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Showing metabocard for Bretylium (HMDB0015289)

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enzymes (1) Show 1 protein
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2022-03-07 02:51:55 UTC
HMDB IDHMDB0015289
Secondary Accession Numbers
  • HMDB15289
Metabolite Identification
Common NameBretylium
DescriptionBretylium blocks the release of noradrenaline from the peripheral sympathetic nervous system, and is used in emergency medicine, cardiology, and other specialties for the acute management of ventricular tachycardia and ventricular fibrillation. The primary mode of action for bretylium is thought to be inhibition of voltage-gated K(+) channels. Recent evidence has shown that bretylium may also inhibit the Na,K-ATPase by binding to the extracellular K-site.
Structure
Data?1582753280
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0015289 (Bretylium)

1158
  Mrv0541 02231215172D          

 13 13  0  0  0  0            999 V2000
    1.6500   -0.4125    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.8250    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    3.0791    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3810    1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2060    0.1106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  9  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  2  5  1  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
  4  8  1  0  0  0  0
  7  9  1  0  0  0  0
  7 10  2  0  0  0  0
  9 11  2  0  0  0  0
 10 12  1  0  0  0  0
 11 13  1  0  0  0  0
 12 13  2  0  0  0  0
M  CHG  1   2   1
M  END
Download

3D MOL for HMDB0015289 (Bretylium)

HMDB0015289
     RDKit          3D
Bretylium
 30 30  0  0  0  0  0  0  0  0999 V2000
   -3.3610    0.1218    0.2929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1720   -0.7936    0.0879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9744   -0.0870   -0.2220 N   0  0  0  0  0  4  0  0  0  0  0  0
   -0.2605   -0.7946   -1.2621 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3601    1.1802   -0.9350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1525    0.3298    0.8987 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2813    0.1013    0.4721 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7417   -1.1744    0.3063 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0184   -1.3412   -0.2383 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7446   -0.1936   -0.5791 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2454    1.0725   -0.3885 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9605    1.2211    0.1612 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2875    2.9773    0.5530 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -3.2563    0.6801    1.2335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5746    0.7576   -0.5842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2299   -0.5483    0.4254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4834   -1.4377   -0.8036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1057   -1.4699    0.9289 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6562   -0.2980   -1.6137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9819   -0.7392   -2.1526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1683   -1.8734   -1.0626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8603    1.8475   -0.2362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9724    0.8524   -1.7903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4189    1.5404   -1.3810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3767    1.3022    1.2700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3177   -0.4595    1.6899 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1806   -2.0620    0.6602 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4310   -2.3222   -0.3715 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7195   -0.3591   -1.0463 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7599    1.9699   -0.6935 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  3  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12  7  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  2 17  1  0
  2 18  1  0
  4 19  1  0
  4 20  1  0
  4 21  1  0
  5 22  1  0
  5 23  1  0
  5 24  1  0
  6 25  1  0
  6 26  1  0
  8 27  1  0
  9 28  1  0
 10 29  1  0
 11 30  1  0
M  CHG  1   3   1
M  END
Download

3D SDF for HMDB0015289 (Bretylium)

1158
  Mrv0541 02231215172D          

 13 13  0  0  0  0            999 V2000
    1.6500   -0.4125    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.8250    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    3.0791    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3810    1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2060    0.1106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  9  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  2  5  1  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
  4  8  1  0  0  0  0
  7  9  1  0  0  0  0
  7 10  2  0  0  0  0
  9 11  2  0  0  0  0
 10 12  1  0  0  0  0
 11 13  1  0  0  0  0
 12 13  2  0  0  0  0
M  CHG  1   2   1
M  END
> <DATABASE_ID>
HMDB0015289

> <DATABASE_NAME>
hmdb

> <SMILES>
CC[N+](C)(C)CC1=CC=CC=C1Br

> <INCHI_IDENTIFIER>
InChI=1S/C11H17BrN/c1-4-13(2,3)9-10-7-5-6-8-11(10)12/h5-8H,4,9H2,1-3H3/q+1

> <INCHI_KEY>
AAQOQKQBGPPFNS-UHFFFAOYSA-N

> <FORMULA>
C11H17BrN

> <MOLECULAR_WEIGHT>
243.163

> <EXACT_MASS>
242.054437196

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_AVERAGE_POLARIZABILITY>
23.240558368171648

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2-bromophenyl)methyl](ethyl)dimethylazanium

> <ALOGPS_LOGP>
-1.36

> <JCHEM_LOGP>
-1.122133453471745

> <ALOGPS_LOGS>
-6.26

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.58236914184091

> <JCHEM_POLAR_SURFACE_AREA>
0

> <JCHEM_REFRACTIVITY>
72.88570000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.54e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
bretylium

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for HMDB0015289 (Bretylium)

HMDB0015289
     RDKit          3D
Bretylium
 30 30  0  0  0  0  0  0  0  0999 V2000
   -3.3610    0.1218    0.2929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1720   -0.7936    0.0879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9744   -0.0870   -0.2220 N   0  0  0  0  0  4  0  0  0  0  0  0
   -0.2605   -0.7946   -1.2621 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3601    1.1802   -0.9350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1525    0.3298    0.8987 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2813    0.1013    0.4721 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7417   -1.1744    0.3063 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0184   -1.3412   -0.2383 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7446   -0.1936   -0.5791 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2454    1.0725   -0.3885 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9605    1.2211    0.1612 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2875    2.9773    0.5530 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -3.2563    0.6801    1.2335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5746    0.7576   -0.5842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2299   -0.5483    0.4254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4834   -1.4377   -0.8036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1057   -1.4699    0.9289 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6562   -0.2980   -1.6137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9819   -0.7392   -2.1526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1683   -1.8734   -1.0626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8603    1.8475   -0.2362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9724    0.8524   -1.7903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4189    1.5404   -1.3810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3767    1.3022    1.2700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3177   -0.4595    1.6899 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1806   -2.0620    0.6602 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4310   -2.3222   -0.3715 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7195   -0.3591   -1.0463 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7599    1.9699   -0.6935 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  3  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12  7  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  2 17  1  0
  2 18  1  0
  4 19  1  0
  4 20  1  0
  4 21  1  0
  5 22  1  0
  5 23  1  0
  5 24  1  0
  6 25  1  0
  6 26  1  0
  8 27  1  0
  9 28  1  0
 10 29  1  0
 11 30  1  0
M  CHG  1   3   1
M  END
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PDB for HMDB0015289 (Bretylium)

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1158                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Br   UNK     0       3.080  -0.770   0.000  0.00  0.00          Br+0
HETATM    2  N   UNK     0       7.081   1.540   0.000  0.00  0.00           N+1
HETATM    3  C   UNK     0       5.748   0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.415   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.311   2.874   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.851   0.206   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.748  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.415   3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.414  -1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.081  -1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.414  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.081  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.748  -3.850   0.000  0.00  0.00           C+0
CONECT    1    9                                                            
CONECT    2    3    4    5    6                                             
CONECT    3    2    7                                                       
CONECT    4    2    8                                                       
CONECT    5    2                                                            
CONECT    6    2                                                            
CONECT    7    3    9   10                                                  
CONECT    8    4                                                            
CONECT    9    1    7   11                                                  
CONECT   10    7   12                                                       
CONECT   11    9   13                                                       
CONECT   12   10   13                                                       
CONECT   13   11   12                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END
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3D PDB for HMDB0015289 (Bretylium)

COMPND    HMDB0015289
HETATM    1  C1  UNL     1      -3.361   0.122   0.293  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.172  -0.794   0.088  1.00  0.00           C  
HETATM    3  N1  UNL     1      -0.974  -0.087  -0.222  1.00  0.00           N1+
HETATM    4  C3  UNL     1      -0.260  -0.795  -1.262  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.360   1.180  -0.935  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.153   0.330   0.899  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.281   0.101   0.472  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.742  -1.174   0.306  1.00  0.00           C  
HETATM    9  C8  UNL     1       3.018  -1.341  -0.238  1.00  0.00           C  
HETATM   10  C9  UNL     1       3.745  -0.194  -0.579  1.00  0.00           C  
HETATM   11  C10 UNL     1       3.245   1.072  -0.389  1.00  0.00           C  
HETATM   12  C11 UNL     1       1.961   1.221   0.161  1.00  0.00           C  
HETATM   13 BR1  UNL     1       1.287   2.977   0.553  1.00  0.00          BR  
HETATM   14  H1  UNL     1      -3.256   0.680   1.233  1.00  0.00           H  
HETATM   15  H2  UNL     1      -3.575   0.758  -0.584  1.00  0.00           H  
HETATM   16  H3  UNL     1      -4.230  -0.548   0.425  1.00  0.00           H  
HETATM   17  H4  UNL     1      -2.483  -1.438  -0.804  1.00  0.00           H  
HETATM   18  H5  UNL     1      -2.106  -1.470   0.929  1.00  0.00           H  
HETATM   19  H6  UNL     1       0.656  -0.298  -1.614  1.00  0.00           H  
HETATM   20  H7  UNL     1      -0.982  -0.739  -2.153  1.00  0.00           H  
HETATM   21  H8  UNL     1      -0.168  -1.873  -1.063  1.00  0.00           H  
HETATM   22  H9  UNL     1      -1.860   1.848  -0.236  1.00  0.00           H  
HETATM   23  H10 UNL     1      -1.972   0.852  -1.790  1.00  0.00           H  
HETATM   24  H11 UNL     1      -0.419   1.540  -1.381  1.00  0.00           H  
HETATM   25  H12 UNL     1      -0.377   1.302   1.270  1.00  0.00           H  
HETATM   26  H13 UNL     1      -0.318  -0.460   1.690  1.00  0.00           H  
HETATM   27  H14 UNL     1       1.181  -2.062   0.660  1.00  0.00           H  
HETATM   28  H15 UNL     1       3.431  -2.322  -0.371  1.00  0.00           H  
HETATM   29  H16 UNL     1       4.720  -0.359  -1.046  1.00  0.00           H  
HETATM   30  H17 UNL     1       3.760   1.970  -0.694  1.00  0.00           H  
CONECT    1    2   14   15   16
CONECT    2    3   17   18
CONECT    3    4    5    6
CONECT    4   19   20   21
CONECT    5   22   23   24
CONECT    6    7   25   26
CONECT    7    8    8   12
CONECT    8    9   27
CONECT    9   10   10   28
CONECT   10   11   29
CONECT   11   12   12   30
CONECT   12   13
END
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SMILES for HMDB0015289 (Bretylium)

CC[N+](C)(C)CC1=CC=CC=C1Br
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INCHI for HMDB0015289 (Bretylium)

InChI=1S/C11H17BrN/c1-4-13(2,3)9-10-7-5-6-8-11(10)12/h5-8H,4,9H2,1-3H3/q+1
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Synonyms
ValueSource
(2-Bromobenzyl)ethyldimethylaminiumChEBI
2-Bromo-N-ethyl-N,N-dimethylbenzenemethanaminiumChEBI
N-Ethyl-N,N-dimethyl-2-bromobenzenemethanaminiumChEBI
BretylateHMDB
Bretylium tolsylateHMDB
Bretylium tosylateHMDB
BretylumHMDB
Bretylium bromideHMDB
Bretylium chlorideHMDB
Bretylium iodideHMDB
Chemical FormulaC11H17BrN
Average Molecular Weight243.163
Monoisotopic Molecular Weight242.054437196
IUPAC Name[(2-bromophenyl)methyl](ethyl)dimethylazanium
Traditional Namebretylium
CAS Registry Number59-41-6
SMILES
CC[N+](C)(C)CC1=CC=CC=C1Br
InChI Identifier
InChI=1S/C11H17BrN/c1-4-13(2,3)9-10-7-5-6-8-11(10)12/h5-8H,4,9H2,1-3H3/q+1
InChI KeyAAQOQKQBGPPFNS-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenylmethylamines. Phenylmethylamines are compounds containing a phenylmethtylamine moiety, which consists of a phenyl group substituted by an methanamine.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylmethylamines
Direct ParentPhenylmethylamines
Alternative Parents
Substituents
  • Benzylamine
  • Phenylmethylamine
  • Aralkylamine
  • Bromobenzene
  • Halobenzene
  • Aryl bromide
  • Aryl halide
  • Tetraalkylammonium salt
  • Quaternary ammonium salt
  • Amine
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organobromide
  • Organohalogen compound
  • Organic salt
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic cation
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological location
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.00015 g/LNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available140.573http://allccs.zhulab.cn/database/detail?ID=AllCCS00000839
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.00015 g/LALOGPS
logP-1.4ALOGPS
logP-1.1ChemAxon
logS-6.3ALOGPS
pKa (Strongest Acidic)17.58ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity72.89 m³·mol⁻¹ChemAxon
Polarizability23.24 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+133.19830932474
DeepCCS[M-H]-130.80330932474
DeepCCS[M-2H]-166.44430932474
DeepCCS[M+Na]+141.28230932474
AllCCS[M+H]+148.332859911
AllCCS[M+H-H2O]+144.632859911
AllCCS[M+NH4]+151.832859911
AllCCS[M+Na]+152.832859911
AllCCS[M-H]-159.232859911
AllCCS[M+Na-2H]-160.632859911
AllCCS[M+HCOO]-162.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
BretyliumCC[N+](C)(C)CC1=CC=CC=C1Br1993.1Standard polar33892256
BretyliumCC[N+](C)(C)CC1=CC=CC=C1Br1387.2Standard non polar33892256
BretyliumCC[N+](C)(C)CC1=CC=CC=C1Br1505.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Bretylium GC-MS (Non-derivatized) - 70eV, Positivesplash10-00or-9660000000-f1a790c5dc75745515bf2017-08-28Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Bretylium GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Bretylium GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bretylium 10V, Positive-QTOFsplash10-0006-0090000000-4aeb2988fef6edbee36e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bretylium 20V, Positive-QTOFsplash10-03xr-0390000000-a00c3f0ed8c3aa8c892a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bretylium 40V, Positive-QTOFsplash10-014i-2910000000-431fec477d416b1fea582017-09-01Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01158 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01158 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01158
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2337
KEGG Compound IDC06855
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkBretylium
METLIN IDNot Available
PubChem Compound2431
PDB IDNot Available
ChEBI ID3172
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Sodium/potassium-transporting ATPase subunit alpha-1
General function:
Involved in ATP binding
Specific function:
This is the catalytic component of the active enzyme, which catalyzes the hydrolysis of ATP coupled with the exchange of sodium and potassium ions across the plasma membrane. This action creates the electrochemical gradient of sodium and potassium ions, providing the energy for active transport of various nutrients.
Gene Name:
ATP1A1
Uniprot ID:
P05023
Molecular weight:
112895.01
References
  1. Dzimiri N, Almotrefi AA: Inhibition of myocardial Na(+)-K(+)-ATPase activity by bretylium: role of potassium. Arch Int Pharmacodyn Ther. 1992 Jul-Aug;318:76-85. [PubMed:1334399 ]
  2. Helms JB, Arnett KL, Gatto C, Milanick MA: Bretylium, an organic quaternary amine, inhibits the Na,K-ATPase by binding to the extracellular K-site. Blood Cells Mol Dis. 2004 May-Jun;32(3):394-400. [PubMed:15121098 ]
  3. Dzimiri N, Almotrefi AA: Interaction of bretylium tosylate with guinea-pig myocardial Na(+)-K(+)-ATPase. Gen Pharmacol. 1991;22(5):935-8. [PubMed:1662173 ]
  4. Tiku PE, Nowell PT: Selective inhibition of K(+)-stimulation of Na,K-ATPase by bretylium. Br J Pharmacol. 1991 Dec;104(4):895-900. [PubMed:1667290 ]