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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:52 UTC

Update Date

2022-03-07 02:52:05 UTC

HMDB ID

HMDB0015697

Secondary Accession Numbers

HMDB15697

Metabolite Identification

Common Name

Bupranolol

Description

Bupranolol, also known as KL-255 or b 1312, belongs to the class of organic compounds known as phenol ethers. These are aromatic compounds containing an ether group substituted with a benzene ring. The main metabolite is carboxybupranolol, 4-chloro-3-benzoic acid, of which 88% are eliminated renally within 24 hours. Bupranolol is a drug which is used to manage hypertension and tachycardia. also used to treat glaucoma. Bupranolol is a non-selective beta blocker with potency similar to . Bupranolol is a very strong basic compound (based on its pKa). Its potency is similar to 'propranolol':http://www.drugbank.ca/drugs/DB00571. Bupranolol is a competitive, nonselective beta-blocker similar to propanolol without intrinsic sympathomimetic activity. It is a non-selective beta blocker without intrinsic sympathomimetic activity (ISA), but with strong membrane stabilizing activity. In humans, bupranolol is involved in bupranolol action pathway. Over 90% undergoes first-pass metabolism. Bupranolol is only found in individuals that have used or taken this drug. It does not have intrinsic sympathomimetic activity (ISA), but does have strong membrane stabilizing activity.

Structure

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

HMDB0015697
     RDKit          3D
Bupranolol
 40 40  0  0  0  0  0  0  0  0999 V2000
    5.0325    1.9428   -0.2598 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6887    0.5338    0.0679 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6090   -0.3783    0.5295 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2519   -1.6860    0.8254 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9856   -2.1247    0.6748 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4867   -3.7819    1.0396 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.0102   -1.2137    0.2018 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7658   -1.6609    0.0562 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5210   -1.3235   -0.2994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2468   -0.3049    0.4669 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2569    0.9529    0.5482 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6669   -0.3043   -0.1257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5578    0.4826    0.7012 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8867    0.4750    0.1371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8444    1.2950    0.9571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4314   -0.9471    0.1113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7943    0.9573   -1.2869 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3759    0.0838   -0.0901 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0178    2.1393   -1.3445 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3333    2.5947    0.3044 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0731    2.1288    0.1068 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6295   -0.0325    0.6534 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0032   -2.3748    1.1860 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5686   -0.9067   -1.3683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1854   -2.1939   -0.4449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3910   -0.6612    1.5355 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1085    1.3770    1.4286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0668   -1.3220   -0.1783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6578    0.1147   -1.1514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2398    1.4689    0.8093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4560    1.3242    1.9941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8467    0.8051    1.0174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0029    2.2950    0.5259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5405   -0.9143    0.1067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0852   -1.4464    1.0395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1159   -1.4602   -0.8102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7869    1.3378   -1.6375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0464    1.7662   -1.4237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5340    0.1339   -1.9839 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6655    0.8282   -0.4751 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 14 17  1  0
  7 18  2  0
 18  2  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  4 23  1  0
  9 24  1  0
  9 25  1  0
 10 26  1  0
 11 27  1  0
 12 28  1  0
 12 29  1  0
 13 30  1  0
 15 31  1  0
 15 32  1  0
 15 33  1  0
 16 34  1  0
 16 35  1  0
 16 36  1  0
 17 37  1  0
 17 38  1  0
 17 39  1  0
 18 40  1  0
M  END

2475
  Mrv0541 02241214202D          

 18 18  0  0  1  0            999 V2000
    1.6500   -1.3885    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    1.0865    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -0.5635    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.9116    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    2.3241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.0865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.6740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    2.7366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8099    3.0385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6350    1.6096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.1510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -1.3885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -1.8010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.8010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -2.6260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -3.0385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.6260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -3.0385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 14  1  0  0  0  0
  2  7  1  0  0  0  0
  3 11  1  0  0  0  0
  3 12  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  5  8  1  0  0  0  0
  5  9  1  0  0  0  0
  5 10  1  0  0  0  0
  6  7  1  0  0  0  0
  7 11  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 13 15  2  0  0  0  0
 14 17  1  0  0  0  0
 15 16  1  0  0  0  0
 15 18  1  0  0  0  0
 16 17  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015697

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=CC(OCC(O)CNC(C)(C)C)=C(Cl)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C14H22ClNO2/c1-10-5-6-12(15)13(7-10)18-9-11(17)8-16-14(2,3)4/h5-7,11,16-17H,8-9H2,1-4H3

> <INCHI_KEY>
HQIRNZOQPUAHHV-UHFFFAOYSA-N

> <FORMULA>
C14H22ClNO2

> <MOLECULAR_WEIGHT>
271.783

> <EXACT_MASS>
271.13390666

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
30.34887880204026

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-(tert-butylamino)-3-(2-chloro-5-methylphenoxy)propan-2-ol

> <ALOGPS_LOGP>
3.14

> <JCHEM_LOGP>
2.992261906666667

> <ALOGPS_LOGS>
-3.28

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.087500711296151

> <JCHEM_PKA_STRONGEST_BASIC>
9.759522836750762

> <JCHEM_POLAR_SURFACE_AREA>
41.49

> <JCHEM_REFRACTIVITY>
74.85970000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.43e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-(tert-butylamino)-3-(2-chloro-5-methylphenoxy)propan-2-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015697
     RDKit          3D
Bupranolol
 40 40  0  0  0  0  0  0  0  0999 V2000
    5.0325    1.9428   -0.2598 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6887    0.5338    0.0679 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6090   -0.3783    0.5295 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2519   -1.6860    0.8254 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9856   -2.1247    0.6748 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4867   -3.7819    1.0396 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.0102   -1.2137    0.2018 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7658   -1.6609    0.0562 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5210   -1.3235   -0.2994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2468   -0.3049    0.4669 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2569    0.9529    0.5482 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6669   -0.3043   -0.1257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5578    0.4826    0.7012 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8867    0.4750    0.1371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8444    1.2950    0.9571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4314   -0.9471    0.1113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7943    0.9573   -1.2869 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3759    0.0838   -0.0901 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0178    2.1393   -1.3445 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3333    2.5947    0.3044 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0731    2.1288    0.1068 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6295   -0.0325    0.6534 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0032   -2.3748    1.1860 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5686   -0.9067   -1.3683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1854   -2.1939   -0.4449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3910   -0.6612    1.5355 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1085    1.3770    1.4286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0668   -1.3220   -0.1783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6578    0.1147   -1.1514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2398    1.4689    0.8093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4560    1.3242    1.9941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8467    0.8051    1.0174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0029    2.2950    0.5259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5405   -0.9143    0.1067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0852   -1.4464    1.0395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1159   -1.4602   -0.8102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7869    1.3378   -1.6375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0464    1.7662   -1.4237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5340    0.1339   -1.9839 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6655    0.8282   -0.4751 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 14 17  1  0
  7 18  2  0
 18  2  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  4 23  1  0
  9 24  1  0
  9 25  1  0
 10 26  1  0
 11 27  1  0
 12 28  1  0
 12 29  1  0
 13 30  1  0
 15 31  1  0
 15 32  1  0
 15 33  1  0
 16 34  1  0
 16 35  1  0
 16 36  1  0
 17 37  1  0
 17 38  1  0
 17 39  1  0
 18 40  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 2475                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1 Cl   UNK     0       3.080  -2.592   0.000  0.00  0.00          Cl+0
HETATM    2  O   UNK     0       5.747   2.028   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       5.747  -1.052   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       8.415   3.568   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       9.748   4.338   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.415   2.028   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.081   1.258   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.082   5.108   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.978   5.672   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.519   3.005   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.081  -0.282   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.747  -2.592   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.081  -3.362   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.414  -3.362   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.081  -4.902   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.747  -5.672   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.414  -4.902   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.415  -5.672   0.000  0.00  0.00           C+0
CONECT    1   14                                                            
CONECT    2    7                                                            
CONECT    3   11   12                                                       
CONECT    4    5    6                                                       
CONECT    5    4    8    9   10                                             
CONECT    6    4    7                                                       
CONECT    7    2    6   11                                                  
CONECT    8    5                                                            
CONECT    9    5                                                            
CONECT   10    5                                                            
CONECT   11    3    7                                                       
CONECT   12    3   13   14                                                  
CONECT   13   12   15                                                       
CONECT   14    1   12   17                                                  
CONECT   15   13   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   14   16                                                       
CONECT   18   15                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   36    0
END

COMPND    HMDB0015697
HETATM    1  C1  UNL     1       5.032   1.943  -0.260  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.689   0.534   0.068  1.00  0.00           C  
HETATM    3  C3  UNL     1       5.609  -0.378   0.529  1.00  0.00           C  
HETATM    4  C4  UNL     1       5.252  -1.686   0.825  1.00  0.00           C  
HETATM    5  C5  UNL     1       3.986  -2.125   0.675  1.00  0.00           C  
HETATM    6 CL1  UNL     1       3.487  -3.782   1.040  1.00  0.00          CL  
HETATM    7  C6  UNL     1       3.010  -1.214   0.202  1.00  0.00           C  
HETATM    8  O1  UNL     1       1.766  -1.661   0.056  1.00  0.00           O  
HETATM    9  C7  UNL     1       0.521  -1.324  -0.299  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.247  -0.305   0.467  1.00  0.00           C  
HETATM   11  O2  UNL     1       0.257   0.953   0.548  1.00  0.00           O  
HETATM   12  C9  UNL     1      -1.667  -0.304  -0.126  1.00  0.00           C  
HETATM   13  N1  UNL     1      -2.558   0.483   0.701  1.00  0.00           N  
HETATM   14  C10 UNL     1      -3.887   0.475   0.137  1.00  0.00           C  
HETATM   15  C11 UNL     1      -4.844   1.295   0.957  1.00  0.00           C  
HETATM   16  C12 UNL     1      -4.431  -0.947   0.111  1.00  0.00           C  
HETATM   17  C13 UNL     1      -3.794   0.957  -1.287  1.00  0.00           C  
HETATM   18  C14 UNL     1       3.376   0.084  -0.090  1.00  0.00           C  
HETATM   19  H1  UNL     1       5.018   2.139  -1.345  1.00  0.00           H  
HETATM   20  H2  UNL     1       4.333   2.595   0.304  1.00  0.00           H  
HETATM   21  H3  UNL     1       6.073   2.129   0.107  1.00  0.00           H  
HETATM   22  H4  UNL     1       6.629  -0.032   0.653  1.00  0.00           H  
HETATM   23  H5  UNL     1       6.003  -2.375   1.186  1.00  0.00           H  
HETATM   24  H6  UNL     1       0.569  -0.907  -1.368  1.00  0.00           H  
HETATM   25  H7  UNL     1      -0.185  -2.194  -0.445  1.00  0.00           H  
HETATM   26  H8  UNL     1      -0.391  -0.661   1.536  1.00  0.00           H  
HETATM   27  H9  UNL     1       0.109   1.377   1.429  1.00  0.00           H  
HETATM   28  H10 UNL     1      -2.067  -1.322  -0.178  1.00  0.00           H  
HETATM   29  H11 UNL     1      -1.658   0.115  -1.151  1.00  0.00           H  
HETATM   30  H12 UNL     1      -2.240   1.469   0.809  1.00  0.00           H  
HETATM   31  H13 UNL     1      -4.456   1.324   1.994  1.00  0.00           H  
HETATM   32  H14 UNL     1      -5.847   0.805   1.017  1.00  0.00           H  
HETATM   33  H15 UNL     1      -5.003   2.295   0.526  1.00  0.00           H  
HETATM   34  H16 UNL     1      -5.541  -0.914   0.107  1.00  0.00           H  
HETATM   35  H17 UNL     1      -4.085  -1.446   1.040  1.00  0.00           H  
HETATM   36  H18 UNL     1      -4.116  -1.460  -0.810  1.00  0.00           H  
HETATM   37  H19 UNL     1      -4.787   1.338  -1.637  1.00  0.00           H  
HETATM   38  H20 UNL     1      -3.046   1.766  -1.424  1.00  0.00           H  
HETATM   39  H21 UNL     1      -3.534   0.134  -1.984  1.00  0.00           H  
HETATM   40  H22 UNL     1       2.666   0.828  -0.475  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3    3   18
CONECT    3    4   22
CONECT    4    5    5   23
CONECT    5    6    7
CONECT    7    8   18   18
CONECT    8    9
CONECT    9   10   24   25
CONECT   10   11   12   26
CONECT   11   27
CONECT   12   13   28   29
CONECT   13   14   30
CONECT   14   15   16   17
CONECT   15   31   32   33
CONECT   16   34   35   36
CONECT   17   37   38   39
CONECT   18   40
END

HMDB0015697
     RDKit          3D
Bupranolol
 40 40  0  0  0  0  0  0  0  0999 V2000
    5.0325    1.9428   -0.2598 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6887    0.5338    0.0679 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6090   -0.3783    0.5295 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2519   -1.6860    0.8254 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9856   -2.1247    0.6748 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4867   -3.7819    1.0396 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.0102   -1.2137    0.2018 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7658   -1.6609    0.0562 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5210   -1.3235   -0.2994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2468   -0.3049    0.4669 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2569    0.9529    0.5482 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6669   -0.3043   -0.1257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5578    0.4826    0.7012 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8867    0.4750    0.1371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8444    1.2950    0.9571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4314   -0.9471    0.1113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7943    0.9573   -1.2869 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3759    0.0838   -0.0901 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0178    2.1393   -1.3445 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3333    2.5947    0.3044 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0731    2.1288    0.1068 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6295   -0.0325    0.6534 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0032   -2.3748    1.1860 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5686   -0.9067   -1.3683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1854   -2.1939   -0.4449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3910   -0.6612    1.5355 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1085    1.3770    1.4286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0668   -1.3220   -0.1783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6578    0.1147   -1.1514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2398    1.4689    0.8093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4560    1.3242    1.9941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8467    0.8051    1.0174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0029    2.2950    0.5259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5405   -0.9143    0.1067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0852   -1.4464    1.0395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1159   -1.4602   -0.8102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7869    1.3378   -1.6375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0464    1.7662   -1.4237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5340    0.1339   -1.9839 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6655    0.8282   -0.4751 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 14 17  1  0
  7 18  2  0
 18  2  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  4 23  1  0
  9 24  1  0
  9 25  1  0
 10 26  1  0
 11 27  1  0
 12 28  1  0
 12 29  1  0
 13 30  1  0
 15 31  1  0
 15 32  1  0
 15 33  1  0
 16 34  1  0
 16 35  1  0
 16 36  1  0
 17 37  1  0
 17 38  1  0
 17 39  1  0
 18 40  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
BUPRANOLOL hydrochloride	HMDB
KL-255	HMDB
BUPRANOL	HMDB
b 1312	HMDB
Bupranololum	HMDB
Desma brand OF bupranolol hydrochloride	HMDB
Betadrenol	HMDB

Chemical Formula

C₁₄H₂₂ClNO₂

Average Molecular Weight

271.783

Monoisotopic Molecular Weight

271.13390666

IUPAC Name

1-(tert-butylamino)-3-(2-chloro-5-methylphenoxy)propan-2-ol

Traditional Name

1-(tert-butylamino)-3-(2-chloro-5-methylphenoxy)propan-2-ol

CAS Registry Number

23284-25-5

SMILES

CC1=CC(OCC(O)CNC(C)(C)C)=C(Cl)C=C1

InChI Identifier

InChI=1S/C14H22ClNO2/c1-10-5-6-12(15)13(7-10)18-9-11(17)8-16-14(2,3)4/h5-7,11,16-17H,8-9H2,1-4H3

InChI Key

HQIRNZOQPUAHHV-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenol ethers. These are aromatic compounds containing an ether group substituted with a benzene ring.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenol ethers

Sub Class

Not Available

Direct Parent

Phenol ethers

Alternative Parents

Substituents

Phenoxy compound
Phenol ether
Alkyl aryl ether
Toluene
Chlorobenzene
Halobenzene
Aryl chloride
Aryl halide
Monocyclic benzene moiety
1,2-aminoalcohol
Secondary alcohol
Secondary amine
Secondary aliphatic amine
Ether
Organic oxygen compound
Alcohol
Organooxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Amine
Organonitrogen compound
Organohalogen compound
Organochloride
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0015697)

Source

Exogenous

Exogenous (HMDB: HMDB0015697)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Bupranolol Action Pathway (PathBank: SMP0000670)

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	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.14 g/L	ALOGPS
logP	3.14	ALOGPS
logP	2.99	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	14.09	ChemAxon
pKa (Strongest Basic)	9.76	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	41.49 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	74.86 m³·mol⁻¹	ChemAxon
Polarizability	30.35 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	165.604	30932474
DeepCCS	[M-H]-	163.246	30932474
DeepCCS	[M-2H]-	196.133	30932474
DeepCCS	[M+Na]+	171.698	30932474
AllCCS	[M+H]+	161.4	32859911
AllCCS	[M+H-H2O]+	158.2	32859911
AllCCS	[M+NH4]+	164.5	32859911
AllCCS	[M+Na]+	165.3	32859911
AllCCS	[M-H]-	166.3	32859911
AllCCS	[M+Na-2H]-	166.8	32859911
AllCCS	[M+HCOO]-	167.6	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	4.74 minutes	32390414
Predicted by Siyang on May 30, 2022	11.7444 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.7 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	54.3 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1525.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	265.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	152.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	171.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	93.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	393.3 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	398.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	76.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	821.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	413.9 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1237.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	268.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	304.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	261.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	132.9 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Bupranolol	CC1=CC(OCC(O)CNC(C)(C)C)=C(Cl)C=C1	2739.5	Standard polar	33892256
Bupranolol	CC1=CC(OCC(O)CNC(C)(C)C)=C(Cl)C=C1	1907.8	Standard non polar	33892256
Bupranolol	CC1=CC(OCC(O)CNC(C)(C)C)=C(Cl)C=C1	1950.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Bupranolol,1TMS,isomer #1	CC1=CC=C(Cl)C(OCC(CNC(C)(C)C)O[Si](C)(C)C)=C1	1909.6	Semi standard non polar	33892256
Bupranolol,1TMS,isomer #2	CC1=CC=C(Cl)C(OCC(O)CN(C(C)(C)C)[Si](C)(C)C)=C1	2121.1	Semi standard non polar	33892256
Bupranolol,2TMS,isomer #1	CC1=CC=C(Cl)C(OCC(CN(C(C)(C)C)[Si](C)(C)C)O[Si](C)(C)C)=C1	2149.5	Semi standard non polar	33892256
Bupranolol,2TMS,isomer #1	CC1=CC=C(Cl)C(OCC(CN(C(C)(C)C)[Si](C)(C)C)O[Si](C)(C)C)=C1	2181.8	Standard non polar	33892256
Bupranolol,2TMS,isomer #1	CC1=CC=C(Cl)C(OCC(CN(C(C)(C)C)[Si](C)(C)C)O[Si](C)(C)C)=C1	2295.0	Standard polar	33892256
Bupranolol,1TBDMS,isomer #1	CC1=CC=C(Cl)C(OCC(CNC(C)(C)C)O[Si](C)(C)C(C)(C)C)=C1	2141.4	Semi standard non polar	33892256
Bupranolol,1TBDMS,isomer #2	CC1=CC=C(Cl)C(OCC(O)CN(C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1	2377.5	Semi standard non polar	33892256
Bupranolol,2TBDMS,isomer #1	CC1=CC=C(Cl)C(OCC(CN(C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=C1	2624.9	Semi standard non polar	33892256
Bupranolol,2TBDMS,isomer #1	CC1=CC=C(Cl)C(OCC(CN(C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=C1	2602.3	Standard non polar	33892256
Bupranolol,2TBDMS,isomer #1	CC1=CC=C(Cl)C(OCC(CN(C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=C1	2495.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Bupranolol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4r-9410000000-4fb6e56fbfc20d328e01	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bupranolol GC-MS (1 TMS) - 70eV, Positive	splash10-052r-9211000000-af03417e0faa422d8dab	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bupranolol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bupranolol 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 - Bupranolol 10V, Positive-QTOF	splash10-00di-1390000000-a50fbc36e0a70a4174d0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bupranolol 20V, Positive-QTOF	splash10-00sd-7950000000-c35211adf59d6f487bc5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bupranolol 40V, Positive-QTOF	splash10-00du-9500000000-45c62fb606c1ef738a01	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bupranolol 10V, Negative-QTOF	splash10-00dl-1690000000-1bcf21cb4e7773e99e3e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bupranolol 20V, Negative-QTOF	splash10-0006-0900000000-87210d97bc0e2d6d0129	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bupranolol 40V, Negative-QTOF	splash10-0006-2900000000-9864230af101317a562a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bupranolol 10V, Positive-QTOF	splash10-00di-0090000000-0b8a6099373044013791	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bupranolol 20V, Positive-QTOF	splash10-05fr-9830000000-68ae42e1fc1233fddace	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bupranolol 40V, Positive-QTOF	splash10-0a4i-8900000000-43ed85ee1afba8adfc07	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bupranolol 10V, Negative-QTOF	splash10-0096-2930000000-ba5e95e24f16f97db432	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bupranolol 20V, Negative-QTOF	splash10-0006-3900000000-a5db325c0590832c3c7d	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bupranolol 40V, Negative-QTOF	splash10-001i-9300000000-5ba3afed8bc3d8638c60	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Bupranolol Action Pathway		Not Available

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 DB08808	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB08808	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB08808

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2381

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Bupranolol

METLIN ID

Not Available

PubChem Compound

2475

PDB ID

Not Available

ChEBI ID

200929

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. Beta-1 adrenergic receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: Beta-adrenergic receptors mediate the catecholamine- induced activation of adenylate cyclase through the action of G proteins. This receptor binds epinephrine and norepinephrine with approximately equal affinity
Gene Name:: ADRB1
Uniprot ID:: P08588
Molecular weight:: 51322.1

References

Zelaszczyk D, Kozlowska H, Baranowska U, Baranowska M, Reutelsterz A, Kiec-Kononowicz K, Malinowska B, Schlicker E: Four close bupranolol analogues are antagonists at the low-affinity state of beta1-adrenoceptors. J Physiol Pharmacol. 2009 Mar;60(1):51-60. [PubMed:19439807 ]

Enzyme Details

2. Beta-2 adrenergic receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: Beta-adrenergic receptors mediate the catecholamine- induced activation of adenylate cyclase through the action of G proteins. The beta-2-adrenergic receptor binds epinephrine with an approximately 30-fold greater affinity than it does norepinephrine
Gene Name:: ADRB2
Uniprot ID:: P07550
Molecular weight:: 46458.3

References

Lenard NR, Gettys TW, Dunn AJ: Activation of beta2- and beta3-adrenergic receptors increases brain tryptophan. J Pharmacol Exp Ther. 2003 May;305(2):653-9. Epub 2003 Jan 24. [PubMed:12606631 ]

Enzyme Details

3. Beta-3 adrenergic receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: Beta-adrenergic receptors mediate the catecholamine- induced activation of adenylate cyclase through the action of G proteins. Beta-3 is involved in the regulation of lipolysis and thermogenesis
Gene Name:: ADRB3
Uniprot ID:: P13945
Molecular weight:: 43518.6

References

Lenard NR, Gettys TW, Dunn AJ: Activation of beta2- and beta3-adrenergic receptors increases brain tryptophan. J Pharmacol Exp Ther. 2003 May;305(2):653-9. Epub 2003 Jan 24. [PubMed:12606631 ]
Matsushita M, Horinouchi T, Tanaka Y, Tsuru H, Koike K: Characterization of beta 3-adrenoceptor-mediated relaxation in rat abdominal aorta smooth muscle. Eur J Pharmacol. 2003 Dec 15;482(1-3):235-44. [PubMed:14660028 ]

Showing metabocard for Bupranolol (HMDB0015697)

MOL for HMDB0015697 (Bupranolol)

3D MOL for HMDB0015697 (Bupranolol)

3D SDF for HMDB0015697 (Bupranolol)

3D-SDF for HMDB0015697 (Bupranolol)

PDB for HMDB0015697 (Bupranolol)

3D PDB for HMDB0015697 (Bupranolol)

SMILES for HMDB0015697 (Bupranolol)

INCHI for HMDB0015697 (Bupranolol)

Structure for HMDB0015697 (Bupranolol)

3D Structure for HMDB0015697 (Bupranolol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References