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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2022-03-07 02:51:35 UTC

HMDB ID

HMDB0014371

Secondary Accession Numbers

HMDB14371

Metabolite Identification

Common Name

Guanadrel

Description

Guanadrel is a postganglionic sympathetic adrenergic antagonist that is administered orally to treat hypertension (high blood pressure). It was used in the form of its sulfate (trade name: Hylorel) but has been largely superseded by other antihypertensive agents due to its unpleasant side effect of orthostatic hypotension (i.e. dizziness when standing) (PMID: 6143629 ). Guanadrel both prevents noradrenaline (norepinephrine) release and depletes noradrenaline stores which effectively creates a peripheral sympathetic blockade. This serves to reduce vasoconstriction which subsequently lowers blood pressure (PMID: 3896742 ).

Structure

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

HMDB0014371
     RDKit          3D
Guanadrel
 34 35  0  0  0  0  0  0  0  0999 V2000
    5.1081    0.9752   -0.0603 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0202    0.0672   -0.1250 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8750   -0.9546    0.8454 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1718    0.1932   -1.0822 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0276   -0.6846   -1.2343 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0187   -0.3134   -0.1503 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5736    1.1024   -0.3590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7516    0.9479   -0.7472 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2094   -0.2366   -0.1935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2846   -0.8632   -1.0427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6124   -0.1840   -0.9113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6040    0.8684    0.1871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0744    0.1866    1.4318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6103   -0.0654    1.2404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1146   -1.1098   -0.2233 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9350    0.8518   -0.6894 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1323    1.7842    0.5987 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8579   -0.7324    1.8810 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7777   -1.9698    0.6080 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3108   -1.7512   -1.1676 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6081   -0.5232   -2.2460 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5474   -0.4588    0.8195 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6432    1.6972    0.5973 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1479    1.6200   -1.1566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3512   -1.9508   -0.8563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9558   -0.7556   -2.1034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9559    0.2992   -1.8478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4000   -0.9117   -0.6328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6347    1.2329    0.3316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8880    1.6597   -0.0750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6534   -0.7483    1.6619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2891    0.8787    2.2863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3226   -0.9494    1.8408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0436    0.7980    1.6506 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
  9 15  1  0
 15  6  1  0
 14  9  1  0
  1 16  1  0
  1 17  1  0
  3 18  1  0
  3 19  1  0
  5 20  1  0
  5 21  1  0
  6 22  1  0
  7 23  1  0
  7 24  1  0
 10 25  1  0
 10 26  1  0
 11 27  1  0
 11 28  1  0
 12 29  1  0
 12 30  1  0
 13 31  1  0
 13 32  1  0
 14 33  1  0
 14 34  1  0
M  END

38521
  Mrv0541 02231214322D          

 15 16  0  0  1  0            999 V2000
    3.7850   -0.0593    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7850   -1.3942    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9908   -0.1648    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4120   -0.0155    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5720    1.1406    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3001   -0.7268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8876   -1.4412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8876   -0.0123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -0.0123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -1.4412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.7268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5696   -0.3142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5696   -1.1393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2371    0.1707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6582    0.3201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  1 12  1  0  0  0  0
  2  6  1  0  0  0  0
  2 13  1  0  0  0  0
  3 14  1  0  0  0  0
  3 15  2  0  0  0  0
  4 15  1  0  0  0  0
  5 15  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  7 10  1  0  0  0  0
  8  9  1  0  0  0  0
  9 11  1  0  0  0  0
 10 11  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014371

> <DATABASE_NAME>
hmdb

> <SMILES>
NC(N)=NCC1COC2(CCCCC2)O1

> <INCHI_IDENTIFIER>
InChI=1S/C10H19N3O2/c11-9(12)13-6-8-7-14-10(15-8)4-2-1-3-5-10/h8H,1-7H2,(H4,11,12,13)

> <INCHI_KEY>
HPBNRIOWIXYZFK-UHFFFAOYSA-N

> <FORMULA>
C10H19N3O2

> <MOLECULAR_WEIGHT>
213.2768

> <EXACT_MASS>
213.147726867

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
23.2297074164034

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-{1,4-dioxaspiro[4.5]decan-2-ylmethyl}guanidine

> <ALOGPS_LOGP>
0.03

> <JCHEM_LOGP>
0.6234137306666664

> <ALOGPS_LOGS>
-2.04

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.852489384944136

> <JCHEM_PKA_STRONGEST_BASIC>
12.555155657498025

> <JCHEM_POLAR_SURFACE_AREA>
82.86

> <JCHEM_REFRACTIVITY>
56.5388

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.93e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
guanadrel

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014371
     RDKit          3D
Guanadrel
 34 35  0  0  0  0  0  0  0  0999 V2000
    5.1081    0.9752   -0.0603 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0202    0.0672   -0.1250 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8750   -0.9546    0.8454 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1718    0.1932   -1.0822 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0276   -0.6846   -1.2343 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0187   -0.3134   -0.1503 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5736    1.1024   -0.3590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7516    0.9479   -0.7472 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2094   -0.2366   -0.1935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2846   -0.8632   -1.0427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6124   -0.1840   -0.9113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6040    0.8684    0.1871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0744    0.1866    1.4318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6103   -0.0654    1.2404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1146   -1.1098   -0.2233 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9350    0.8518   -0.6894 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1323    1.7842    0.5987 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8579   -0.7324    1.8810 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7777   -1.9698    0.6080 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3108   -1.7512   -1.1676 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6081   -0.5232   -2.2460 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5474   -0.4588    0.8195 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6432    1.6972    0.5973 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1479    1.6200   -1.1566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3512   -1.9508   -0.8563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9558   -0.7556   -2.1034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9559    0.2992   -1.8478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4000   -0.9117   -0.6328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6347    1.2329    0.3316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8880    1.6597   -0.0750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6534   -0.7483    1.6619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2891    0.8787    2.2863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3226   -0.9494    1.8408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0436    0.7980    1.6506 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
  9 15  1  0
 15  6  1  0
 14  9  1  0
  1 16  1  0
  1 17  1  0
  3 18  1  0
  3 19  1  0
  5 20  1  0
  5 21  1  0
  6 22  1  0
  7 23  1  0
  7 24  1  0
 10 25  1  0
 10 26  1  0
 11 27  1  0
 11 28  1  0
 12 29  1  0
 12 30  1  0
 13 31  1  0
 13 32  1  0
 14 33  1  0
 14 34  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 38521                                             
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       7.065  -0.111   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       7.065  -2.603   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0      11.183  -0.308   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0      13.836  -0.029   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0      12.268   2.129   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       6.160  -1.357   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.390  -2.690   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.390  -0.023   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.850  -0.023   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.850  -2.690   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.080  -1.357   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.530  -0.587   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.530  -2.127   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.776   0.319   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.429   0.598   0.000  0.00  0.00           C+0
CONECT    1    6   12                                                       
CONECT    2    6   13                                                       
CONECT    3   14   15                                                       
CONECT    4   15                                                            
CONECT    5   15                                                            
CONECT    6    1    2    7    8                                             
CONECT    7    6   10                                                       
CONECT    8    6    9                                                       
CONECT    9    8   11                                                       
CONECT   10    7   11                                                       
CONECT   11    9   10                                                       
CONECT   12    1   13   14                                                  
CONECT   13    2   12                                                       
CONECT   14    3   12                                                       
CONECT   15    3    4    5                                                  
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

COMPND    HMDB0014371
HETATM    1  N1  UNL     1       5.108   0.975  -0.060  1.00  0.00           N  
HETATM    2  C1  UNL     1       4.020   0.067  -0.125  1.00  0.00           C  
HETATM    3  N2  UNL     1       3.875  -0.955   0.845  1.00  0.00           N  
HETATM    4  N3  UNL     1       3.172   0.193  -1.082  1.00  0.00           N  
HETATM    5  C2  UNL     1       2.028  -0.685  -1.234  1.00  0.00           C  
HETATM    6  C3  UNL     1       1.019  -0.313  -0.150  1.00  0.00           C  
HETATM    7  C4  UNL     1       0.574   1.102  -0.359  1.00  0.00           C  
HETATM    8  O1  UNL     1      -0.752   0.948  -0.747  1.00  0.00           O  
HETATM    9  C5  UNL     1      -1.209  -0.237  -0.193  1.00  0.00           C  
HETATM   10  C6  UNL     1      -2.285  -0.863  -1.043  1.00  0.00           C  
HETATM   11  C7  UNL     1      -3.612  -0.184  -0.911  1.00  0.00           C  
HETATM   12  C8  UNL     1      -3.604   0.868   0.187  1.00  0.00           C  
HETATM   13  C9  UNL     1      -3.074   0.187   1.432  1.00  0.00           C  
HETATM   14  C10 UNL     1      -1.610  -0.065   1.240  1.00  0.00           C  
HETATM   15  O2  UNL     1      -0.115  -1.110  -0.223  1.00  0.00           O  
HETATM   16  H1  UNL     1       5.935   0.852  -0.689  1.00  0.00           H  
HETATM   17  H2  UNL     1       5.132   1.784   0.599  1.00  0.00           H  
HETATM   18  H3  UNL     1       3.858  -0.732   1.881  1.00  0.00           H  
HETATM   19  H4  UNL     1       3.778  -1.970   0.608  1.00  0.00           H  
HETATM   20  H5  UNL     1       2.311  -1.751  -1.168  1.00  0.00           H  
HETATM   21  H6  UNL     1       1.608  -0.523  -2.246  1.00  0.00           H  
HETATM   22  H7  UNL     1       1.547  -0.459   0.820  1.00  0.00           H  
HETATM   23  H8  UNL     1       0.643   1.697   0.597  1.00  0.00           H  
HETATM   24  H9  UNL     1       1.148   1.620  -1.157  1.00  0.00           H  
HETATM   25  H10 UNL     1      -2.351  -1.951  -0.856  1.00  0.00           H  
HETATM   26  H11 UNL     1      -1.956  -0.756  -2.103  1.00  0.00           H  
HETATM   27  H12 UNL     1      -3.956   0.299  -1.848  1.00  0.00           H  
HETATM   28  H13 UNL     1      -4.400  -0.912  -0.633  1.00  0.00           H  
HETATM   29  H14 UNL     1      -4.635   1.233   0.332  1.00  0.00           H  
HETATM   30  H15 UNL     1      -2.888   1.660  -0.075  1.00  0.00           H  
HETATM   31  H16 UNL     1      -3.653  -0.748   1.662  1.00  0.00           H  
HETATM   32  H17 UNL     1      -3.289   0.879   2.286  1.00  0.00           H  
HETATM   33  H18 UNL     1      -1.323  -0.949   1.841  1.00  0.00           H  
HETATM   34  H19 UNL     1      -1.044   0.798   1.651  1.00  0.00           H  
CONECT    1    2   16   17
CONECT    2    3    4    4
CONECT    3   18   19
CONECT    4    5
CONECT    5    6   20   21
CONECT    6    7   15   22
CONECT    7    8   23   24
CONECT    8    9
CONECT    9   10   14   15
CONECT   10   11   25   26
CONECT   11   12   27   28
CONECT   12   13   29   30
CONECT   13   14   31   32
CONECT   14   33   34
END

HMDB0014371
     RDKit          3D
Guanadrel
 34 35  0  0  0  0  0  0  0  0999 V2000
    5.1081    0.9752   -0.0603 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0202    0.0672   -0.1250 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8750   -0.9546    0.8454 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1718    0.1932   -1.0822 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0276   -0.6846   -1.2343 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0187   -0.3134   -0.1503 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5736    1.1024   -0.3590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7516    0.9479   -0.7472 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2094   -0.2366   -0.1935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2846   -0.8632   -1.0427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6124   -0.1840   -0.9113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6040    0.8684    0.1871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0744    0.1866    1.4318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6103   -0.0654    1.2404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1146   -1.1098   -0.2233 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9350    0.8518   -0.6894 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1323    1.7842    0.5987 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8579   -0.7324    1.8810 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7777   -1.9698    0.6080 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3108   -1.7512   -1.1676 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6081   -0.5232   -2.2460 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5474   -0.4588    0.8195 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6432    1.6972    0.5973 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1479    1.6200   -1.1566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3512   -1.9508   -0.8563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9558   -0.7556   -2.1034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9559    0.2992   -1.8478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4000   -0.9117   -0.6328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6347    1.2329    0.3316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8880    1.6597   -0.0750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6534   -0.7483    1.6619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2891    0.8787    2.2863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3226   -0.9494    1.8408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0436    0.7980    1.6506 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
  9 15  1  0
 15  6  1  0
 14  9  1  0
  1 16  1  0
  1 17  1  0
  3 18  1  0
  3 19  1  0
  5 20  1  0
  5 21  1  0
  6 22  1  0
  7 23  1  0
  7 24  1  0
 10 25  1  0
 10 26  1  0
 11 27  1  0
 11 28  1  0
 12 29  1  0
 12 30  1  0
 13 31  1  0
 13 32  1  0
 14 33  1  0
 14 34  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Guanadrelum	ChEBI
Hylorel	Kegg
Guanadrel sulfuric acid	HMDB
Guanadrel sulphate	HMDB
Guanadrel sulphuric acid	HMDB
N-(1,4-Dioxaspiro[4.5]dec-2-ylmethyl)guanidine	HMDB
Guanadrel monosulfate	HMDB
Guanadrel monosulphate	HMDB
Guanadrel sulfate	HMDB
Guanadrel	HMDB

Chemical Formula

C₁₀H₁₉N₃O₂

Average Molecular Weight

213.2768

Monoisotopic Molecular Weight

213.147726867

IUPAC Name

2-{1,4-dioxaspiro[4.5]decan-2-ylmethyl}guanidine

Traditional Name

guanadrel

CAS Registry Number

40580-59-4

SMILES

NC(N)=NCC1COC2(CCCCC2)O1

InChI Identifier

InChI=1S/C10H19N3O2/c11-9(12)13-6-8-7-14-10(15-8)4-2-1-3-5-10/h8H,1-7H2,(H4,11,12,13)

InChI Key

HPBNRIOWIXYZFK-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as ketals. These are acetals derived from ketones by replacement of the oxo group by two hydrocarbyloxy groups R2C(OR)2 ( R not Hydrogen ). This term, once abandoned, has been reinstated as a subclass of acetals.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Ethers

Direct Parent

Ketals

Alternative Parents

Substituents

Ketal
Meta-dioxolane
Guanidine
Oxacycle
Organoheterocyclic compound
Carboximidamide
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Imine
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

guanidines (CHEBI:5555 )
spiroketal (CHEBI:5555 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0014371)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	1.93 g/L	Not Available
LogP	0.6	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.93 g/L	ALOGPS
logP	0.03	ALOGPS
logP	0.62	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	19.85	ChemAxon
pKa (Strongest Basic)	12.56	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	82.86 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	56.54 m³·mol⁻¹	ChemAxon
Polarizability	23.23 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
DarkChem	[M+H]+	149.773	31661259
DarkChem	[M-H]-	144.762	31661259
DeepCCS	[M+H]+	150.453	30932474
DeepCCS	[M-H]-	148.095	30932474
DeepCCS	[M-2H]-	183.184	30932474
DeepCCS	[M+Na]+	157.837	30932474
AllCCS	[M+H]+	149.5	32859911
AllCCS	[M+H-H2O]+	145.7	32859911
AllCCS	[M+NH4]+	153.0	32859911
AllCCS	[M+Na]+	154.0	32859911
AllCCS	[M-H]-	151.5	32859911
AllCCS	[M+Na-2H]-	151.9	32859911
AllCCS	[M+HCOO]-	152.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Guanadrel	NC(N)=NCC1COC2(CCCCC2)O1	2374.3	Standard polar	33892256
Guanadrel	NC(N)=NCC1COC2(CCCCC2)O1	1675.7	Standard non polar	33892256
Guanadrel	NC(N)=NCC1COC2(CCCCC2)O1	1986.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Guanadrel,1TMS,isomer #1	C[Si](C)(C)NC(N)=NCC1COC2(CCCCC2)O1	2007.3	Semi standard non polar	33892256
Guanadrel,1TMS,isomer #1	C[Si](C)(C)NC(N)=NCC1COC2(CCCCC2)O1	1792.2	Standard non polar	33892256
Guanadrel,1TMS,isomer #1	C[Si](C)(C)NC(N)=NCC1COC2(CCCCC2)O1	3035.7	Standard polar	33892256
Guanadrel,2TMS,isomer #1	C[Si](C)(C)NC(=NCC1COC2(CCCCC2)O1)N[Si](C)(C)C	2162.5	Semi standard non polar	33892256
Guanadrel,2TMS,isomer #1	C[Si](C)(C)NC(=NCC1COC2(CCCCC2)O1)N[Si](C)(C)C	1842.2	Standard non polar	33892256
Guanadrel,2TMS,isomer #1	C[Si](C)(C)NC(=NCC1COC2(CCCCC2)O1)N[Si](C)(C)C	3058.8	Standard polar	33892256
Guanadrel,2TMS,isomer #2	C[Si](C)(C)N(C(N)=NCC1COC2(CCCCC2)O1)[Si](C)(C)C	2115.8	Semi standard non polar	33892256
Guanadrel,2TMS,isomer #2	C[Si](C)(C)N(C(N)=NCC1COC2(CCCCC2)O1)[Si](C)(C)C	1997.0	Standard non polar	33892256
Guanadrel,2TMS,isomer #2	C[Si](C)(C)N(C(N)=NCC1COC2(CCCCC2)O1)[Si](C)(C)C	3156.9	Standard polar	33892256
Guanadrel,3TMS,isomer #1	C[Si](C)(C)NC(=NCC1COC2(CCCCC2)O1)N([Si](C)(C)C)[Si](C)(C)C	2187.2	Semi standard non polar	33892256
Guanadrel,3TMS,isomer #1	C[Si](C)(C)NC(=NCC1COC2(CCCCC2)O1)N([Si](C)(C)C)[Si](C)(C)C	2056.1	Standard non polar	33892256
Guanadrel,3TMS,isomer #1	C[Si](C)(C)NC(=NCC1COC2(CCCCC2)O1)N([Si](C)(C)C)[Si](C)(C)C	2941.9	Standard polar	33892256
Guanadrel,4TMS,isomer #1	C[Si](C)(C)N(C(=NCC1COC2(CCCCC2)O1)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2234.8	Semi standard non polar	33892256
Guanadrel,4TMS,isomer #1	C[Si](C)(C)N(C(=NCC1COC2(CCCCC2)O1)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2283.6	Standard non polar	33892256
Guanadrel,4TMS,isomer #1	C[Si](C)(C)N(C(=NCC1COC2(CCCCC2)O1)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2731.2	Standard polar	33892256
Guanadrel,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(N)=NCC1COC2(CCCCC2)O1	2235.4	Semi standard non polar	33892256
Guanadrel,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(N)=NCC1COC2(CCCCC2)O1	2042.6	Standard non polar	33892256
Guanadrel,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(N)=NCC1COC2(CCCCC2)O1	3280.1	Standard polar	33892256
Guanadrel,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=NCC1COC2(CCCCC2)O1)N[Si](C)(C)C(C)(C)C	2571.1	Semi standard non polar	33892256
Guanadrel,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=NCC1COC2(CCCCC2)O1)N[Si](C)(C)C(C)(C)C	2294.2	Standard non polar	33892256
Guanadrel,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=NCC1COC2(CCCCC2)O1)N[Si](C)(C)C(C)(C)C	3251.5	Standard polar	33892256
Guanadrel,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C(N)=NCC1COC2(CCCCC2)O1)[Si](C)(C)C(C)(C)C	2516.9	Semi standard non polar	33892256
Guanadrel,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C(N)=NCC1COC2(CCCCC2)O1)[Si](C)(C)C(C)(C)C	2436.6	Standard non polar	33892256
Guanadrel,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C(N)=NCC1COC2(CCCCC2)O1)[Si](C)(C)C(C)(C)C	3416.7	Standard polar	33892256
Guanadrel,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=NCC1COC2(CCCCC2)O1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2794.0	Semi standard non polar	33892256
Guanadrel,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=NCC1COC2(CCCCC2)O1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2704.2	Standard non polar	33892256
Guanadrel,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=NCC1COC2(CCCCC2)O1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3126.5	Standard polar	33892256
Guanadrel,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=NCC1COC2(CCCCC2)O1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3074.0	Semi standard non polar	33892256
Guanadrel,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=NCC1COC2(CCCCC2)O1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3053.4	Standard non polar	33892256
Guanadrel,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=NCC1COC2(CCCCC2)O1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2977.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Guanadrel GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9400000000-3e328dd7598b02063d5a	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Guanadrel GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Guanadrel GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Guanadrel 10V, Positive-QTOF	splash10-03di-4490000000-a78d2d502660f357a491	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Guanadrel 20V, Positive-QTOF	splash10-0229-9310000000-0778ebe61728471eea0d	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Guanadrel 40V, Positive-QTOF	splash10-03dl-9000000000-a1a36d3de5660c0018f7	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Guanadrel 10V, Negative-QTOF	splash10-0229-9760000000-08de942fb4b119d03f15	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Guanadrel 20V, Negative-QTOF	splash10-052f-9100000000-11ed2297e33929803cf0	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Guanadrel 40V, Negative-QTOF	splash10-052f-9000000000-7f78b604a8c1fcc8116a	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Guanadrel 10V, Positive-QTOF	splash10-03di-0290000000-dbf1037b6bac01f25ea6	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Guanadrel 20V, Positive-QTOF	splash10-08gj-9720000000-546065e239736f71a088	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Guanadrel 40V, Positive-QTOF	splash10-0536-9200000000-02d4464b6a16c151c7ed	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Guanadrel 10V, Negative-QTOF	splash10-044i-1960000000-1210a29f67ee4cc69b4a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Guanadrel 20V, Negative-QTOF	splash10-014j-8900000000-69e4c1bbae3fa476a53c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Guanadrel 40V, Negative-QTOF	splash10-0006-9400000000-18678395b551c1f8c3d4	2021-09-23	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 DB00226	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00226	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00226

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

35305

KEGG Compound ID

C07035

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Guanadrel

METLIN ID

Not Available

PubChem Compound

38521

PDB ID

Not Available

ChEBI ID

5555

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

Finnerty FA Jr, Brogden RN: Guanadrel. A review of its pharmacodynamic and pharmacokinetic properties and therapeutic use in hypertension. Drugs. 1985 Jul;30(1):22-31. [PubMed:3896742 ]
Cressman MD, Vidt DG: Newer agents in the treatment of arterial hypertension. Cleve Clin Q. 1984 Spring;51(1):179-84. [PubMed:6143629 ]

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

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Malinow SH: Comparison of guanadrel and guanethidine efficacy and side effects. Clin Ther. 1983;5(3):284-9. [PubMed:6850722 ]
Finnerty FA Jr, Brogden RN: Guanadrel. A review of its pharmacodynamic and pharmacokinetic properties and therapeutic use in hypertension. Drugs. 1985 Jul;30(1):22-31. [PubMed:3896742 ]
Palmer JD, Nugent CA: Guanadrel sulfate: a postganglionic sympathetic inhibitor for the treatment of mild to moderate hypertension. Pharmacotherapy. 1983 Jul-Aug;3(4):220-9. [PubMed:6351026 ]

Showing metabocard for Guanadrel (HMDB0014371)

MOL for HMDB0014371 (Guanadrel)

3D MOL for HMDB0014371 (Guanadrel)

3D SDF for HMDB0014371 (Guanadrel)

3D-SDF for HMDB0014371 (Guanadrel)

PDB for HMDB0014371 (Guanadrel)

3D PDB for HMDB0014371 (Guanadrel)

SMILES for HMDB0014371 (Guanadrel)

INCHI for HMDB0014371 (Guanadrel)

Structure for HMDB0014371 (Guanadrel)

3D Structure for HMDB0014371 (Guanadrel)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Transporters

References