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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1)transporters (1) Show 2 proteins XML

enzymes (1)transporters (1) Show 2 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:50 UTC

HMDB ID

HMDB0015037

Secondary Accession Numbers

HMDB15037

Metabolite Identification

Common Name

Didanosine

Description

A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by a hydrogen. This modification prevents the formation of phosphodiester linkages which are needed for the completion of nucleic acid chains. Didanosine is a potent inhibitor of HIV replication, acting as a chain-terminator of viral DNA by binding to reverse transcriptase; ddI is then metabolized to dideoxyadenosine triphosphate, its putative active metabolite. [PubChem]

Structure

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

HMDB0015037
     RDKit          3D
Didanosine
 29 31  0  0  0  0  0  0  0  0999 V2000
    5.3851   -0.1442   -0.3950 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2226    0.3039   -0.2321 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0446    1.5880    0.1207 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7699    2.0138    0.2817 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7126    1.2015    0.1010 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8665   -0.0862   -0.2519 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1569   -0.5651   -0.4278 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0430   -1.8433   -0.7683 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7441   -2.1562   -0.8056 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9945   -1.0660   -0.4845 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4111   -1.0532   -0.4301 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0006   -0.8506    0.9526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4628   -0.8084    0.5381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3632   -0.1663   -0.8303 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1108    1.1431   -0.7871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5854    1.9832    0.1821 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0223   -0.0138   -1.1187 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6446    3.0515    0.5660 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7600    1.5949    0.2416 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3741   -3.1577   -1.0622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8607   -1.9946   -0.8106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7683    0.1325    1.3806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7859   -1.7030    1.6239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0722   -0.2125    1.2445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8683   -1.8425    0.4151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8013   -0.8071   -1.6217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1738    0.8990   -0.5800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0720    1.6698   -1.7665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3599    2.8896   -0.1991 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 14 17  1  0
  7  2  1  0
 17 11  1  0
 10  6  1  0
  4 18  1  0
  5 19  1  0
  9 20  1  0
 11 21  1  6
 12 22  1  0
 12 23  1  0
 13 24  1  0
 13 25  1  0
 14 26  1  6
 15 27  1  0
 15 28  1  0
 16 29  1  0
M  END

900
  Mrv0541 02231215052D          

 17 19  0  0  1  0            999 V2000
    3.6321    0.6079    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4177    2.6717    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -3.1584    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8596   -0.8446    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.6834    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8596   -2.1724    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.9209    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1158   -0.0604    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9009    0.1932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9024    1.0182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1182    1.2745    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8646    2.0596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -1.0959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3411   -1.5084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -1.9209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.3334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.0959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  8  1  0  0  0  0
  1 11  1  0  0  0  0
  2 12  1  0  0  0  0
  3 16  2  0  0  0  0
  8  4  1  6  0  0  0
  4 13  1  0  0  0  0
  4 14  1  0  0  0  0
  5 13  1  0  0  0  0
  5 17  1  0  0  0  0
  6 14  2  0  0  0  0
  6 15  1  0  0  0  0
  7 16  1  0  0  0  0
  7 17  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  0  0  0
 13 15  2  0  0  0  0
 15 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015037

> <DATABASE_NAME>
hmdb

> <SMILES>
OC[C@@H]1CC[C@@H](O1)N1C=NC2=C1NC=NC2=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H12N4O3/c15-3-6-1-2-7(17-6)14-5-13-8-9(14)11-4-12-10(8)16/h4-7,15H,1-3H2,(H,11,12,16)/t6-,7+/m0/s1

> <INCHI_KEY>
BXZVVICBKDXVGW-NKWVEPMBSA-N

> <FORMULA>
C10H12N4O3

> <MOLECULAR_WEIGHT>
236.2273

> <EXACT_MASS>
236.09094027

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
22.897494329326598

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
9-[(2R,5S)-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-3H-purin-6-one

> <ALOGPS_LOGP>
-0.99

> <JCHEM_LOGP>
-0.35163640833333387

> <ALOGPS_LOGS>
-1.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.672761682427211

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.9434804699499475

> <JCHEM_PKA_STRONGEST_BASIC>
2.754142082753731

> <JCHEM_POLAR_SURFACE_AREA>
88.74

> <JCHEM_REFRACTIVITY>
58.593799999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.58e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
didanosine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015037
     RDKit          3D
Didanosine
 29 31  0  0  0  0  0  0  0  0999 V2000
    5.3851   -0.1442   -0.3950 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2226    0.3039   -0.2321 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0446    1.5880    0.1207 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7699    2.0138    0.2817 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7126    1.2015    0.1010 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8665   -0.0862   -0.2519 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1569   -0.5651   -0.4278 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0430   -1.8433   -0.7683 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7441   -2.1562   -0.8056 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9945   -1.0660   -0.4845 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4111   -1.0532   -0.4301 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0006   -0.8506    0.9526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4628   -0.8084    0.5381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3632   -0.1663   -0.8303 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1108    1.1431   -0.7871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5854    1.9832    0.1821 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0223   -0.0138   -1.1187 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6446    3.0515    0.5660 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7600    1.5949    0.2416 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3741   -3.1577   -1.0622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8607   -1.9946   -0.8106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7683    0.1325    1.3806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7859   -1.7030    1.6239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0722   -0.2125    1.2445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8683   -1.8425    0.4151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8013   -0.8071   -1.6217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1738    0.8990   -0.5800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0720    1.6698   -1.7665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3599    2.8896   -0.1991 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 14 17  1  0
  7  2  1  0
 17 11  1  0
 10  6  1  0
  4 18  1  0
  5 19  1  0
  9 20  1  0
 11 21  1  6
 12 22  1  0
 12 23  1  0
 13 24  1  0
 13 25  1  0
 14 26  1  6
 15 27  1  0
 15 28  1  0
 16 29  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 900                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       6.780   1.135   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       8.246   4.987   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       4.414  -5.896   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       7.205  -1.577   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0       4.414  -1.276   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0       7.205  -4.055   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0       3.080  -3.586   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       7.683  -0.113   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.148   0.361   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.151   1.901   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.687   2.379   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.214   3.845   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.747  -2.046   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.103  -2.816   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.747  -3.586   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.414  -4.356   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.080  -2.046   0.000  0.00  0.00           C+0
CONECT    1    8   11                                                       
CONECT    2   12                                                            
CONECT    3   16                                                            
CONECT    4    8   13   14                                                  
CONECT    5   13   17                                                       
CONECT    6   14   15                                                       
CONECT    7   16   17                                                       
CONECT    8    1    4    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11    1   10   12                                                  
CONECT   12    2   11                                                       
CONECT   13    4    5   15                                                  
CONECT   14    4    6                                                       
CONECT   15    6   13   16                                                  
CONECT   16    3    7   15                                                  
CONECT   17    5    7                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   38    0
END

COMPND    HMDB0015037
HETATM    1  O1  UNL     1       5.385  -0.144  -0.395  1.00  0.00           O  
HETATM    2  C1  UNL     1       4.223   0.304  -0.232  1.00  0.00           C  
HETATM    3  N1  UNL     1       4.045   1.588   0.121  1.00  0.00           N  
HETATM    4  C2  UNL     1       2.770   2.014   0.282  1.00  0.00           C  
HETATM    5  N2  UNL     1       1.713   1.202   0.101  1.00  0.00           N  
HETATM    6  C3  UNL     1       1.867  -0.086  -0.252  1.00  0.00           C  
HETATM    7  C4  UNL     1       3.157  -0.565  -0.428  1.00  0.00           C  
HETATM    8  N3  UNL     1       3.043  -1.843  -0.768  1.00  0.00           N  
HETATM    9  C5  UNL     1       1.744  -2.156  -0.806  1.00  0.00           C  
HETATM   10  N4  UNL     1       0.994  -1.066  -0.484  1.00  0.00           N  
HETATM   11  C6  UNL     1      -0.411  -1.053  -0.430  1.00  0.00           C  
HETATM   12  C7  UNL     1      -1.001  -0.851   0.953  1.00  0.00           C  
HETATM   13  C8  UNL     1      -2.463  -0.808   0.538  1.00  0.00           C  
HETATM   14  C9  UNL     1      -2.363  -0.166  -0.830  1.00  0.00           C  
HETATM   15  C10 UNL     1      -3.111   1.143  -0.787  1.00  0.00           C  
HETATM   16  O2  UNL     1      -2.585   1.983   0.182  1.00  0.00           O  
HETATM   17  O3  UNL     1      -1.022  -0.014  -1.119  1.00  0.00           O  
HETATM   18  H1  UNL     1       2.645   3.051   0.566  1.00  0.00           H  
HETATM   19  H2  UNL     1       0.760   1.595   0.242  1.00  0.00           H  
HETATM   20  H3  UNL     1       1.374  -3.158  -1.062  1.00  0.00           H  
HETATM   21  H4  UNL     1      -0.861  -1.995  -0.811  1.00  0.00           H  
HETATM   22  H5  UNL     1      -0.768   0.133   1.381  1.00  0.00           H  
HETATM   23  H6  UNL     1      -0.786  -1.703   1.624  1.00  0.00           H  
HETATM   24  H7  UNL     1      -3.072  -0.213   1.244  1.00  0.00           H  
HETATM   25  H8  UNL     1      -2.868  -1.842   0.415  1.00  0.00           H  
HETATM   26  H9  UNL     1      -2.801  -0.807  -1.622  1.00  0.00           H  
HETATM   27  H10 UNL     1      -4.174   0.899  -0.580  1.00  0.00           H  
HETATM   28  H11 UNL     1      -3.072   1.670  -1.766  1.00  0.00           H  
HETATM   29  H12 UNL     1      -2.360   2.890  -0.199  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    7
CONECT    3    4    4
CONECT    4    5   18
CONECT    5    6   19
CONECT    6    7    7   10
CONECT    7    8
CONECT    8    9    9
CONECT    9   10   20
CONECT   10   11
CONECT   11   12   17   21
CONECT   12   13   22   23
CONECT   13   14   24   25
CONECT   14   15   17   26
CONECT   15   16   27   28
CONECT   16   29
END

HMDB0015037
     RDKit          3D
Didanosine
 29 31  0  0  0  0  0  0  0  0999 V2000
    5.3851   -0.1442   -0.3950 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2226    0.3039   -0.2321 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0446    1.5880    0.1207 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7699    2.0138    0.2817 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7126    1.2015    0.1010 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8665   -0.0862   -0.2519 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1569   -0.5651   -0.4278 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0430   -1.8433   -0.7683 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7441   -2.1562   -0.8056 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9945   -1.0660   -0.4845 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4111   -1.0532   -0.4301 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0006   -0.8506    0.9526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4628   -0.8084    0.5381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3632   -0.1663   -0.8303 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1108    1.1431   -0.7871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5854    1.9832    0.1821 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0223   -0.0138   -1.1187 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6446    3.0515    0.5660 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7600    1.5949    0.2416 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3741   -3.1577   -1.0622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8607   -1.9946   -0.8106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7683    0.1325    1.3806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7859   -1.7030    1.6239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0722   -0.2125    1.2445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8683   -1.8425    0.4151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8013   -0.8071   -1.6217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1738    0.8990   -0.5800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0720    1.6698   -1.7665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3599    2.8896   -0.1991 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 14 17  1  0
  7  2  1  0
 17 11  1  0
 10  6  1  0
  4 18  1  0
  5 19  1  0
  9 20  1  0
 11 21  1  6
 12 22  1  0
 12 23  1  0
 13 24  1  0
 13 25  1  0
 14 26  1  6
 15 27  1  0
 15 28  1  0
 16 29  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2,3-Dideoxyinosine	ChEBI
9-((2R,5S)-5-(Hydroxymethyl)-tetrahydrofuran-2-yl)-1H-purin-6(9H)-one	ChEBI
9-((2R,5S)-5-Hydroxymethyl-tetrahydro-furan-2-yl)-1,9-dihydro-purin-6-one	ChEBI
9-((2S,5R)-5-Hydroxymethyl-tetrahydro-furan-2-yl)-9H-purin-6-ol	ChEBI
9-[(2R,5S)-5-(Hydroxymethyl)tetrahydrofuran-2-yl]-1,9-dihydro-6H-purin-6-one	ChEBI
DDI	ChEBI
DdIno	ChEBI
Didanosina	ChEBI
Didanosinum	ChEBI
Dideoxyinosine	ChEBI
Videx	Kegg
ABBR ddi	Kegg
2',3' Dideoxyinosine	HMDB
Bristol-myers brand OF didanosine	HMDB
DdI (antiviral)	HMDB
Bristol myers squibb brand OF didanosine	HMDB
2',3'-Dideoxyinosine	HMDB
Bristol myers brand OF didanosine	HMDB
Bristol-myers squibb brand OF didanosine	HMDB

Chemical Formula

C₁₀H₁₂N₄O₃

Average Molecular Weight

236.2273

Monoisotopic Molecular Weight

236.09094027

IUPAC Name

9-[(2R,5S)-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-3H-purin-6-one

Traditional Name

didanosine

CAS Registry Number

69655-05-6

SMILES

OC[C@@H]1CC[C@@H](O1)N1C=NC2=C1NC=NC2=O

InChI Identifier

InChI=1S/C10H12N4O3/c15-3-6-1-2-7(17-6)14-5-13-8-9(14)11-4-12-10(8)16/h4-7,15H,1-3H2,(H,11,12,16)/t6-,7+/m0/s1

InChI Key

BXZVVICBKDXVGW-NKWVEPMBSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as purine 2',3'-dideoxyribonucleosides. Purine 2',3'-dideoxyribonucleosides are compounds consisting of a purine linked to a ribose which lacks a hydroxyl group at positions 2 and 3.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Purine nucleosides

Sub Class

Purine 2',3'-dideoxyribonucleosides

Direct Parent

Purine 2',3'-dideoxyribonucleosides

Alternative Parents

Substituents

Purine 2',3'-dideoxyribonucleoside
6-oxopurine
Hypoxanthine
Purinone
Imidazopyrimidine
Purine
Pyrimidone
N-substituted imidazole
Pyrimidine
Heteroaromatic compound
Azole
Imidazole
Tetrahydrofuran
Vinylogous amide
Oxacycle
Azacycle
Organoheterocyclic compound
Alcohol
Organopnictogen compound
Primary alcohol
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

purine 2',3'-dideoxyribonucleoside (CHEBI:490877 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Blood (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0015037)
extracellular (HMDB: HMDB0015037)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Didanosine Action Pathway (PathBank: SMP0000739)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	160 - 163 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	6.58 g/L	Not Available
LogP	-0.2	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	6.58 g/L	ALOGPS
logP	-0.99	ALOGPS
logP	-0.35	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	6.94	ChemAxon
pKa (Strongest Basic)	2.75	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	88.74 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	58.59 m³·mol⁻¹	ChemAxon
Polarizability	22.9 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	153.34	31661259
DarkChem	[M-H]-	153.739	31661259
DeepCCS	[M+H]+	148.698	30932474
DeepCCS	[M-H]-	146.302	30932474
DeepCCS	[M-2H]-	179.62	30932474
DeepCCS	[M+Na]+	154.61	30932474
AllCCS	[M+H]+	152.9	32859911
AllCCS	[M+H-H2O]+	149.0	32859911
AllCCS	[M+NH4]+	156.5	32859911
AllCCS	[M+Na]+	157.5	32859911
AllCCS	[M-H]-	154.1	32859911
AllCCS	[M+Na-2H]-	153.8	32859911
AllCCS	[M+HCOO]-	153.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Didanosine	OC[C@@H]1CC[C@@H](O1)N1C=NC2=C1NC=NC2=O	3067.6	Standard polar	33892256
Didanosine	OC[C@@H]1CC[C@@H](O1)N1C=NC2=C1NC=NC2=O	2281.6	Standard non polar	33892256
Didanosine	OC[C@@H]1CC[C@@H](O1)N1C=NC2=C1NC=NC2=O	2618.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Didanosine,1TMS,isomer #1	C[Si](C)(C)OC[C@@H]1CC[C@H](N2C=NC3=C2[NH]C=NC3=O)O1	2317.4	Semi standard non polar	33892256
Didanosine,1TMS,isomer #2	C[Si](C)(C)N1C=NC(=O)C2=C1N([C@H]1CC[C@@H](CO)O1)C=N2	2448.2	Semi standard non polar	33892256
Didanosine,2TMS,isomer #1	C[Si](C)(C)OC[C@@H]1CC[C@H](N2C=NC3=C2N([Si](C)(C)C)C=NC3=O)O1	2428.1	Semi standard non polar	33892256
Didanosine,2TMS,isomer #1	C[Si](C)(C)OC[C@@H]1CC[C@H](N2C=NC3=C2N([Si](C)(C)C)C=NC3=O)O1	2603.7	Standard non polar	33892256
Didanosine,2TMS,isomer #1	C[Si](C)(C)OC[C@@H]1CC[C@H](N2C=NC3=C2N([Si](C)(C)C)C=NC3=O)O1	3273.0	Standard polar	33892256
Didanosine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@@H]1CC[C@H](N2C=NC3=C2[NH]C=NC3=O)O1	2542.5	Semi standard non polar	33892256
Didanosine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C=NC(=O)C2=C1N([C@H]1CC[C@@H](CO)O1)C=N2	2665.6	Semi standard non polar	33892256
Didanosine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@@H]1CC[C@H](N2C=NC3=C2N([Si](C)(C)C(C)(C)C)C=NC3=O)O1	2818.3	Semi standard non polar	33892256
Didanosine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@@H]1CC[C@H](N2C=NC3=C2N([Si](C)(C)C(C)(C)C)C=NC3=O)O1	3019.2	Standard non polar	33892256
Didanosine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@@H]1CC[C@H](N2C=NC3=C2N([Si](C)(C)C(C)(C)C)C=NC3=O)O1	3321.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Didanosine GC-MS (Non-derivatized) - 70eV, Positive	splash10-056u-9670000000-b8e1fdd18fda2c412cef	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Didanosine GC-MS (1 TMS) - 70eV, Positive	splash10-005c-7090000000-ed6dc7eca7c11c73693a	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Didanosine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Didanosine 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 - Didanosine LC-ESI-QFT , negative-QTOF	splash10-000i-0090000000-fed0a8ffc5839fe73fe1	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Didanosine LC-ESI-QFT , negative-QTOF	splash10-000i-0490000000-0ac04c4f4e817e6da391	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Didanosine LC-ESI-QFT , negative-QTOF	splash10-000i-0920000000-14a23956c10d3f6e7e9a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Didanosine LC-ESI-QFT , negative-QTOF	splash10-000i-0900000000-de4599cfceaa46089291	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Didanosine LC-ESI-QFT , negative-QTOF	splash10-000i-1900000000-10d07c81e3fc72fcfef2	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Didanosine LC-ESI-QFT , negative-QTOF	splash10-000i-1900000000-84e8bb1bea77e6b5bfca	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Didanosine LC-ESI-QFT , positive-QTOF	splash10-000i-0900000000-6a0516d1b3cec255e050	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Didanosine LC-ESI-QFT , positive-QTOF	splash10-000i-0900000000-fd0dfb766f1c628d170d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Didanosine LC-ESI-QFT , positive-QTOF	splash10-000i-0900000000-3d9e0ecfaf77d867a9d9	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Didanosine LC-ESI-QFT , positive-QTOF	splash10-000i-0900000000-e0e7d0c808e14d842dbb	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Didanosine LC-ESI-QFT , positive-QTOF	splash10-000i-1900000000-9d4b77c3e99e9f9a2c2a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Didanosine LC-ESI-QFT , positive-QTOF	splash10-000i-1900000000-2bb63f71ec2e92ce075d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Didanosine 90V, Negative-QTOF	splash10-000i-1900000000-1475736d859ee324d92e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Didanosine 75V, Negative-QTOF	splash10-000i-0900000000-2cd1a2d12ed969154415	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Didanosine 45V, Negative-QTOF	splash10-000i-0920000000-410013d0d67e872eea6b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Didanosine 60V, Negative-QTOF	splash10-000i-0900000000-544cf7886920f267da7a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Didanosine 45V, Positive-QTOF	splash10-000i-0900000000-74008fe84aaa4adb23ed	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Didanosine 60V, Positive-QTOF	splash10-000i-0900000000-532725f06bed9d035dcf	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Didanosine 90V, Positive-QTOF	splash10-000i-1900000000-7d5a4e68524522f15eca	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Didanosine 10V, Positive-QTOF	splash10-000i-0920000000-a89fd678ed8a8c16accc	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Didanosine 20V, Positive-QTOF	splash10-000i-0900000000-a1a5b268d419fff83602	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Didanosine 40V, Positive-QTOF	splash10-03dr-1900000000-32bbc23c752210d7cd6f	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Didanosine 10V, Negative-QTOF	splash10-000i-0190000000-383b44cf919dd28ff3bb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Didanosine 20V, Negative-QTOF	splash10-000i-2940000000-309e7293be866f0e29aa	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Didanosine 40V, Negative-QTOF	splash10-052u-3900000000-0828603c96a200af867a	2016-08-03	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Didanosine Action Pathway		Not Available

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 DB00900	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00900	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

DB00900

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

45864

KEGG Compound ID

C06953

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Didanosine

METLIN ID

Not Available

PubChem Compound

50599

PDB ID

2DI

ChEBI ID

490877

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

Not Available

Enzymes

Enzyme Details

1. Purine nucleoside phosphorylase

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

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]

Transporters

Enzyme Details

1. Solute carrier family 22 member 6

General function:: Involved in ion transmembrane transporter activity
Specific function:: Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one molecule of endogenous dicarboxylic acid (glutarate, ketoglutarate, etc). Mediates the sodium-independent uptake of 2,3-dimercapto-1-propanesulfonic acid (DMPS). Mediates the sodium-independent uptake of p- aminohippurate (PAH), ochratoxin (OTA), acyclovir (ACV), 3'-azido- 3-'deoxythymidine (AZT), cimetidine (CMD), 2,4-dichloro- phenoxyacetate (2,4-D), hippurate (HA), indoleacetate (IA), indoxyl sulfate (IS) and 3-carboxy-4-methyl-5-propyl-2- furanpropionate (CMPF), cidofovir, adefovir, 9-(2- phosphonylmethoxyethyl) guanine (PMEG), 9-(2- phosphonylmethoxyethyl) diaminopurine (PMEDAP) and edaravone sulfate. PAH uptake is inhibited by p- chloromercuribenzenesulphonate (PCMBS), diethyl pyrocarbonate (DEPC), sulindac, diclofenac, carprofen, glutarate and okadaic acid. PAH uptake is inhibited by benzothiazolylcysteine (BTC), S-chlorotrifluoroethylcysteine (CTFC), cysteine S-conjugates S-dichlorovinylcysteine (DCVC), furosemide, steviol, phorbol 12-myristate 13-acetate (PMA), calcium ionophore A23187, benzylpenicillin, furosemide, indomethacin, bumetamide, losartan, probenecid, phenol red, urate, and alpha-ketoglutarate
Gene Name:: SLC22A6
Uniprot ID:: Q4U2R8
Molecular weight:: 61815.8

References

Wada S, Tsuda M, Sekine T, Cha SH, Kimura M, Kanai Y, Endou H: Rat multispecific organic anion transporter 1 (rOAT1) transports zidovudine, acyclovir, and other antiviral nucleoside analogs. J Pharmacol Exp Ther. 2000 Sep;294(3):844-9. [PubMed:10945832 ]

Showing metabocard for Didanosine (HMDB0015037)

MOL for HMDB0015037 (Didanosine)

3D MOL for HMDB0015037 (Didanosine)

3D SDF for HMDB0015037 (Didanosine)

3D-SDF for HMDB0015037 (Didanosine)

PDB for HMDB0015037 (Didanosine)

3D PDB for HMDB0015037 (Didanosine)

SMILES for HMDB0015037 (Didanosine)

INCHI for HMDB0015037 (Didanosine)

Structure for HMDB0015037 (Didanosine)

3D Structure for HMDB0015037 (Didanosine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

References

Transporters

References