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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-07-04 18:57:46 UTC

Update Date

2019-07-23 07:15:02 UTC

HMDB ID

HMDB0060759

Secondary Accession Numbers

HMDB60759

Metabolite Identification

Common Name

4-Carboxynevirapine

Description

4-Carboxynevirapine, also known as azt glucuronide or GAZT, 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. In humans, 4-carboxynevirapine is involved in the nevirapine metabolism pathway. 4-Carboxynevirapine is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a small amount of articles have been published on 4-Carboxynevirapine.

Structure

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

HMDB0060759
     RDKit          3D
4-Carboxynevirapine
 34 37  0  0  0  0  0  0  0  0999 V2000
    0.8510    3.4790    0.6982 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5633    2.3430    0.2865 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5980    1.4774   -0.1606 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6475    0.0575   -0.0801 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9466   -0.3625    0.0342 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0798    0.5050    0.2126 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0618    1.7515    0.3189 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3603   -0.1138    0.2737 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1645   -1.7376    0.0548 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0714   -2.5634   -0.0372 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8023   -2.1030   -0.1458 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5628   -0.7822   -0.1693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8156   -0.4825   -0.2675 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6769   -1.5094   -0.7380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8259   -2.8425   -0.1539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9173   -1.7830    0.0997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4406    0.7506    0.0541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7698    0.6637    0.1173 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5749    1.7067    0.4071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0220    2.9580    0.6596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6641    3.0843    0.6034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8741    2.0005    0.3052 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3994    1.9523   -0.6134 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7442   -0.3842   -0.6402 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1714   -2.1524    0.1412 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2738   -3.6465   -0.0185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9329   -1.4305   -1.8352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2521   -3.1800    0.7328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1065   -3.6898   -0.8154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8851   -1.9300   -0.3796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9762   -1.4407    1.1456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6567    1.6077    0.4521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7028    3.7704    0.8887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2047    4.0261    0.7908 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  5  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 13 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22  2  1  0
 12  4  1  0
 16 14  1  0
 22 17  1  0
  3 23  1  0
  8 24  1  0
  9 25  1  0
 10 26  1  0
 14 27  1  0
 15 28  1  0
 15 29  1  0
 16 30  1  0
 16 31  1  0
 19 32  1  0
 20 33  1  0
 21 34  1  0
M  END

  Mrv0541 07041311572D          

 22 25  0  0  0  0            999 V2000
    0.0506   -2.9710    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8390   -2.7278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4438   -3.2889    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0226   -1.9235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4178   -1.3623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6014   -0.5580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3897   -0.3148    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9945   -0.8760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7378   -0.5180    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7378    0.3070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3253    1.0215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1503    1.0215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4811   -0.8760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0859   -0.3148    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8742   -0.5580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0578   -1.3623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4530   -1.9235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6647   -1.6803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1503   -2.3253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5083   -3.0686    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3253   -2.3253    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8109   -1.6803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 10 12  1  0  0  0  0
  9 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 13 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
  4 22  1  0  0  0  0
  8 22  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060759

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(=O)C1=CC=NC2=C1NC(=O)C1=CC=CN=C1N2C1CC1

> <INCHI_IDENTIFIER>
InChI=1S/C15H12N4O3/c20-14-10-2-1-6-16-12(10)19(8-3-4-8)13-11(18-14)9(15(21)22)5-7-17-13/h1-2,5-8H,3-4H2,(H,18,20)(H,21,22)

> <INCHI_KEY>
WDXCMIDQWGYHIN-UHFFFAOYSA-N

> <FORMULA>
C15H12N4O3

> <MOLECULAR_WEIGHT>
296.2808

> <EXACT_MASS>
296.09094027

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
28.86462985550313

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-cyclopropyl-10-oxo-2,4,9,15-tetraazatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3(8),4,6,11,13-hexaene-7-carboxylic acid

> <ALOGPS_LOGP>
1.18

> <JCHEM_LOGP>
2.0770888304691373

> <ALOGPS_LOGS>
-2.76

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.925890080833463

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.5797721807342455

> <JCHEM_PKA_STRONGEST_BASIC>
3.374969584263452

> <JCHEM_POLAR_SURFACE_AREA>
95.41999999999999

> <JCHEM_REFRACTIVITY>
79.69699999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.18e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-cyclopropyl-10-oxo-2,4,9,15-tetraazatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3(8),4,6,11,13-hexaene-7-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060759
     RDKit          3D
4-Carboxynevirapine
 34 37  0  0  0  0  0  0  0  0999 V2000
    0.8510    3.4790    0.6982 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5633    2.3430    0.2865 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5980    1.4774   -0.1606 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6475    0.0575   -0.0801 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9466   -0.3625    0.0342 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0798    0.5050    0.2126 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0618    1.7515    0.3189 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3603   -0.1138    0.2737 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1645   -1.7376    0.0548 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0714   -2.5634   -0.0372 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8023   -2.1030   -0.1458 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5628   -0.7822   -0.1693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8156   -0.4825   -0.2675 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6769   -1.5094   -0.7380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8259   -2.8425   -0.1539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9173   -1.7830    0.0997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4406    0.7506    0.0541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7698    0.6637    0.1173 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5749    1.7067    0.4071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0220    2.9580    0.6596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6641    3.0843    0.6034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8741    2.0005    0.3052 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3994    1.9523   -0.6134 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7442   -0.3842   -0.6402 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1714   -2.1524    0.1412 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2738   -3.6465   -0.0185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9329   -1.4305   -1.8352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2521   -3.1800    0.7328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1065   -3.6898   -0.8154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8851   -1.9300   -0.3796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9762   -1.4407    1.1456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6567    1.6077    0.4521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7028    3.7704    0.8887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2047    4.0261    0.7908 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  5  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 13 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22  2  1  0
 12  4  1  0
 16 14  1  0
 22 17  1  0
  3 23  1  0
  8 24  1  0
  9 25  1  0
 10 26  1  0
 14 27  1  0
 15 28  1  0
 15 29  1  0
 16 30  1  0
 16 31  1  0
 19 32  1  0
 20 33  1  0
 21 34  1  0
M  END

HEADER    PROTEIN                                 04-JUL-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-JUL-13         0                                  
HETATM    1  O   UNK     0       0.094  -5.546   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.566  -5.092   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.695  -6.139   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.909  -3.591   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.780  -2.543   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.123  -1.042   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       2.594  -0.588   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       3.723  -1.635   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       5.111  -0.967   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       5.111   0.573   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.341   1.907   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.881   1.907   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.498  -1.635   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       7.627  -0.588   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       9.099  -1.042   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.441  -2.543   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.312  -3.591   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.841  -3.137   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.881  -4.341   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       6.549  -5.728   0.000  0.00  0.00           O+0
HETATM   21  N   UNK     0       4.341  -4.341   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0       3.380  -3.137   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   22                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   22                                                  
CONECT    9    8   10   13                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10   12                                                       
CONECT   12   11   10                                                       
CONECT   13    9   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   13   19                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21    4    8                                                  
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

COMPND    HMDB0060759
HETATM    1  O1  UNL     1       0.851   3.479   0.698  1.00  0.00           O  
HETATM    2  C1  UNL     1       0.563   2.343   0.287  1.00  0.00           C  
HETATM    3  N1  UNL     1       1.598   1.477  -0.161  1.00  0.00           N  
HETATM    4  C2  UNL     1       1.648   0.058  -0.080  1.00  0.00           C  
HETATM    5  C3  UNL     1       2.947  -0.362   0.034  1.00  0.00           C  
HETATM    6  C4  UNL     1       4.080   0.505   0.213  1.00  0.00           C  
HETATM    7  O2  UNL     1       4.062   1.752   0.319  1.00  0.00           O  
HETATM    8  O3  UNL     1       5.360  -0.114   0.274  1.00  0.00           O  
HETATM    9  C5  UNL     1       3.165  -1.738   0.055  1.00  0.00           C  
HETATM   10  C6  UNL     1       2.071  -2.563  -0.037  1.00  0.00           C  
HETATM   11  N2  UNL     1       0.802  -2.103  -0.146  1.00  0.00           N  
HETATM   12  C7  UNL     1       0.563  -0.782  -0.169  1.00  0.00           C  
HETATM   13  N3  UNL     1      -0.816  -0.483  -0.267  1.00  0.00           N  
HETATM   14  C8  UNL     1      -1.677  -1.509  -0.738  1.00  0.00           C  
HETATM   15  C9  UNL     1      -1.826  -2.843  -0.154  1.00  0.00           C  
HETATM   16  C10 UNL     1      -2.917  -1.783   0.100  1.00  0.00           C  
HETATM   17  C11 UNL     1      -1.441   0.751   0.054  1.00  0.00           C  
HETATM   18  N4  UNL     1      -2.770   0.664   0.117  1.00  0.00           N  
HETATM   19  C12 UNL     1      -3.575   1.707   0.407  1.00  0.00           C  
HETATM   20  C13 UNL     1      -3.022   2.958   0.660  1.00  0.00           C  
HETATM   21  C14 UNL     1      -1.664   3.084   0.603  1.00  0.00           C  
HETATM   22  C15 UNL     1      -0.874   2.001   0.305  1.00  0.00           C  
HETATM   23  H1  UNL     1       2.399   1.952  -0.613  1.00  0.00           H  
HETATM   24  H2  UNL     1       5.744  -0.384  -0.640  1.00  0.00           H  
HETATM   25  H3  UNL     1       4.171  -2.152   0.141  1.00  0.00           H  
HETATM   26  H4  UNL     1       2.274  -3.646  -0.019  1.00  0.00           H  
HETATM   27  H5  UNL     1      -1.933  -1.430  -1.835  1.00  0.00           H  
HETATM   28  H6  UNL     1      -1.252  -3.180   0.733  1.00  0.00           H  
HETATM   29  H7  UNL     1      -2.106  -3.690  -0.815  1.00  0.00           H  
HETATM   30  H8  UNL     1      -3.885  -1.930  -0.380  1.00  0.00           H  
HETATM   31  H9  UNL     1      -2.976  -1.441   1.146  1.00  0.00           H  
HETATM   32  H10 UNL     1      -4.657   1.608   0.452  1.00  0.00           H  
HETATM   33  H11 UNL     1      -3.703   3.770   0.889  1.00  0.00           H  
HETATM   34  H12 UNL     1      -1.205   4.026   0.791  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   22
CONECT    3    4   23
CONECT    4    5    5   12
CONECT    5    6    9
CONECT    6    7    7    8
CONECT    8   24
CONECT    9   10   10   25
CONECT   10   11   26
CONECT   11   12   12
CONECT   12   13
CONECT   13   14   17
CONECT   14   15   16   27
CONECT   15   16   28   29
CONECT   16   30   31
CONECT   17   18   18   22
CONECT   18   19
CONECT   19   20   20   32
CONECT   20   21   33
CONECT   21   22   22   34
END

HMDB0060759
     RDKit          3D
4-Carboxynevirapine
 34 37  0  0  0  0  0  0  0  0999 V2000
    0.8510    3.4790    0.6982 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5633    2.3430    0.2865 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5980    1.4774   -0.1606 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6475    0.0575   -0.0801 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9466   -0.3625    0.0342 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0798    0.5050    0.2126 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0618    1.7515    0.3189 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3603   -0.1138    0.2737 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1645   -1.7376    0.0548 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0714   -2.5634   -0.0372 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8023   -2.1030   -0.1458 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5628   -0.7822   -0.1693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8156   -0.4825   -0.2675 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6769   -1.5094   -0.7380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8259   -2.8425   -0.1539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9173   -1.7830    0.0997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4406    0.7506    0.0541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7698    0.6637    0.1173 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5749    1.7067    0.4071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0220    2.9580    0.6596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6641    3.0843    0.6034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8741    2.0005    0.3052 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3994    1.9523   -0.6134 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7442   -0.3842   -0.6402 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1714   -2.1524    0.1412 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2738   -3.6465   -0.0185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9329   -1.4305   -1.8352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2521   -3.1800    0.7328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1065   -3.6898   -0.8154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8851   -1.9300   -0.3796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9762   -1.4407    1.1456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6567    1.6077    0.4521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7028    3.7704    0.8887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2047    4.0261    0.7908 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  5  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 13 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22  2  1  0
 12  4  1  0
 16 14  1  0
 22 17  1  0
  3 23  1  0
  8 24  1  0
  9 25  1  0
 10 26  1  0
 14 27  1  0
 15 28  1  0
 15 29  1  0
 16 30  1  0
 16 31  1  0
 19 32  1  0
 20 33  1  0
 21 34  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3'-Azido-3'-deoxy-5'- O-b-D-glucopyranuronosylthymidine	HMDB
3'-Azido-3'-deoxy-5'- O-β-D-glucopyranuronosylthymidine	HMDB
AZT glucuronide	HMDB
3'-Azido-3'-deoxy-5'-O-beta-glucopyranuronosylthymidine	HMDB
GAZT	HMDB
AZT-5'-glucuronide	HMDB

Chemical Formula

C₁₅H₁₂N₄O₃

Average Molecular Weight

296.2808

Monoisotopic Molecular Weight

296.09094027

IUPAC Name

2-cyclopropyl-10-oxo-2,4,9,15-tetraazatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3(8),4,6,11,13-hexaene-7-carboxylic acid

Traditional Name

2-cyclopropyl-10-oxo-2,4,9,15-tetraazatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3(8),4,6,11,13-hexaene-7-carboxylic acid

CAS Registry Number

Not Available

SMILES

OC(=O)C1=CC=NC2=C1NC(=O)C1=CC=CN=C1N2C1CC1

InChI Identifier

InChI=1S/C15H12N4O3/c20-14-10-2-1-6-16-12(10)19(8-3-4-8)13-11(18-14)9(15(21)22)5-7-17-13/h1-2,5-8H,3-4H2,(H,18,20)(H,21,22)

InChI Key

WDXCMIDQWGYHIN-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
Pyridine carboxylic acid
Pyridine carboxylic acid or derivatives
Para-diazepine
Pyridine
Imidolactam
Heteroaromatic compound
Vinylogous amide
Carboxamide group
Lactam
Secondary carboxylic acid amide
Azacycle
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organic oxygen compound
Organopnictogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060759)

Organ

Kidney (HMDB: HMDB0060759)
Liver (HMDB: HMDB0060759)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060759)

Cellular substructure

Cytoplasm (HMDB: HMDB0060759)
Membrane (HMDB: HMDB0060759)

Source

Endogenous

Endogenous (HMDB: HMDB0060759)

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	0.52 g/L	ALOGPS
logP	1.18	ALOGPS
logP	2.08	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	4.58	ChemAxon
pKa (Strongest Basic)	3.37	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	95.42 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	79.7 m³·mol⁻¹	ChemAxon
Polarizability	28.86 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]+	165.067	31661259
DarkChem	[M-H]-	162.738	31661259
DeepCCS	[M+H]+	160.78	30932474
DeepCCS	[M-H]-	158.422	30932474
DeepCCS	[M-2H]-	192.113	30932474
DeepCCS	[M+Na]+	167.284	30932474
AllCCS	[M+H]+	167.3	32859911
AllCCS	[M+H-H2O]+	164.0	32859911
AllCCS	[M+NH4]+	170.5	32859911
AllCCS	[M+Na]+	171.4	32859911
AllCCS	[M-H]-	167.6	32859911
AllCCS	[M+Na-2H]-	166.8	32859911
AllCCS	[M+HCOO]-	166.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Carboxynevirapine	OC(=O)C1=CC=NC2=C1NC(=O)C1=CC=CN=C1N2C1CC1	3918.3	Standard polar	33892256
4-Carboxynevirapine	OC(=O)C1=CC=NC2=C1NC(=O)C1=CC=CN=C1N2C1CC1	2768.8	Standard non polar	33892256
4-Carboxynevirapine	OC(=O)C1=CC=NC2=C1NC(=O)C1=CC=CN=C1N2C1CC1	2651.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-Carboxynevirapine,1TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC=NC2=C1NC(=O)C1=CC=CN=C1N2C1CC1	2875.6	Semi standard non polar	33892256
4-Carboxynevirapine,1TMS,isomer #2	C[Si](C)(C)N1C(=O)C2=CC=CN=C2N(C2CC2)C2=NC=CC(C(=O)O)=C21	2679.8	Semi standard non polar	33892256
4-Carboxynevirapine,2TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC=NC2=C1N([Si](C)(C)C)C(=O)C1=CC=CN=C1N2C1CC1	2659.2	Semi standard non polar	33892256
4-Carboxynevirapine,2TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC=NC2=C1N([Si](C)(C)C)C(=O)C1=CC=CN=C1N2C1CC1	2720.7	Standard non polar	33892256
4-Carboxynevirapine,2TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC=NC2=C1N([Si](C)(C)C)C(=O)C1=CC=CN=C1N2C1CC1	3872.3	Standard polar	33892256
4-Carboxynevirapine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC=NC2=C1NC(=O)C1=CC=CN=C1N2C1CC1	3101.5	Semi standard non polar	33892256
4-Carboxynevirapine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C(=O)C2=CC=CN=C2N(C2CC2)C2=NC=CC(C(=O)O)=C21	2967.1	Semi standard non polar	33892256
4-Carboxynevirapine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC=NC2=C1N([Si](C)(C)C(C)(C)C)C(=O)C1=CC=CN=C1N2C1CC1	3057.5	Semi standard non polar	33892256
4-Carboxynevirapine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC=NC2=C1N([Si](C)(C)C(C)(C)C)C(=O)C1=CC=CN=C1N2C1CC1	3093.8	Standard non polar	33892256
4-Carboxynevirapine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC=NC2=C1N([Si](C)(C)C(C)(C)C)C(=O)C1=CC=CN=C1N2C1CC1	3919.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Carboxynevirapine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0kuu-0490000000-868c3fa487d18d561bcf	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Carboxynevirapine GC-MS (1 TMS) - 70eV, Positive	splash10-0fn9-8497000000-b1059cc66c8651a2f9f6	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Carboxynevirapine 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 - 4-Carboxynevirapine 10V, Positive-QTOF	splash10-0002-0090000000-03fc360d0dd52eeaf3eb	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Carboxynevirapine 20V, Positive-QTOF	splash10-0ufs-0090000000-b9d8e1529284c8d08e6a	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Carboxynevirapine 40V, Positive-QTOF	splash10-0gvx-8190000000-8eeb53c98632b1d30dad	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Carboxynevirapine 10V, Negative-QTOF	splash10-0udj-0090000000-3758c78030929ebc316c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Carboxynevirapine 20V, Negative-QTOF	splash10-0udi-0090000000-b0d5580a8d1a49c7fa29	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Carboxynevirapine 40V, Negative-QTOF	splash10-0bt9-0490000000-e08953300981317eca97	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Carboxynevirapine 10V, Positive-QTOF	splash10-002b-0090000000-ab5963bf94cd943f310b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Carboxynevirapine 20V, Positive-QTOF	splash10-0002-0090000000-e68a8916533f9476ac08	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Carboxynevirapine 40V, Positive-QTOF	splash10-03dr-0290000000-28294370a3a15f4e979c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Carboxynevirapine 10V, Negative-QTOF	splash10-0udi-0090000000-2d8d283e12d342c2f5a3	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Carboxynevirapine 20V, Negative-QTOF	splash10-0zfr-0090000000-ee1b50340d9632c80d4e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Carboxynevirapine 40V, Negative-QTOF	splash10-0bt9-0190000000-b405eca4e4edb6268eb9	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane (predicted from logP)

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	Normal	Not Available	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	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

8884376

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10709035

PDB ID

Not Available

ChEBI ID

169675

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 4-Carboxynevirapine (HMDB0060759)

MOL for HMDB0060759 (4-Carboxynevirapine)

3D MOL for HMDB0060759 (4-Carboxynevirapine)

3D SDF for HMDB0060759 (4-Carboxynevirapine)

3D-SDF for HMDB0060759 (4-Carboxynevirapine)

PDB for HMDB0060759 (4-Carboxynevirapine)

3D PDB for HMDB0060759 (4-Carboxynevirapine)

SMILES for HMDB0060759 (4-Carboxynevirapine)

INCHI for HMDB0060759 (4-Carboxynevirapine)

Structure for HMDB0060759 (4-Carboxynevirapine)

3D Structure for HMDB0060759 (4-Carboxynevirapine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra