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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 14:46:47 UTC

Update Date

2021-09-26 23:09:49 UTC

HMDB ID

HMDB0255201

Secondary Accession Numbers

None

Metabolite Identification

Common Name

N-Nitrosocimetidine

Description

N-Nitrosocimetidine 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 a significant number of articles have been published on N-Nitrosocimetidine. This compound has been identified in human blood as reported by (PMID: 31557052 ). N-nitrosocimetidine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically N-Nitrosocimetidine 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

HMDB0255201
     RDKit          3D
N-Nitrosocimetidine
 34 34  0  0  0  0  0  0  0  0999 V2000
    5.1071    1.3435    0.3028 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4327    0.0771   -0.1311 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9614   -1.1306   -0.3182 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0270   -2.0415   -0.6141 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8278   -1.3673   -0.6101 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0187   -0.0874   -0.3281 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2410    1.1554   -0.4361 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9999    1.5333    0.6049 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5853    0.8573    0.8537 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9497   -0.2565   -0.0884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0778   -0.9234    0.3240 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3027   -0.7953    0.4609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0116   -2.0065    1.0166 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1871   -3.0868    0.1653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3121   -3.9697   -0.5819 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1228    0.2658    0.1494 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9521    1.3869   -0.7207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4511    0.3003    0.8149 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5518    0.4606    2.0204 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6755    1.7882   -0.4884 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2935    2.0776    0.5751 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6375    1.2067    1.2863 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0089   -1.3920   -0.3025 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1553   -3.1149   -0.8753 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7325    0.9762   -1.5515 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8817    2.0548   -0.7355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7578    0.5112    1.9257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3460    1.7228    0.6892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0600    0.2090   -1.1475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0188   -0.8766   -0.2551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2979   -1.9315    1.9899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8857    1.3424   -1.3696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0273    2.3601   -0.1499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1029    1.3509   -1.3609 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  3
 12 13  1  0
 13 14  1  0
 14 15  3  0
 12 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
  6  2  2  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  4 24  1  0
  7 25  1  0
  7 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 13 31  1  0
 17 32  1  0
 17 33  1  0
 17 34  1  0
M  END


  Mrv1652309112116472D          

 19 19  0  0  0  0            999 V2000
   -3.7753    0.9932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6037    0.1862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8501   -0.1494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9363   -0.9698    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7433   -1.1414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1558   -0.4269    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1356    0.2631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4211   -0.1494    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7066    0.2631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0078   -0.1494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7223    0.2631    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4368   -0.1494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1512    0.2631    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1512    1.0881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1512    1.9131    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4368   -0.9744    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7223   -1.3869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1512   -1.3869    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1512   -2.2119    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 11 10  1  4  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  3  0  0  0  0
 12 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0255201

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C10H15N7OS/c1-8-9(15-7-14-8)5-19-4-3-12-10(13-6-11)17(2)16-18/h7H,3-5H2,1-2H3,(H,12,13)(H,14,15)

> <INCHI_KEY>
LFTUYYPQNCJQGN-UHFFFAOYSA-N

> <FORMULA>
C10H15N7OS

> <MOLECULAR_WEIGHT>
281.34

> <EXACT_MASS>
281.105879305

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
28.99123188727021

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.08

> <JCHEM_LOGP>
0.38970221799999955

> <ALOGPS_LOGS>
-2.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
19.14382706419815

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.382495038627773

> <JCHEM_PKA_STRONGEST_BASIC>
6.911815008072931

> <JCHEM_POLAR_SURFACE_AREA>
109.53

> <JCHEM_REFRACTIVITY>
75.6742

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.31e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0255201
     RDKit          3D
N-Nitrosocimetidine
 34 34  0  0  0  0  0  0  0  0999 V2000
    5.1071    1.3435    0.3028 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4327    0.0771   -0.1311 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9614   -1.1306   -0.3182 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0270   -2.0415   -0.6141 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8278   -1.3673   -0.6101 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0187   -0.0874   -0.3281 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2410    1.1554   -0.4361 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9999    1.5333    0.6049 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5853    0.8573    0.8537 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9497   -0.2565   -0.0884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0778   -0.9234    0.3240 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3027   -0.7953    0.4609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0116   -2.0065    1.0166 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1871   -3.0868    0.1653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3121   -3.9697   -0.5819 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1228    0.2658    0.1494 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9521    1.3869   -0.7207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4511    0.3003    0.8149 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5518    0.4606    2.0204 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6755    1.7882   -0.4884 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2935    2.0776    0.5751 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6375    1.2067    1.2863 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0089   -1.3920   -0.3025 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1553   -3.1149   -0.8753 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7325    0.9762   -1.5515 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8817    2.0548   -0.7355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7578    0.5112    1.9257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3460    1.7228    0.6892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0600    0.2090   -1.1475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0188   -0.8766   -0.2551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2979   -1.9315    1.9899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8857    1.3424   -1.3696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0273    2.3601   -0.1499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1029    1.3509   -1.3609 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  3
 12 13  1  0
 13 14  1  0
 14 15  3  0
 12 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
  6  2  2  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  4 24  1  0
  7 25  1  0
  7 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 13 31  1  0
 17 32  1  0
 17 33  1  0
 17 34  1  0
M  END

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0      -7.047   1.854   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.727   0.348   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.320  -0.279   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0      -5.481  -1.810   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      -6.987  -2.131   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      -7.757  -0.797   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      -3.986   0.491   0.000  0.00  0.00           C+0
HETATM    8  S   UNK     0      -2.653  -0.279   0.000  0.00  0.00           S+0
HETATM    9  C   UNK     0      -1.319   0.491   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.015  -0.279   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       1.348   0.491   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       2.682  -0.279   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       4.016   0.491   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0       4.016   2.031   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       4.016   3.571   0.000  0.00  0.00           N+0
HETATM   16  N   UNK     0       2.682  -1.819   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0       1.348  -2.589   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       4.016  -2.589   0.000  0.00  0.00           N+0
HETATM   19  O   UNK     0       4.016  -4.129   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4    7                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    2                                                       
CONECT    7    3    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   16                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14                                                            
CONECT   16   12   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   38    0
END

COMPND    HMDB0255201
HETATM    1  C1  UNL     1       5.107   1.343   0.303  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.433   0.077  -0.131  1.00  0.00           C  
HETATM    3  N1  UNL     1       4.961  -1.131  -0.318  1.00  0.00           N  
HETATM    4  C3  UNL     1       4.027  -2.041  -0.614  1.00  0.00           C  
HETATM    5  N2  UNL     1       2.828  -1.367  -0.610  1.00  0.00           N  
HETATM    6  C4  UNL     1       3.019  -0.087  -0.328  1.00  0.00           C  
HETATM    7  C5  UNL     1       2.241   1.155  -0.436  1.00  0.00           C  
HETATM    8  S1  UNL     1       1.000   1.533   0.605  1.00  0.00           S  
HETATM    9  C6  UNL     1      -0.585   0.857   0.854  1.00  0.00           C  
HETATM   10  C7  UNL     1      -0.950  -0.256  -0.088  1.00  0.00           C  
HETATM   11  N3  UNL     1      -2.078  -0.923   0.324  1.00  0.00           N  
HETATM   12  C8  UNL     1      -3.303  -0.795   0.461  1.00  0.00           C  
HETATM   13  N4  UNL     1      -4.012  -2.007   1.017  1.00  0.00           N  
HETATM   14  C9  UNL     1      -4.187  -3.087   0.165  1.00  0.00           C  
HETATM   15  N5  UNL     1      -4.312  -3.970  -0.582  1.00  0.00           N  
HETATM   16  N6  UNL     1      -4.123   0.266   0.149  1.00  0.00           N  
HETATM   17  C10 UNL     1      -3.952   1.387  -0.721  1.00  0.00           C  
HETATM   18  N7  UNL     1      -5.451   0.300   0.815  1.00  0.00           N  
HETATM   19  O1  UNL     1      -5.552   0.461   2.020  1.00  0.00           O  
HETATM   20  H1  UNL     1       5.676   1.788  -0.488  1.00  0.00           H  
HETATM   21  H2  UNL     1       4.294   2.078   0.575  1.00  0.00           H  
HETATM   22  H3  UNL     1       5.638   1.207   1.286  1.00  0.00           H  
HETATM   23  H4  UNL     1       6.009  -1.392  -0.302  1.00  0.00           H  
HETATM   24  H5  UNL     1       4.155  -3.115  -0.875  1.00  0.00           H  
HETATM   25  H6  UNL     1       1.732   0.976  -1.552  1.00  0.00           H  
HETATM   26  H7  UNL     1       2.882   2.055  -0.736  1.00  0.00           H  
HETATM   27  H8  UNL     1      -0.758   0.511   1.926  1.00  0.00           H  
HETATM   28  H9  UNL     1      -1.346   1.723   0.689  1.00  0.00           H  
HETATM   29  H10 UNL     1      -1.060   0.209  -1.147  1.00  0.00           H  
HETATM   30  H11 UNL     1      -0.019  -0.877  -0.255  1.00  0.00           H  
HETATM   31  H12 UNL     1      -4.298  -1.932   1.990  1.00  0.00           H  
HETATM   32  H13 UNL     1      -4.886   1.342  -1.370  1.00  0.00           H  
HETATM   33  H14 UNL     1      -4.027   2.360  -0.150  1.00  0.00           H  
HETATM   34  H15 UNL     1      -3.103   1.351  -1.361  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3    6    6
CONECT    3    4   23
CONECT    4    5    5   24
CONECT    5    6
CONECT    6    7
CONECT    7    8   25   26
CONECT    8    9
CONECT    9   10   27   28
CONECT   10   11   29   30
CONECT   11   12   12
CONECT   12   13   16
CONECT   13   14   31
CONECT   14   15   15   15
CONECT   16   17   18
CONECT   17   32   33   34
CONECT   18   19   19
END

HMDB0255201
     RDKit          3D
N-Nitrosocimetidine
 34 34  0  0  0  0  0  0  0  0999 V2000
    5.1071    1.3435    0.3028 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4327    0.0771   -0.1311 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9614   -1.1306   -0.3182 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0270   -2.0415   -0.6141 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8278   -1.3673   -0.6101 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0187   -0.0874   -0.3281 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2410    1.1554   -0.4361 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9999    1.5333    0.6049 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5853    0.8573    0.8537 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9497   -0.2565   -0.0884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0778   -0.9234    0.3240 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3027   -0.7953    0.4609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0116   -2.0065    1.0166 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1871   -3.0868    0.1653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3121   -3.9697   -0.5819 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1228    0.2658    0.1494 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9521    1.3869   -0.7207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4511    0.3003    0.8149 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5518    0.4606    2.0204 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6755    1.7882   -0.4884 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2935    2.0776    0.5751 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6375    1.2067    1.2863 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0089   -1.3920   -0.3025 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1553   -3.1149   -0.8753 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7325    0.9762   -1.5515 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8817    2.0548   -0.7355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7578    0.5112    1.9257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3460    1.7228    0.6892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0600    0.2090   -1.1475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0188   -0.8766   -0.2551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2979   -1.9315    1.9899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8857    1.3424   -1.3696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0273    2.3601   -0.1499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1029    1.3509   -1.3609 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  3
 12 13  1  0
 13 14  1  0
 14 15  3  0
 12 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
  6  2  2  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  4 24  1  0
  7 25  1  0
  7 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 13 31  1  0
 17 32  1  0
 17 33  1  0
 17 34  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Nitrosocimetidine	HMDB

Chemical Formula

C₁₀H₁₅N₇OS

Average Molecular Weight

281.34

Monoisotopic Molecular Weight

281.105879305

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

CN(N=O)C(NC#N)=NCCSCC1=C(C)NC=N1

InChI Identifier

InChI=1S/C10H15N7OS/c1-8-9(15-7-14-8)5-19-4-3-12-10(13-6-11)17(2)16-18/h7H,3-5H2,1-2H3,(H,12,13)(H,14,15)

InChI Key

LFTUYYPQNCJQGN-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
Organic n-nitroso compound
Guanidine
Organic nitroso compound
Thioether
Carboximidamide
Sulfenyl compound
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Dialkylthioether
Azacycle
Organosulfur compound
Organic nitrogen compound
Organonitrogen compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

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	1.08	ALOGPS
logP	0.39	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	13.38	ChemAxon
pKa (Strongest Basic)	6.91	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	109.53 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	75.67 m³·mol⁻¹	ChemAxon
Polarizability	28.99 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
DeepCCS	[M+H]+	155.571	30932474
DeepCCS	[M-H]-	153.213	30932474
DeepCCS	[M-2H]-	186.464	30932474
DeepCCS	[M+Na]+	161.664	30932474
AllCCS	[M+H]+	161.9	32859911
AllCCS	[M+H-H2O]+	158.8	32859911
AllCCS	[M+NH4]+	164.8	32859911
AllCCS	[M+Na]+	165.6	32859911
AllCCS	[M-H]-	163.2	32859911
AllCCS	[M+Na-2H]-	163.6	32859911
AllCCS	[M+HCOO]-	164.0	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	9.6939 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	4.44 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	511.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	246.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	70.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	166.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	46.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	290.6 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	316.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	742.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	630.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	79.0 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	888.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	181.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	188.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	583.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	447.0 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	215.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-Nitrosocimetidine	CN(N=O)C(NC#N)=NCCSCC1=C(C)NC=N1	3016.5	Standard polar	33892256
N-Nitrosocimetidine	CN(N=O)C(NC#N)=NCCSCC1=C(C)NC=N1	2281.1	Standard non polar	33892256
N-Nitrosocimetidine	CN(N=O)C(NC#N)=NCCSCC1=C(C)NC=N1	3044.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N-Nitrosocimetidine,1TMS,isomer #1	CC1=C(CSCCN=C(N(C)N=O)N(C#N)[Si](C)(C)C)N=C[NH]1	2787.0	Semi standard non polar	33892256
N-Nitrosocimetidine,1TMS,isomer #1	CC1=C(CSCCN=C(N(C)N=O)N(C#N)[Si](C)(C)C)N=C[NH]1	2327.6	Standard non polar	33892256
N-Nitrosocimetidine,1TMS,isomer #1	CC1=C(CSCCN=C(N(C)N=O)N(C#N)[Si](C)(C)C)N=C[NH]1	4513.1	Standard polar	33892256
N-Nitrosocimetidine,1TMS,isomer #2	CC1=C(CSCCN=C(NC#N)N(C)N=O)N=CN1[Si](C)(C)C	2903.7	Semi standard non polar	33892256
N-Nitrosocimetidine,1TMS,isomer #2	CC1=C(CSCCN=C(NC#N)N(C)N=O)N=CN1[Si](C)(C)C	2320.9	Standard non polar	33892256
N-Nitrosocimetidine,1TMS,isomer #2	CC1=C(CSCCN=C(NC#N)N(C)N=O)N=CN1[Si](C)(C)C	4944.2	Standard polar	33892256
N-Nitrosocimetidine,2TMS,isomer #1	CC1=C(CSCCN=C(N(C)N=O)N(C#N)[Si](C)(C)C)N=CN1[Si](C)(C)C	2761.0	Semi standard non polar	33892256
N-Nitrosocimetidine,2TMS,isomer #1	CC1=C(CSCCN=C(N(C)N=O)N(C#N)[Si](C)(C)C)N=CN1[Si](C)(C)C	2416.2	Standard non polar	33892256
N-Nitrosocimetidine,2TMS,isomer #1	CC1=C(CSCCN=C(N(C)N=O)N(C#N)[Si](C)(C)C)N=CN1[Si](C)(C)C	4385.1	Standard polar	33892256
N-Nitrosocimetidine,1TBDMS,isomer #1	CC1=C(CSCCN=C(N(C)N=O)N(C#N)[Si](C)(C)C(C)(C)C)N=C[NH]1	2960.0	Semi standard non polar	33892256
N-Nitrosocimetidine,1TBDMS,isomer #1	CC1=C(CSCCN=C(N(C)N=O)N(C#N)[Si](C)(C)C(C)(C)C)N=C[NH]1	2506.0	Standard non polar	33892256
N-Nitrosocimetidine,1TBDMS,isomer #1	CC1=C(CSCCN=C(N(C)N=O)N(C#N)[Si](C)(C)C(C)(C)C)N=C[NH]1	4474.7	Standard polar	33892256
N-Nitrosocimetidine,1TBDMS,isomer #2	CC1=C(CSCCN=C(NC#N)N(C)N=O)N=CN1[Si](C)(C)C(C)(C)C	3088.1	Semi standard non polar	33892256
N-Nitrosocimetidine,1TBDMS,isomer #2	CC1=C(CSCCN=C(NC#N)N(C)N=O)N=CN1[Si](C)(C)C(C)(C)C	2501.7	Standard non polar	33892256
N-Nitrosocimetidine,1TBDMS,isomer #2	CC1=C(CSCCN=C(NC#N)N(C)N=O)N=CN1[Si](C)(C)C(C)(C)C	4948.7	Standard polar	33892256
N-Nitrosocimetidine,2TBDMS,isomer #1	CC1=C(CSCCN=C(N(C)N=O)N(C#N)[Si](C)(C)C(C)(C)C)N=CN1[Si](C)(C)C(C)(C)C	3098.4	Semi standard non polar	33892256
N-Nitrosocimetidine,2TBDMS,isomer #1	CC1=C(CSCCN=C(N(C)N=O)N(C#N)[Si](C)(C)C(C)(C)C)N=CN1[Si](C)(C)C(C)(C)C	2750.7	Standard non polar	33892256
N-Nitrosocimetidine,2TBDMS,isomer #1	CC1=C(CSCCN=C(N(C)N=O)N(C#N)[Si](C)(C)C(C)(C)C)N=CN1[Si](C)(C)C(C)(C)C	4331.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - N-Nitrosocimetidine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0005-9310000000-86557702bc2b8dedfc3b	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Nitrosocimetidine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	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

47424

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

52445

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for N-Nitrosocimetidine (HMDB0255201)

MOL for HMDB0255201 (N-Nitrosocimetidine)

3D MOL for HMDB0255201 (N-Nitrosocimetidine)

3D SDF for HMDB0255201 (N-Nitrosocimetidine)

3D-SDF for HMDB0255201 (N-Nitrosocimetidine)

PDB for HMDB0255201 (N-Nitrosocimetidine)

3D PDB for HMDB0255201 (N-Nitrosocimetidine)

SMILES for HMDB0255201 (N-Nitrosocimetidine)

INCHI for HMDB0255201 (N-Nitrosocimetidine)

Structure for HMDB0255201 (N-Nitrosocimetidine)

3D Structure for HMDB0255201 (N-Nitrosocimetidine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra