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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 19:39:57 UTC

Update Date

2021-09-26 23:15:05 UTC

HMDB ID

HMDB0258290

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Siguazodan

Description

N'-cyano-N-[4-(6-hydroxy-4-methyl-4,5-dihydropyridazin-3-yl)phenyl]-N''-methylguanidine belongs to the class of organic compounds known as pyridazines and derivatives. Pyridazines and derivatives are compounds containing a pyridazine ring, which is a six-member aromatic ring containing two nitrogen atoms at positions 1 and 2, and four carbon atoms. Based on a literature review very few articles have been published on N'-cyano-N-[4-(6-hydroxy-4-methyl-4,5-dihydropyridazin-3-yl)phenyl]-N''-methylguanidine. This compound has been identified in human blood as reported by (PMID: 31557052 ). Siguazodan is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Siguazodan 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

HMDB0258290
     RDKit          3D
Siguazodan
 37 38  0  0  0  0  0  0  0  0999 V2000
   -5.5402   -1.7984    0.7581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6654   -1.5632   -0.3596 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0272   -0.4409   -0.4102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1680    0.5524    0.5991 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0252    1.9017    0.2618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8924    3.0295   -0.0210 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1724   -0.2445   -1.5293 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7728   -0.0649   -1.2941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9181    0.1288   -2.3711 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4247    0.3025   -2.1666 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9726    0.2916   -0.8950 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4172    0.4883   -0.6850 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1517    0.7018   -1.7149 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5290    0.9030   -1.5959 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1214    0.8907   -0.4680 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5159    1.1064   -0.5191 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4230    0.6751    0.7910 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9728    0.3893    0.6648 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6965   -1.0320    1.1909 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1167    0.0995    0.1606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2560   -0.0799   -0.0244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0292   -2.7875    0.6108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2734   -0.9647    0.7851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9550   -1.8382    1.6904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3763    0.2755    1.5841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5394   -0.2288   -2.5046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3267    0.1407   -3.3740 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1117    0.4555   -2.9935 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1708    0.3676   -0.3394 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5083    1.6467    1.3854 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9180   -0.1370    1.4088 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3505    1.0622    1.3307 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6608   -1.5948    1.2489 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0335   -1.5279    0.4730 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3310   -0.9542    2.2214 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4397    0.0792    1.1908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9282   -0.2311    0.8075 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  3
  3  4  1  0
  4  5  1  0
  5  6  3  0
  3  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 11 20  1  0
 20 21  2  0
 21  8  1  0
 18 12  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  7 26  1  0
  9 27  1  0
 10 28  1  0
 16 29  1  0
 17 30  1  0
 17 31  1  0
 18 32  1  0
 19 33  1  0
 19 34  1  0
 19 35  1  0
 20 36  1  0
 21 37  1  0
M  END


  Mrv1572004221604402D          

 21 22  0  0  0  0            999 V2000
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.8875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  3  1  0  0  0  0
  6  4  2  0  0  0  0
  9  1  1  0  0  0  0
  9  7  1  0  0  0  0
 10  3  2  0  0  0  0
 10  4  1  0  0  0  0
 11  5  2  0  0  0  0
 11  6  1  0  0  0  0
 12  7  1  0  0  0  0
 13  9  1  0  0  0  0
 13 10  1  0  0  0  0
 15  8  3  0  0  0  0
 16  2  1  4  0  0  0
 16 14  2  0  0  0  0
 17  8  1  0  0  0  0
 17 14  1  0  0  0  0
 18 11  1  0  0  0  0
 18 14  1  0  0  0  0
 19 12  2  0  0  0  0
 20 13  2  0  0  0  0
 20 19  1  0  0  0  0
 21 12  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0258290

> <DATABASE_NAME>
hmdb

> <SMILES>
CN=C(NC#N)NC1=CC=C(C=C1)C1=NN=C(O)CC1C

> <INCHI_IDENTIFIER>
InChI=1S/C14H16N6O/c1-9-7-12(21)19-20-13(9)10-3-5-11(6-4-10)18-14(16-2)17-8-15/h3-6,9H,7H2,1-2H3,(H,19,21)(H2,16,17,18)

> <INCHI_KEY>
NUHPODZZKHQQET-UHFFFAOYSA-N

> <FORMULA>
C14H16N6O

> <MOLECULAR_WEIGHT>
284.323

> <EXACT_MASS>
284.138559159

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
30.107270090196607

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N'-cyano-N-[4-(6-hydroxy-4-methyl-4,5-dihydropyridazin-3-yl)phenyl]-N''-methylguanidine

> <ALOGPS_LOGP>
2.10

> <JCHEM_LOGP>
1.4232993203333333

> <ALOGPS_LOGS>
-2.92

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
19.737815565551294

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.9365494002451795

> <JCHEM_PKA_STRONGEST_BASIC>
1.89174173348389

> <JCHEM_POLAR_SURFACE_AREA>
105.16

> <JCHEM_REFRACTIVITY>
81.0787

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.41e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N'-cyano-N-[4-(6-hydroxy-4-methyl-4,5-dihydropyridazin-3-yl)phenyl]-N''-methylguanidine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0258290
     RDKit          3D
Siguazodan
 37 38  0  0  0  0  0  0  0  0999 V2000
   -5.5402   -1.7984    0.7581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6654   -1.5632   -0.3596 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0272   -0.4409   -0.4102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1680    0.5524    0.5991 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0252    1.9017    0.2618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8924    3.0295   -0.0210 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1724   -0.2445   -1.5293 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7728   -0.0649   -1.2941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9181    0.1288   -2.3711 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4247    0.3025   -2.1666 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9726    0.2916   -0.8950 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4172    0.4883   -0.6850 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1517    0.7018   -1.7149 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5290    0.9030   -1.5959 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1214    0.8907   -0.4680 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5159    1.1064   -0.5191 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4230    0.6751    0.7910 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9728    0.3893    0.6648 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6965   -1.0320    1.1909 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1167    0.0995    0.1606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2560   -0.0799   -0.0244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0292   -2.7875    0.6108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2734   -0.9647    0.7851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9550   -1.8382    1.6904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3763    0.2755    1.5841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5394   -0.2288   -2.5046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3267    0.1407   -3.3740 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1117    0.4555   -2.9935 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1708    0.3676   -0.3394 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5083    1.6467    1.3854 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9180   -0.1370    1.4088 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3505    1.0622    1.3307 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6608   -1.5948    1.2489 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0335   -1.5279    0.4730 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3310   -0.9542    2.2214 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4397    0.0792    1.1908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9282   -0.2311    0.8075 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  3
  3  4  1  0
  4  5  1  0
  5  6  3  0
  3  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 11 20  1  0
 20 21  2  0
 21  8  1  0
 18 12  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  7 26  1  0
  9 27  1  0
 10 28  1  0
 16 29  1  0
 17 30  1  0
 17 31  1  0
 18 32  1  0
 19 33  1  0
 19 34  1  0
 19 35  1  0
 20 36  1  0
 21 37  1  0
M  END

HEADER    PROTEIN                                 22-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-APR-16         0                                  
HETATM    1  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       1.334   5.390   0.000  0.00  0.00           N+0
HETATM   16  N   UNK     0       2.667   1.540   0.000  0.00  0.00           N+0
HETATM   17  N   UNK     0       4.001   3.850   0.000  0.00  0.00           N+0
HETATM   18  N   UNK     0       5.335   1.540   0.000  0.00  0.00           N+0
HETATM   19  N   UNK     0       4.001  -6.930   0.000  0.00  0.00           N+0
HETATM   20  N   UNK     0       4.001  -5.390   0.000  0.00  0.00           N+0
HETATM   21  O   UNK     0       5.335  -9.240   0.000  0.00  0.00           O+0
CONECT    1    9                                                            
CONECT    2   16                                                            
CONECT    3    5   10                                                       
CONECT    4    6   10                                                       
CONECT    5    3   11                                                       
CONECT    6    4   11                                                       
CONECT    7    9   12                                                       
CONECT    8   15   17                                                       
CONECT    9    1    7   13                                                  
CONECT   10    3    4   13                                                  
CONECT   11    5    6   18                                                  
CONECT   12    7   19   21                                                  
CONECT   13    9   10   20                                                  
CONECT   14   16   17   18                                                  
CONECT   15    8                                                            
CONECT   16    2   14                                                       
CONECT   17    8   14                                                       
CONECT   18   11   14                                                       
CONECT   19   12   20                                                       
CONECT   20   13   19                                                       
CONECT   21   12                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

COMPND    HMDB0258290
HETATM    1  C1  UNL     1      -5.540  -1.798   0.758  1.00  0.00           C  
HETATM    2  N1  UNL     1      -4.665  -1.563  -0.360  1.00  0.00           N  
HETATM    3  C2  UNL     1      -4.027  -0.441  -0.410  1.00  0.00           C  
HETATM    4  N2  UNL     1      -4.168   0.552   0.599  1.00  0.00           N  
HETATM    5  C3  UNL     1      -4.025   1.902   0.262  1.00  0.00           C  
HETATM    6  N3  UNL     1      -3.892   3.029  -0.021  1.00  0.00           N  
HETATM    7  N4  UNL     1      -3.172  -0.244  -1.529  1.00  0.00           N  
HETATM    8  C4  UNL     1      -1.773  -0.065  -1.294  1.00  0.00           C  
HETATM    9  C5  UNL     1      -0.918   0.129  -2.371  1.00  0.00           C  
HETATM   10  C6  UNL     1       0.425   0.302  -2.167  1.00  0.00           C  
HETATM   11  C7  UNL     1       0.973   0.292  -0.895  1.00  0.00           C  
HETATM   12  C8  UNL     1       2.417   0.488  -0.685  1.00  0.00           C  
HETATM   13  N5  UNL     1       3.152   0.702  -1.715  1.00  0.00           N  
HETATM   14  N6  UNL     1       4.529   0.903  -1.596  1.00  0.00           N  
HETATM   15  C9  UNL     1       5.121   0.891  -0.468  1.00  0.00           C  
HETATM   16  O1  UNL     1       6.516   1.106  -0.519  1.00  0.00           O  
HETATM   17  C10 UNL     1       4.423   0.675   0.791  1.00  0.00           C  
HETATM   18  C11 UNL     1       2.973   0.389   0.665  1.00  0.00           C  
HETATM   19  C12 UNL     1       2.696  -1.032   1.191  1.00  0.00           C  
HETATM   20  C13 UNL     1       0.117   0.099   0.161  1.00  0.00           C  
HETATM   21  C14 UNL     1      -1.256  -0.080  -0.024  1.00  0.00           C  
HETATM   22  H1  UNL     1      -6.029  -2.788   0.611  1.00  0.00           H  
HETATM   23  H2  UNL     1      -6.273  -0.965   0.785  1.00  0.00           H  
HETATM   24  H3  UNL     1      -4.955  -1.838   1.690  1.00  0.00           H  
HETATM   25  H4  UNL     1      -4.376   0.276   1.584  1.00  0.00           H  
HETATM   26  H5  UNL     1      -3.539  -0.229  -2.505  1.00  0.00           H  
HETATM   27  H6  UNL     1      -1.327   0.141  -3.374  1.00  0.00           H  
HETATM   28  H7  UNL     1       1.112   0.455  -2.994  1.00  0.00           H  
HETATM   29  H8  UNL     1       7.171   0.368  -0.339  1.00  0.00           H  
HETATM   30  H9  UNL     1       4.508   1.647   1.385  1.00  0.00           H  
HETATM   31  H10 UNL     1       4.918  -0.137   1.409  1.00  0.00           H  
HETATM   32  H11 UNL     1       2.351   1.062   1.331  1.00  0.00           H  
HETATM   33  H12 UNL     1       3.661  -1.595   1.249  1.00  0.00           H  
HETATM   34  H13 UNL     1       2.034  -1.528   0.473  1.00  0.00           H  
HETATM   35  H14 UNL     1       2.331  -0.954   2.221  1.00  0.00           H  
HETATM   36  H15 UNL     1       0.440   0.079   1.191  1.00  0.00           H  
HETATM   37  H16 UNL     1      -1.928  -0.231   0.808  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3    3
CONECT    3    4    7
CONECT    4    5   25
CONECT    5    6    6    6
CONECT    7    8   26
CONECT    8    9    9   21
CONECT    9   10   27
CONECT   10   11   11   28
CONECT   11   12   20
CONECT   12   13   13   18
CONECT   13   14
CONECT   14   15   15
CONECT   15   16   17
CONECT   16   29
CONECT   17   18   30   31
CONECT   18   19   32
CONECT   19   33   34   35
CONECT   20   21   21   36
CONECT   21   37
END

HMDB0258290
     RDKit          3D
Siguazodan
 37 38  0  0  0  0  0  0  0  0999 V2000
   -5.5402   -1.7984    0.7581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6654   -1.5632   -0.3596 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0272   -0.4409   -0.4102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1680    0.5524    0.5991 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0252    1.9017    0.2618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8924    3.0295   -0.0210 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1724   -0.2445   -1.5293 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7728   -0.0649   -1.2941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9181    0.1288   -2.3711 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4247    0.3025   -2.1666 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9726    0.2916   -0.8950 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4172    0.4883   -0.6850 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1517    0.7018   -1.7149 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5290    0.9030   -1.5959 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1214    0.8907   -0.4680 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5159    1.1064   -0.5191 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4230    0.6751    0.7910 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9728    0.3893    0.6648 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6965   -1.0320    1.1909 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1167    0.0995    0.1606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2560   -0.0799   -0.0244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0292   -2.7875    0.6108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2734   -0.9647    0.7851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9550   -1.8382    1.6904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3763    0.2755    1.5841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5394   -0.2288   -2.5046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3267    0.1407   -3.3740 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1117    0.4555   -2.9935 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1708    0.3676   -0.3394 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5083    1.6467    1.3854 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9180   -0.1370    1.4088 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3505    1.0622    1.3307 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6608   -1.5948    1.2489 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0335   -1.5279    0.4730 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3310   -0.9542    2.2214 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4397    0.0792    1.1908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9282   -0.2311    0.8075 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  3
  3  4  1  0
  4  5  1  0
  5  6  3  0
  3  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 11 20  1  0
 20 21  2  0
 21  8  1  0
 18 12  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  7 26  1  0
  9 27  1  0
 10 28  1  0
 16 29  1  0
 17 30  1  0
 17 31  1  0
 18 32  1  0
 19 33  1  0
 19 34  1  0
 19 35  1  0
 20 36  1  0
 21 37  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
SKF-94836SIguazodan	ChEMBL
2-cyano-1-Methyl-3-(4-(methyl-6-oxo-1,4,5,6-tetrahydropyridazine-3-yl)phenyl)guanidine	MeSH
SK And F 94836	MeSH
SK And F-94836	MeSH

Chemical Formula

C₁₄H₁₆N₆O

Average Molecular Weight

284.323

Monoisotopic Molecular Weight

284.138559159

IUPAC Name

N'-cyano-N-[4-(6-hydroxy-4-methyl-4,5-dihydropyridazin-3-yl)phenyl]-N''-methylguanidine

Traditional Name

N'-cyano-N-[4-(6-hydroxy-4-methyl-4,5-dihydropyridazin-3-yl)phenyl]-N''-methylguanidine

CAS Registry Number

Not Available

SMILES

CN=C(NC#N)NC1=CC=C(C=C1)C1=NN=C(O)CC1C

InChI Identifier

InChI=1S/C14H16N6O/c1-9-7-12(21)19-20-13(9)10-3-5-11(6-4-10)18-14(16-2)17-8-15/h3-6,9H,7H2,1-2H3,(H,19,21)(H2,16,17,18)

InChI Key

NUHPODZZKHQQET-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyridazines and derivatives. Pyridazines and derivatives are compounds containing a pyridazine ring, which is a six-member aromatic ring containing two nitrogen atoms at positions 1 and 2, and four carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazines

Sub Class

Pyridazines and derivatives

Direct Parent

Pyridazines and derivatives

Alternative Parents

Substituents

Monocyclic benzene moiety
Pyridazine
Benzenoid
Guanidine
Carboximidamide
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organic nitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Imine
Organic oxygen 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)

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	2.1	ALOGPS
logP	1.42	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	4.94	ChemAxon
pKa (Strongest Basic)	1.89	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	105.16 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	81.08 m³·mol⁻¹	ChemAxon
Polarizability	30.11 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	162.255	30932474
DeepCCS	[M-H]-	159.897	30932474
DeepCCS	[M-2H]-	193.289	30932474
DeepCCS	[M+Na]+	168.516	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Siguazodan	CN=C(NC#N)NC1=CC=C(C=C1)C1=NN=C(O)CC1C	3858.4	Standard polar	33892256
Siguazodan	CN=C(NC#N)NC1=CC=C(C=C1)C1=NN=C(O)CC1C	2730.5	Standard non polar	33892256
Siguazodan	CN=C(NC#N)NC1=CC=C(C=C1)C1=NN=C(O)CC1C	3192.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Siguazodan,2TMS,isomer #1	CN=C(NC1=CC=C(C2=NN=C(O[Si](C)(C)C)CC2C)C=C1)N(C#N)[Si](C)(C)C	2893.5	Semi standard non polar	33892256
Siguazodan,2TMS,isomer #1	CN=C(NC1=CC=C(C2=NN=C(O[Si](C)(C)C)CC2C)C=C1)N(C#N)[Si](C)(C)C	2611.4	Standard non polar	33892256
Siguazodan,2TMS,isomer #1	CN=C(NC1=CC=C(C2=NN=C(O[Si](C)(C)C)CC2C)C=C1)N(C#N)[Si](C)(C)C	4744.1	Standard polar	33892256
Siguazodan,2TMS,isomer #2	CN=C(NC#N)N(C1=CC=C(C2=NN=C(O[Si](C)(C)C)CC2C)C=C1)[Si](C)(C)C	2766.7	Semi standard non polar	33892256
Siguazodan,2TMS,isomer #2	CN=C(NC#N)N(C1=CC=C(C2=NN=C(O[Si](C)(C)C)CC2C)C=C1)[Si](C)(C)C	2507.0	Standard non polar	33892256
Siguazodan,2TMS,isomer #2	CN=C(NC#N)N(C1=CC=C(C2=NN=C(O[Si](C)(C)C)CC2C)C=C1)[Si](C)(C)C	4804.0	Standard polar	33892256
Siguazodan,2TMS,isomer #3	CN=C(N(C#N)[Si](C)(C)C)N(C1=CC=C(C2=NN=C(O)CC2C)C=C1)[Si](C)(C)C	2828.4	Semi standard non polar	33892256
Siguazodan,2TMS,isomer #3	CN=C(N(C#N)[Si](C)(C)C)N(C1=CC=C(C2=NN=C(O)CC2C)C=C1)[Si](C)(C)C	2660.5	Standard non polar	33892256
Siguazodan,2TMS,isomer #3	CN=C(N(C#N)[Si](C)(C)C)N(C1=CC=C(C2=NN=C(O)CC2C)C=C1)[Si](C)(C)C	4995.6	Standard polar	33892256
Siguazodan,3TMS,isomer #1	CN=C(N(C#N)[Si](C)(C)C)N(C1=CC=C(C2=NN=C(O[Si](C)(C)C)CC2C)C=C1)[Si](C)(C)C	2752.5	Semi standard non polar	33892256
Siguazodan,3TMS,isomer #1	CN=C(N(C#N)[Si](C)(C)C)N(C1=CC=C(C2=NN=C(O[Si](C)(C)C)CC2C)C=C1)[Si](C)(C)C	2587.6	Standard non polar	33892256
Siguazodan,3TMS,isomer #1	CN=C(N(C#N)[Si](C)(C)C)N(C1=CC=C(C2=NN=C(O[Si](C)(C)C)CC2C)C=C1)[Si](C)(C)C	4448.2	Standard polar	33892256
Siguazodan,2TBDMS,isomer #1	CN=C(NC1=CC=C(C2=NN=C(O[Si](C)(C)C(C)(C)C)CC2C)C=C1)N(C#N)[Si](C)(C)C(C)(C)C	3283.7	Semi standard non polar	33892256
Siguazodan,2TBDMS,isomer #1	CN=C(NC1=CC=C(C2=NN=C(O[Si](C)(C)C(C)(C)C)CC2C)C=C1)N(C#N)[Si](C)(C)C(C)(C)C	2920.9	Standard non polar	33892256
Siguazodan,2TBDMS,isomer #1	CN=C(NC1=CC=C(C2=NN=C(O[Si](C)(C)C(C)(C)C)CC2C)C=C1)N(C#N)[Si](C)(C)C(C)(C)C	4736.1	Standard polar	33892256
Siguazodan,2TBDMS,isomer #2	CN=C(NC#N)N(C1=CC=C(C2=NN=C(O[Si](C)(C)C(C)(C)C)CC2C)C=C1)[Si](C)(C)C(C)(C)C	3124.5	Semi standard non polar	33892256
Siguazodan,2TBDMS,isomer #2	CN=C(NC#N)N(C1=CC=C(C2=NN=C(O[Si](C)(C)C(C)(C)C)CC2C)C=C1)[Si](C)(C)C(C)(C)C	2853.0	Standard non polar	33892256
Siguazodan,2TBDMS,isomer #2	CN=C(NC#N)N(C1=CC=C(C2=NN=C(O[Si](C)(C)C(C)(C)C)CC2C)C=C1)[Si](C)(C)C(C)(C)C	4778.4	Standard polar	33892256
Siguazodan,2TBDMS,isomer #3	CN=C(N(C#N)[Si](C)(C)C(C)(C)C)N(C1=CC=C(C2=NN=C(O)CC2C)C=C1)[Si](C)(C)C(C)(C)C	3177.6	Semi standard non polar	33892256
Siguazodan,2TBDMS,isomer #3	CN=C(N(C#N)[Si](C)(C)C(C)(C)C)N(C1=CC=C(C2=NN=C(O)CC2C)C=C1)[Si](C)(C)C(C)(C)C	3030.8	Standard non polar	33892256
Siguazodan,2TBDMS,isomer #3	CN=C(N(C#N)[Si](C)(C)C(C)(C)C)N(C1=CC=C(C2=NN=C(O)CC2C)C=C1)[Si](C)(C)C(C)(C)C	4998.3	Standard polar	33892256
Siguazodan,3TBDMS,isomer #1	CN=C(N(C#N)[Si](C)(C)C(C)(C)C)N(C1=CC=C(C2=NN=C(O[Si](C)(C)C(C)(C)C)CC2C)C=C1)[Si](C)(C)C(C)(C)C	3231.3	Semi standard non polar	33892256
Siguazodan,3TBDMS,isomer #1	CN=C(N(C#N)[Si](C)(C)C(C)(C)C)N(C1=CC=C(C2=NN=C(O[Si](C)(C)C(C)(C)C)CC2C)C=C1)[Si](C)(C)C(C)(C)C	3042.2	Standard non polar	33892256
Siguazodan,3TBDMS,isomer #1	CN=C(N(C#N)[Si](C)(C)C(C)(C)C)N(C1=CC=C(C2=NN=C(O[Si](C)(C)C(C)(C)C)CC2C)C=C1)[Si](C)(C)C(C)(C)C	4387.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Siguazodan GC-MS (Non-derivatized) - 70eV, Positive	splash10-05ra-1390000000-6e45114d49fc7a4a5448	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Siguazodan GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Siguazodan GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Siguazodan GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Siguazodan GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Siguazodan GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Siguazodan GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Siguazodan GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Siguazodan 10V, Positive-QTOF	splash10-00kr-1190000000-095e0fe0d704bc9ca884	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Siguazodan 20V, Positive-QTOF	splash10-00ku-2190000000-46260f52821bb029abff	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Siguazodan 40V, Positive-QTOF	splash10-000x-9210000000-618ac69c139de1eb0616	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Siguazodan 10V, Negative-QTOF	splash10-001i-2090000000-fe5f3e2032c42f2d1def	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Siguazodan 20V, Negative-QTOF	splash10-0006-9070000000-1eaf6a267d43cfc08201	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Siguazodan 40V, Negative-QTOF	splash10-0006-9110000000-0f57cc650340bbbb390a	2016-08-03	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

65101

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

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 Siguazodan (HMDB0258290)

MOL for HMDB0258290 (Siguazodan)

3D MOL for HMDB0258290 (Siguazodan)

3D SDF for HMDB0258290 (Siguazodan)

3D-SDF for HMDB0258290 (Siguazodan)

PDB for HMDB0258290 (Siguazodan)

3D PDB for HMDB0258290 (Siguazodan)

SMILES for HMDB0258290 (Siguazodan)

INCHI for HMDB0258290 (Siguazodan)

Structure for HMDB0258290 (Siguazodan)

3D Structure for HMDB0258290 (Siguazodan)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra