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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-10-30 10:32:48 UTC

Update Date

2022-03-07 03:17:33 UTC

HMDB ID

HMDB0059609

Secondary Accession Numbers

HMDB59609

Metabolite Identification

Common Name

albendazole S-oxide

Description

albendazole S-oxide, also known as ricobendazole, belongs to the class of organic compounds known as benzimidazoles. These are organic compounds containing a benzene ring fused to an imidazole ring (five member ring containing a nitrogen atom, 4 carbon atoms, and two double bonds). Albendazole s-oxide is part of the Steroid hormone biosynthesis, Linoleic acid metabolism, Retinol metabolism, and Bile secretion pathways. albendazole S-oxide is a moderately basic compound (based on its pKa).

Structure

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

HMDB0059609
     RDKit          3D
albendazole S-oxide
 34 35  0  0  0  0  0  0  0  0999 V2000
   -6.2734    1.1138    0.6660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4427    0.4228   -0.4107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0505    0.2010    0.1450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0368   -0.6180   -1.1078 S   0  0  0  0  0  4  0  0  0  0  0  0
   -3.0429    0.1435   -2.4044 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4081   -0.8837   -0.4734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0968   -2.0403    0.1949 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1856   -2.2621    0.7005 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1440   -1.2856    0.5133 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4383   -1.1861    0.8637 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9764   -0.0233    0.4545 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3169    0.4395    0.6393 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2888   -0.2136    0.1194 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0501   -1.3583   -0.6161 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5815    0.2206    0.2897 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8913    1.5342    0.6378 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9784    0.6356   -0.1796 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8579   -0.1018   -0.1607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4174    0.0710   -0.6399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2578    1.4067    0.2056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7482    1.9902    1.0548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5332    0.3611    1.4500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3570    1.0599   -1.3037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9178   -0.5316   -0.6605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6012    1.1215    0.5207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1581   -0.4915    1.0121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8504   -2.8111    0.3436 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4760   -3.1523    1.2306 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4850   -2.0999   -0.2346 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4503    1.8495    1.6152 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0061    1.6304    0.7065 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5739    2.2849   -0.1062 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1250    1.5790   -0.6011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6331    0.9940   -1.1632 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  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  3
 13 14  1  0
 13 15  1  0
 15 16  1  0
 11 17  1  0
 17 18  1  0
 18 19  2  0
 19  6  1  0
 18  9  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  2 24  1  0
  3 25  1  0
  3 26  1  0
  7 27  1  0
  8 28  1  0
 14 29  1  0
 16 30  1  0
 16 31  1  0
 16 32  1  0
 17 33  1  0
 19 34  1  0
M  END

  Mrv0541 10301209482D          

 19 20  0  0  0  0            999 V2000
    6.8513    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1801    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1368   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0574    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4699    0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4699    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7676    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -0.4125    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  5  4  2  0  0  0  0
  6  3  1  0  0  0  0
  8  4  1  0  0  0  0
  8  7  2  0  0  0  0
  9  5  1  0  0  0  0
 10  7  1  0  0  0  0
 10  9  2  0  0  0  0
 13  9  1  0  0  0  0
 13 11  2  0  0  0  0
 14 10  1  0  0  0  0
 14 11  1  0  0  0  0
 15 11  1  4  0  0  0
 15 12  2  0  0  0  0
 16 12  1  0  0  0  0
 18  2  1  0  0  0  0
 18 12  1  0  0  0  0
 19  6  1  0  0  0  0
 19  8  1  0  0  0  0
 19 17  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0059609

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCS(=O)C1=CC2=C(C=C1)N=C(N2)N=C(O)OC

> <INCHI_IDENTIFIER>
InChI=1S/C12H15N3O3S/c1-3-6-19(17)8-4-5-9-10(7-8)14-11(13-9)15-12(16)18-2/h4-5,7H,3,6H2,1-2H3,(H2,13,14,15,16)

> <INCHI_KEY>
VXTGHWHFYNYFFV-UHFFFAOYSA-N

> <FORMULA>
C12H15N3O3S

> <MOLECULAR_WEIGHT>
281.331

> <EXACT_MASS>
281.083412051

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
29.328678008308707

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-[6-(propane-1-sulfinyl)-1H-1,3-benzodiazol-2-yl]methoxycarboximidic acid

> <ALOGPS_LOGP>
1.17

> <JCHEM_LOGP>
2.2600797166666666

> <ALOGPS_LOGS>
-1.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.165410040377317

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.068601935393441

> <JCHEM_PKA_STRONGEST_BASIC>
1.9895938164835107

> <JCHEM_POLAR_SURFACE_AREA>
87.57000000000001

> <JCHEM_REFRACTIVITY>
75.5588

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.45e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-[5-(propane-1-sulfinyl)-3H-1,3-benzodiazol-2-yl]methoxycarboximidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0059609
     RDKit          3D
albendazole S-oxide
 34 35  0  0  0  0  0  0  0  0999 V2000
   -6.2734    1.1138    0.6660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4427    0.4228   -0.4107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0505    0.2010    0.1450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0368   -0.6180   -1.1078 S   0  0  0  0  0  4  0  0  0  0  0  0
   -3.0429    0.1435   -2.4044 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4081   -0.8837   -0.4734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0968   -2.0403    0.1949 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1856   -2.2621    0.7005 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1440   -1.2856    0.5133 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4383   -1.1861    0.8637 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9764   -0.0233    0.4545 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3169    0.4395    0.6393 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2888   -0.2136    0.1194 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0501   -1.3583   -0.6161 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5815    0.2206    0.2897 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8913    1.5342    0.6378 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9784    0.6356   -0.1796 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8579   -0.1018   -0.1607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4174    0.0710   -0.6399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2578    1.4067    0.2056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7482    1.9902    1.0548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5332    0.3611    1.4500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3570    1.0599   -1.3037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9178   -0.5316   -0.6605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6012    1.1215    0.5207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1581   -0.4915    1.0121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8504   -2.8111    0.3436 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4760   -3.1523    1.2306 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4850   -2.0999   -0.2346 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4503    1.8495    1.6152 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0061    1.6304    0.7065 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5739    2.2849   -0.1062 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1250    1.5790   -0.6011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6331    0.9940   -1.1632 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  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  3
 13 14  1  0
 13 15  1  0
 15 16  1  0
 11 17  1  0
 17 18  1  0
 18 19  2  0
 19  6  1  0
 18  9  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  2 24  1  0
  3 25  1  0
  3 26  1  0
  7 27  1  0
  8 28  1  0
 14 29  1  0
 16 30  1  0
 16 31  1  0
 16 32  1  0
 17 33  1  0
 19 34  1  0
M  END

HEADER    PROTEIN                                 30-OCT-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-OCT-12         0                                  
HETATM    1  C   UNK     0      12.789   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.203   0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.455  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.122   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.454   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.107   2.104   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       3.322   2.016   0.000  0.00  0.00           N+0
HETATM   14  N   UNK     0       3.322  -0.476   0.000  0.00  0.00           N+0
HETATM   15  N   UNK     0       0.877   0.770   0.000  0.00  0.00           N+0
HETATM   16  O   UNK     0       0.877   3.437   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       8.788  -2.310   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -1.433   2.104   0.000  0.00  0.00           O+0
HETATM   19  S   UNK     0       8.788  -0.770   0.000  0.00  0.00           S+0
CONECT    1    3                                                            
CONECT    2   18                                                            
CONECT    3    1    6                                                       
CONECT    4    5    8                                                       
CONECT    5    4    9                                                       
CONECT    6    3   19                                                       
CONECT    7    8   10                                                       
CONECT    8    4    7   19                                                  
CONECT    9    5   10   13                                                  
CONECT   10    7    9   14                                                  
CONECT   11   13   14   15                                                  
CONECT   12   15   16   18                                                  
CONECT   13    9   11                                                       
CONECT   14   10   11                                                       
CONECT   15   11   12                                                       
CONECT   16   12                                                            
CONECT   17   19                                                            
CONECT   18    2   12                                                       
CONECT   19    6    8   17                                                  
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

COMPND    HMDB0059609
HETATM    1  C1  UNL     1      -6.273   1.114   0.666  1.00  0.00           C  
HETATM    2  C2  UNL     1      -5.443   0.423  -0.411  1.00  0.00           C  
HETATM    3  C3  UNL     1      -4.051   0.201   0.145  1.00  0.00           C  
HETATM    4  S1  UNL     1      -3.037  -0.618  -1.108  1.00  0.00           S  
HETATM    5  O1  UNL     1      -3.043   0.144  -2.404  1.00  0.00           O  
HETATM    6  C4  UNL     1      -1.408  -0.884  -0.473  1.00  0.00           C  
HETATM    7  C5  UNL     1      -1.097  -2.040   0.195  1.00  0.00           C  
HETATM    8  C6  UNL     1       0.186  -2.262   0.700  1.00  0.00           C  
HETATM    9  C7  UNL     1       1.144  -1.286   0.513  1.00  0.00           C  
HETATM   10  N1  UNL     1       2.438  -1.186   0.864  1.00  0.00           N  
HETATM   11  C8  UNL     1       2.976  -0.023   0.454  1.00  0.00           C  
HETATM   12  N2  UNL     1       4.317   0.440   0.639  1.00  0.00           N  
HETATM   13  C9  UNL     1       5.289  -0.214   0.119  1.00  0.00           C  
HETATM   14  O2  UNL     1       5.050  -1.358  -0.616  1.00  0.00           O  
HETATM   15  O3  UNL     1       6.582   0.221   0.290  1.00  0.00           O  
HETATM   16  C10 UNL     1       6.891   1.534   0.638  1.00  0.00           C  
HETATM   17  N3  UNL     1       1.978   0.636  -0.180  1.00  0.00           N  
HETATM   18  C11 UNL     1       0.858  -0.102  -0.161  1.00  0.00           C  
HETATM   19  C12 UNL     1      -0.417   0.071  -0.640  1.00  0.00           C  
HETATM   20  H1  UNL     1      -7.258   1.407   0.206  1.00  0.00           H  
HETATM   21  H2  UNL     1      -5.748   1.990   1.055  1.00  0.00           H  
HETATM   22  H3  UNL     1      -6.533   0.361   1.450  1.00  0.00           H  
HETATM   23  H4  UNL     1      -5.357   1.060  -1.304  1.00  0.00           H  
HETATM   24  H5  UNL     1      -5.918  -0.532  -0.660  1.00  0.00           H  
HETATM   25  H6  UNL     1      -3.601   1.122   0.521  1.00  0.00           H  
HETATM   26  H7  UNL     1      -4.158  -0.492   1.012  1.00  0.00           H  
HETATM   27  H8  UNL     1      -1.850  -2.811   0.344  1.00  0.00           H  
HETATM   28  H9  UNL     1       0.476  -3.152   1.231  1.00  0.00           H  
HETATM   29  H10 UNL     1       4.485  -2.100  -0.235  1.00  0.00           H  
HETATM   30  H11 UNL     1       6.450   1.849   1.615  1.00  0.00           H  
HETATM   31  H12 UNL     1       8.006   1.630   0.706  1.00  0.00           H  
HETATM   32  H13 UNL     1       6.574   2.285  -0.106  1.00  0.00           H  
HETATM   33  H14 UNL     1       2.125   1.579  -0.601  1.00  0.00           H  
HETATM   34  H15 UNL     1      -0.633   0.994  -1.163  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3   23   24
CONECT    3    4   25   26
CONECT    4    5    5    6
CONECT    6    7    7   19
CONECT    7    8   27
CONECT    8    9    9   28
CONECT    9   10   18
CONECT   10   11   11
CONECT   11   12   17
CONECT   12   13   13
CONECT   13   14   15
CONECT   14   29
CONECT   15   16
CONECT   16   30   31   32
CONECT   17   18   33
CONECT   18   19   19
CONECT   19   34
END

HMDB0059609
     RDKit          3D
albendazole S-oxide
 34 35  0  0  0  0  0  0  0  0999 V2000
   -6.2734    1.1138    0.6660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4427    0.4228   -0.4107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0505    0.2010    0.1450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0368   -0.6180   -1.1078 S   0  0  0  0  0  4  0  0  0  0  0  0
   -3.0429    0.1435   -2.4044 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4081   -0.8837   -0.4734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0968   -2.0403    0.1949 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1856   -2.2621    0.7005 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1440   -1.2856    0.5133 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4383   -1.1861    0.8637 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9764   -0.0233    0.4545 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3169    0.4395    0.6393 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2888   -0.2136    0.1194 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0501   -1.3583   -0.6161 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5815    0.2206    0.2897 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8913    1.5342    0.6378 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9784    0.6356   -0.1796 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8579   -0.1018   -0.1607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4174    0.0710   -0.6399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2578    1.4067    0.2056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7482    1.9902    1.0548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5332    0.3611    1.4500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3570    1.0599   -1.3037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9178   -0.5316   -0.6605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6012    1.1215    0.5207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1581   -0.4915    1.0121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8504   -2.8111    0.3436 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4760   -3.1523    1.2306 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4850   -2.0999   -0.2346 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4503    1.8495    1.6152 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0061    1.6304    0.7065 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5739    2.2849   -0.1062 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1250    1.5790   -0.6011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6331    0.9940   -1.1632 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  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  3
 13 14  1  0
 13 15  1  0
 15 16  1  0
 11 17  1  0
 17 18  1  0
 18 19  2  0
 19  6  1  0
 18  9  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  2 24  1  0
  3 25  1  0
  3 26  1  0
  7 27  1  0
  8 28  1  0
 14 29  1  0
 16 30  1  0
 16 31  1  0
 16 32  1  0
 17 33  1  0
 19 34  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(+-)-Albendazole sulfoxide	ChEBI
Albendazole oxide	ChEBI
Albendazole sulfoxide	ChEBI
Ricobendazole	ChEBI
Rycobendazole	ChEBI
(+-)-Albendazole sulphoxide	Generator
Albendazole sulphoxide	Generator
Albendazole sulfoxide, monohydrochloride	HMDB

Chemical Formula

C₁₂H₁₅N₃O₃S

Average Molecular Weight

281.331

Monoisotopic Molecular Weight

281.083412051

IUPAC Name

N-[6-(propane-1-sulfinyl)-1H-1,3-benzodiazol-2-yl]methoxycarboximidic acid

Traditional Name

N-[5-(propane-1-sulfinyl)-3H-1,3-benzodiazol-2-yl]methoxycarboximidic acid

CAS Registry Number

Not Available

SMILES

CCCS(=O)C1=CC2=C(C=C1)N=C(N2)N=C(O)OC

InChI Identifier

InChI=1S/C12H15N3O3S/c1-3-6-19(17)8-4-5-9-10(7-8)14-11(13-9)15-12(16)18-2/h4-5,7H,3,6H2,1-2H3,(H2,13,14,15,16)

InChI Key

VXTGHWHFYNYFFV-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzimidazoles. These are organic compounds containing a benzene ring fused to an imidazole ring (five member ring containing a nitrogen atom, 4 carbon atoms, and two double bonds).

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzimidazoles

Sub Class

Not Available

Direct Parent

Benzimidazoles

Alternative Parents

Substituents

Benzimidazole
Benzenoid
Azole
Imidazole
Heteroaromatic compound
Sulfoxide
Carboximidic acid derivative
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Sulfinyl compound
Organic nitrogen compound
Hydrocarbon derivative
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

sulfoxide (CHEBI:16959 )
a small molecule (ALBENDAZOLE-S-OXIDE )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0059609)

Source

Exogenous

Exogenous (HMDB: HMDB0059609)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	4.45 g/L	ALOGPS
logP	1.17	ALOGPS
logP	2.26	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	7.07	ChemAxon
pKa (Strongest Basic)	1.99	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	87.57 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	75.56 m³·mol⁻¹	ChemAxon
Polarizability	29.33 Å³	ChemAxon
Number of Rings	2	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]+	166.897	31661259
DarkChem	[M-H]-	166.107	31661259
DeepCCS	[M+H]+	171.16	30932474
DeepCCS	[M-H]-	168.802	30932474
DeepCCS	[M-2H]-	201.688	30932474
DeepCCS	[M+Na]+	177.253	30932474
AllCCS	[M+H]+	163.3	32859911
AllCCS	[M+H-H2O]+	160.0	32859911
AllCCS	[M+NH4]+	166.3	32859911
AllCCS	[M+Na]+	167.1	32859911
AllCCS	[M-H]-	163.6	32859911
AllCCS	[M+Na-2H]-	163.7	32859911
AllCCS	[M+HCOO]-	164.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
albendazole S-oxide	CCCS(=O)C1=CC2=C(C=C1)N=C(N2)N=C(O)OC	3748.7	Standard polar	33892256
albendazole S-oxide	CCCS(=O)C1=CC2=C(C=C1)N=C(N2)N=C(O)OC	2459.7	Standard non polar	33892256
albendazole S-oxide	CCCS(=O)C1=CC2=C(C=C1)N=C(N2)N=C(O)OC	2799.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
albendazole S-oxide,1TMS,isomer #1	CCCS(=O)C1=CC=C2N=C(N=C(OC)O[Si](C)(C)C)[NH]C2=C1	2497.8	Semi standard non polar	33892256
albendazole S-oxide,1TMS,isomer #1	CCCS(=O)C1=CC=C2N=C(N=C(OC)O[Si](C)(C)C)[NH]C2=C1	2497.8	Semi standard non polar	33892256
albendazole S-oxide,1TMS,isomer #2	CCCS(=O)C1=CC=C2N=C(N=C(O)OC)N([Si](C)(C)C)C2=C1	2581.0	Semi standard non polar	33892256
albendazole S-oxide,1TMS,isomer #2	CCCS(=O)C1=CC=C2N=C(N=C(O)OC)N([Si](C)(C)C)C2=C1	2581.0	Semi standard non polar	33892256
albendazole S-oxide,2TMS,isomer #1	CCCS(=O)C1=CC=C2N=C(N=C(OC)O[Si](C)(C)C)N([Si](C)(C)C)C2=C1	2534.5	Semi standard non polar	33892256
albendazole S-oxide,2TMS,isomer #1	CCCS(=O)C1=CC=C2N=C(N=C(OC)O[Si](C)(C)C)N([Si](C)(C)C)C2=C1	2762.0	Standard non polar	33892256
albendazole S-oxide,1TBDMS,isomer #1	CCCS(=O)C1=CC=C2N=C(N=C(OC)O[Si](C)(C)C(C)(C)C)[NH]C2=C1	2701.8	Semi standard non polar	33892256
albendazole S-oxide,1TBDMS,isomer #1	CCCS(=O)C1=CC=C2N=C(N=C(OC)O[Si](C)(C)C(C)(C)C)[NH]C2=C1	2701.8	Semi standard non polar	33892256
albendazole S-oxide,1TBDMS,isomer #2	CCCS(=O)C1=CC=C2N=C(N=C(O)OC)N([Si](C)(C)C(C)(C)C)C2=C1	2752.4	Semi standard non polar	33892256
albendazole S-oxide,1TBDMS,isomer #2	CCCS(=O)C1=CC=C2N=C(N=C(O)OC)N([Si](C)(C)C(C)(C)C)C2=C1	2752.4	Semi standard non polar	33892256
albendazole S-oxide,2TBDMS,isomer #1	CCCS(=O)C1=CC=C2N=C(N=C(OC)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C2=C1	2876.2	Semi standard non polar	33892256
albendazole S-oxide,2TBDMS,isomer #1	CCCS(=O)C1=CC=C2N=C(N=C(OC)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C2=C1	3167.7	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - albendazole S-oxide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-7690000000-21e36ddf2465905dc755	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - albendazole S-oxide GC-MS (1 TMS) - 70eV, Positive	splash10-0084-9344000000-708b54c2fe0b2ab0f4d2	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - albendazole S-oxide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - albendazole S-oxide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - albendazole S-oxide 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 - albendazole S-oxide LC-ESI-QTOF , positive-QTOF	splash10-001i-0090000000-4f8faf80d5525c831f61	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - albendazole S-oxide LC-ESI-QTOF , positive-QTOF	splash10-0006-0090000000-e552a43e2f05f7fd3a52	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - albendazole S-oxide LC-ESI-QTOF , positive-QTOF	splash10-0a4i-0390000000-4daf753348e11cbca5d9	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - albendazole S-oxide LC-ESI-QTOF , positive-QTOF	splash10-0a4i-0940000000-be363233970a009f5c67	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - albendazole S-oxide LC-ESI-QTOF , positive-QTOF	splash10-0a4i-0900000000-19ee9c1374c824bdde53	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - albendazole S-oxide 40V, Positive-QTOF	splash10-0a4i-0940000000-d0f2d647b9566b3d5471	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - albendazole S-oxide 30V, Positive-QTOF	splash10-0a4i-0390000000-c5c2b369163baa89e894	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - albendazole S-oxide 10V, Positive-QTOF	splash10-001i-0090000000-c50a14c071083e785b90	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - albendazole S-oxide 50V, Positive-QTOF	splash10-0a4i-0900000000-17ddc6573026b461668c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - albendazole S-oxide 20V, Positive-QTOF	splash10-0006-0090000000-2ddcbc6be8944aa70242	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - albendazole S-oxide 30V, Positive-QTOF	splash10-0a4i-0390000000-0f0e9cf17b08dacc147e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - albendazole S-oxide 40V, Positive-QTOF	splash10-0a4i-0940000000-4a544a55485d72dcc232	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - albendazole S-oxide 50V, Positive-QTOF	splash10-0a4i-0900000000-302cd5c535d552fe5fdc	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - albendazole S-oxide 40V, Positive-QTOF	splash10-0a4i-0940000000-5a13db941efced21b9d7	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - albendazole S-oxide 10V, Positive-QTOF	splash10-00e9-1090000000-e150095a8f96d26a5f0d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - albendazole S-oxide 20V, Positive-QTOF	splash10-00di-2190000000-95bc61e0d527da36378f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - albendazole S-oxide 40V, Positive-QTOF	splash10-0006-9450000000-880977de0008e20d5883	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - albendazole S-oxide 10V, Negative-QTOF	splash10-0532-3090000000-8b0222ac217c5e4b2b61	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - albendazole S-oxide 20V, Negative-QTOF	splash10-0a4i-2190000000-a555b482ba6eed51876f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - albendazole S-oxide 40V, Negative-QTOF	splash10-0a6u-9680000000-b24eefc0024e732c7ed6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - albendazole S-oxide 10V, Positive-QTOF	splash10-001i-0090000000-a179b59f66fecad94272	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - albendazole S-oxide 20V, Positive-QTOF	splash10-0f89-0090000000-4e8a2af4bd5b530c0291	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - albendazole S-oxide 40V, Positive-QTOF	splash10-0ab9-0390000000-5eef2c7c5b772cf0e81b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - albendazole S-oxide 10V, Negative-QTOF	splash10-007k-0090000000-cb9845674928abb020ac	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - albendazole S-oxide 20V, Negative-QTOF	splash10-053s-0390000000-389222650909bec431c3	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB13871

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C02809

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Albendazole

METLIN ID

Not Available

PubChem Compound

83969

PDB ID

Not Available

ChEBI ID

16959

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. Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

Reactions

Albendazole + NADPH + Oxygen → albendazole S-oxide + NADP + Water	details

Showing metabocard for albendazole S-oxide (HMDB0059609)

MOL for HMDB0059609 (albendazole S-oxide)

3D MOL for HMDB0059609 (albendazole S-oxide)

3D SDF for HMDB0059609 (albendazole S-oxide)

3D-SDF for HMDB0059609 (albendazole S-oxide)

PDB for HMDB0059609 (albendazole S-oxide)

3D PDB for HMDB0059609 (albendazole S-oxide)

SMILES for HMDB0059609 (albendazole S-oxide)

INCHI for HMDB0059609 (albendazole S-oxide)

Structure for HMDB0059609 (albendazole S-oxide)

3D Structure for HMDB0059609 (albendazole S-oxide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions