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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 02:51:41 UTC

HMDB ID

HMDB0014638

Secondary Accession Numbers

HMDB14638

Metabolite Identification

Common Name

Zidovudine

Description

A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by an azido group. This modification prevents the formation of phosphodiester linkages which are needed for the completion of nucleic acid chains. The compound is a potent inhibitor of HIV replication, acting as a chain-terminator of viral DNA during reverse transcription. It improves immunologic function, partially reverses the HIV-induced neurological dysfunction, and improves certain other clinical abnormalities associated with AIDS. Its principal toxic effect is dose-dependent suppression of bone marrow, resulting in anemia and leukopenia. [PubChem]

Structure

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

HMDB0014638
     RDKit          3D
Zidovudine
 32 33  0  0  0  0  0  0  0  0999 V2000
    4.5104    0.7879    1.0924 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3518    0.3824    0.2580 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0856    0.3991    0.8119 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0305    0.0239    0.0333 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2919    0.0232    0.5537 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2062    1.0243   -0.0881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5629    0.4947    0.3216 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9825    1.2032    1.5245 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6897    2.1894    1.4243 N   0  0  0  0  0  4  0  0  0  0  0  0
   -4.7021    2.9116    1.4954 N   0  0  0  0  0  2  0  0  0  0  0  0
   -2.2949   -0.9533    0.5712 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0545   -1.7595   -0.4638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7475   -3.0975   -0.2520 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9545   -1.1858    0.3981 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2525   -0.3477   -1.2390 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2691   -0.6885   -1.9365 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4908   -0.3674   -1.7914 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5595   -0.0022   -1.0499 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7299    0.0076   -1.4814 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2749    1.2953    0.4999 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2058    1.3374    1.9977 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9820   -0.1734    1.4483 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8952    0.6971    1.8370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2932    0.2412    1.6518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1719    1.0106   -1.1861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0144    2.0429    0.3143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3133    0.6488   -0.4875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6632   -1.2346    1.5829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7125   -1.4315   -1.4535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1478   -1.5692   -0.3488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4634   -3.2483    0.7044 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6281   -0.6614   -2.7829 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
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  2  0
  7 11  1  0
 11 12  1  0
 12 13  1  0
 11 14  1  0
  4 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  2  0
 18  2  1  0
 14  5  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  5 24  1  1
  6 25  1  0
  6 26  1  0
  7 27  1  6
 11 28  1  1
 12 29  1  0
 12 30  1  0
 13 31  1  0
 17 32  1  0
M  CHG  2   9   1  10  -1
M  END

495
  Mrv1652305271900332D          

 19 20  0  0  1  0            999 V2000
    4.8558   -1.0026    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9063   -2.3685    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7595    0.3073    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1884    2.7823    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1884    0.3073    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2909   -2.4547    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4739    1.5448    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4705   -2.3685    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    1.6500   -2.2822    0.0000 N   0  5  0  0  0  0  0  0  0  0  0  0
    3.7759   -1.7873    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1884   -0.5177    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5210   -1.0026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6009   -1.7873    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0858   -2.4547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9029    0.7198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4739    0.7198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9029    1.5448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1884    1.9573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6174    1.9573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 11  1  0  0  0  0
  1 13  1  0  0  0  0
  2 14  1  0  0  0  0
  3 16  2  0  0  0  0
  4 18  2  0  0  0  0
 11  5  1  6  0  0  0
  5 15  1  0  0  0  0
  5 16  1  0  0  0  0
  6  8  2  0  0  0  0
 10  6  1  1  0  0  0
  7 16  1  0  0  0  0
  7 18  1  0  0  0  0
  8  9  2  0  0  0  0
 10 12  1  0  0  0  0
 10 13  1  0  0  0  0
 11 12  1  0  0  0  0
 13 14  1  6  0  0  0
 15 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
M  CHG  2   8   1   9  -1
M  END
> <DATABASE_ID>
HMDB0014638

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=CN([C@H]2C[C@H](N=[N+]=[N-])[C@@H](CO)O2)C(=O)NC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H13N5O4/c1-5-3-15(10(18)12-9(5)17)8-2-6(13-14-11)7(4-16)19-8/h3,6-8,16H,2,4H2,1H3,(H,12,17,18)/t6-,7+,8+/m0/s1

> <INCHI_KEY>
HBOMLICNUCNMMY-XLPZGREQSA-N

> <FORMULA>
C10H13N5O4

> <MOLECULAR_WEIGHT>
267.2413

> <EXACT_MASS>
267.096753929

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
24.76559408073848

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-[(2R,4S,5S)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione

> <ALOGPS_LOGP>
-0.10

> <JCHEM_LOGP>
-0.2987091583333329

> <ALOGPS_LOGS>
-1.21

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.62843573768546

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.96041555648723

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9769294063535847

> <JCHEM_POLAR_SURFACE_AREA>
108.30000000000001

> <JCHEM_REFRACTIVITY>
61.70450000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.63e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
zidovudine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014638
     RDKit          3D
Zidovudine
 32 33  0  0  0  0  0  0  0  0999 V2000
    4.5104    0.7879    1.0924 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3518    0.3824    0.2580 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0856    0.3991    0.8119 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0305    0.0239    0.0333 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2919    0.0232    0.5537 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2062    1.0243   -0.0881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5629    0.4947    0.3216 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9825    1.2032    1.5245 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6897    2.1894    1.4243 N   0  0  0  0  0  4  0  0  0  0  0  0
   -4.7021    2.9116    1.4954 N   0  0  0  0  0  2  0  0  0  0  0  0
   -2.2949   -0.9533    0.5712 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0545   -1.7595   -0.4638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7475   -3.0975   -0.2520 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9545   -1.1858    0.3981 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2525   -0.3477   -1.2390 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2691   -0.6885   -1.9365 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4908   -0.3674   -1.7914 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5595   -0.0022   -1.0499 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7299    0.0076   -1.4814 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2749    1.2953    0.4999 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2058    1.3374    1.9977 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9820   -0.1734    1.4483 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8952    0.6971    1.8370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2932    0.2412    1.6518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1719    1.0106   -1.1861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0144    2.0429    0.3143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3133    0.6488   -0.4875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6632   -1.2346    1.5829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7125   -1.4315   -1.4535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1478   -1.5692   -0.3488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4634   -3.2483    0.7044 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6281   -0.6614   -2.7829 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
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  2  0
  7 11  1  0
 11 12  1  0
 12 13  1  0
 11 14  1  0
  4 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  2  0
 18  2  1  0
 14  5  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  5 24  1  1
  6 25  1  0
  6 26  1  0
  7 27  1  6
 11 28  1  1
 12 29  1  0
 12 30  1  0
 13 31  1  0
 17 32  1  0
M  CHG  2   9   1  10  -1
M  END

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 495                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  O   UNK     0       9.064  -1.872   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      11.025  -4.421   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       5.151   0.574   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       7.818   5.194   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0       7.818   0.574   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0       6.143  -4.582   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0       6.485   2.884   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0       4.612  -4.421   0.000  0.00  0.00           N+1
HETATM    9  N   UNK     0       3.080  -4.260   0.000  0.00  0.00           N-1
HETATM   10  C   UNK     0       7.048  -3.336   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.818  -0.966   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.573  -1.872   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.588  -3.336   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.493  -4.582   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.152   1.344   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.485   1.344   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.152   2.884   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.818   3.654   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.486   3.654   0.000  0.00  0.00           C+0
CONECT    1   11   13                                                       
CONECT    2   14                                                            
CONECT    3   16                                                            
CONECT    4   18                                                            
CONECT    5   11   15   16                                                  
CONECT    6    8   10                                                       
CONECT    7   16   18                                                       
CONECT    8    6    9                                                       
CONECT    9    8                                                            
CONECT   10    6   12   13                                                  
CONECT   11    1    5   12                                                  
CONECT   12   10   11                                                       
CONECT   13    1   10   14                                                  
CONECT   14    2   13                                                       
CONECT   15    5   17                                                       
CONECT   16    3    5    7                                                  
CONECT   17   15   18   19                                                  
CONECT   18    4    7   17                                                  
CONECT   19   17                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

COMPND    HMDB0014638
HETATM    1  C1  UNL     1       4.510   0.788   1.092  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.352   0.382   0.258  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.086   0.399   0.812  1.00  0.00           C  
HETATM    4  N1  UNL     1       1.031   0.024   0.033  1.00  0.00           N  
HETATM    5  C4  UNL     1      -0.292   0.023   0.554  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.206   1.024  -0.088  1.00  0.00           C  
HETATM    7  C6  UNL     1      -2.563   0.495   0.322  1.00  0.00           C  
HETATM    8  N2  UNL     1      -2.983   1.203   1.525  1.00  0.00           N  
HETATM    9  N3  UNL     1      -3.690   2.189   1.424  1.00  0.00           N1+
HETATM   10  N4  UNL     1      -4.702   2.912   1.495  1.00  0.00           N1-
HETATM   11  C7  UNL     1      -2.295  -0.953   0.571  1.00  0.00           C  
HETATM   12  C8  UNL     1      -3.054  -1.760  -0.464  1.00  0.00           C  
HETATM   13  O1  UNL     1      -2.748  -3.097  -0.252  1.00  0.00           O  
HETATM   14  O2  UNL     1      -0.955  -1.186   0.398  1.00  0.00           O  
HETATM   15  C9  UNL     1       1.252  -0.348  -1.239  1.00  0.00           C  
HETATM   16  O3  UNL     1       0.269  -0.689  -1.937  1.00  0.00           O  
HETATM   17  N5  UNL     1       2.491  -0.367  -1.791  1.00  0.00           N  
HETATM   18  C10 UNL     1       3.560  -0.002  -1.050  1.00  0.00           C  
HETATM   19  O4  UNL     1       4.730   0.008  -1.481  1.00  0.00           O  
HETATM   20  H1  UNL     1       5.275   1.295   0.500  1.00  0.00           H  
HETATM   21  H2  UNL     1       4.206   1.337   1.998  1.00  0.00           H  
HETATM   22  H3  UNL     1       4.982  -0.173   1.448  1.00  0.00           H  
HETATM   23  H4  UNL     1       1.895   0.697   1.837  1.00  0.00           H  
HETATM   24  H5  UNL     1      -0.293   0.241   1.652  1.00  0.00           H  
HETATM   25  H6  UNL     1      -1.172   1.011  -1.186  1.00  0.00           H  
HETATM   26  H7  UNL     1      -1.014   2.043   0.314  1.00  0.00           H  
HETATM   27  H8  UNL     1      -3.313   0.649  -0.487  1.00  0.00           H  
HETATM   28  H9  UNL     1      -2.663  -1.235   1.583  1.00  0.00           H  
HETATM   29  H10 UNL     1      -2.712  -1.431  -1.453  1.00  0.00           H  
HETATM   30  H11 UNL     1      -4.148  -1.569  -0.349  1.00  0.00           H  
HETATM   31  H12 UNL     1      -2.463  -3.248   0.704  1.00  0.00           H  
HETATM   32  H13 UNL     1       2.628  -0.661  -2.783  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3    3   18
CONECT    3    4   23
CONECT    4    5   15
CONECT    5    6   14   24
CONECT    6    7   25   26
CONECT    7    8   11   27
CONECT    8    9    9
CONECT    9   10   10
CONECT   11   12   14   28
CONECT   12   13   29   30
CONECT   13   31
CONECT   15   16   16   17
CONECT   17   18   32
CONECT   18   19   19
END

HMDB0014638
     RDKit          3D
Zidovudine
 32 33  0  0  0  0  0  0  0  0999 V2000
    4.5104    0.7879    1.0924 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3518    0.3824    0.2580 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0856    0.3991    0.8119 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0305    0.0239    0.0333 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2919    0.0232    0.5537 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2062    1.0243   -0.0881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5629    0.4947    0.3216 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9825    1.2032    1.5245 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6897    2.1894    1.4243 N   0  0  0  0  0  4  0  0  0  0  0  0
   -4.7021    2.9116    1.4954 N   0  0  0  0  0  2  0  0  0  0  0  0
   -2.2949   -0.9533    0.5712 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0545   -1.7595   -0.4638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7475   -3.0975   -0.2520 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9545   -1.1858    0.3981 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2525   -0.3477   -1.2390 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2691   -0.6885   -1.9365 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4908   -0.3674   -1.7914 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5595   -0.0022   -1.0499 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7299    0.0076   -1.4814 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2749    1.2953    0.4999 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2058    1.3374    1.9977 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9820   -0.1734    1.4483 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8952    0.6971    1.8370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2932    0.2412    1.6518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1719    1.0106   -1.1861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0144    2.0429    0.3143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3133    0.6488   -0.4875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6632   -1.2346    1.5829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7125   -1.4315   -1.4535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1478   -1.5692   -0.3488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4634   -3.2483    0.7044 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6281   -0.6614   -2.7829 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
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  2  0
  7 11  1  0
 11 12  1  0
 12 13  1  0
 11 14  1  0
  4 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  2  0
 18  2  1  0
 14  5  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  5 24  1  1
  6 25  1  0
  6 26  1  0
  7 27  1  6
 11 28  1  1
 12 29  1  0
 12 30  1  0
 13 31  1  0
 17 32  1  0
M  CHG  2   9   1  10  -1
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Azidothymidine	ChEBI
AZT	ChEBI
Retrovir	ChEBI
Zidovudin	ChEBI
Zidovudinum	ChEBI
3'-Azido-3'-deoxythymidine	Kegg
3'-Azido-2',3'-dideoxythymidine	HMDB
AZT antiviral	HMDB
BWA 509u	HMDB
AZT (antiviral)	HMDB
3' Azido 3' deoxythymidine	HMDB
Antiviral azt	HMDB
BW a509U	HMDB
3' Azido 2',3' dideoxythymidine	HMDB
AZT, antiviral	HMDB
BWA-509u	HMDB
BWA509u	HMDB

Chemical Formula

C₁₀H₁₃N₅O₄

Average Molecular Weight

267.2413

Monoisotopic Molecular Weight

267.096753929

IUPAC Name

1-[(2R,4S,5S)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione

Traditional Name

zidovudine

CAS Registry Number

30516-87-1

SMILES

CC1=CN([C@H]2C[C@H](N=[N+]=[N-])[C@@H](CO)O2)C(=O)NC1=O

InChI Identifier

InChI=1S/C10H13N5O4/c1-5-3-15(10(18)12-9(5)17)8-2-6(13-14-11)7(4-16)19-8/h3,6-8,16H,2,4H2,1H3,(H,12,17,18)/t6-,7+,8+/m0/s1

InChI Key

HBOMLICNUCNMMY-XLPZGREQSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrimidine 2',3'-dideoxyribonucleosides. Pyrimidine 2',3'-dideoxyribonucleosides are compounds consisting of a pyrimidine linked to a ribose which lacks a hydroxyl group at positions 2 and 3.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Pyrimidine nucleosides

Sub Class

Pyrimidine 2',3'-dideoxyribonucleosides

Direct Parent

Pyrimidine 2',3'-dideoxyribonucleosides

Alternative Parents

Substituents

Pyrimidine 2',3'-dideoxyribonucleoside
Pyrimidone
Hydroxypyrimidine
Hydropyrimidine
Pyrimidine
Tetrahydrofuran
Heteroaromatic compound
Azo imide
Azo compound
Oxacycle
Azacycle
Organoheterocyclic compound
Organic zwitterion
Alcohol
Organic oxide
Organopnictogen compound
Organic oxygen compound
Primary alcohol
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Hydrocarbon derivative
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

azide (CHEBI:10110 )
pyrimidine 2',3'-dideoxyribonucleoside (CHEBI:10110 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Source

Exogenous

Exogenous (HMDB: HMDB0014638)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Zidovudine Action Pathway (PathBank: SMP0000747)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	106 - 112 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	16.3 g/L	Not Available
LogP	0.05	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	16.3 g/L	ALOGPS
logP	-0.1	ALOGPS
logP	-0.3	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	9.96	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	108.3 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	61.7 m³·mol⁻¹	ChemAxon
Polarizability	24.77 Å³	ChemAxon
Number of Rings	2	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]+	160.308	31661259
DarkChem	[M-H]-	155.371	31661259
DeepCCS	[M+H]+	161.999	30932474
DeepCCS	[M-H]-	159.641	30932474
DeepCCS	[M-2H]-	193.594	30932474
DeepCCS	[M+Na]+	168.762	30932474
AllCCS	[M+H]+	158.1	32859911
AllCCS	[M+H-H2O]+	154.5	32859911
AllCCS	[M+NH4]+	161.4	32859911
AllCCS	[M+Na]+	162.4	32859911
AllCCS	[M-H]-	159.5	32859911
AllCCS	[M+Na-2H]-	159.2	32859911
AllCCS	[M+HCOO]-	159.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Zidovudine	CC1=CN([C@H]2C[C@H](N=[N+]=[N-])[C@@H](CO)O2)C(=O)NC1=O	3594.0	Standard polar	33892256
Zidovudine	CC1=CN([C@H]2C[C@H](N=[N+]=[N-])[C@@H](CO)O2)C(=O)NC1=O	2143.5	Standard non polar	33892256
Zidovudine	CC1=CN([C@H]2C[C@H](N=[N+]=[N-])[C@@H](CO)O2)C(=O)NC1=O	2448.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Zidovudine,1TMS,isomer #1	CC1=CN([C@H]2C[C@H](N=[N+]=[N-])[C@@H](CO[Si](C)(C)C)O2)C(=O)[NH]C1=O	2410.0	Semi standard non polar	33892256
Zidovudine,1TMS,isomer #2	CC1=CN([C@H]2C[C@H](N=[N+]=[N-])[C@@H](CO)O2)C(=O)N([Si](C)(C)C)C1=O	2478.0	Semi standard non polar	33892256
Zidovudine,2TMS,isomer #1	CC1=CN([C@H]2C[C@H](N=[N+]=[N-])[C@@H](CO[Si](C)(C)C)O2)C(=O)N([Si](C)(C)C)C1=O	2469.3	Semi standard non polar	33892256
Zidovudine,2TMS,isomer #1	CC1=CN([C@H]2C[C@H](N=[N+]=[N-])[C@@H](CO[Si](C)(C)C)O2)C(=O)N([Si](C)(C)C)C1=O	2578.6	Standard non polar	33892256
Zidovudine,2TMS,isomer #1	CC1=CN([C@H]2C[C@H](N=[N+]=[N-])[C@@H](CO[Si](C)(C)C)O2)C(=O)N([Si](C)(C)C)C1=O	3831.4	Standard polar	33892256
Zidovudine,1TBDMS,isomer #1	CC1=CN([C@H]2C[C@H](N=[N+]=[N-])[C@@H](CO[Si](C)(C)C(C)(C)C)O2)C(=O)[NH]C1=O	2656.2	Semi standard non polar	33892256
Zidovudine,1TBDMS,isomer #2	CC1=CN([C@H]2C[C@H](N=[N+]=[N-])[C@@H](CO)O2)C(=O)N([Si](C)(C)C(C)(C)C)C1=O	2707.6	Semi standard non polar	33892256
Zidovudine,2TBDMS,isomer #1	CC1=CN([C@H]2C[C@H](N=[N+]=[N-])[C@@H](CO[Si](C)(C)C(C)(C)C)O2)C(=O)N([Si](C)(C)C(C)(C)C)C1=O	2927.9	Semi standard non polar	33892256
Zidovudine,2TBDMS,isomer #1	CC1=CN([C@H]2C[C@H](N=[N+]=[N-])[C@@H](CO[Si](C)(C)C(C)(C)C)O2)C(=O)N([Si](C)(C)C(C)(C)C)C1=O	3016.9	Standard non polar	33892256
Zidovudine,2TBDMS,isomer #1	CC1=CN([C@H]2C[C@H](N=[N+]=[N-])[C@@H](CO[Si](C)(C)C(C)(C)C)O2)C(=O)N([Si](C)(C)C(C)(C)C)C1=O	3832.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Zidovudine GC-MS (Non-derivatized) - 70eV, Positive	splash10-014i-9220000000-d55aacb79cb345dd1f0a	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Zidovudine GC-MS (1 TMS) - 70eV, Positive	splash10-0100-9631000000-1d566216a7cf9f0cc760	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Zidovudine 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 - Zidovudine LC-ESI-QFT , negative-QTOF	splash10-00di-0190000000-46ee7eb3034a9b20706d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Zidovudine LC-ESI-QFT , negative-QTOF	splash10-00di-0790000000-19916045eff2f2277d60	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Zidovudine LC-ESI-QFT , negative-QTOF	splash10-0fk9-0900000000-836aff54cb90ce573db4	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Zidovudine LC-ESI-QFT , negative-QTOF	splash10-00di-0900000000-cb1ef888d872056bce56	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Zidovudine LC-ESI-QFT , negative-QTOF	splash10-00di-0900000000-97660ea43493fa2fa991	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Zidovudine LC-ESI-QFT , negative-QTOF	splash10-05fr-0900000000-407e81a32dbf5eb07134	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Zidovudine LC-ESI-QFT , positive-QTOF	splash10-004i-0900000000-743290b40f399a527da5	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Zidovudine LC-ESI-QFT , positive-QTOF	splash10-004i-0900000000-667b9ae1f4c499b8cef6	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Zidovudine LC-ESI-QFT , positive-QTOF	splash10-004i-0900000000-c6bf89700e58ad9aff83	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Zidovudine LC-ESI-QFT , positive-QTOF	splash10-004i-1900000000-b644d0eec4449bae7675	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Zidovudine LC-ESI-QFT , positive-QTOF	splash10-01t9-2900000000-d794028d708aa5c5d04f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Zidovudine LC-ESI-QFT , positive-QTOF	splash10-03gi-5900000000-b2b0a6ddec7e2e91e8c4	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Zidovudine 15V, Negative-QTOF	splash10-00di-0190000000-7866a2ae697bd4bdd557	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Zidovudine 30V, Negative-QTOF	splash10-00di-0790000000-7a80e5d85a6e3caa70dc	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Zidovudine 90V, Positive-QTOF	splash10-03gi-4900000000-f20d571f80dacd82de5d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Zidovudine 75V, Positive-QTOF	splash10-01t9-2900000000-8d394bc55d4ea0b1cb90	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Zidovudine 15V, Positive-QTOF	splash10-004i-0900000000-bd6dbcfb91438fe39bc1	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Zidovudine 30V, Positive-QTOF	splash10-004i-0900000000-661e1e92b9a14d53eda3	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Zidovudine 60V, Positive-QTOF	splash10-004i-0900000000-c1e03c652eda06f4c392	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zidovudine 10V, Positive-QTOF	splash10-014i-0090000000-65bdc875b481997f35b0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zidovudine 20V, Positive-QTOF	splash10-03di-0090000000-cbe4e5e680eed587e220	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zidovudine 40V, Positive-QTOF	splash10-007c-9200000000-9732b6de02e7378e613c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zidovudine 10V, Negative-QTOF	splash10-014i-2090000000-d30081dd79d918431d63	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zidovudine 20V, Negative-QTOF	splash10-014i-4290000000-42d4b65040e25cf691f5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zidovudine 40V, Negative-QTOF	splash10-0006-9500000000-50cff13af2772ff9bd1e	2016-08-03	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Zidovudine 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 DB00495	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00495	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00495

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

32555

KEGG Compound ID

C07210

BioCyc ID

CPD-15110

BiGG ID

Not Available

Wikipedia Link

Zidovudine

METLIN ID

Not Available

PubChem Compound

35370

PDB ID

Not Available

ChEBI ID

10110

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

Mitsuya H, Yarchoan R, Broder S: Molecular targets for AIDS therapy. Science. 1990 Sep 28;249(4976):1533-44. [PubMed:1699273 ]
Mitsuya H, Weinhold KJ, Furman PA, St Clair MH, Lehrman SN, Gallo RC, Bolognesi D, Barry DW, Broder S: 3'-Azido-3'-deoxythymidine (BW A509U): an antiviral agent that inhibits the infectivity and cytopathic effect of human T-lymphotropic virus type III/lymphadenopathy-associated virus in vitro. Proc Natl Acad Sci U S A. 1985 Oct;82(20):7096-100. [PubMed:2413459 ]
Yarchoan R, Mitsuya H, Broder S: AIDS therapies. Sci Am. 1988 Oct;259(4):110-9. [PubMed:3072667 ]
De Clercq E: HIV resistance to reverse transcriptase inhibitors. Biochem Pharmacol. 1994 Jan 20;47(2):155-69. [PubMed:7508227 ]
Connor EM, Sperling RS, Gelber R, Kiselev P, Scott G, O'Sullivan MJ, VanDyke R, Bey M, Shearer W, Jacobson RL, et al.: Reduction of maternal-infant transmission of human immunodeficiency virus type 1 with zidovudine treatment. Pediatric AIDS Clinical Trials Group Protocol 076 Study Group. N Engl J Med. 1994 Nov 3;331(18):1173-80. [PubMed:7935654 ]
Court MH, Krishnaswamy S, Hao Q, Duan SX, Patten CJ, Von Moltke LL, Greenblatt DJ: Evaluation of 3'-azido-3'-deoxythymidine, morphine, and codeine as probe substrates for UDP-glucuronosyltransferase 2B7 (UGT2B7) in human liver microsomes: specificity and influence of the UGT2B7*2 polymorphism. Drug Metab Dispos. 2003 Sep;31(9):1125-33. [PubMed:12920168 ]

Enzymes

Enzyme Details

1. Cytochrome P450 3A4

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

References

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

Enzyme Details

2. Cytochrome P450 2C9

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:: CYP2C9
Uniprot ID:: P11712
Molecular weight:: 55627.365

References

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

Enzyme Details

3. Cytochrome P450 2C19

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:: CYP2C19
Uniprot ID:: P33261
Molecular weight:: 55944.565

References

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

Enzyme Details

4. Cytochrome P450 2C8

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme responsible for the metabolism the anti-cancer drug paclitaxel (taxol).
Gene Name:: CYP2C8
Uniprot ID:: P10632
Molecular weight:: 55824.275

References

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

Enzyme Details

5. Cytochrome P450 2A6

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

References

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

Showing metabocard for Zidovudine (HMDB0014638)

MOL for HMDB0014638 (Zidovudine)

3D MOL for HMDB0014638 (Zidovudine)

3D SDF for HMDB0014638 (Zidovudine)

3D-SDF for HMDB0014638 (Zidovudine)

PDB for HMDB0014638 (Zidovudine)

3D PDB for HMDB0014638 (Zidovudine)

SMILES for HMDB0014638 (Zidovudine)

INCHI for HMDB0014638 (Zidovudine)

Structure for HMDB0014638 (Zidovudine)

3D Structure for HMDB0014638 (Zidovudine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

References

References

References

References

References