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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1)transporters (1) Show 2 proteins XML

enzymes (1)transporters (1) Show 2 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2020-02-26 21:41:21 UTC

HMDB ID

HMDB0015301

Secondary Accession Numbers

HMDB15301

Metabolite Identification

Common Name

Guanethidine

Description

Guanethidine, also known as octadine or ismelin, belongs to the class of organic compounds known as guanidines. Guanidines are compounds containing a guanidine moiety, with the general structure (R1R2N)(R3R4N)C=N-R5. Guanethidine is a drug which is used for the treatment of moderate and severe hypertension, either alone or as an adjunct, and for the treatment of renal hypertension. Side effects include postural and exercise hypotension, sexual dysfunction (delayed or retrograde ejaculation), and diarrhea.Guanethidine is transported by uptake 1 into the presynaptic terminal transported by norepinephrine transporter (NET). Guanethidine is a very strong basic compound (based on its pKa). Guanethidine is transported across the sympathetic nerve membrane by the same mechanism that transports norepinephrine itself (NET, uptake 1), and uptake is essential for the drug's action. Spontaneous release is not affected.Guanethidine was once a mainstay for hypertension resistant to other agents, and was often used safely during pregnancy, but it is no longer used in the US due to lack of availability. Once inside the terminal it blocks the release of norepinephrine in response to arrival of an action potential. It becomes concentrated in norepinephrine transmitter vesicles, replacing norepinephrine in these vesicles. It is still licensed in some countries, e.g., UK, for the rapid control of blood pressure in a hypertensive emergency. It may also inhibit the release of granules by decreasing norepinephrine. Intravenous nerve block (Bier block) using guanethidine has been used to treat chronic pain caused by complex regional pain syndrome. Once guanethidine has entered the nerve, it is concentrated in transmitter vesicles, where it replaces norepinephrine. This leads to a gradual depletion of norepinephrine stores in the nerve endings. Guanethidine is an antihypertensive drug that reduces the release of catecholamines, such as norepinephrine.

Structure

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

HMDB0015301
     RDKit          3D
Guanethidine
 36 36  0  0  0  0  0  0  0  0999 V2000
    4.1232    1.1767   -0.9083 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3884    0.1251    0.0020 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7242   -0.2739    0.2452 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3968   -0.4431    0.5872 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0247   -0.0281    0.3324 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0922   -1.0858    0.8094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2943   -0.8410    0.6322 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6942   -0.8423   -0.7216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0109   -1.1441   -1.2599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2967   -0.5878   -0.9462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6980    0.8148   -0.7215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1379    1.4330    0.6110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9692    0.6700    0.7861 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7737    0.3220    1.4460 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0599    2.1921   -0.6025 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9720    1.0306   -1.9381 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9859   -1.2525    0.5027 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5482    0.3921    0.1825 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9578    0.1630   -0.7633 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9026    0.9131    0.9190 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3332   -2.0190    0.2378 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3706   -1.3175    1.8694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0373   -1.7060   -1.1238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1700   -0.0307   -1.3374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1711   -2.2710   -1.1308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8352   -1.1045   -2.3889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9641   -0.8521   -1.8536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9010   -1.2041   -0.1910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7784    0.8530   -0.6266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3073    1.4247   -1.5822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9399    1.3936    1.3893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0180    2.5094    0.3680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4799   -0.3333    0.9021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4963    0.9308   -0.2083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0262    1.1067    1.5085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8800   -0.1138    2.4712 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14  7  1  0
  1 15  1  0
  1 16  1  0
  3 17  1  0
  3 18  1  0
  5 19  1  0
  5 20  1  0
  6 21  1  0
  6 22  1  0
  8 23  1  0
  8 24  1  0
  9 25  1  0
  9 26  1  0
 10 27  1  0
 10 28  1  0
 11 29  1  0
 11 30  1  0
 12 31  1  0
 12 32  1  0
 13 33  1  0
 13 34  1  0
 14 35  1  0
 14 36  1  0
M  END

HMDB0015301
     RDKit          3D
Guanethidine
 36 36  0  0  0  0  0  0  0  0999 V2000
    4.1232    1.1767   -0.9083 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3884    0.1251    0.0020 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7242   -0.2739    0.2452 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3968   -0.4431    0.5872 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0247   -0.0281    0.3324 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0922   -1.0858    0.8094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2943   -0.8410    0.6322 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6942   -0.8423   -0.7216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0109   -1.1441   -1.2599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2967   -0.5878   -0.9462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6980    0.8148   -0.7215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1379    1.4330    0.6110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9692    0.6700    0.7861 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7737    0.3220    1.4460 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0599    2.1921   -0.6025 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9720    1.0306   -1.9381 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9859   -1.2525    0.5027 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5482    0.3921    0.1825 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9578    0.1630   -0.7633 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9026    0.9131    0.9190 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3332   -2.0190    0.2378 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3706   -1.3175    1.8694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0373   -1.7060   -1.1238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1700   -0.0307   -1.3374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1711   -2.2710   -1.1308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8352   -1.1045   -2.3889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9641   -0.8521   -1.8536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9010   -1.2041   -0.1910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7784    0.8530   -0.6266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3073    1.4247   -1.5822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9399    1.3936    1.3893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0180    2.5094    0.3680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4799   -0.3333    0.9021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4963    0.9308   -0.2083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0262    1.1067    1.5085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8800   -0.1138    2.4712 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14  7  1  0
  1 15  1  0
  1 16  1  0
  3 17  1  0
  3 18  1  0
  5 19  1  0
  5 20  1  0
  6 21  1  0
  6 22  1  0
  8 23  1  0
  8 24  1  0
  9 25  1  0
  9 26  1  0
 10 27  1  0
 10 28  1  0
 11 29  1  0
 11 30  1  0
 12 31  1  0
 12 32  1  0
 13 33  1  0
 13 34  1  0
 14 35  1  0
 14 36  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1170                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  N   UNK     0       5.884   1.876   0.000  0.00  0.00           N+0
HETATM    2  N   UNK     0       6.126  -2.192   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0       5.778  -4.836   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0       3.661  -3.212   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       4.344   1.876   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.973   2.965   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.255   2.965   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.973   4.505   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.255   4.505   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.884   5.594   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.344   5.594   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.474   0.453   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.536  -0.769   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.188  -3.413   0.000  0.00  0.00           C+0
CONECT    1    5    6   12                                                  
CONECT    2   13   14                                                       
CONECT    3   14                                                            
CONECT    4   14                                                            
CONECT    5    1    7                                                       
CONECT    6    1    8                                                       
CONECT    7    5    9                                                       
CONECT    8    6   10                                                       
CONECT    9    7   11                                                       
CONECT   10    8   11                                                       
CONECT   11    9   10                                                       
CONECT   12    1   13                                                       
CONECT   13    2   12                                                       
CONECT   14    2    3    4                                                  
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

COMPND    HMDB0015301
HETATM    1  N1  UNL     1       4.123   1.177  -0.908  1.00  0.00           N  
HETATM    2  C1  UNL     1       4.388   0.125   0.002  1.00  0.00           C  
HETATM    3  N2  UNL     1       5.724  -0.274   0.245  1.00  0.00           N  
HETATM    4  N3  UNL     1       3.397  -0.443   0.587  1.00  0.00           N  
HETATM    5  C2  UNL     1       2.025  -0.028   0.332  1.00  0.00           C  
HETATM    6  C3  UNL     1       1.092  -1.086   0.809  1.00  0.00           C  
HETATM    7  N4  UNL     1      -0.294  -0.841   0.632  1.00  0.00           N  
HETATM    8  C4  UNL     1      -0.694  -0.842  -0.722  1.00  0.00           C  
HETATM    9  C5  UNL     1      -2.011  -1.144  -1.260  1.00  0.00           C  
HETATM   10  C6  UNL     1      -3.297  -0.588  -0.946  1.00  0.00           C  
HETATM   11  C7  UNL     1      -3.698   0.815  -0.721  1.00  0.00           C  
HETATM   12  C8  UNL     1      -3.138   1.433   0.611  1.00  0.00           C  
HETATM   13  C9  UNL     1      -1.969   0.670   0.786  1.00  0.00           C  
HETATM   14  C10 UNL     1      -0.774   0.322   1.446  1.00  0.00           C  
HETATM   15  H1  UNL     1       4.060   2.192  -0.602  1.00  0.00           H  
HETATM   16  H2  UNL     1       3.972   1.031  -1.938  1.00  0.00           H  
HETATM   17  H3  UNL     1       5.986  -1.253   0.503  1.00  0.00           H  
HETATM   18  H4  UNL     1       6.548   0.392   0.183  1.00  0.00           H  
HETATM   19  H5  UNL     1       1.958   0.163  -0.763  1.00  0.00           H  
HETATM   20  H6  UNL     1       1.903   0.913   0.919  1.00  0.00           H  
HETATM   21  H7  UNL     1       1.333  -2.019   0.238  1.00  0.00           H  
HETATM   22  H8  UNL     1       1.371  -1.318   1.869  1.00  0.00           H  
HETATM   23  H9  UNL     1      -0.037  -1.706  -1.124  1.00  0.00           H  
HETATM   24  H10 UNL     1      -0.170  -0.031  -1.337  1.00  0.00           H  
HETATM   25  H11 UNL     1      -2.171  -2.271  -1.131  1.00  0.00           H  
HETATM   26  H12 UNL     1      -1.835  -1.104  -2.389  1.00  0.00           H  
HETATM   27  H13 UNL     1      -3.964  -0.852  -1.854  1.00  0.00           H  
HETATM   28  H14 UNL     1      -3.901  -1.204  -0.191  1.00  0.00           H  
HETATM   29  H15 UNL     1      -4.778   0.853  -0.627  1.00  0.00           H  
HETATM   30  H16 UNL     1      -3.307   1.425  -1.582  1.00  0.00           H  
HETATM   31  H17 UNL     1      -3.940   1.394   1.389  1.00  0.00           H  
HETATM   32  H18 UNL     1      -3.018   2.509   0.368  1.00  0.00           H  
HETATM   33  H19 UNL     1      -2.480  -0.333   0.902  1.00  0.00           H  
HETATM   34  H20 UNL     1      -1.496   0.931  -0.208  1.00  0.00           H  
HETATM   35  H21 UNL     1      -0.026   1.107   1.508  1.00  0.00           H  
HETATM   36  H22 UNL     1      -0.880  -0.114   2.471  1.00  0.00           H  
CONECT    1    2   15   16
CONECT    2    3    4    4
CONECT    3   17   18
CONECT    4    5
CONECT    5    6   19   20
CONECT    6    7   21   22
CONECT    7    8   14
CONECT    8    9   23   24
CONECT    9   10   25   26
CONECT   10   11   27   28
CONECT   11   12   29   30
CONECT   12   13   31   32
CONECT   13   14   33   34
CONECT   14   35   36
END

HMDB0015301
     RDKit          3D
Guanethidine
 36 36  0  0  0  0  0  0  0  0999 V2000
    4.1232    1.1767   -0.9083 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3884    0.1251    0.0020 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7242   -0.2739    0.2452 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3968   -0.4431    0.5872 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0247   -0.0281    0.3324 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0922   -1.0858    0.8094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2943   -0.8410    0.6322 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6942   -0.8423   -0.7216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0109   -1.1441   -1.2599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2967   -0.5878   -0.9462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6980    0.8148   -0.7215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1379    1.4330    0.6110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9692    0.6700    0.7861 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7737    0.3220    1.4460 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0599    2.1921   -0.6025 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9720    1.0306   -1.9381 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9859   -1.2525    0.5027 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5482    0.3921    0.1825 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9578    0.1630   -0.7633 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9026    0.9131    0.9190 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3332   -2.0190    0.2378 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3706   -1.3175    1.8694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0373   -1.7060   -1.1238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1700   -0.0307   -1.3374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1711   -2.2710   -1.1308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8352   -1.1045   -2.3889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9641   -0.8521   -1.8536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9010   -1.2041   -0.1910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7784    0.8530   -0.6266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3073    1.4247   -1.5822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9399    1.3936    1.3893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0180    2.5094    0.3680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4799   -0.3333    0.9021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4963    0.9308   -0.2083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0262    1.1067    1.5085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8800   -0.1138    2.4712 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14  7  1  0
  1 15  1  0
  1 16  1  0
  3 17  1  0
  3 18  1  0
  5 19  1  0
  5 20  1  0
  6 21  1  0
  6 22  1  0
  8 23  1  0
  8 24  1  0
  9 25  1  0
  9 26  1  0
 10 27  1  0
 10 28  1  0
 11 29  1  0
 11 30  1  0
 12 31  1  0
 12 32  1  0
 13 33  1  0
 13 34  1  0
 14 35  1  0
 14 36  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(2-(Octahydro-1-azocinyl)ethyl)guanidine	ChEBI
2-(1'-Azacyclooctyl)ethylguanidine	ChEBI
2-(1-N,N-Heptamethyleneimino)ethylguanidine	ChEBI
Guanethidinum	ChEBI
Guanetidina	ChEBI
N-(2-Perhydroazocin-1-ylethyl)guanidine	ChEBI
Guanethidine monosulfate	HMDB
Guanethidine monosulphate	HMDB
Guanethidine sulphae	HMDB
Guanethidine sulfate (1:1)	HMDB
Guanethidine sulfate (2:1), 14C-labeled	HMDB
Octadine	HMDB
Oktadin	HMDB
monoSulfate, guanethidine	HMDB
Guanethidine sulfate	HMDB
Guanethidine sulfate (1:2)	HMDB
Guanethidine sulfate (2:1)	HMDB
Ismelin	HMDB
Isobarin	HMDB
((2-Hexahydro-1(2H)-azocinyl)ethyl)guanidine	HMDB
Sulfate, guanethidine	HMDB

Chemical Formula

C₁₀H₂₂N₄

Average Molecular Weight

198.3085

Monoisotopic Molecular Weight

198.184446724

IUPAC Name

2-[2-(azocan-1-yl)ethyl]guanidine

Traditional Name

ismelin

CAS Registry Number

645-43-2

SMILES

NC(N)=NCCN1CCCCCCC1

InChI Identifier

InChI=1S/C10H22N4/c11-10(12)13-6-9-14-7-4-2-1-3-5-8-14/h1-9H2,(H4,11,12,13)

InChI Key

ACGDKVXYNVEAGU-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as guanidines. Guanidines are compounds containing a guanidine moiety, with the general structure (R1R2N)(R3R4N)C=N-R5.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Guanidines

Direct Parent

Guanidines

Alternative Parents

Substituents

Tertiary aliphatic amine
Tertiary amine
Guanidine
Azacycle
Organoheterocyclic compound
Carboximidamide
Organopnictogen compound
Hydrocarbon derivative
Imine
Amine
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

guanidines (CHEBI:5557 )
azocanes (CHEBI:5557 )

Ontology

Disposition

Biological location

Excreta

Urine

Cellular substructure

Macromolecular complex

Blood

Ingestion

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	250 °C (sulfate salt)	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	2.25 g/L	Not Available
LogP	0.8	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	144.236	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000703

Predicted Molecular Properties

Property	Value	Source
Water Solubility	2.25 g/L	ALOGPS
logP	10^(0.89) g/L	ALOGPS
logP	10^(0.74) g/L	ChemAxon
logS	10^(-2) g/L	ALOGPS
pKa (Strongest Basic)	11.77	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	67.64 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	59.7 m³·mol⁻¹	ChemAxon
Polarizability	23.67 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]+	146.617	31661259
DarkChem	[M-H]-	142.68	31661259
DeepCCS	[M+H]+	151.804	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Guanethidine	NC(N)=NCCN1CCCCCCC1	2786.6	Standard polar	33892256
Guanethidine	NC(N)=NCCN1CCCCCCC1	1675.9	Standard non polar	33892256
Guanethidine	NC(N)=NCCN1CCCCCCC1	1949.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Guanethidine,1TMS,isomer #1	C[Si](C)(C)NC(N)=NCCN1CCCCCCC1	2056.5	Semi standard non polar	33892256
Guanethidine,1TMS,isomer #1	C[Si](C)(C)NC(N)=NCCN1CCCCCCC1	1849.1	Standard non polar	33892256
Guanethidine,1TMS,isomer #1	C[Si](C)(C)NC(N)=NCCN1CCCCCCC1	3375.7	Standard polar	33892256
Guanethidine,2TMS,isomer #1	C[Si](C)(C)NC(=NCCN1CCCCCCC1)N[Si](C)(C)C	2184.8	Semi standard non polar	33892256
Guanethidine,2TMS,isomer #1	C[Si](C)(C)NC(=NCCN1CCCCCCC1)N[Si](C)(C)C	1924.0	Standard non polar	33892256
Guanethidine,2TMS,isomer #1	C[Si](C)(C)NC(=NCCN1CCCCCCC1)N[Si](C)(C)C	3422.7	Standard polar	33892256
Guanethidine,2TMS,isomer #2	C[Si](C)(C)N(C(N)=NCCN1CCCCCCC1)[Si](C)(C)C	2126.8	Semi standard non polar	33892256
Guanethidine,2TMS,isomer #2	C[Si](C)(C)N(C(N)=NCCN1CCCCCCC1)[Si](C)(C)C	2034.6	Standard non polar	33892256
Guanethidine,2TMS,isomer #2	C[Si](C)(C)N(C(N)=NCCN1CCCCCCC1)[Si](C)(C)C	3393.8	Standard polar	33892256
Guanethidine,3TMS,isomer #1	C[Si](C)(C)NC(=NCCN1CCCCCCC1)N([Si](C)(C)C)[Si](C)(C)C	2181.3	Semi standard non polar	33892256
Guanethidine,3TMS,isomer #1	C[Si](C)(C)NC(=NCCN1CCCCCCC1)N([Si](C)(C)C)[Si](C)(C)C	2123.3	Standard non polar	33892256
Guanethidine,3TMS,isomer #1	C[Si](C)(C)NC(=NCCN1CCCCCCC1)N([Si](C)(C)C)[Si](C)(C)C	3171.5	Standard polar	33892256
Guanethidine,4TMS,isomer #1	C[Si](C)(C)N(C(=NCCN1CCCCCCC1)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2256.9	Semi standard non polar	33892256
Guanethidine,4TMS,isomer #1	C[Si](C)(C)N(C(=NCCN1CCCCCCC1)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2298.5	Standard non polar	33892256
Guanethidine,4TMS,isomer #1	C[Si](C)(C)N(C(=NCCN1CCCCCCC1)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2837.1	Standard polar	33892256
Guanethidine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(N)=NCCN1CCCCCCC1	2245.8	Semi standard non polar	33892256
Guanethidine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(N)=NCCN1CCCCCCC1	2051.8	Standard non polar	33892256
Guanethidine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(N)=NCCN1CCCCCCC1	3538.6	Standard polar	33892256
Guanethidine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=NCCN1CCCCCCC1)N[Si](C)(C)C(C)(C)C	2568.1	Semi standard non polar	33892256
Guanethidine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=NCCN1CCCCCCC1)N[Si](C)(C)C(C)(C)C	2351.6	Standard non polar	33892256
Guanethidine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=NCCN1CCCCCCC1)N[Si](C)(C)C(C)(C)C	3462.3	Standard polar	33892256
Guanethidine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C(N)=NCCN1CCCCCCC1)[Si](C)(C)C(C)(C)C	2491.7	Semi standard non polar	33892256
Guanethidine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C(N)=NCCN1CCCCCCC1)[Si](C)(C)C(C)(C)C	2433.3	Standard non polar	33892256
Guanethidine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C(N)=NCCN1CCCCCCC1)[Si](C)(C)C(C)(C)C	3567.9	Standard polar	33892256
Guanethidine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=NCCN1CCCCCCC1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2765.8	Semi standard non polar	33892256
Guanethidine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=NCCN1CCCCCCC1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2730.3	Standard non polar	33892256
Guanethidine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=NCCN1CCCCCCC1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3231.1	Standard polar	33892256
Guanethidine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=NCCN1CCCCCCC1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3046.5	Semi standard non polar	33892256
Guanethidine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=NCCN1CCCCCCC1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3049.6	Standard non polar	33892256
Guanethidine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=NCCN1CCCCCCC1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3035.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Guanethidine GC-MS (Non-derivatized) - 70eV, Positive	splash10-05dl-9800000000-92577f077502658eda15	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Guanethidine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Guanethidine LC-ESI-QQ , positive-QTOF	splash10-0002-0900000000-63bf143534cccc53e099	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Guanethidine LC-ESI-QQ , positive-QTOF	splash10-000g-3900000000-b0c1213301460e6159e2	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Guanethidine LC-ESI-QQ , positive-QTOF	splash10-000f-8900000000-a1d8b2ab68936ac02c48	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Guanethidine LC-ESI-QQ , positive-QTOF	splash10-007c-9200000000-091425f6c0c880a5afdd	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Guanethidine LC-ESI-QQ , positive-QTOF	splash10-0a4r-9000000000-3d40142c51842fbbf5fc	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Guanethidine 10V, Positive-QTOF	splash10-0002-2900000000-3c0d9ad535e10192de33	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Guanethidine 20V, Positive-QTOF	splash10-01pc-9800000000-f1d0a92cd4e7f5d5da78	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Guanethidine 40V, Positive-QTOF	splash10-03di-9200000000-7f351fa76ffff520f407	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Guanethidine 10V, Negative-QTOF	splash10-0a4j-2900000000-85cc5b54f54b4d66b7d7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Guanethidine 20V, Negative-QTOF	splash10-0a4i-2900000000-5456c549767554136a2a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Guanethidine 40V, Negative-QTOF	splash10-052f-9100000000-72d038e0b4bab6976722	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Guanethidine 10V, Positive-QTOF	splash10-0002-0900000000-ef3ffa4801d71aa44093	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Guanethidine 20V, Positive-QTOF	splash10-0006-2900000000-71e448522ec8b2788ede	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Guanethidine 40V, Positive-QTOF	splash10-03dl-6900000000-7f013e5325db2e146174	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Guanethidine 10V, Negative-QTOF	splash10-0udj-0900000000-364208ae432e6172afa5	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Guanethidine 20V, Negative-QTOF	splash10-0udi-0900000000-661b5d94a8a02cdcfc2a	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Guanethidine 40V, Negative-QTOF	splash10-006x-4900000000-936412e2b075cbd2a91e	2021-10-11	Wishart Lab	View Spectrum

NMR Spectra

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

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

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 DB01170	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01170	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01170

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

3398

KEGG Compound ID

C07036

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Guanethidine

METLIN ID

Not Available

PubChem Compound

3518

PDB ID

Not Available

ChEBI ID

5557

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. 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 ]

Transporters

Enzyme Details

1. Sodium-dependent noradrenaline transporter

General function:: Involved in neurotransmitter:sodium symporter activity
Specific function:: Amine transporter. Terminates the action of noradrenaline by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name:: SLC6A2
Uniprot ID:: P23975
Molecular weight:: 69331.42

References

Joyce PI, Atcheson R, Marcus RJ, Heffernan AM, Rowbotham DJ, Lambert DG: Interaction of local anaesthetic agents with the endogenous norepinephrine transporter in SH-SY5Y human neuroblastoma cells. Neurosci Lett. 2001 Jun 15;305(3):161-4. [PubMed:11403930 ]
Yi E, Love JA: Alpha-adrenergic modulation of synaptic transmission in rabbit pancreatic ganglia. Auton Neurosci. 2005 Oct 30;122(1-2):45-57. Epub 2005 Aug 25. [PubMed:16126010 ]
Galli A, Blakely RD, DeFelice LJ: Norepinephrine transporters have channel modes of conduction. Proc Natl Acad Sci U S A. 1996 Aug 6;93(16):8671-6. [PubMed:8710929 ]

Showing metabocard for Guanethidine (HMDB0015301)

MOL for HMDB0015301 (Guanethidine)

3D MOL for HMDB0015301 (Guanethidine)

3D SDF for HMDB0015301 (Guanethidine)

3D-SDF for HMDB0015301 (Guanethidine)

PDB for HMDB0015301 (Guanethidine)

3D PDB for HMDB0015301 (Guanethidine)

SMILES for HMDB0015301 (Guanethidine)

INCHI for HMDB0015301 (Guanethidine)

Structure for HMDB0015301 (Guanethidine)

3D Structure for HMDB0015301 (Guanethidine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

References

Transporters

References