl-5-hydroxy-7-methyl-2,4,9,15-tetraazatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3,5,7,12,14-hexaen-10-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0013912
     RDKit          3D
2-Hydroxynevirapine
 35 38  0  0  0  0  0  0  0  0999 V2000
    3.8503    0.8543    0.3579 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7935   -0.1411    0.1283 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0553   -1.4913   -0.1099 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9962   -2.3651   -0.3167 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3528   -3.7068   -0.5495 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7125   -1.9792   -0.3002 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4481   -0.6828   -0.0717 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4765    0.2451    0.1432 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3634    1.6377    0.3824 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2842    2.4722   -0.0573 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4819    3.6916   -0.0229 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0341    2.0579   -0.5462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7928    3.0936   -1.0380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0576    2.8135   -1.5228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5771    1.5324   -1.5272 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7803    0.5625   -1.0305 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5576    0.7817   -0.5532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9543   -0.4497   -0.0896 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8518   -1.4622    0.3403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3122   -2.6355    1.0840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3179   -1.6880    1.7033 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9392    1.1778    1.4031 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7460    1.7589   -0.2938 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8171    0.3847    0.0293 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0701   -1.8344   -0.1298 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2332   -4.4150    0.1681 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1366    2.0686    0.9216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3702    4.0777   -1.0247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6752    3.6184   -1.9167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5616    1.3454   -1.9097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6169   -1.7322   -0.4725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6619   -3.6584    0.8147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3273   -2.6613    1.5760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3339   -2.1421    1.8561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9741   -1.1291    2.5745 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  4  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
  8  2  1  0
 17 12  1  0
 21 19  1  0
 18  7  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  5 26  1  0
  9 27  1  0
 13 28  1  0
 14 29  1  0
 15 30  1  0
 19 31  1  0
 20 32  1  0
 20 33  1  0
 21 34  1  0
 21 35  1  0
M  END

HEADER    PROTEIN                                 19-JUN-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-13         0                                  
HETATM    1  O   UNK     0      18.094  -3.318   0.000  0.00  0.00           O+0
HETATM    2  N   UNK     0      16.656  -8.079   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0      15.886  -4.706   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0      14.110  -8.520   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0      19.202  -8.520   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      16.656  -9.619   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      15.886 -10.952   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      17.426 -10.952   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      15.269  -7.411   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      18.044  -7.411   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      14.926  -5.910   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      18.386  -5.910   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.401  -5.413   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      17.426  -4.706   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      19.911  -5.413   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.217  -6.495   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.574  -8.059   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      20.739  -8.059   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      13.076  -3.908   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      21.096  -6.495   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      11.449  -9.111   0.000  0.00  0.00           O+0
CONECT    1   14                                                            
CONECT    2    6    9   10                                                  
CONECT    3   11   14                                                       
CONECT    4    9   17                                                       
CONECT    5   10   18                                                       
CONECT    6    2    7    8                                                  
CONECT    7    6    8                                                       
CONECT    8    6    7                                                       
CONECT    9    2    4   11                                                  
CONECT   10    2    5   12                                                  
CONECT   11    3    9   13                                                  
CONECT   12   10   14   15                                                  
CONECT   13   11   16   19                                                  
CONECT   14    1    3   12                                                  
CONECT   15   12   20                                                       
CONECT   16   13   17                                                       
CONECT   17    4   16   21                                                  
CONECT   18    5   20                                                       
CONECT   19   13                                                            
CONECT   20   15   18                                                       
CONECT   21   17                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   48    0
END

COMPND    HMDB0013912
HETATM    1  C1  UNL     1       3.850   0.854   0.358  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.794  -0.141   0.128  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.055  -1.491  -0.110  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.996  -2.365  -0.317  1.00  0.00           C  
HETATM    5  O1  UNL     1       2.353  -3.707  -0.549  1.00  0.00           O  
HETATM    6  N1  UNL     1       0.712  -1.979  -0.300  1.00  0.00           N  
HETATM    7  C5  UNL     1       0.448  -0.683  -0.072  1.00  0.00           C  
HETATM    8  C6  UNL     1       1.476   0.245   0.143  1.00  0.00           C  
HETATM    9  N2  UNL     1       1.363   1.638   0.382  1.00  0.00           N  
HETATM   10  C7  UNL     1       0.284   2.472  -0.057  1.00  0.00           C  
HETATM   11  O2  UNL     1       0.482   3.692  -0.023  1.00  0.00           O  
HETATM   12  C8  UNL     1      -1.034   2.058  -0.546  1.00  0.00           C  
HETATM   13  C9  UNL     1      -1.793   3.094  -1.038  1.00  0.00           C  
HETATM   14  C10 UNL     1      -3.058   2.814  -1.523  1.00  0.00           C  
HETATM   15  C11 UNL     1      -3.577   1.532  -1.527  1.00  0.00           C  
HETATM   16  N3  UNL     1      -2.780   0.563  -1.030  1.00  0.00           N  
HETATM   17  C12 UNL     1      -1.558   0.782  -0.553  1.00  0.00           C  
HETATM   18  N4  UNL     1      -0.954  -0.450  -0.090  1.00  0.00           N  
HETATM   19  C13 UNL     1      -1.852  -1.462   0.340  1.00  0.00           C  
HETATM   20  C14 UNL     1      -1.312  -2.636   1.084  1.00  0.00           C  
HETATM   21  C15 UNL     1      -2.318  -1.688   1.703  1.00  0.00           C  
HETATM   22  H1  UNL     1       3.939   1.178   1.403  1.00  0.00           H  
HETATM   23  H2  UNL     1       3.746   1.759  -0.294  1.00  0.00           H  
HETATM   24  H3  UNL     1       4.817   0.385   0.029  1.00  0.00           H  
HETATM   25  H4  UNL     1       4.070  -1.834  -0.130  1.00  0.00           H  
HETATM   26  H5  UNL     1       2.233  -4.415   0.168  1.00  0.00           H  
HETATM   27  H6  UNL     1       2.137   2.069   0.922  1.00  0.00           H  
HETATM   28  H7  UNL     1      -1.370   4.078  -1.025  1.00  0.00           H  
HETATM   29  H8  UNL     1      -3.675   3.618  -1.917  1.00  0.00           H  
HETATM   30  H9  UNL     1      -4.562   1.345  -1.910  1.00  0.00           H  
HETATM   31  H10 UNL     1      -2.617  -1.732  -0.472  1.00  0.00           H  
HETATM   32  H11 UNL     1      -1.662  -3.658   0.815  1.00  0.00           H  
HETATM   33  H12 UNL     1      -0.327  -2.661   1.576  1.00  0.00           H  
HETATM   34  H13 UNL     1      -3.334  -2.142   1.856  1.00  0.00           H  
HETATM   35  H14 UNL     1      -1.974  -1.129   2.575  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3    3    8
CONECT    3    4   25
CONECT    4    5    6    6
CONECT    5   26
CONECT    6    7
CONECT    7    8    8   18
CONECT    8    9
CONECT    9   10   27
CONECT   10   11   11   12
CONECT   12   13   13   17
CONECT   13   14   28
CONECT   14   15   15   29
CONECT   15   16   30
CONECT   16   17   17
CONECT   17   18
CONECT   18   19
CONECT   19   20   21   31
CONECT   20   21   32   33
CONECT   21   34   35
END

HMDB0013912
     RDKit          3D
2-Hydroxynevirapine
 35 38  0  0  0  0  0  0  0  0999 V2000
    3.8503    0.8543    0.3579 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7935   -0.1411    0.1283 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0553   -1.4913   -0.1099 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9962   -2.3651   -0.3167 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3528   -3.7068   -0.5495 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7125   -1.9792   -0.3002 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4481   -0.6828   -0.0717 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4765    0.2451    0.1432 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3634    1.6377    0.3824 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2842    2.4722   -0.0573 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4819    3.6916   -0.0229 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0341    2.0579   -0.5462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7928    3.0936   -1.0380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0576    2.8135   -1.5228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5771    1.5324   -1.5272 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7803    0.5625   -1.0305 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5576    0.7817   -0.5532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9543   -0.4497   -0.0896 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8518   -1.4622    0.3403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3122   -2.6355    1.0840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3179   -1.6880    1.7033 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9392    1.1778    1.4031 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7460    1.7589   -0.2938 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8171    0.3847    0.0293 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0701   -1.8344   -0.1298 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2332   -4.4150    0.1681 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1366    2.0686    0.9216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3702    4.0777   -1.0247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6752    3.6184   -1.9167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5616    1.3454   -1.9097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6169   -1.7322   -0.4725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6619   -3.6584    0.8147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3273   -2.6613    1.5760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3339   -2.1421    1.8561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9741   -1.1291    2.5745 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  4  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
  8  2  1  0
 17 12  1  0
 21 19  1  0
 18  7  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  5 26  1  0
  9 27  1  0
 13 28  1  0
 14 29  1  0
 15 30  1  0
 19 31  1  0
 20 32  1  0
 20 33  1  0
 21 34  1  0
 21 35  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Monodesmethylcitalopram monohydrochloride	HMDB
Monodesmethylcitalopram	HMDB
Monodesmethylcitalopram oxalate	HMDB

Chemical Formula

C₁₅H₁₄N₄O₂

Average Molecular Weight

282.2973

Monoisotopic Molecular Weight

282.111675712

IUPAC Name

2-cyclopropyl-5-hydroxy-7-methyl-2,4,9,15-tetraazatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3,5,7,12,14-hexaen-10-one

Traditional Name

2-cyclopropyl-5-hydroxy-7-methyl-2,4,9,15-tetraazatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3,5,7,12,14-hexaen-10-one

CAS Registry Number

Not Available

SMILES

CC1=C2NC(=O)C3=C(N=CC=C3)N(C3CC3)C2=NC(O)=C1

InChI Identifier

InChI=1S/C15H14N4O2/c1-8-7-11(20)17-14-12(8)18-15(21)10-3-2-6-16-13(10)19(14)9-4-5-9/h2-3,6-7,9H,4-5H2,1H3,(H,17,20)(H,18,21)

InChI Key

LFZSOJABLBVGRJ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylbutylamines. Phenylbutylamines are compounds containing a phenylbutylamine moiety, which consists of a phenyl group substituted at the fourth carbon by an butan-1-amine.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenylbutylamines

Direct Parent

Phenylbutylamines

Alternative Parents

Substituents

Phenylbutylamine
Isocoumaran
Fluorobenzene
Halobenzene
Aralkylamine
Aryl fluoride
Aryl halide
Dialkyl ether
Secondary aliphatic amine
Ether
Carbonitrile
Nitrile
Oxacycle
Secondary amine
Organoheterocyclic compound
Organic oxygen compound
Hydrocarbon derivative
Amine
Organohalogen compound
Organofluoride
Organonitrogen compound
Organooxygen compound
Organic nitrogen compound
Organopnictogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organic amino compound (CHEBI:80603 )
benzenes (CHEBI:80603 )

Ontology

Not Available

Liver (HMDB: HMDB0013912)
Kidney (HMDB: HMDB0013912)

Biofluid or Excreta

Excreta

Urine (PMID: 21059682)

Non-excretory biofluid

Blood (PMID: 21059682)

Cellular substructure

Extracellular (HMDB: HMDB0013912)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Nevirapine Metabolism Pathway (PathBank: SMP0000642)

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.45 g/L	ALOGPS
logP	1.68	ALOGPS
logP	2.78	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	10.27	ChemAxon
pKa (Strongest Basic)	3.44	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	78.35 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	79.78 m³·mol⁻¹	ChemAxon
Polarizability	28.83 Å³	ChemAxon
Number of Rings	4	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]+	163.145	31661259
DarkChem	[M-H]-	160.555	31661259
DeepCCS	[M+H]+	176.511	30932474
DeepCCS	[M-H]-	174.153	30932474
DeepCCS	[M-2H]-	207.404	30932474
DeepCCS	[M+Na]+	182.63	30932474
AllCCS	[M+H]+	165.6	32859911
AllCCS	[M+H-H2O]+	162.1	32859911
AllCCS	[M+NH4]+	168.9	32859911
AllCCS	[M+Na]+	169.8	32859911
AllCCS	[M-H]-	167.4	32859911
AllCCS	[M+Na-2H]-	166.7	32859911
AllCCS	[M+HCOO]-	166.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Hydroxynevirapine	CC1=C2NC(=O)C3=C(N=CC=C3)N(C3CC3)C2=NC(O)=C1	3794.4	Standard polar	33892256
2-Hydroxynevirapine	CC1=C2NC(=O)C3=C(N=CC=C3)N(C3CC3)C2=NC(O)=C1	2727.7	Standard non polar	33892256
2-Hydroxynevirapine	CC1=C2NC(=O)C3=C(N=CC=C3)N(C3CC3)C2=NC(O)=C1	2511.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-Hydroxynevirapine,1TMS,isomer #1	CC1=CC(O[Si](C)(C)C)=NC2=C1NC(=O)C1=CC=CN=C1N2C1CC1	2791.1	Semi standard non polar	33892256
2-Hydroxynevirapine,1TMS,isomer #2	CC1=CC(O)=NC2=C1N([Si](C)(C)C)C(=O)C1=CC=CN=C1N2C1CC1	2554.3	Semi standard non polar	33892256
2-Hydroxynevirapine,2TMS,isomer #1	CC1=CC(O[Si](C)(C)C)=NC2=C1N([Si](C)(C)C)C(=O)C1=CC=CN=C1N2C1CC1	2576.1	Semi standard non polar	33892256
2-Hydroxynevirapine,2TMS,isomer #1	CC1=CC(O[Si](C)(C)C)=NC2=C1N([Si](C)(C)C)C(=O)C1=CC=CN=C1N2C1CC1	2646.0	Standard non polar	33892256
2-Hydroxynevirapine,2TMS,isomer #1	CC1=CC(O[Si](C)(C)C)=NC2=C1N([Si](C)(C)C)C(=O)C1=CC=CN=C1N2C1CC1	3544.6	Standard polar	33892256
2-Hydroxynevirapine,1TBDMS,isomer #1	CC1=CC(O[Si](C)(C)C(C)(C)C)=NC2=C1NC(=O)C1=CC=CN=C1N2C1CC1	2976.8	Semi standard non polar	33892256
2-Hydroxynevirapine,1TBDMS,isomer #2	CC1=CC(O)=NC2=C1N([Si](C)(C)C(C)(C)C)C(=O)C1=CC=CN=C1N2C1CC1	2812.7	Semi standard non polar	33892256
2-Hydroxynevirapine,2TBDMS,isomer #1	CC1=CC(O[Si](C)(C)C(C)(C)C)=NC2=C1N([Si](C)(C)C(C)(C)C)C(=O)C1=CC=CN=C1N2C1CC1	2945.0	Semi standard non polar	33892256
2-Hydroxynevirapine,2TBDMS,isomer #1	CC1=CC(O[Si](C)(C)C(C)(C)C)=NC2=C1N([Si](C)(C)C(C)(C)C)C(=O)C1=CC=CN=C1N2C1CC1	3046.6	Standard non polar	33892256
2-Hydroxynevirapine,2TBDMS,isomer #1	CC1=CC(O[Si](C)(C)C(C)(C)C)=NC2=C1N([Si](C)(C)C(C)(C)C)C(=O)C1=CC=CN=C1N2C1CC1	3628.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hydroxynevirapine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0gyx-1890000000-d6054af1eebe72c5c4b6	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hydroxynevirapine GC-MS (1 TMS) - 70eV, Positive	splash10-001i-4798000000-b8c5512169e5a41410d8	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hydroxynevirapine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hydroxynevirapine 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 - 2-Hydroxynevirapine 10V, Positive-QTOF	splash10-001i-0090000000-ce583e2d4d570a450bca	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxynevirapine 20V, Positive-QTOF	splash10-00lr-1090000000-e083894c3878d5c74216	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxynevirapine 40V, Positive-QTOF	splash10-0udl-9060000000-54c0ec5ecb9c00e9cbd7	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxynevirapine 10V, Negative-QTOF	splash10-001i-0090000000-d505115f37815beecdcc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxynevirapine 20V, Negative-QTOF	splash10-001l-0090000000-a4df3e2565cf4bfd0f37	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxynevirapine 40V, Negative-QTOF	splash10-0fkd-1390000000-75ca606ca619a020a8d5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxynevirapine 10V, Negative-QTOF	splash10-001i-0090000000-d72761c0346bc09759b0	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxynevirapine 20V, Negative-QTOF	splash10-001i-0090000000-adc3593c967ca7859292	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxynevirapine 40V, Negative-QTOF	splash10-03ml-1690000000-9ef93e955157aa2c14c7	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxynevirapine 10V, Positive-QTOF	splash10-001i-0090000000-7c900f9f8b3f17914393	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxynevirapine 20V, Positive-QTOF	splash10-001l-0090000000-c910612007c88e00763a	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxynevirapine 40V, Positive-QTOF	splash10-004l-0390000000-09499c647b8bf959668a	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Name	SMPDB/PathBank	KEGG
Nevirapine Metabolism Pathway		Not Available

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

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

142424

KEGG Compound ID

C16608

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Desmethylcitalopram

METLIN ID

Not Available

PubChem Compound

162180

PDB ID

Not Available

ChEBI ID

586865

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

Not Available

Showing metabocard for 2-Hydroxynevirapine (HMDB0013912)

MOL for HMDB0013912 (2-Hydroxynevirapine)

3D MOL for HMDB0013912 (2-Hydroxynevirapine)

3D SDF for HMDB0013912 (2-Hydroxynevirapine)

3D-SDF for HMDB0013912 (2-Hydroxynevirapine)

PDB for HMDB0013912 (2-Hydroxynevirapine)

3D PDB for HMDB0013912 (2-Hydroxynevirapine)

SMILES for HMDB0013912 (2-Hydroxynevirapine)

INCHI for HMDB0013912 (2-Hydroxynevirapine)

Structure for HMDB0013912 (2-Hydroxynevirapine)

3D Structure for HMDB0013912 (2-Hydroxynevirapine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra