Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 07:14:03 UTC

Update Date

2021-09-26 23:01:35 UTC

HMDB ID

HMDB0250250

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Cimetidine sulfoxide

Description

cimetidine S-oxide 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. Based on a literature review very few articles have been published on cimetidine S-oxide. This compound has been identified in human blood as reported by (PMID: 31557052 ). Cimetidine sulfoxide is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Cimetidine sulfoxide 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

HMDB0250250
     RDKit          3D
Cimetidine sulfoxide
 34 34  0  0  0  0  0  0  0  0999 V2000
   -5.0332    1.0126   -0.0664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4404   -0.2689   -0.3668 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3470   -0.6067    0.2200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7779   -1.8958   -0.1012 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5456   -2.1834   -1.4441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3724   -2.4281   -2.5628 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7424    0.2710    1.1440 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3141    0.5149    1.1167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0001    1.2749   -0.1503 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7714    1.5921   -0.2079 S   0  0  0  0  0  4  0  0  0  0  0  0
    1.1239    2.3892    1.0653 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6283    0.0362   -0.1951 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1146    0.2146   -0.2408 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7884    1.3607   -0.2905 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1158    1.1340   -0.3228 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2596   -0.2102   -0.2908 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0417   -0.8082   -0.2393 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7832   -2.2748   -0.1890 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2262    1.7802   -0.0912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8479    1.2985   -0.7358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4167    1.0337    0.9949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5821   -2.5212    0.6972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2966    0.7764    1.8827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8178   -0.4562    1.1003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9807    1.0565    2.0209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6049    2.1799   -0.2658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2714    0.6069   -1.0069 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3654   -0.5577    0.7214 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2697   -0.5694   -1.0577 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2960    2.3061   -0.3012 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8903    1.8938   -0.3670 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4801   -2.7308    0.5581 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7652   -2.4690    0.1515 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9235   -2.7519   -1.1794 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  3
  3  4  1  0
  4  5  1  0
  5  6  3  0
  3  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 13  2  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  0
  7 23  1  0
  8 24  1  0
  8 25  1  0
  9 26  1  0
  9 27  1  0
 12 28  1  0
 12 29  1  0
 14 30  1  0
 15 31  1  0
 18 32  1  0
 18 33  1  0
 18 34  1  0
M  END

  Mrv1652306031609452D          

 18 18  0  0  0  0            999 V2000
    0.8519    0.0795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8974    0.2146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1830    1.4521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4685    1.8646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0396    1.8646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3264    2.6896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9806    1.1745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2389    0.6316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3251    1.4521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6119    1.4521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3264    3.5146    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6119    0.6271    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8974    1.8646    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3264    1.8646    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5681    0.4601    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4286    1.7876    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7540    0.6271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7540    1.4521    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0  0  0  0
  8  1  1  0  0  0  0
  9  5  1  0  0  0  0
  9  8  2  0  0  0  0
 11  6  3  0  0  0  0
 12  2  1  4  0  0  0
 12 10  2  0  0  0  0
 13  3  1  0  0  0  0
 13 10  1  0  0  0  0
 14  6  1  0  0  0  0
 14 10  1  0  0  0  0
 15  7  2  0  0  0  0
 15  8  1  0  0  0  0
 16  7  1  0  0  0  0
 16  9  1  0  0  0  0
 18  4  1  0  0  0  0
 18  5  1  0  0  0  0
 18 17  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0250250

> <DATABASE_NAME>
hmdb

> <SMILES>
CN=C(NCCS(=O)CC1=C(C)N=CN1)NC#N

> <INCHI_IDENTIFIER>
InChI=1S/C10H16N6OS/c1-8-9(16-7-15-8)5-18(17)4-3-13-10(12-2)14-6-11/h7H,3-5H2,1-2H3,(H,15,16)(H2,12,13,14)

> <INCHI_KEY>
HOJLJLYVNQFCRE-UHFFFAOYSA-N

> <FORMULA>
C10H16N6OS

> <MOLECULAR_WEIGHT>
268.34

> <EXACT_MASS>
268.110630333

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
26.98312421574092

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-cyano-N''-methyl-N'-{2-[(4-methyl-1H-imidazol-5-yl)methanesulfinyl]ethyl}guanidine

> <ALOGPS_LOGP>
-0.33

> <JCHEM_LOGP>
-2.095065423666667

> <ALOGPS_LOGS>
-2.28

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.7727885450729

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.220640698799908

> <JCHEM_PKA_STRONGEST_BASIC>
6.560625927658181

> <JCHEM_POLAR_SURFACE_AREA>
105.95999999999998

> <JCHEM_REFRACTIVITY>
71.80669999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.40e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-cyano-N''-methyl-N'-{2-[(5-methyl-3H-imidazol-4-yl)methanesulfinyl]ethyl}guanidine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0250250
     RDKit          3D
Cimetidine sulfoxide
 34 34  0  0  0  0  0  0  0  0999 V2000
   -5.0332    1.0126   -0.0664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4404   -0.2689   -0.3668 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3470   -0.6067    0.2200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7779   -1.8958   -0.1012 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5456   -2.1834   -1.4441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3724   -2.4281   -2.5628 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7424    0.2710    1.1440 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3141    0.5149    1.1167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0001    1.2749   -0.1503 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7714    1.5921   -0.2079 S   0  0  0  0  0  4  0  0  0  0  0  0
    1.1239    2.3892    1.0653 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6283    0.0362   -0.1951 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1146    0.2146   -0.2408 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7884    1.3607   -0.2905 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1158    1.1340   -0.3228 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2596   -0.2102   -0.2908 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0417   -0.8082   -0.2393 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7832   -2.2748   -0.1890 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2262    1.7802   -0.0912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8479    1.2985   -0.7358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4167    1.0337    0.9949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5821   -2.5212    0.6972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2966    0.7764    1.8827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8178   -0.4562    1.1003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9807    1.0565    2.0209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6049    2.1799   -0.2658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2714    0.6069   -1.0069 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3654   -0.5577    0.7214 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2697   -0.5694   -1.0577 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2960    2.3061   -0.3012 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8903    1.8938   -0.3670 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4801   -2.7308    0.5581 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7652   -2.4690    0.1515 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9235   -2.7519   -1.1794 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  3
  3  4  1  0
  4  5  1  0
  5  6  3  0
  3  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 13  2  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  0
  7 23  1  0
  8 24  1  0
  8 25  1  0
  9 26  1  0
  9 27  1  0
 12 28  1  0
 12 29  1  0
 14 30  1  0
 15 31  1  0
 18 32  1  0
 18 33  1  0
 18 34  1  0
M  END

HEADER    PROTEIN                                 03-JUN-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-JUN-16         0                                  
HETATM    1  C   UNK     0       1.590   0.148   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.275   0.401   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.942   2.711   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.608   3.481   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.941   3.481   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.943   5.021   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.830   2.192   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.446   1.179   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.607   2.711   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.609   2.711   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       9.943   6.561   0.000  0.00  0.00           N+0
HETATM   12  N   UNK     0       8.609   1.171   0.000  0.00  0.00           N+0
HETATM   13  N   UNK     0       7.275   3.481   0.000  0.00  0.00           N+0
HETATM   14  N   UNK     0       9.943   3.481   0.000  0.00  0.00           N+0
HETATM   15  N   UNK     0      -1.060   0.859   0.000  0.00  0.00           N+0
HETATM   16  N   UNK     0      -0.800   3.337   0.000  0.00  0.00           N+0
HETATM   17  O   UNK     0       3.274   1.171   0.000  0.00  0.00           O+0
HETATM   18  S   UNK     0       3.274   2.711   0.000  0.00  0.00           S+0
CONECT    1    8                                                            
CONECT    2   12                                                            
CONECT    3    4   13                                                       
CONECT    4    3   18                                                       
CONECT    5    9   18                                                       
CONECT    6   11   14                                                       
CONECT    7   15   16                                                       
CONECT    8    1    9   15                                                  
CONECT    9    5    8   16                                                  
CONECT   10   12   13   14                                                  
CONECT   11    6                                                            
CONECT   12    2   10                                                       
CONECT   13    3   10                                                       
CONECT   14    6   10                                                       
CONECT   15    7    8                                                       
CONECT   16    7    9                                                       
CONECT   17   18                                                            
CONECT   18    4    5   17                                                  
MASTER        0    0    0    0    0    0    0    0   18    0   36    0
END

COMPND    HMDB0250250
HETATM    1  C1  UNL     1      -5.033   1.013  -0.066  1.00  0.00           C  
HETATM    2  N1  UNL     1      -4.440  -0.269  -0.367  1.00  0.00           N  
HETATM    3  C2  UNL     1      -3.347  -0.607   0.220  1.00  0.00           C  
HETATM    4  N2  UNL     1      -2.778  -1.896  -0.101  1.00  0.00           N  
HETATM    5  C3  UNL     1      -2.546  -2.183  -1.444  1.00  0.00           C  
HETATM    6  N3  UNL     1      -2.372  -2.428  -2.563  1.00  0.00           N  
HETATM    7  N4  UNL     1      -2.742   0.271   1.144  1.00  0.00           N  
HETATM    8  C4  UNL     1      -1.314   0.515   1.117  1.00  0.00           C  
HETATM    9  C5  UNL     1      -1.000   1.275  -0.150  1.00  0.00           C  
HETATM   10  S1  UNL     1       0.771   1.592  -0.208  1.00  0.00           S  
HETATM   11  O1  UNL     1       1.124   2.389   1.065  1.00  0.00           O  
HETATM   12  C6  UNL     1       1.628   0.036  -0.195  1.00  0.00           C  
HETATM   13  C7  UNL     1       3.115   0.215  -0.241  1.00  0.00           C  
HETATM   14  N5  UNL     1       3.788   1.361  -0.291  1.00  0.00           N  
HETATM   15  C8  UNL     1       5.116   1.134  -0.323  1.00  0.00           C  
HETATM   16  N6  UNL     1       5.260  -0.210  -0.291  1.00  0.00           N  
HETATM   17  C9  UNL     1       4.042  -0.808  -0.239  1.00  0.00           C  
HETATM   18  C10 UNL     1       3.783  -2.275  -0.189  1.00  0.00           C  
HETATM   19  H1  UNL     1      -4.226   1.780  -0.091  1.00  0.00           H  
HETATM   20  H2  UNL     1      -5.848   1.298  -0.736  1.00  0.00           H  
HETATM   21  H3  UNL     1      -5.417   1.034   0.995  1.00  0.00           H  
HETATM   22  H4  UNL     1      -2.582  -2.521   0.697  1.00  0.00           H  
HETATM   23  H5  UNL     1      -3.297   0.776   1.883  1.00  0.00           H  
HETATM   24  H6  UNL     1      -0.818  -0.456   1.100  1.00  0.00           H  
HETATM   25  H7  UNL     1      -0.981   1.056   2.021  1.00  0.00           H  
HETATM   26  H8  UNL     1      -1.605   2.180  -0.266  1.00  0.00           H  
HETATM   27  H9  UNL     1      -1.271   0.607  -1.007  1.00  0.00           H  
HETATM   28  H10 UNL     1       1.365  -0.558   0.721  1.00  0.00           H  
HETATM   29  H11 UNL     1       1.270  -0.569  -1.058  1.00  0.00           H  
HETATM   30  H12 UNL     1       3.296   2.306  -0.301  1.00  0.00           H  
HETATM   31  H13 UNL     1       5.890   1.894  -0.367  1.00  0.00           H  
HETATM   32  H14 UNL     1       4.480  -2.731   0.558  1.00  0.00           H  
HETATM   33  H15 UNL     1       2.765  -2.469   0.151  1.00  0.00           H  
HETATM   34  H16 UNL     1       3.924  -2.752  -1.179  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3    3
CONECT    3    4    7
CONECT    4    5   22
CONECT    5    6    6    6
CONECT    7    8   23
CONECT    8    9   24   25
CONECT    9   10   26   27
CONECT   10   11   11   12
CONECT   12   13   28   29
CONECT   13   14   17   17
CONECT   14   15   30
CONECT   15   16   16   31
CONECT   16   17
CONECT   17   18
CONECT   18   32   33   34
END

HMDB0250250
     RDKit          3D
Cimetidine sulfoxide
 34 34  0  0  0  0  0  0  0  0999 V2000
   -5.0332    1.0126   -0.0664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4404   -0.2689   -0.3668 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3470   -0.6067    0.2200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7779   -1.8958   -0.1012 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5456   -2.1834   -1.4441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3724   -2.4281   -2.5628 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7424    0.2710    1.1440 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3141    0.5149    1.1167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0001    1.2749   -0.1503 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7714    1.5921   -0.2079 S   0  0  0  0  0  4  0  0  0  0  0  0
    1.1239    2.3892    1.0653 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6283    0.0362   -0.1951 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1146    0.2146   -0.2408 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7884    1.3607   -0.2905 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1158    1.1340   -0.3228 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2596   -0.2102   -0.2908 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0417   -0.8082   -0.2393 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7832   -2.2748   -0.1890 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2262    1.7802   -0.0912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8479    1.2985   -0.7358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4167    1.0337    0.9949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5821   -2.5212    0.6972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2966    0.7764    1.8827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8178   -0.4562    1.1003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9807    1.0565    2.0209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6049    2.1799   -0.2658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2714    0.6069   -1.0069 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3654   -0.5577    0.7214 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2697   -0.5694   -1.0577 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2960    2.3061   -0.3012 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8903    1.8938   -0.3670 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4801   -2.7308    0.5581 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7652   -2.4690    0.1515 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9235   -2.7519   -1.1794 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  3
  3  4  1  0
  4  5  1  0
  5  6  3  0
  3  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 13  2  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  0
  7 23  1  0
  8 24  1  0
  8 25  1  0
  9 26  1  0
  9 27  1  0
 12 28  1  0
 12 29  1  0
 14 30  1  0
 15 31  1  0
 18 32  1  0
 18 33  1  0
 18 34  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Cimetidine sulfoxide	ChEBI
Cimetidine sulphoxide	Generator
1-Cyano-2-methyl-3-(2-(((4-methyl-1H-imidazol-5-yl)methyl)sulfinyl)ethyl)guanidine	MeSH

Chemical Formula

C₁₀H₁₆N₆OS

Average Molecular Weight

268.34

Monoisotopic Molecular Weight

268.110630333

IUPAC Name

N-cyano-N''-methyl-N'-{2-[(4-methyl-1H-imidazol-5-yl)methanesulfinyl]ethyl}guanidine

Traditional Name

N-cyano-N''-methyl-N'-{2-[(5-methyl-3H-imidazol-4-yl)methanesulfinyl]ethyl}guanidine

CAS Registry Number

Not Available

SMILES

CN=C(NCCS(=O)CC1=C(C)N=CN1)NC#N

InChI Identifier

InChI=1S/C10H16N6OS/c1-8-9(16-7-15-8)5-18(17)4-3-13-10(12-2)14-6-11/h7H,3-5H2,1-2H3,(H,15,16)(H2,12,13,14)

InChI Key

HOJLJLYVNQFCRE-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

Imidazole
Heteroaromatic compound
Guanidine
Sulfoxide
Sulfinyl compound
Carboximidamide
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organosulfur compound
Organonitrogen compound
Imine
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

sulfoxide (CHEBI:30731 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	-0.33	ALOGPS
logP	-2.1	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	13.22	ChemAxon
pKa (Strongest Basic)	6.56	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	105.96 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	71.81 m³·mol⁻¹	ChemAxon
Polarizability	26.98 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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]+	154.28	30932474
DeepCCS	[M-H]-	151.922	30932474
DeepCCS	[M-2H]-	186.182	30932474
DeepCCS	[M+Na]+	162.158	30932474
AllCCS	[M+H]+	160.2	32859911
AllCCS	[M+H-H2O]+	157.1	32859911
AllCCS	[M+NH4]+	163.1	32859911
AllCCS	[M+Na]+	164.0	32859911
AllCCS	[M-H]-	159.1	32859911
AllCCS	[M+Na-2H]-	159.6	32859911
AllCCS	[M+HCOO]-	160.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Cimetidine sulfoxide	CN=C(NCCS(=O)CC1=C(C)N=CN1)NC#N	3672.3	Standard polar	33892256
Cimetidine sulfoxide	CN=C(NCCS(=O)CC1=C(C)N=CN1)NC#N	2615.4	Standard non polar	33892256
Cimetidine sulfoxide	CN=C(NCCS(=O)CC1=C(C)N=CN1)NC#N	2968.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Cimetidine sulfoxide,1TMS,isomer #1	CN=C(NC#N)N(CCS(=O)CC1=C(C)N=C[NH]1)[Si](C)(C)C	2840.9	Semi standard non polar	33892256
Cimetidine sulfoxide,1TMS,isomer #1	CN=C(NC#N)N(CCS(=O)CC1=C(C)N=C[NH]1)[Si](C)(C)C	2535.6	Standard non polar	33892256
Cimetidine sulfoxide,1TMS,isomer #1	CN=C(NC#N)N(CCS(=O)CC1=C(C)N=C[NH]1)[Si](C)(C)C	4473.2	Standard polar	33892256
Cimetidine sulfoxide,1TMS,isomer #2	CN=C(NC#N)NCCS(=O)CC1=C(C)N=CN1[Si](C)(C)C	2835.9	Semi standard non polar	33892256
Cimetidine sulfoxide,1TMS,isomer #2	CN=C(NC#N)NCCS(=O)CC1=C(C)N=CN1[Si](C)(C)C	2754.0	Standard non polar	33892256
Cimetidine sulfoxide,1TMS,isomer #2	CN=C(NC#N)NCCS(=O)CC1=C(C)N=CN1[Si](C)(C)C	4694.8	Standard polar	33892256
Cimetidine sulfoxide,1TMS,isomer #3	CN=C(NCCS(=O)CC1=C(C)N=C[NH]1)N(C#N)[Si](C)(C)C	2786.5	Semi standard non polar	33892256
Cimetidine sulfoxide,1TMS,isomer #3	CN=C(NCCS(=O)CC1=C(C)N=C[NH]1)N(C#N)[Si](C)(C)C	2622.1	Standard non polar	33892256
Cimetidine sulfoxide,1TMS,isomer #3	CN=C(NCCS(=O)CC1=C(C)N=C[NH]1)N(C#N)[Si](C)(C)C	4254.4	Standard polar	33892256
Cimetidine sulfoxide,2TMS,isomer #1	CN=C(N(C#N)[Si](C)(C)C)N(CCS(=O)CC1=C(C)N=C[NH]1)[Si](C)(C)C	2673.2	Semi standard non polar	33892256
Cimetidine sulfoxide,2TMS,isomer #1	CN=C(N(C#N)[Si](C)(C)C)N(CCS(=O)CC1=C(C)N=C[NH]1)[Si](C)(C)C	2581.1	Standard non polar	33892256
Cimetidine sulfoxide,2TMS,isomer #1	CN=C(N(C#N)[Si](C)(C)C)N(CCS(=O)CC1=C(C)N=C[NH]1)[Si](C)(C)C	3966.6	Standard polar	33892256
Cimetidine sulfoxide,2TMS,isomer #2	CN=C(NC#N)N(CCS(=O)CC1=C(C)N=CN1[Si](C)(C)C)[Si](C)(C)C	2806.7	Semi standard non polar	33892256
Cimetidine sulfoxide,2TMS,isomer #2	CN=C(NC#N)N(CCS(=O)CC1=C(C)N=CN1[Si](C)(C)C)[Si](C)(C)C	2678.7	Standard non polar	33892256
Cimetidine sulfoxide,2TMS,isomer #2	CN=C(NC#N)N(CCS(=O)CC1=C(C)N=CN1[Si](C)(C)C)[Si](C)(C)C	4321.2	Standard polar	33892256
Cimetidine sulfoxide,2TMS,isomer #3	CN=C(NCCS(=O)CC1=C(C)N=CN1[Si](C)(C)C)N(C#N)[Si](C)(C)C	2754.7	Semi standard non polar	33892256
Cimetidine sulfoxide,2TMS,isomer #3	CN=C(NCCS(=O)CC1=C(C)N=CN1[Si](C)(C)C)N(C#N)[Si](C)(C)C	2801.7	Standard non polar	33892256
Cimetidine sulfoxide,2TMS,isomer #3	CN=C(NCCS(=O)CC1=C(C)N=CN1[Si](C)(C)C)N(C#N)[Si](C)(C)C	4137.7	Standard polar	33892256
Cimetidine sulfoxide,3TMS,isomer #1	CN=C(N(C#N)[Si](C)(C)C)N(CCS(=O)CC1=C(C)N=CN1[Si](C)(C)C)[Si](C)(C)C	2709.7	Semi standard non polar	33892256
Cimetidine sulfoxide,3TMS,isomer #1	CN=C(N(C#N)[Si](C)(C)C)N(CCS(=O)CC1=C(C)N=CN1[Si](C)(C)C)[Si](C)(C)C	2737.9	Standard non polar	33892256
Cimetidine sulfoxide,3TMS,isomer #1	CN=C(N(C#N)[Si](C)(C)C)N(CCS(=O)CC1=C(C)N=CN1[Si](C)(C)C)[Si](C)(C)C	3773.7	Standard polar	33892256
Cimetidine sulfoxide,1TBDMS,isomer #1	CN=C(NC#N)N(CCS(=O)CC1=C(C)N=C[NH]1)[Si](C)(C)C(C)(C)C	3045.9	Semi standard non polar	33892256
Cimetidine sulfoxide,1TBDMS,isomer #1	CN=C(NC#N)N(CCS(=O)CC1=C(C)N=C[NH]1)[Si](C)(C)C(C)(C)C	2752.6	Standard non polar	33892256
Cimetidine sulfoxide,1TBDMS,isomer #1	CN=C(NC#N)N(CCS(=O)CC1=C(C)N=C[NH]1)[Si](C)(C)C(C)(C)C	4451.9	Standard polar	33892256
Cimetidine sulfoxide,1TBDMS,isomer #2	CN=C(NC#N)NCCS(=O)CC1=C(C)N=CN1[Si](C)(C)C(C)(C)C	3072.1	Semi standard non polar	33892256
Cimetidine sulfoxide,1TBDMS,isomer #2	CN=C(NC#N)NCCS(=O)CC1=C(C)N=CN1[Si](C)(C)C(C)(C)C	2984.6	Standard non polar	33892256
Cimetidine sulfoxide,1TBDMS,isomer #2	CN=C(NC#N)NCCS(=O)CC1=C(C)N=CN1[Si](C)(C)C(C)(C)C	4687.3	Standard polar	33892256
Cimetidine sulfoxide,1TBDMS,isomer #3	CN=C(NCCS(=O)CC1=C(C)N=C[NH]1)N(C#N)[Si](C)(C)C(C)(C)C	3007.7	Semi standard non polar	33892256
Cimetidine sulfoxide,1TBDMS,isomer #3	CN=C(NCCS(=O)CC1=C(C)N=C[NH]1)N(C#N)[Si](C)(C)C(C)(C)C	2856.9	Standard non polar	33892256
Cimetidine sulfoxide,1TBDMS,isomer #3	CN=C(NCCS(=O)CC1=C(C)N=C[NH]1)N(C#N)[Si](C)(C)C(C)(C)C	4222.8	Standard polar	33892256
Cimetidine sulfoxide,2TBDMS,isomer #1	CN=C(N(C#N)[Si](C)(C)C(C)(C)C)N(CCS(=O)CC1=C(C)N=C[NH]1)[Si](C)(C)C(C)(C)C	3074.3	Semi standard non polar	33892256
Cimetidine sulfoxide,2TBDMS,isomer #1	CN=C(N(C#N)[Si](C)(C)C(C)(C)C)N(CCS(=O)CC1=C(C)N=C[NH]1)[Si](C)(C)C(C)(C)C	2974.9	Standard non polar	33892256
Cimetidine sulfoxide,2TBDMS,isomer #1	CN=C(N(C#N)[Si](C)(C)C(C)(C)C)N(CCS(=O)CC1=C(C)N=C[NH]1)[Si](C)(C)C(C)(C)C	3910.1	Standard polar	33892256
Cimetidine sulfoxide,2TBDMS,isomer #2	CN=C(NC#N)N(CCS(=O)CC1=C(C)N=CN1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3227.5	Semi standard non polar	33892256
Cimetidine sulfoxide,2TBDMS,isomer #2	CN=C(NC#N)N(CCS(=O)CC1=C(C)N=CN1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3112.9	Standard non polar	33892256
Cimetidine sulfoxide,2TBDMS,isomer #2	CN=C(NC#N)N(CCS(=O)CC1=C(C)N=CN1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	4293.7	Standard polar	33892256
Cimetidine sulfoxide,2TBDMS,isomer #3	CN=C(NCCS(=O)CC1=C(C)N=CN1[Si](C)(C)C(C)(C)C)N(C#N)[Si](C)(C)C(C)(C)C	3180.6	Semi standard non polar	33892256
Cimetidine sulfoxide,2TBDMS,isomer #3	CN=C(NCCS(=O)CC1=C(C)N=CN1[Si](C)(C)C(C)(C)C)N(C#N)[Si](C)(C)C(C)(C)C	3249.3	Standard non polar	33892256
Cimetidine sulfoxide,2TBDMS,isomer #3	CN=C(NCCS(=O)CC1=C(C)N=CN1[Si](C)(C)C(C)(C)C)N(C#N)[Si](C)(C)C(C)(C)C	4091.8	Standard polar	33892256
Cimetidine sulfoxide,3TBDMS,isomer #1	CN=C(N(C#N)[Si](C)(C)C(C)(C)C)N(CCS(=O)CC1=C(C)N=CN1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3293.4	Semi standard non polar	33892256
Cimetidine sulfoxide,3TBDMS,isomer #1	CN=C(N(C#N)[Si](C)(C)C(C)(C)C)N(CCS(=O)CC1=C(C)N=CN1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3320.0	Standard non polar	33892256
Cimetidine sulfoxide,3TBDMS,isomer #1	CN=C(N(C#N)[Si](C)(C)C(C)(C)C)N(CCS(=O)CC1=C(C)N=CN1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3779.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Cimetidine sulfoxide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-9400000000-73284a865bbf190abe02	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cimetidine sulfoxide 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 - Cimetidine sulfoxide 10V, Positive-QTOF	splash10-014i-3490000000-d307451b35c885c7f411	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cimetidine sulfoxide 20V, Positive-QTOF	splash10-00ov-9650000000-dbd85a59125d77a8db0c	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cimetidine sulfoxide 40V, Positive-QTOF	splash10-0002-9000000000-9760af8dc9453f7ef519	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cimetidine sulfoxide 10V, Negative-QTOF	splash10-014m-6690000000-fe801c80083157f91855	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cimetidine sulfoxide 20V, Negative-QTOF	splash10-006y-9750000000-84664508be907c90b42f	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cimetidine sulfoxide 40V, Negative-QTOF	splash10-0006-9100000000-a86608834851347a6736	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cimetidine sulfoxide 10V, Positive-QTOF	splash10-014i-0090000000-5732ba40f75de51b29d3	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cimetidine sulfoxide 20V, Positive-QTOF	splash10-00os-6920000000-f8a19c97b053151d1dc5	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cimetidine sulfoxide 40V, Positive-QTOF	splash10-0002-9000000000-5a4f36cc7cdcffde311c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cimetidine sulfoxide 10V, Negative-QTOF	splash10-00xu-2930000000-3acc0991485b5a4f2033	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cimetidine sulfoxide 20V, Negative-QTOF	splash10-014l-9000000000-035cb5d325b7441bea2d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cimetidine sulfoxide 40V, Negative-QTOF	splash10-0006-9200000000-31944d2513b827a918e9	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

56665

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

62949

PDB ID

Not Available

ChEBI ID

30731

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 Cimetidine sulfoxide (HMDB0250250)

MOL for HMDB0250250 (Cimetidine sulfoxide)

3D MOL for HMDB0250250 (Cimetidine sulfoxide)

3D SDF for HMDB0250250 (Cimetidine sulfoxide)

3D-SDF for HMDB0250250 (Cimetidine sulfoxide)

PDB for HMDB0250250 (Cimetidine sulfoxide)

3D PDB for HMDB0250250 (Cimetidine sulfoxide)

SMILES for HMDB0250250 (Cimetidine sulfoxide)

INCHI for HMDB0250250 (Cimetidine sulfoxide)

Structure for HMDB0250250 (Cimetidine sulfoxide)

3D Structure for HMDB0250250 (Cimetidine sulfoxide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra