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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:52 UTC

Update Date

2022-03-07 02:51:58 UTC

HMDB ID

HMDB0015401

Secondary Accession Numbers

HMDB15401

Metabolite Identification

Common Name

Nelarabine

Description

Nelarabine is only found in individuals that have used or taken this drug. It is a chemotherapy drug used in T-cell acute lymphoblastic leukemia. Nelarabine is a purine nucleoside analog converted to its corresponding arabinosylguanine nucleotide triphosphate (araGTP), resulting in inhibition of DNA synthesis and cytotoxicity.Once nelarabine is metabolized into ara-GTP, the metabolite accumulates in leukemic blasts and incorporates into DNA to exert its S phase-specific cytotoxic effects, leading to the induction of fragmentation and apoptosis. Ara-GTP competes with endogenous deoxyGTP (dGTP) for incorporation into DNA. Once ara-GTP is incorporated at the 3' end of DNA, further DNA elongation is inhibited, which signals apoptosis and leads to cellular destruction. Additional cytotoxic activities may exist, but these are not fully understood.

Structure

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

HMDB0015401
     RDKit          3D
Nelarabine
 36 38  0  0  0  0  0  0  0  0999 V2000
    5.8016    0.8818    0.2368 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4831    1.3635    0.2216 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4128    0.5063    0.4370 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5723   -0.7932    0.6652 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5107   -1.5941    0.8698 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7545   -2.9699    1.1073 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2517   -1.1185    0.8525 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0274    0.1779    0.6285 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1178    1.0041    0.4176 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6483    2.2419    0.2178 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3061    2.1978    0.2999 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0761    0.9235    0.5533 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4361    0.5189    0.7021 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6764   -0.7857    0.2897 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0113   -0.8835   -0.0399 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1426   -1.7166   -1.3025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4916   -1.8349   -1.6646 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5453    0.4932   -0.2679 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2741    0.8751    0.8570 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2738    1.3143   -0.2807 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6491    1.3061   -1.5079 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0819    0.6532   -0.8243 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5212    1.6133    0.6473 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9226   -0.0638    0.8044 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3767   -3.7210    0.4916 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3283   -3.2572    1.9197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3632    3.0626    0.1791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8412    0.7338    1.7122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5778   -1.4150    0.7660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5424   -1.3091   -2.1282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7831   -2.7412   -1.0553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0701   -1.2059   -1.1665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1248    0.6014   -1.2016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0111    1.7735    1.1463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4458    2.3527    0.0682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7809    0.8145   -1.4937 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 15 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
  9  3  1  0
 20 13  1  0
 12  8  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  6 25  1  0
  6 26  1  0
 11 27  1  0
 13 28  1  1
 15 29  1  1
 16 30  1  0
 16 31  1  0
 17 32  1  0
 18 33  1  6
 19 34  1  0
 20 35  1  1
 21 36  1  0
M  END

1280
  Mrv0541 02231215222D          

 21 23  0  0  1  0            999 V2000
    4.7896    0.8142    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7251   -0.0866    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7282    1.7083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5752    2.8780    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -2.9522    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0171   -0.6383    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0171   -1.9662    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -0.4772    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -1.7147    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930   -0.4772    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0585    0.3995    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2734    0.1459    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0599    1.2245    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2757    1.4808    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0221    2.2659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365   -0.8897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4986   -1.3022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365   -1.7147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -2.1272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -0.8897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -3.3647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 12  1  0  0  0  0
  1 14  1  0  0  0  0
 11  2  1  6  0  0  0
 13  3  1  1  0  0  0
  4 15  1  0  0  0  0
  5 19  1  0  0  0  0
  5 21  1  0  0  0  0
 12  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  1  0  0  0  0
  8 20  2  0  0  0  0
  9 19  2  0  0  0  0
  9 20  1  0  0  0  0
 10 20  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 16 18  2  0  0  0  0
 18 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015401

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=NC(N)=NC2=C1N=CN2[C@@H]1O[C@H](CO)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C11H15N5O5/c1-20-9-5-8(14-11(12)15-9)16(3-13-5)10-7(19)6(18)4(2-17)21-10/h3-4,6-7,10,17-19H,2H2,1H3,(H2,12,14,15)/t4-,6-,7+,10-/m1/s1

> <INCHI_KEY>
IXOXBSCIXZEQEQ-UHTZMRCNSA-N

> <FORMULA>
C11H15N5O5

> <MOLECULAR_WEIGHT>
297.2673

> <EXACT_MASS>
297.107318615

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_AVERAGE_POLARIZABILITY>
27.6764895822293

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3S,4S,5R)-2-(2-amino-6-methoxy-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol

> <ALOGPS_LOGP>
-0.81

> <JCHEM_LOGP>
-1.5698491153333332

> <ALOGPS_LOGS>
-1.33

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.889268678015117

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.453927438840978

> <JCHEM_PKA_STRONGEST_BASIC>
3.470474307307819

> <JCHEM_POLAR_SURFACE_AREA>
148.77

> <JCHEM_REFRACTIVITY>
69.60480000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.39e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
nelarabine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015401
     RDKit          3D
Nelarabine
 36 38  0  0  0  0  0  0  0  0999 V2000
    5.8016    0.8818    0.2368 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4831    1.3635    0.2216 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4128    0.5063    0.4370 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5723   -0.7932    0.6652 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5107   -1.5941    0.8698 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7545   -2.9699    1.1073 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2517   -1.1185    0.8525 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0274    0.1779    0.6285 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1178    1.0041    0.4176 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6483    2.2419    0.2178 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3061    2.1978    0.2999 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0761    0.9235    0.5533 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4361    0.5189    0.7021 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6764   -0.7857    0.2897 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0113   -0.8835   -0.0399 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1426   -1.7166   -1.3025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4916   -1.8349   -1.6646 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5453    0.4932   -0.2679 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2741    0.8751    0.8570 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2738    1.3143   -0.2807 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6491    1.3061   -1.5079 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0819    0.6532   -0.8243 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5212    1.6133    0.6473 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9226   -0.0638    0.8044 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3767   -3.7210    0.4916 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3283   -3.2572    1.9197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3632    3.0626    0.1791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8412    0.7338    1.7122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5778   -1.4150    0.7660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5424   -1.3091   -2.1282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7831   -2.7412   -1.0553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0701   -1.2059   -1.1665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1248    0.6014   -1.2016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0111    1.7735    1.1463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4458    2.3527    0.0682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7809    0.8145   -1.4937 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 15 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
  9  3  1  0
 20 13  1  0
 12  8  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  6 25  1  0
  6 26  1  0
 11 27  1  0
 13 28  1  1
 15 29  1  1
 16 30  1  0
 16 31  1  0
 17 32  1  0
 18 33  1  6
 19 34  1  0
 20 35  1  1
 21 36  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1280                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       8.941   1.520   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      12.554  -0.162   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      12.559   3.189   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      10.407   5.372   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       6.574  -5.511   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0       9.365  -1.191   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0       9.365  -3.670   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0       6.574  -0.891   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0       5.241  -3.201   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0       3.907  -0.891   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0      11.309   0.746   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.844   0.272   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.312   2.286   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.848   2.764   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.375   4.230   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.908  -1.661   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.264  -2.431   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.908  -3.201   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.574  -3.971   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.241  -1.661   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.241  -6.281   0.000  0.00  0.00           C+0
CONECT    1   12   14                                                       
CONECT    2   11                                                            
CONECT    3   13                                                            
CONECT    4   15                                                            
CONECT    5   19   21                                                       
CONECT    6   12   16   17                                                  
CONECT    7   17   18                                                       
CONECT    8   16   20                                                       
CONECT    9   19   20                                                       
CONECT   10   20                                                            
CONECT   11    2   12   13                                                  
CONECT   12    1    6   11                                                  
CONECT   13    3   11   14                                                  
CONECT   14    1   13   15                                                  
CONECT   15    4   14                                                       
CONECT   16    6    8   18                                                  
CONECT   17    6    7                                                       
CONECT   18    7   16   19                                                  
CONECT   19    5    9   18                                                  
CONECT   20    8    9   10                                                  
CONECT   21    5                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    HMDB0015401
HETATM    1  C1  UNL     1       5.802   0.882   0.237  1.00  0.00           C  
HETATM    2  O1  UNL     1       4.483   1.364   0.222  1.00  0.00           O  
HETATM    3  C2  UNL     1       3.413   0.506   0.437  1.00  0.00           C  
HETATM    4  N1  UNL     1       3.572  -0.793   0.665  1.00  0.00           N  
HETATM    5  C3  UNL     1       2.511  -1.594   0.870  1.00  0.00           C  
HETATM    6  N2  UNL     1       2.754  -2.970   1.107  1.00  0.00           N  
HETATM    7  N3  UNL     1       1.252  -1.118   0.853  1.00  0.00           N  
HETATM    8  C4  UNL     1       1.027   0.178   0.628  1.00  0.00           C  
HETATM    9  C5  UNL     1       2.118   1.004   0.418  1.00  0.00           C  
HETATM   10  N4  UNL     1       1.648   2.242   0.218  1.00  0.00           N  
HETATM   11  C6  UNL     1       0.306   2.198   0.300  1.00  0.00           C  
HETATM   12  N5  UNL     1      -0.076   0.924   0.553  1.00  0.00           N  
HETATM   13  C7  UNL     1      -1.436   0.519   0.702  1.00  0.00           C  
HETATM   14  O2  UNL     1      -1.676  -0.786   0.290  1.00  0.00           O  
HETATM   15  C8  UNL     1      -3.011  -0.883  -0.040  1.00  0.00           C  
HETATM   16  C9  UNL     1      -3.143  -1.717  -1.302  1.00  0.00           C  
HETATM   17  O3  UNL     1      -4.492  -1.835  -1.665  1.00  0.00           O  
HETATM   18  C10 UNL     1      -3.545   0.493  -0.268  1.00  0.00           C  
HETATM   19  O4  UNL     1      -4.274   0.875   0.857  1.00  0.00           O  
HETATM   20  C11 UNL     1      -2.274   1.314  -0.281  1.00  0.00           C  
HETATM   21  O5  UNL     1      -1.649   1.306  -1.508  1.00  0.00           O  
HETATM   22  H1  UNL     1       6.082   0.653  -0.824  1.00  0.00           H  
HETATM   23  H2  UNL     1       6.521   1.613   0.647  1.00  0.00           H  
HETATM   24  H3  UNL     1       5.923  -0.064   0.804  1.00  0.00           H  
HETATM   25  H4  UNL     1       2.377  -3.721   0.492  1.00  0.00           H  
HETATM   26  H5  UNL     1       3.328  -3.257   1.920  1.00  0.00           H  
HETATM   27  H6  UNL     1      -0.363   3.063   0.179  1.00  0.00           H  
HETATM   28  H7  UNL     1      -1.841   0.734   1.712  1.00  0.00           H  
HETATM   29  H8  UNL     1      -3.578  -1.415   0.766  1.00  0.00           H  
HETATM   30  H9  UNL     1      -2.542  -1.309  -2.128  1.00  0.00           H  
HETATM   31  H10 UNL     1      -2.783  -2.741  -1.055  1.00  0.00           H  
HETATM   32  H11 UNL     1      -5.070  -1.206  -1.167  1.00  0.00           H  
HETATM   33  H12 UNL     1      -4.125   0.601  -1.202  1.00  0.00           H  
HETATM   34  H13 UNL     1      -4.011   1.773   1.146  1.00  0.00           H  
HETATM   35  H14 UNL     1      -2.446   2.353   0.068  1.00  0.00           H  
HETATM   36  H15 UNL     1      -0.781   0.815  -1.494  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3
CONECT    3    4    4    9
CONECT    4    5
CONECT    5    6    7    7
CONECT    6   25   26
CONECT    7    8
CONECT    8    9    9   12
CONECT    9   10
CONECT   10   11   11
CONECT   11   12   27
CONECT   12   13
CONECT   13   14   20   28
CONECT   14   15
CONECT   15   16   18   29
CONECT   16   17   30   31
CONECT   17   32
CONECT   18   19   20   33
CONECT   19   34
CONECT   20   21   35
CONECT   21   36
END

HMDB0015401
     RDKit          3D
Nelarabine
 36 38  0  0  0  0  0  0  0  0999 V2000
    5.8016    0.8818    0.2368 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4831    1.3635    0.2216 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4128    0.5063    0.4370 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5723   -0.7932    0.6652 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5107   -1.5941    0.8698 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7545   -2.9699    1.1073 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2517   -1.1185    0.8525 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0274    0.1779    0.6285 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1178    1.0041    0.4176 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6483    2.2419    0.2178 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3061    2.1978    0.2999 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0761    0.9235    0.5533 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4361    0.5189    0.7021 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6764   -0.7857    0.2897 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0113   -0.8835   -0.0399 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1426   -1.7166   -1.3025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4916   -1.8349   -1.6646 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5453    0.4932   -0.2679 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2741    0.8751    0.8570 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2738    1.3143   -0.2807 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6491    1.3061   -1.5079 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0819    0.6532   -0.8243 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5212    1.6133    0.6473 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9226   -0.0638    0.8044 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3767   -3.7210    0.4916 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3283   -3.2572    1.9197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3632    3.0626    0.1791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8412    0.7338    1.7122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5778   -1.4150    0.7660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5424   -1.3091   -2.1282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7831   -2.7412   -1.0553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0701   -1.2059   -1.1665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1248    0.6014   -1.2016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0111    1.7735    1.1463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4458    2.3527    0.0682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7809    0.8145   -1.4937 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 15 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
  9  3  1  0
 20 13  1  0
 12  8  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  6 25  1  0
  6 26  1  0
 11 27  1  0
 13 28  1  1
 15 29  1  1
 16 30  1  0
 16 31  1  0
 17 32  1  0
 18 33  1  6
 19 34  1  0
 20 35  1  1
 21 36  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2-Amino-9-beta-D-arabinofuranosyl-6-methoxy-9H-purine	ChEBI
Arranon	ChEBI
Nelzarabine	ChEBI
2-Amino-9-b-D-arabinofuranosyl-6-methoxy-9H-purine	Generator
2-Amino-9-β-D-arabinofuranosyl-6-methoxy-9H-purine	Generator
GW-506U78	HMDB
Compound 506u78	HMDB
2-Amino-6-methoxypurine arabinoside	HMDB
GlaxoSmithKline brand OF nelarabine	HMDB

Chemical Formula

C₁₁H₁₅N₅O₅

Average Molecular Weight

297.2673

Monoisotopic Molecular Weight

297.107318615

IUPAC Name

(2R,3S,4S,5R)-2-(2-amino-6-methoxy-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol

Traditional Name

nelarabine

CAS Registry Number

121032-29-9

SMILES

COC1=NC(N)=NC2=C1N=CN2[C@@H]1O[C@H](CO)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C11H15N5O5/c1-20-9-5-8(14-11(12)15-9)16(3-13-5)10-7(19)6(18)4(2-17)21-10/h3-4,6-7,10,17-19H,2H2,1H3,(H2,12,14,15)/t4-,6-,7+,10-/m1/s1

InChI Key

IXOXBSCIXZEQEQ-UHTZMRCNSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as purine nucleosides. Purine nucleosides are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Purine nucleosides

Sub Class

Not Available

Direct Parent

Purine nucleosides

Alternative Parents

Substituents

Purine nucleoside
Glycosyl compound
N-glycosyl compound
Hypoxanthine
Pentose monosaccharide
Purine
Imidazopyrimidine
Aminopyrimidine
Alkyl aryl ether
Pyrimidine
Monosaccharide
N-substituted imidazole
Heteroaromatic compound
Azole
Tetrahydrofuran
Imidazole
Secondary alcohol
Oxacycle
Azacycle
Organoheterocyclic compound
Ether
Organopnictogen compound
Alcohol
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Amine
Primary amine
Primary alcohol
Organooxygen compound
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

purine nucleoside (CHEBI:63612 )
monosaccharide derivative (CHEBI:63612 )
beta-D-arabinoside (CHEBI:63612 )

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: HMDB0015401)

Source

Exogenous

Exogenous (HMDB: HMDB0015401)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	209 - 217 °C (decomposition)	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	13.9 g/L	Not Available
LogP	-1	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	13.9 g/L	ALOGPS
logP	-0.81	ALOGPS
logP	-1.6	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	12.45	ChemAxon
pKa (Strongest Basic)	3.47	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	148.77 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	69.6 m³·mol⁻¹	ChemAxon
Polarizability	27.68 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	167.743	31661259
DarkChem	[M-H]-	161.685	31661259
DeepCCS	[M+H]+	162.288	30932474
DeepCCS	[M-H]-	159.892	30932474
DeepCCS	[M-2H]-	194.149	30932474
DeepCCS	[M+Na]+	169.192	30932474
AllCCS	[M+H]+	168.1	32859911
AllCCS	[M+H-H2O]+	164.7	32859911
AllCCS	[M+NH4]+	171.2	32859911
AllCCS	[M+Na]+	172.1	32859911
AllCCS	[M-H]-	167.0	32859911
AllCCS	[M+Na-2H]-	166.6	32859911
AllCCS	[M+HCOO]-	166.2	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.	2.32 minutes	32390414
Predicted by Siyang on May 30, 2022	9.8033 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	4.68 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	165.6 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1096.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	223.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	71.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	154.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	64.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	325.0 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	284.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	593.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	614.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	123.8 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	857.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	175.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	177.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	540.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	355.2 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	164.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Nelarabine	COC1=NC(N)=NC2=C1N=CN2[C@@H]1O[C@H](CO)[C@@H](O)[C@@H]1O	3504.7	Standard polar	33892256
Nelarabine	COC1=NC(N)=NC2=C1N=CN2[C@@H]1O[C@H](CO)[C@@H](O)[C@@H]1O	2272.8	Standard non polar	33892256
Nelarabine	COC1=NC(N)=NC2=C1N=CN2[C@@H]1O[C@H](CO)[C@@H](O)[C@@H]1O	2828.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Nelarabine,1TMS,isomer #1	COC1=NC(N)=NC2=C1N=CN2[C@@H]1O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]1O	2815.0	Semi standard non polar	33892256
Nelarabine,1TMS,isomer #2	COC1=NC(N)=NC2=C1N=CN2[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]1O	2822.2	Semi standard non polar	33892256
Nelarabine,1TMS,isomer #3	COC1=NC(N)=NC2=C1N=CN2[C@@H]1O[C@H](CO)[C@@H](O)[C@@H]1O[Si](C)(C)C	2817.2	Semi standard non polar	33892256
Nelarabine,1TMS,isomer #4	COC1=NC(N[Si](C)(C)C)=NC2=C1N=CN2[C@@H]1O[C@H](CO)[C@@H](O)[C@@H]1O	2890.6	Semi standard non polar	33892256
Nelarabine,2TMS,isomer #1	COC1=NC(N)=NC2=C1N=CN2[C@@H]1O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O	2757.6	Semi standard non polar	33892256
Nelarabine,2TMS,isomer #2	COC1=NC(N)=NC2=C1N=CN2[C@@H]1O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]1O[Si](C)(C)C	2768.1	Semi standard non polar	33892256
Nelarabine,2TMS,isomer #3	COC1=NC(N[Si](C)(C)C)=NC2=C1N=CN2[C@@H]1O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]1O	2813.9	Semi standard non polar	33892256
Nelarabine,2TMS,isomer #4	COC1=NC(N)=NC2=C1N=CN2[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	2767.0	Semi standard non polar	33892256
Nelarabine,2TMS,isomer #5	COC1=NC(N[Si](C)(C)C)=NC2=C1N=CN2[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]1O	2814.2	Semi standard non polar	33892256
Nelarabine,2TMS,isomer #6	COC1=NC(N[Si](C)(C)C)=NC2=C1N=CN2[C@@H]1O[C@H](CO)[C@@H](O)[C@@H]1O[Si](C)(C)C	2813.2	Semi standard non polar	33892256
Nelarabine,2TMS,isomer #7	COC1=NC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=C1N=CN2[C@@H]1O[C@H](CO)[C@@H](O)[C@@H]1O	2808.7	Semi standard non polar	33892256
Nelarabine,3TMS,isomer #1	COC1=NC(N)=NC2=C1N=CN2[C@@H]1O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	2719.1	Semi standard non polar	33892256
Nelarabine,3TMS,isomer #2	COC1=NC(N[Si](C)(C)C)=NC2=C1N=CN2[C@@H]1O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O	2785.2	Semi standard non polar	33892256
Nelarabine,3TMS,isomer #3	COC1=NC(N[Si](C)(C)C)=NC2=C1N=CN2[C@@H]1O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]1O[Si](C)(C)C	2795.9	Semi standard non polar	33892256
Nelarabine,3TMS,isomer #4	COC1=NC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=C1N=CN2[C@@H]1O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]1O	2794.0	Semi standard non polar	33892256
Nelarabine,3TMS,isomer #5	COC1=NC(N[Si](C)(C)C)=NC2=C1N=CN2[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	2786.5	Semi standard non polar	33892256
Nelarabine,3TMS,isomer #6	COC1=NC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=C1N=CN2[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]1O	2802.3	Semi standard non polar	33892256
Nelarabine,3TMS,isomer #7	COC1=NC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=C1N=CN2[C@@H]1O[C@H](CO)[C@@H](O)[C@@H]1O[Si](C)(C)C	2804.1	Semi standard non polar	33892256
Nelarabine,4TMS,isomer #1	COC1=NC(N[Si](C)(C)C)=NC2=C1N=CN2[C@@H]1O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	2815.5	Semi standard non polar	33892256
Nelarabine,4TMS,isomer #1	COC1=NC(N[Si](C)(C)C)=NC2=C1N=CN2[C@@H]1O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	2817.0	Standard non polar	33892256
Nelarabine,4TMS,isomer #1	COC1=NC(N[Si](C)(C)C)=NC2=C1N=CN2[C@@H]1O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	3780.5	Standard polar	33892256
Nelarabine,4TMS,isomer #2	COC1=NC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=C1N=CN2[C@@H]1O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O	2813.8	Semi standard non polar	33892256
Nelarabine,4TMS,isomer #2	COC1=NC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=C1N=CN2[C@@H]1O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O	2913.6	Standard non polar	33892256
Nelarabine,4TMS,isomer #2	COC1=NC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=C1N=CN2[C@@H]1O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O	3670.1	Standard polar	33892256
Nelarabine,4TMS,isomer #3	COC1=NC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=C1N=CN2[C@@H]1O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]1O[Si](C)(C)C	2819.8	Semi standard non polar	33892256
Nelarabine,4TMS,isomer #3	COC1=NC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=C1N=CN2[C@@H]1O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]1O[Si](C)(C)C	2934.9	Standard non polar	33892256
Nelarabine,4TMS,isomer #3	COC1=NC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=C1N=CN2[C@@H]1O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]1O[Si](C)(C)C	3721.3	Standard polar	33892256
Nelarabine,4TMS,isomer #4	COC1=NC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=C1N=CN2[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	2822.4	Semi standard non polar	33892256
Nelarabine,4TMS,isomer #4	COC1=NC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=C1N=CN2[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	2933.7	Standard non polar	33892256
Nelarabine,4TMS,isomer #4	COC1=NC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=C1N=CN2[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	3647.7	Standard polar	33892256
Nelarabine,5TMS,isomer #1	COC1=NC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=C1N=CN2[C@@H]1O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	2864.2	Semi standard non polar	33892256
Nelarabine,5TMS,isomer #1	COC1=NC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=C1N=CN2[C@@H]1O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	2897.3	Standard non polar	33892256
Nelarabine,5TMS,isomer #1	COC1=NC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=C1N=CN2[C@@H]1O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	3434.6	Standard polar	33892256
Nelarabine,1TBDMS,isomer #1	COC1=NC(N)=NC2=C1N=CN2[C@@H]1O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1O	3048.2	Semi standard non polar	33892256
Nelarabine,1TBDMS,isomer #2	COC1=NC(N)=NC2=C1N=CN2[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O	3051.9	Semi standard non polar	33892256
Nelarabine,1TBDMS,isomer #3	COC1=NC(N)=NC2=C1N=CN2[C@@H]1O[C@H](CO)[C@@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C	3046.3	Semi standard non polar	33892256
Nelarabine,1TBDMS,isomer #4	COC1=NC(N[Si](C)(C)C(C)(C)C)=NC2=C1N=CN2[C@@H]1O[C@H](CO)[C@@H](O)[C@@H]1O	3066.9	Semi standard non polar	33892256
Nelarabine,2TBDMS,isomer #1	COC1=NC(N)=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]1O	3201.3	Semi standard non polar	33892256
Nelarabine,2TBDMS,isomer #2	COC1=NC(N)=NC2=C1N=CN2[C@@H]1O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C	3210.8	Semi standard non polar	33892256
Nelarabine,2TBDMS,isomer #3	COC1=NC(N[Si](C)(C)C(C)(C)C)=NC2=C1N=CN2[C@@H]1O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1O	3228.2	Semi standard non polar	33892256
Nelarabine,2TBDMS,isomer #4	COC1=NC(N)=NC2=C1N=CN2[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C	3192.0	Semi standard non polar	33892256
Nelarabine,2TBDMS,isomer #5	COC1=NC(N[Si](C)(C)C(C)(C)C)=NC2=C1N=CN2[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O	3212.4	Semi standard non polar	33892256
Nelarabine,2TBDMS,isomer #6	COC1=NC(N[Si](C)(C)C(C)(C)C)=NC2=C1N=CN2[C@@H]1O[C@H](CO)[C@@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C	3206.7	Semi standard non polar	33892256
Nelarabine,2TBDMS,isomer #7	COC1=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=C1N=CN2[C@@H]1O[C@H](CO)[C@@H](O)[C@@H]1O	3213.1	Semi standard non polar	33892256
Nelarabine,3TBDMS,isomer #1	COC1=NC(N)=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]1O[Si](C)(C)C(C)(C)C	3358.6	Semi standard non polar	33892256
Nelarabine,3TBDMS,isomer #2	COC1=NC(N[Si](C)(C)C(C)(C)C)=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]1O	3394.0	Semi standard non polar	33892256
Nelarabine,3TBDMS,isomer #3	COC1=NC(N[Si](C)(C)C(C)(C)C)=NC2=C1N=CN2[C@@H]1O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C	3390.9	Semi standard non polar	33892256
Nelarabine,3TBDMS,isomer #4	COC1=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=C1N=CN2[C@@H]1O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1O	3375.0	Semi standard non polar	33892256
Nelarabine,3TBDMS,isomer #5	COC1=NC(N[Si](C)(C)C(C)(C)C)=NC2=C1N=CN2[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C	3372.3	Semi standard non polar	33892256
Nelarabine,3TBDMS,isomer #6	COC1=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=C1N=CN2[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O	3379.4	Semi standard non polar	33892256
Nelarabine,3TBDMS,isomer #7	COC1=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=C1N=CN2[C@@H]1O[C@H](CO)[C@@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C	3375.2	Semi standard non polar	33892256
Nelarabine,4TBDMS,isomer #1	COC1=NC(N[Si](C)(C)C(C)(C)C)=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]1O[Si](C)(C)C(C)(C)C	3557.8	Semi standard non polar	33892256
Nelarabine,4TBDMS,isomer #1	COC1=NC(N[Si](C)(C)C(C)(C)C)=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]1O[Si](C)(C)C(C)(C)C	3581.0	Standard non polar	33892256
Nelarabine,4TBDMS,isomer #1	COC1=NC(N[Si](C)(C)C(C)(C)C)=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]1O[Si](C)(C)C(C)(C)C	3962.6	Standard polar	33892256
Nelarabine,4TBDMS,isomer #2	COC1=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=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]1O	3540.1	Semi standard non polar	33892256
Nelarabine,4TBDMS,isomer #2	COC1=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=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]1O	3654.6	Standard non polar	33892256
Nelarabine,4TBDMS,isomer #2	COC1=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=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]1O	3860.0	Standard polar	33892256
Nelarabine,4TBDMS,isomer #3	COC1=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=C1N=CN2[C@@H]1O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C	3535.8	Semi standard non polar	33892256
Nelarabine,4TBDMS,isomer #3	COC1=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=C1N=CN2[C@@H]1O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C	3679.5	Standard non polar	33892256
Nelarabine,4TBDMS,isomer #3	COC1=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=C1N=CN2[C@@H]1O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C	3892.8	Standard polar	33892256
Nelarabine,4TBDMS,isomer #4	COC1=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=C1N=CN2[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C	3531.4	Semi standard non polar	33892256
Nelarabine,4TBDMS,isomer #4	COC1=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=C1N=CN2[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C	3678.3	Standard non polar	33892256
Nelarabine,4TBDMS,isomer #4	COC1=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=C1N=CN2[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C	3839.9	Standard polar	33892256
Nelarabine,5TBDMS,isomer #1	COC1=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=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]1O[Si](C)(C)C(C)(C)C	3725.0	Semi standard non polar	33892256
Nelarabine,5TBDMS,isomer #1	COC1=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=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]1O[Si](C)(C)C(C)(C)C	3759.3	Standard non polar	33892256
Nelarabine,5TBDMS,isomer #1	COC1=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=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]1O[Si](C)(C)C(C)(C)C	3755.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Nelarabine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ab9-9160000000-faf81feea076fd7f2c2e	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nelarabine GC-MS (3 TMS) - 70eV, Positive	splash10-0w30-4902300000-00b862d4b042b6caeb64	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nelarabine 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 - Nelarabine , positive-QTOF	splash10-014i-1910000000-d09b09e2c32a65f2ac55	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nelarabine 10V, Positive-QTOF	splash10-014i-0940000000-05786731bc8af4c9273c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nelarabine 20V, Positive-QTOF	splash10-014i-0900000000-c1582ed3900ea73a1a3a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nelarabine 40V, Positive-QTOF	splash10-0159-0900000000-862068247f35d06ca7cf	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nelarabine 10V, Negative-QTOF	splash10-01ot-0590000000-efa66ff74370c360726c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nelarabine 20V, Negative-QTOF	splash10-01q9-0910000000-87f932f5a7438fca86cc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nelarabine 40V, Negative-QTOF	splash10-0a4i-2900000000-cfa051ab5e966ccd6168	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nelarabine 10V, Positive-QTOF	splash10-014i-0900000000-7f20cf9333bbb1eb98e1	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nelarabine 20V, Positive-QTOF	splash10-014i-0900000000-49bf916fd47c2c0647da	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nelarabine 40V, Positive-QTOF	splash10-014i-1900000000-8261e4d55d25a6e7e406	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nelarabine 10V, Negative-QTOF	splash10-0002-0590000000-3e9e0887473f63d8445e	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nelarabine 20V, Negative-QTOF	splash10-03e9-0910000000-b322547ac26e69901a1e	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nelarabine 40V, Negative-QTOF	splash10-0bt9-1910000000-eb40dee5635f93bf37ea	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

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 DB01280	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01280	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01280

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2280207

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Nelarabine

METLIN ID

Not Available

PubChem Compound

3011155

PDB ID

Not Available

ChEBI ID

63612

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

Buie LW, Epstein SS, Lindley CM: Nelarabine: a novel purine antimetabolite antineoplastic agent. Clin Ther. 2007 Sep;29(9):1887-99. [PubMed:18035189 ]
DeAngelo DJ: Nelarabine for the treatment of patients with relapsed or refractory T-cell acute lymphoblastic leukemia or lymphoblastic lymphoma. Hematol Oncol Clin North Am. 2009 Oct;23(5):1121-35, vii-viii. doi: 10.1016/j.hoc.2009.07.008. [PubMed:19825456 ]
Reilly KM, Kisor DF: Profile of nelarabine: use in the treatment of T-cell acute lymphoblastic leukemia. Onco Targets Ther. 2009 Feb 18;2:219-28. [PubMed:20616909 ]
Cooper TM: Role of nelarabine in the treatment of T-cell acute lymphoblastic leukemia and T-cell lymphoblastic lymphoma. Ther Clin Risk Manag. 2007 Dec;3(6):1135-41. [PubMed:18516261 ]
Gandhi V, Keating MJ, Bate G, Kirkpatrick P: Nelarabine. Nat Rev Drug Discov. 2006 Jan;5(1):17-8. [PubMed:16485343 ]
Curbo S, Karlsson A: Nelarabine: a new purine analog in the treatment of hematologic malignancies. Rev Recent Clin Trials. 2006 Sep;1(3):185-92. [PubMed:18473971 ]
Roecker AM, Allison JC, Kisor DF: Nelarabine: efficacy in the treatment of clinical malignancies. Future Oncol. 2006 Aug;2(4):441-8. [PubMed:16922610 ]
Sanford M, Lyseng-Williamson KA: Nelarabine. Drugs. 2008;68(4):439-47. [PubMed:18318562 ]
Sigalas P, Tourvas AD, Moulakakis A, Pangalis G, Kontopidou F: Nelarabine induced complete remission in an adult with refractory T-lineage acute lymphoblastic leukemia: A case report and review of the literature. Leuk Res. 2009 Jul;33(7):e61-3. doi: 10.1016/j.leukres.2008.12.005. Epub 2009 Jan 21. [PubMed:19157550 ]

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

Buie LW, Epstein SS, Lindley CM: Nelarabine: a novel purine antimetabolite antineoplastic agent. Clin Ther. 2007 Sep;29(9):1887-99. [PubMed:18035189 ]
DeAngelo DJ: Nelarabine for the treatment of patients with relapsed or refractory T-cell acute lymphoblastic leukemia or lymphoblastic lymphoma. Hematol Oncol Clin North Am. 2009 Oct;23(5):1121-35, vii-viii. doi: 10.1016/j.hoc.2009.07.008. [PubMed:19825456 ]
Reilly KM, Kisor DF: Profile of nelarabine: use in the treatment of T-cell acute lymphoblastic leukemia. Onco Targets Ther. 2009 Feb 18;2:219-28. [PubMed:20616909 ]
Cooper TM: Role of nelarabine in the treatment of T-cell acute lymphoblastic leukemia and T-cell lymphoblastic lymphoma. Ther Clin Risk Manag. 2007 Dec;3(6):1135-41. [PubMed:18516261 ]
DeAngelo DJ, Yu D, Johnson JL, Coutre SE, Stone RM, Stopeck AT, Gockerman JP, Mitchell BS, Appelbaum FR, Larson RA: Nelarabine induces complete remissions in adults with relapsed or refractory T-lineage acute lymphoblastic leukemia or lymphoblastic lymphoma: Cancer and Leukemia Group B study 19801. Blood. 2007 Jun 15;109(12):5136-42. Epub 2007 Mar 7. [PubMed:17344466 ]

Enzyme Details

2. Adenosine deaminase

General function:: Involved in deaminase activity
Specific function:: Catalyzes the hydrolytic deamination of adenosine and 2-deoxyadenosine. Plays an important role in purine metabolism and in adenosine homeostasis. Modulates signaling by extracellular adenosine, and so contributes indirectly to cellular signaling events. Acts as a positive regulator of T-cell coactivation, by binding DPP4. Its interaction with DPP4 regulates lymphocyte-epithelial cell adhesion.
Gene Name:: ADA
Uniprot ID:: P00813
Molecular weight:: 40764.13

References

Buie LW, Epstein SS, Lindley CM: Nelarabine: a novel purine antimetabolite antineoplastic agent. Clin Ther. 2007 Sep;29(9):1887-99. [PubMed:18035189 ]
DeAngelo DJ: Nelarabine for the treatment of patients with relapsed or refractory T-cell acute lymphoblastic leukemia or lymphoblastic lymphoma. Hematol Oncol Clin North Am. 2009 Oct;23(5):1121-35, vii-viii. doi: 10.1016/j.hoc.2009.07.008. [PubMed:19825456 ]
Reilly KM, Kisor DF: Profile of nelarabine: use in the treatment of T-cell acute lymphoblastic leukemia. Onco Targets Ther. 2009 Feb 18;2:219-28. [PubMed:20616909 ]
Cooper TM: Role of nelarabine in the treatment of T-cell acute lymphoblastic leukemia and T-cell lymphoblastic lymphoma. Ther Clin Risk Manag. 2007 Dec;3(6):1135-41. [PubMed:18516261 ]
Cohen MH, Johnson JR, Justice R, Pazdur R: FDA drug approval summary: nelarabine (Arranon) for the treatment of T-cell lymphoblastic leukemia/lymphoma. Oncologist. 2008 Jun;13(6):709-14. doi: 10.1634/theoncologist.2006-0017. [PubMed:18586926 ]
Gandhi V, Keating MJ, Bate G, Kirkpatrick P: Nelarabine. Nat Rev Drug Discov. 2006 Jan;5(1):17-8. [PubMed:16485343 ]

Enzyme Details

3. Deoxyguanosine kinase, mitochondrial

General function:: Involved in ATP binding
Specific function:: Required for the phosphorylation of several deoxyribonucleosides and certain nucleoside analogs widely employed as antiviral and chemotherapeutic agents.
Gene Name:: DGUOK
Uniprot ID:: Q16854
Molecular weight:: 32055.53

References

Buie LW, Epstein SS, Lindley CM: Nelarabine: a novel purine antimetabolite antineoplastic agent. Clin Ther. 2007 Sep;29(9):1887-99. [PubMed:18035189 ]
DeAngelo DJ: Nelarabine for the treatment of patients with relapsed or refractory T-cell acute lymphoblastic leukemia or lymphoblastic lymphoma. Hematol Oncol Clin North Am. 2009 Oct;23(5):1121-35, vii-viii. doi: 10.1016/j.hoc.2009.07.008. [PubMed:19825456 ]
Reilly KM, Kisor DF: Profile of nelarabine: use in the treatment of T-cell acute lymphoblastic leukemia. Onco Targets Ther. 2009 Feb 18;2:219-28. [PubMed:20616909 ]
Cooper TM: Role of nelarabine in the treatment of T-cell acute lymphoblastic leukemia and T-cell lymphoblastic lymphoma. Ther Clin Risk Manag. 2007 Dec;3(6):1135-41. [PubMed:18516261 ]
DeAngelo DJ, Yu D, Johnson JL, Coutre SE, Stone RM, Stopeck AT, Gockerman JP, Mitchell BS, Appelbaum FR, Larson RA: Nelarabine induces complete remissions in adults with relapsed or refractory T-lineage acute lymphoblastic leukemia or lymphoblastic lymphoma: Cancer and Leukemia Group B study 19801. Blood. 2007 Jun 15;109(12):5136-42. Epub 2007 Mar 7. [PubMed:17344466 ]

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

Ono K, Ohashi A, Yamamoto A, Matsukage A, Takahasi T, Saneyoshi M, Ueda T: Inhibitory effects of 9-beta-D-arabinofuranosylguanine 5'-triphosphate and 9-beta-D-arabinofuranosyladenine 5'-triphosphate on DNA polymerases from murine cells and oncornavirus. Cancer Res. 1979 Nov;39(11):4673-80. [PubMed:91427 ]
Buie LW, Epstein SS, Lindley CM: Nelarabine: a novel purine antimetabolite antineoplastic agent. Clin Ther. 2007 Sep;29(9):1887-99. [PubMed:18035189 ]
Curbo S, Karlsson A: Nelarabine: a new purine analog in the treatment of hematologic malignancies. Rev Recent Clin Trials. 2006 Sep;1(3):185-92. [PubMed:18473971 ]
Rodriguez CO Jr, Stellrecht CM, Gandhi V: Mechanisms for T-cell selective cytotoxicity of arabinosylguanine. Blood. 2003 Sep 1;102(5):1842-8. Epub 2003 May 15. [PubMed:12750168 ]

Showing metabocard for Nelarabine (HMDB0015401)

MOL for HMDB0015401 (Nelarabine)

3D MOL for HMDB0015401 (Nelarabine)

3D SDF for HMDB0015401 (Nelarabine)

3D-SDF for HMDB0015401 (Nelarabine)

PDB for HMDB0015401 (Nelarabine)

3D PDB for HMDB0015401 (Nelarabine)

SMILES for HMDB0015401 (Nelarabine)

INCHI for HMDB0015401 (Nelarabine)

Structure for HMDB0015401 (Nelarabine)

3D Structure for HMDB0015401 (Nelarabine)

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

References