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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 12:21:39 UTC

Update Date

2021-09-26 23:06:54 UTC

HMDB ID

HMDB0253588

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Irtemazole

Description

6-[(1H-imidazol-1-yl)(phenyl)methyl]-2-methyl-1H-1,3-benzodiazole 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). Based on a literature review very few articles have been published on 6-[(1H-imidazol-1-yl)(phenyl)methyl]-2-methyl-1H-1,3-benzodiazole. This compound has been identified in human blood as reported by (PMID: 31557052 ). Irtemazole is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Irtemazole 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

HMDB0253588
     RDKit          3D
Irtemazole
 38 41  0  0  0  0  0  0  0  0999 V2000
    5.7372   -2.3094    0.5566 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3488   -1.7458    0.6660 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4595   -1.9541    1.6534 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3200   -1.2772    1.3975 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1116   -1.1320    2.0488 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0814   -0.3589    1.5576 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2539    0.3046    0.3619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7721    1.1539   -0.2569 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6665    0.4395   -1.1699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8002   -0.1407   -0.6395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7060   -0.8381   -1.4334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4458   -0.9368   -2.7625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3147   -0.3576   -3.2895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4113    0.3355   -2.5109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5688    1.8855    0.7335 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8193    2.3426    0.6459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1428    2.9707    1.8327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0568    2.8746    2.6225 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0886    2.2050    1.9413 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4623    0.1594   -0.2893 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4972   -0.6162    0.2024 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7364   -0.9256   -0.2071 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7139   -3.4041    0.4331 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1991   -1.8736   -0.3404 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3438   -2.0565    1.4478 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9622   -1.6560    3.0031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8657   -0.2463    2.0690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2440    1.9375   -0.8680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0610   -0.0957    0.4158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5930   -1.2894   -1.0046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1644   -1.4864   -3.3732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1463   -0.4625   -4.3630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5128    0.7911   -2.9538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4417    2.2118   -0.2476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1071    3.4499    2.0658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1132    2.0082    2.3877 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6667    0.6545   -1.2369 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1483   -0.5614   -1.0960 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
  8 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
  7 20  1  0
 20 21  2  0
 21 22  1  0
 22  2  1  0
 21  4  1  0
 14  9  1  0
 19 15  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  5 26  1  0
  6 27  1  0
  8 28  1  0
 10 29  1  0
 11 30  1  0
 12 31  1  0
 13 32  1  0
 14 33  1  0
 16 34  1  0
 17 35  1  0
 19 36  1  0
 20 37  1  0
 22 38  1  0
M  END


  Mrv1652309112114212D          

 22 25  0  0  0  0            999 V2000
   -1.4534   -0.6979    0.0000 C   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 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1171    1.4370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3720    2.2216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1970    2.2216    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4520    1.4370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  2  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  4 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
 11 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 18 22  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0253588

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=NC2=C(N1)C=C(C=C2)C(N1C=CN=C1)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C18H16N4/c1-13-20-16-8-7-15(11-17(16)21-13)18(22-10-9-19-12-22)14-5-3-2-4-6-14/h2-12,18H,1H3,(H,20,21)

> <INCHI_KEY>
DCGOMTSIZLGUOK-UHFFFAOYSA-N

> <FORMULA>
C18H16N4

> <MOLECULAR_WEIGHT>
288.354

> <EXACT_MASS>
288.137496531

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
31.979586811843934

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-[(1H-imidazol-1-yl)(phenyl)methyl]-2-methyl-1H-1,3-benzodiazole

> <ALOGPS_LOGP>
3.40

> <JCHEM_LOGP>
2.9964880769999995

> <ALOGPS_LOGS>
-4.00

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.651831890201759

> <JCHEM_PKA_STRONGEST_BASIC>
6.860175745159109

> <JCHEM_POLAR_SURFACE_AREA>
46.5

> <JCHEM_REFRACTIVITY>
86.15610000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.89e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
irtemazole

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0253588
     RDKit          3D
Irtemazole
 38 41  0  0  0  0  0  0  0  0999 V2000
    5.7372   -2.3094    0.5566 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3488   -1.7458    0.6660 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4595   -1.9541    1.6534 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3200   -1.2772    1.3975 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1116   -1.1320    2.0488 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0814   -0.3589    1.5576 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2539    0.3046    0.3619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7721    1.1539   -0.2569 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6665    0.4395   -1.1699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8002   -0.1407   -0.6395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7060   -0.8381   -1.4334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4458   -0.9368   -2.7625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3147   -0.3576   -3.2895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4113    0.3355   -2.5109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5688    1.8855    0.7335 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8193    2.3426    0.6459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1428    2.9707    1.8327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0568    2.8746    2.6225 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0886    2.2050    1.9413 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4623    0.1594   -0.2893 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4972   -0.6162    0.2024 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7364   -0.9256   -0.2071 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7139   -3.4041    0.4331 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1991   -1.8736   -0.3404 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3438   -2.0565    1.4478 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9622   -1.6560    3.0031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8657   -0.2463    2.0690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2440    1.9375   -0.8680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0610   -0.0957    0.4158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5930   -1.2894   -1.0046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1644   -1.4864   -3.3732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1463   -0.4625   -4.3630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5128    0.7911   -2.9538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4417    2.2118   -0.2476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1071    3.4499    2.0658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1132    2.0082    2.3877 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6667    0.6545   -1.2369 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1483   -0.5614   -1.0960 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
  8 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
  7 20  1  0
 20 21  2  0
 21 22  1  0
 22  2  1  0
 21  4  1  0
 14  9  1  0
 19 15  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  5 26  1  0
  6 27  1  0
  8 28  1  0
 10 29  1  0
 11 30  1  0
 12 31  1  0
 13 32  1  0
 14 33  1  0
 16 34  1  0
 17 35  1  0
 19 36  1  0
 20 37  1  0
 22 38  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      -2.713  -1.303   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.173  -1.303   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      -0.268  -2.549   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       1.197  -2.073   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.197  -0.533   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      -0.268  -0.057   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       2.530   0.237   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.864  -0.533   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.864  -2.073   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.530  -2.843   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.198   0.237   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.531  -0.533   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.865   0.237   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.199  -0.533   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.199  -2.073   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.865  -2.843   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.531  -2.073   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       5.198   1.777   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0       3.952   2.682   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.428   4.147   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0       5.968   4.147   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0       6.444   2.682   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    2                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9    4                                                       
CONECT   11    8   12   18                                                  
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12                                                       
CONECT   18   11   19   22                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   18                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

COMPND    HMDB0253588
HETATM    1  C1  UNL     1       5.737  -2.309   0.557  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.349  -1.746   0.666  1.00  0.00           C  
HETATM    3  N1  UNL     1       3.459  -1.954   1.653  1.00  0.00           N  
HETATM    4  C3  UNL     1       2.320  -1.277   1.398  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.112  -1.132   2.049  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.081  -0.359   1.558  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.254   0.305   0.362  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.772   1.154  -0.257  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.666   0.440  -1.170  1.00  0.00           C  
HETATM   10  C9  UNL     1      -2.800  -0.141  -0.640  1.00  0.00           C  
HETATM   11  C10 UNL     1      -3.706  -0.838  -1.433  1.00  0.00           C  
HETATM   12  C11 UNL     1      -3.446  -0.937  -2.762  1.00  0.00           C  
HETATM   13  C12 UNL     1      -2.315  -0.358  -3.290  1.00  0.00           C  
HETATM   14  C13 UNL     1      -1.411   0.336  -2.511  1.00  0.00           C  
HETATM   15  N2  UNL     1      -1.569   1.885   0.733  1.00  0.00           N  
HETATM   16  C14 UNL     1      -2.819   2.343   0.646  1.00  0.00           C  
HETATM   17  C15 UNL     1      -3.143   2.971   1.833  1.00  0.00           C  
HETATM   18  N3  UNL     1      -2.057   2.875   2.623  1.00  0.00           N  
HETATM   19  C16 UNL     1      -1.089   2.205   1.941  1.00  0.00           C  
HETATM   20  C17 UNL     1       1.462   0.159  -0.289  1.00  0.00           C  
HETATM   21  C18 UNL     1       2.497  -0.616   0.202  1.00  0.00           C  
HETATM   22  N4  UNL     1       3.736  -0.926  -0.207  1.00  0.00           N  
HETATM   23  H1  UNL     1       5.714  -3.404   0.433  1.00  0.00           H  
HETATM   24  H2  UNL     1       6.199  -1.874  -0.340  1.00  0.00           H  
HETATM   25  H3  UNL     1       6.344  -2.057   1.448  1.00  0.00           H  
HETATM   26  H4  UNL     1       0.962  -1.656   3.003  1.00  0.00           H  
HETATM   27  H5  UNL     1      -0.866  -0.246   2.069  1.00  0.00           H  
HETATM   28  H6  UNL     1      -0.244   1.937  -0.868  1.00  0.00           H  
HETATM   29  H7  UNL     1      -3.061  -0.096   0.416  1.00  0.00           H  
HETATM   30  H8  UNL     1      -4.593  -1.289  -1.005  1.00  0.00           H  
HETATM   31  H9  UNL     1      -4.164  -1.486  -3.373  1.00  0.00           H  
HETATM   32  H10 UNL     1      -2.146  -0.462  -4.363  1.00  0.00           H  
HETATM   33  H11 UNL     1      -0.513   0.791  -2.954  1.00  0.00           H  
HETATM   34  H12 UNL     1      -3.442   2.212  -0.248  1.00  0.00           H  
HETATM   35  H13 UNL     1      -4.107   3.450   2.066  1.00  0.00           H  
HETATM   36  H14 UNL     1      -0.113   2.008   2.388  1.00  0.00           H  
HETATM   37  H15 UNL     1       1.667   0.655  -1.237  1.00  0.00           H  
HETATM   38  H16 UNL     1       4.148  -0.561  -1.096  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3    3   22
CONECT    3    4
CONECT    4    5    5   21
CONECT    5    6   26
CONECT    6    7    7   27
CONECT    7    8   20
CONECT    8    9   15   28
CONECT    9   10   10   14
CONECT   10   11   29
CONECT   11   12   12   30
CONECT   12   13   31
CONECT   13   14   14   32
CONECT   14   33
CONECT   15   16   19
CONECT   16   17   17   34
CONECT   17   18   35
CONECT   18   19   19
CONECT   19   36
CONECT   20   21   21   37
CONECT   21   22
CONECT   22   38
END

HMDB0253588
     RDKit          3D
Irtemazole
 38 41  0  0  0  0  0  0  0  0999 V2000
    5.7372   -2.3094    0.5566 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3488   -1.7458    0.6660 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4595   -1.9541    1.6534 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3200   -1.2772    1.3975 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1116   -1.1320    2.0488 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0814   -0.3589    1.5576 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2539    0.3046    0.3619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7721    1.1539   -0.2569 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6665    0.4395   -1.1699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8002   -0.1407   -0.6395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7060   -0.8381   -1.4334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4458   -0.9368   -2.7625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3147   -0.3576   -3.2895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4113    0.3355   -2.5109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5688    1.8855    0.7335 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8193    2.3426    0.6459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1428    2.9707    1.8327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0568    2.8746    2.6225 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0886    2.2050    1.9413 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4623    0.1594   -0.2893 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4972   -0.6162    0.2024 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7364   -0.9256   -0.2071 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7139   -3.4041    0.4331 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1991   -1.8736   -0.3404 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3438   -2.0565    1.4478 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9622   -1.6560    3.0031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8657   -0.2463    2.0690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2440    1.9375   -0.8680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0610   -0.0957    0.4158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5930   -1.2894   -1.0046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1644   -1.4864   -3.3732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1463   -0.4625   -4.3630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5128    0.7911   -2.9538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4417    2.2118   -0.2476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1071    3.4499    2.0658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1132    2.0082    2.3877 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6667    0.6545   -1.2369 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1483   -0.5614   -1.0960 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
  8 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
  7 20  1  0
 20 21  2  0
 21 22  1  0
 22  2  1  0
 21  4  1  0
 14  9  1  0
 19 15  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  5 26  1  0
  6 27  1  0
  8 28  1  0
 10 29  1  0
 11 30  1  0
 12 31  1  0
 13 32  1  0
 14 33  1  0
 16 34  1  0
 17 35  1  0
 19 36  1  0
 20 37  1  0
 22 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
5-((1H-Imidazol-1-yl)phenylmethyl)-2-methyl-1H-benzimidazole	MeSH

Chemical Formula

C₁₈H₁₆N₄

Average Molecular Weight

288.354

Monoisotopic Molecular Weight

288.137496531

IUPAC Name

6-[(1H-imidazol-1-yl)(phenyl)methyl]-2-methyl-1H-1,3-benzodiazole

Traditional Name

irtemazole

CAS Registry Number

Not Available

SMILES

CC1=NC2=C(N1)C=C(C=C2)C(N1C=CN=C1)C1=CC=CC=C1

InChI Identifier

InChI=1S/C18H16N4/c1-13-20-16-8-7-15(11-17(16)21-13)18(22-10-9-19-12-22)14-5-3-2-4-6-14/h2-12,18H,1H3,(H,20,21)

InChI Key

DCGOMTSIZLGUOK-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
N-substituted imidazole
Monocyclic benzene moiety
Heteroaromatic compound
Imidazole
Azole
Azacycle
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen 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)

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	3.4	ALOGPS
logP	3	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	12.65	ChemAxon
pKa (Strongest Basic)	6.86	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.5 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	86.16 m³·mol⁻¹	ChemAxon
Polarizability	31.98 Å³	ChemAxon
Number of Rings	4	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]+	166.127	30932474
DeepCCS	[M-H]-	163.769	30932474
DeepCCS	[M-2H]-	197.576	30932474
DeepCCS	[M+Na]+	172.804	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Irtemazole	CC1=NC2=C(N1)C=C(C=C2)C(N1C=CN=C1)C1=CC=CC=C1	4164.8	Standard polar	33892256
Irtemazole	CC1=NC2=C(N1)C=C(C=C2)C(N1C=CN=C1)C1=CC=CC=C1	2743.9	Standard non polar	33892256
Irtemazole	CC1=NC2=C(N1)C=C(C=C2)C(N1C=CN=C1)C1=CC=CC=C1	3067.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Irtemazole,1TMS,isomer #1	CC1=NC2=CC=C(C(C3=CC=CC=C3)N3C=CN=C3)C=C2N1[Si](C)(C)C	2790.5	Semi standard non polar	33892256
Irtemazole,1TMS,isomer #1	CC1=NC2=CC=C(C(C3=CC=CC=C3)N3C=CN=C3)C=C2N1[Si](C)(C)C	2714.9	Standard non polar	33892256
Irtemazole,1TMS,isomer #1	CC1=NC2=CC=C(C(C3=CC=CC=C3)N3C=CN=C3)C=C2N1[Si](C)(C)C	3412.6	Standard polar	33892256
Irtemazole,1TBDMS,isomer #1	CC1=NC2=CC=C(C(C3=CC=CC=C3)N3C=CN=C3)C=C2N1[Si](C)(C)C(C)(C)C	2978.0	Semi standard non polar	33892256
Irtemazole,1TBDMS,isomer #1	CC1=NC2=CC=C(C(C3=CC=CC=C3)N3C=CN=C3)C=C2N1[Si](C)(C)C(C)(C)C	2841.9	Standard non polar	33892256
Irtemazole,1TBDMS,isomer #1	CC1=NC2=CC=C(C(C3=CC=CC=C3)N3C=CN=C3)C=C2N1[Si](C)(C)C(C)(C)C	3446.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Irtemazole GC-MS (Non-derivatized) - 70eV, Positive	splash10-05i3-6790000000-58ebf4a59cfafed9545e	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Irtemazole GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Irtemazole 10V, Positive-QTOF	splash10-00di-0090000000-01483f71d08f072138cc	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Irtemazole 20V, Positive-QTOF	splash10-00di-0190000000-ffd9d77db284679723bf	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Irtemazole 40V, Positive-QTOF	splash10-0537-3960000000-4ab97a3092262125b106	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Irtemazole 10V, Negative-QTOF	splash10-000i-0090000000-2cd468bf1bc7f1e34a1e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Irtemazole 20V, Negative-QTOF	splash10-00kr-1090000000-6d19fa5021c9210593f0	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Irtemazole 40V, Negative-QTOF	splash10-014i-9010000000-973209b3374ded62afc9	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

64436

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71330

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 Irtemazole (HMDB0253588)

MOL for HMDB0253588 (Irtemazole)

3D MOL for HMDB0253588 (Irtemazole)

3D SDF for HMDB0253588 (Irtemazole)

3D-SDF for HMDB0253588 (Irtemazole)

PDB for HMDB0253588 (Irtemazole)

3D PDB for HMDB0253588 (Irtemazole)

SMILES for HMDB0253588 (Irtemazole)

INCHI for HMDB0253588 (Irtemazole)

Structure for HMDB0253588 (Irtemazole)

3D Structure for HMDB0253588 (Irtemazole)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra