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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:51 UTC

HMDB ID

HMDB0015063

Secondary Accession Numbers

HMDB15063

Metabolite Identification

Common Name

Azacitidine

Description

Azacitidine is only found in individuals that have used or taken this drug. It is a pyrimidine nucleoside analogue that inhibits DNA methyltransferase, impairing DNA methylation. It is also an antimetabolite of cytidine, incorporated primarily into RNA. Azacytidine has been used as an antineoplastic agent. [PubChem]Azacitidine (5-azacytidine) is a chemical analogue of the cytosine nucleoside used in DNA and RNA. Azacitidine is thought to induce antineoplastic activity via two mechanisms; inhibition of DNA methyltransferase at low doses, causing hypomethylation of DNA, and direct cytotoxicity in abnormal hematopoietic cells in the bone marrow through its incorporation into DNA and RNA at high doses, resulting in cell death. As azacitidine is a ribonucleoside, it incoporates into RNA to a larger extent than into DNA. The incorporation into RNA leads to the dissembly of polyribosomes, defective methylation and acceptor function of transfer RNA, and inhibition of the production of protein. Its incorporation into DNA leads to a covalent binding with DNA methyltransferases, which prevents DNA synthesis and subsequent cytotoxicity.

Structure

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

HMDB0015063
     RDKit          3D
Azacitidine
 29 30  0  0  0  0  0  0  0  0999 V2000
    5.2080    0.8006    0.5435 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8331    0.5927    0.2263 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1335   -0.3750    0.8461 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8365   -0.5985    0.5716 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2002    0.1490   -0.3399 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1800   -0.0201   -0.6943 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0019    1.0067   -0.3224 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2775    0.5429   -0.1486 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7031    0.6574    1.3222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0232    0.1610    1.4136 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2791   -0.9439   -0.4723 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4803   -1.0843   -1.8456 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8162   -1.2443   -0.1112 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3849   -2.4232   -0.6865 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8940    1.1154   -0.9605 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3135    1.8411   -1.8317 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2059    1.3500   -0.6906 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5705    1.7593    0.7441 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8714   -0.0223    0.5772 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2672   -1.3731    1.0643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2594   -0.1185   -1.8162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9765    1.1016   -0.7912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0960   -0.0231    1.9518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6520    1.6921    1.6833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6658    0.8138    1.0215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9791   -1.5188    0.1268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3496   -0.2079   -2.3244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7648   -1.2226    0.9772 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5558   -2.4079   -0.9872 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  8 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
  5 15  1  0
 15 16  2  0
 15 17  1  0
 17  2  2  0
 13  6  1  0
  1 18  1  0
  1 19  1  0
  4 20  1  0
  6 21  1  6
  8 22  1  6
  9 23  1  0
  9 24  1  0
 10 25  1  0
 11 26  1  1
 12 27  1  0
 13 28  1  1
 14 29  1  0
M  END

928
  Mrv1652305271900032D          

 17 18  0  0  1  0            999 V2000
    4.1497   -1.0607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0301   -0.8057    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5848   -2.5128    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2002   -2.4265    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0533    0.2492    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4822    0.2492    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7678    1.4868    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1967    1.4868    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4822    2.7243    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8148   -1.0607    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0697   -1.8453    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8947   -1.8453    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4822   -0.5758    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3797   -2.5128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7678    0.6617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1967    0.6617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4822    1.8993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 12  1  0  0  0  0
  1 13  1  0  0  0  0
 10  2  1  1  0  0  0
 11  3  1  1  0  0  0
  4 14  1  0  0  0  0
  5 15  2  0  0  0  0
 13  6  1  6  0  0  0
  6 15  1  0  0  0  0
  6 16  1  0  0  0  0
  7 15  1  0  0  0  0
  7 17  2  0  0  0  0
  8 16  2  0  0  0  0
  8 17  1  0  0  0  0
  9 17  1  0  0  0  0
 10 11  1  0  0  0  0
 10 13  1  0  0  0  0
 11 12  1  0  0  0  0
 12 14  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0015063

> <DATABASE_NAME>
hmdb

> <SMILES>
NC1=NC(=O)N(C=N1)[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C8H12N4O5/c9-7-10-2-12(8(16)11-7)6-5(15)4(14)3(1-13)17-6/h2-6,13-15H,1H2,(H2,9,11,16)/t3-,4-,5-,6-/m1/s1

> <INCHI_KEY>
NMUSYJAQQFHJEW-KVTDHHQDSA-N

> <FORMULA>
C8H12N4O5

> <MOLECULAR_WEIGHT>
244.2047

> <EXACT_MASS>
244.080769514

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
21.49549178558361

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydro-1,3,5-triazin-2-one

> <ALOGPS_LOGP>
-2.45

> <JCHEM_LOGP>
-3.065332952

> <ALOGPS_LOGS>
-1.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.932867726829794

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.551469081388046

> <JCHEM_PKA_STRONGEST_BASIC>
-0.381315609353963

> <JCHEM_POLAR_SURFACE_AREA>
140.97

> <JCHEM_REFRACTIVITY>
52.1932

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.21e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
azacitidine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015063
     RDKit          3D
Azacitidine
 29 30  0  0  0  0  0  0  0  0999 V2000
    5.2080    0.8006    0.5435 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8331    0.5927    0.2263 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1335   -0.3750    0.8461 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8365   -0.5985    0.5716 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2002    0.1490   -0.3399 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1800   -0.0201   -0.6943 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0019    1.0067   -0.3224 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2775    0.5429   -0.1486 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7031    0.6574    1.3222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0232    0.1610    1.4136 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2791   -0.9439   -0.4723 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4803   -1.0843   -1.8456 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8162   -1.2443   -0.1112 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3849   -2.4232   -0.6865 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8940    1.1154   -0.9605 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3135    1.8411   -1.8317 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2059    1.3500   -0.6906 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5705    1.7593    0.7441 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8714   -0.0223    0.5772 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2672   -1.3731    1.0643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2594   -0.1185   -1.8162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9765    1.1016   -0.7912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0960   -0.0231    1.9518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6520    1.6921    1.6833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6658    0.8138    1.0215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9791   -1.5188    0.1268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3496   -0.2079   -2.3244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7648   -1.2226    0.9772 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5558   -2.4079   -0.9872 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  8 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
  5 15  1  0
 15 16  2  0
 15 17  1  0
 17  2  2  0
 13  6  1  0
  1 18  1  0
  1 19  1  0
  4 20  1  0
  6 21  1  6
  8 22  1  6
  9 23  1  0
  9 24  1  0
 10 25  1  0
 11 26  1  1
 12 27  1  0
 13 28  1  1
 14 29  1  0
M  END

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 928                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  O   UNK     0       7.746  -1.980   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       3.790  -1.504   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       4.825  -4.691   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       9.707  -4.529   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       3.833   0.465   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0       6.500   0.465   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0       5.167   2.775   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0       7.834   2.775   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0       6.500   5.085   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       5.254  -1.980   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.730  -3.445   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.270  -3.445   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.500  -1.075   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.175  -4.691   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.167   1.235   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.834   1.235   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.500   3.545   0.000  0.00  0.00           C+0
CONECT    1   12   13                                                       
CONECT    2   10                                                            
CONECT    3   11                                                            
CONECT    4   14                                                            
CONECT    5   15                                                            
CONECT    6   13   15   16                                                  
CONECT    7   15   17                                                       
CONECT    8   16   17                                                       
CONECT    9   17                                                            
CONECT   10    2   11   13                                                  
CONECT   11    3   10   12                                                  
CONECT   12    1   11   14                                                  
CONECT   13    1    6   10                                                  
CONECT   14    4   12                                                       
CONECT   15    5    6    7                                                  
CONECT   16    6    8                                                       
CONECT   17    7    8    9                                                  
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

COMPND    HMDB0015063
HETATM    1  N1  UNL     1       5.208   0.801   0.544  1.00  0.00           N  
HETATM    2  C1  UNL     1       3.833   0.593   0.226  1.00  0.00           C  
HETATM    3  N2  UNL     1       3.134  -0.375   0.846  1.00  0.00           N  
HETATM    4  C2  UNL     1       1.836  -0.598   0.572  1.00  0.00           C  
HETATM    5  N3  UNL     1       1.200   0.149  -0.340  1.00  0.00           N  
HETATM    6  C3  UNL     1      -0.180  -0.020  -0.694  1.00  0.00           C  
HETATM    7  O1  UNL     1      -1.002   1.007  -0.322  1.00  0.00           O  
HETATM    8  C4  UNL     1      -2.278   0.543  -0.149  1.00  0.00           C  
HETATM    9  C5  UNL     1      -2.703   0.657   1.322  1.00  0.00           C  
HETATM   10  O2  UNL     1      -4.023   0.161   1.414  1.00  0.00           O  
HETATM   11  C6  UNL     1      -2.279  -0.944  -0.472  1.00  0.00           C  
HETATM   12  O3  UNL     1      -2.480  -1.084  -1.846  1.00  0.00           O  
HETATM   13  C7  UNL     1      -0.816  -1.244  -0.111  1.00  0.00           C  
HETATM   14  O4  UNL     1      -0.385  -2.423  -0.686  1.00  0.00           O  
HETATM   15  C8  UNL     1       1.894   1.115  -0.960  1.00  0.00           C  
HETATM   16  O5  UNL     1       1.314   1.841  -1.832  1.00  0.00           O  
HETATM   17  N4  UNL     1       3.206   1.350  -0.691  1.00  0.00           N  
HETATM   18  H1  UNL     1       5.571   1.759   0.744  1.00  0.00           H  
HETATM   19  H2  UNL     1       5.871  -0.022   0.577  1.00  0.00           H  
HETATM   20  H3  UNL     1       1.267  -1.373   1.064  1.00  0.00           H  
HETATM   21  H4  UNL     1      -0.259  -0.119  -1.816  1.00  0.00           H  
HETATM   22  H5  UNL     1      -2.976   1.102  -0.791  1.00  0.00           H  
HETATM   23  H6  UNL     1      -2.096  -0.023   1.952  1.00  0.00           H  
HETATM   24  H7  UNL     1      -2.652   1.692   1.683  1.00  0.00           H  
HETATM   25  H8  UNL     1      -4.666   0.814   1.022  1.00  0.00           H  
HETATM   26  H9  UNL     1      -2.979  -1.519   0.127  1.00  0.00           H  
HETATM   27  H10 UNL     1      -2.350  -0.208  -2.324  1.00  0.00           H  
HETATM   28  H11 UNL     1      -0.765  -1.223   0.977  1.00  0.00           H  
HETATM   29  H12 UNL     1       0.556  -2.408  -0.987  1.00  0.00           H  
CONECT    1    2   18   19
CONECT    2    3   17   17
CONECT    3    4    4
CONECT    4    5   20
CONECT    5    6   15
CONECT    6    7   13   21
CONECT    7    8
CONECT    8    9   11   22
CONECT    9   10   23   24
CONECT   10   25
CONECT   11   12   13   26
CONECT   12   27
CONECT   13   14   28
CONECT   14   29
CONECT   15   16   16   17
END

HMDB0015063
     RDKit          3D
Azacitidine
 29 30  0  0  0  0  0  0  0  0999 V2000
    5.2080    0.8006    0.5435 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8331    0.5927    0.2263 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1335   -0.3750    0.8461 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8365   -0.5985    0.5716 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2002    0.1490   -0.3399 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1800   -0.0201   -0.6943 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0019    1.0067   -0.3224 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2775    0.5429   -0.1486 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7031    0.6574    1.3222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0232    0.1610    1.4136 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2791   -0.9439   -0.4723 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4803   -1.0843   -1.8456 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8162   -1.2443   -0.1112 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3849   -2.4232   -0.6865 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8940    1.1154   -0.9605 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3135    1.8411   -1.8317 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2059    1.3500   -0.6906 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5705    1.7593    0.7441 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8714   -0.0223    0.5772 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2672   -1.3731    1.0643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2594   -0.1185   -1.8162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9765    1.1016   -0.7912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0960   -0.0231    1.9518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6520    1.6921    1.6833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6658    0.8138    1.0215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9791   -1.5188    0.1268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3496   -0.2079   -2.3244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7648   -1.2226    0.9772 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5558   -2.4079   -0.9872 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  8 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
  5 15  1  0
 15 16  2  0
 15 17  1  0
 17  2  2  0
 13  6  1  0
  1 18  1  0
  1 19  1  0
  4 20  1  0
  6 21  1  6
  8 22  1  6
  9 23  1  0
  9 24  1  0
 10 25  1  0
 11 26  1  1
 12 27  1  0
 13 28  1  1
 14 29  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
4-Amino-1-beta-D-ribofuranosyl-S-triazin-2(1H)-one	ChEBI
Azacitidina	ChEBI
Azacitidinum	ChEBI
Vidaza	Kegg
4-Amino-1-b-D-ribofuranosyl-S-triazin-2(1H)-one	Generator
4-Amino-1-β-D-ribofuranosyl-S-triazin-2(1H)-one	Generator
5 AZC	HMDB
Azacytidine	HMDB
Pharmion brand OF azacitidine	HMDB
5 Azacytidine	HMDB
Azacitidine	ChEBI

Chemical Formula

C₈H₁₂N₄O₅

Average Molecular Weight

244.2047

Monoisotopic Molecular Weight

244.080769514

IUPAC Name

4-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydro-1,3,5-triazin-2-one

Traditional Name

azacitidine

CAS Registry Number

320-67-2

SMILES

NC1=NC(=O)N(C=N1)[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O

InChI Identifier

InChI=1S/C8H12N4O5/c9-7-10-2-12(8(16)11-7)6-5(15)4(14)3(1-13)17-6/h2-6,13-15H,1H2,(H2,9,11,16)/t3-,4-,5-,6-/m1/s1

InChI Key

NMUSYJAQQFHJEW-KVTDHHQDSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as glycosylamines. Glycosylamines are compounds consisting of an amine with a beta-N-glycosidic bond to a carbohydrate, thus forming a cyclic hemiaminal ether bond (alpha-amino ether).

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Glycosylamines

Alternative Parents

Substituents

N-glycosyl compound
Pentose monosaccharide
Amino-1,3,5-triazine
Aminotriazine
Triazinone
Monosaccharide
Triazine
1,3,5-triazine
Heteroaromatic compound
Tetrahydrofuran
Secondary alcohol
Oxacycle
Azacycle
Organoheterocyclic compound
Amine
Primary amine
Primary alcohol
Alcohol
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic nitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

nucleoside analogue (CHEBI:2038 )
N-glycosyl-1,3,5-triazine (CHEBI:2038 )

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

Cytoplasm (HMDB: HMDB0015063)
Membrane (HMDB: HMDB0015063)

Source

Exogenous

Exogenous (HMDB: HMDB0015063)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	229 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	12.1 g/L	Not Available
LogP	-3.5	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	12.1 g/L	ALOGPS
logP	-2.4	ALOGPS
logP	-3.1	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	12.55	ChemAxon
pKa (Strongest Basic)	-0.38	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	140.97 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	52.19 m³·mol⁻¹	ChemAxon
Polarizability	21.5 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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]+	154.223	31661259
DarkChem	[M-H]-	151.132	31661259
DeepCCS	[M+H]+	151.968	30932474
DeepCCS	[M-H]-	149.573	30932474
DeepCCS	[M-2H]-	183.929	30932474
DeepCCS	[M+Na]+	158.943	30932474
AllCCS	[M+H]+	154.9	32859911
AllCCS	[M+H-H2O]+	151.1	32859911
AllCCS	[M+NH4]+	158.4	32859911
AllCCS	[M+Na]+	159.5	32859911
AllCCS	[M-H]-	151.7	32859911
AllCCS	[M+Na-2H]-	151.5	32859911
AllCCS	[M+HCOO]-	151.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Azacitidine	NC1=NC(=O)N(C=N1)[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O	3603.8	Standard polar	33892256
Azacitidine	NC1=NC(=O)N(C=N1)[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O	2219.0	Standard non polar	33892256
Azacitidine	NC1=NC(=O)N(C=N1)[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O	2597.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Azacitidine,1TMS,isomer #1	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC(N)=NC2=O)[C@H](O)[C@@H]1O	2464.8	Semi standard non polar	33892256
Azacitidine,1TMS,isomer #2	C[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](N2C=NC(N)=NC2=O)[C@@H]1O	2458.3	Semi standard non polar	33892256
Azacitidine,1TMS,isomer #3	C[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C=NC(N)=NC1=O	2450.4	Semi standard non polar	33892256
Azacitidine,1TMS,isomer #4	C[Si](C)(C)NC1=NC(=O)N([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)C=N1	2500.8	Semi standard non polar	33892256
Azacitidine,2TMS,isomer #1	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC(N)=NC2=O)[C@H](O[Si](C)(C)C)[C@@H]1O	2383.4	Semi standard non polar	33892256
Azacitidine,2TMS,isomer #2	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC(N)=NC2=O)[C@H](O)[C@@H]1O[Si](C)(C)C	2379.6	Semi standard non polar	33892256
Azacitidine,2TMS,isomer #3	C[Si](C)(C)NC1=NC(=O)N([C@@H]2O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@H]2O)C=N1	2431.0	Semi standard non polar	33892256
Azacitidine,2TMS,isomer #4	C[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](N2C=NC(N)=NC2=O)[C@@H]1O[Si](C)(C)C	2361.5	Semi standard non polar	33892256
Azacitidine,2TMS,isomer #5	C[Si](C)(C)NC1=NC(=O)N([C@@H]2O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H]2O)C=N1	2443.2	Semi standard non polar	33892256
Azacitidine,2TMS,isomer #6	C[Si](C)(C)NC1=NC(=O)N([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O[Si](C)(C)C)C=N1	2435.2	Semi standard non polar	33892256
Azacitidine,2TMS,isomer #7	C[Si](C)(C)N(C1=NC(=O)N([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)C=N1)[Si](C)(C)C	2427.3	Semi standard non polar	33892256
Azacitidine,3TMS,isomer #1	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC(N)=NC2=O)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	2310.3	Semi standard non polar	33892256
Azacitidine,3TMS,isomer #2	C[Si](C)(C)NC1=NC(=O)N([C@@H]2O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@H]2O[Si](C)(C)C)C=N1	2409.9	Semi standard non polar	33892256
Azacitidine,3TMS,isomer #3	C[Si](C)(C)NC1=NC(=O)N([C@@H]2O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]2O)C=N1	2405.8	Semi standard non polar	33892256
Azacitidine,3TMS,isomer #4	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)[C@H](O)[C@@H]1O	2409.3	Semi standard non polar	33892256
Azacitidine,3TMS,isomer #5	C[Si](C)(C)NC1=NC(=O)N([C@@H]2O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)C=N1	2401.8	Semi standard non polar	33892256
Azacitidine,3TMS,isomer #6	C[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](N2C=NC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)[C@@H]1O	2400.3	Semi standard non polar	33892256
Azacitidine,3TMS,isomer #7	C[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C=NC(N([Si](C)(C)C)[Si](C)(C)C)=NC1=O	2395.1	Semi standard non polar	33892256
Azacitidine,4TMS,isomer #1	C[Si](C)(C)NC1=NC(=O)N([C@@H]2O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)C=N1	2420.8	Semi standard non polar	33892256
Azacitidine,4TMS,isomer #1	C[Si](C)(C)NC1=NC(=O)N([C@@H]2O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)C=N1	2545.8	Standard non polar	33892256
Azacitidine,4TMS,isomer #1	C[Si](C)(C)NC1=NC(=O)N([C@@H]2O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)C=N1	3284.6	Standard polar	33892256
Azacitidine,4TMS,isomer #2	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)[C@H](O[Si](C)(C)C)[C@@H]1O	2432.9	Semi standard non polar	33892256
Azacitidine,4TMS,isomer #2	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)[C@H](O[Si](C)(C)C)[C@@H]1O	2560.6	Standard non polar	33892256
Azacitidine,4TMS,isomer #2	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)[C@H](O[Si](C)(C)C)[C@@H]1O	3062.0	Standard polar	33892256
Azacitidine,4TMS,isomer #3	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)[C@H](O)[C@@H]1O[Si](C)(C)C	2422.2	Semi standard non polar	33892256
Azacitidine,4TMS,isomer #3	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)[C@H](O)[C@@H]1O[Si](C)(C)C	2544.1	Standard non polar	33892256
Azacitidine,4TMS,isomer #3	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)[C@H](O)[C@@H]1O[Si](C)(C)C	3019.2	Standard polar	33892256
Azacitidine,4TMS,isomer #4	C[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](N2C=NC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)[C@@H]1O[Si](C)(C)C	2420.3	Semi standard non polar	33892256
Azacitidine,4TMS,isomer #4	C[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](N2C=NC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)[C@@H]1O[Si](C)(C)C	2561.4	Standard non polar	33892256
Azacitidine,4TMS,isomer #4	C[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](N2C=NC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)[C@@H]1O[Si](C)(C)C	2991.6	Standard polar	33892256
Azacitidine,5TMS,isomer #1	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	2471.4	Semi standard non polar	33892256
Azacitidine,5TMS,isomer #1	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	2551.3	Standard non polar	33892256
Azacitidine,5TMS,isomer #1	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	2819.9	Standard polar	33892256
Azacitidine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC(N)=NC2=O)[C@H](O)[C@@H]1O	2702.5	Semi standard non polar	33892256
Azacitidine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](N2C=NC(N)=NC2=O)[C@@H]1O	2701.2	Semi standard non polar	33892256
Azacitidine,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C=NC(N)=NC1=O	2690.5	Semi standard non polar	33892256
Azacitidine,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NC1=NC(=O)N([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)C=N1	2719.9	Semi standard non polar	33892256
Azacitidine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC(N)=NC2=O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O	2837.8	Semi standard non polar	33892256
Azacitidine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC(N)=NC2=O)[C@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C	2835.2	Semi standard non polar	33892256
Azacitidine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC1=NC(=O)N([C@@H]2O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H]2O)C=N1	2877.2	Semi standard non polar	33892256
Azacitidine,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](N2C=NC(N)=NC2=O)[C@@H]1O[Si](C)(C)C(C)(C)C	2806.8	Semi standard non polar	33892256
Azacitidine,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)NC1=NC(=O)N([C@@H]2O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O)C=N1	2866.9	Semi standard non polar	33892256
Azacitidine,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)NC1=NC(=O)N([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O[Si](C)(C)C(C)(C)C)C=N1	2850.9	Semi standard non polar	33892256
Azacitidine,2TBDMS,isomer #7	CC(C)(C)[Si](C)(C)N(C1=NC(=O)N([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)C=N1)[Si](C)(C)C(C)(C)C	2869.6	Semi standard non polar	33892256
Azacitidine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC(N)=NC2=O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C	3014.4	Semi standard non polar	33892256
Azacitidine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=NC(=O)N([C@@H]2O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H]2O[Si](C)(C)C(C)(C)C)C=N1	3064.5	Semi standard non polar	33892256
Azacitidine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC1=NC(=O)N([C@@H]2O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O)C=N1	3059.1	Semi standard non polar	33892256
Azacitidine,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=O)[C@H](O)[C@@H]1O	3039.2	Semi standard non polar	33892256
Azacitidine,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)NC1=NC(=O)N([C@@H]2O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O[Si](C)(C)C(C)(C)C)C=N1	3046.3	Semi standard non polar	33892256
Azacitidine,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](N2C=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=O)[C@@H]1O	3053.5	Semi standard non polar	33892256
Azacitidine,3TBDMS,isomer #7	CC(C)(C)[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC1=O	3038.2	Semi standard non polar	33892256
Azacitidine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=NC(=O)N([C@@H]2O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O[Si](C)(C)C(C)(C)C)C=N1	3224.0	Semi standard non polar	33892256
Azacitidine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=NC(=O)N([C@@H]2O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O[Si](C)(C)C(C)(C)C)C=N1	3310.6	Standard non polar	33892256
Azacitidine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=NC(=O)N([C@@H]2O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O[Si](C)(C)C(C)(C)C)C=N1	3523.2	Standard polar	33892256
Azacitidine,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O	3249.2	Semi standard non polar	33892256
Azacitidine,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O	3352.7	Standard non polar	33892256
Azacitidine,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O	3338.7	Standard polar	33892256
Azacitidine,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=O)[C@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C	3237.2	Semi standard non polar	33892256
Azacitidine,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=O)[C@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C	3335.5	Standard non polar	33892256
Azacitidine,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=O)[C@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C	3306.1	Standard polar	33892256
Azacitidine,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](N2C=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=O)[C@@H]1O[Si](C)(C)C(C)(C)C	3240.2	Semi standard non polar	33892256
Azacitidine,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](N2C=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=O)[C@@H]1O[Si](C)(C)C(C)(C)C	3342.2	Standard non polar	33892256
Azacitidine,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](N2C=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=O)[C@@H]1O[Si](C)(C)C(C)(C)C	3285.6	Standard polar	33892256
Azacitidine,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C	3423.9	Semi standard non polar	33892256
Azacitidine,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C	3457.6	Standard non polar	33892256
Azacitidine,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C	3241.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Azacitidine GC-MS (Non-derivatized) - 70eV, Positive	splash10-08nc-9420000000-deb4c3c2e01ce611d805	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Azacitidine GC-MS (3 TMS) - 70eV, Positive	splash10-0072-9783700000-4e1593dee5d4eee4fa53	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Azacitidine 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 - Azacitidine 10V, Positive-QTOF	splash10-03di-0910000000-bf3b4f701f0a4e9f2cd8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Azacitidine 20V, Positive-QTOF	splash10-03di-6900000000-5d329d9eaea6433ed7cb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Azacitidine 40V, Positive-QTOF	splash10-03dm-9300000000-9df054033868819ef47c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Azacitidine 10V, Negative-QTOF	splash10-0udl-4690000000-2cfa5eaefe0d852fc770	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Azacitidine 20V, Negative-QTOF	splash10-01ox-9600000000-c47176436749bbaa6201	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Azacitidine 40V, Negative-QTOF	splash10-00l6-9100000000-71ffe7618fd437f42131	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Azacitidine 10V, Positive-QTOF	splash10-03di-0900000000-ad27e26e064f360f3006	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Azacitidine 20V, Positive-QTOF	splash10-03di-4900000000-5d9421c40d3f45d9dc69	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Azacitidine 40V, Positive-QTOF	splash10-03ka-9500000000-79a738f312e868981bd2	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Azacitidine 10V, Negative-QTOF	splash10-01ox-1960000000-94c1bdd861f9dd5e7a9e	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Azacitidine 20V, Negative-QTOF	splash10-0006-9500000000-0f6f7a947b16f6e8119a	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Azacitidine 40V, Negative-QTOF	splash10-00kf-9000000000-6ba499348317121c0ac2	2021-10-11	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00928	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00928	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

DB00928

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

9072

KEGG Compound ID

C11262

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Azacitidine

METLIN ID

Not Available

PubChem Compound

9444

PDB ID

Not Available

ChEBI ID

2038

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

Kaminskas E, Farrell AT, Wang YC, Sridhara R, Pazdur R: FDA drug approval summary: azacitidine (5-azacytidine, Vidaza) for injectable suspension. Oncologist. 2005 Mar;10(3):176-82. [PubMed:15793220 ]
Leone G, Voso MT, Teofili L, Lubbert M: Inhibitors of DNA methylation in the treatment of hematological malignancies and MDS. Clin Immunol. 2003 Oct;109(1):89-102. [PubMed:14585280 ]
Ghoshal K, Bai S: DNA methyltransferases as targets for cancer therapy. Drugs Today (Barc). 2007 Jun;43(6):395-422. [PubMed:17612710 ]
Silverman LR, Demakos EP, Peterson BL, Kornblith AB, Holland JC, Odchimar-Reissig R, Stone RM, Nelson D, Powell BL, DeCastro CM, Ellerton J, Larson RA, Schiffer CA, Holland JF: Randomized controlled trial of azacitidine in patients with the myelodysplastic syndrome: a study of the cancer and leukemia group B. J Clin Oncol. 2002 May 15;20(10):2429-40. [PubMed:12011120 ]
Silverman LR: Targeting hypomethylation of DNA to achieve cellular differentiation in myelodysplastic syndromes (MDS). Oncologist. 2001;6 Suppl 5:8-14. [PubMed:11700387 ]
O'Dwyer K, Maslak P: Azacitidine and the beginnings of therapeutic epigenetic modulation. Expert Opin Pharmacother. 2008 Aug;9(11):1981-6. doi: 10.1517/14656566.9.11.1981 . [PubMed:18627335 ]
Cihak A: Biological effects of 5-azacytidine in eukaryotes. Oncology. 1974;30(5):405-22. [PubMed:4142650 ]
Issa JP, Kantarjian H: Azacitidine. Nat Rev Drug Discov. 2005 May;Suppl:S6-7. [PubMed:15962522 ]
Sullivan M, Hahn K, Kolesar JM: Azacitidine: a novel agent for myelodysplastic syndromes. Am J Health Syst Pharm. 2005 Aug 1;62(15):1567-73. [PubMed:16030365 ]
Siddiqui MA, Scott LJ: Azacitidine: in myelodysplastic syndromes. Drugs. 2005;65(13):1781-9; discussion 1790-1. [PubMed:16114977 ]
Abdulhaq H, Rossetti JM: The role of azacitidine in the treatment of myelodysplastic syndromes. Expert Opin Investig Drugs. 2007 Dec;16(12):1967-75. [PubMed:18042004 ]
Dapp MJ, Clouser CL, Patterson S, Mansky LM: 5-Azacytidine can induce lethal mutagenesis in human immunodeficiency virus type 1. J Virol. 2009 Nov;83(22):11950-8. doi: 10.1128/JVI.01406-09. Epub 2009 Sep 2. [PubMed:19726509 ]
Keating GM: Azacitidine: a review of its use in higher-risk myelodysplastic syndromes/acute myeloid leukaemia. Drugs. 2009;69(17):2501-18. doi: 10.2165/11202840-000000000-00000. [PubMed:19911860 ]

Enzymes

Enzyme Details

1. Cytidine deaminase

General function:: Involved in zinc ion binding
Specific function:: This enzyme scavenge exogenous and endogenous cytidine and 2'-deoxycytidine for UMP synthesis.
Gene Name:: CDA
Uniprot ID:: P32320
Molecular weight:: 16184.545

References

Garcia-Manero G, Stoltz ML, Ward MR, Kantarjian H, Sharma S: A pilot pharmacokinetic study of oral azacitidine. Leukemia. 2008 Sep;22(9):1680-4. doi: 10.1038/leu.2008.145. Epub 2008 Jun 12. [PubMed:18548103 ]

Enzyme Details

2. DNA (cytosine-5)-methyltransferase 1

General function:: Involved in DNA binding
Specific function:: Methylates CpG residues. Preferentially methylates hemimethylated DNA. Associates with DNA replication sites in S phase maintaining the methylation pattern in the newly synthesized strand, that is essential for epigenetic inheritance. Associates with chromatin during G2 and M phases to maintain DNA methylation independently of replication. It is responsible for maintaining methylation patterns established in development. DNA methylation is coordinated with methylation of histones. Mediates transcriptional repression by direct binding to HDAC2. In association with DNMT3B and via the recruitment of CTCFL/BORIS, involved in activation of BAG1 gene expression by modulating dimethylation of promoter histone H3 at H3K4 and H3K9.
Gene Name:: DNMT1
Uniprot ID:: P26358
Molecular weight:: 184817.425

References

Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Kaminskas E, Farrell AT, Wang YC, Sridhara R, Pazdur R: FDA drug approval summary: azacitidine (5-azacytidine, Vidaza) for injectable suspension. Oncologist. 2005 Mar;10(3):176-82. [PubMed:15793220 ]
Cataldo VD, Cortes J, Quintas-Cardama A: Azacitidine for the treatment of myelodysplastic syndrome. Expert Rev Anticancer Ther. 2009 Jul;9(7):875-84. doi: 10.1586/era.09.61. [PubMed:19589026 ]
Leone G, Voso MT, Teofili L, Lubbert M: Inhibitors of DNA methylation in the treatment of hematological malignancies and MDS. Clin Immunol. 2003 Oct;109(1):89-102. [PubMed:14585280 ]
Ghoshal K, Bai S: DNA methyltransferases as targets for cancer therapy. Drugs Today (Barc). 2007 Jun;43(6):395-422. [PubMed:17612710 ]
Silverman LR, Demakos EP, Peterson BL, Kornblith AB, Holland JC, Odchimar-Reissig R, Stone RM, Nelson D, Powell BL, DeCastro CM, Ellerton J, Larson RA, Schiffer CA, Holland JF: Randomized controlled trial of azacitidine in patients with the myelodysplastic syndrome: a study of the cancer and leukemia group B. J Clin Oncol. 2002 May 15;20(10):2429-40. [PubMed:12011120 ]
Fenaux P: Inhibitors of DNA methylation: beyond myelodysplastic syndromes. Nat Clin Pract Oncol. 2005 Dec;2 Suppl 1:S36-44. [PubMed:16341239 ]
Silverman LR: Targeting hypomethylation of DNA to achieve cellular differentiation in myelodysplastic syndromes (MDS). Oncologist. 2001;6 Suppl 5:8-14. [PubMed:11700387 ]
O'Dwyer K, Maslak P: Azacitidine and the beginnings of therapeutic epigenetic modulation. Expert Opin Pharmacother. 2008 Aug;9(11):1981-6. doi: 10.1517/14656566.9.11.1981 . [PubMed:18627335 ]
Hollenbach PW, Nguyen AN, Brady H, Williams M, Ning Y, Richard N, Krushel L, Aukerman SL, Heise C, MacBeth KJ: A comparison of azacitidine and decitabine activities in acute myeloid leukemia cell lines. PLoS One. 2010 Feb 2;5(2):e9001. doi: 10.1371/journal.pone.0009001. [PubMed:20126405 ]
Glover AB, Leyland-Jones B: Biochemistry of azacitidine: a review. Cancer Treat Rep. 1987 Oct;71(10):959-64. [PubMed:2443243 ]

Showing metabocard for Azacitidine (HMDB0015063)

MOL for HMDB0015063 (Azacitidine)

3D MOL for HMDB0015063 (Azacitidine)

3D SDF for HMDB0015063 (Azacitidine)

3D-SDF for HMDB0015063 (Azacitidine)

PDB for HMDB0015063 (Azacitidine)

3D PDB for HMDB0015063 (Azacitidine)

SMILES for HMDB0015063 (Azacitidine)

INCHI for HMDB0015063 (Azacitidine)

Structure for HMDB0015063 (Azacitidine)

3D Structure for HMDB0015063 (Azacitidine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

References

References