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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2014-06-23 11:34:47 UTC

Update Date

2019-07-23 07:17:04 UTC

HMDB ID

HMDB0061722

Secondary Accession Numbers

HMDB61722

Metabolite Identification

Common Name

Metiamide

Description

Metiamide, also known as SK and F92058 or sk&f 92058, belongs to the class of organic compounds known as imidazoles. Imidazoles are compounds containing an imidazole ring, which is an aromatic five-member ring with two nitrogen atoms at positions 1 and 3, and three carbon atoms. Metiamide is a very strong basic compound (based on its pKa). Metiamide is a histamine H2-receptor antagonist. In humans, metiamide is involved in the metabolic disorder called the metiamide action pathway. This competitive inhibition results in reduced gastric acid secretion and a reduction in gastric volume and acidity. Other actions of Metiamide include an increase in gastric bacterial flora such as nitrate-reducing organisms. It was an intermediate product on the path to developing cimetidine. Metiamide is an H-2 receptor antagonist derived from burimamide. Metiamide inhibits many of the isoenzymes of the hepatic CYP450 enzyme system. Metiamide binds to an H2-receptor located on the basolateral membrane of the gastric parietal cell, blocking histamine effects. It reduces basal and nocturnal gastric acid secretion and a reduction in gastric volume, acidity, and amount of gastric acid released in response to stimuli including food, caffeine, insulin, betazole, or pentagastrin.

Structure

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

HMDB0061722
     RDKit          3D
Metiamide
 31 31  0  0  0  0  0  0  0  0999 V2000
   -6.4367   -0.0822   -0.6051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0495   -0.4951   -0.7458 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0175    0.1215    0.0061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3993    1.3145    1.0454 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6661   -0.2699   -0.1213 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6574    0.3777    0.6537 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2738   -0.1354    0.4221 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2885    0.0321   -1.2750 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.9767   -0.6185   -1.3717 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9222    0.2304   -0.5847 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6019    1.3315    0.1093 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7236    1.8101    0.6757 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7569    1.0106    0.3400 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2634    0.0343   -0.4385 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0817   -1.0670   -1.0273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0537   -0.5118   -1.4002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8328   -0.2970    0.4178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4713    1.0275   -0.7052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7913   -1.2562   -1.4072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4432   -1.0480   -0.8032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8938    0.1659    1.7369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7343    1.4829    0.5638 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4234    0.4228    1.0678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2229   -1.2007    0.7153 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0509   -1.6529   -1.0235 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3347   -0.5981   -2.4214 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8513    2.6826    1.3055 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7691    1.1399    0.6418 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1558   -0.8208   -0.9574 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8334   -1.1368   -2.0981 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9100   -1.9939   -0.4585 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  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 10  2  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  5 20  1  0
  6 21  1  0
  6 22  1  0
  7 23  1  0
  7 24  1  0
  9 25  1  0
  9 26  1  0
 12 27  1  0
 13 28  1  0
 15 29  1  0
 15 30  1  0
 15 31  1  0
M  END

1548992
  Mrv0541 02241214202D          

 15 15  0  0  0  0            999 V2000
    2.8795   -0.5306    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.3577    2.3980    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.3176   -3.2215    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5138    1.5580    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9050   -1.9518    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6631    2.9792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7301   -1.9518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2150   -1.2843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3644    0.1369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9850   -2.7365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0288    0.8906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7697   -2.9915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6501   -2.7365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1782    2.3118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3276    3.7329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  8  1  0  0  0  0
  1  9  1  0  0  0  0
  2 14  2  0  0  0  0
  3 10  1  0  0  0  0
  3 13  1  0  0  0  0
  4 11  1  0  0  0  0
  4 14  1  0  0  0  0
  5  7  1  0  0  0  0
  5 13  2  0  0  0  0
  6 14  1  0  0  0  0
  6 15  1  0  0  0  0
  7  8  1  0  0  0  0
  7 10  2  0  0  0  0
  9 11  1  0  0  0  0
 10 12  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0061722

> <DATABASE_NAME>
hmdb

> <SMILES>
CNC(=S)NCCSCC1=C(C)NC=N1

> <INCHI_IDENTIFIER>
InChI=1S/C9H16N4S2/c1-7-8(13-6-12-7)5-15-4-3-11-9(14)10-2/h6H,3-5H2,1-2H3,(H,12,13)(H2,10,11,14)

> <INCHI_KEY>
FPBPLBWLMYGIQR-UHFFFAOYSA-N

> <FORMULA>
C9H16N4S2

> <MOLECULAR_WEIGHT>
244.38

> <EXACT_MASS>
244.081637912

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
27.1875666833963

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-methyl-1-(2-{[(5-methyl-1H-imidazol-4-yl)methyl]sulfanyl}ethyl)thiourea

> <ALOGPS_LOGP>
0.50

> <JCHEM_LOGP>
0.3414594026666662

> <ALOGPS_LOGS>
-3.93

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.440358053337217

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.47847671161886

> <JCHEM_PKA_STRONGEST_BASIC>
6.911819779711405

> <JCHEM_POLAR_SURFACE_AREA>
52.74

> <JCHEM_REFRACTIVITY>
70.39529999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.87e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methiamide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0061722
     RDKit          3D
Metiamide
 31 31  0  0  0  0  0  0  0  0999 V2000
   -6.4367   -0.0822   -0.6051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0495   -0.4951   -0.7458 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0175    0.1215    0.0061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3993    1.3145    1.0454 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6661   -0.2699   -0.1213 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6574    0.3777    0.6537 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2738   -0.1354    0.4221 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2885    0.0321   -1.2750 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.9767   -0.6185   -1.3717 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9222    0.2304   -0.5847 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6019    1.3315    0.1093 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7236    1.8101    0.6757 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7569    1.0106    0.3400 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2634    0.0343   -0.4385 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0817   -1.0670   -1.0273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0537   -0.5118   -1.4002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8328   -0.2970    0.4178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4713    1.0275   -0.7052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7913   -1.2562   -1.4072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4432   -1.0480   -0.8032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8938    0.1659    1.7369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7343    1.4829    0.5638 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4234    0.4228    1.0678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2229   -1.2007    0.7153 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0509   -1.6529   -1.0235 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3347   -0.5981   -2.4214 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8513    2.6826    1.3055 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7691    1.1399    0.6418 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1558   -0.8208   -0.9574 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8334   -1.1368   -2.0981 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9100   -1.9939   -0.4585 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  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 10  2  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  5 20  1  0
  6 21  1  0
  6 22  1  0
  7 23  1  0
  7 24  1  0
  9 25  1  0
  9 26  1  0
 12 27  1  0
 13 28  1  0
 15 29  1  0
 15 30  1  0
 15 31  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1548992                                           
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  S   UNK     0       5.375  -0.990   0.000  0.00  0.00           S+0
HETATM    2  S   UNK     0       4.401   4.476   0.000  0.00  0.00           S+0
HETATM    3  N   UNK     0       4.326  -6.013   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0       6.559   2.908   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0       3.556  -3.643   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0       6.838   5.561   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       5.096  -3.643   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.001  -2.397   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.280   0.256   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.572  -5.108   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.654   1.662   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.037  -5.584   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.080  -5.108   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.933   4.315   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.212   6.968   0.000  0.00  0.00           C+0
CONECT    1    8    9                                                       
CONECT    2   14                                                            
CONECT    3   10   13                                                       
CONECT    4   11   14                                                       
CONECT    5    7   13                                                       
CONECT    6   14   15                                                       
CONECT    7    5    8   10                                                  
CONECT    8    1    7                                                       
CONECT    9    1   11                                                       
CONECT   10    3    7   12                                                  
CONECT   11    4    9                                                       
CONECT   12   10                                                            
CONECT   13    3    5                                                       
CONECT   14    2    4    6                                                  
CONECT   15    6                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

COMPND    HMDB0061722
HETATM    1  C1  UNL     1      -6.437  -0.082  -0.605  1.00  0.00           C  
HETATM    2  N1  UNL     1      -5.050  -0.495  -0.746  1.00  0.00           N  
HETATM    3  C2  UNL     1      -4.017   0.121   0.006  1.00  0.00           C  
HETATM    4  S1  UNL     1      -4.399   1.315   1.045  1.00  0.00           S  
HETATM    5  N2  UNL     1      -2.666  -0.270  -0.121  1.00  0.00           N  
HETATM    6  C3  UNL     1      -1.657   0.378   0.654  1.00  0.00           C  
HETATM    7  C4  UNL     1      -0.274  -0.135   0.422  1.00  0.00           C  
HETATM    8  S2  UNL     1       0.288   0.032  -1.275  1.00  0.00           S  
HETATM    9  C5  UNL     1       1.977  -0.619  -1.372  1.00  0.00           C  
HETATM   10  C6  UNL     1       2.922   0.230  -0.585  1.00  0.00           C  
HETATM   11  N3  UNL     1       2.602   1.332   0.109  1.00  0.00           N  
HETATM   12  C7  UNL     1       3.724   1.810   0.676  1.00  0.00           C  
HETATM   13  N4  UNL     1       4.757   1.011   0.340  1.00  0.00           N  
HETATM   14  C8  UNL     1       4.263   0.034  -0.438  1.00  0.00           C  
HETATM   15  C9  UNL     1       5.082  -1.067  -1.027  1.00  0.00           C  
HETATM   16  H1  UNL     1      -7.054  -0.512  -1.400  1.00  0.00           H  
HETATM   17  H2  UNL     1      -6.833  -0.297   0.418  1.00  0.00           H  
HETATM   18  H3  UNL     1      -6.471   1.027  -0.705  1.00  0.00           H  
HETATM   19  H4  UNL     1      -4.791  -1.256  -1.407  1.00  0.00           H  
HETATM   20  H5  UNL     1      -2.443  -1.048  -0.803  1.00  0.00           H  
HETATM   21  H6  UNL     1      -1.894   0.166   1.737  1.00  0.00           H  
HETATM   22  H7  UNL     1      -1.734   1.483   0.564  1.00  0.00           H  
HETATM   23  H8  UNL     1       0.423   0.423   1.068  1.00  0.00           H  
HETATM   24  H9  UNL     1      -0.223  -1.201   0.715  1.00  0.00           H  
HETATM   25  H10 UNL     1       2.051  -1.653  -1.024  1.00  0.00           H  
HETATM   26  H11 UNL     1       2.335  -0.598  -2.421  1.00  0.00           H  
HETATM   27  H12 UNL     1       3.851   2.683   1.305  1.00  0.00           H  
HETATM   28  H13 UNL     1       5.769   1.140   0.642  1.00  0.00           H  
HETATM   29  H14 UNL     1       6.156  -0.821  -0.957  1.00  0.00           H  
HETATM   30  H15 UNL     1       4.833  -1.137  -2.098  1.00  0.00           H  
HETATM   31  H16 UNL     1       4.910  -1.994  -0.459  1.00  0.00           H  
CONECT    1    2   16   17   18
CONECT    2    3   19
CONECT    3    4    4    5
CONECT    5    6   20
CONECT    6    7   21   22
CONECT    7    8   23   24
CONECT    8    9
CONECT    9   10   25   26
CONECT   10   11   14   14
CONECT   11   12   12
CONECT   12   13   27
CONECT   13   14   28
CONECT   14   15
CONECT   15   29   30   31
END

HMDB0061722
     RDKit          3D
Metiamide
 31 31  0  0  0  0  0  0  0  0999 V2000
   -6.4367   -0.0822   -0.6051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0495   -0.4951   -0.7458 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0175    0.1215    0.0061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3993    1.3145    1.0454 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6661   -0.2699   -0.1213 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6574    0.3777    0.6537 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2738   -0.1354    0.4221 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2885    0.0321   -1.2750 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.9767   -0.6185   -1.3717 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9222    0.2304   -0.5847 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6019    1.3315    0.1093 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7236    1.8101    0.6757 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7569    1.0106    0.3400 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2634    0.0343   -0.4385 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0817   -1.0670   -1.0273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0537   -0.5118   -1.4002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8328   -0.2970    0.4178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4713    1.0275   -0.7052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7913   -1.2562   -1.4072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4432   -1.0480   -0.8032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8938    0.1659    1.7369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7343    1.4829    0.5638 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4234    0.4228    1.0678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2229   -1.2007    0.7153 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0509   -1.6529   -1.0235 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3347   -0.5981   -2.4214 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8513    2.6826    1.3055 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7691    1.1399    0.6418 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1558   -0.8208   -0.9574 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8334   -1.1368   -2.0981 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9100   -1.9939   -0.4585 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  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 10  2  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  5 20  1  0
  6 21  1  0
  6 22  1  0
  7 23  1  0
  7 24  1  0
  9 25  1  0
  9 26  1  0
 12 27  1  0
 13 28  1  0
 15 29  1  0
 15 30  1  0
 15 31  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
SK&F 92058	HMDB
Metiamide monohydrochloride	HMDB
SK And F92058	HMDB
Monohydrochloride, metiamide	HMDB
SK And F 92058	HMDB
SK And F-92058	HMDB

Chemical Formula

C₉H₁₆N₄S₂

Average Molecular Weight

244.38

Monoisotopic Molecular Weight

244.081637912

IUPAC Name

3-methyl-1-(2-{[(5-methyl-1H-imidazol-4-yl)methyl]sulfanyl}ethyl)thiourea

Traditional Name

methiamide

CAS Registry Number

Not Available

SMILES

CNC(=S)NCCSCC1=C(C)NC=N1

InChI Identifier

InChI=1S/C9H16N4S2/c1-7-8(13-6-12-7)5-15-4-3-11-9(14)10-2/h6H,3-5H2,1-2H3,(H,12,13)(H2,10,11,14)

InChI Key

FPBPLBWLMYGIQR-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as imidazoles. Imidazoles are compounds containing an imidazole ring, which is an aromatic five-member ring with two nitrogen atoms at positions 1 and 3, and three carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azoles

Sub Class

Imidazoles

Direct Parent

Imidazoles

Alternative Parents

Substituents

Heteroaromatic compound
Imidazole
Thiourea
Azacycle
Dialkylthioether
Sulfenyl compound
Thioether
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organosulfur compound
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

imidazoles (CHEBI:6896 )

Ontology

Not Available

Exogenous (HMDB: HMDB0061722)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Metiamide Action Pathway (PathBank: SMP0000735)

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
Water Solubility	0.029 g/L	ALOGPS
logP	0.5	ALOGPS
logP	0.34	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	12.48	ChemAxon
pKa (Strongest Basic)	6.91	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	52.74 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	70.4 m³·mol⁻¹	ChemAxon
Polarizability	27.19 Å³	ChemAxon
Number of Rings	1	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]+	154.661	31661259
DarkChem	[M-H]-	150.896	31661259
DeepCCS	[M+H]+	150.55	30932474
DeepCCS	[M-H]-	147.253	30932474
DeepCCS	[M-2H]-	184.24	30932474
DeepCCS	[M+Na]+	159.903	30932474
AllCCS	[M+H]+	152.3	32859911
AllCCS	[M+H-H2O]+	148.9	32859911
AllCCS	[M+NH4]+	155.5	32859911
AllCCS	[M+Na]+	156.4	32859911
AllCCS	[M-H]-	155.5	32859911
AllCCS	[M+Na-2H]-	156.5	32859911
AllCCS	[M+HCOO]-	157.6	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	2.94 minutes	32390414
Predicted by Siyang on May 30, 2022	8.8759 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.93 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	409.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	242.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	60.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	157.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	54.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	293.0 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	297.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	800.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	579.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	64.9 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	802.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	168.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	185.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	696.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	507.7 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	223.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Metiamide	CNC(=S)NCCSCC1=C(C)NC=N1	3595.9	Standard polar	33892256
Metiamide	CNC(=S)NCCSCC1=C(C)NC=N1	2234.9	Standard non polar	33892256
Metiamide	CNC(=S)NCCSCC1=C(C)NC=N1	2760.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Metiamide,1TMS,isomer #1	CC1=C(CSCCNC(=S)N(C)[Si](C)(C)C)N=C[NH]1	2508.8	Semi standard non polar	33892256
Metiamide,1TMS,isomer #1	CC1=C(CSCCNC(=S)N(C)[Si](C)(C)C)N=C[NH]1	2165.7	Standard non polar	33892256
Metiamide,1TMS,isomer #1	CC1=C(CSCCNC(=S)N(C)[Si](C)(C)C)N=C[NH]1	3460.1	Standard polar	33892256
Metiamide,1TMS,isomer #2	CNC(=S)N(CCSCC1=C(C)[NH]C=N1)[Si](C)(C)C	2465.3	Semi standard non polar	33892256
Metiamide,1TMS,isomer #2	CNC(=S)N(CCSCC1=C(C)[NH]C=N1)[Si](C)(C)C	2209.1	Standard non polar	33892256
Metiamide,1TMS,isomer #2	CNC(=S)N(CCSCC1=C(C)[NH]C=N1)[Si](C)(C)C	3495.5	Standard polar	33892256
Metiamide,1TMS,isomer #3	CNC(=S)NCCSCC1=C(C)N([Si](C)(C)C)C=N1	2590.0	Semi standard non polar	33892256
Metiamide,1TMS,isomer #3	CNC(=S)NCCSCC1=C(C)N([Si](C)(C)C)C=N1	2177.6	Standard non polar	33892256
Metiamide,1TMS,isomer #3	CNC(=S)NCCSCC1=C(C)N([Si](C)(C)C)C=N1	3897.2	Standard polar	33892256
Metiamide,2TMS,isomer #1	CC1=C(CSCCNC(=S)N(C)[Si](C)(C)C)N=CN1[Si](C)(C)C	2583.6	Semi standard non polar	33892256
Metiamide,2TMS,isomer #1	CC1=C(CSCCNC(=S)N(C)[Si](C)(C)C)N=CN1[Si](C)(C)C	2307.7	Standard non polar	33892256
Metiamide,2TMS,isomer #1	CC1=C(CSCCNC(=S)N(C)[Si](C)(C)C)N=CN1[Si](C)(C)C	3340.8	Standard polar	33892256
Metiamide,2TMS,isomer #2	CC1=C(CSCCN(C(=S)N(C)[Si](C)(C)C)[Si](C)(C)C)N=C[NH]1	2467.6	Semi standard non polar	33892256
Metiamide,2TMS,isomer #2	CC1=C(CSCCN(C(=S)N(C)[Si](C)(C)C)[Si](C)(C)C)N=C[NH]1	2288.6	Standard non polar	33892256
Metiamide,2TMS,isomer #2	CC1=C(CSCCN(C(=S)N(C)[Si](C)(C)C)[Si](C)(C)C)N=C[NH]1	3118.8	Standard polar	33892256
Metiamide,2TMS,isomer #3	CNC(=S)N(CCSCC1=C(C)N([Si](C)(C)C)C=N1)[Si](C)(C)C	2535.4	Semi standard non polar	33892256
Metiamide,2TMS,isomer #3	CNC(=S)N(CCSCC1=C(C)N([Si](C)(C)C)C=N1)[Si](C)(C)C	2349.4	Standard non polar	33892256
Metiamide,2TMS,isomer #3	CNC(=S)N(CCSCC1=C(C)N([Si](C)(C)C)C=N1)[Si](C)(C)C	3364.9	Standard polar	33892256
Metiamide,3TMS,isomer #1	CC1=C(CSCCN(C(=S)N(C)[Si](C)(C)C)[Si](C)(C)C)N=CN1[Si](C)(C)C	2502.2	Semi standard non polar	33892256
Metiamide,3TMS,isomer #1	CC1=C(CSCCN(C(=S)N(C)[Si](C)(C)C)[Si](C)(C)C)N=CN1[Si](C)(C)C	2417.4	Standard non polar	33892256
Metiamide,3TMS,isomer #1	CC1=C(CSCCN(C(=S)N(C)[Si](C)(C)C)[Si](C)(C)C)N=CN1[Si](C)(C)C	2948.2	Standard polar	33892256
Metiamide,1TBDMS,isomer #1	CC1=C(CSCCNC(=S)N(C)[Si](C)(C)C(C)(C)C)N=C[NH]1	2748.1	Semi standard non polar	33892256
Metiamide,1TBDMS,isomer #1	CC1=C(CSCCNC(=S)N(C)[Si](C)(C)C(C)(C)C)N=C[NH]1	2411.5	Standard non polar	33892256
Metiamide,1TBDMS,isomer #1	CC1=C(CSCCNC(=S)N(C)[Si](C)(C)C(C)(C)C)N=C[NH]1	3536.1	Standard polar	33892256
Metiamide,1TBDMS,isomer #2	CNC(=S)N(CCSCC1=C(C)[NH]C=N1)[Si](C)(C)C(C)(C)C	2701.3	Semi standard non polar	33892256
Metiamide,1TBDMS,isomer #2	CNC(=S)N(CCSCC1=C(C)[NH]C=N1)[Si](C)(C)C(C)(C)C	2433.5	Standard non polar	33892256
Metiamide,1TBDMS,isomer #2	CNC(=S)N(CCSCC1=C(C)[NH]C=N1)[Si](C)(C)C(C)(C)C	3538.7	Standard polar	33892256
Metiamide,1TBDMS,isomer #3	CNC(=S)NCCSCC1=C(C)N([Si](C)(C)C(C)(C)C)C=N1	2804.7	Semi standard non polar	33892256
Metiamide,1TBDMS,isomer #3	CNC(=S)NCCSCC1=C(C)N([Si](C)(C)C(C)(C)C)C=N1	2391.1	Standard non polar	33892256
Metiamide,1TBDMS,isomer #3	CNC(=S)NCCSCC1=C(C)N([Si](C)(C)C(C)(C)C)C=N1	3900.5	Standard polar	33892256
Metiamide,2TBDMS,isomer #1	CC1=C(CSCCNC(=S)N(C)[Si](C)(C)C(C)(C)C)N=CN1[Si](C)(C)C(C)(C)C	3016.9	Semi standard non polar	33892256
Metiamide,2TBDMS,isomer #1	CC1=C(CSCCNC(=S)N(C)[Si](C)(C)C(C)(C)C)N=CN1[Si](C)(C)C(C)(C)C	2736.7	Standard non polar	33892256
Metiamide,2TBDMS,isomer #1	CC1=C(CSCCNC(=S)N(C)[Si](C)(C)C(C)(C)C)N=CN1[Si](C)(C)C(C)(C)C	3397.8	Standard polar	33892256
Metiamide,2TBDMS,isomer #2	CC1=C(CSCCN(C(=S)N(C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=C[NH]1	2934.2	Semi standard non polar	33892256
Metiamide,2TBDMS,isomer #2	CC1=C(CSCCN(C(=S)N(C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=C[NH]1	2730.5	Standard non polar	33892256
Metiamide,2TBDMS,isomer #2	CC1=C(CSCCN(C(=S)N(C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=C[NH]1	3219.1	Standard polar	33892256
Metiamide,2TBDMS,isomer #3	CNC(=S)N(CCSCC1=C(C)N([Si](C)(C)C(C)(C)C)C=N1)[Si](C)(C)C(C)(C)C	2963.5	Semi standard non polar	33892256
Metiamide,2TBDMS,isomer #3	CNC(=S)N(CCSCC1=C(C)N([Si](C)(C)C(C)(C)C)C=N1)[Si](C)(C)C(C)(C)C	2756.2	Standard non polar	33892256
Metiamide,2TBDMS,isomer #3	CNC(=S)N(CCSCC1=C(C)N([Si](C)(C)C(C)(C)C)C=N1)[Si](C)(C)C(C)(C)C	3391.7	Standard polar	33892256
Metiamide,3TBDMS,isomer #1	CC1=C(CSCCN(C(=S)N(C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN1[Si](C)(C)C(C)(C)C	3219.7	Semi standard non polar	33892256
Metiamide,3TBDMS,isomer #1	CC1=C(CSCCN(C(=S)N(C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN1[Si](C)(C)C(C)(C)C	3016.1	Standard non polar	33892256
Metiamide,3TBDMS,isomer #1	CC1=C(CSCCN(C(=S)N(C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN1[Si](C)(C)C(C)(C)C	3149.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Metiamide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0005-9300000000-907f73f8f938674a5458	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Metiamide 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 - Metiamide 10V, Positive-QTOF	splash10-0002-7970000000-6270ca74d4ef8b47ab52	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metiamide 20V, Positive-QTOF	splash10-0092-9810000000-1cf11ce57b088bbc7944	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metiamide 40V, Positive-QTOF	splash10-00dm-9100000000-d640ef6b5070ab66edd5	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metiamide 10V, Negative-QTOF	splash10-002f-6960000000-9c8740cd4df559672784	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metiamide 20V, Negative-QTOF	splash10-00vi-8920000000-f302b9dcfb00f3db7477	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metiamide 40V, Negative-QTOF	splash10-006x-9100000000-716c4b942353dd80ae74	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metiamide 10V, Negative-QTOF	splash10-0006-1190000000-421f42ae40c1562bba18	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metiamide 20V, Negative-QTOF	splash10-014i-5900000000-d6b80ce1f1381c2803c0	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metiamide 40V, Negative-QTOF	splash10-00xr-9200000000-e805a0b1a704bafe9751	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metiamide 10V, Positive-QTOF	splash10-0002-1190000000-497de74916d0c5d97805	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metiamide 20V, Positive-QTOF	splash10-002b-9300000000-f932af11961ea77f716f	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metiamide 40V, Positive-QTOF	splash10-000t-9100000000-87be1cad0bd6e916dea5	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Metiamide Action Pathway		Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB08805

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C07449

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Metiamide

METLIN ID

Not Available

PubChem Compound

1548992

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

Not Available

Showing metabocard for Metiamide (HMDB0061722)

MOL for HMDB0061722 (Metiamide)

3D MOL for HMDB0061722 (Metiamide)

3D SDF for HMDB0061722 (Metiamide)

3D-SDF for HMDB0061722 (Metiamide)

PDB for HMDB0061722 (Metiamide)

3D PDB for HMDB0061722 (Metiamide)

SMILES for HMDB0061722 (Metiamide)

INCHI for HMDB0061722 (Metiamide)

Structure for HMDB0061722 (Metiamide)

3D Structure for HMDB0061722 (Metiamide)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra