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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (3)transporters (1) Show 4 proteins XML

enzymes (3)transporters (1) Show 4 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2022-03-07 02:51:44 UTC

HMDB ID

HMDB0014769

Secondary Accession Numbers

HMDB14769

Metabolite Identification

Common Name

Clofarabine

Description

Clofarabine is a purine nucleoside antimetabolite that is being studied in the treatment of cancer. It is marketed in the U.S. and Canada as Clolar. In Europe and Australia/New Zealand the product is marketed under the name Evoltra. Clofarabine is used in paediatrics to treat a type of leukaemia called relapsed or refractory acute lymphoblastic leukaemia (ALL), only after at least two other types of treatment have failed. It is not known if the drug extends life expectancy. Some investigations of effectiveness in cases of acute myeloid leukaemia (AML) and juvenile myelomonocytic leukaemia (JMML) have been carried out.

Structure

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

HMDB0014769
     RDKit          3D
Clofarabine
 31 33  0  0  0  0  0  0  0  0999 V2000
   -5.0494   -1.7902   -0.2455 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1146   -0.7311   -0.2789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5329    0.5419   -0.4198 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6858    1.5839   -0.4574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2408    3.2385   -0.6411 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.3687    1.3393   -0.3496 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8914    0.0685   -0.2051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7632   -0.9723   -0.1692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0474   -2.0989   -0.0220 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7315   -1.7403    0.0319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6401   -0.4099   -0.0808 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5362    0.3840   -0.0748 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6322   -0.2161   -0.6778 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7621    0.4287   -0.2466 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7742   -0.5811    0.2942 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1386   -1.4926   -0.6915 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3832    1.3172    0.9187 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0994    2.6104    0.4875 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0669    0.6775    1.3144 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3429   -0.4667    2.0223 F   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0742   -1.5805   -0.1120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7923   -2.7763   -0.3449 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0655   -2.4740    0.1493 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3953    1.3739   -0.5724 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2274    1.0483   -1.0493 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6937   -0.0749    0.6384 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3287   -1.1687    1.1200 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0358   -1.8217   -0.4713 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1289    1.2924    1.7300 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9054    3.1139    0.2295 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4161    1.3767    1.8703 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
 15 16  1  0
 14 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
  8  2  1  0
 19 12  1  0
 11  7  1  0
  1 21  1  0
  1 22  1  0
 10 23  1  0
 12 24  1  6
 14 25  1  6
 15 26  1  0
 15 27  1  0
 16 28  1  0
 17 29  1  1
 18 30  1  0
 19 31  1  1
M  END

631
  Mrv0541 02231214502D          

 21 23  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
    6.2821   -0.1650    0.0000 F   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  2  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
    6.2041    0.6198    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1 20  1  0  0  0  0
  2 13  1  0  0  0  0
  3 11  1  0  0  0  0
  3 14  1  0  0  0  0
 12  4  1  1  0  0  0
  5 15  1  0  0  0  0
 11  6  1  6  0  0  0
  6 16  1  0  0  0  0
  6 17  1  0  0  0  0
  7 17  2  0  0  0  0
  7 18  1  0  0  0  0
  8 16  2  0  0  0  0
  8 20  1  0  0  0  0
  9 19  1  0  0  0  0
  9 20  2  0  0  0  0
 10 19  1  0  0  0  0
 11 13  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 13 21  1  1  0  0  0
 14 15  1  6  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014769

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@]1(F)[C@H](O)[C@@H](CO)O[C@H]1N1C=NC2=C(N)N=C(Cl)N=C12

> <INCHI_IDENTIFIER>
InChI=1S/C10H11ClFN5O3/c11-10-15-7(13)5-8(16-10)17(2-14-5)9-4(12)6(19)3(1-18)20-9/h2-4,6,9,18-19H,1H2,(H2,13,15,16)/t3-,4+,6-,9-/m1/s1

> <INCHI_KEY>
WDDPHFBMKLOVOX-AYQXTPAHSA-N

> <FORMULA>
C10H11ClFN5O3

> <MOLECULAR_WEIGHT>
303.677

> <EXACT_MASS>
303.053445155

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
26.059717011373582

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,3R,4S,5R)-5-(6-amino-2-chloro-9H-purin-9-yl)-4-fluoro-2-(hydroxymethyl)oxolan-3-ol

> <ALOGPS_LOGP>
0.32

> <JCHEM_LOGP>
-0.2913217523333334

> <ALOGPS_LOGS>
-1.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.689345889526102

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.70944944602887

> <JCHEM_PKA_STRONGEST_BASIC>
1.3036232523416418

> <JCHEM_POLAR_SURFACE_AREA>
119.30999999999999

> <JCHEM_REFRACTIVITY>
67.00210000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.89e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
clofarabine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014769
     RDKit          3D
Clofarabine
 31 33  0  0  0  0  0  0  0  0999 V2000
   -5.0494   -1.7902   -0.2455 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1146   -0.7311   -0.2789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5329    0.5419   -0.4198 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6858    1.5839   -0.4574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2408    3.2385   -0.6411 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.3687    1.3393   -0.3496 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8914    0.0685   -0.2051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7632   -0.9723   -0.1692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0474   -2.0989   -0.0220 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7315   -1.7403    0.0319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6401   -0.4099   -0.0808 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5362    0.3840   -0.0748 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6322   -0.2161   -0.6778 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7621    0.4287   -0.2466 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7742   -0.5811    0.2942 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1386   -1.4926   -0.6915 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3832    1.3172    0.9187 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0994    2.6104    0.4875 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0669    0.6775    1.3144 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3429   -0.4667    2.0223 F   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0742   -1.5805   -0.1120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7923   -2.7763   -0.3449 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0655   -2.4740    0.1493 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3953    1.3739   -0.5724 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2274    1.0483   -1.0493 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6937   -0.0749    0.6384 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3287   -1.1687    1.1200 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0358   -1.8217   -0.4713 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1289    1.2924    1.7300 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9054    3.1139    0.2295 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4161    1.3767    1.8703 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
 15 16  1  0
 14 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
  8  2  1  0
 19 12  1  0
 11  7  1  0
  1 21  1  0
  1 22  1  0
 10 23  1  0
 12 24  1  6
 14 25  1  6
 15 26  1  0
 15 27  1  0
 16 28  1  0
 17 29  1  1
 18 30  1  0
 19 31  1  1
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 631                                               
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  F   UNK     0      11.727  -0.308   0.000  0.00  0.00           F+0
HETATM    3  O   UNK     0       8.114   1.373   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      11.732   3.042   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       9.580   5.226   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0       8.538  -1.338   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0       8.538  -3.817   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0       5.748  -1.037   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0       4.414  -3.347   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0       5.748  -5.657   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       9.017   0.126   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.485   2.139   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.482   0.599   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.021   2.618   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.548   4.083   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.081  -1.807   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.437  -2.577   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.081  -3.347   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.748  -4.117   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.414  -1.807   0.000  0.00  0.00           C+0
HETATM   21  H   UNK     0      11.581   1.157   0.000  0.00  0.00           H+0
CONECT    1   20                                                            
CONECT    2   13                                                            
CONECT    3   11   14                                                       
CONECT    4   12                                                            
CONECT    5   15                                                            
CONECT    6   11   16   17                                                  
CONECT    7   17   18                                                       
CONECT    8   16   20                                                       
CONECT    9   19   20                                                       
CONECT   10   19                                                            
CONECT   11    3    6   13                                                  
CONECT   12    4   13   14                                                  
CONECT   13    2   11   12   21                                             
CONECT   14    3   12   15                                                  
CONECT   15    5   14                                                       
CONECT   16    6    8   18                                                  
CONECT   17    6    7                                                       
CONECT   18    7   16   19                                                  
CONECT   19    9   10   18                                                  
CONECT   20    1    8    9                                                  
CONECT   21   13                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    HMDB0014769
HETATM    1  N1  UNL     1      -5.049  -1.790  -0.246  1.00  0.00           N  
HETATM    2  C1  UNL     1      -4.115  -0.731  -0.279  1.00  0.00           C  
HETATM    3  N2  UNL     1      -4.533   0.542  -0.420  1.00  0.00           N  
HETATM    4  C2  UNL     1      -3.686   1.584  -0.457  1.00  0.00           C  
HETATM    5 CL1  UNL     1      -4.241   3.239  -0.641  1.00  0.00          CL  
HETATM    6  N3  UNL     1      -2.369   1.339  -0.350  1.00  0.00           N  
HETATM    7  C3  UNL     1      -1.891   0.068  -0.205  1.00  0.00           C  
HETATM    8  C4  UNL     1      -2.763  -0.972  -0.169  1.00  0.00           C  
HETATM    9  N4  UNL     1      -2.047  -2.099  -0.022  1.00  0.00           N  
HETATM   10  C5  UNL     1      -0.731  -1.740   0.032  1.00  0.00           C  
HETATM   11  N5  UNL     1      -0.640  -0.410  -0.081  1.00  0.00           N  
HETATM   12  C6  UNL     1       0.536   0.384  -0.075  1.00  0.00           C  
HETATM   13  O1  UNL     1       1.632  -0.216  -0.678  1.00  0.00           O  
HETATM   14  C7  UNL     1       2.762   0.429  -0.247  1.00  0.00           C  
HETATM   15  C8  UNL     1       3.774  -0.581   0.294  1.00  0.00           C  
HETATM   16  O2  UNL     1       4.139  -1.493  -0.691  1.00  0.00           O  
HETATM   17  C9  UNL     1       2.383   1.317   0.919  1.00  0.00           C  
HETATM   18  O3  UNL     1       2.099   2.610   0.487  1.00  0.00           O  
HETATM   19  C10 UNL     1       1.067   0.677   1.314  1.00  0.00           C  
HETATM   20  F1  UNL     1       1.343  -0.467   2.022  1.00  0.00           F  
HETATM   21  H1  UNL     1      -6.074  -1.580  -0.112  1.00  0.00           H  
HETATM   22  H2  UNL     1      -4.792  -2.776  -0.345  1.00  0.00           H  
HETATM   23  H3  UNL     1       0.066  -2.474   0.149  1.00  0.00           H  
HETATM   24  H4  UNL     1       0.395   1.374  -0.572  1.00  0.00           H  
HETATM   25  H5  UNL     1       3.227   1.048  -1.049  1.00  0.00           H  
HETATM   26  H6  UNL     1       4.694  -0.075   0.638  1.00  0.00           H  
HETATM   27  H7  UNL     1       3.329  -1.169   1.120  1.00  0.00           H  
HETATM   28  H8  UNL     1       5.036  -1.822  -0.471  1.00  0.00           H  
HETATM   29  H9  UNL     1       3.129   1.292   1.730  1.00  0.00           H  
HETATM   30  H10 UNL     1       2.905   3.114   0.230  1.00  0.00           H  
HETATM   31  H11 UNL     1       0.416   1.377   1.870  1.00  0.00           H  
CONECT    1    2   21   22
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   23
CONECT   11   12
CONECT   12   13   19   24
CONECT   13   14
CONECT   14   15   17   25
CONECT   15   16   26   27
CONECT   16   28
CONECT   17   18   19   29
CONECT   18   30
CONECT   19   20   31
END

HMDB0014769
     RDKit          3D
Clofarabine
 31 33  0  0  0  0  0  0  0  0999 V2000
   -5.0494   -1.7902   -0.2455 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1146   -0.7311   -0.2789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5329    0.5419   -0.4198 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6858    1.5839   -0.4574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2408    3.2385   -0.6411 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.3687    1.3393   -0.3496 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8914    0.0685   -0.2051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7632   -0.9723   -0.1692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0474   -2.0989   -0.0220 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7315   -1.7403    0.0319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6401   -0.4099   -0.0808 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5362    0.3840   -0.0748 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6322   -0.2161   -0.6778 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7621    0.4287   -0.2466 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7742   -0.5811    0.2942 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1386   -1.4926   -0.6915 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3832    1.3172    0.9187 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0994    2.6104    0.4875 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0669    0.6775    1.3144 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3429   -0.4667    2.0223 F   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0742   -1.5805   -0.1120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7923   -2.7763   -0.3449 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0655   -2.4740    0.1493 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3953    1.3739   -0.5724 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2274    1.0483   -1.0493 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6937   -0.0749    0.6384 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3287   -1.1687    1.1200 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0358   -1.8217   -0.4713 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1289    1.2924    1.7300 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9054    3.1139    0.2295 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4161    1.3767    1.8703 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
 15 16  1  0
 14 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
  8  2  1  0
 19 12  1  0
 11  7  1  0
  1 21  1  0
  1 22  1  0
 10 23  1  0
 12 24  1  6
 14 25  1  6
 15 26  1  0
 15 27  1  0
 16 28  1  0
 17 29  1  1
 18 30  1  0
 19 31  1  1
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(2R,3R,4S,5R)-5-(6-Amino-2-chloropurin-9-yl)-4-fluoro-2-(hydroxymethyl)oxolan-3-ol	ChEBI
2-Chloro-9-(2'-deoxy-2'-fluoro-beta-D-arabinofuranosyl)adenine	ChEBI
2-Chloro-9-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl)adenine	ChEBI
CAFdA	ChEBI
CL-F-Ara-a	ChEBI
Clofarabina	ChEBI
Clofarabinum	ChEBI
Clolar	Kegg
2-Chloro-9-(2'-deoxy-2'-fluoro-b-D-arabinofuranosyl)adenine	Generator
2-Chloro-9-(2'-deoxy-2'-fluoro-β-D-arabinofuranosyl)adenine	Generator
2-Chloro-9-(2-deoxy-2-fluoro-b-D-arabinofuranosyl)adenine	Generator
2-Chloro-9-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)adenine	Generator
2-Chloro-2'-fluoroarabino-2'-deoxyadenosine	HMDB
2-Chloro-2'-arabino-fluoro-2'-deoxyadenosine	HMDB
2-Chloro-9-(2-deoxy-2-fluoroarabinofuranosyl)adenine	HMDB
2-Chloro-9-(2-deoxy-2-fluoro-beta-D-arbinofuranosyl)adenine	HMDB
Clofarex	HMDB
Evoltra	HMDB
2 Chloro 2' arabino fluoro 2' deoxyadenosine	HMDB
2 Chloro 2' fluoroarabino 2' deoxyadenosine	HMDB

Chemical Formula

C₁₀H₁₁ClFN₅O₃

Average Molecular Weight

303.677

Monoisotopic Molecular Weight

303.053445155

IUPAC Name

(2R,3R,4S,5R)-5-(6-amino-2-chloro-9H-purin-9-yl)-4-fluoro-2-(hydroxymethyl)oxolan-3-ol

Traditional Name

clofarabine

CAS Registry Number

123318-82-1

SMILES

[H][C@]1(F)[C@H](O)[C@@H](CO)O[C@H]1N1C=NC2=C(N)N=C(Cl)N=C12

InChI Identifier

InChI=1S/C10H11ClFN5O3/c11-10-15-7(13)5-8(16-10)17(2-14-5)9-4(12)6(19)3(1-18)20-9/h2-4,6,9,18-19H,1H2,(H2,13,15,16)/t3-,4+,6-,9-/m1/s1

InChI Key

WDDPHFBMKLOVOX-AYQXTPAHSA-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
Aryl chloride
Aryl halide
N-substituted imidazole
Imidolactam
Pyrimidine
Azole
Heteroaromatic compound
Imidazole
Tetrahydrofuran
Secondary alcohol
Fluorohydrin
Halohydrin
Organoheterocyclic compound
Oxacycle
Azacycle
Primary alcohol
Organohalogen compound
Organochloride
Alkyl fluoride
Alcohol
Organofluoride
Organonitrogen compound
Organic nitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Amine
Primary amine
Organooxygen compound
Alkyl halide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organofluorine compound (CHEBI:681569 )
adenosines (CHEBI:681569 )

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: HMDB0014769)
Membrane (HMDB: HMDB0014769)

Source

Exogenous

Exogenous (HMDB: HMDB0014769)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	4.89 g/L	Not Available
LogP	0	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	4.89 g/L	ALOGPS
logP	0.32	ALOGPS
logP	-0.29	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	12.71	ChemAxon
pKa (Strongest Basic)	1.3	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 m³·mol⁻¹	ChemAxon
Polarizability	26.06 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-2H]-	194.003	30932474
DeepCCS	[M+Na]+	168.713	30932474
AllCCS	[M+H]+	166.1	32859911
AllCCS	[M+H-H2O]+	162.7	32859911
AllCCS	[M+NH4]+	169.2	32859911
AllCCS	[M+Na]+	170.0	32859911
AllCCS	[M-H]-	162.0	32859911
AllCCS	[M+Na-2H]-	161.6	32859911
AllCCS	[M+HCOO]-	161.3	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	2.33 minutes	32390414
Predicted by Siyang on May 30, 2022	10.1887 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.37 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	85.0 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1250.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	258.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	81.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	164.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	72.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	337.9 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	294.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	143.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	658.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	215.4 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	958.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	200.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	226.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	345.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	232.6 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	95.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Clofarabine	[H][C@]1(F)[C@H](O)[C@@H](CO)O[C@H]1N1C=NC2=C(N)N=C(Cl)N=C12	3677.4	Standard polar	33892256
Clofarabine	[H][C@]1(F)[C@H](O)[C@@H](CO)O[C@H]1N1C=NC2=C(N)N=C(Cl)N=C12	1842.6	Standard non polar	33892256
Clofarabine	[H][C@]1(F)[C@H](O)[C@@H](CO)O[C@H]1N1C=NC2=C(N)N=C(Cl)N=C12	2634.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Clofarabine,1TMS,isomer #1	C[Si](C)(C)O[C@H]1[C@H](F)[C@H](N2C=NC3=C(N)N=C(Cl)N=C32)O[C@@H]1CO	2592.2	Semi standard non polar	33892256
Clofarabine,1TMS,isomer #2	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(N)N=C(Cl)N=C32)[C@@H](F)[C@@H]1O	2598.4	Semi standard non polar	33892256
Clofarabine,1TMS,isomer #3	C[Si](C)(C)NC1=NC(Cl)=NC2=C1N=CN2[C@@H]1O[C@H](CO)[C@@H](O)[C@@H]1F	2624.4	Semi standard non polar	33892256
Clofarabine,2TMS,isomer #1	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(N)N=C(Cl)N=C32)[C@@H](F)[C@@H]1O[Si](C)(C)C	2563.1	Semi standard non polar	33892256
Clofarabine,2TMS,isomer #2	C[Si](C)(C)NC1=NC(Cl)=NC2=C1N=CN2[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]1F	2555.2	Semi standard non polar	33892256
Clofarabine,2TMS,isomer #3	C[Si](C)(C)NC1=NC(Cl)=NC2=C1N=CN2[C@@H]1O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]1F	2576.7	Semi standard non polar	33892256
Clofarabine,2TMS,isomer #4	C[Si](C)(C)N(C1=NC(Cl)=NC2=C1N=CN2[C@@H]1O[C@H](CO)[C@@H](O)[C@@H]1F)[Si](C)(C)C	2582.7	Semi standard non polar	33892256
Clofarabine,3TMS,isomer #1	C[Si](C)(C)NC1=NC(Cl)=NC2=C1N=CN2[C@@H]1O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1F	2565.6	Semi standard non polar	33892256
Clofarabine,3TMS,isomer #1	C[Si](C)(C)NC1=NC(Cl)=NC2=C1N=CN2[C@@H]1O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1F	2610.5	Standard non polar	33892256
Clofarabine,3TMS,isomer #1	C[Si](C)(C)NC1=NC(Cl)=NC2=C1N=CN2[C@@H]1O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1F	3390.9	Standard polar	33892256
Clofarabine,3TMS,isomer #2	C[Si](C)(C)O[C@H]1[C@H](F)[C@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=C(Cl)N=C32)O[C@@H]1CO	2565.7	Semi standard non polar	33892256
Clofarabine,3TMS,isomer #2	C[Si](C)(C)O[C@H]1[C@H](F)[C@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=C(Cl)N=C32)O[C@@H]1CO	2693.5	Standard non polar	33892256
Clofarabine,3TMS,isomer #2	C[Si](C)(C)O[C@H]1[C@H](F)[C@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=C(Cl)N=C32)O[C@@H]1CO	3164.7	Standard polar	33892256
Clofarabine,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@@H](F)[C@@H]1O	2565.5	Semi standard non polar	33892256
Clofarabine,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@@H](F)[C@@H]1O	2707.1	Standard non polar	33892256
Clofarabine,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@@H](F)[C@@H]1O	3281.5	Standard polar	33892256
Clofarabine,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@@H](F)[C@@H]1O[Si](C)(C)C	2604.1	Semi standard non polar	33892256
Clofarabine,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@@H](F)[C@@H]1O[Si](C)(C)C	2699.3	Standard non polar	33892256
Clofarabine,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@@H](F)[C@@H]1O[Si](C)(C)C	2944.2	Standard polar	33892256
Clofarabine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@H]1[C@H](F)[C@H](N2C=NC3=C(N)N=C(Cl)N=C32)O[C@@H]1CO	2789.5	Semi standard non polar	33892256
Clofarabine,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@@H](F)[C@@H]1O	2818.7	Semi standard non polar	33892256
Clofarabine,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC1=NC(Cl)=NC2=C1N=CN2[C@@H]1O[C@H](CO)[C@@H](O)[C@@H]1F	2817.2	Semi standard non polar	33892256
Clofarabine,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@@H](F)[C@@H]1O[Si](C)(C)C(C)(C)C	2972.8	Semi standard non polar	33892256
Clofarabine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=NC(Cl)=NC2=C1N=CN2[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1F	2949.8	Semi standard non polar	33892256
Clofarabine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC1=NC(Cl)=NC2=C1N=CN2[C@@H]1O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1F	2990.0	Semi standard non polar	33892256
Clofarabine,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N(C1=NC(Cl)=NC2=C1N=CN2[C@@H]1O[C@H](CO)[C@@H](O)[C@@H]1F)[Si](C)(C)C(C)(C)C	2938.5	Semi standard non polar	33892256
Clofarabine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=NC(Cl)=NC2=C1N=CN2[C@@H]1O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1F	3165.6	Semi standard non polar	33892256
Clofarabine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=NC(Cl)=NC2=C1N=CN2[C@@H]1O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1F	3232.0	Standard non polar	33892256
Clofarabine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=NC(Cl)=NC2=C1N=CN2[C@@H]1O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1F	3551.6	Standard polar	33892256
Clofarabine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@H]1[C@H](F)[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	3097.6	Semi standard non polar	33892256
Clofarabine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@H]1[C@H](F)[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	3291.7	Standard non polar	33892256
Clofarabine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@H]1[C@H](F)[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	3368.0	Standard polar	33892256
Clofarabine,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@@H](F)[C@@H]1O	3104.1	Semi standard non polar	33892256
Clofarabine,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@@H](F)[C@@H]1O	3308.0	Standard non polar	33892256
Clofarabine,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@@H](F)[C@@H]1O	3448.4	Standard polar	33892256
Clofarabine,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@@H](F)[C@@H]1O[Si](C)(C)C(C)(C)C	3296.9	Semi standard non polar	33892256
Clofarabine,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@@H](F)[C@@H]1O[Si](C)(C)C(C)(C)C	3453.8	Standard non polar	33892256
Clofarabine,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@@H](F)[C@@H]1O[Si](C)(C)C(C)(C)C	3291.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Clofarabine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9120000000-e007ae055e3973489f73	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Clofarabine GC-MS (2 TMS) - 70eV, Positive	splash10-014i-5932000000-049fdb03acd50f8641cd	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Clofarabine 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 - Clofarabine LC-ESI-qTof , Positive-QTOF	splash10-00di-1903000000-294bd193e470f829e963	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Clofarabine , positive-QTOF	splash10-00di-1903000000-294bd193e470f829e963	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clofarabine 10V, Positive-QTOF	splash10-00di-0900000000-f17f83cd8dba3d2082b9	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clofarabine 20V, Positive-QTOF	splash10-00di-0900000000-34b5bafd796f8fec0b13	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clofarabine 40V, Positive-QTOF	splash10-0ac0-0900000000-640ac0c897663dd584db	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clofarabine 10V, Negative-QTOF	splash10-0udu-0294000000-9ccca97e93ca09d3e79d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clofarabine 20V, Negative-QTOF	splash10-02ai-0930000000-1ebe1a63cd5892cdfd92	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clofarabine 40V, Negative-QTOF	splash10-00lr-4900000000-3c46b8a6d7f8a4613053	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clofarabine 10V, Positive-QTOF	splash10-0udi-0009000000-1af7904d14871bec8a67	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clofarabine 20V, Positive-QTOF	splash10-0fk9-0917000000-15b1ecd2b1188e88b372	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clofarabine 40V, Positive-QTOF	splash10-00di-0900000000-fd24e31d93950d4700af	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clofarabine 10V, Negative-QTOF	splash10-0uxr-0918000000-94af832b5c48122f117c	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clofarabine 20V, Negative-QTOF	splash10-0159-1912000000-7f7acae965d15494a18a	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clofarabine 40V, Negative-QTOF	splash10-001i-1900000000-81c29daed3cbc015348c	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)	2021-09-29	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 DB00631	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00631	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00631

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

106472

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Clofarabine

METLIN ID

Not Available

PubChem Compound

119182

PDB ID

Not Available

ChEBI ID

681569

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 ]
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 ]
Pession A, Masetti R, Kleinschmidt K, Martoni A: Use of clofarabine for acute childhood leukemia. Biologics. 2010 Jun 24;4:111-8. [PubMed:20631817 ]
Harned TM, Gaynon PS: Treating refractory leukemias in childhood, role of clofarabine. Ther Clin Risk Manag. 2008 Apr;4(2):327-36. [PubMed:18728851 ]
Lech-Maranda E, Korycka A, Robak T: Clofarabine as a novel nucleoside analogue approved to treat patients with haematological malignancies: mechanism of action and clinical activity. Mini Rev Med Chem. 2009 Jun;9(7):805-12. [PubMed:19519505 ]

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

Pession A, Masetti R, Kleinschmidt K, Martoni A: Use of clofarabine for acute childhood leukemia. Biologics. 2010 Jun 24;4:111-8. [PubMed:20631817 ]
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 ]
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 ]

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

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Pession A, Masetti R, Kleinschmidt K, Martoni A: Use of clofarabine for acute childhood leukemia. Biologics. 2010 Jun 24;4:111-8. [PubMed:20631817 ]
Authors unspecified: Clofarabine. Drugs R D. 2004;5(4):213-7. [PubMed:15230627 ]
Musto P, Ferrara F: Clofarabine: in search of combinations for the treatment of patients with high-risk acute myeloid leukemia. Cancer. 2008 Oct 15;113(8):1995-8. doi: 10.1002/cncr.23804. [PubMed:18780321 ]
Harned TM, Gaynon PS: Treating refractory leukemias in childhood, role of clofarabine. Ther Clin Risk Manag. 2008 Apr;4(2):327-36. [PubMed:18728851 ]
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 ]
Lech-Maranda E, Korycka A, Robak T: Clofarabine as a novel nucleoside analogue approved to treat patients with haematological malignancies: mechanism of action and clinical activity. Mini Rev Med Chem. 2009 Jun;9(7):805-12. [PubMed:19519505 ]
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

3. 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

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Pession A, Masetti R, Kleinschmidt K, Martoni A: Use of clofarabine for acute childhood leukemia. Biologics. 2010 Jun 24;4:111-8. [PubMed:20631817 ]
Authors unspecified: Clofarabine. Drugs R D. 2004;5(4):213-7. [PubMed:15230627 ]
Musto P, Ferrara F: Clofarabine: in search of combinations for the treatment of patients with high-risk acute myeloid leukemia. Cancer. 2008 Oct 15;113(8):1995-8. doi: 10.1002/cncr.23804. [PubMed:18780321 ]
Harned TM, Gaynon PS: Treating refractory leukemias in childhood, role of clofarabine. Ther Clin Risk Manag. 2008 Apr;4(2):327-36. [PubMed:18728851 ]
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 ]
Lech-Maranda E, Korycka A, Robak T: Clofarabine as a novel nucleoside analogue approved to treat patients with haematological malignancies: mechanism of action and clinical activity. Mini Rev Med Chem. 2009 Jun;9(7):805-12. [PubMed:19519505 ]
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 ]

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 ]

Showing metabocard for Clofarabine (HMDB0014769)

MOL for HMDB0014769 (Clofarabine)

3D MOL for HMDB0014769 (Clofarabine)

3D SDF for HMDB0014769 (Clofarabine)

3D-SDF for HMDB0014769 (Clofarabine)

PDB for HMDB0014769 (Clofarabine)

3D PDB for HMDB0014769 (Clofarabine)

SMILES for HMDB0014769 (Clofarabine)

INCHI for HMDB0014769 (Clofarabine)

Structure for HMDB0014769 (Clofarabine)

3D Structure for HMDB0014769 (Clofarabine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

References

References

References

Transporters

References