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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2022-03-07 02:51:42 UTC

HMDB ID

HMDB0014692

Secondary Accession Numbers

HMDB14692

Metabolite Identification

Common Name

Pentostatin

Description

Pentostatin is only found in individuals that have used or taken this drug. It is a potent inhibitor of adenosine deaminase. The drug is effective in the treatment of many lymphoproliferative malignancies, particularly hairy-cell leukemia. It is also synergistic with some other antineoplastic agents and has immunosuppressive activity. [PubChem]Pentostatin is a potent transition state inhibitor of adenosine deaminase (ADA), the greatest activity of which is found in cells of the lymphoid system. T-cells have higher ADA activity than B-cells, and T-cell malignancies have higher activity than B-cell malignancies. The cytotoxicity that results from prevention of catabolism of adenosine or deoxyadenosine is thought to be due to elevated intracellular levels of dATP, which can block DNA synthesis through inhibition of ribonucleotide reductase. Intracellular activation results in incorporation into DNA as a false purine base. An additional cytotoxic effect is related to its incorporation into RNA. Cytotoxicity is cell cycle phase-specific (S-phase).

Structure

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

HMDB0014692
     RDKit          3D
Pentostatin
 35 37  0  0  0  0  0  0  0  0999 V2000
    5.3261    0.8193   -0.3086 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0859    0.8436   -0.9577 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9986    0.6598    0.0994 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7492    0.6729   -0.4647 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0152   -0.3172    0.1314 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1881   -0.6620   -0.5351 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3895   -1.4920   -1.5692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7027   -1.5285   -1.8906 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3660   -0.6958   -1.0361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4060   -0.1696   -0.2044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6527    0.7555    0.8489 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7478    0.9992    1.5164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9818    0.3336    1.2932 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4691   -0.5521    0.2938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8048   -0.4426   -1.0384 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1069    0.8242   -1.5884 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0241   -1.4728    0.1625 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2240   -0.6931    0.7195 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0083   -0.5798    2.0988 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2548    0.6070    0.6416 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0889    0.0063   -1.6766 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9864    1.8151   -1.4785 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0649    1.4849    0.8211 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8598   -0.0538    1.2133 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3502   -2.0644   -2.0965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7303    1.7516    2.2905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6965    0.5486    2.0427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5530   -0.3662    0.1477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3600   -1.5943    0.6559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2871   -1.1756   -1.7181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4562    1.4584   -1.1921 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7201   -2.2728    0.8360 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2546   -1.8087   -0.8686 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1735   -1.1568    0.4638 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7142    0.3467    2.3471 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
  5 17  1  0
 17 18  1  0
 18 19  1  0
 18  3  1  0
 10  6  1  0
 15  9  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  3 23  1  1
  5 24  1  1
  7 25  1  0
 12 26  1  0
 13 27  1  0
 14 28  1  0
 14 29  1  0
 15 30  1  6
 16 31  1  0
 17 32  1  0
 17 33  1  0
 18 34  1  1
 19 35  1  0
M  END

 
  Mrv0541 02231214462D          
 
 19 21  0  0  1  0            999 V2000
   14.7813   -9.8538    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.5328  -10.6405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1188   -9.3570    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4563   -9.8538    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.7047  -10.6405    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.2079  -11.3030    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6696   -9.5640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5040   -8.7773    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5680   -9.6054    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.1884  -10.9914    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.1999  -10.0721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8195   -9.5856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7087   -9.7702    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.8780  -11.4681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0258  -10.5090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6882  -11.2526    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.5940   -8.8331    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.7324   -8.8316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1854   -9.0806    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  2  5  1  0  0  0  0
  5  6  1  6  0  0  0
  4  7  1  1  0  0  0
  7  8  1  0  0  0  0
  1  9  1  1  0  0  0
 12 13  1  0  0  0  0
 10 14  2  0  0  0  0
 13 15  1  0  0  0  0
 11 12  2  0  0  0  0
 14 16  1  0  0  0  0
 10 11  1  0  0  0  0
 15 16  1  0  0  0  0
 12 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18  9  1  0  0  0  0
 11  9  1  0  0  0  0
 13 19  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0014692

> <DATABASE_NAME>
hmdb

> <SMILES>
OC[C@H]1O[C@H](C[C@@H]1O)N1C=NC2=C1N=CNC[C@H]2O

> <INCHI_IDENTIFIER>
InChI=1S/C11H16N4O4/c16-3-8-6(17)1-9(19-8)15-5-14-10-7(18)2-12-4-13-11(10)15/h4-9,16-18H,1-3H2,(H,12,13)/t6-,7+,8+,9+/m0/s1

> <INCHI_KEY>
FPVKHBSQESCIEP-JQCXWYLXSA-N

> <FORMULA>
C11H16N4O4

> <MOLECULAR_WEIGHT>
268.2691

> <EXACT_MASS>
268.11715502

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
26.44050089223065

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(8R)-3-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H,6H,7H,8H-imidazo[4,5-d][1,3]diazepin-8-ol

> <ALOGPS_LOGP>
-2.03

> <JCHEM_LOGP>
-2.0163910279999997

> <ALOGPS_LOGS>
-1.40

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
13.947628022011795

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.062051268906174

> <JCHEM_PKA_STRONGEST_BASIC>
8.32598891305454

> <JCHEM_POLAR_SURFACE_AREA>
112.13

> <JCHEM_REFRACTIVITY>
64.9814

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.07e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
pentostatin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014692
     RDKit          3D
Pentostatin
 35 37  0  0  0  0  0  0  0  0999 V2000
    5.3261    0.8193   -0.3086 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0859    0.8436   -0.9577 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9986    0.6598    0.0994 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7492    0.6729   -0.4647 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0152   -0.3172    0.1314 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1881   -0.6620   -0.5351 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3895   -1.4920   -1.5692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7027   -1.5285   -1.8906 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3660   -0.6958   -1.0361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4060   -0.1696   -0.2044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6527    0.7555    0.8489 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7478    0.9992    1.5164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9818    0.3336    1.2932 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4691   -0.5521    0.2938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8048   -0.4426   -1.0384 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1069    0.8242   -1.5884 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0241   -1.4728    0.1625 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2240   -0.6931    0.7195 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0083   -0.5798    2.0988 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2548    0.6070    0.6416 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0889    0.0063   -1.6766 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9864    1.8151   -1.4785 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0649    1.4849    0.8211 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8598   -0.0538    1.2133 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3502   -2.0644   -2.0965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7303    1.7516    2.2905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6965    0.5486    2.0427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5530   -0.3662    0.1477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3600   -1.5943    0.6559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2871   -1.1756   -1.7181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4562    1.4584   -1.1921 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7201   -2.2728    0.8360 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2546   -1.8087   -0.8686 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1735   -1.1568    0.4638 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7142    0.3467    2.3471 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
  5 17  1  0
 17 18  1  0
 18 19  1  0
 18  3  1  0
 10  6  1  0
 15  9  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  3 23  1  1
  5 24  1  1
  7 25  1  0
 12 26  1  0
 13 27  1  0
 14 28  1  0
 14 29  1  0
 15 30  1  6
 16 31  1  0
 17 32  1  0
 17 33  1  0
 18 34  1  1
 19 35  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      27.592 -18.394   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      27.128 -19.862   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      26.355 -17.466   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      25.118 -18.394   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      25.582 -19.862   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      24.655 -21.099   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      23.650 -17.853   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      23.341 -16.384   0.000  0.00  0.00           O+0
HETATM    9  N   UNK     0      29.060 -17.930   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0      30.218 -20.517   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0      30.240 -18.801   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      31.396 -17.893   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      33.056 -18.238   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      31.506 -21.407   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      33.648 -19.617   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0      33.018 -21.005   0.000  0.00  0.00           N+0
HETATM   17  N   UNK     0      30.975 -16.488   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0      29.367 -16.486   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      33.946 -16.950   0.000  0.00  0.00           O+0
CONECT    1    2    3    9                                                  
CONECT    2    1    5                                                       
CONECT    3    1    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    2    6                                                  
CONECT    6    5                                                            
CONECT    7    4    8                                                       
CONECT    8    7                                                            
CONECT    9    1   18   11                                                  
CONECT   10   14   11                                                       
CONECT   11   12   10    9                                                  
CONECT   12   13   11   17                                                  
CONECT   13   12   15   19                                                  
CONECT   14   10   16                                                       
CONECT   15   13   16                                                       
CONECT   16   14   15                                                       
CONECT   17   12   18                                                       
CONECT   18   17    9                                                       
CONECT   19   13                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

COMPND    HMDB0014692
HETATM    1  O1  UNL     1       5.326   0.819  -0.309  1.00  0.00           O  
HETATM    2  C1  UNL     1       4.086   0.844  -0.958  1.00  0.00           C  
HETATM    3  C2  UNL     1       2.999   0.660   0.099  1.00  0.00           C  
HETATM    4  O2  UNL     1       1.749   0.673  -0.465  1.00  0.00           O  
HETATM    5  C3  UNL     1       1.015  -0.317   0.131  1.00  0.00           C  
HETATM    6  N1  UNL     1      -0.188  -0.662  -0.535  1.00  0.00           N  
HETATM    7  C4  UNL     1      -0.389  -1.492  -1.569  1.00  0.00           C  
HETATM    8  N2  UNL     1      -1.703  -1.528  -1.891  1.00  0.00           N  
HETATM    9  C5  UNL     1      -2.366  -0.696  -1.036  1.00  0.00           C  
HETATM   10  C6  UNL     1      -1.406  -0.170  -0.204  1.00  0.00           C  
HETATM   11  N3  UNL     1      -1.653   0.756   0.849  1.00  0.00           N  
HETATM   12  C7  UNL     1      -2.748   0.999   1.516  1.00  0.00           C  
HETATM   13  N4  UNL     1      -3.982   0.334   1.293  1.00  0.00           N  
HETATM   14  C8  UNL     1      -4.469  -0.552   0.294  1.00  0.00           C  
HETATM   15  C9  UNL     1      -3.805  -0.443  -1.038  1.00  0.00           C  
HETATM   16  O3  UNL     1      -4.107   0.824  -1.588  1.00  0.00           O  
HETATM   17  C10 UNL     1       2.024  -1.473   0.163  1.00  0.00           C  
HETATM   18  C11 UNL     1       3.224  -0.693   0.719  1.00  0.00           C  
HETATM   19  O4  UNL     1       3.008  -0.580   2.099  1.00  0.00           O  
HETATM   20  H1  UNL     1       5.255   0.607   0.642  1.00  0.00           H  
HETATM   21  H2  UNL     1       4.089   0.006  -1.677  1.00  0.00           H  
HETATM   22  H3  UNL     1       3.986   1.815  -1.478  1.00  0.00           H  
HETATM   23  H4  UNL     1       3.065   1.485   0.821  1.00  0.00           H  
HETATM   24  H5  UNL     1       0.860  -0.054   1.213  1.00  0.00           H  
HETATM   25  H6  UNL     1       0.350  -2.064  -2.096  1.00  0.00           H  
HETATM   26  H7  UNL     1      -2.730   1.752   2.290  1.00  0.00           H  
HETATM   27  H8  UNL     1      -4.697   0.549   2.043  1.00  0.00           H  
HETATM   28  H9  UNL     1      -5.553  -0.366   0.148  1.00  0.00           H  
HETATM   29  H10 UNL     1      -4.360  -1.594   0.656  1.00  0.00           H  
HETATM   30  H11 UNL     1      -4.287  -1.176  -1.718  1.00  0.00           H  
HETATM   31  H12 UNL     1      -3.456   1.458  -1.192  1.00  0.00           H  
HETATM   32  H13 UNL     1       1.720  -2.273   0.836  1.00  0.00           H  
HETATM   33  H14 UNL     1       2.255  -1.809  -0.869  1.00  0.00           H  
HETATM   34  H15 UNL     1       4.173  -1.157   0.464  1.00  0.00           H  
HETATM   35  H16 UNL     1       2.714   0.347   2.347  1.00  0.00           H  
CONECT    1    2   20
CONECT    2    3   21   22
CONECT    3    4   18   23
CONECT    4    5
CONECT    5    6   17   24
CONECT    6    7   10
CONECT    7    8    8   25
CONECT    8    9
CONECT    9   10   10   15
CONECT   10   11
CONECT   11   12   12
CONECT   12   13   26
CONECT   13   14   27
CONECT   14   15   28   29
CONECT   15   16   30
CONECT   16   31
CONECT   17   18   32   33
CONECT   18   19   34
CONECT   19   35
END

HMDB0014692
     RDKit          3D
Pentostatin
 35 37  0  0  0  0  0  0  0  0999 V2000
    5.3261    0.8193   -0.3086 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0859    0.8436   -0.9577 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9986    0.6598    0.0994 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7492    0.6729   -0.4647 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0152   -0.3172    0.1314 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1881   -0.6620   -0.5351 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3895   -1.4920   -1.5692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7027   -1.5285   -1.8906 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3660   -0.6958   -1.0361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4060   -0.1696   -0.2044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6527    0.7555    0.8489 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7478    0.9992    1.5164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9818    0.3336    1.2932 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4691   -0.5521    0.2938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8048   -0.4426   -1.0384 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1069    0.8242   -1.5884 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0241   -1.4728    0.1625 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2240   -0.6931    0.7195 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0083   -0.5798    2.0988 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2548    0.6070    0.6416 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0889    0.0063   -1.6766 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9864    1.8151   -1.4785 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0649    1.4849    0.8211 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8598   -0.0538    1.2133 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3502   -2.0644   -2.0965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7303    1.7516    2.2905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6965    0.5486    2.0427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5530   -0.3662    0.1477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3600   -1.5943    0.6559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2871   -1.1756   -1.7181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4562    1.4584   -1.1921 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7201   -2.2728    0.8360 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2546   -1.8087   -0.8686 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1735   -1.1568    0.4638 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7142    0.3467    2.3471 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
  5 17  1  0
 17 18  1  0
 18 19  1  0
 18  3  1  0
 10  6  1  0
 15  9  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  3 23  1  1
  5 24  1  1
  7 25  1  0
 12 26  1  0
 13 27  1  0
 14 28  1  0
 14 29  1  0
 15 30  1  6
 16 31  1  0
 17 32  1  0
 17 33  1  0
 18 34  1  1
 19 35  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Nipent	Kegg
2'-DCF	HMDB
2'-Deoxycoformycin	HMDB
2'-Dexoycoformycin	HMDB
Deoxycoformycin	HMDB
CO-Vidarabine	HMDB
Lederle brand OF pentostatin	HMDB
Warner-lambert brand OF pentostatin	HMDB
Prasfarma brand OF pentostatin	HMDB
2' Deoxycoformycin	HMDB
Co vidarabine	HMDB
Supergen brand OF pentostatin	HMDB
Wyeth brand OF pentostatin	HMDB
Pentostatin	KEGG

Chemical Formula

C₁₁H₁₆N₄O₄

Average Molecular Weight

268.2691

Monoisotopic Molecular Weight

268.11715502

IUPAC Name

(8R)-3-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H,6H,7H,8H-imidazo[4,5-d][1,3]diazepin-8-ol

Traditional Name

pentostatin

CAS Registry Number

53910-25-1

SMILES

OC[C@H]1O[C@H](C[C@@H]1O)N1C=NC2=C1N=CNC[C@H]2O

InChI Identifier

InChI=1S/C11H16N4O4/c16-3-8-6(17)1-9(19-8)15-5-14-10-7(18)2-12-4-13-11(10)15/h4-9,16-18H,1-3H2,(H,12,13)/t6-,7+,8+,9+/m0/s1

InChI Key

FPVKHBSQESCIEP-JQCXWYLXSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as imidazodiazepines. These are organic compounds containing an imidazole ring fused to a diazepine ring. Imidazole is 5-membered ring consisting of three carbon atoms, and two nitrogen centers at the 1- and 3-positions. Diazepine is a 7-membered ring consisting of five carbon and two nitrogen atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Imidazodiazepines

Sub Class

Not Available

Direct Parent

Imidazodiazepines

Alternative Parents

Substituents

Imidazo-meta-diazepine
Imidazodiazepine
Meta-diazepine
N-substituted imidazole
Azole
Imidazole
Heteroaromatic compound
Tetrahydrofuran
Secondary alcohol
Amidine
Formamidine
Carboxylic acid amidine
Oxacycle
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Hydrocarbon derivative
Organopnictogen compound
Organonitrogen compound
Organooxygen compound
Primary alcohol
Alcohol
Organic nitrogen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

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: HMDB0014692)
Extracellular (HMDB: HMDB0014692)

Source

Exogenous

Exogenous (HMDB: HMDB0014692)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	220 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	10.7 g/L	Not Available
LogP	-1.1	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	10.7 g/L	ALOGPS
logP	-2	ALOGPS
logP	-2	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	13.06	ChemAxon
pKa (Strongest Basic)	8.33	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	112.13 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	64.98 m³·mol⁻¹	ChemAxon
Polarizability	26.44 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]+	158.383	31661259
DarkChem	[M-H]-	157.652	31661259
DeepCCS	[M+H]+	154.28	30932474
DeepCCS	[M-H]-	151.885	30932474
DeepCCS	[M-2H]-	185.767	30932474
DeepCCS	[M+Na]+	160.624	30932474
AllCCS	[M+H]+	161.8	32859911
AllCCS	[M+H-H2O]+	158.2	32859911
AllCCS	[M+NH4]+	165.1	32859911
AllCCS	[M+Na]+	166.1	32859911
AllCCS	[M-H]-	161.5	32859911
AllCCS	[M+Na-2H]-	161.0	32859911
AllCCS	[M+HCOO]-	160.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Pentostatin	OC[C@H]1O[C@H](C[C@@H]1O)N1C=NC2=C1N=CNC[C@H]2O	3916.2	Standard polar	33892256
Pentostatin	OC[C@H]1O[C@H](C[C@@H]1O)N1C=NC2=C1N=CNC[C@H]2O	2521.7	Standard non polar	33892256
Pentostatin	OC[C@H]1O[C@H](C[C@@H]1O)N1C=NC2=C1N=CNC[C@H]2O	2862.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Pentostatin,1TMS,isomer #1	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2N=CNC[C@H]3O)C[C@@H]1O	2631.0	Semi standard non polar	33892256
Pentostatin,1TMS,isomer #2	C[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C2N=CNC[C@H]3O)O[C@@H]1CO	2622.1	Semi standard non polar	33892256
Pentostatin,1TMS,isomer #3	C[Si](C)(C)O[C@@H]1CNC=NC2=C1N=CN2[C@H]1C[C@H](O)[C@@H](CO)O1	2559.7	Semi standard non polar	33892256
Pentostatin,1TMS,isomer #4	C[Si](C)(C)N1C=NC2=C(N=CN2[C@H]2C[C@H](O)[C@@H](CO)O2)[C@H](O)C1	2645.9	Semi standard non polar	33892256
Pentostatin,2TMS,isomer #1	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2N=CNC[C@H]3O[Si](C)(C)C)C[C@@H]1O	2538.5	Semi standard non polar	33892256
Pentostatin,2TMS,isomer #2	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2N=CNC[C@H]3O)C[C@@H]1O[Si](C)(C)C	2549.7	Semi standard non polar	33892256
Pentostatin,2TMS,isomer #3	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2N=CN([Si](C)(C)C)C[C@H]3O)C[C@@H]1O	2618.7	Semi standard non polar	33892256
Pentostatin,2TMS,isomer #4	C[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C2N=CNC[C@H]3O[Si](C)(C)C)O[C@@H]1CO	2536.1	Semi standard non polar	33892256
Pentostatin,2TMS,isomer #5	C[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C2N=CN([Si](C)(C)C)C[C@H]3O)O[C@@H]1CO	2601.8	Semi standard non polar	33892256
Pentostatin,2TMS,isomer #6	C[Si](C)(C)O[C@@H]1CN([Si](C)(C)C)C=NC2=C1N=CN2[C@H]1C[C@H](O)[C@@H](CO)O1	2603.7	Semi standard non polar	33892256
Pentostatin,3TMS,isomer #1	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2N=CNC[C@H]3O[Si](C)(C)C)C[C@@H]1O[Si](C)(C)C	2514.4	Semi standard non polar	33892256
Pentostatin,3TMS,isomer #2	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2N=CN([Si](C)(C)C)C[C@H]3O[Si](C)(C)C)C[C@@H]1O	2585.9	Semi standard non polar	33892256
Pentostatin,3TMS,isomer #3	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2N=CN([Si](C)(C)C)C[C@H]3O)C[C@@H]1O[Si](C)(C)C	2573.9	Semi standard non polar	33892256
Pentostatin,3TMS,isomer #4	C[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C2N=CN([Si](C)(C)C)C[C@H]3O[Si](C)(C)C)O[C@@H]1CO	2574.4	Semi standard non polar	33892256
Pentostatin,4TMS,isomer #1	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2N=CN([Si](C)(C)C)C[C@H]3O[Si](C)(C)C)C[C@@H]1O[Si](C)(C)C	2572.6	Semi standard non polar	33892256
Pentostatin,4TMS,isomer #1	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2N=CN([Si](C)(C)C)C[C@H]3O[Si](C)(C)C)C[C@@H]1O[Si](C)(C)C	2705.2	Standard non polar	33892256
Pentostatin,4TMS,isomer #1	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2N=CN([Si](C)(C)C)C[C@H]3O[Si](C)(C)C)C[C@@H]1O[Si](C)(C)C	4353.1	Standard polar	33892256
Pentostatin,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2N=CNC[C@H]3O)C[C@@H]1O	2861.4	Semi standard non polar	33892256
Pentostatin,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C2N=CNC[C@H]3O)O[C@@H]1CO	2845.4	Semi standard non polar	33892256
Pentostatin,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@@H]1CNC=NC2=C1N=CN2[C@H]1C[C@H](O)[C@@H](CO)O1	2784.5	Semi standard non polar	33892256
Pentostatin,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N1C=NC2=C(N=CN2[C@H]2C[C@H](O)[C@@H](CO)O2)[C@H](O)C1	2856.8	Semi standard non polar	33892256
Pentostatin,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2N=CNC[C@H]3O[Si](C)(C)C(C)(C)C)C[C@@H]1O	2964.5	Semi standard non polar	33892256
Pentostatin,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2N=CNC[C@H]3O)C[C@@H]1O[Si](C)(C)C(C)(C)C	3009.9	Semi standard non polar	33892256
Pentostatin,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2N=CN([Si](C)(C)C(C)(C)C)C[C@H]3O)C[C@@H]1O	3040.6	Semi standard non polar	33892256
Pentostatin,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C2N=CNC[C@H]3O[Si](C)(C)C(C)(C)C)O[C@@H]1CO	2950.8	Semi standard non polar	33892256
Pentostatin,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C2N=CN([Si](C)(C)C(C)(C)C)C[C@H]3O)O[C@@H]1CO	3044.3	Semi standard non polar	33892256
Pentostatin,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)O[C@@H]1CN([Si](C)(C)C(C)(C)C)C=NC2=C1N=CN2[C@H]1C[C@H](O)[C@@H](CO)O1	3016.4	Semi standard non polar	33892256
Pentostatin,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2N=CNC[C@H]3O[Si](C)(C)C(C)(C)C)C[C@@H]1O[Si](C)(C)C(C)(C)C	3129.6	Semi standard non polar	33892256
Pentostatin,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2N=CN([Si](C)(C)C(C)(C)C)C[C@H]3O[Si](C)(C)C(C)(C)C)C[C@@H]1O	3219.2	Semi standard non polar	33892256
Pentostatin,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2N=CN([Si](C)(C)C(C)(C)C)C[C@H]3O)C[C@@H]1O[Si](C)(C)C(C)(C)C	3228.9	Semi standard non polar	33892256
Pentostatin,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C2N=CN([Si](C)(C)C(C)(C)C)C[C@H]3O[Si](C)(C)C(C)(C)C)O[C@@H]1CO	3225.5	Semi standard non polar	33892256
Pentostatin,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2N=CN([Si](C)(C)C(C)(C)C)C[C@H]3O[Si](C)(C)C(C)(C)C)C[C@@H]1O[Si](C)(C)C(C)(C)C	3410.2	Semi standard non polar	33892256
Pentostatin,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2N=CN([Si](C)(C)C(C)(C)C)C[C@H]3O[Si](C)(C)C(C)(C)C)C[C@@H]1O[Si](C)(C)C(C)(C)C	3540.0	Standard non polar	33892256
Pentostatin,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2N=CN([Si](C)(C)C(C)(C)C)C[C@H]3O[Si](C)(C)C(C)(C)C)C[C@@H]1O[Si](C)(C)C(C)(C)C	4476.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Pentostatin GC-MS (Non-derivatized) - 70eV, Positive	splash10-000f-9280000000-53989a5cd0535c5bb1c0	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pentostatin GC-MS (3 TMS) - 70eV, Positive	splash10-0g4i-5556900000-faa1467da14d5869f1a4	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pentostatin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pentostatin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pentostatin 10V, Positive-QTOF	splash10-0udr-0920000000-59e330d7bf2bc1680990	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pentostatin 20V, Positive-QTOF	splash10-0udr-0900000000-e3af78d60d01def1ac1a	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pentostatin 40V, Positive-QTOF	splash10-0f79-1900000000-d626d4471ad700c9f0d6	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pentostatin 10V, Negative-QTOF	splash10-014i-0390000000-b18e6406ad078d5394a4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pentostatin 20V, Negative-QTOF	splash10-0udi-0910000000-bc5d8c218c955e8890bd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pentostatin 40V, Negative-QTOF	splash10-05ai-9400000000-3516f2a449bec4f6eab1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pentostatin 10V, Positive-QTOF	splash10-0udi-0900000000-72c3636a284833d70d68	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pentostatin 20V, Positive-QTOF	splash10-000i-0900000000-0ed9eb4f7ab63001c261	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pentostatin 40V, Positive-QTOF	splash10-000i-0900000000-37329b69923f607d6e79	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pentostatin 10V, Negative-QTOF	splash10-0udi-0920000000-91b2100cdc647d86ee1c	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pentostatin 20V, Negative-QTOF	splash10-0udi-0900000000-5db12e941598533606e0	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pentostatin 40V, Negative-QTOF	splash10-001i-0900000000-38150a6439ac940dede9	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

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

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00552	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00552	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

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

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00552

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

388759

KEGG Compound ID

C02267

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Pentostatin

METLIN ID

Not Available

PubChem Compound

439693

PDB ID

DCF

ChEBI ID

Not Available

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

Mercieca J, Matutes E, Moskovic E, MacLennan K, Matthey F, Costello C, Behrens J, Basu S, Roath S, Fairhead S, et al.: Massive abdominal lymphadenopathy in hairy cell leukaemia: a report of 12 cases. Br J Haematol. 1992 Nov;82(3):547-54. [PubMed:1283078 ]
Schwartz CL, Minniti CP, Harwood P, Na S, Banquerigo ML, Strauss LC, Kurtzberg J, Smith SD, Civin CI: Elimination of clonogenic malignant human T cells using monoclonal antibodies in combination with 2'-deoxycoformycin. J Clin Oncol. 1987 Dec;5(12):1900-11. [PubMed:3500279 ]
Thaler J, Denz H, Dietze O, Gastl G, Ho AD, Gattringer C, Greil R, Lechleitner M, Huber C, Huber H: Immunohistological assessment of bone marrow biopsies from patients with hairy cell leukemia: changes following treatment with alpha-2-interferon and deoxycoformycin. Leuk Res. 1989;13(5):377-83. [PubMed:2787447 ]
Ruers TJ, Buurman WA, van der Linden CJ: 2'Deoxycoformycin and deoxyadenosine affect IL 2 production and IL 2 receptor expression of human T cells. J Immunol. 1987 Jan 1;138(1):116-22. [PubMed:3097141 ]
Lembersky BC, Golomb HM: Hairy cell leukemia: clinical features and therapeutic advances. Cancer Metastasis Rev. 1987;6(3):283-300. [PubMed:2446791 ]
Sainati L, Matutes E, Mulligan S, de Oliveira MP, Rani S, Lampert IA, Catovsky D: A variant form of hairy cell leukemia resistant to alpha-interferon: clinical and phenotypic characteristics of 17 patients. Blood. 1990 Jul 1;76(1):157-62. [PubMed:2364167 ]
Okamura K, Ikeda T, Shimakura Y, Yoshiba F, Kishi K, Ando K, Hotta T: [Allogeneic bone marrow transplantation for chemotherapy-resistant T-prolymphocytic leukemia]. Rinsho Ketsueki. 2005 Jul;46(7):527-31. [PubMed:16440747 ]
Mughal TI, Goldman JM: Chronic leukaemias: can they be cured? Part II: Chronic lymphocytic leukaemia. Br J Clin Pract. 1989 Oct;43(10):353-6. [PubMed:2698240 ]
O'Dwyer PJ, Cheson BD, Leyland-Jones B, King SA, Hoth DF: Deoxycoformycin: an active new drug for indolent lymphomas and hairy cell leukemia. Oncology (Williston Park). 1988 Jun;2(6):17-23, 26-7. [PubMed:3079330 ]
Bethlenfalvay NC, Lima JE, Banks RE: 2'-Deoxyadenosine metabolism in human and opossum Didelphis virginiana erythrocytes in vitro. Comp Biochem Physiol B. 1993 Nov;106(3):641-5. [PubMed:8281758 ]
Dillman RO, Yu AL, Qiao CN: Repeated pentostatin (2'deoxycoformycin)-induced remissions in a patient with advanced chronic lymphocytic leukemia. West J Med. 1988 Mar;148(3):334-7. [PubMed:3259051 ]
Catovsky D, Matutes E, Talavera JG, O'Connor NT, Johnson SA, Emmett E, Corbett L, Swansbury J: Long term results with 2'deoxycoformycin in hairy cell leukemia. Leuk Lymphoma. 1994;14 Suppl 1:109-13. [PubMed:7820041 ]
Thaler J, Dietze O, Faber V, Greil R, Gastl G, Denz H, Ho AD, Huber H: Monoclonal antibody B-ly7: a sensitive marker for detection of minimal residual disease in hairy cell leukemia. Leukemia. 1990 Mar;4(3):170-6. [PubMed:2314116 ]
Ho AD, Thaler J, Willemze R, Lauria F, Derossi G, Kuse R, Stryckmans P, Blanc CM, Cataldo F, McVie G, et al.: Pentostatin (2'deoxycoformycin) for the treatment of lymphoid neoplasms. Bone Marrow Transplant. 1989 Jan;4 Suppl 1:60-2. [PubMed:2653520 ]
Romo A, Lorente F, Salazar V: Action of 2'-deoxycoformycin on mitogen-induced lymphoproliferation in the neonatal period. Allergol Immunopathol (Madr). 1988 Jul-Aug;16(4):243-7. [PubMed:3265855 ]
Roth E Jr, Ogasawara N, Schulman S: The deamination of adenosine and adenosine monophosphate in Plasmodium falciparum-infected human erythrocytes: in vitro use of 2'deoxycoformycin and AMP deaminase-deficient red cells. Blood. 1989 Aug 15;74(3):1121-5. [PubMed:2665862 ]
Mante S, Minneman KP: Is adenosine involved in inhibition of forskolin-stimulated cyclic AMP accumulation by caffeine in rat brain? Mol Pharmacol. 1990 Nov;38(5):652-9. [PubMed:2172772 ]
Fabian I, Williams Z: The effect of deoxycoformycin on bone marrow cells treated with adenosine and deoxyadenosine and hemopoietic growth factors. Hum Immunol. 1988 Feb;21(2):81-7. [PubMed:3259223 ]
Montgomery RB, Kurtzberg J, Rhinehardt-Clark A, Haleen A, Ramakrishnan S, Olsen GA, Peters WP, Smith CA, Haynes BF, Houston LL, et al.: Elimination of malignant clonogenic T cells from human bone marrow using chemoimmunoseparation with 2'-deoxycoformycin, deoxyadenosine and an immunotoxin. Bone Marrow Transplant. 1990 Jun;5(6):395-402. [PubMed:2369680 ]
BC Cancer Agency [Link]

Enzymes

Enzyme Details

1. 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

Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Jackson RC, Leopold WR, Ross DA: The biochemical pharmacology of (2'-R)-chloropentostatin, a novel inhibitor of adenosine deaminase. Adv Enzyme Regul. 1986;25:125-39. [PubMed:2433905 ]
Newman DJ, Cragg GM: Natural products as sources of new drugs over the last 25 years. J Nat Prod. 2007 Mar;70(3):461-77. Epub 2007 Feb 20. [PubMed:17309302 ]
Cabanillas F: Purine nucleoside analogs in indolent non-Hodgkin's lymphoma. Oncology (Williston Park). 2000 Jun;14(6 Suppl 2):13-5. [PubMed:10887639 ]

Showing metabocard for Pentostatin (HMDB0014692)

MOL for HMDB0014692 (Pentostatin)

3D MOL for HMDB0014692 (Pentostatin)

3D SDF for HMDB0014692 (Pentostatin)

3D-SDF for HMDB0014692 (Pentostatin)

PDB for HMDB0014692 (Pentostatin)

3D PDB for HMDB0014692 (Pentostatin)

SMILES for HMDB0014692 (Pentostatin)

INCHI for HMDB0014692 (Pentostatin)

Structure for HMDB0014692 (Pentostatin)

3D Structure for HMDB0014692 (Pentostatin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

References