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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2022-03-07 02:51:36 UTC

HMDB ID

HMDB0014383

Secondary Accession Numbers

HMDB14383

Metabolite Identification

Common Name

Nevirapine

Description

Nevirapine is only found in individuals that have used or taken this drug. It is a potent, non-nucleoside reverse transcriptase inhibitor used in combination with nucleoside analogues for treatment of HIV infection and AIDS. [PubChem]Nevirapine binds directly to reverse transcriptase (RT) and blocks the RNA-dependent and DNA-dependent DNA polymerase activities by causing a disruption of the enzyme's catalytic site. The activity of nevirapine does not compete with template or nucleoside triphosphates.

Structure

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

HMDB0014383
     RDKit          3D
Nevirapine
 34 37  0  0  0  0  0  0  0  0999 V2000
    3.9541    0.4216   -0.2790 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8120   -0.4642    0.0755 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0150   -1.7463    0.5378 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9360   -2.5437    0.8579 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7052   -2.0337    0.7049 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4842   -0.8019    0.2613 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5408    0.0190   -0.0665 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5269    1.3606   -0.5498 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4870    2.3023   -0.3769 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7204    3.4930   -0.6387 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8824    2.0346    0.0906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6230    3.1770    0.2917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9276    3.1132    0.7288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4745    1.8729    0.9605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7424    0.7370    0.7620 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4727    0.7975    0.3367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8967   -0.5167    0.1956 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8215   -1.5644   -0.0166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5719   -2.9609   -0.2851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9521   -2.0334   -1.4690 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8941   -0.0814    0.0573 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0029    0.5005   -1.3635 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8913    1.3859    0.2550 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0480   -2.1093    0.6424 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1570   -3.5394    1.2153 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3542    1.6668   -1.0724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1966    4.1473    0.1109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4820    4.0307    0.8768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4921    1.7681    1.3036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8377   -1.3349    0.4323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3953   -3.6940   -0.0177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6401   -3.4792   -0.4806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9548   -2.1717   -1.9011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1657   -1.7528   -2.1801 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  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  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  1  0
 18 19  1  0
 19 20  1  0
  7  2  1  0
 16 11  1  0
 20 18  1  0
 17  6  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  4 25  1  0
  8 26  1  0
 12 27  1  0
 13 28  1  0
 14 29  1  0
 18 30  1  0
 19 31  1  0
 19 32  1  0
 20 33  1  0
 20 34  1  0
M  END

238
  Mrv0541 02231214322D          

 20 23  0  0  0  0            999 V2000
    4.7984    2.0448    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0281   -0.5055    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6156    1.3017    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6640   -0.7417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3921   -0.7417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0281   -1.3305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6156   -2.0448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4406   -2.0448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2849   -0.1476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7713   -0.1476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1013    0.6566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9549    0.6566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2842    0.9226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4406    1.3017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7719    0.9225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6498    0.3430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8410   -0.4948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2151   -0.4948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1100    1.7288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4064    0.3430    0.0000 C   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
M  END
> <DATABASE_ID>
HMDB0014383

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C15H14N4O/c1-9-6-8-17-14-12(9)18-15(20)11-3-2-7-16-13(11)19(14)10-4-5-10/h2-3,6-8,10H,4-5H2,1H3,(H,18,20)

> <INCHI_KEY>
NQDJXKOVJZTUJA-UHFFFAOYSA-N

> <FORMULA>
C15H14N4O

> <MOLECULAR_WEIGHT>
266.2979

> <EXACT_MASS>
266.11676109

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
27.79965668476118

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-cyclopropyl-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>
1.75

> <JCHEM_LOGP>
2.488042778666667

> <ALOGPS_LOGS>
-3.41

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.371185534086782

> <JCHEM_PKA_STRONGEST_BASIC>
5.05792102225345

> <JCHEM_POLAR_SURFACE_AREA>
58.120000000000005

> <JCHEM_REFRACTIVITY>
77.482

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.05e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
nevirapine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014383
     RDKit          3D
Nevirapine
 34 37  0  0  0  0  0  0  0  0999 V2000
    3.9541    0.4216   -0.2790 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8120   -0.4642    0.0755 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0150   -1.7463    0.5378 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9360   -2.5437    0.8579 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7052   -2.0337    0.7049 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4842   -0.8019    0.2613 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5408    0.0190   -0.0665 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5269    1.3606   -0.5498 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4870    2.3023   -0.3769 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7204    3.4930   -0.6387 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8824    2.0346    0.0906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6230    3.1770    0.2917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9276    3.1132    0.7288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4745    1.8729    0.9605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7424    0.7370    0.7620 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4727    0.7975    0.3367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8967   -0.5167    0.1956 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8215   -1.5644   -0.0166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5719   -2.9609   -0.2851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9521   -2.0334   -1.4690 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8941   -0.0814    0.0573 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0029    0.5005   -1.3635 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8913    1.3859    0.2550 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0480   -2.1093    0.6424 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1570   -3.5394    1.2153 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3542    1.6668   -1.0724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1966    4.1473    0.1109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4820    4.0307    0.8768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4921    1.7681    1.3036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8377   -1.3349    0.4323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3953   -3.6940   -0.0177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6401   -3.4792   -0.4806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9548   -2.1717   -1.9011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1657   -1.7528   -2.1801 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  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  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  1  0
 18 19  1  0
 19 20  1  0
  7  2  1  0
 16 11  1  0
 20 18  1  0
 17  6  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  4 25  1  0
  8 26  1  0
 12 27  1  0
 13 28  1  0
 14 29  1  0
 18 30  1  0
 19 31  1  0
 19 32  1  0
 20 33  1  0
 20 34  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 238                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       8.957   3.817   0.000  0.00  0.00           O+0
HETATM    2  N   UNK     0       7.519  -0.944   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0       6.749   2.430   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0       4.973  -1.385   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0      10.065  -1.385   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       7.519  -2.484   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.749  -3.817   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.289  -3.817   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.132  -0.276   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.906  -0.276   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.789   1.226   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.249   1.226   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.264   1.722   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.289   2.430   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.774   1.722   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.080   0.640   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.437  -0.924   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.602  -0.924   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.939   3.227   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.959   0.640   0.000  0.00  0.00           C+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                                                       
CONECT   18    5   20                                                       
CONECT   19   13                                                            
CONECT   20   15   18                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   46    0
END

COMPND    HMDB0014383
HETATM    1  C1  UNL     1       3.954   0.422  -0.279  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.812  -0.464   0.075  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.015  -1.746   0.538  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.936  -2.544   0.858  1.00  0.00           C  
HETATM    5  N1  UNL     1       0.705  -2.034   0.705  1.00  0.00           N  
HETATM    6  C5  UNL     1       0.484  -0.802   0.261  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.541   0.019  -0.067  1.00  0.00           C  
HETATM    8  N2  UNL     1       1.527   1.361  -0.550  1.00  0.00           N  
HETATM    9  C7  UNL     1       0.487   2.302  -0.377  1.00  0.00           C  
HETATM   10  O1  UNL     1       0.720   3.493  -0.639  1.00  0.00           O  
HETATM   11  C8  UNL     1      -0.882   2.035   0.091  1.00  0.00           C  
HETATM   12  C9  UNL     1      -1.623   3.177   0.292  1.00  0.00           C  
HETATM   13  C10 UNL     1      -2.928   3.113   0.729  1.00  0.00           C  
HETATM   14  C11 UNL     1      -3.474   1.873   0.960  1.00  0.00           C  
HETATM   15  N3  UNL     1      -2.742   0.737   0.762  1.00  0.00           N  
HETATM   16  C12 UNL     1      -1.473   0.797   0.337  1.00  0.00           C  
HETATM   17  N4  UNL     1      -0.897  -0.517   0.196  1.00  0.00           N  
HETATM   18  C13 UNL     1      -1.821  -1.564  -0.017  1.00  0.00           C  
HETATM   19  C14 UNL     1      -1.572  -2.961  -0.285  1.00  0.00           C  
HETATM   20  C15 UNL     1      -1.952  -2.033  -1.469  1.00  0.00           C  
HETATM   21  H1  UNL     1       4.894  -0.081   0.057  1.00  0.00           H  
HETATM   22  H2  UNL     1       4.003   0.500  -1.363  1.00  0.00           H  
HETATM   23  H3  UNL     1       3.891   1.386   0.255  1.00  0.00           H  
HETATM   24  H4  UNL     1       4.048  -2.109   0.642  1.00  0.00           H  
HETATM   25  H5  UNL     1       2.157  -3.539   1.215  1.00  0.00           H  
HETATM   26  H6  UNL     1       2.354   1.667  -1.072  1.00  0.00           H  
HETATM   27  H7  UNL     1      -1.197   4.147   0.111  1.00  0.00           H  
HETATM   28  H8  UNL     1      -3.482   4.031   0.877  1.00  0.00           H  
HETATM   29  H9  UNL     1      -4.492   1.768   1.304  1.00  0.00           H  
HETATM   30  H10 UNL     1      -2.838  -1.335   0.432  1.00  0.00           H  
HETATM   31  H11 UNL     1      -2.395  -3.694  -0.018  1.00  0.00           H  
HETATM   32  H12 UNL     1      -0.640  -3.479  -0.481  1.00  0.00           H  
HETATM   33  H13 UNL     1      -2.955  -2.172  -1.901  1.00  0.00           H  
HETATM   34  H14 UNL     1      -1.166  -1.753  -2.180  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3    3    7
CONECT    3    4   24
CONECT    4    5    5   25
CONECT    5    6
CONECT    6    7    7   17
CONECT    7    8
CONECT    8    9   26
CONECT    9   10   10   11
CONECT   11   12   12   16
CONECT   12   13   27
CONECT   13   14   14   28
CONECT   14   15   29
CONECT   15   16   16
CONECT   16   17
CONECT   17   18
CONECT   18   19   20   30
CONECT   19   20   31   32
CONECT   20   33   34
END

HMDB0014383
     RDKit          3D
Nevirapine
 34 37  0  0  0  0  0  0  0  0999 V2000
    3.9541    0.4216   -0.2790 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8120   -0.4642    0.0755 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0150   -1.7463    0.5378 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9360   -2.5437    0.8579 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7052   -2.0337    0.7049 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4842   -0.8019    0.2613 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5408    0.0190   -0.0665 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5269    1.3606   -0.5498 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4870    2.3023   -0.3769 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7204    3.4930   -0.6387 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8824    2.0346    0.0906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6230    3.1770    0.2917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9276    3.1132    0.7288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4745    1.8729    0.9605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7424    0.7370    0.7620 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4727    0.7975    0.3367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8967   -0.5167    0.1956 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8215   -1.5644   -0.0166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5719   -2.9609   -0.2851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9521   -2.0334   -1.4690 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8941   -0.0814    0.0573 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0029    0.5005   -1.3635 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8913    1.3859    0.2550 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0480   -2.1093    0.6424 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1570   -3.5394    1.2153 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3542    1.6668   -1.0724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1966    4.1473    0.1109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4820    4.0307    0.8768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4921    1.7681    1.3036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8377   -1.3349    0.4323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3953   -3.6940   -0.0177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6401   -3.4792   -0.4806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9548   -2.1717   -1.9011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1657   -1.7528   -2.1801 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  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  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  1  0
 18 19  1  0
 19 20  1  0
  7  2  1  0
 16 11  1  0
 20 18  1  0
 17  6  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  4 25  1  0
  8 26  1  0
 12 27  1  0
 13 28  1  0
 14 29  1  0
 18 30  1  0
 19 31  1  0
 19 32  1  0
 20 33  1  0
 20 34  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
11-Cyclopropyl-5,11-dihydro-4-methyl-6H-dipyrido(3,2-b:2',3'-e)(1,4)diazepin-6-one	ChEBI
NEV	ChEBI
NVP	ChEBI
Viramune	ChEBI
ABBR NVP	Kegg
Nevirapine hemihydrate	HMDB
BI RG 587	HMDB
BIRG587	HMDB
Hemihydrate, nevirapine	HMDB
BI-RG-587	HMDB

Chemical Formula

C₁₅H₁₄N₄O

Average Molecular Weight

266.2979

Monoisotopic Molecular Weight

266.11676109

IUPAC Name

2-cyclopropyl-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

nevirapine

CAS Registry Number

129618-40-2

SMILES

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

InChI Identifier

InChI=1S/C15H14N4O/c1-9-6-8-17-14-12(9)18-15(20)11-3-2-7-16-13(11)19(14)10-4-5-10/h2-3,6-8,10H,4-5H2,1H3,(H,18,20)

InChI Key

NQDJXKOVJZTUJA-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alkyldiarylamines. These are tertiary alkylarylamines having two aryl and one alkyl groups attached to the amino group.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Amines

Direct Parent

Alkyldiarylamines

Alternative Parents

Substituents

Alkyldiarylamine
Pyrido-para-diazepine
Para-diazepine
Methylpyridine
Imidolactam
Pyridine
Heteroaromatic compound
Vinylogous amide
Carboxamide group
Lactam
Secondary carboxylic acid amide
Carboxylic acid derivative
Azacycle
Organoheterocyclic compound
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

dipyridodiazepine (CHEBI:63613 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	196.06 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.1 g/L	Not Available
LogP	2.5	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.1 g/L	ALOGPS
logP	1.75	ALOGPS
logP	2.49	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	10.37	ChemAxon
pKa (Strongest Basic)	5.06	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	58.12 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	77.48 m³·mol⁻¹	ChemAxon
Polarizability	27.8 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]+	161.832	31661259
DarkChem	[M-H]-	161.708	31661259
DeepCCS	[M+H]+	170.637	30932474
DeepCCS	[M-H]-	168.279	30932474
DeepCCS	[M-2H]-	201.47	30932474
DeepCCS	[M+Na]+	176.731	30932474
AllCCS	[M+H]+	162.1	32859911
AllCCS	[M+H-H2O]+	158.4	32859911
AllCCS	[M+NH4]+	165.5	32859911
AllCCS	[M+Na]+	166.5	32859911
AllCCS	[M-H]-	164.6	32859911
AllCCS	[M+Na-2H]-	163.9	32859911
AllCCS	[M+HCOO]-	163.3	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.	3.25 minutes	32390414
Predicted by Siyang on May 30, 2022	9.9963 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.71 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	29.5 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	881.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	203.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	111.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	143.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	50.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	299.0 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	429.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	112.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	680.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	61.1 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	1129.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	183.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	261.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	377.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	161.3 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	138.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Nevirapine	CC1=C2NC(=O)C3=C(N=CC=C3)N(C3CC3)C2=NC=C1	3510.5	Standard polar	33892256
Nevirapine	CC1=C2NC(=O)C3=C(N=CC=C3)N(C3CC3)C2=NC=C1	2403.5	Standard non polar	33892256
Nevirapine	CC1=C2NC(=O)C3=C(N=CC=C3)N(C3CC3)C2=NC=C1	2298.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Nevirapine,1TMS,isomer #1	CC1=CC=NC2=C1N([Si](C)(C)C)C(=O)C1=CC=CN=C1N2C1CC1	2390.5	Semi standard non polar	33892256
Nevirapine,1TMS,isomer #1	CC1=CC=NC2=C1N([Si](C)(C)C)C(=O)C1=CC=CN=C1N2C1CC1	2391.7	Standard non polar	33892256
Nevirapine,1TMS,isomer #1	CC1=CC=NC2=C1N([Si](C)(C)C)C(=O)C1=CC=CN=C1N2C1CC1	3572.1	Standard polar	33892256
Nevirapine,1TBDMS,isomer #1	CC1=CC=NC2=C1N([Si](C)(C)C(C)(C)C)C(=O)C1=CC=CN=C1N2C1CC1	2630.9	Semi standard non polar	33892256
Nevirapine,1TBDMS,isomer #1	CC1=CC=NC2=C1N([Si](C)(C)C(C)(C)C)C(=O)C1=CC=CN=C1N2C1CC1	2594.6	Standard non polar	33892256
Nevirapine,1TBDMS,isomer #1	CC1=CC=NC2=C1N([Si](C)(C)C(C)(C)C)C(=O)C1=CC=CN=C1N2C1CC1	3625.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Nevirapine GC-MS (Non-derivatized) - 70eV, Positive	splash10-01s9-0890000000-c2ef64541073a1c774c3	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nevirapine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nevirapine 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 - Nevirapine , positive-QTOF	splash10-016r-1390000000-cbb2d729a2b310bf5dd0	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nevirapine , positive-QTOF	splash10-016r-0290000000-64af72aec31bfd168e68	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nevirapine , positive-QTOF	splash10-004i-3980000000-98e328d2867c43716973	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nevirapine 35V, Positive-QTOF	splash10-00or-0390000000-8627dbd7619ad6589566	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nevirapine 10V, Positive-QTOF	splash10-014i-0090000000-e341212035575baee47c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nevirapine 20V, Positive-QTOF	splash10-014i-1090000000-aa8be82ca660a3a1654d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nevirapine 40V, Positive-QTOF	splash10-0k96-9240000000-96f26abab0ca2960a8d9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nevirapine 10V, Negative-QTOF	splash10-014i-0090000000-5ff2e0be399277e2d1e4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nevirapine 20V, Negative-QTOF	splash10-016r-0090000000-e6562b6940dd28d0a37b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nevirapine 40V, Negative-QTOF	splash10-0a6r-1890000000-d60a9db4a4fef99e1ca5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nevirapine 10V, Positive-QTOF	splash10-014i-0090000000-d1a08ff6bcda467abc31	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nevirapine 20V, Positive-QTOF	splash10-016r-0090000000-ab3762b78a7dc338267f	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nevirapine 40V, Positive-QTOF	splash10-004i-0390000000-40b55ad31c970d6bd2e3	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nevirapine 10V, Negative-QTOF	splash10-014i-0090000000-b7ee7f3fd2558633e840	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nevirapine 20V, Negative-QTOF	splash10-014i-0090000000-b8840f336feb8c33bccc	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nevirapine 40V, Negative-QTOF	splash10-0092-2950000000-37fa8e70d7fa15c73439	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Nevirapine Metabolism Pathway		Not Available
Nevirapine Action 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 DB00238	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00238	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00238

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4308

KEGG Compound ID

C07263

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Nevirapine

METLIN ID

Not Available

PubChem Compound

4463

PDB ID

NVP

ChEBI ID

63613

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

(). FDA label . .

Showing metabocard for Nevirapine (HMDB0014383)

MOL for HMDB0014383 (Nevirapine)

3D MOL for HMDB0014383 (Nevirapine)

3D SDF for HMDB0014383 (Nevirapine)

3D-SDF for HMDB0014383 (Nevirapine)

PDB for HMDB0014383 (Nevirapine)

3D PDB for HMDB0014383 (Nevirapine)

SMILES for HMDB0014383 (Nevirapine)

INCHI for HMDB0014383 (Nevirapine)

Structure for HMDB0014383 (Nevirapine)

3D Structure for HMDB0014383 (Nevirapine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra