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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (10)transporters (3) Show 13 proteins XML

enzymes (10)transporters (3) Show 13 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2022-03-07 02:51:36 UTC

HMDB ID

HMDB0014387

Secondary Accession Numbers

HMDB14387

Metabolite Identification

Common Name

Cladribine

Description

Cladribine is only found in individuals that have used or taken this drug. It is an antineoplastic agent used in the treatment of lymphoproliferative diseases including hairy-cell leukemia. [PubChem]Cladribine is structurally related to fludarabine and pentostatin but has a different mechanism of action. Although the exact mechanism of action has not been fully determined, evidence shows that cladribine is phosphorylated by deoxycytidine kinase to the nucleotidecladribine triphosphate (CdATP; 2-chloro-2â€²-deoxyadenosine 5â€²-triphosphate), which accumulates and is incorporated into DNA in cells such as lymphocytes that contain high levels of deoxycytidine kinase and low levels of deoxynucleotidase, resulting in DNA strand breakage and inhibition of DNA synthesis and repair. High levels of CdATP also appear to inhibit ribonucleotide reductase, which leads to an imbalance in triphosphorylated deoxynucleotide (dNTP) pools and subsequent DNA strand breaks, inhibition of DNA synthesis and repair, nicotinamide adenine dinucleotide (NAD) and ATP depletion, and cell death. Unlike other antimetabolite drugs, cladribine has cytotoxic effects on resting as well as proliferating lymphocytes. However, it does cause cells to accumulate at the G1/S phase junction, suggesting that cytotoxicity is associated with events critical to cell entry into S phase. It also binds purine nucleoside phosphorylase (PNP), however no relationship between this binding and a mechanism of action has been established.

Structure

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

HMDB0014387
     RDKit          3D
Cladribine
 31 33  0  0  0  0  0  0  0  0999 V2000
    5.2033    0.5124    1.2833 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1736    0.5641    0.3079 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4110    0.8856   -0.9698 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4655    0.9448   -1.9185 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8460    1.3742   -3.5799 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.2000    0.6633   -1.5619 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8915    0.3284   -0.2747 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8782    0.2766    0.6701 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2889   -0.0760    1.8345 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9693   -0.2433    1.6373 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7379    0.0073    0.3409 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5387   -0.0477   -0.3315 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0258   -1.4616   -0.5468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5222   -1.3164   -0.2907 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2601   -1.8500   -1.3353 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6703    0.1898   -0.3087 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9622    0.6451    0.3036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9226    2.0473    0.3514 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5514    0.5867    0.4196 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9495   -0.2012    1.1751 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2194    1.1709    2.0935 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2259   -0.5305    2.3961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5125    0.4892   -1.3018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8973   -1.7997   -1.5851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5752   -2.1771    0.1601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8182   -1.7213    0.6853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1553   -2.8111   -1.4376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5393    0.5670   -1.3321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7759    0.3450   -0.3887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1128    0.2093    1.2865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6202    2.4289   -0.2078 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  4  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 16 19  1  0
  8  2  1  0
 19 12  1  0
 11  7  1  0
  1 20  1  0
  1 21  1  0
 10 22  1  0
 12 23  1  6
 13 24  1  0
 13 25  1  0
 14 26  1  1
 15 27  1  0
 16 28  1  6
 17 29  1  0
 17 30  1  0
 18 31  1  0
M  END

242
  Mrv0541 02231214322D          

 19 21  0  0  1  0            999 V2000
    1.6500   -0.5556    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.3467    0.7358    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2852    1.6299    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1323    2.7996    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5741   -0.7167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5741   -2.0446    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.5556    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.7931    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -3.0306    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8305    0.0675    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6170    1.1461    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6155    0.3211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8328    1.4024    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5792    2.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.9681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0556   -1.3806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -1.7931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -2.2056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.9681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 19  1  0  0  0  0
  2 10  1  0  0  0  0
  2 13  1  0  0  0  0
 11  3  1  1  0  0  0
  4 14  1  0  0  0  0
 10  5  1  6  0  0  0
  5 15  1  0  0  0  0
  5 16  1  0  0  0  0
  6 16  2  0  0  0  0
  6 17  1  0  0  0  0
  7 15  2  0  0  0  0
  7 19  1  0  0  0  0
  8 18  1  0  0  0  0
  8 19  2  0  0  0  0
  9 18  1  0  0  0  0
 10 12  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  6  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014387

> <DATABASE_NAME>
hmdb

> <SMILES>
NC1=C2N=CN([C@H]3C[C@H](O)[C@@H](CO)O3)C2=NC(Cl)=N1

> <INCHI_IDENTIFIER>
InChI=1S/C10H12ClN5O3/c11-10-14-8(12)7-9(15-10)16(3-13-7)6-1-4(18)5(2-17)19-6/h3-6,17-18H,1-2H2,(H2,12,14,15)/t4-,5+,6+/m0/s1

> <INCHI_KEY>
PTOAARAWEBMLNO-KVQBGUIXSA-N

> <FORMULA>
C10H12ClN5O3

> <MOLECULAR_WEIGHT>
285.687

> <EXACT_MASS>
285.062866982

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
25.933311613576564

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,3S,5R)-5-(6-amino-2-chloro-9H-purin-9-yl)-2-(hydroxymethyl)oxolan-3-ol

> <ALOGPS_LOGP>
-0.12

> <JCHEM_LOGP>
-0.2817754633333334

> <ALOGPS_LOGS>
-1.65

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.784914754981045

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.886716048865388

> <JCHEM_PKA_STRONGEST_BASIC>
1.3268966303757452

> <JCHEM_POLAR_SURFACE_AREA>
119.30999999999999

> <JCHEM_REFRACTIVITY>
67.18350000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.35e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cladribine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014387
     RDKit          3D
Cladribine
 31 33  0  0  0  0  0  0  0  0999 V2000
    5.2033    0.5124    1.2833 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1736    0.5641    0.3079 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4110    0.8856   -0.9698 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4655    0.9448   -1.9185 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8460    1.3742   -3.5799 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.2000    0.6633   -1.5619 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8915    0.3284   -0.2747 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8782    0.2766    0.6701 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2889   -0.0760    1.8345 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9693   -0.2433    1.6373 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7379    0.0073    0.3409 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5387   -0.0477   -0.3315 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0258   -1.4616   -0.5468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5222   -1.3164   -0.2907 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2601   -1.8500   -1.3353 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6703    0.1898   -0.3087 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9622    0.6451    0.3036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9226    2.0473    0.3514 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5514    0.5867    0.4196 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9495   -0.2012    1.1751 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2194    1.1709    2.0935 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2259   -0.5305    2.3961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5125    0.4892   -1.3018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8973   -1.7997   -1.5851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5752   -2.1771    0.1601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8182   -1.7213    0.6853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1553   -2.8111   -1.4376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5393    0.5670   -1.3321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7759    0.3450   -0.3887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1128    0.2093    1.2865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6202    2.4289   -0.2078 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  4  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 16 19  1  0
  8  2  1  0
 19 12  1  0
 11  7  1  0
  1 20  1  0
  1 21  1  0
 10 22  1  0
 12 23  1  6
 13 24  1  0
 13 25  1  0
 14 26  1  1
 15 27  1  0
 16 28  1  6
 17 29  1  0
 17 30  1  0
 18 31  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 242                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Cl   UNK     0       3.080  -1.037   0.000  0.00  0.00          Cl+0
HETATM    2  O   UNK     0       8.114   1.373   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      11.732   3.042   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       9.580   5.226   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0       8.538  -1.338   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0       8.538  -3.817   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0       5.748  -1.037   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0       4.414  -3.347   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0       5.748  -5.657   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       9.017   0.126   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.485   2.139   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.482   0.599   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.021   2.618   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.548   4.083   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.081  -1.807   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.437  -2.577   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.081  -3.347   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.748  -4.117   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.414  -1.807   0.000  0.00  0.00           C+0
CONECT    1   19                                                            
CONECT    2   10   13                                                       
CONECT    3   11                                                            
CONECT    4   14                                                            
CONECT    5   10   15   16                                                  
CONECT    6   16   17                                                       
CONECT    7   15   19                                                       
CONECT    8   18   19                                                       
CONECT    9   18                                                            
CONECT   10    2    5   12                                                  
CONECT   11    3   12   13                                                  
CONECT   12   10   11                                                       
CONECT   13    2   11   14                                                  
CONECT   14    4   13                                                       
CONECT   15    5    7   17                                                  
CONECT   16    5    6                                                       
CONECT   17    6   15   18                                                  
CONECT   18    8    9   17                                                  
CONECT   19    1    7    8                                                  
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

COMPND    HMDB0014387
HETATM    1  N1  UNL     1       5.203   0.512   1.283  1.00  0.00           N  
HETATM    2  C1  UNL     1       4.174   0.564   0.308  1.00  0.00           C  
HETATM    3  N2  UNL     1       4.411   0.886  -0.970  1.00  0.00           N  
HETATM    4  C2  UNL     1       3.466   0.945  -1.918  1.00  0.00           C  
HETATM    5 CL1  UNL     1       3.846   1.374  -3.580  1.00  0.00          CL  
HETATM    6  N3  UNL     1       2.200   0.663  -1.562  1.00  0.00           N  
HETATM    7  C3  UNL     1       1.892   0.328  -0.275  1.00  0.00           C  
HETATM    8  C4  UNL     1       2.878   0.277   0.670  1.00  0.00           C  
HETATM    9  N4  UNL     1       2.289  -0.076   1.835  1.00  0.00           N  
HETATM   10  C5  UNL     1       0.969  -0.243   1.637  1.00  0.00           C  
HETATM   11  N5  UNL     1       0.738   0.007   0.341  1.00  0.00           N  
HETATM   12  C6  UNL     1      -0.539  -0.048  -0.331  1.00  0.00           C  
HETATM   13  C7  UNL     1      -1.026  -1.462  -0.547  1.00  0.00           C  
HETATM   14  C8  UNL     1      -2.522  -1.316  -0.291  1.00  0.00           C  
HETATM   15  O1  UNL     1      -3.260  -1.850  -1.335  1.00  0.00           O  
HETATM   16  C9  UNL     1      -2.670   0.190  -0.309  1.00  0.00           C  
HETATM   17  C10 UNL     1      -3.962   0.645   0.304  1.00  0.00           C  
HETATM   18  O2  UNL     1      -3.923   2.047   0.351  1.00  0.00           O  
HETATM   19  O3  UNL     1      -1.551   0.587   0.420  1.00  0.00           O  
HETATM   20  H1  UNL     1       5.950  -0.201   1.175  1.00  0.00           H  
HETATM   21  H2  UNL     1       5.219   1.171   2.094  1.00  0.00           H  
HETATM   22  H3  UNL     1       0.226  -0.531   2.396  1.00  0.00           H  
HETATM   23  H4  UNL     1      -0.513   0.489  -1.302  1.00  0.00           H  
HETATM   24  H5  UNL     1      -0.897  -1.800  -1.585  1.00  0.00           H  
HETATM   25  H6  UNL     1      -0.575  -2.177   0.160  1.00  0.00           H  
HETATM   26  H7  UNL     1      -2.818  -1.721   0.685  1.00  0.00           H  
HETATM   27  H8  UNL     1      -3.155  -2.811  -1.438  1.00  0.00           H  
HETATM   28  H9  UNL     1      -2.539   0.567  -1.332  1.00  0.00           H  
HETATM   29  H10 UNL     1      -4.776   0.345  -0.389  1.00  0.00           H  
HETATM   30  H11 UNL     1      -4.113   0.209   1.286  1.00  0.00           H  
HETATM   31  H12 UNL     1      -4.620   2.429  -0.208  1.00  0.00           H  
CONECT    1    2   20   21
CONECT    2    3    3    8
CONECT    3    4
CONECT    4    5    6    6
CONECT    6    7
CONECT    7    8    8   11
CONECT    8    9
CONECT    9   10   10
CONECT   10   11   22
CONECT   11   12
CONECT   12   13   19   23
CONECT   13   14   24   25
CONECT   14   15   16   26
CONECT   15   27
CONECT   16   17   19   28
CONECT   17   18   29   30
CONECT   18   31
END

HMDB0014387
     RDKit          3D
Cladribine
 31 33  0  0  0  0  0  0  0  0999 V2000
    5.2033    0.5124    1.2833 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1736    0.5641    0.3079 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4110    0.8856   -0.9698 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4655    0.9448   -1.9185 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8460    1.3742   -3.5799 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.2000    0.6633   -1.5619 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8915    0.3284   -0.2747 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8782    0.2766    0.6701 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2889   -0.0760    1.8345 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9693   -0.2433    1.6373 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7379    0.0073    0.3409 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5387   -0.0477   -0.3315 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0258   -1.4616   -0.5468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5222   -1.3164   -0.2907 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2601   -1.8500   -1.3353 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6703    0.1898   -0.3087 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9622    0.6451    0.3036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9226    2.0473    0.3514 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5514    0.5867    0.4196 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9495   -0.2012    1.1751 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2194    1.1709    2.0935 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2259   -0.5305    2.3961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5125    0.4892   -1.3018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8973   -1.7997   -1.5851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5752   -2.1771    0.1601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8182   -1.7213    0.6853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1553   -2.8111   -1.4376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5393    0.5670   -1.3321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7759    0.3450   -0.3887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1128    0.2093    1.2865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6202    2.4289   -0.2078 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  4  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 16 19  1  0
  8  2  1  0
 19 12  1  0
 11  7  1  0
  1 20  1  0
  1 21  1  0
 10 22  1  0
 12 23  1  6
 13 24  1  0
 13 25  1  0
 14 26  1  1
 15 27  1  0
 16 28  1  6
 17 29  1  0
 17 30  1  0
 18 31  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(2R,3S,5R)-5-(6-Amino-2-chloropurin-9-yl)-2-(hydroxymethyl)oxolan-3-ol	ChEBI
2-CdA	ChEBI
2-Chloro-2'-deoxy-beta-adenosine	ChEBI
2-Chloro-6-amino-9-(2-deoxy-beta-D-erythro-pentofuranosyl)purine	ChEBI
2-Chloro-deoxyadenosine	ChEBI
2-Chlorodeoxyadenosine	ChEBI
2ClAdo	ChEBI
Cladribina	ChEBI
Cladribinum	ChEBI
CldAdo	ChEBI
Leustatin	Kegg
Mavenclad	Kegg
2-Chloro-2'-deoxy-b-adenosine	Generator
2-Chloro-2'-deoxy-β-adenosine	Generator
2-Chloro-6-amino-9-(2-deoxy-b-D-erythro-pentofuranosyl)purine	Generator
2-Chloro-6-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)purine	Generator
2-Chloro-2'-deoxyadenosine	HMDB
Chlorodeoxyadenosine	HMDB
2'-Deoxy-2-chloroadenosine	HMDB

Chemical Formula

C₁₀H₁₂ClN₅O₃

Average Molecular Weight

285.687

Monoisotopic Molecular Weight

285.062866982

IUPAC Name

(2R,3S,5R)-5-(6-amino-2-chloro-9H-purin-9-yl)-2-(hydroxymethyl)oxolan-3-ol

Traditional Name

cladribine

CAS Registry Number

4291-63-8

SMILES

NC1=C2N=CN([C@H]3C[C@H](O)[C@@H](CO)O3)C2=NC(Cl)=N1

InChI Identifier

InChI=1S/C10H12ClN5O3/c11-10-14-8(12)7-9(15-10)16(3-13-7)6-1-4(18)5(2-17)19-6/h3-6,17-18H,1-2H2,(H2,12,14,15)/t4-,5+,6+/m0/s1

InChI Key

PTOAARAWEBMLNO-KVQBGUIXSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as purine 2'-deoxyribonucleosides. Purine 2'-deoxyribonucleosides are compounds consisting of a purine linked to a ribose which lacks a hydroxyl group at position 2.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Purine nucleosides

Sub Class

Purine 2'-deoxyribonucleosides

Direct Parent

Purine 2'-deoxyribonucleosides

Alternative Parents

Substituents

Purine 2'-deoxyribonucleoside
6-aminopurine
Imidazopyrimidine
Purine
Aminopyrimidine
2-halopyrimidine
Halopyrimidine
N-substituted imidazole
Aryl chloride
Aryl halide
Pyrimidine
Imidolactam
Tetrahydrofuran
Heteroaromatic compound
Imidazole
Azole
Secondary alcohol
Oxacycle
Azacycle
Organoheterocyclic compound
Organohalogen compound
Primary alcohol
Primary amine
Amine
Alcohol
Organic nitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Organochloride
Organonitrogen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organochlorine compound (CHEBI:567361 )
purine 2'-deoxyribonucleoside (CHEBI:567361 )

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: HMDB0014387)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	215 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	6.35 g/L	Not Available
LogP	-0.1	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	6.35 g/L	ALOGPS
logP	-0.12	ALOGPS
logP	-0.28	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	13.89	ChemAxon
pKa (Strongest Basic)	1.33	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	119.31 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	67.18 m³·mol⁻¹	ChemAxon
Polarizability	25.93 Å³	ChemAxon
Number of Rings	3	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
DeepCCS	[M+H]+	163.261	30932474
DeepCCS	[M-H]-	160.903	30932474
DeepCCS	[M-2H]-	194.762	30932474
DeepCCS	[M+Na]+	169.99	30932474
AllCCS	[M+H]+	162.9	32859911
AllCCS	[M+H-H2O]+	159.4	32859911
AllCCS	[M+NH4]+	166.2	32859911
AllCCS	[M+Na]+	167.1	32859911
AllCCS	[M-H]-	160.6	32859911
AllCCS	[M+Na-2H]-	160.2	32859911
AllCCS	[M+HCOO]-	160.0	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	2.25 minutes	32390414
Predicted by Siyang on May 30, 2022	10.2458 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.03 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	77.4 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1323.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	265.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	84.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	165.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	82.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	348.1 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	306.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	126.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	673.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	233.6 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	971.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	202.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	225.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	338.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	215.5 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	76.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Cladribine	NC1=C2N=CN([C@H]3C[C@H](O)[C@@H](CO)O3)C2=NC(Cl)=N1	3430.7	Standard polar	33892256
Cladribine	NC1=C2N=CN([C@H]3C[C@H](O)[C@@H](CO)O3)C2=NC(Cl)=N1	2088.8	Standard non polar	33892256
Cladribine	NC1=C2N=CN([C@H]3C[C@H](O)[C@@H](CO)O3)C2=NC(Cl)=N1	2731.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Cladribine,1TMS,isomer #1	C[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C(N)N=C(Cl)N=C32)O[C@@H]1CO	2664.4	Semi standard non polar	33892256
Cladribine,1TMS,isomer #2	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(N)N=C(Cl)N=C32)C[C@@H]1O	2673.0	Semi standard non polar	33892256
Cladribine,1TMS,isomer #3	C[Si](C)(C)NC1=NC(Cl)=NC2=C1N=CN2[C@H]1C[C@H](O)[C@@H](CO)O1	2717.7	Semi standard non polar	33892256
Cladribine,2TMS,isomer #1	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(N)N=C(Cl)N=C32)C[C@@H]1O[Si](C)(C)C	2621.6	Semi standard non polar	33892256
Cladribine,2TMS,isomer #2	C[Si](C)(C)NC1=NC(Cl)=NC2=C1N=CN2[C@H]1C[C@H](O[Si](C)(C)C)[C@@H](CO)O1	2651.1	Semi standard non polar	33892256
Cladribine,2TMS,isomer #3	C[Si](C)(C)NC1=NC(Cl)=NC2=C1N=CN2[C@H]1C[C@H](O)[C@@H](CO[Si](C)(C)C)O1	2670.5	Semi standard non polar	33892256
Cladribine,2TMS,isomer #4	C[Si](C)(C)N(C1=NC(Cl)=NC2=C1N=CN2[C@H]1C[C@H](O)[C@@H](CO)O1)[Si](C)(C)C	2666.4	Semi standard non polar	33892256
Cladribine,3TMS,isomer #1	C[Si](C)(C)NC1=NC(Cl)=NC2=C1N=CN2[C@H]1C[C@H](O[Si](C)(C)C)[C@@H](CO[Si](C)(C)C)O1	2637.6	Semi standard non polar	33892256
Cladribine,3TMS,isomer #1	C[Si](C)(C)NC1=NC(Cl)=NC2=C1N=CN2[C@H]1C[C@H](O[Si](C)(C)C)[C@@H](CO[Si](C)(C)C)O1	2705.7	Standard non polar	33892256
Cladribine,3TMS,isomer #1	C[Si](C)(C)NC1=NC(Cl)=NC2=C1N=CN2[C@H]1C[C@H](O[Si](C)(C)C)[C@@H](CO[Si](C)(C)C)O1	3724.6	Standard polar	33892256
Cladribine,3TMS,isomer #2	C[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=C(Cl)N=C32)O[C@@H]1CO	2650.2	Semi standard non polar	33892256
Cladribine,3TMS,isomer #2	C[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=C(Cl)N=C32)O[C@@H]1CO	2806.9	Standard non polar	33892256
Cladribine,3TMS,isomer #2	C[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=C(Cl)N=C32)O[C@@H]1CO	3489.9	Standard polar	33892256
Cladribine,3TMS,isomer #3	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=C(Cl)N=C32)C[C@@H]1O	2644.1	Semi standard non polar	33892256
Cladribine,3TMS,isomer #3	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=C(Cl)N=C32)C[C@@H]1O	2839.8	Standard non polar	33892256
Cladribine,3TMS,isomer #3	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=C(Cl)N=C32)C[C@@H]1O	3507.3	Standard polar	33892256
Cladribine,4TMS,isomer #1	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=C(Cl)N=C32)C[C@@H]1O[Si](C)(C)C	2660.8	Semi standard non polar	33892256
Cladribine,4TMS,isomer #1	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=C(Cl)N=C32)C[C@@H]1O[Si](C)(C)C	2828.8	Standard non polar	33892256
Cladribine,4TMS,isomer #1	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=C(Cl)N=C32)C[C@@H]1O[Si](C)(C)C	3211.8	Standard polar	33892256
Cladribine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C(N)N=C(Cl)N=C32)O[C@@H]1CO	2906.4	Semi standard non polar	33892256
Cladribine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(N)N=C(Cl)N=C32)C[C@@H]1O	2924.9	Semi standard non polar	33892256
Cladribine,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC1=NC(Cl)=NC2=C1N=CN2[C@H]1C[C@H](O)[C@@H](CO)O1	2923.2	Semi standard non polar	33892256
Cladribine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(N)N=C(Cl)N=C32)C[C@@H]1O[Si](C)(C)C(C)(C)C	3077.2	Semi standard non polar	33892256
Cladribine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=NC(Cl)=NC2=C1N=CN2[C@H]1C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](CO)O1	3048.5	Semi standard non polar	33892256
Cladribine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC1=NC(Cl)=NC2=C1N=CN2[C@H]1C[C@H](O)[C@@H](CO[Si](C)(C)C(C)(C)C)O1	3063.5	Semi standard non polar	33892256
Cladribine,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N(C1=NC(Cl)=NC2=C1N=CN2[C@H]1C[C@H](O)[C@@H](CO)O1)[Si](C)(C)C(C)(C)C	3033.6	Semi standard non polar	33892256
Cladribine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=NC(Cl)=NC2=C1N=CN2[C@H]1C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](CO[Si](C)(C)C(C)(C)C)O1	3256.8	Semi standard non polar	33892256
Cladribine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=NC(Cl)=NC2=C1N=CN2[C@H]1C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](CO[Si](C)(C)C(C)(C)C)O1	3413.7	Standard non polar	33892256
Cladribine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=NC(Cl)=NC2=C1N=CN2[C@H]1C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](CO[Si](C)(C)C(C)(C)C)O1	3774.6	Standard polar	33892256
Cladribine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=C(Cl)N=C32)O[C@@H]1CO	3190.9	Semi standard non polar	33892256
Cladribine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=C(Cl)N=C32)O[C@@H]1CO	3470.9	Standard non polar	33892256
Cladribine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=C(Cl)N=C32)O[C@@H]1CO	3569.3	Standard polar	33892256
Cladribine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=C(Cl)N=C32)C[C@@H]1O	3188.3	Semi standard non polar	33892256
Cladribine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=C(Cl)N=C32)C[C@@H]1O	3498.3	Standard non polar	33892256
Cladribine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=C(Cl)N=C32)C[C@@H]1O	3604.0	Standard polar	33892256
Cladribine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=C(Cl)N=C32)C[C@@H]1O[Si](C)(C)C(C)(C)C	3383.7	Semi standard non polar	33892256
Cladribine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=C(Cl)N=C32)C[C@@H]1O[Si](C)(C)C(C)(C)C	3647.5	Standard non polar	33892256
Cladribine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=C(Cl)N=C32)C[C@@H]1O[Si](C)(C)C(C)(C)C	3481.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Cladribine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9140000000-2241274903b14d6388f8	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cladribine GC-MS (2 TMS) - 70eV, Positive	splash10-006x-9003100000-a89891be7a06bbd5506c	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cladribine 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 - Cladribine LC-ESI-qTof , Positive-QTOF	splash10-00di-1910000000-ab013e8ee7a199f7832a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cladribine LC-ESI-qTof , Positive-QTOF	splash10-00e9-2900000000-e03a0a91db8b01dbf975	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cladribine , positive-QTOF	splash10-00di-1910000000-ab013e8ee7a199f7832a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cladribine , positive-QTOF	splash10-00e9-2900000000-e03a0a91db8b01dbf975	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cladribine 15V, Negative-QTOF	splash10-001i-0190000000-05b17eee8a4c08986cb6	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cladribine 30V, Negative-QTOF	splash10-001j-0960000000-0d9006c856af92145663	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cladribine 90V, Negative-QTOF	splash10-0159-9800000000-8fab0ce14314864acddb	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cladribine 75V, Negative-QTOF	splash10-001i-3900000000-1e50884799359687c7e6	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cladribine 45V, Negative-QTOF	splash10-001i-0900000000-212e968f1960bfdb6eb9	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cladribine 60V, Negative-QTOF	splash10-001i-1900000000-02d458221e661841d56f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cladribine 35V, Negative-QTOF	splash10-001i-0790000000-67b2d564dceedaaa13f9	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cladribine 90V, Positive-QTOF	splash10-001i-1900000000-a7de88853c9f6d670469	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cladribine 60V, Positive-QTOF	splash10-00di-2900000000-cdfa1c97765dc0e2b44d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cladribine 75V, Positive-QTOF	splash10-0089-1900000000-e6ecaf5468250a1f5477	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cladribine 15V, Positive-QTOF	splash10-00di-0930000000-7147248d1818af3d9fe1	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cladribine 35V, Positive-QTOF	splash10-00di-0900000000-6e9123e18d8f115cbf6f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cladribine 30V, Positive-QTOF	splash10-00di-0900000000-27a9b8fbe0ffb19d00b6	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cladribine 45V, Positive-QTOF	splash10-00di-2900000000-ab1e61284e7768836426	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cladribine 10V, Positive-QTOF	splash10-00di-0920000000-8e9ebddc65823aa84924	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cladribine 20V, Positive-QTOF	splash10-00di-0900000000-0b29ceb8b9b509f8d741	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cladribine 40V, Positive-QTOF	splash10-00di-0900000000-f0f21af02a8d1d299e4a	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cladribine 10V, Negative-QTOF	splash10-00e9-0290000000-7a1cc2a1753c44b0a43d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cladribine 20V, Negative-QTOF	splash10-014i-0910000000-7d61665b0d4c6756760f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cladribine 40V, Negative-QTOF	splash10-00lr-1900000000-345fc7c0125888e844c5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cladribine 10V, Positive-QTOF	splash10-00di-0900000000-fa3ec9f7b8f59958cd43	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane

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 DB00242	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00242	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

DB00242

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

19105

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Cladribine

METLIN ID

Not Available

PubChem Compound

20279

PDB ID

CL9

ChEBI ID

567361

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

Zhenchuk A, Lotfi K, Juliusson G, Albertioni F: Mechanisms of anti-cancer action and pharmacology of clofarabine. Biochem Pharmacol. 2009 Dec 1;78(11):1351-9. doi: 10.1016/j.bcp.2009.06.094. Epub 2009 Jul 1. [PubMed:19576186 ]
Sampat K, Kantarjian H, Borthakur G: Clofarabine: emerging role in leukemias. Expert Opin Investig Drugs. 2009 Oct;18(10):1559-64. doi: 10.1517/13543780903173222. [PubMed:19715446 ]
Kantarjian HM, Jeha S, Gandhi V, Wess M, Faderl S: Clofarabine: past, present, and future. Leuk Lymphoma. 2007 Oct;48(10):1922-30. [PubMed:17852710 ]
Warnke C, Wiendl H, Hartung HP, Stuve O, Kieseier BC: Identification of targets and new developments in the treatment of multiple sclerosis--focus on cladribine. Drug Des Devel Ther. 2010 Jul 21;4:117-26. [PubMed:20689698 ]
Sigal DS, Miller HJ, Schram ED, Saven A: Beyond hairy cell: the activity of cladribine in other hematologic malignancies. Blood. 2010 Oct 21;116(16):2884-96. doi: 10.1182/blood-2010-02-246140. Epub 2010 Jul 15. [PubMed:20634380 ]
Larson ML, Venugopal P: Clofarabine: a new treatment option for patients with acute myeloid leukemia. Expert Opin Pharmacother. 2009 Jun;10(8):1353-7. doi: 10.1517/14656560902997990. [PubMed:19463072 ]
Khalid BA, Hamilton NT, Cauchi MN: Binding of thyroid microsomes by lymphocytes from patients with thyroid disease and normal subjects. Clin Exp Immunol. 1976 Jan;23(1):28-32. [PubMed:1261088 ]
Dimopoulos MA, Weber DM, Kantarjian H, Keating M, Alexanian R: 2Chlorodeoxyadenosine therapy of patients with Waldenstrom macroglobulinemia previously treated with fludarabine. Ann Oncol. 1994 Mar;5(3):288-9. [PubMed:7514439 ]

Only showing the first 10 proteins. There are 13 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Deoxycytidine kinase

General function:: Involved in ATP binding
Specific function:: Required for the phosphorylation of the deoxyribonucleosides deoxycytidine (dC), deoxyguanosine (dG) and deoxyadenosine (dA). Has broad substrate specificity, and does not display selectivity based on the chirality of the substrate. It is also an essential enzyme for the phosphorylation of numerous nucleoside analogs widely employed as antiviral and chemotherapeutic agents.
Gene Name:: DCK
Uniprot ID:: P27707
Molecular weight:: 30518.315

References

Warnke C, Wiendl H, Hartung HP, Stuve O, Kieseier BC: Identification of targets and new developments in the treatment of multiple sclerosis--focus on cladribine. Drug Des Devel Ther. 2010 Jul 21;4:117-26. [PubMed:20689698 ]
Sigal DS, Miller HJ, Schram ED, Saven A: Beyond hairy cell: the activity of cladribine in other hematologic malignancies. Blood. 2010 Oct 21;116(16):2884-96. doi: 10.1182/blood-2010-02-246140. Epub 2010 Jul 15. [PubMed:20634380 ]
Kantarjian HM, Jeha S, Gandhi V, Wess M, Faderl S: Clofarabine: past, present, and future. Leuk Lymphoma. 2007 Oct;48(10):1922-30. [PubMed:17852710 ]
Sampat K, Kantarjian H, Borthakur G: Clofarabine: emerging role in leukemias. Expert Opin Investig Drugs. 2009 Oct;18(10):1559-64. doi: 10.1517/13543780903173222. [PubMed:19715446 ]
Zhenchuk A, Lotfi K, Juliusson G, Albertioni F: Mechanisms of anti-cancer action and pharmacology of clofarabine. Biochem Pharmacol. 2009 Dec 1;78(11):1351-9. doi: 10.1016/j.bcp.2009.06.094. Epub 2009 Jul 1. [PubMed:19576186 ]
Larson ML, Venugopal P: Clofarabine: a new treatment option for patients with acute myeloid leukemia. Expert Opin Pharmacother. 2009 Jun;10(8):1353-7. doi: 10.1517/14656560902997990. [PubMed:19463072 ]

Enzyme Details

2. Ribonucleoside-diphosphate reductase large subunit

General function:: Involved in oxidation reduction
Specific function:: Provides the precursors necessary for DNA synthesis. Catalyzes the biosynthesis of deoxyribonucleotides from the corresponding ribonucleotides.
Gene Name:: RRM1
Uniprot ID:: P23921
Molecular weight:: 90069.375

References

Sampat K, Kantarjian H, Borthakur G: Clofarabine: emerging role in leukemias. Expert Opin Investig Drugs. 2009 Oct;18(10):1559-64. doi: 10.1517/13543780903173222. [PubMed:19715446 ]
Kantarjian HM, Jeha S, Gandhi V, Wess M, Faderl S: Clofarabine: past, present, and future. Leuk Lymphoma. 2007 Oct;48(10):1922-30. [PubMed:17852710 ]
Zhenchuk A, Lotfi K, Juliusson G, Albertioni F: Mechanisms of anti-cancer action and pharmacology of clofarabine. Biochem Pharmacol. 2009 Dec 1;78(11):1351-9. doi: 10.1016/j.bcp.2009.06.094. Epub 2009 Jul 1. [PubMed:19576186 ]
Kline JP, Larson RA: Clofarabine in the treatment of acute myeloid leukaemia and acute lymphoblastic leukaemia: a review. Expert Opin Pharmacother. 2005 Dec;6(15):2711-8. [PubMed:16316309 ]
Takahashi T, Kanazawa J, Akinaga S, Tamaoki T, Okabe M: Antitumor activity of 2-chloro-9-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl) adenine, a novel deoxyadenosine analog, against human colon tumor xenografts by oral administration. Cancer Chemother Pharmacol. 1999;43(3):233-40. [PubMed:9923554 ]

Enzyme Details

3. Ribonucleoside-diphosphate reductase subunit M2

General function:: Involved in oxidoreductase activity
Specific function:: Provides the precursors necessary for DNA synthesis. Catalyzes the biosynthesis of deoxyribonucleotides from the corresponding ribonucleotides. Inhibits Wnt signaling.
Gene Name:: RRM2
Uniprot ID:: P31350
Molecular weight:: 44877.25

References

Sampat K, Kantarjian H, Borthakur G: Clofarabine: emerging role in leukemias. Expert Opin Investig Drugs. 2009 Oct;18(10):1559-64. doi: 10.1517/13543780903173222. [PubMed:19715446 ]
Kantarjian HM, Jeha S, Gandhi V, Wess M, Faderl S: Clofarabine: past, present, and future. Leuk Lymphoma. 2007 Oct;48(10):1922-30. [PubMed:17852710 ]
Zhenchuk A, Lotfi K, Juliusson G, Albertioni F: Mechanisms of anti-cancer action and pharmacology of clofarabine. Biochem Pharmacol. 2009 Dec 1;78(11):1351-9. doi: 10.1016/j.bcp.2009.06.094. Epub 2009 Jul 1. [PubMed:19576186 ]
Kline JP, Larson RA: Clofarabine in the treatment of acute myeloid leukaemia and acute lymphoblastic leukaemia: a review. Expert Opin Pharmacother. 2005 Dec;6(15):2711-8. [PubMed:16316309 ]
Takahashi T, Kanazawa J, Akinaga S, Tamaoki T, Okabe M: Antitumor activity of 2-chloro-9-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl) adenine, a novel deoxyadenosine analog, against human colon tumor xenografts by oral administration. Cancer Chemother Pharmacol. 1999;43(3):233-40. [PubMed:9923554 ]

Enzyme Details

4. DNA polymerase alpha catalytic subunit

General function:: Involved in nucleotide binding
Specific function:: Plays an essential role in the initiation of DNA replication. During the S phase of the cell cycle, the DNA polymerase alpha complex (composed of a catalytic subunit POLA1/p180, a regulatory subunit POLA2/p70 and two primase subunits PRIM1/p49 and PRIM2/p58) is recruited to DNA at the replicative forks via direct interactions with MCM10 and WDHD1. The primase subunit of the polymerase alpha complex initiates DNA synthesis by oligomerising short RNA primers on both leading and lagging strands. These primers are initially extended by the polymerase alpha catalytic subunit and subsequently transferred to polymerase delta and polymerase epsilon for processive synthesis on the lagging and leading strand, respectively. The reason this transfer occurs is because the polymerase alpha has limited processivity and lacks intrinsic 3' exonuclease activity for proofreading error, and therefore is not well suited for replicating long complexes.
Gene Name:: POLA1
Uniprot ID:: P09884
Molecular weight:: 165911.405

References

Zhenchuk A, Lotfi K, Juliusson G, Albertioni F: Mechanisms of anti-cancer action and pharmacology of clofarabine. Biochem Pharmacol. 2009 Dec 1;78(11):1351-9. doi: 10.1016/j.bcp.2009.06.094. Epub 2009 Jul 1. [PubMed:19576186 ]
Kline JP, Larson RA: Clofarabine in the treatment of acute myeloid leukaemia and acute lymphoblastic leukaemia: a review. Expert Opin Pharmacother. 2005 Dec;6(15):2711-8. [PubMed:16316309 ]
Takahashi T, Kanazawa J, Akinaga S, Tamaoki T, Okabe M: Antitumor activity of 2-chloro-9-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl) adenine, a novel deoxyadenosine analog, against human colon tumor xenografts by oral administration. Cancer Chemother Pharmacol. 1999;43(3):233-40. [PubMed:9923554 ]
Hartman WR, Hentosh P: The antileukemia drug 2-chloro-2'-deoxyadenosine: an intrinsic transcriptional antagonist. Mol Pharmacol. 2004 Jan;65(1):227-34. [PubMed:14722255 ]

Enzyme Details

5. DNA polymerase epsilon subunit 4

General function:: Involved in sequence-specific DNA binding
Specific function:: May play a role in allowing polymerase epsilon to carry out its replication and/or repair function.
Gene Name:: POLE4
Uniprot ID:: Q9NR33
Molecular weight:: 12208.63

References

Zhenchuk A, Lotfi K, Juliusson G, Albertioni F: Mechanisms of anti-cancer action and pharmacology of clofarabine. Biochem Pharmacol. 2009 Dec 1;78(11):1351-9. doi: 10.1016/j.bcp.2009.06.094. Epub 2009 Jul 1. [PubMed:19576186 ]

Enzyme Details

6. DNA polymerase epsilon catalytic subunit A

General function:: Involved in nucleotide binding
Specific function:: Participates in DNA repair and in chromosomal DNA replication.
Gene Name:: POLE
Uniprot ID:: Q07864
Molecular weight:: 261515.525

References

Zhenchuk A, Lotfi K, Juliusson G, Albertioni F: Mechanisms of anti-cancer action and pharmacology of clofarabine. Biochem Pharmacol. 2009 Dec 1;78(11):1351-9. doi: 10.1016/j.bcp.2009.06.094. Epub 2009 Jul 1. [PubMed:19576186 ]

Enzyme Details

7. DNA polymerase epsilon subunit 3

General function:: Involved in sequence-specific DNA binding
Specific function:: Forms a complex with DNA polymerase epsilon subunit CHRAC1 and binds naked DNA, which is then incorporated into chromatin, aided by the nucleosome-remodeling activity of ISWI/SNF2H and ACF1.
Gene Name:: POLE3
Uniprot ID:: Q9NRF9
Molecular weight:: 16859.4

References

Zhenchuk A, Lotfi K, Juliusson G, Albertioni F: Mechanisms of anti-cancer action and pharmacology of clofarabine. Biochem Pharmacol. 2009 Dec 1;78(11):1351-9. doi: 10.1016/j.bcp.2009.06.094. Epub 2009 Jul 1. [PubMed:19576186 ]

Enzyme Details

8. DNA polymerase epsilon subunit 2

General function:: Involved in DNA binding
Specific function:: Participates in DNA repair and in chromosomal DNA replication.
Gene Name:: POLE2
Uniprot ID:: P56282
Molecular weight:: 56417.05

References

Zhenchuk A, Lotfi K, Juliusson G, Albertioni F: Mechanisms of anti-cancer action and pharmacology of clofarabine. Biochem Pharmacol. 2009 Dec 1;78(11):1351-9. doi: 10.1016/j.bcp.2009.06.094. Epub 2009 Jul 1. [PubMed:19576186 ]

Enzyme Details

9. Purine nucleoside phosphorylase

General function:: Involved in purine-nucleoside phosphorylase activity
Specific function:: The purine nucleoside phosphorylases catalyze the phosphorolytic breakdown of the N-glycosidic bond in the beta-(deoxy)ribonucleoside molecules, with the formation of the corresponding free purine bases and pentose-1-phosphate.
Gene Name:: PNP
Uniprot ID:: P00491
Molecular weight:: 32117.69

References

Bzowska A, Kazimierczuk Z: 2-Chloro-2'-deoxyadenosine (cladribine) and its analogues are good substrates and potent selective inhibitors of Escherichia coli purine-nucleoside phosphorylase. Eur J Biochem. 1995 Nov 1;233(3):886-90. [PubMed:8521855 ]
Dumontet C, Fabianowska-Majewska K, Mantincic D, Callet Bauchu E, Tigaud I, Gandhi V, Lepoivre M, Peters GJ, Rolland MO, Wyczechowska D, Fang X, Gazzo S, Voorn DA, Vanier-Viornery A, MacKey J: Common resistance mechanisms to deoxynucleoside analogues in variants of the human erythroleukaemic line K562. Br J Haematol. 1999 Jul;106(1):78-85. [PubMed:10444166 ]
Dumontet C, Bauchu EC, Fabianowska K, Lepoivre M, Wyczechowska D, Bodin F, Rolland MO: Common resistance mechanisms to nucleoside analogues in variants of the human erythroleukemic line K562. Adv Exp Med Biol. 1999;457:571-7. [PubMed:10500836 ]
Takimoto T, Kubota M, Tsuruta S, Kitoh T, Tanizawa A, Akiyama Y, Kiriyama Y, Mikawa H: Changes in sensitivity to anticancer drugs during TPA-induced cellular differentiation in a human T-lymphoblastoid cell line (MOLT-4). Leukemia. 1988 Jul;2(7):443-6. [PubMed:3260648 ]
Carson DA, Wasson DB, Lakow E, Kamatani N: Possible metabolic basis for the different immunodeficient states associated with genetic deficiencies of adenosine deaminase and purine nucleoside phosphorylase. Proc Natl Acad Sci U S A. 1982 Jun;79(12):3848-52. [PubMed:6808516 ]

Enzyme Details

10. Ribonucleoside-diphosphate reductase subunit M2 B

General function:: Involved in oxidoreductase activity
Specific function:: Plays a pivotal role in cell survival by repairing damaged DNA in a p53/TP53-dependent manner. Supplies deoxyribonucleotides for DNA repair in cells arrested at G1 or G2. Contains an iron-tyrosyl free radical center required for catalysis. Forms an active ribonucleotide reductase (RNR) complex with RRM1 which is expressed both in resting and proliferating cells in response to DNA damage.
Gene Name:: RRM2B
Uniprot ID:: Q7LG56
Molecular weight:: 48786.6

References

Sampat K, Kantarjian H, Borthakur G: Clofarabine: emerging role in leukemias. Expert Opin Investig Drugs. 2009 Oct;18(10):1559-64. doi: 10.1517/13543780903173222. [PubMed:19715446 ]
Kantarjian HM, Jeha S, Gandhi V, Wess M, Faderl S: Clofarabine: past, present, and future. Leuk Lymphoma. 2007 Oct;48(10):1922-30. [PubMed:17852710 ]
Zhenchuk A, Lotfi K, Juliusson G, Albertioni F: Mechanisms of anti-cancer action and pharmacology of clofarabine. Biochem Pharmacol. 2009 Dec 1;78(11):1351-9. doi: 10.1016/j.bcp.2009.06.094. Epub 2009 Jul 1. [PubMed:19576186 ]
Kline JP, Larson RA: Clofarabine in the treatment of acute myeloid leukaemia and acute lymphoblastic leukaemia: a review. Expert Opin Pharmacother. 2005 Dec;6(15):2711-8. [PubMed:16316309 ]
Takahashi T, Kanazawa J, Akinaga S, Tamaoki T, Okabe M: Antitumor activity of 2-chloro-9-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl) adenine, a novel deoxyadenosine analog, against human colon tumor xenografts by oral administration. Cancer Chemother Pharmacol. 1999;43(3):233-40. [PubMed:9923554 ]

Transporters

Enzyme Details

1. ATP-binding cassette sub-family G member 2

General function:: Involved in ATP binding
Specific function:: Xenobiotic transporter that may play an important role in the exclusion of xenobiotics from the brain. May be involved in brain-to-blood efflux. Appears to play a major role in the multidrug resistance phenotype of several cancer cell lines. When overexpressed, the transfected cells become resistant to mitoxantrone, daunorubicin and doxorubicin, display diminished intracellular accumulation of daunorubicin, and manifest an ATP- dependent increase in the efflux of rhodamine 123
Gene Name:: ABCG2
Uniprot ID:: Q9UNQ0
Molecular weight:: 72313.5

References

de Wolf C, Jansen R, Yamaguchi H, de Haas M, van de Wetering K, Wijnholds J, Beijnen J, Borst P: Contribution of the drug transporter ABCG2 (breast cancer resistance protein) to resistance against anticancer nucleosides. Mol Cancer Ther. 2008 Sep;7(9):3092-102. doi: 10.1158/1535-7163.MCT-08-0427. Epub 2008 Sep 2. [PubMed:18765824 ]

Enzyme Details

2. Solute carrier family 22 member 1

General function:: Involved in ion transmembrane transporter activity
Specific function:: Translocates a broad array of organic cations with various structures and molecular weights including the model compounds 1-methyl-4-phenylpyridinium (MPP), tetraethylammonium (TEA), N-1-methylnicotinamide (NMN), 4-(4-(dimethylamino)styryl)- N-methylpyridinium (ASP), the endogenous compounds choline, guanidine, histamine, epinephrine, adrenaline, noradrenaline and dopamine, and the drugs quinine, and metformin. The transport of organic cations is inhibited by a broad array of compounds like tetramethylammonium (TMA), cocaine, lidocaine, NMDA receptor antagonists, atropine, prazosin, cimetidine, TEA and NMN, guanidine, cimetidine, choline, procainamide, quinine, tetrabutylammonium, and tetrapentylammonium. Translocates organic cations in an electrogenic and pH-independent manner. Translocates organic cations across the plasma membrane in both directions. Transports the polyamines spermine and spermidine. Transports pramipexole across the basolateral membrane of the proximal tubular epithelial cells. The choline transport is activated by MMTS. Regulated by various intracellular signaling pathways including inhibition by protein kinase A activation, and endogenously activation by the calmodulin complex, the calmodulin- dependent kinase II and LCK tyrosine kinase
Gene Name:: SLC22A1
Uniprot ID:: O15245
Molecular weight:: 61187.4

References

Chen R, Nelson JA: Role of organic cation transporters in the renal secretion of nucleosides. Biochem Pharmacol. 2000 Jul 15;60(2):215-9. [PubMed:10825466 ]

Enzyme Details

3. Solute carrier family 22 member 2

General function:: Involved in ion transmembrane transporter activity
Specific function:: Mediates tubular uptake of organic compounds from circulation. Mediates the influx of agmatine, dopamine, noradrenaline (norepinephrine), serotonin, choline, famotidine, ranitidine, histamin, creatinine, amantadine, memantine, acriflavine, 4-[4-(dimethylamino)-styryl]-N-methylpyridinium ASP, amiloride, metformin, N-1-methylnicotinamide (NMN), tetraethylammonium (TEA), 1-methyl-4-phenylpyridinium (MPP), cimetidine, cisplatin and oxaliplatin. Cisplatin may develop a nephrotoxic action. Transport of creatinine is inhibited by fluoroquinolones such as DX-619 and LVFX. This transporter is a major determinant of the anticancer activity of oxaliplatin and may contribute to antitumor specificity
Gene Name:: SLC22A2
Uniprot ID:: O15244
Molecular weight:: 62564.0

References

Chen R, Nelson JA: Role of organic cation transporters in the renal secretion of nucleosides. Biochem Pharmacol. 2000 Jul 15;60(2):215-9. [PubMed:10825466 ]

Only showing the first 10 proteins. There are 13 proteins in total.

Show all enzymes and transporters

Showing metabocard for Cladribine (HMDB0014387)

MOL for HMDB0014387 (Cladribine)

3D MOL for HMDB0014387 (Cladribine)

3D SDF for HMDB0014387 (Cladribine)

3D-SDF for HMDB0014387 (Cladribine)

PDB for HMDB0014387 (Cladribine)

3D PDB for HMDB0014387 (Cladribine)

SMILES for HMDB0014387 (Cladribine)

INCHI for HMDB0014387 (Cladribine)

Structure for HMDB0014387 (Cladribine)

3D Structure for HMDB0014387 (Cladribine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

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Transporters

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