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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (4)transporters (2) Show 6 proteins XML

enzymes (4)transporters (2) Show 6 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2022-03-07 02:51:48 UTC

HMDB ID

HMDB0014949

Secondary Accession Numbers

HMDB14949

Metabolite Identification

Common Name

Ribavirin

Description

Ribavirin is only found in individuals that have used or taken this drug. It is a nucleoside antimetabolite antiviral agent that blocks nucleic acid synthesis and is used against both RNA and DNA viruses. [PubChem]Ribavirin is readily phosphorylated intracellularly by adenosine kinase to ribavirin mono-, di-, and triphosphate metabolites. Ribavirin triphosphate (RTP) is a potent competitive inhibitor of inosine monophosphate (IMP) dehydrogenase, viral RNA polymerase and messenger RNA (mRNA) guanylyltransferase (viral) and can be incorporated into RNA in RNA viral species. Guanylyltranserase inhibition stops the capping of mRNA. These diverse effects result in a marked reduction of intracellular guanosine triphosphate (GTP) pools and inhibition of viral RNA and protein synthesis. Ribavirin is also incorporated into the viral genome causing lethal mutagenesis and a subsequent decrease in specific viral infectivity.

Structure

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

HMDB0014949
     RDKit          3D
Ribavirin
 29 30  0  0  0  0  0  0  0  0999 V2000
    4.6229    0.9360   -0.4374 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1091   -0.3892   -0.3842 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8793   -1.3147   -0.7424 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7580   -0.6630    0.0627 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2191   -1.8922    0.1339 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9726   -1.7698    0.5820 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7191   -0.4581    0.7962 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5584    0.0041    1.2877 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5692   -0.7688    0.7867 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1186   -0.1661   -0.3061 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9612   -1.0111   -1.5387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5871   -2.2250   -1.3525 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5382    1.2009   -0.4625 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5123    2.1681   -0.6393 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8748    1.4141    0.9021 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9035    1.8650    1.7487 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8062    0.1914    0.4776 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3661    1.5370   -1.2448 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2425    1.3079    0.3077 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2930   -2.6071    0.7399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5760   -0.0590    2.4023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2278   -0.0680   -0.1244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8749   -1.1162   -1.7930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4557   -0.5204   -2.4110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8691   -2.4135   -0.4391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7681    1.2468   -1.2567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9912    2.3698    0.1913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0259    2.0896    0.8570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5758    1.1114    1.7429 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 10 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
  7 17  1  0
 17  4  2  0
 15  8  1  0
  1 18  1  0
  1 19  1  0
  6 20  1  0
  8 21  1  1
 10 22  1  1
 11 23  1  0
 11 24  1  0
 12 25  1  0
 13 26  1  6
 14 27  1  0
 15 28  1  6
 16 29  1  0
M  END

811
  Mrv0541 02231215012D          

 17 18  0  0  1  0            999 V2000
    4.1496   -1.2476    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0301   -0.9926    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5847   -2.6996    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2001   -2.6134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2001    1.9132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4822    0.0624    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1496    0.5473    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0697    1.3320    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0441    2.7530    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0697   -2.0322    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8147   -1.2476    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8947   -2.0322    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4822   -0.7626    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3796   -2.6996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8147    0.5473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8947    1.3320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3796    1.9994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 12  1  0  0  0  0
  1 13  1  0  0  0  0
 11  2  1  1  0  0  0
 10  3  1  1  0  0  0
  4 14  1  0  0  0  0
  5 17  2  0  0  0  0
  6  7  1  0  0  0  0
 13  6  1  6  0  0  0
  6 15  1  0  0  0  0
  7 16  2  0  0  0  0
  8 15  2  0  0  0  0
  8 16  1  0  0  0  0
  9 17  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 11 13  1  0  0  0  0
 12 14  1  6  0  0  0
 16 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014949

> <DATABASE_NAME>
hmdb

> <SMILES>
NC(=O)C1=NN(C=N1)[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C8H12N4O5/c9-6(16)7-10-2-12(11-7)8-5(15)4(14)3(1-13)17-8/h2-5,8,13-15H,1H2,(H2,9,16)/t3-,4-,5-,8-/m1/s1

> <INCHI_KEY>
IWUCXVSUMQZMFG-AFCXAGJDSA-N

> <FORMULA>
C8H12N4O5

> <MOLECULAR_WEIGHT>
244.2047

> <EXACT_MASS>
244.080769514

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
22.18338685084327

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-1,2,4-triazole-3-carboxamide

> <ALOGPS_LOGP>
-1.92

> <JCHEM_LOGP>
-2.7682973950000003

> <ALOGPS_LOGS>
-0.87

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.56172463454537

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.878700833908908

> <JCHEM_PKA_STRONGEST_BASIC>
-1.1726982699341972

> <JCHEM_POLAR_SURFACE_AREA>
143.72000000000003

> <JCHEM_REFRACTIVITY>
64.5744

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.32e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ribavirin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014949
     RDKit          3D
Ribavirin
 29 30  0  0  0  0  0  0  0  0999 V2000
    4.6229    0.9360   -0.4374 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1091   -0.3892   -0.3842 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8793   -1.3147   -0.7424 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7580   -0.6630    0.0627 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2191   -1.8922    0.1339 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9726   -1.7698    0.5820 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7191   -0.4581    0.7962 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5584    0.0041    1.2877 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5692   -0.7688    0.7867 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1186   -0.1661   -0.3061 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9612   -1.0111   -1.5387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5871   -2.2250   -1.3525 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5382    1.2009   -0.4625 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5123    2.1681   -0.6393 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8748    1.4141    0.9021 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9035    1.8650    1.7487 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8062    0.1914    0.4776 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3661    1.5370   -1.2448 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2425    1.3079    0.3077 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2930   -2.6071    0.7399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5760   -0.0590    2.4023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2278   -0.0680   -0.1244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8749   -1.1162   -1.7930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4557   -0.5204   -2.4110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8691   -2.4135   -0.4391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7681    1.2468   -1.2567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9912    2.3698    0.1913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0259    2.0896    0.8570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5758    1.1114    1.7429 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 10 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
  7 17  1  0
 17  4  2  0
 15  8  1  0
  1 18  1  0
  1 19  1  0
  6 20  1  0
  8 21  1  1
 10 22  1  1
 11 23  1  0
 11 24  1  0
 12 25  1  0
 13 26  1  6
 14 27  1  0
 15 28  1  6
 16 29  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 811                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       7.746  -2.329   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       3.790  -1.853   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       4.825  -5.039   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       9.707  -4.878   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       9.707   3.571   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0       6.500   0.116   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0       7.746   1.022   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0       5.730   2.486   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0       7.549   5.139   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       5.730  -3.793   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.254  -2.329   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.270  -3.793   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.500  -1.424   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.175  -5.039   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.254   1.022   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.270   2.486   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.175   3.732   0.000  0.00  0.00           C+0
CONECT    1   12   13                                                       
CONECT    2   11                                                            
CONECT    3   10                                                            
CONECT    4   14                                                            
CONECT    5   17                                                            
CONECT    6    7   13   15                                                  
CONECT    7    6   16                                                       
CONECT    8   15   16                                                       
CONECT    9   17                                                            
CONECT   10    3   11   12                                                  
CONECT   11    2   10   13                                                  
CONECT   12    1   10   14                                                  
CONECT   13    1    6   11                                                  
CONECT   14    4   12                                                       
CONECT   15    6    8                                                       
CONECT   16    7    8   17                                                  
CONECT   17    5    9   16                                                  
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

COMPND    HMDB0014949
HETATM    1  N1  UNL     1       4.623   0.936  -0.437  1.00  0.00           N  
HETATM    2  C1  UNL     1       4.109  -0.389  -0.384  1.00  0.00           C  
HETATM    3  O1  UNL     1       4.879  -1.315  -0.742  1.00  0.00           O  
HETATM    4  C2  UNL     1       2.758  -0.663   0.063  1.00  0.00           C  
HETATM    5  N2  UNL     1       2.219  -1.892   0.134  1.00  0.00           N  
HETATM    6  C3  UNL     1       0.973  -1.770   0.582  1.00  0.00           C  
HETATM    7  N3  UNL     1       0.719  -0.458   0.796  1.00  0.00           N  
HETATM    8  C4  UNL     1      -0.558   0.004   1.288  1.00  0.00           C  
HETATM    9  O2  UNL     1      -1.569  -0.769   0.787  1.00  0.00           O  
HETATM   10  C5  UNL     1      -2.119  -0.166  -0.306  1.00  0.00           C  
HETATM   11  C6  UNL     1      -1.961  -1.011  -1.539  1.00  0.00           C  
HETATM   12  O3  UNL     1      -2.587  -2.225  -1.352  1.00  0.00           O  
HETATM   13  C7  UNL     1      -1.538   1.201  -0.463  1.00  0.00           C  
HETATM   14  O4  UNL     1      -2.512   2.168  -0.639  1.00  0.00           O  
HETATM   15  C8  UNL     1      -0.875   1.414   0.902  1.00  0.00           C  
HETATM   16  O5  UNL     1      -1.904   1.865   1.749  1.00  0.00           O  
HETATM   17  N4  UNL     1       1.806   0.191   0.478  1.00  0.00           N  
HETATM   18  H1  UNL     1       4.366   1.537  -1.245  1.00  0.00           H  
HETATM   19  H2  UNL     1       5.242   1.308   0.308  1.00  0.00           H  
HETATM   20  H3  UNL     1       0.293  -2.607   0.740  1.00  0.00           H  
HETATM   21  H4  UNL     1      -0.576  -0.059   2.402  1.00  0.00           H  
HETATM   22  H5  UNL     1      -3.228  -0.068  -0.124  1.00  0.00           H  
HETATM   23  H6  UNL     1      -0.875  -1.116  -1.793  1.00  0.00           H  
HETATM   24  H7  UNL     1      -2.456  -0.520  -2.411  1.00  0.00           H  
HETATM   25  H8  UNL     1      -2.869  -2.413  -0.439  1.00  0.00           H  
HETATM   26  H9  UNL     1      -0.768   1.247  -1.257  1.00  0.00           H  
HETATM   27  H10 UNL     1      -2.991   2.370   0.191  1.00  0.00           H  
HETATM   28  H11 UNL     1      -0.026   2.090   0.857  1.00  0.00           H  
HETATM   29  H12 UNL     1      -2.576   1.111   1.743  1.00  0.00           H  
CONECT    1    2   18   19
CONECT    2    3    3    4
CONECT    4    5   17   17
CONECT    5    6    6
CONECT    6    7   20
CONECT    7    8   17
CONECT    8    9   15   21
CONECT    9   10
CONECT   10   11   13   22
CONECT   11   12   23   24
CONECT   12   25
CONECT   13   14   15   26
CONECT   14   27
CONECT   15   16   28
CONECT   16   29
END

HMDB0014949
     RDKit          3D
Ribavirin
 29 30  0  0  0  0  0  0  0  0999 V2000
    4.6229    0.9360   -0.4374 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1091   -0.3892   -0.3842 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8793   -1.3147   -0.7424 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7580   -0.6630    0.0627 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2191   -1.8922    0.1339 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9726   -1.7698    0.5820 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7191   -0.4581    0.7962 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5584    0.0041    1.2877 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5692   -0.7688    0.7867 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1186   -0.1661   -0.3061 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9612   -1.0111   -1.5387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5871   -2.2250   -1.3525 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5382    1.2009   -0.4625 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5123    2.1681   -0.6393 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8748    1.4141    0.9021 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9035    1.8650    1.7487 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8062    0.1914    0.4776 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3661    1.5370   -1.2448 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2425    1.3079    0.3077 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2930   -2.6071    0.7399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5760   -0.0590    2.4023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2278   -0.0680   -0.1244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8749   -1.1162   -1.7930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4557   -0.5204   -2.4110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8691   -2.4135   -0.4391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7681    1.2468   -1.2567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9912    2.3698    0.1913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0259    2.0896    0.8570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5758    1.1114    1.7429 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 10 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
  7 17  1  0
 17  4  2  0
 15  8  1  0
  1 18  1  0
  1 19  1  0
  6 20  1  0
  8 21  1  1
 10 22  1  1
 11 23  1  0
 11 24  1  0
 12 25  1  0
 13 26  1  6
 14 27  1  0
 15 28  1  6
 16 29  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
1-beta-D-Ribofuranosyl-1,2,4-triazole-3-carboxamide	ChEBI
1-beta-D-Ribofuranosyl-1H-1,2,4-triazole-3-carboxamide	ChEBI
RBV	ChEBI
Ribavirina	ChEBI
Ribavirine	ChEBI
Ribavirinum	ChEBI
Copegus	Kegg
Rebetol	Kegg
Ribasphere	Kegg
Virazole	Kegg
1-b-D-Ribofuranosyl-1,2,4-triazole-3-carboxamide	Generator
1-Β-D-ribofuranosyl-1,2,4-triazole-3-carboxamide	Generator
1-b-D-Ribofuranosyl-1H-1,2,4-triazole-3-carboxamide	Generator
1-Β-D-ribofuranosyl-1H-1,2,4-triazole-3-carboxamide	Generator
Vilona	HMDB
ICN brand OF ribavirin	HMDB
Ribamide	HMDB
Ribamidyl	HMDB
Ribavirin merck brand	HMDB
Virazide	HMDB
Grossman brand OF ribavirin	HMDB
Merck brand OF ribavirin	HMDB
Pfizer brand OF ribavirin	HMDB
Ribovirin	HMDB
Three rivers pharmaceuticals brand OF ribavirin	HMDB
Dermatech brand OF ribavirin	HMDB
Essex brand OF ribavirin	HMDB
Ribamidil	HMDB
Tribavirin	HMDB
Viramide	HMDB

Chemical Formula

C₈H₁₂N₄O₅

Average Molecular Weight

244.2047

Monoisotopic Molecular Weight

244.080769514

IUPAC Name

1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-1,2,4-triazole-3-carboxamide

Traditional Name

ribavirin

CAS Registry Number

36791-04-5

SMILES

NC(=O)C1=NN(C=N1)[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O

InChI Identifier

InChI=1S/C8H12N4O5/c9-6(16)7-10-2-12(11-7)8-5(15)4(14)3(1-13)17-8/h2-5,8,13-15H,1H2,(H2,9,16)/t3-,4-,5-,8-/m1/s1

InChI Key

IWUCXVSUMQZMFG-AFCXAGJDSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triazole ribonucleosides and ribonucleotides. These are nucleoside derivatives containing a ribose (or deoxyribose) moiety which is N-glycosylated to a triazole. Nucleotides have a phosphate group linked to the C5 carbon of the ribose (or deoxyribose) moiety.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Triazole ribonucleosides and ribonucleotides

Sub Class

Not Available

Direct Parent

Triazole ribonucleosides and ribonucleotides

Alternative Parents

Substituents

N-ribosyl-1,2,4-triazole
Glycosyl compound
N-glycosyl compound
Pentose monosaccharide
2-heteroaryl carboxamide
Monosaccharide
Azole
Tetrahydrofuran
Triazole
1,2,4-triazole
Heteroaromatic compound
Carboxamide group
Secondary alcohol
Primary carboxylic acid amide
Carboxylic acid derivative
Oxacycle
Azacycle
Organoheterocyclic compound
Alcohol
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Primary alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

monocarboxylic acid amide (CHEBI:63580 )
aromatic amide (CHEBI:63580 )
1-ribosyltriazole (CHEBI:63580 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0014949)
Membrane (HMDB: HMDB0014949)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	174 - 176 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	33.2 g/L	Not Available
LogP	-2.6	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	33.2 g/L	ALOGPS
logP	-1.9	ALOGPS
logP	-2.8	ChemAxon
logS	-0.87	ALOGPS
pKa (Strongest Acidic)	11.88	ChemAxon
pKa (Strongest Basic)	-1.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	143.72 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	64.57 m³·mol⁻¹	ChemAxon
Polarizability	22.18 Å³	ChemAxon
Number of Rings	2	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]+	154.548	31661259
DarkChem	[M-H]-	152.184	31661259
DeepCCS	[M+H]+	150.125	30932474
DeepCCS	[M-H]-	147.729	30932474
DeepCCS	[M-2H]-	182.048	30932474
DeepCCS	[M+Na]+	156.878	30932474
AllCCS	[M+H]+	154.6	32859911
AllCCS	[M+H-H2O]+	150.8	32859911
AllCCS	[M+NH4]+	158.1	32859911
AllCCS	[M+Na]+	159.1	32859911
AllCCS	[M-H]-	151.6	32859911
AllCCS	[M+Na-2H]-	151.5	32859911
AllCCS	[M+HCOO]-	151.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Ribavirin	NC(=O)C1=NN(C=N1)[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O	2826.3	Standard polar	33892256
Ribavirin	NC(=O)C1=NN(C=N1)[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O	2044.0	Standard non polar	33892256
Ribavirin	NC(=O)C1=NN(C=N1)[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O	2367.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Ribavirin,1TMS,isomer #1	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC(C(N)=O)=N2)[C@H](O)[C@@H]1O	2432.9	Semi standard non polar	33892256
Ribavirin,1TMS,isomer #2	C[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](N2C=NC(C(N)=O)=N2)[C@@H]1O	2392.7	Semi standard non polar	33892256
Ribavirin,1TMS,isomer #3	C[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C=NC(C(N)=O)=N1	2404.5	Semi standard non polar	33892256
Ribavirin,1TMS,isomer #4	C[Si](C)(C)NC(=O)C1=NN([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)C=N1	2445.3	Semi standard non polar	33892256
Ribavirin,2TMS,isomer #1	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC(C(N)=O)=N2)[C@H](O[Si](C)(C)C)[C@@H]1O	2394.2	Semi standard non polar	33892256
Ribavirin,2TMS,isomer #2	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC(C(N)=O)=N2)[C@H](O)[C@@H]1O[Si](C)(C)C	2394.1	Semi standard non polar	33892256
Ribavirin,2TMS,isomer #3	C[Si](C)(C)NC(=O)C1=NN([C@@H]2O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@H]2O)C=N1	2436.3	Semi standard non polar	33892256
Ribavirin,2TMS,isomer #4	C[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](N2C=NC(C(N)=O)=N2)[C@@H]1O[Si](C)(C)C	2356.1	Semi standard non polar	33892256
Ribavirin,2TMS,isomer #5	C[Si](C)(C)NC(=O)C1=NN([C@@H]2O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H]2O)C=N1	2426.9	Semi standard non polar	33892256
Ribavirin,2TMS,isomer #6	C[Si](C)(C)NC(=O)C1=NN([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O[Si](C)(C)C)C=N1	2422.7	Semi standard non polar	33892256
Ribavirin,2TMS,isomer #7	C[Si](C)(C)N(C(=O)C1=NN([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)C=N1)[Si](C)(C)C	2485.9	Semi standard non polar	33892256
Ribavirin,3TMS,isomer #1	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC(C(N)=O)=N2)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	2348.5	Semi standard non polar	33892256
Ribavirin,3TMS,isomer #2	C[Si](C)(C)NC(=O)C1=NN([C@@H]2O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@H]2O[Si](C)(C)C)C=N1	2414.4	Semi standard non polar	33892256
Ribavirin,3TMS,isomer #3	C[Si](C)(C)NC(=O)C1=NN([C@@H]2O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]2O)C=N1	2408.1	Semi standard non polar	33892256
Ribavirin,3TMS,isomer #4	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC(C(=O)N([Si](C)(C)C)[Si](C)(C)C)=N2)[C@H](O)[C@@H]1O	2466.3	Semi standard non polar	33892256
Ribavirin,3TMS,isomer #5	C[Si](C)(C)NC(=O)C1=NN([C@@H]2O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)C=N1	2393.5	Semi standard non polar	33892256
Ribavirin,3TMS,isomer #6	C[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](N2C=NC(C(=O)N([Si](C)(C)C)[Si](C)(C)C)=N2)[C@@H]1O	2457.0	Semi standard non polar	33892256
Ribavirin,3TMS,isomer #7	C[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C=NC(C(=O)N([Si](C)(C)C)[Si](C)(C)C)=N1	2450.6	Semi standard non polar	33892256
Ribavirin,4TMS,isomer #1	C[Si](C)(C)NC(=O)C1=NN([C@@H]2O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)C=N1	2414.5	Semi standard non polar	33892256
Ribavirin,4TMS,isomer #1	C[Si](C)(C)NC(=O)C1=NN([C@@H]2O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)C=N1	2390.2	Standard non polar	33892256
Ribavirin,4TMS,isomer #1	C[Si](C)(C)NC(=O)C1=NN([C@@H]2O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)C=N1	3677.5	Standard polar	33892256
Ribavirin,4TMS,isomer #2	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC(C(=O)N([Si](C)(C)C)[Si](C)(C)C)=N2)[C@H](O[Si](C)(C)C)[C@@H]1O	2473.9	Semi standard non polar	33892256
Ribavirin,4TMS,isomer #2	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC(C(=O)N([Si](C)(C)C)[Si](C)(C)C)=N2)[C@H](O[Si](C)(C)C)[C@@H]1O	2518.5	Standard non polar	33892256
Ribavirin,4TMS,isomer #2	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC(C(=O)N([Si](C)(C)C)[Si](C)(C)C)=N2)[C@H](O[Si](C)(C)C)[C@@H]1O	3227.9	Standard polar	33892256
Ribavirin,4TMS,isomer #3	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC(C(=O)N([Si](C)(C)C)[Si](C)(C)C)=N2)[C@H](O)[C@@H]1O[Si](C)(C)C	2457.0	Semi standard non polar	33892256
Ribavirin,4TMS,isomer #3	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC(C(=O)N([Si](C)(C)C)[Si](C)(C)C)=N2)[C@H](O)[C@@H]1O[Si](C)(C)C	2497.9	Standard non polar	33892256
Ribavirin,4TMS,isomer #3	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC(C(=O)N([Si](C)(C)C)[Si](C)(C)C)=N2)[C@H](O)[C@@H]1O[Si](C)(C)C	3153.1	Standard polar	33892256
Ribavirin,4TMS,isomer #4	C[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](N2C=NC(C(=O)N([Si](C)(C)C)[Si](C)(C)C)=N2)[C@@H]1O[Si](C)(C)C	2451.6	Semi standard non polar	33892256
Ribavirin,4TMS,isomer #4	C[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](N2C=NC(C(=O)N([Si](C)(C)C)[Si](C)(C)C)=N2)[C@@H]1O[Si](C)(C)C	2511.5	Standard non polar	33892256
Ribavirin,4TMS,isomer #4	C[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](N2C=NC(C(=O)N([Si](C)(C)C)[Si](C)(C)C)=N2)[C@@H]1O[Si](C)(C)C	3159.8	Standard polar	33892256
Ribavirin,5TMS,isomer #1	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC(C(=O)N([Si](C)(C)C)[Si](C)(C)C)=N2)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	2492.9	Semi standard non polar	33892256
Ribavirin,5TMS,isomer #1	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC(C(=O)N([Si](C)(C)C)[Si](C)(C)C)=N2)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	2487.5	Standard non polar	33892256
Ribavirin,5TMS,isomer #1	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC(C(=O)N([Si](C)(C)C)[Si](C)(C)C)=N2)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	2988.5	Standard polar	33892256
Ribavirin,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC(C(N)=O)=N2)[C@H](O)[C@@H]1O	2695.5	Semi standard non polar	33892256
Ribavirin,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](N2C=NC(C(N)=O)=N2)[C@@H]1O	2657.3	Semi standard non polar	33892256
Ribavirin,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C=NC(C(N)=O)=N1	2674.6	Semi standard non polar	33892256
Ribavirin,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NC(=O)C1=NN([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)C=N1	2680.6	Semi standard non polar	33892256
Ribavirin,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC(C(N)=O)=N2)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O	2884.4	Semi standard non polar	33892256
Ribavirin,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC(C(N)=O)=N2)[C@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C	2872.7	Semi standard non polar	33892256
Ribavirin,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC(=O)C1=NN([C@@H]2O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H]2O)C=N1	2912.0	Semi standard non polar	33892256
Ribavirin,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](N2C=NC(C(N)=O)=N2)[C@@H]1O[Si](C)(C)C(C)(C)C	2829.5	Semi standard non polar	33892256
Ribavirin,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)NC(=O)C1=NN([C@@H]2O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O)C=N1	2895.9	Semi standard non polar	33892256
Ribavirin,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)NC(=O)C1=NN([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O[Si](C)(C)C(C)(C)C)C=N1	2886.8	Semi standard non polar	33892256
Ribavirin,2TBDMS,isomer #7	CC(C)(C)[Si](C)(C)N(C(=O)C1=NN([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)C=N1)[Si](C)(C)C(C)(C)C	2946.2	Semi standard non polar	33892256
Ribavirin,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC(C(N)=O)=N2)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C	3025.6	Semi standard non polar	33892256
Ribavirin,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC(=O)C1=NN([C@@H]2O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H]2O[Si](C)(C)C(C)(C)C)C=N1	3106.2	Semi standard non polar	33892256
Ribavirin,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC(=O)C1=NN([C@@H]2O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O)C=N1	3104.2	Semi standard non polar	33892256
Ribavirin,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=N2)[C@H](O)[C@@H]1O	3114.1	Semi standard non polar	33892256
Ribavirin,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)NC(=O)C1=NN([C@@H]2O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O[Si](C)(C)C(C)(C)C)C=N1	3075.3	Semi standard non polar	33892256
Ribavirin,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](N2C=NC(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=N2)[C@@H]1O	3108.8	Semi standard non polar	33892256
Ribavirin,3TBDMS,isomer #7	CC(C)(C)[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C=NC(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=N1	3107.3	Semi standard non polar	33892256
Ribavirin,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=O)C1=NN([C@@H]2O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O[Si](C)(C)C(C)(C)C)C=N1	3260.4	Semi standard non polar	33892256
Ribavirin,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=O)C1=NN([C@@H]2O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O[Si](C)(C)C(C)(C)C)C=N1	3107.1	Standard non polar	33892256
Ribavirin,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=O)C1=NN([C@@H]2O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O[Si](C)(C)C(C)(C)C)C=N1	3839.6	Standard polar	33892256
Ribavirin,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=N2)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O	3280.6	Semi standard non polar	33892256
Ribavirin,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=N2)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O	3247.9	Standard non polar	33892256
Ribavirin,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=N2)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O	3461.0	Standard polar	33892256
Ribavirin,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=N2)[C@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C	3273.3	Semi standard non polar	33892256
Ribavirin,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=N2)[C@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C	3238.2	Standard non polar	33892256
Ribavirin,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=N2)[C@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C	3416.8	Standard polar	33892256
Ribavirin,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](N2C=NC(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=N2)[C@@H]1O[Si](C)(C)C(C)(C)C	3259.0	Semi standard non polar	33892256
Ribavirin,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](N2C=NC(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=N2)[C@@H]1O[Si](C)(C)C(C)(C)C	3252.5	Standard non polar	33892256
Ribavirin,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](N2C=NC(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=N2)[C@@H]1O[Si](C)(C)C(C)(C)C	3410.2	Standard polar	33892256
Ribavirin,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=N2)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C	3407.2	Semi standard non polar	33892256
Ribavirin,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=N2)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C	3352.9	Standard non polar	33892256
Ribavirin,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=N2)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C	3356.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Ribavirin GC-MS (Non-derivatized) - 70eV, Positive	splash10-08nc-9320000000-385cc2e08cf140e0ecee	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ribavirin GC-MS (3 TMS) - 70eV, Positive	splash10-0zpj-6922200000-75bb1d484addd27068ee	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ribavirin 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 - Ribavirin LC-ESI-QFT , negative-QTOF	splash10-03di-0900000000-92e2bd11ded2c95f3fbd	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ribavirin LC-ESI-QFT , negative-QTOF	splash10-03di-0900000000-109ebb69f722bb3a92d7	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ribavirin LC-ESI-QFT , negative-QTOF	splash10-03di-2900000000-c0d63d0633c304d466ca	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ribavirin LC-ESI-QFT , negative-QTOF	splash10-03xr-5900000000-c6f13aea6e263f2557f4	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ribavirin LC-ESI-QFT , negative-QTOF	splash10-02t9-9500000000-cefa4afc53cf92b724c3	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ribavirin LC-ESI-QFT , negative-QTOF	splash10-014i-9200000000-3a87882b304f3a9c9995	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ribavirin LC-ESI-QFT , positive-QTOF	splash10-03di-0900000000-d5e98a470d0e674937d2	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ribavirin LC-ESI-QFT , positive-QTOF	splash10-03di-0900000000-c659efd26af31b3b98dc	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ribavirin LC-ESI-QFT , positive-QTOF	splash10-03di-1900000000-56c00c62af197ae8eecb	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ribavirin LC-ESI-QFT , positive-QTOF	splash10-03di-2900000000-aa387f940aedc4b69874	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ribavirin LC-ESI-QFT , positive-QTOF	splash10-03di-3900000000-795b88d3d651082dccb4	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ribavirin 75V, Negative-QTOF	splash10-02t9-9500000000-2ad23cf2e8f500d101cc	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ribavirin 40V, Negative-QTOF	splash10-014l-9000000000-6a9ceaf94e48a5856e63	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ribavirin 10V, Negative-QTOF	splash10-03di-0900000000-18802a19d16454483630	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ribavirin 90V, Negative-QTOF	splash10-014i-9200000000-f26697f5224329016008	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ribavirin 20V, Negative-QTOF	splash10-03di-3900000000-03e82b27fd25878e95dc	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ribavirin 10V, Negative-QTOF	splash10-03di-0900000000-85ef00069e1dea09445a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ribavirin 20V, Negative-QTOF	splash10-03di-3900000000-ec554c2067df2f7a90a5	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ribavirin 40V, Negative-QTOF	splash10-014l-9000000000-ab534ce4a5c6314c7208	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ribavirin 10V, Positive-QTOF	splash10-03dj-1960000000-8e1936b4490afdea1b45	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ribavirin 20V, Positive-QTOF	splash10-03di-3900000000-34acc3537097bf33c4ec	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ribavirin 40V, Positive-QTOF	splash10-01ot-9400000000-9e7ebf6d4e248ffbf3bb	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ribavirin 10V, Negative-QTOF	splash10-03di-2900000000-1aad1437a8d8217dea0e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ribavirin 20V, Negative-QTOF	splash10-03di-3900000000-0e379b4cf22b87e29955	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ribavirin 40V, Negative-QTOF	splash10-0006-9100000000-0c0a02c5d745eb2131d7	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

Cytoplasm
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00811	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00811	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00811

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

34439

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Ribavirin

METLIN ID

Not Available

PubChem Compound

37542

PDB ID

Not Available

ChEBI ID

63580

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

Sidwell RW, Huffman JH, Khare GP, Allen LB, Witkowski JT, Robins RK: Broad-spectrum antiviral activity of Virazole: 1-beta-D-ribofuranosyl-1,2,4-triazole-3-carboxamide. Science. 1972 Aug 25;177(4050):705-6. [PubMed:4340949 ]
Sidwell RW, Bailey KW, Wong MH, Barnard DL, Smee DF: In vitro and in vivo influenza virus-inhibitory effects of viramidine. Antiviral Res. 2005 Oct;68(1):10-7. [PubMed:16087250 ]
Bani-Sadr F, Carrat F, Pol S, Hor R, Rosenthal E, Goujard C, Morand P, Lunel-Fabiani F, Salmon-Ceron D, Piroth L, Pialoux G, Bentata M, Cacoub P, Perronne C: Risk factors for symptomatic mitochondrial toxicity in HIV/hepatitis C virus-coinfected patients during interferon plus ribavirin-based therapy. J Acquir Immune Defic Syndr. 2005 Sep 1;40(1):47-52. [PubMed:16123681 ]
Alvarez D, Dieterich DT, Brau N, Moorehead L, Ball L, Sulkowski MS: Zidovudine use but not weight-based ribavirin dosing impacts anaemia during HCV treatment in HIV-infected persons. J Viral Hepat. 2006 Oct;13(10):683-9. [PubMed:16970600 ]

Enzymes

Enzyme Details

1. Ectonucleotide pyrophosphatase/phosphodiesterase family member 1

General function:: Involved in catalytic activity
Specific function:: Involved primarily in ATP hydrolysis at the plasma membrane. Plays a role in regulating pyrophosphate levels, and functions in bone mineralization and soft tissue calcification. In vitro, has a broad specificity, hydrolyzing other nucleoside 5' triphosphates such as GTP, CTP, TTP and UTP to their corresponding monophosphates with release of pyrophosphate and diadenosine polyphosphates, and also 3',5'-cAMP to AMP. May also be involved in the regulation of the availability of nucleotide sugars in the endoplasmic reticulum and Golgi, and the regulation of purinergic signaling. Appears to modulate insulin sensitivity.
Gene Name:: ENPP1
Uniprot ID:: P22413
Molecular weight:: 104923.58

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 ]

Enzyme Details

2. Adenosine kinase

General function:: Involved in adenosine kinase activity
Specific function:: ATP dependent phosphorylation of adenosine and other related nucleoside analogs to monophosphate derivatives. Serves as a potential regulator of concentrations of extracellular adenosine and intracellular adenine nucleotides.
Gene Name:: ADK
Uniprot ID:: P55263
Molecular weight:: 38702.93

References

Wu JZ, Larson G, Walker H, Shim JH, Hong Z: Phosphorylation of ribavirin and viramidine by adenosine kinase and cytosolic 5'-nucleotidase II: Implications for ribavirin metabolism in erythrocytes. Antimicrob Agents Chemother. 2005 Jun;49(6):2164-71. [PubMed:15917509 ]
Kumarapperuma SC, Sun Y, Jeselnik M, Chung K, Parker WB, Jonsson CB, Arterburn JB: Structural effects on the phosphorylation of 3-substituted 1-beta-D-ribofuranosyl-1,2,4-triazoles by human adenosine kinase. Bioorg Med Chem Lett. 2007 Jun 1;17(11):3203-7. Epub 2007 Mar 12. [PubMed:17379518 ]

Enzyme Details

3. Inosine-5'-monophosphate dehydrogenase 1

General function:: Involved in catalytic activity
Specific function:: Catalyzes the conversion of inosine 5'-phosphate (IMP) to xanthosine 5'-phosphate (XMP), the first committed and rate-limiting step in the de novo synthesis of guanine nucleotides, and therefore plays an important role in the regulation of cell growth. Could also have a single-stranded nucleic acid-binding activity and could play a role in RNA and/or DNA metabolism. It may also have a role in the development of malignancy and the growth progression of some tumors.
Gene Name:: IMPDH1
Uniprot ID:: P20839
Molecular weight:: 63252.24

References

Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Gish RG: Treating HCV with ribavirin analogues and ribavirin-like molecules. J Antimicrob Chemother. 2006 Jan;57(1):8-13. Epub 2005 Nov 17. [PubMed:16293677 ]
McHutchison JG, Shiffman ML, Cheung RC, Gordon SC, Wright TL, Pottage JC Jr, McNair L, Ette E, Moseley S, Alam J: A randomized, double-blind, placebo-controlled dose-escalation trial of merimepodib (VX-497) and interferon-alpha in previously untreated patients with chronic hepatitis C. Antivir Ther. 2005;10(5):635-43. [PubMed:16152757 ]
Leyssen P, De Clercq E, Neyts J: The anti-yellow fever virus activity of ribavirin is independent of error-prone replication. Mol Pharmacol. 2006 Apr;69(4):1461-7. Epub 2006 Jan 18. [PubMed:16421290 ]

Enzyme Details

4. Cytosolic purine 5'-nucleotidase

General function:: Involved in 5'-nucleotidase activity
Specific function:: May have a critical role in the maintenance of a constant composition of intracellular purine/pyrimidine nucleotides in cooperation with other nucleotidases. Preferentially hydrolyzes inosine 5'-monophosphate (IMP) and other purine nucleotides.
Gene Name:: NT5C2
Uniprot ID:: P49902
Molecular weight:: 64969.2

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. Equilibrative nucleoside transporter 1

General function:: Involved in nucleoside transmembrane transporter activity
Specific function:: Mediates both influx and efflux of nucleosides across the membrane (equilibrative transporter). It is sensitive (ES) to low concentrations of the inhibitor nitrobenzylmercaptopurine riboside (NBMPR) and is sodium-independent. It has a higher affinity for adenosine. Inhibited by dipyridamole and dilazep (anticancer chemotherapeutics drugs)
Gene Name:: SLC29A1
Uniprot ID:: Q99808
Molecular weight:: 50218.8

References

Yamamoto T, Sugawara M, Kikukawa T, Miyauchi S, Yamaguchi M, Tero A, Takagi S, Nakagaki T: Kinetic study of anti-viral ribavirin uptake mediated by hCNT3 and hENT1 in Xenopus laevis oocytes. Biophys Chem. 2010 Mar;147(1-2):59-65. doi: 10.1016/j.bpc.2009.12.012. Epub 2010 Jan 6. [PubMed:20096989 ]
Fukuchi Y, Furihata T, Hashizume M, Iikura M, Chiba K: Characterization of ribavirin uptake systems in human hepatocytes. J Hepatol. 2010 Apr;52(4):486-92. doi: 10.1016/j.jhep.2010.01.011. Epub 2010 Feb 4. [PubMed:20185188 ]

Enzyme Details

2. Solute carrier family 28 member 3

General function:: Involved in nucleoside:sodium symporter activity
Specific function:: Sodium-dependent, pyrimidine- and purine-selective. Involved in the homeostasis of endogenous nucleosides. Exhibits the transport characteristics of the nucleoside transport system cib or N3 subtype (N3/cib) (with marked transport of both thymidine and inosine). Employs a 2:1 sodium/nucleoside ratio. Also able to transport gemcitabine, 3'-azido-3'-deoxythymidine (AZT), ribavirin and 3-deazauridine
Gene Name:: SLC28A3
Uniprot ID:: Q9HAS3
Molecular weight:: 76929.6

References

Yamamoto T, Sugawara M, Kikukawa T, Miyauchi S, Yamaguchi M, Tero A, Takagi S, Nakagaki T: Kinetic study of anti-viral ribavirin uptake mediated by hCNT3 and hENT1 in Xenopus laevis oocytes. Biophys Chem. 2010 Mar;147(1-2):59-65. doi: 10.1016/j.bpc.2009.12.012. Epub 2010 Jan 6. [PubMed:20096989 ]

Showing metabocard for Ribavirin (HMDB0014949)

MOL for HMDB0014949 (Ribavirin)

3D MOL for HMDB0014949 (Ribavirin)

3D SDF for HMDB0014949 (Ribavirin)

3D-SDF for HMDB0014949 (Ribavirin)

PDB for HMDB0014949 (Ribavirin)

3D PDB for HMDB0014949 (Ribavirin)

SMILES for HMDB0014949 (Ribavirin)

INCHI for HMDB0014949 (Ribavirin)

Structure for HMDB0014949 (Ribavirin)

3D Structure for HMDB0014949 (Ribavirin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

References

References

References

References

Transporters

References

References