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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:45:20 UTC

Update Date

2022-03-07 02:53:06 UTC

HMDB ID

HMDB0031767

Secondary Accession Numbers

HMDB31767

Metabolite Identification

Common Name

Benomyl

Description

Benomyl, also known as benlate or benlic acid, 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 significant number of articles have been published on Benomyl.

Structure

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

HMDB0031767
     RDKit          3D
Benomyl
 39 40  0  0  0  0  0  0  0  0999 V2000
    5.6079    0.2069   -0.0760 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4461    1.1609   -0.0719 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1492    0.4389   -0.3185 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0067    1.4328   -0.3066 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7384    0.8189   -0.5348 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1611   -0.0011    0.2645 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7927   -0.3354    1.4475 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1017   -0.5636   -0.0440 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2618    0.0914   -0.2856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4585    1.5028   -0.2802 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2916    2.0661    0.5131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0327    1.3126    1.3976 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4609    3.4335    0.4961 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8750    4.1487   -0.5857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2098   -0.8172   -0.5346 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7069   -2.0659   -0.4643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2662   -3.3165   -0.6367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4879   -4.4561   -0.4996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1552   -4.3037   -0.1898 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6173   -3.0428   -0.0219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3732   -1.8977   -0.1537 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5164    0.8086    0.1893 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8042   -0.1951   -1.0899 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4864   -0.6150    0.6567 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3854    1.6816    0.8910 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6128    1.8691   -0.9256 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2124   -0.0498   -1.3159 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9525   -0.2970    0.4797 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1792    2.1648   -1.1352 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0694    2.0125    0.6329 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4838    0.0367    2.3385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7617    0.7047    0.9925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7705    4.0135   -0.6229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0601    5.2256   -0.3789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3743    3.8995   -1.5421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3112   -3.4569   -0.8804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8972   -5.4591   -0.6289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5494   -5.2024   -0.0835 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4185   -2.9547    0.2179 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  1  0
  5  6  2  3
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  3
 11 12  1  0
 11 13  1  0
 13 14  1  0
  9 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21  8  1  0
 21 16  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  7 31  1  0
 12 32  1  0
 14 33  1  0
 14 34  1  0
 14 35  1  0
 17 36  1  0
 18 37  1  0
 19 38  1  0
 20 39  1  0
M  END


  Mrv0541 09051416302D          

 21 22  0  0  0  0            999 V2000
    2.0300    6.3835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8212    0.0940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4780    5.7704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7329    4.9858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1809    4.3727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    2.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5837    0.8085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4358    3.5881    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    1.5229    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0768    3.1465    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    0.0940    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4087    0.8085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  3  1  0  0  0  0
  6  5  2  0  0  0  0
  7  5  1  0  0  0  0
  8  6  1  0  0  0  0
  9  4  1  0  0  0  0
 10  7  2  0  0  0  0
 11  8  2  0  0  0  0
 11 10  1  0  0  0  0
 15  9  1  4  0  0  0
 15 13  2  0  0  0  0
 16 10  1  0  0  0  0
 16 12  2  0  0  0  0
 17 12  1  4  0  0  0
 17 14  2  0  0  0  0
 18 11  1  0  0  0  0
 18 12  1  0  0  0  0
 18 13  1  0  0  0  0
 19 13  1  0  0  0  0
 20 14  1  0  0  0  0
 21  2  1  0  0  0  0
 21 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0031767

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCN=C(O)N1C(N=C(O)OC)=NC2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C14H18N4O3/c1-3-4-9-15-13(19)18-11-8-6-5-7-10(11)16-12(18)17-14(20)21-2/h5-8H,3-4,9H2,1-2H3,(H,15,19)(H,16,17,20)

> <INCHI_KEY>
RIOXQFHNBCKOKP-UHFFFAOYSA-N

> <FORMULA>
C14H18N4O3

> <MOLECULAR_WEIGHT>
290.3177

> <EXACT_MASS>
290.137890462

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
31.147726515768504

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-butyl-2-{[hydroxy(methoxy)methylidene]amino}-1H-1,3-benzodiazole-1-carboximidic acid

> <ALOGPS_LOGP>
2.32

> <JCHEM_LOGP>
3.675432968180298

> <ALOGPS_LOGS>
-3.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
8.890579877359658

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.6065139072132073

> <JCHEM_PKA_STRONGEST_BASIC>
2.7610394248508414

> <JCHEM_POLAR_SURFACE_AREA>
92.23

> <JCHEM_REFRACTIVITY>
79.487

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.45e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
benomyl

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0031767
     RDKit          3D
Benomyl
 39 40  0  0  0  0  0  0  0  0999 V2000
    5.6079    0.2069   -0.0760 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4461    1.1609   -0.0719 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1492    0.4389   -0.3185 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0067    1.4328   -0.3066 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7384    0.8189   -0.5348 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1611   -0.0011    0.2645 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7927   -0.3354    1.4475 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1017   -0.5636   -0.0440 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2618    0.0914   -0.2856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4585    1.5028   -0.2802 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2916    2.0661    0.5131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0327    1.3126    1.3976 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4609    3.4335    0.4961 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8750    4.1487   -0.5857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2098   -0.8172   -0.5346 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7069   -2.0659   -0.4643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2662   -3.3165   -0.6367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4879   -4.4561   -0.4996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1552   -4.3037   -0.1898 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6173   -3.0428   -0.0219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3732   -1.8977   -0.1537 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5164    0.8086    0.1893 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8042   -0.1951   -1.0899 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4864   -0.6150    0.6567 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3854    1.6816    0.8910 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6128    1.8691   -0.9256 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2124   -0.0498   -1.3159 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9525   -0.2970    0.4797 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1792    2.1648   -1.1352 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0694    2.0125    0.6329 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4838    0.0367    2.3385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7617    0.7047    0.9925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7705    4.0135   -0.6229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0601    5.2256   -0.3789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3743    3.8995   -1.5421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3112   -3.4569   -0.8804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8972   -5.4591   -0.6289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5494   -5.2024   -0.0835 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4185   -2.9547    0.2179 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  1  0
  5  6  2  3
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  3
 11 12  1  0
 11 13  1  0
 13 14  1  0
  9 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21  8  1  0
 21 16  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  7 31  1  0
 12 32  1  0
 14 33  1  0
 14 34  1  0
 14 35  1  0
 17 36  1  0
 18 37  1  0
 19 38  1  0
 20 39  1  0
M  END

HEADER    PROTEIN                                 05-SEP-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-14         0                                  
HETATM    1  C   UNK     0       3.789  11.916   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.400   0.175   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.759  10.771   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.235   9.307   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.204   8.162   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.650   5.553   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.090   1.509   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       2.680   6.698   0.000  0.00  0.00           N+0
HETATM   16  N   UNK     0       2.126   1.597   0.000  0.00  0.00           N+0
HETATM   17  N   UNK     0      -0.320   2.843   0.000  0.00  0.00           N+0
HETATM   18  N   UNK     0       2.126   4.089   0.000  0.00  0.00           N+0
HETATM   19  O   UNK     0       0.143   5.874   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -0.320   0.175   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -2.630   1.509   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2   21                                                            
CONECT    3    1    4                                                       
CONECT    4    3    9                                                       
CONECT    5    6    7                                                       
CONECT    6    5    8                                                       
CONECT    7    5   10                                                       
CONECT    8    6   11                                                       
CONECT    9    4   15                                                       
CONECT   10    7   11   16                                                  
CONECT   11    8   10   18                                                  
CONECT   12   16   17   18                                                  
CONECT   13   15   18   19                                                  
CONECT   14   17   20   21                                                  
CONECT   15    9   13                                                       
CONECT   16   10   12                                                       
CONECT   17   12   14                                                       
CONECT   18   11   12   13                                                  
CONECT   19   13                                                            
CONECT   20   14                                                            
CONECT   21    2   14                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

COMPND    HMDB0031767
HETATM    1  C1  UNL     1       5.608   0.207  -0.076  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.446   1.161  -0.072  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.149   0.439  -0.318  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.007   1.433  -0.307  1.00  0.00           C  
HETATM    5  N1  UNL     1       0.738   0.819  -0.535  1.00  0.00           N  
HETATM    6  C5  UNL     1       0.161  -0.001   0.265  1.00  0.00           C  
HETATM    7  O1  UNL     1       0.793  -0.335   1.448  1.00  0.00           O  
HETATM    8  N2  UNL     1      -1.102  -0.564  -0.044  1.00  0.00           N  
HETATM    9  C6  UNL     1      -2.262   0.091  -0.286  1.00  0.00           C  
HETATM   10  N3  UNL     1      -2.459   1.503  -0.280  1.00  0.00           N  
HETATM   11  C7  UNL     1      -3.292   2.066   0.513  1.00  0.00           C  
HETATM   12  O2  UNL     1      -4.033   1.313   1.398  1.00  0.00           O  
HETATM   13  O3  UNL     1      -3.461   3.433   0.496  1.00  0.00           O  
HETATM   14  C8  UNL     1      -2.875   4.149  -0.586  1.00  0.00           C  
HETATM   15  N4  UNL     1      -3.210  -0.817  -0.535  1.00  0.00           N  
HETATM   16  C9  UNL     1      -2.707  -2.066  -0.464  1.00  0.00           C  
HETATM   17  C10 UNL     1      -3.266  -3.317  -0.637  1.00  0.00           C  
HETATM   18  C11 UNL     1      -2.488  -4.456  -0.500  1.00  0.00           C  
HETATM   19  C12 UNL     1      -1.155  -4.304  -0.190  1.00  0.00           C  
HETATM   20  C13 UNL     1      -0.617  -3.043  -0.022  1.00  0.00           C  
HETATM   21  C14 UNL     1      -1.373  -1.898  -0.154  1.00  0.00           C  
HETATM   22  H1  UNL     1       6.516   0.809   0.189  1.00  0.00           H  
HETATM   23  H2  UNL     1       5.804  -0.195  -1.090  1.00  0.00           H  
HETATM   24  H3  UNL     1       5.486  -0.615   0.657  1.00  0.00           H  
HETATM   25  H4  UNL     1       4.385   1.682   0.891  1.00  0.00           H  
HETATM   26  H5  UNL     1       4.613   1.869  -0.926  1.00  0.00           H  
HETATM   27  H6  UNL     1       3.212  -0.050  -1.316  1.00  0.00           H  
HETATM   28  H7  UNL     1       2.952  -0.297   0.480  1.00  0.00           H  
HETATM   29  H8  UNL     1       2.179   2.165  -1.135  1.00  0.00           H  
HETATM   30  H9  UNL     1       2.069   2.012   0.633  1.00  0.00           H  
HETATM   31  H10 UNL     1       0.484   0.037   2.339  1.00  0.00           H  
HETATM   32  H11 UNL     1      -4.762   0.705   0.992  1.00  0.00           H  
HETATM   33  H12 UNL     1      -1.770   4.014  -0.623  1.00  0.00           H  
HETATM   34  H13 UNL     1      -3.060   5.226  -0.379  1.00  0.00           H  
HETATM   35  H14 UNL     1      -3.374   3.899  -1.542  1.00  0.00           H  
HETATM   36  H15 UNL     1      -4.311  -3.457  -0.880  1.00  0.00           H  
HETATM   37  H16 UNL     1      -2.897  -5.459  -0.629  1.00  0.00           H  
HETATM   38  H17 UNL     1      -0.549  -5.202  -0.083  1.00  0.00           H  
HETATM   39  H18 UNL     1       0.418  -2.955   0.218  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3   25   26
CONECT    3    4   27   28
CONECT    4    5   29   30
CONECT    5    6    6
CONECT    6    7    8
CONECT    7   31
CONECT    8    9   21
CONECT    9   10   15   15
CONECT   10   11   11
CONECT   11   12   13
CONECT   12   32
CONECT   13   14
CONECT   14   33   34   35
CONECT   15   16
CONECT   16   17   17   21
CONECT   17   18   36
CONECT   18   19   19   37
CONECT   19   20   38
CONECT   20   21   21   39
END

HMDB0031767
     RDKit          3D
Benomyl
 39 40  0  0  0  0  0  0  0  0999 V2000
    5.6079    0.2069   -0.0760 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4461    1.1609   -0.0719 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1492    0.4389   -0.3185 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0067    1.4328   -0.3066 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7384    0.8189   -0.5348 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1611   -0.0011    0.2645 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7927   -0.3354    1.4475 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1017   -0.5636   -0.0440 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2618    0.0914   -0.2856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4585    1.5028   -0.2802 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2916    2.0661    0.5131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0327    1.3126    1.3976 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4609    3.4335    0.4961 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8750    4.1487   -0.5857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2098   -0.8172   -0.5346 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7069   -2.0659   -0.4643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2662   -3.3165   -0.6367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4879   -4.4561   -0.4996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1552   -4.3037   -0.1898 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6173   -3.0428   -0.0219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3732   -1.8977   -0.1537 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5164    0.8086    0.1893 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8042   -0.1951   -1.0899 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4864   -0.6150    0.6567 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3854    1.6816    0.8910 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6128    1.8691   -0.9256 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2124   -0.0498   -1.3159 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9525   -0.2970    0.4797 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1792    2.1648   -1.1352 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0694    2.0125    0.6329 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4838    0.0367    2.3385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7617    0.7047    0.9925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7705    4.0135   -0.6229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0601    5.2256   -0.3789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3743    3.8995   -1.5421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3112   -3.4569   -0.8804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8972   -5.4591   -0.6289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5494   -5.2024   -0.0835 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4185   -2.9547    0.2179 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  1  0
  5  6  2  3
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  3
 11 12  1  0
 11 13  1  0
 13 14  1  0
  9 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21  8  1  0
 21 16  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  7 31  1  0
 12 32  1  0
 14 33  1  0
 14 34  1  0
 14 35  1  0
 17 36  1  0
 18 37  1  0
 19 38  1  0
 20 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-(Butylcarbamoyl)-2-benzimidazol-methylcarbamat	ChEBI
1-(Butylcarbamoyl)-2-benzimidazolecarbamic acid, methyl ester	ChEBI
1-(N-Butylcarbamoyl)-2-(methoxy-carboxamido)-benzimidazol	ChEBI
Benlate	ChEBI
Methyl 1-(butylamino)carbonyl-1H-benzimidazol-2-ylcarbamate	ChEBI
Methyl 1-(butylcarbamoyl)-2-benzimidazolecarbamate	ChEBI
Methyl N-(1-butylcarbamoyl-2-benzimidazole)carbamate	ChEBI
1-(Butylcarbamoyl)-2-benzimidazolecarbamate, methyl ester	Generator
Benlic acid	Generator
Methyl 1-(butylamino)carbonyl-1H-benzimidazol-2-ylcarbamic acid	Generator
Methyl 1-(butylcarbamoyl)-2-benzimidazolecarbamic acid	Generator
Methyl N-(1-butylcarbamoyl-2-benzimidazole)carbamic acid	Generator
Agrocit	HMDB
Arbortrine	HMDB
Arilate	HMDB
BBC	HMDB
Benex	HMDB
Benlat	HMDB
Benlate 50	HMDB
Benlate 50 W	HMDB
Benlate 50W	HMDB
Benomil	HMDB
Benomyl 50W	HMDB
Benomyl-imex	HMDB
Benosan	HMDB
BNM	HMDB
Chinoin-fundazol	HMDB
Du pont 1991	HMDB
Dupont 1991	HMDB
Fibenzol	HMDB
Fundasol	HMDB
Fundazol	HMDB
Fundazol 50WP	HMDB
Fungicide 1991	HMDB
Fungicide D-1991	HMDB
Fungochrom	HMDB
Kribenomy	HMDB
Kribenomyl	HMDB
MBCL	HMDB
Methyl 1-(butylcarbamoyl)-2-benzimidazolylcarbamate	HMDB
Methyl 1-(butylcarbamoyl)benzimidazol-2-ylcarbamate	HMDB
Methyl 1-[(butylamino)carbonyl]-1H-benzimidazol-2-ylcarbamate, 9ci	HMDB
Methyl [1-(butylcarbamoyl)-1H-benzimidazol-2-yl]carbamate	HMDB
NS 02 (Fungicide)	HMDB
Tersan 1991	HMDB
Uzgen	HMDB

Chemical Formula

C₁₄H₁₈N₄O₃

Average Molecular Weight

290.3177

Monoisotopic Molecular Weight

290.137890462

IUPAC Name

N-butyl-2-{[hydroxy(methoxy)methylidene]amino}-1H-1,3-benzodiazole-1-carboximidic acid

Traditional Name

benomyl

CAS Registry Number

17804-35-2

SMILES

CCCCN=C(O)N1C(N=C(O)OC)=NC2=CC=CC=C12

InChI Identifier

InChI=1S/C14H18N4O3/c1-3-4-9-15-13(19)18-11-8-6-5-7-10(11)16-12(18)17-14(20)21-2/h5-8H,3-4,9H2,1-2H3,(H,15,19)(H,16,17,20)

InChI Key

RIOXQFHNBCKOKP-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
Imidazole-1-carbonyl group
N-substituted imidazole
Benzenoid
Azole
Imidazole
Carbamic acid ester
Heteroaromatic compound
Urea
Carbonic acid derivative
Azacycle
Organopnictogen compound
Carbonyl group
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

carbamate ester (CHEBI:3015 )
aromatic amide (CHEBI:3015 )
benzimidazoles (CHEBI:3015 )
benzimidazolylcarbamate fungicide (CHEBI:3015 )
benzimidazole fungicide (CHEBI:3015 )
Carbamate pesticides (C10896 )
Carbamate fungicides (C10896 )

Ontology

Physiological effect

Health effect

Pregnancy (HMDB: HMDB0031767)
Skin irritation (HMDB: HMDB0031767)

Disposition

Biological location

Cellular substructure

Route of exposure

Parenteral

Dermal (HMDB: HMDB0031767)
Inhalation (HMDB: HMDB0031767)

Enteral

Ingestion (HMDB: HMDB0031767)

Source

Endogenous

Endogenous (HMDB: HMDB0031767)

Exogenous

Food

Food (HMDB: HMDB0031767)

Not Available

Tubulin modulator (HMDB: HMDB0031767)

Inhibitor

Enzyme inhibitor

tubulin modulator (HMDB: HMDB0031767)

microtubule-destabilising agent (HMDB: HMDB0031767)

Environmental role

Air pollutant (HMDB: HMDB0031767)

Industrial application

Pharmaceutical industry

anthelminthic drug (HMDB: HMDB0031767)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	140 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0038 mg/mL at 20 °C	Not Available
LogP	2.12	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.36 g/L	ALOGPS
logP	2.32	ALOGPS
logP	3.68	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	3.61	ChemAxon
pKa (Strongest Basic)	2.76	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	92.23 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	79.49 m³·mol⁻¹	ChemAxon
Polarizability	31.15 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]+	170.22	31661259
DarkChem	[M-H]-	167.605	31661259
DeepCCS	[M-2H]-	195.228	30932474
DeepCCS	[M+Na]+	170.794	30932474
AllCCS	[M+H]+	167.5	32859911
AllCCS	[M+H-H2O]+	164.3	32859911
AllCCS	[M+NH4]+	170.4	32859911
AllCCS	[M+Na]+	171.3	32859911
AllCCS	[M-H]-	168.8	32859911
AllCCS	[M+Na-2H]-	168.8	32859911
AllCCS	[M+HCOO]-	169.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Benomyl	CCCCN=C(O)N1C(N=C(O)OC)=NC2=CC=CC=C12	3371.8	Standard polar	33892256
Benomyl	CCCCN=C(O)N1C(N=C(O)OC)=NC2=CC=CC=C12	2428.1	Standard non polar	33892256
Benomyl	CCCCN=C(O)N1C(N=C(O)OC)=NC2=CC=CC=C12	2597.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Benomyl,1TMS,isomer #1	CCCCN=C(O[Si](C)(C)C)N1C(N=C(O)OC)=NC2=CC=CC=C21	2398.9	Semi standard non polar	33892256
Benomyl,1TMS,isomer #2	CCCCN=C(O)N1C(N=C(OC)O[Si](C)(C)C)=NC2=CC=CC=C21	2375.4	Semi standard non polar	33892256
Benomyl,2TMS,isomer #1	CCCCN=C(O[Si](C)(C)C)N1C(N=C(OC)O[Si](C)(C)C)=NC2=CC=CC=C21	2365.9	Semi standard non polar	33892256
Benomyl,1TBDMS,isomer #1	CCCCN=C(O[Si](C)(C)C(C)(C)C)N1C(N=C(O)OC)=NC2=CC=CC=C21	2596.3	Semi standard non polar	33892256
Benomyl,1TBDMS,isomer #2	CCCCN=C(O)N1C(N=C(OC)O[Si](C)(C)C(C)(C)C)=NC2=CC=CC=C21	2596.6	Semi standard non polar	33892256
Benomyl,2TBDMS,isomer #1	CCCCN=C(O[Si](C)(C)C(C)(C)C)N1C(N=C(OC)O[Si](C)(C)C(C)(C)C)=NC2=CC=CC=C21	2728.2	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Benomyl GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-8890000000-e030c9d552fc5c7d52da	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Benomyl GC-MS (2 TMS) - 70eV, Positive	splash10-044i-9055500000-3eca627722374bbbc14c	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Benomyl GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-052f-7900000000-930ea348a291d67fe037	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benomyl 10V, Positive-QTOF	splash10-0006-2790000000-f3ed3b88d515aed07a44	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benomyl 20V, Positive-QTOF	splash10-01qc-1900000000-97b4102ec19aeb0c6974	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benomyl 40V, Positive-QTOF	splash10-001i-2900000000-1aa81e2473687dd33506	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benomyl 10V, Negative-QTOF	splash10-0a4l-2930000000-e8acc050770f45adf536	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benomyl 20V, Negative-QTOF	splash10-0a4l-4960000000-e995e6dd540486a3ceb2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benomyl 40V, Negative-QTOF	splash10-05ai-1900000000-c2b1949df8a55a1f654a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benomyl 10V, Positive-QTOF	splash10-0006-0910000000-66be9480198a5327e735	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benomyl 20V, Positive-QTOF	splash10-03di-0900000000-0c18c5b071a4b09c0c8e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benomyl 40V, Positive-QTOF	splash10-03di-2910000000-cd123ee8bdd6c595e223	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benomyl 10V, Negative-QTOF	splash10-0a4i-4980000000-13f898af5a45ad5b3402	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benomyl 20V, Negative-QTOF	splash10-0cdi-1940000000-70fa20da8fb0758e3219	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benomyl 40V, Negative-QTOF	splash10-0536-6910000000-3b461f008e97c4b1b708	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

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

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB008440

KNApSAcK ID

Not Available

Chemspider ID

26771

KEGG Compound ID

C10896

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Benomyl

METLIN ID

Not Available

PubChem Compound

28780

PDB ID

Not Available

ChEBI ID

3015

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

Edlind TD, Bartlett MS, Smith JW: Characterization of the beta-tubulin gene of Pneumocystis carinii. J Protozool. 1991 Nov-Dec;38(6):62S-63S. [PubMed:1818208 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Benomyl (HMDB0031767)

MOL for HMDB0031767 (Benomyl)

3D MOL for HMDB0031767 (Benomyl)

3D SDF for HMDB0031767 (Benomyl)

3D-SDF for HMDB0031767 (Benomyl)

PDB for HMDB0031767 (Benomyl)

3D PDB for HMDB0031767 (Benomyl)

SMILES for HMDB0031767 (Benomyl)

INCHI for HMDB0031767 (Benomyl)

Structure for HMDB0031767 (Benomyl)

3D Structure for HMDB0031767 (Benomyl)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra