Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (13)transporters (10) Show 23 proteins XML

enzymes (13)transporters (10) Show 23 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2022-03-07 02:51:41 UTC

HMDB ID

HMDB0014644

Secondary Accession Numbers

HMDB14644

Metabolite Identification

Common Name

Cimetidine

Description

Cimetidine, also known as tagamet HB 200 or SK and F92334, 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. Its plasma protein binding is 13 to 25% and is said to be without pharmacological significance. Cimetidine is a drug which is used for the treatment and the management of acid-reflux disorders (gerd), peptic ulcer disease, heartburn, and acid indigestion. Cimetidine is a very strong basic compound (based on its pKa). In humans, cimetidine is involved in cimetidine action pathway. Cimetidine is a potentially toxic compound.

Structure

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

HMDB0014644
     RDKit          3D
Cimetidine
 33 33  0  0  0  0  0  0  0  0999 V2000
    4.7989    1.8802    0.9820 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4828    1.2626    0.8788 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3231    0.0735    0.4479 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4956   -0.6351    0.0663 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7051   -1.9092    0.5725 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8634   -2.9580    1.0069 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0950   -0.6159    0.3036 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0660   -0.2239   -0.6286 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3811    1.0657   -0.2552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8880    1.5189   -1.4508 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2455    0.3444   -1.5365 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0311    0.2550   -0.3089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8723    0.9206    0.8387 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8251    0.5279    1.7299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5993   -0.4116    1.1123 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1108   -0.5735   -0.1304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6554   -1.5110   -1.1385 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3986    1.4622    1.8115 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4044    1.7528    0.0518 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6400    2.9658    1.1252 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1745   -0.1986   -0.5788 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8879   -1.4684    0.8971 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3174   -1.0323   -0.7720 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5479   -0.1140   -1.6471 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1488    1.8761   -0.2871 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0196    1.0321    0.7907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8699    0.6678   -2.4243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8239   -0.6351   -1.8670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9430    0.8917    2.7334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4158   -0.9025    1.5463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3397   -0.9565   -1.8369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2796   -2.3172   -0.6900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8510   -2.0349   -1.7026 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  3  0
  3  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 12  2  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  4 21  1  0
  7 22  1  0
  8 23  1  0
  8 24  1  0
  9 25  1  0
  9 26  1  0
 11 27  1  0
 11 28  1  0
 14 29  1  0
 15 30  1  0
 17 31  1  0
 17 32  1  0
 17 33  1  0
M  END

501
  Mrv1652305271900062D          

 17 17  0  0  0  0            999 V2000
    2.8795   -0.9075    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.3176   -3.5983    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5138    1.1812    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9050   -2.3287    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6631    2.6024    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3577    2.0211    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9920    4.1098    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7301   -2.3287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2150   -1.6612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3645   -0.2400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0288    0.5137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9850   -3.1133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7697   -3.3683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6501   -3.1133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1782    1.9349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0221    2.7749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3276    3.3561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  9  1  0  0  0  0
  1 10  1  0  0  0  0
  2 12  1  0  0  0  0
  2 14  1  0  0  0  0
  3 11  1  0  0  0  0
  3 15  1  0  0  0  0
  4  8  1  0  0  0  0
  4 14  2  0  0  0  0
  5 15  1  0  0  0  0
  5 17  1  0  0  0  0
  6 15  2  0  0  0  0
  6 16  1  0  0  0  0
  7 17  3  0  0  0  0
  8  9  1  0  0  0  0
  8 12  2  0  0  0  0
 10 11  1  0  0  0  0
 12 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014644

> <DATABASE_NAME>
hmdb

> <SMILES>
C\N=C(\NCCSCC1=C(C)NC=N1)NC#N

> <INCHI_IDENTIFIER>
InChI=1S/C10H16N6S/c1-8-9(16-7-15-8)5-17-4-3-13-10(12-2)14-6-11/h7H,3-5H2,1-2H3,(H,15,16)(H2,12,13,14)

> <INCHI_KEY>
AQIXAKUUQRKLND-UHFFFAOYSA-N

> <FORMULA>
C10H16N6S

> <MOLECULAR_WEIGHT>
252.339

> <EXACT_MASS>
252.115715232

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
27.473564589735226

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
0.44

> <JCHEM_LOGP>
-0.10935610666666695

> <ALOGPS_LOGS>
-2.49

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
19.97899291739049

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.382499342054437

> <JCHEM_PKA_STRONGEST_BASIC>
6.91391881185031

> <JCHEM_POLAR_SURFACE_AREA>
88.88999999999999

> <JCHEM_REFRACTIVITY>
70.3171

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.16e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
tagamet HB

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014644
     RDKit          3D
Cimetidine
 33 33  0  0  0  0  0  0  0  0999 V2000
    4.7989    1.8802    0.9820 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4828    1.2626    0.8788 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3231    0.0735    0.4479 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4956   -0.6351    0.0663 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7051   -1.9092    0.5725 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8634   -2.9580    1.0069 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0950   -0.6159    0.3036 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0660   -0.2239   -0.6286 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3811    1.0657   -0.2552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8880    1.5189   -1.4508 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2455    0.3444   -1.5365 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0311    0.2550   -0.3089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8723    0.9206    0.8387 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8251    0.5279    1.7299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5993   -0.4116    1.1123 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1108   -0.5735   -0.1304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6554   -1.5110   -1.1385 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3986    1.4622    1.8115 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4044    1.7528    0.0518 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6400    2.9658    1.1252 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1745   -0.1986   -0.5788 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8879   -1.4684    0.8971 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3174   -1.0323   -0.7720 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5479   -0.1140   -1.6471 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1488    1.8761   -0.2871 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0196    1.0321    0.7907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8699    0.6678   -2.4243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8239   -0.6351   -1.8670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9430    0.8917    2.7334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4158   -0.9025    1.5463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3397   -0.9565   -1.8369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2796   -2.3172   -0.6900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8510   -2.0349   -1.7026 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  3  0
  3  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 12  2  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  4 21  1  0
  7 22  1  0
  8 23  1  0
  8 24  1  0
  9 25  1  0
  9 26  1  0
 11 27  1  0
 11 28  1  0
 14 29  1  0
 15 30  1  0
 17 31  1  0
 17 32  1  0
 17 33  1  0
M  END

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 501                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  S   UNK     0       5.375  -1.694   0.000  0.00  0.00           S+0
HETATM    2  N   UNK     0       4.326  -6.717   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0       6.559   2.205   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0       3.556  -4.347   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0       6.838   4.858   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0       4.401   3.773   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0       5.585   7.672   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       5.096  -4.347   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.001  -3.101   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.280  -0.448   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.654   0.959   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.572  -5.811   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.037  -6.287   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.080  -5.811   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.933   3.612   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.775   5.180   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.212   6.265   0.000  0.00  0.00           C+0
CONECT    1    9   10                                                       
CONECT    2   12   14                                                       
CONECT    3   11   15                                                       
CONECT    4    8   14                                                       
CONECT    5   15   17                                                       
CONECT    6   15   16                                                       
CONECT    7   17                                                            
CONECT    8    4    9   12                                                  
CONECT    9    1    8                                                       
CONECT   10    1   11                                                       
CONECT   11    3   10                                                       
CONECT   12    2    8   13                                                  
CONECT   13   12                                                            
CONECT   14    2    4                                                       
CONECT   15    3    5    6                                                  
CONECT   16    6                                                            
CONECT   17    5    7                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   34    0
END

COMPND    HMDB0014644
HETATM    1  C1  UNL     1       4.799   1.880   0.982  1.00  0.00           C  
HETATM    2  N1  UNL     1       3.483   1.263   0.879  1.00  0.00           N  
HETATM    3  C2  UNL     1       3.323   0.074   0.448  1.00  0.00           C  
HETATM    4  N2  UNL     1       4.496  -0.635   0.066  1.00  0.00           N  
HETATM    5  C3  UNL     1       4.705  -1.909   0.573  1.00  0.00           C  
HETATM    6  N3  UNL     1       4.863  -2.958   1.007  1.00  0.00           N  
HETATM    7  N4  UNL     1       2.095  -0.616   0.304  1.00  0.00           N  
HETATM    8  C4  UNL     1       1.066  -0.224  -0.629  1.00  0.00           C  
HETATM    9  C5  UNL     1       0.381   1.066  -0.255  1.00  0.00           C  
HETATM   10  S1  UNL     1      -0.888   1.519  -1.451  1.00  0.00           S  
HETATM   11  C6  UNL     1      -2.245   0.344  -1.536  1.00  0.00           C  
HETATM   12  C7  UNL     1      -3.031   0.255  -0.309  1.00  0.00           C  
HETATM   13  N5  UNL     1      -2.872   0.921   0.839  1.00  0.00           N  
HETATM   14  C8  UNL     1      -3.825   0.528   1.730  1.00  0.00           C  
HETATM   15  N6  UNL     1      -4.599  -0.412   1.112  1.00  0.00           N  
HETATM   16  C9  UNL     1      -4.111  -0.574  -0.130  1.00  0.00           C  
HETATM   17  C10 UNL     1      -4.655  -1.511  -1.139  1.00  0.00           C  
HETATM   18  H1  UNL     1       5.399   1.462   1.812  1.00  0.00           H  
HETATM   19  H2  UNL     1       5.404   1.753   0.052  1.00  0.00           H  
HETATM   20  H3  UNL     1       4.640   2.966   1.125  1.00  0.00           H  
HETATM   21  H4  UNL     1       5.174  -0.199  -0.579  1.00  0.00           H  
HETATM   22  H5  UNL     1       1.888  -1.468   0.897  1.00  0.00           H  
HETATM   23  H6  UNL     1       0.317  -1.032  -0.772  1.00  0.00           H  
HETATM   24  H7  UNL     1       1.548  -0.114  -1.647  1.00  0.00           H  
HETATM   25  H8  UNL     1       1.149   1.876  -0.287  1.00  0.00           H  
HETATM   26  H9  UNL     1       0.020   1.032   0.791  1.00  0.00           H  
HETATM   27  H10 UNL     1      -2.870   0.668  -2.424  1.00  0.00           H  
HETATM   28  H11 UNL     1      -1.824  -0.635  -1.867  1.00  0.00           H  
HETATM   29  H12 UNL     1      -3.943   0.892   2.733  1.00  0.00           H  
HETATM   30  H13 UNL     1      -5.416  -0.902   1.546  1.00  0.00           H  
HETATM   31  H14 UNL     1      -5.340  -0.956  -1.837  1.00  0.00           H  
HETATM   32  H15 UNL     1      -5.280  -2.317  -0.690  1.00  0.00           H  
HETATM   33  H16 UNL     1      -3.851  -2.035  -1.703  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3    3
CONECT    3    4    7
CONECT    4    5   21
CONECT    5    6    6    6
CONECT    7    8   22
CONECT    8    9   23   24
CONECT    9   10   25   26
CONECT   10   11
CONECT   11   12   27   28
CONECT   12   13   16   16
CONECT   13   14   14
CONECT   14   15   29
CONECT   15   16   30
CONECT   16   17
CONECT   17   31   32   33
END

HMDB0014644
     RDKit          3D
Cimetidine
 33 33  0  0  0  0  0  0  0  0999 V2000
    4.7989    1.8802    0.9820 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4828    1.2626    0.8788 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3231    0.0735    0.4479 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4956   -0.6351    0.0663 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7051   -1.9092    0.5725 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8634   -2.9580    1.0069 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0950   -0.6159    0.3036 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0660   -0.2239   -0.6286 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3811    1.0657   -0.2552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8880    1.5189   -1.4508 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2455    0.3444   -1.5365 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0311    0.2550   -0.3089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8723    0.9206    0.8387 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8251    0.5279    1.7299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5993   -0.4116    1.1123 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1108   -0.5735   -0.1304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6554   -1.5110   -1.1385 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3986    1.4622    1.8115 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4044    1.7528    0.0518 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6400    2.9658    1.1252 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1745   -0.1986   -0.5788 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8879   -1.4684    0.8971 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3174   -1.0323   -0.7720 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5479   -0.1140   -1.6471 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1488    1.8761   -0.2871 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0196    1.0321    0.7907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8699    0.6678   -2.4243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8239   -0.6351   -1.8670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9430    0.8917    2.7334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4158   -0.9025    1.5463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3397   -0.9565   -1.8369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2796   -2.3172   -0.6900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8510   -2.0349   -1.7026 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  3  0
  3  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 12  2  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  4 21  1  0
  7 22  1  0
  8 23  1  0
  8 24  1  0
  9 25  1  0
  9 26  1  0
 11 27  1  0
 11 28  1  0
 14 29  1  0
 15 30  1  0
 17 31  1  0
 17 32  1  0
 17 33  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
1-Cyano-2-methyl-3-(2-(((5-methyl-4-imidazolyl)methyl)thio)ethyl)guanidine	ChEBI
2-Cyano-1-methyl-3-(2-(((5-methylimidazol-4-yl)methyl)thio)ethyl)guanidine	ChEBI
Cimetag	ChEBI
Cimetidina	ChEBI
Cimetidinum	ChEBI
N''-cyano-N-methyl-n'-(2-{[(5-methyl-1H-imidazol-4-yl)methyl]thio}ethyl)guanidine	ChEBI
N-Cyano-n'-methyl-n''-(2-([(5-methyl-1H-imidazol-4-yl)methyl]sulfanyl)ethyl)guanidine	ChEBI
Tagamet HB 200	ChEBI
Ulcerfen	ChEBI
Tagamet	Kegg
N-Cyano-n'-methyl-n''-(2-([(5-methyl-1H-imidazol-4-yl)methyl]sulphanyl)ethyl)guanidine	Generator
Cimetidine HCL	HMDB
Eureceptor	HMDB
Histodil	HMDB
SK And F92334	HMDB
Biomet	HMDB
Cimetidine hydrochloride	HMDB
HCL, Cimetidine	HMDB
Hydrochloride, cimetidine	HMDB
N-Cyano-n'-methyl-n''-(2-(((5-methyl-1H-imidazol-4-yl)methyl)thio)ethyl)guanidine	HMDB
SK And F 92334	HMDB
SK And F-92334	HMDB
Altramet	HMDB
Biomet400	HMDB

Chemical Formula

C₁₀H₁₆N₆S

Average Molecular Weight

252.339

Monoisotopic Molecular Weight

252.115715232

IUPAC Name

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

Traditional Name

tagamet HB

CAS Registry Number

51481-61-9

SMILES

C\N=C(\NCCSCC1=C(C)NC=N1)NC#N

InChI Identifier

InChI=1S/C10H16N6S/c1-8-9(16-7-15-8)5-17-4-3-13-10(12-2)14-6-11/h7H,3-5H2,1-2H3,(H,15,16)(H2,12,13,14)

InChI Key

AQIXAKUUQRKLND-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
Thioether
Carboximidamide
Sulfenyl compound
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Dialkylthioether
Azacycle
Organic nitrogen compound
Organopnictogen compound
Imine
Organonitrogen compound
Organosulfur compound
Hydrocarbon derivative
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

imidazoles (CHEBI:3699 )
guanidines (CHEBI:3699 )
aliphatic sulfide (CHEBI:3699 )
nitrile (CHEBI:3699 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Blood (PMID: 21059682)

Cellular substructure

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Cimetidine Action Pathway (PathBank: SMP0000232)
Cimetidine Pathway (HMDB: HMDB0014644)

Metabolic pathway

Cimetidine Metabolism Pathway (PathBank: SMP0000617)

Role

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	142 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.82 g/L	Not Available
LogP	1	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	156.5	30932474

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.82 g/L	ALOGPS
logP	0.44	ALOGPS
logP	-0.11	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	13.38	ChemAxon
pKa (Strongest Basic)	6.91	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	88.89 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	70.32 m³·mol⁻¹	ChemAxon
Polarizability	27.47 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]+	158.166	31661259
DarkChem	[M-H]-	155.952	31661259
DeepCCS	[M+H]+	154.236	30932474
DeepCCS	[M-H]-	151.878	30932474
DeepCCS	[M-2H]-	187.125	30932474
DeepCCS	[M+Na]+	162.709	30932474
AllCCS	[M+H]+	156.0	32859911
AllCCS	[M+H-H2O]+	152.6	32859911
AllCCS	[M+NH4]+	159.1	32859911
AllCCS	[M+Na]+	159.9	32859911
AllCCS	[M-H]-	158.7	32859911
AllCCS	[M+Na-2H]-	159.3	32859911
AllCCS	[M+HCOO]-	160.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Cimetidine	C\N=C(\NCCSCC1=C(C)NC=N1)NC#N	3231.0	Standard polar	33892256
Cimetidine	C\N=C(\NCCSCC1=C(C)NC=N1)NC#N	2400.6	Standard non polar	33892256
Cimetidine	C\N=C(\NCCSCC1=C(C)NC=N1)NC#N	2796.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Cimetidine,1TMS,isomer #1	C/N=C(\NC#N)N(CCSCC1=C(C)[NH]C=N1)[Si](C)(C)C	2717.1	Semi standard non polar	33892256
Cimetidine,1TMS,isomer #1	C/N=C(\NC#N)N(CCSCC1=C(C)[NH]C=N1)[Si](C)(C)C	2204.7	Standard non polar	33892256
Cimetidine,1TMS,isomer #1	C/N=C(\NC#N)N(CCSCC1=C(C)[NH]C=N1)[Si](C)(C)C	4239.9	Standard polar	33892256
Cimetidine,1TMS,isomer #2	C/N=C(\NC#N)NCCSCC1=C(C)N([Si](C)(C)C)C=N1	2742.3	Semi standard non polar	33892256
Cimetidine,1TMS,isomer #2	C/N=C(\NC#N)NCCSCC1=C(C)N([Si](C)(C)C)C=N1	2219.6	Standard non polar	33892256
Cimetidine,1TMS,isomer #2	C/N=C(\NC#N)NCCSCC1=C(C)N([Si](C)(C)C)C=N1	4458.4	Standard polar	33892256
Cimetidine,1TMS,isomer #3	C/N=C(/NCCSCC1=C(C)[NH]C=N1)N(C#N)[Si](C)(C)C	2642.5	Semi standard non polar	33892256
Cimetidine,1TMS,isomer #3	C/N=C(/NCCSCC1=C(C)[NH]C=N1)N(C#N)[Si](C)(C)C	2217.9	Standard non polar	33892256
Cimetidine,1TMS,isomer #3	C/N=C(/NCCSCC1=C(C)[NH]C=N1)N(C#N)[Si](C)(C)C	4045.6	Standard polar	33892256
Cimetidine,2TMS,isomer #1	C/N=C(\N(C#N)[Si](C)(C)C)N(CCSCC1=C(C)[NH]C=N1)[Si](C)(C)C	2583.7	Semi standard non polar	33892256
Cimetidine,2TMS,isomer #1	C/N=C(\N(C#N)[Si](C)(C)C)N(CCSCC1=C(C)[NH]C=N1)[Si](C)(C)C	2300.5	Standard non polar	33892256
Cimetidine,2TMS,isomer #1	C/N=C(\N(C#N)[Si](C)(C)C)N(CCSCC1=C(C)[NH]C=N1)[Si](C)(C)C	3798.5	Standard polar	33892256
Cimetidine,2TMS,isomer #2	C/N=C(\NC#N)N(CCSCC1=C(C)N([Si](C)(C)C)C=N1)[Si](C)(C)C	2727.5	Semi standard non polar	33892256
Cimetidine,2TMS,isomer #2	C/N=C(\NC#N)N(CCSCC1=C(C)N([Si](C)(C)C)C=N1)[Si](C)(C)C	2294.7	Standard non polar	33892256
Cimetidine,2TMS,isomer #2	C/N=C(\NC#N)N(CCSCC1=C(C)N([Si](C)(C)C)C=N1)[Si](C)(C)C	4123.0	Standard polar	33892256
Cimetidine,2TMS,isomer #3	C/N=C(/NCCSCC1=C(C)N([Si](C)(C)C)C=N1)N(C#N)[Si](C)(C)C	2650.1	Semi standard non polar	33892256
Cimetidine,2TMS,isomer #3	C/N=C(/NCCSCC1=C(C)N([Si](C)(C)C)C=N1)N(C#N)[Si](C)(C)C	2318.1	Standard non polar	33892256
Cimetidine,2TMS,isomer #3	C/N=C(/NCCSCC1=C(C)N([Si](C)(C)C)C=N1)N(C#N)[Si](C)(C)C	3962.0	Standard polar	33892256
Cimetidine,3TMS,isomer #1	C/N=C(\N(C#N)[Si](C)(C)C)N(CCSCC1=C(C)N([Si](C)(C)C)C=N1)[Si](C)(C)C	2609.1	Semi standard non polar	33892256
Cimetidine,3TMS,isomer #1	C/N=C(\N(C#N)[Si](C)(C)C)N(CCSCC1=C(C)N([Si](C)(C)C)C=N1)[Si](C)(C)C	2400.3	Standard non polar	33892256
Cimetidine,3TMS,isomer #1	C/N=C(\N(C#N)[Si](C)(C)C)N(CCSCC1=C(C)N([Si](C)(C)C)C=N1)[Si](C)(C)C	3621.1	Standard polar	33892256
Cimetidine,1TBDMS,isomer #1	C/N=C(\NC#N)N(CCSCC1=C(C)[NH]C=N1)[Si](C)(C)C(C)(C)C	2908.4	Semi standard non polar	33892256
Cimetidine,1TBDMS,isomer #1	C/N=C(\NC#N)N(CCSCC1=C(C)[NH]C=N1)[Si](C)(C)C(C)(C)C	2421.1	Standard non polar	33892256
Cimetidine,1TBDMS,isomer #1	C/N=C(\NC#N)N(CCSCC1=C(C)[NH]C=N1)[Si](C)(C)C(C)(C)C	4247.8	Standard polar	33892256
Cimetidine,1TBDMS,isomer #2	C/N=C(\NC#N)NCCSCC1=C(C)N([Si](C)(C)C(C)(C)C)C=N1	2980.2	Semi standard non polar	33892256
Cimetidine,1TBDMS,isomer #2	C/N=C(\NC#N)NCCSCC1=C(C)N([Si](C)(C)C(C)(C)C)C=N1	2421.8	Standard non polar	33892256
Cimetidine,1TBDMS,isomer #2	C/N=C(\NC#N)NCCSCC1=C(C)N([Si](C)(C)C(C)(C)C)C=N1	4487.4	Standard polar	33892256
Cimetidine,1TBDMS,isomer #3	C/N=C(/NCCSCC1=C(C)[NH]C=N1)N(C#N)[Si](C)(C)C(C)(C)C	2844.4	Semi standard non polar	33892256
Cimetidine,1TBDMS,isomer #3	C/N=C(/NCCSCC1=C(C)[NH]C=N1)N(C#N)[Si](C)(C)C(C)(C)C	2422.7	Standard non polar	33892256
Cimetidine,1TBDMS,isomer #3	C/N=C(/NCCSCC1=C(C)[NH]C=N1)N(C#N)[Si](C)(C)C(C)(C)C	4044.3	Standard polar	33892256
Cimetidine,2TBDMS,isomer #1	C/N=C(\N(C#N)[Si](C)(C)C(C)(C)C)N(CCSCC1=C(C)[NH]C=N1)[Si](C)(C)C(C)(C)C	2948.2	Semi standard non polar	33892256
Cimetidine,2TBDMS,isomer #1	C/N=C(\N(C#N)[Si](C)(C)C(C)(C)C)N(CCSCC1=C(C)[NH]C=N1)[Si](C)(C)C(C)(C)C	2660.6	Standard non polar	33892256
Cimetidine,2TBDMS,isomer #1	C/N=C(\N(C#N)[Si](C)(C)C(C)(C)C)N(CCSCC1=C(C)[NH]C=N1)[Si](C)(C)C(C)(C)C	3780.0	Standard polar	33892256
Cimetidine,2TBDMS,isomer #2	C/N=C(\NC#N)N(CCSCC1=C(C)N([Si](C)(C)C(C)(C)C)C=N1)[Si](C)(C)C(C)(C)C	3102.5	Semi standard non polar	33892256
Cimetidine,2TBDMS,isomer #2	C/N=C(\NC#N)N(CCSCC1=C(C)N([Si](C)(C)C(C)(C)C)C=N1)[Si](C)(C)C(C)(C)C	2679.4	Standard non polar	33892256
Cimetidine,2TBDMS,isomer #2	C/N=C(\NC#N)N(CCSCC1=C(C)N([Si](C)(C)C(C)(C)C)C=N1)[Si](C)(C)C(C)(C)C	4129.0	Standard polar	33892256
Cimetidine,2TBDMS,isomer #3	C/N=C(/NCCSCC1=C(C)N([Si](C)(C)C(C)(C)C)C=N1)N(C#N)[Si](C)(C)C(C)(C)C	3037.7	Semi standard non polar	33892256
Cimetidine,2TBDMS,isomer #3	C/N=C(/NCCSCC1=C(C)N([Si](C)(C)C(C)(C)C)C=N1)N(C#N)[Si](C)(C)C(C)(C)C	2691.4	Standard non polar	33892256
Cimetidine,2TBDMS,isomer #3	C/N=C(/NCCSCC1=C(C)N([Si](C)(C)C(C)(C)C)C=N1)N(C#N)[Si](C)(C)C(C)(C)C	3950.8	Standard polar	33892256
Cimetidine,3TBDMS,isomer #1	C/N=C(\N(C#N)[Si](C)(C)C(C)(C)C)N(CCSCC1=C(C)N([Si](C)(C)C(C)(C)C)C=N1)[Si](C)(C)C(C)(C)C	3186.0	Semi standard non polar	33892256
Cimetidine,3TBDMS,isomer #1	C/N=C(\N(C#N)[Si](C)(C)C(C)(C)C)N(CCSCC1=C(C)N([Si](C)(C)C(C)(C)C)C=N1)[Si](C)(C)C(C)(C)C	2911.5	Standard non polar	33892256
Cimetidine,3TBDMS,isomer #1	C/N=C(\N(C#N)[Si](C)(C)C(C)(C)C)N(CCSCC1=C(C)N([Si](C)(C)C(C)(C)C)C=N1)[Si](C)(C)C(C)(C)C	3656.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Cimetidine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0005-9500000000-8ff5fa28797a788c95be	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cimetidine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-002b-9510000000-36ce01132725fd5bf5d8	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cimetidine LC-ESI-QFT , negative-QTOF	splash10-0a4j-5900000000-122f9dbdf583bbe3dee8	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cimetidine LC-ESI-QFT , negative-QTOF	splash10-0002-9300000000-39ee157d9e264867cfa4	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cimetidine LC-ESI-QFT , negative-QTOF	splash10-0002-9000000000-6e876a668444c8277412	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cimetidine LC-ESI-QFT , negative-QTOF	splash10-0002-9000000000-85640be9b2799889fd02	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cimetidine LC-ESI-QFT , negative-QTOF	splash10-0002-9000000000-9b8d3eafde213bee6396	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cimetidine LC-ESI-QFT , negative-QTOF	splash10-0a4j-9000000000-b47e11697992a843f5e4	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cimetidine LC-ESI-QFT , negative-QTOF	splash10-0a4i-9000000000-75ebe86c90f5ed341c57	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cimetidine LC-ESI-QFT , negative-QTOF	splash10-0aor-9000000000-d7302885bef7454b4db2	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cimetidine LC-ESI-QFT , negative-QTOF	splash10-014i-9000000000-b2f3ab1b5ae1e2f8f8bb	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cimetidine LC-ESI-QQ , negative-QTOF	splash10-0a4i-0930000000-dbae8348b5c999cc664d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cimetidine LC-ESI-QQ , negative-QTOF	splash10-052b-9600000000-8b4b94cd7303c9b9a0ef	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cimetidine LC-ESI-QQ , negative-QTOF	splash10-0002-9000000000-c23b62afdf4dff8c43db	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cimetidine LC-ESI-QQ , negative-QTOF	splash10-0002-9000000000-e477cd71a628f6adaf46	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cimetidine LC-ESI-QQ , negative-QTOF	splash10-052e-9000000000-61584ad991262d50a01b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cimetidine 40V, Negative-QTOF	splash10-0006-9000000000-88151759e4ec7e461e1d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cimetidine 20V, Negative-QTOF	splash10-0002-9000000000-84933ca72cf6d95badca	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cimetidine 10V, Negative-QTOF	splash10-052b-9600000000-83ce94b92714f218f567	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cimetidine 15V, Negative-QTOF	splash10-0a4j-5900000000-341f95e97b0eb6634dfa	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cimetidine 90V, Negative-QTOF	splash10-0a4j-9000000000-b76e965288a7920d0a3e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cimetidine 75V, Negative-QTOF	splash10-0002-9000000000-5b0e434ce0c42ad72d42	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cimetidine 45V, Negative-QTOF	splash10-0002-9000000000-d792a4f8d6e0e511ad69	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cimetidine 30V, Negative-QTOF	splash10-0002-9300000000-def54138c107c3ecad02	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cimetidine 60V, Negative-QTOF	splash10-0002-9000000000-d7fd678797f771750ed9	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cimetidine LC-ESI-qTof , Positive-QTOF	splash10-0002-9511000000-75fc9243ad1eb9c79cb4	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cimetidine LC-ESI-QFT , positive-QTOF	splash10-0zfr-1980000000-84e04b032e6f422e5b6b	2017-09-14	HMDB team, MONA	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Cimetidine Action Pathway		Not Available
Cimetidine Metabolism Pathway		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00501	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00501	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00501

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB010095

KNApSAcK ID

Not Available

Chemspider ID

2654

KEGG Compound ID

C06952

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Cimetidine

METLIN ID

Not Available

PubChem Compound

2756

PDB ID

Not Available

ChEBI ID

3699

Food Biomarker Ontology

Not Available

VMH ID

M01571

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Michnovicz JJ, Galbraith RA: Cimetidine inhibits catechol estrogen metabolism in women. Metabolism. 1991 Feb;40(2):170-4. [PubMed:1988774 ]

Only showing the first 10 proteins. There are 23 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Dimethylaniline monooxygenase [N-oxide-forming] 3

General function:: Involved in flavin-containing monooxygenase activity
Specific function:: Involved in the oxidative metabolism of a variety of xenobiotics such as drugs and pesticides. It N-oxygenates primary aliphatic alkylamines as well as secondary and tertiary amines. Plays an important role in the metabolism of trimethylamine (TMA), via the production of TMA N-oxide (TMAO). Is also able to perform S-oxidation when acting on sulfide compounds.
Gene Name:: FMO3
Uniprot ID:: P31513
Molecular weight:: 60032.975

References

Cashman JR: Human flavin-containing monooxygenase: substrate specificity and role in drug metabolism. Curr Drug Metab. 2000 Sep;1(2):181-91. [PubMed:11465082 ]
Cashman JR, Park SB, Berkman CE, Cashman LE: Role of hepatic flavin-containing monooxygenase 3 in drug and chemical metabolism in adult humans. Chem Biol Interact. 1995 Apr 28;96(1):33-46. [PubMed:7720103 ]
Hai X, Adams E, Hoogmartens J, Van Schepdael A: Enantioselective in-line and off-line CE methods for the kinetic study on cimetidine and its chiral metabolites with reference to flavin-containing monooxygenase genetic isoforms. Electrophoresis. 2009 Apr;30(7):1248-57. doi: 10.1002/elps.200800604. [PubMed:19283698 ]

Enzyme Details

2. Dimethylaniline monooxygenase [N-oxide-forming] 1

General function:: Involved in flavin-containing monooxygenase activity
Specific function:: This protein is involved in the oxidative metabolism of a variety of xenobiotics such as drugs and pesticides. Form I catalyzes the N-oxygenation of secondary and tertiary amines.
Gene Name:: FMO1
Uniprot ID:: Q01740
Molecular weight:: 60310.285

References

Hai X, Adams E, Hoogmartens J, Van Schepdael A: Enantioselective in-line and off-line CE methods for the kinetic study on cimetidine and its chiral metabolites with reference to flavin-containing monooxygenase genetic isoforms. Electrophoresis. 2009 Apr;30(7):1248-57. doi: 10.1002/elps.200800604. [PubMed:19283698 ]
Cashman JR: Human flavin-containing monooxygenase: substrate specificity and role in drug metabolism. Curr Drug Metab. 2000 Sep;1(2):181-91. [PubMed:11465082 ]

Enzyme Details

3. Cytochrome P450 11B1, mitochondrial

General function:: Involved in monooxygenase activity
Specific function:: Has steroid 11-beta-hydroxylase activity. In addition to this activity, the 18 or 19-hydroxylation of steroids and the aromatization of androstendione to estrone have also been ascribed to cytochrome P450 XIB.
Gene Name:: CYP11B1
Uniprot ID:: P15538
Molecular weight:: 57572.44

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

4. Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

5. Cytochrome P450 2C9

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:: CYP2C9
Uniprot ID:: P11712
Molecular weight:: 55627.365

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

6. Cytochrome P450 2C19

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:: CYP2C19
Uniprot ID:: P33261
Molecular weight:: 55944.565

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

7. Cytochrome P450 2E1

General function:: Involved in monooxygenase activity
Specific function:: Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic or carcinogenic forms.
Gene Name:: CYP2E1
Uniprot ID:: P05181
Molecular weight:: 56848.42

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

8. Cytochrome P450 2D6

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:: CYP2D6
Uniprot ID:: P10635
Molecular weight:: 55768.94

Enzyme Details

9. Cytochrome P450 3A5

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:: CYP3A5
Uniprot ID:: P20815
Molecular weight:: 57108.065

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

10. Cytochrome P450 3A7

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:: CYP3A7
Uniprot ID:: P24462
Molecular weight:: 57525.03

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Transporters

Enzyme Details

1. Solute carrier family 22 member 5

General function:: Involved in ion transmembrane transporter activity
Specific function:: Sodium-ion dependent, high affinity carnitine transporter. Involved in the active cellular uptake of carnitine. Transports one sodium ion with one molecule of carnitine. Also transports organic cations such as tetraethylammonium (TEA) without the involvement of sodium. Also relative uptake activity ratio of carnitine to TEA is 11.3
Gene Name:: SLC22A5
Uniprot ID:: O76082
Molecular weight:: 62751.1

References

Wu X, Prasad PD, Leibach FH, Ganapathy V: cDNA sequence, transport function, and genomic organization of human OCTN2, a new member of the organic cation transporter family. Biochem Biophys Res Commun. 1998 May 29;246(3):589-95. [PubMed:9618255 ]
Ohashi R, Tamai I, Yabuuchi H, Nezu JI, Oku A, Sai Y, Shimane M, Tsuji A: Na(+)-dependent carnitine transport by organic cation transporter (OCTN2): its pharmacological and toxicological relevance. J Pharmacol Exp Ther. 1999 Nov;291(2):778-84. [PubMed:10525100 ]
Wu X, Huang W, Prasad PD, Seth P, Rajan DP, Leibach FH, Chen J, Conway SJ, Ganapathy V: Functional characteristics and tissue distribution pattern of organic cation transporter 2 (OCTN2), an organic cation/carnitine transporter. J Pharmacol Exp Ther. 1999 Sep;290(3):1482-92. [PubMed:10454528 ]

Enzyme Details

2. Bile salt export pump

General function:: Involved in ATP binding
Specific function:: Involved in the ATP-dependent secretion of bile salts into the canaliculus of hepatocytes
Gene Name:: ABCB11
Uniprot ID:: O95342
Molecular weight:: 146405.8

References

Wang EJ, Casciano CN, Clement RP, Johnson WW: Fluorescent substrates of sister-P-glycoprotein (BSEP) evaluated as markers of active transport and inhibition: evidence for contingent unequal binding sites. Pharm Res. 2003 Apr;20(4):537-44. [PubMed:12739759 ]

Enzyme Details

3. Multidrug resistance protein 1

General function:: Involved in ATP binding
Specific function:: Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
Gene Name:: ABCB1
Uniprot ID:: P08183
Molecular weight:: 141477.3

References

Romiti N, Tramonti G, Chieli E: Influence of different chemicals on MDR-1 P-glycoprotein expression and activity in the HK-2 proximal tubular cell line. Toxicol Appl Pharmacol. 2002 Sep 1;183(2):83-91. [PubMed:12387747 ]
Lentz KA, Polli JW, Wring SA, Humphreys JE, Polli JE: Influence of passive permeability on apparent P-glycoprotein kinetics. Pharm Res. 2000 Dec;17(12):1456-60. [PubMed:11303953 ]
Schwab D, Fischer H, Tabatabaei A, Poli S, Huwyler J: Comparison of in vitro P-glycoprotein screening assays: recommendations for their use in drug discovery. J Med Chem. 2003 Apr 24;46(9):1716-25. [PubMed:12699389 ]
van der Sandt IC, Blom-Roosemalen MC, de Boer AG, Breimer DD: Specificity of doxorubicin versus rhodamine-123 in assessing P-glycoprotein functionality in the LLC-PK1, LLC-PK1:MDR1 and Caco-2 cell lines. Eur J Pharm Sci. 2000 Sep;11(3):207-14. [PubMed:11042226 ]
Ito T, Yano I, Tanaka K, Inui KI: Transport of quinolone antibacterial drugs by human P-glycoprotein expressed in a kidney epithelial cell line, LLC-PK1. J Pharmacol Exp Ther. 1997 Aug;282(2):955-60. [PubMed:9262363 ]
Adachi Y, Suzuki H, Sugiyama Y: Comparative studies on in vitro methods for evaluating in vivo function of MDR1 P-glycoprotein. Pharm Res. 2001 Dec;18(12):1660-8. [PubMed:11785684 ]

Enzyme Details

4. Solute carrier family 22 member 11

General function:: Involved in transporter activity
Specific function:: Mediates saturable uptake of estrone sulfate, dehydroepiandrosterone sulfate and related compounds
Gene Name:: SLC22A11
Uniprot ID:: Q9NSA0
Molecular weight:: 59970.9

References

Khamdang S, Takeda M, Shimoda M, Noshiro R, Narikawa S, Huang XL, Enomoto A, Piyachaturawat P, Endou H: Interactions of human- and rat-organic anion transporters with pravastatin and cimetidine. J Pharmacol Sci. 2004 Feb;94(2):197-202. [PubMed:14978359 ]

Enzyme Details

5. Solute carrier family 22 member 4

General function:: Involved in ion transmembrane transporter activity
Specific function:: Sodium-ion dependent, low affinity carnitine transporter. Probably transports one sodium ion with one molecule of carnitine. Also transports organic cations such as tetraethylammonium (TEA) without the involvement of sodium. Relative uptake activity ratio of carnitine to TEA is 1.78. A key substrate of this transporter seems to be ergothioneine (ET)
Gene Name:: SLC22A4
Uniprot ID:: Q9H015
Molecular weight:: 62154.5

References

Yabuuchi H, Tamai I, Nezu J, Sakamoto K, Oku A, Shimane M, Sai Y, Tsuji A: Novel membrane transporter OCTN1 mediates multispecific, bidirectional, and pH-dependent transport of organic cations. J Pharmacol Exp Ther. 1999 May;289(2):768-73. [PubMed:10215651 ]
Wu X, George RL, Huang W, Wang H, Conway SJ, Leibach FH, Ganapathy V: Structural and functional characteristics and tissue distribution pattern of rat OCTN1, an organic cation transporter, cloned from placenta. Biochim Biophys Acta. 2000 Jun 1;1466(1-2):315-27. [PubMed:10825452 ]

Enzyme Details

6. Solute carrier family 22 member 1

General function:: Involved in ion transmembrane transporter activity
Specific function:: Translocates a broad array of organic cations with various structures and molecular weights including the model compounds 1-methyl-4-phenylpyridinium (MPP), tetraethylammonium (TEA), N-1-methylnicotinamide (NMN), 4-(4-(dimethylamino)styryl)- N-methylpyridinium (ASP), the endogenous compounds choline, guanidine, histamine, epinephrine, adrenaline, noradrenaline and dopamine, and the drugs quinine, and metformin. The transport of organic cations is inhibited by a broad array of compounds like tetramethylammonium (TMA), cocaine, lidocaine, NMDA receptor antagonists, atropine, prazosin, cimetidine, TEA and NMN, guanidine, cimetidine, choline, procainamide, quinine, tetrabutylammonium, and tetrapentylammonium. Translocates organic cations in an electrogenic and pH-independent manner. Translocates organic cations across the plasma membrane in both directions. Transports the polyamines spermine and spermidine. Transports pramipexole across the basolateral membrane of the proximal tubular epithelial cells. The choline transport is activated by MMTS. Regulated by various intracellular signaling pathways including inhibition by protein kinase A activation, and endogenously activation by the calmodulin complex, the calmodulin- dependent kinase II and LCK tyrosine kinase
Gene Name:: SLC22A1
Uniprot ID:: O15245
Molecular weight:: 61187.4

References

Zhang L, Dresser MJ, Gray AT, Yost SC, Terashita S, Giacomini KM: Cloning and functional expression of a human liver organic cation transporter. Mol Pharmacol. 1997 Jun;51(6):913-21. [PubMed:9187257 ]
Zhang L, Schaner ME, Giacomini KM: Functional characterization of an organic cation transporter (hOCT1) in a transiently transfected human cell line (HeLa). J Pharmacol Exp Ther. 1998 Jul;286(1):354-61. [PubMed:9655880 ]
Kakehi M, Koyabu N, Nakamura T, Uchiumi T, Kuwano M, Ohtani H, Sawada Y: Functional characterization of mouse cation transporter mOCT2 compared with mOCT1. Biochem Biophys Res Commun. 2002 Aug 23;296(3):644-50. [PubMed:12176030 ]
Zhang L, Dresser MJ, Chun JK, Babbitt PC, Giacomini KM: Cloning and functional characterization of a rat renal organic cation transporter isoform (rOCT1A). J Biol Chem. 1997 Jun 27;272(26):16548-54. [PubMed:9195965 ]
Urakami Y, Okuda M, Masuda S, Saito H, Inui KI: Functional characteristics and membrane localization of rat multispecific organic cation transporters, OCT1 and OCT2, mediating tubular secretion of cationic drugs. J Pharmacol Exp Ther. 1998 Nov;287(2):800-5. [PubMed:9808712 ]
Okuda M, Urakami Y, Saito H, Inui K: Molecular mechanisms of organic cation transport in OCT2-expressing Xenopus oocytes. Biochim Biophys Acta. 1999 Mar 4;1417(2):224-31. [PubMed:10082798 ]
Jonker JW, Wagenaar E, Mol CA, Buitelaar M, Koepsell H, Smit JW, Schinkel AH: Reduced hepatic uptake and intestinal excretion of organic cations in mice with a targeted disruption of the organic cation transporter 1 (Oct1 [Slc22a1]) gene. Mol Cell Biol. 2001 Aug;21(16):5471-7. [PubMed:11463829 ]
Grundemann D, Liebich G, Kiefer N, Koster S, Schomig E: Selective substrates for non-neuronal monoamine transporters. Mol Pharmacol. 1999 Jul;56(1):1-10. [PubMed:10385678 ]

Enzyme Details

7. Solute carrier family 22 member 2

General function:: Involved in ion transmembrane transporter activity
Specific function:: Mediates tubular uptake of organic compounds from circulation. Mediates the influx of agmatine, dopamine, noradrenaline (norepinephrine), serotonin, choline, famotidine, ranitidine, histamin, creatinine, amantadine, memantine, acriflavine, 4-[4-(dimethylamino)-styryl]-N-methylpyridinium ASP, amiloride, metformin, N-1-methylnicotinamide (NMN), tetraethylammonium (TEA), 1-methyl-4-phenylpyridinium (MPP), cimetidine, cisplatin and oxaliplatin. Cisplatin may develop a nephrotoxic action. Transport of creatinine is inhibited by fluoroquinolones such as DX-619 and LVFX. This transporter is a major determinant of the anticancer activity of oxaliplatin and may contribute to antitumor specificity
Gene Name:: SLC22A2
Uniprot ID:: O15244
Molecular weight:: 62564.0

References

Urakami Y, Akazawa M, Saito H, Okuda M, Inui K: cDNA cloning, functional characterization, and tissue distribution of an alternatively spliced variant of organic cation transporter hOCT2 predominantly expressed in the human kidney. J Am Soc Nephrol. 2002 Jul;13(7):1703-10. [PubMed:12089365 ]
Motohashi H, Uwai Y, Hiramoto K, Okuda M, Inui K: Different transport properties between famotidine and cimetidine by human renal organic ion transporters (SLC22A). Eur J Pharmacol. 2004 Oct 25;503(1-3):25-30. [PubMed:15496291 ]
Kakehi M, Koyabu N, Nakamura T, Uchiumi T, Kuwano M, Ohtani H, Sawada Y: Functional characterization of mouse cation transporter mOCT2 compared with mOCT1. Biochem Biophys Res Commun. 2002 Aug 23;296(3):644-50. [PubMed:12176030 ]
Urakami Y, Okuda M, Masuda S, Saito H, Inui KI: Functional characteristics and membrane localization of rat multispecific organic cation transporters, OCT1 and OCT2, mediating tubular secretion of cationic drugs. J Pharmacol Exp Ther. 1998 Nov;287(2):800-5. [PubMed:9808712 ]
Okuda M, Urakami Y, Saito H, Inui K: Molecular mechanisms of organic cation transport in OCT2-expressing Xenopus oocytes. Biochim Biophys Acta. 1999 Mar 4;1417(2):224-31. [PubMed:10082798 ]
Pan BF, Sweet DH, Pritchard JB, Chen R, Nelson JA: A transfected cell model for the renal toxin transporter, rOCT2. Toxicol Sci. 1999 Feb;47(2):181-6. [PubMed:10220855 ]
Dudley AJ, Bleasby K, Brown CD: The organic cation transporter OCT2 mediates the uptake of beta-adrenoceptor antagonists across the apical membrane of renal LLC-PK(1) cell monolayers. Br J Pharmacol. 2000 Sep;131(1):71-9. [PubMed:10960071 ]
Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]

Enzyme Details

8. Solute carrier family 22 member 3

General function:: Involved in transmembrane transport
Specific function:: Mediates potential-dependent transport of a variety of organic cations. May play a significant role in the disposition of cationic neurotoxins and neurotransmitters in the brain
Gene Name:: SLC22A3
Uniprot ID:: O75751
Molecular weight:: 61279.5

References

Grundemann D, Schechinger B, Rappold GA, Schomig E: Molecular identification of the corticosterone-sensitive extraneuronal catecholamine transporter. Nat Neurosci. 1998 Sep;1(5):349-51. [PubMed:10196521 ]
Wu X, Huang W, Ganapathy ME, Wang H, Kekuda R, Conway SJ, Leibach FH, Ganapathy V: Structure, function, and regional distribution of the organic cation transporter OCT3 in the kidney. Am J Physiol Renal Physiol. 2000 Sep;279(3):F449-58. [PubMed:10966924 ]
Kekuda R, Prasad PD, Wu X, Wang H, Fei YJ, Leibach FH, Ganapathy V: Cloning and functional characterization of a potential-sensitive, polyspecific organic cation transporter (OCT3) most abundantly expressed in placenta. J Biol Chem. 1998 Jun 26;273(26):15971-9. [PubMed:9632645 ]
Grundemann D, Liebich G, Kiefer N, Koster S, Schomig E: Selective substrates for non-neuronal monoamine transporters. Mol Pharmacol. 1999 Jul;56(1):1-10. [PubMed:10385678 ]

Enzyme Details

9. Solute carrier family 22 member 6

General function:: Involved in ion transmembrane transporter activity
Specific function:: Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one molecule of endogenous dicarboxylic acid (glutarate, ketoglutarate, etc). Mediates the sodium-independent uptake of 2,3-dimercapto-1-propanesulfonic acid (DMPS). Mediates the sodium-independent uptake of p- aminohippurate (PAH), ochratoxin (OTA), acyclovir (ACV), 3'-azido- 3-'deoxythymidine (AZT), cimetidine (CMD), 2,4-dichloro- phenoxyacetate (2,4-D), hippurate (HA), indoleacetate (IA), indoxyl sulfate (IS) and 3-carboxy-4-methyl-5-propyl-2- furanpropionate (CMPF), cidofovir, adefovir, 9-(2- phosphonylmethoxyethyl) guanine (PMEG), 9-(2- phosphonylmethoxyethyl) diaminopurine (PMEDAP) and edaravone sulfate. PAH uptake is inhibited by p- chloromercuribenzenesulphonate (PCMBS), diethyl pyrocarbonate (DEPC), sulindac, diclofenac, carprofen, glutarate and okadaic acid. PAH uptake is inhibited by benzothiazolylcysteine (BTC), S-chlorotrifluoroethylcysteine (CTFC), cysteine S-conjugates S-dichlorovinylcysteine (DCVC), furosemide, steviol, phorbol 12-myristate 13-acetate (PMA), calcium ionophore A23187, benzylpenicillin, furosemide, indomethacin, bumetamide, losartan, probenecid, phenol red, urate, and alpha-ketoglutarate
Gene Name:: SLC22A6
Uniprot ID:: Q4U2R8
Molecular weight:: 61815.8

References

Jung KY, Takeda M, Kim DK, Tojo A, Narikawa S, Yoo BS, Hosoyamada M, Cha SH, Sekine T, Endou H: Characterization of ochratoxin A transport by human organic anion transporters. Life Sci. 2001 Sep 21;69(18):2123-35. [PubMed:11669456 ]
Khamdang S, Takeda M, Shimoda M, Noshiro R, Narikawa S, Huang XL, Enomoto A, Piyachaturawat P, Endou H: Interactions of human- and rat-organic anion transporters with pravastatin and cimetidine. J Pharmacol Sci. 2004 Feb;94(2):197-202. [PubMed:14978359 ]
Nagata Y, Kusuhara H, Endou H, Sugiyama Y: Expression and functional characterization of rat organic anion transporter 3 (rOat3) in the choroid plexus. Mol Pharmacol. 2002 May;61(5):982-8. [PubMed:11961115 ]
Burckhardt BC, Brai S, Wallis S, Krick W, Wolff NA, Burckhardt G: Transport of cimetidine by flounder and human renal organic anion transporter 1. Am J Physiol Renal Physiol. 2003 Mar;284(3):F503-9. Epub 2002 Nov 12. [PubMed:12429554 ]

Enzyme Details

10. Solute carrier family 22 member 7

General function:: Involved in transmembrane transport
Specific function:: Mediates sodium-independent multispecific organic anion transport. Transport of prostaglandin E2, prostaglandin F2, tetracycline, bumetanide, estrone sulfate, glutarate, dehydroepiandrosterone sulfate, allopurinol, 5-fluorouracil, paclitaxel, L-ascorbic acid, salicylate, ethotrexate, and alpha- ketoglutarate
Gene Name:: SLC22A7
Uniprot ID:: Q9Y694
Molecular weight:: 60025.0

References

Kobayashi Y, Ohshiro N, Shibusawa A, Sasaki T, Tokuyama S, Sekine T, Endou H, Yamamoto T: Isolation, characterization and differential gene expression of multispecific organic anion transporter 2 in mice. Mol Pharmacol. 2002 Jul;62(1):7-14. [PubMed:12065749 ]
Kusuhara H, Sekine T, Utsunomiya-Tate N, Tsuda M, Kojima R, Cha SH, Sugiyama Y, Kanai Y, Endou H: Molecular cloning and characterization of a new multispecific organic anion transporter from rat brain. J Biol Chem. 1999 May 7;274(19):13675-80. [PubMed:10224140 ]

Only showing the first 10 proteins. There are 23 proteins in total.

Show all enzymes and transporters

Showing metabocard for Cimetidine (HMDB0014644)

MOL for HMDB0014644 (Cimetidine)

3D MOL for HMDB0014644 (Cimetidine)

3D SDF for HMDB0014644 (Cimetidine)

3D-SDF for HMDB0014644 (Cimetidine)

PDB for HMDB0014644 (Cimetidine)

3D PDB for HMDB0014644 (Cimetidine)

SMILES for HMDB0014644 (Cimetidine)

INCHI for HMDB0014644 (Cimetidine)

Structure for HMDB0014644 (Cimetidine)

3D Structure for HMDB0014644 (Cimetidine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

References

References

References

References

References

References

References

References

References

Transporters

References

References

References

References

References

References

References

References

References

References