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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 23:49:11 UTC

Update Date

2021-09-26 22:56:06 UTC

HMDB ID

HMDB0246806

Secondary Accession Numbers

None

Metabolite Identification

Common Name

5-Hydroxymebendazole

Description

5-Hydroxymebendazole, also known as compound 86-162, belongs to the class of organic compounds known as 2-benzimidazolylcarbamic acid esters. These are aromatic heteropolycyclic compounds that contain a carbamic acid ester group, which is N-linked to the C2-atom of a benzimidazole moiety. Based on a literature review a small amount of articles have been published on 5-Hydroxymebendazole. This compound has been identified in human blood as reported by (PMID: 31557052 ). 5-hydroxymebendazole is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 5-Hydroxymebendazole is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0246806
     RDKit          3D
5-Hydroxymebendazole
 37 39  0  0  0  0  0  0  0  0999 V2000
    7.5986    1.1540   -0.1161 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6217    0.9193    0.8800 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3390    0.5947    0.4597 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1014    0.5235   -0.7796 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2804    0.3387    1.3706 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9833    0.0099    0.8843 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5982   -0.0987   -0.3999 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2825   -0.4276   -0.4062 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3772   -0.6637   -1.4398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9272   -0.9868   -1.1374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3978   -1.0922    0.1529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8059   -1.4415    0.4236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2046   -2.5183   -0.4032 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7487   -0.3532    0.1937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1074   -0.5940    0.1427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0044    0.4591   -0.0788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5440    1.7455   -0.2481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1690    1.9666   -0.1929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2938    0.9337    0.0240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4884   -0.8552    1.1606 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8385   -0.5262    0.8915 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9031   -0.2527    1.6682 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.6091    1.2719    0.2874 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5770    0.2901   -0.8305 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3074    2.0394   -0.7445 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4981    0.4028    2.3850 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7811   -0.5723   -2.4380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5936   -1.1614   -1.9694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8833   -1.8554    1.4689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7068   -3.3352   -0.2119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5252   -1.5813    0.2684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0461    0.2372   -0.1121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2464    2.5277   -0.4150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8416    2.9861   -0.3296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2302    1.0901    0.0689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7789   -0.9177    2.2197 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8467   -0.2568    2.7150 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  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  2  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 11 20  1  0
 20 21  2  0
 21 22  1  0
 22  6  1  0
 21  8  1  0
 19 14  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  5 26  1  0
  9 27  1  0
 10 28  1  0
 12 29  1  0
 13 30  1  0
 15 31  1  0
 16 32  1  0
 17 33  1  0
 18 34  1  0
 19 35  1  0
 20 36  1  0
 22 37  1  0
M  END

  Mrv1652309112101492D          

 22 24  0  0  0  0            999 V2000
   -3.1034   -2.1269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6909   -1.4124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8659   -1.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4534   -2.1269    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4534   -0.6979    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -1.3654    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -0.0305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9279   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9279   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    0.9521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  6 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  8 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 16 21  1  0  0  0  0
 15 22  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0246806

> <DATABASE_NAME>
hmdb

> <SMILES>
COC(=O)NC1=NC2=C(N1)C=C(C=C2)C(O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H15N3O3/c1-22-16(21)19-15-17-12-8-7-11(9-13(12)18-15)14(20)10-5-3-2-4-6-10/h2-9,14,20H,1H3,(H2,17,18,19,21)

> <INCHI_KEY>
IIQKUGXEGMZCLE-UHFFFAOYSA-N

> <FORMULA>
C16H15N3O3

> <MOLECULAR_WEIGHT>
297.314

> <EXACT_MASS>
297.111341355

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
31.399083683492055

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl N-{6-[hydroxy(phenyl)methyl]-1H-1,3-benzodiazol-2-yl}carbamate

> <ALOGPS_LOGP>
2.59

> <JCHEM_LOGP>
2.8176459273333325

> <ALOGPS_LOGS>
-3.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.503545544789247

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.567347160434606

> <JCHEM_PKA_STRONGEST_BASIC>
4.251454512264446

> <JCHEM_POLAR_SURFACE_AREA>
87.24

> <JCHEM_REFRACTIVITY>
82.02710000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.28e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl N-{5-[hydroxy(phenyl)methyl]-3H-1,3-benzodiazol-2-yl}carbamate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0246806
     RDKit          3D
5-Hydroxymebendazole
 37 39  0  0  0  0  0  0  0  0999 V2000
    7.5986    1.1540   -0.1161 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6217    0.9193    0.8800 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3390    0.5947    0.4597 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1014    0.5235   -0.7796 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2804    0.3387    1.3706 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9833    0.0099    0.8843 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5982   -0.0987   -0.3999 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2825   -0.4276   -0.4062 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3772   -0.6637   -1.4398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9272   -0.9868   -1.1374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3978   -1.0922    0.1529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8059   -1.4415    0.4236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2046   -2.5183   -0.4032 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7487   -0.3532    0.1937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1074   -0.5940    0.1427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0044    0.4591   -0.0788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5440    1.7455   -0.2481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1690    1.9666   -0.1929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2938    0.9337    0.0240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4884   -0.8552    1.1606 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8385   -0.5262    0.8915 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9031   -0.2527    1.6682 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.6091    1.2719    0.2874 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5770    0.2901   -0.8305 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3074    2.0394   -0.7445 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4981    0.4028    2.3850 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7811   -0.5723   -2.4380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5936   -1.1614   -1.9694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8833   -1.8554    1.4689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7068   -3.3352   -0.2119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5252   -1.5813    0.2684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0461    0.2372   -0.1121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2464    2.5277   -0.4150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8416    2.9861   -0.3296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2302    1.0901    0.0689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7789   -0.9177    2.2197 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8467   -0.2568    2.7150 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  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  2  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 11 20  1  0
 20 21  2  0
 21 22  1  0
 22  6  1  0
 21  8  1  0
 19 14  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  5 26  1  0
  9 27  1  0
 10 28  1  0
 12 29  1  0
 13 30  1  0
 15 31  1  0
 16 32  1  0
 17 33  1  0
 18 34  1  0
 19 35  1  0
 20 36  1  0
 22 37  1  0
M  END

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0      -5.793  -3.970   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -5.023  -2.637   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -3.483  -2.637   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -2.713  -3.970   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0      -2.713  -1.303   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      -1.173  -1.303   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      -0.268  -2.549   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       1.197  -2.073   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.197  -0.533   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0      -0.268  -0.057   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       2.530   0.237   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.864  -0.533   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.864  -2.073   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.530  -2.843   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.198   0.237   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.531  -0.533   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.865   0.237   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.199  -0.533   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.199  -2.073   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.865  -2.843   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.531  -2.073   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       5.198   1.777   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   10                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   14                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9    6                                                       
CONECT   11    9   12                                                       
CONECT   12   11   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13    8                                                       
CONECT   15   12   16   22                                                  
CONECT   16   15   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   16                                                       
CONECT   22   15                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

COMPND    HMDB0246806
HETATM    1  C1  UNL     1       7.599   1.154  -0.116  1.00  0.00           C  
HETATM    2  O1  UNL     1       6.622   0.919   0.880  1.00  0.00           O  
HETATM    3  C2  UNL     1       5.339   0.595   0.460  1.00  0.00           C  
HETATM    4  O2  UNL     1       5.101   0.523  -0.780  1.00  0.00           O  
HETATM    5  N1  UNL     1       4.280   0.339   1.371  1.00  0.00           N  
HETATM    6  C3  UNL     1       2.983   0.010   0.884  1.00  0.00           C  
HETATM    7  N2  UNL     1       2.598  -0.099  -0.400  1.00  0.00           N  
HETATM    8  C4  UNL     1       1.283  -0.428  -0.406  1.00  0.00           C  
HETATM    9  C5  UNL     1       0.377  -0.664  -1.440  1.00  0.00           C  
HETATM   10  C6  UNL     1      -0.927  -0.987  -1.137  1.00  0.00           C  
HETATM   11  C7  UNL     1      -1.398  -1.092   0.153  1.00  0.00           C  
HETATM   12  C8  UNL     1      -2.806  -1.441   0.424  1.00  0.00           C  
HETATM   13  O3  UNL     1      -3.205  -2.518  -0.403  1.00  0.00           O  
HETATM   14  C9  UNL     1      -3.749  -0.353   0.194  1.00  0.00           C  
HETATM   15  C10 UNL     1      -5.107  -0.594   0.143  1.00  0.00           C  
HETATM   16  C11 UNL     1      -6.004   0.459  -0.079  1.00  0.00           C  
HETATM   17  C12 UNL     1      -5.544   1.746  -0.248  1.00  0.00           C  
HETATM   18  C13 UNL     1      -4.169   1.967  -0.193  1.00  0.00           C  
HETATM   19  C14 UNL     1      -3.294   0.934   0.024  1.00  0.00           C  
HETATM   20  C15 UNL     1      -0.488  -0.855   1.161  1.00  0.00           C  
HETATM   21  C16 UNL     1       0.839  -0.526   0.891  1.00  0.00           C  
HETATM   22  N3  UNL     1       1.903  -0.253   1.668  1.00  0.00           N  
HETATM   23  H1  UNL     1       8.609   1.272   0.287  1.00  0.00           H  
HETATM   24  H2  UNL     1       7.577   0.290  -0.830  1.00  0.00           H  
HETATM   25  H3  UNL     1       7.307   2.039  -0.745  1.00  0.00           H  
HETATM   26  H4  UNL     1       4.498   0.403   2.385  1.00  0.00           H  
HETATM   27  H5  UNL     1       0.781  -0.572  -2.438  1.00  0.00           H  
HETATM   28  H6  UNL     1      -1.594  -1.161  -1.969  1.00  0.00           H  
HETATM   29  H7  UNL     1      -2.883  -1.855   1.469  1.00  0.00           H  
HETATM   30  H8  UNL     1      -2.707  -3.335  -0.212  1.00  0.00           H  
HETATM   31  H9  UNL     1      -5.525  -1.581   0.268  1.00  0.00           H  
HETATM   32  H10 UNL     1      -7.046   0.237  -0.112  1.00  0.00           H  
HETATM   33  H11 UNL     1      -6.246   2.528  -0.415  1.00  0.00           H  
HETATM   34  H12 UNL     1      -3.842   2.986  -0.330  1.00  0.00           H  
HETATM   35  H13 UNL     1      -2.230   1.090   0.069  1.00  0.00           H  
HETATM   36  H14 UNL     1      -0.779  -0.918   2.220  1.00  0.00           H  
HETATM   37  H15 UNL     1       1.847  -0.257   2.715  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3
CONECT    3    4    4    5
CONECT    5    6   26
CONECT    6    7    7   22
CONECT    7    8
CONECT    8    9    9   21
CONECT    9   10   27
CONECT   10   11   11   28
CONECT   11   12   20
CONECT   12   13   14   29
CONECT   13   30
CONECT   14   15   15   19
CONECT   15   16   31
CONECT   16   17   17   32
CONECT   17   18   33
CONECT   18   19   19   34
CONECT   19   35
CONECT   20   21   21   36
CONECT   21   22
CONECT   22   37
END

HMDB0246806
     RDKit          3D
5-Hydroxymebendazole
 37 39  0  0  0  0  0  0  0  0999 V2000
    7.5986    1.1540   -0.1161 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6217    0.9193    0.8800 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3390    0.5947    0.4597 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1014    0.5235   -0.7796 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2804    0.3387    1.3706 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9833    0.0099    0.8843 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5982   -0.0987   -0.3999 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2825   -0.4276   -0.4062 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3772   -0.6637   -1.4398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9272   -0.9868   -1.1374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3978   -1.0922    0.1529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8059   -1.4415    0.4236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2046   -2.5183   -0.4032 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7487   -0.3532    0.1937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1074   -0.5940    0.1427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0044    0.4591   -0.0788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5440    1.7455   -0.2481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1690    1.9666   -0.1929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2938    0.9337    0.0240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4884   -0.8552    1.1606 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8385   -0.5262    0.8915 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9031   -0.2527    1.6682 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.6091    1.2719    0.2874 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5770    0.2901   -0.8305 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3074    2.0394   -0.7445 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4981    0.4028    2.3850 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7811   -0.5723   -2.4380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5936   -1.1614   -1.9694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8833   -1.8554    1.4689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7068   -3.3352   -0.2119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5252   -1.5813    0.2684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0461    0.2372   -0.1121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2464    2.5277   -0.4150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8416    2.9861   -0.3296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2302    1.0901    0.0689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7789   -0.9177    2.2197 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8467   -0.2568    2.7150 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  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  2  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 11 20  1  0
 20 21  2  0
 21 22  1  0
 22  6  1  0
 21  8  1  0
 19 14  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  5 26  1  0
  9 27  1  0
 10 28  1  0
 12 29  1  0
 13 30  1  0
 15 31  1  0
 16 32  1  0
 17 33  1  0
 18 34  1  0
 19 35  1  0
 20 36  1  0
 22 37  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Compound 86-162	HMDB
Methyl 5(6)-(alpha-hydroxyphenylmethyl)benzimidazole-2-carbamate	HMDB

Chemical Formula

C₁₆H₁₅N₃O₃

Average Molecular Weight

297.314

Monoisotopic Molecular Weight

297.111341355

IUPAC Name

methyl N-{6-[hydroxy(phenyl)methyl]-1H-1,3-benzodiazol-2-yl}carbamate

Traditional Name

methyl N-{5-[hydroxy(phenyl)methyl]-3H-1,3-benzodiazol-2-yl}carbamate

CAS Registry Number

Not Available

SMILES

COC(=O)NC1=NC2=C(N1)C=C(C=C2)C(O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C16H15N3O3/c1-22-16(21)19-15-17-12-8-7-11(9-13(12)18-15)14(20)10-5-3-2-4-6-10/h2-9,14,20H,1H3,(H2,17,18,19,21)

InChI Key

IIQKUGXEGMZCLE-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2-benzimidazolylcarbamic acid esters. These are aromatic heteropolycyclic compounds that contain a carbamic acid ester group, which is N-linked to the C2-atom of a benzimidazole moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzimidazoles

Sub Class

2-benzimidazolylcarbamic acid esters

Direct Parent

2-benzimidazolylcarbamic acid esters

Alternative Parents

Substituents

2-benzimidazolylcarbamic acid ester
Monocyclic benzene moiety
Benzenoid
Azole
Imidazole
Carbamic acid ester
Heteroaromatic compound
Secondary alcohol
Carbonic acid derivative
Azacycle
Organic oxygen compound
Aromatic alcohol
Alcohol
Organooxygen compound
Organonitrogen compound
Carbonyl group
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

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
logP	2.59	ALOGPS
logP	2.82	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	9.57	ChemAxon
pKa (Strongest Basic)	4.25	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	87.24 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	82.03 m³·mol⁻¹	ChemAxon
Polarizability	31.4 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
DeepCCS	[M+H]+	168.936	30932474
DeepCCS	[M-H]-	166.578	30932474
DeepCCS	[M-2H]-	200.577	30932474
DeepCCS	[M+Na]+	175.804	30932474
AllCCS	[M+H]+	170.2	32859911
AllCCS	[M+H-H2O]+	166.7	32859911
AllCCS	[M+NH4]+	173.5	32859911
AllCCS	[M+Na]+	174.4	32859911
AllCCS	[M-H]-	172.3	32859911
AllCCS	[M+Na-2H]-	171.6	32859911
AllCCS	[M+HCOO]-	171.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5-Hydroxymebendazole	COC(=O)NC1=NC2=C(N1)C=C(C=C2)C(O)C1=CC=CC=C1	3914.9	Standard polar	33892256
5-Hydroxymebendazole	COC(=O)NC1=NC2=C(N1)C=C(C=C2)C(O)C1=CC=CC=C1	2429.3	Standard non polar	33892256
5-Hydroxymebendazole	COC(=O)NC1=NC2=C(N1)C=C(C=C2)C(O)C1=CC=CC=C1	3111.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
5-Hydroxymebendazole,2TMS,isomer #1	COC(=O)N(C1=NC2=CC=C(C(O[Si](C)(C)C)C3=CC=CC=C3)C=C2[NH]1)[Si](C)(C)C	2595.6	Semi standard non polar	33892256
5-Hydroxymebendazole,2TMS,isomer #1	COC(=O)N(C1=NC2=CC=C(C(O[Si](C)(C)C)C3=CC=CC=C3)C=C2[NH]1)[Si](C)(C)C	2417.2	Standard non polar	33892256
5-Hydroxymebendazole,2TMS,isomer #1	COC(=O)N(C1=NC2=CC=C(C(O[Si](C)(C)C)C3=CC=CC=C3)C=C2[NH]1)[Si](C)(C)C	3438.2	Standard polar	33892256
5-Hydroxymebendazole,2TMS,isomer #2	COC(=O)NC1=NC2=CC=C(C(O[Si](C)(C)C)C3=CC=CC=C3)C=C2N1[Si](C)(C)C	2680.4	Semi standard non polar	33892256
5-Hydroxymebendazole,2TMS,isomer #2	COC(=O)NC1=NC2=CC=C(C(O[Si](C)(C)C)C3=CC=CC=C3)C=C2N1[Si](C)(C)C	2408.7	Standard non polar	33892256
5-Hydroxymebendazole,2TMS,isomer #2	COC(=O)NC1=NC2=CC=C(C(O[Si](C)(C)C)C3=CC=CC=C3)C=C2N1[Si](C)(C)C	3505.5	Standard polar	33892256
5-Hydroxymebendazole,2TMS,isomer #3	COC(=O)N(C1=NC2=CC=C(C(O)C3=CC=CC=C3)C=C2N1[Si](C)(C)C)[Si](C)(C)C	2679.3	Semi standard non polar	33892256
5-Hydroxymebendazole,2TMS,isomer #3	COC(=O)N(C1=NC2=CC=C(C(O)C3=CC=CC=C3)C=C2N1[Si](C)(C)C)[Si](C)(C)C	2684.4	Standard non polar	33892256
5-Hydroxymebendazole,2TMS,isomer #3	COC(=O)N(C1=NC2=CC=C(C(O)C3=CC=CC=C3)C=C2N1[Si](C)(C)C)[Si](C)(C)C	3513.5	Standard polar	33892256
5-Hydroxymebendazole,3TMS,isomer #1	COC(=O)N(C1=NC2=CC=C(C(O[Si](C)(C)C)C3=CC=CC=C3)C=C2N1[Si](C)(C)C)[Si](C)(C)C	2671.4	Semi standard non polar	33892256
5-Hydroxymebendazole,3TMS,isomer #1	COC(=O)N(C1=NC2=CC=C(C(O[Si](C)(C)C)C3=CC=CC=C3)C=C2N1[Si](C)(C)C)[Si](C)(C)C	2457.7	Standard non polar	33892256
5-Hydroxymebendazole,3TMS,isomer #1	COC(=O)N(C1=NC2=CC=C(C(O[Si](C)(C)C)C3=CC=CC=C3)C=C2N1[Si](C)(C)C)[Si](C)(C)C	3177.2	Standard polar	33892256
5-Hydroxymebendazole,2TBDMS,isomer #1	COC(=O)N(C1=NC2=CC=C(C(O[Si](C)(C)C(C)(C)C)C3=CC=CC=C3)C=C2[NH]1)[Si](C)(C)C(C)(C)C	2973.8	Semi standard non polar	33892256
5-Hydroxymebendazole,2TBDMS,isomer #1	COC(=O)N(C1=NC2=CC=C(C(O[Si](C)(C)C(C)(C)C)C3=CC=CC=C3)C=C2[NH]1)[Si](C)(C)C(C)(C)C	2878.2	Standard non polar	33892256
5-Hydroxymebendazole,2TBDMS,isomer #1	COC(=O)N(C1=NC2=CC=C(C(O[Si](C)(C)C(C)(C)C)C3=CC=CC=C3)C=C2[NH]1)[Si](C)(C)C(C)(C)C	3562.2	Standard polar	33892256
5-Hydroxymebendazole,2TBDMS,isomer #2	COC(=O)NC1=NC2=CC=C(C(O[Si](C)(C)C(C)(C)C)C3=CC=CC=C3)C=C2N1[Si](C)(C)C(C)(C)C	3067.6	Semi standard non polar	33892256
5-Hydroxymebendazole,2TBDMS,isomer #2	COC(=O)NC1=NC2=CC=C(C(O[Si](C)(C)C(C)(C)C)C3=CC=CC=C3)C=C2N1[Si](C)(C)C(C)(C)C	2865.8	Standard non polar	33892256
5-Hydroxymebendazole,2TBDMS,isomer #2	COC(=O)NC1=NC2=CC=C(C(O[Si](C)(C)C(C)(C)C)C3=CC=CC=C3)C=C2N1[Si](C)(C)C(C)(C)C	3622.0	Standard polar	33892256
5-Hydroxymebendazole,2TBDMS,isomer #3	COC(=O)N(C1=NC2=CC=C(C(O)C3=CC=CC=C3)C=C2N1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3089.6	Semi standard non polar	33892256
5-Hydroxymebendazole,2TBDMS,isomer #3	COC(=O)N(C1=NC2=CC=C(C(O)C3=CC=CC=C3)C=C2N1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3068.6	Standard non polar	33892256
5-Hydroxymebendazole,2TBDMS,isomer #3	COC(=O)N(C1=NC2=CC=C(C(O)C3=CC=CC=C3)C=C2N1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3586.6	Standard polar	33892256
5-Hydroxymebendazole,3TBDMS,isomer #1	COC(=O)N(C1=NC2=CC=C(C(O[Si](C)(C)C(C)(C)C)C3=CC=CC=C3)C=C2N1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3197.6	Semi standard non polar	33892256
5-Hydroxymebendazole,3TBDMS,isomer #1	COC(=O)N(C1=NC2=CC=C(C(O[Si](C)(C)C(C)(C)C)C3=CC=CC=C3)C=C2N1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3128.0	Standard non polar	33892256
5-Hydroxymebendazole,3TBDMS,isomer #1	COC(=O)N(C1=NC2=CC=C(C(O[Si](C)(C)C(C)(C)C)C3=CC=CC=C3)C=C2N1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3416.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Hydroxymebendazole GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-0940000000-3073925b686d8234f807	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Hydroxymebendazole GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Hydroxymebendazole GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Hydroxymebendazole GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Hydroxymebendazole GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Hydroxymebendazole GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Hydroxymebendazole GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Hydroxymebendazole GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxymebendazole 10V, Positive-QTOF	splash10-001i-0090000000-e98ee3bed238a2732fbe	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxymebendazole 20V, Positive-QTOF	splash10-0uea-0090000000-ea5a9261de66d200b1a1	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxymebendazole 40V, Positive-QTOF	splash10-0f6w-3490000000-91424bb1e966ea8285d8	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxymebendazole 10V, Negative-QTOF	splash10-03di-0190000000-b13247c0c22b9b009dbe	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxymebendazole 20V, Negative-QTOF	splash10-03di-0390000000-eda96d2f05822405a8c8	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxymebendazole 40V, Negative-QTOF	splash10-000g-6790000000-f9d1df0c49db42bd139f	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

39410

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

43242

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for 5-Hydroxymebendazole (HMDB0246806)

MOL for HMDB0246806 (5-Hydroxymebendazole)

3D MOL for HMDB0246806 (5-Hydroxymebendazole)

3D SDF for HMDB0246806 (5-Hydroxymebendazole)

3D-SDF for HMDB0246806 (5-Hydroxymebendazole)

PDB for HMDB0246806 (5-Hydroxymebendazole)

3D PDB for HMDB0246806 (5-Hydroxymebendazole)

SMILES for HMDB0246806 (5-Hydroxymebendazole)

INCHI for HMDB0246806 (5-Hydroxymebendazole)

Structure for HMDB0246806 (5-Hydroxymebendazole)

3D Structure for HMDB0246806 (5-Hydroxymebendazole)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra