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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 03:57:06 UTC

Update Date

2021-09-26 23:00:20 UTC

HMDB ID

HMDB0249440

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Bunitrolol

Description

Bunitrolol belongs to the class of organic compounds known as phenol ethers. These are aromatic compounds containing an ether group substituted with a benzene ring. Bunitrolol is a beta-adrenergic antagonist. Bunitrolol is a very strong basic compound (based on its pKa). This compound has been identified in human blood as reported by (PMID: 31557052 ). Bunitrolol is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Bunitrolol is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0249440
     RDKit          3D
Bunitrolol
 38 38  0  0  0  0  0  0  0  0999 V2000
   -4.3329   -0.4412    1.0036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0925    0.2709    0.4779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5757    1.1267    1.6060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4751    1.1661   -0.6612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1674   -0.7504    0.0655 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0477   -0.2558   -0.6815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1740   -1.4820   -1.0124 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2321   -2.0585    0.1542 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8906   -1.1394   -1.9961 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8552   -0.2647   -1.6762 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8824   -0.0589   -0.8449 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3354   -0.9104    0.1285 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4078   -0.6279    0.9504 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0594    0.5682    0.7881 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6614    1.4704   -0.1678 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5980    1.1558   -0.9599 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1464    2.0809   -1.9822 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8037    2.8320   -2.7951 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1808   -1.5488    1.0716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1873   -0.3236    0.2908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6109   -0.1163    2.0270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0805    2.1148    1.6085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8614    0.6485    2.5885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4972    1.3090    1.5708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4398    1.6693   -0.4083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7259    1.9873   -0.7096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6013    0.6349   -1.6198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8496   -1.3280    0.8579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4184    0.3873   -0.0465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3667    0.2373   -1.6043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8787   -2.2131   -1.4980 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3416   -3.0509    0.0849 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3601   -0.9015   -2.9724 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3686   -2.1503   -2.2648 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8310   -1.8743    0.2522 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7027   -1.3615    1.7010 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8943    0.7877    1.4276 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1928    2.4108   -0.2776 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  3  0
 16 11  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
  8 32  1  0
  9 33  1  0
  9 34  1  0
 12 35  1  0
 13 36  1  0
 14 37  1  0
 15 38  1  0
M  END

  Mrv1652306031607112D          

 18 18  0  0  0  0            999 V2000
   -2.1434    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8414    4.2355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0164    5.6645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
 11  6  2  0  0  0  0
 11  8  1  0  0  0  0
 12  9  1  0  0  0  0
 12 10  1  0  0  0  0
 13  7  2  0  0  0  0
 13 11  1  0  0  0  0
 14  1  1  0  0  0  0
 14  2  1  0  0  0  0
 14  3  1  0  0  0  0
 15  8  3  0  0  0  0
 16  9  1  0  0  0  0
 16 14  1  0  0  0  0
 17 12  1  0  0  0  0
 18 10  1  0  0  0  0
 18 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0249440

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)(C)NCC(O)COC1=CC=CC=C1C#N

> <INCHI_IDENTIFIER>
InChI=1S/C14H20N2O2/c1-14(2,3)16-9-12(17)10-18-13-7-5-4-6-11(13)8-15/h4-7,12,16-17H,9-10H2,1-3H3

> <INCHI_KEY>
VCVQSRCYSKKPBA-UHFFFAOYSA-N

> <FORMULA>
C14H20N2O2

> <MOLECULAR_WEIGHT>
248.326

> <EXACT_MASS>
248.152477892

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
27.673141274329176

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[3-(tert-butylamino)-2-hydroxypropoxy]benzonitrile

> <ALOGPS_LOGP>
1.84

> <JCHEM_LOGP>
1.7308920293333332

> <ALOGPS_LOGS>
-3.21

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.087515236517834

> <JCHEM_PKA_STRONGEST_BASIC>
9.75952291634702

> <JCHEM_POLAR_SURFACE_AREA>
65.28

> <JCHEM_REFRACTIVITY>
70.73530000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.55e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
bunitrolol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0249440
     RDKit          3D
Bunitrolol
 38 38  0  0  0  0  0  0  0  0999 V2000
   -4.3329   -0.4412    1.0036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0925    0.2709    0.4779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5757    1.1267    1.6060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4751    1.1661   -0.6612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1674   -0.7504    0.0655 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0477   -0.2558   -0.6815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1740   -1.4820   -1.0124 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2321   -2.0585    0.1542 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8906   -1.1394   -1.9961 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8552   -0.2647   -1.6762 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8824   -0.0589   -0.8449 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3354   -0.9104    0.1285 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4078   -0.6279    0.9504 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0594    0.5682    0.7881 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6614    1.4704   -0.1678 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5980    1.1558   -0.9599 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1464    2.0809   -1.9822 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8037    2.8320   -2.7951 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1808   -1.5488    1.0716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1873   -0.3236    0.2908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6109   -0.1163    2.0270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0805    2.1148    1.6085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8614    0.6485    2.5885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4972    1.3090    1.5708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4398    1.6693   -0.4083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7259    1.9873   -0.7096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6013    0.6349   -1.6198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8496   -1.3280    0.8579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4184    0.3873   -0.0465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3667    0.2373   -1.6043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8787   -2.2131   -1.4980 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3416   -3.0509    0.0849 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3601   -0.9015   -2.9724 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3686   -2.1503   -2.2648 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8310   -1.8743    0.2522 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7027   -1.3615    1.7010 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8943    0.7877    1.4276 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1928    2.4108   -0.2776 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  3  0
 16 11  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
  8 32  1  0
  9 33  1  0
  9 34  1  0
 12 35  1  0
 13 36  1  0
 14 37  1  0
 15 38  1  0
M  END

HEADER    PROTEIN                                 03-JUN-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-JUN-16         0                                  
HETATM    1  C   UNK     0      -4.001  10.010   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.437   7.906   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.897  10.574   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.667   9.240   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0      -2.667   3.080   0.000  0.00  0.00           N+0
HETATM   16  N   UNK     0      -1.334   8.470   0.000  0.00  0.00           N+0
HETATM   17  O   UNK     0       1.334   6.930   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
CONECT    1   14                                                            
CONECT    2   14                                                            
CONECT    3   14                                                            
CONECT    4    5    6                                                       
CONECT    5    4    7                                                       
CONECT    6    4   11                                                       
CONECT    7    5   13                                                       
CONECT    8   11   15                                                       
CONECT    9   12   16                                                       
CONECT   10   12   18                                                       
CONECT   11    6    8   13                                                  
CONECT   12    9   10   17                                                  
CONECT   13    7   11   18                                                  
CONECT   14    1    2    3   16                                             
CONECT   15    8                                                            
CONECT   16    9   14                                                       
CONECT   17   12                                                            
CONECT   18   10   13                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   36    0
END

COMPND    HMDB0249440
HETATM    1  C1  UNL     1      -4.333  -0.441   1.004  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.093   0.271   0.478  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.576   1.127   1.606  1.00  0.00           C  
HETATM    4  C4  UNL     1      -3.475   1.166  -0.661  1.00  0.00           C  
HETATM    5  N1  UNL     1      -2.167  -0.750   0.065  1.00  0.00           N  
HETATM    6  C5  UNL     1      -1.048  -0.256  -0.682  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.174  -1.482  -1.012  1.00  0.00           C  
HETATM    8  O1  UNL     1       0.232  -2.058   0.154  1.00  0.00           O  
HETATM    9  C7  UNL     1       0.891  -1.139  -1.996  1.00  0.00           C  
HETATM   10  O2  UNL     1       1.855  -0.265  -1.676  1.00  0.00           O  
HETATM   11  C8  UNL     1       2.882  -0.059  -0.845  1.00  0.00           C  
HETATM   12  C9  UNL     1       3.335  -0.910   0.129  1.00  0.00           C  
HETATM   13  C10 UNL     1       4.408  -0.628   0.950  1.00  0.00           C  
HETATM   14  C11 UNL     1       5.059   0.568   0.788  1.00  0.00           C  
HETATM   15  C12 UNL     1       4.661   1.470  -0.168  1.00  0.00           C  
HETATM   16  C13 UNL     1       3.598   1.156  -0.960  1.00  0.00           C  
HETATM   17  C14 UNL     1       3.146   2.081  -1.982  1.00  0.00           C  
HETATM   18  N2  UNL     1       2.804   2.832  -2.795  1.00  0.00           N  
HETATM   19  H1  UNL     1      -4.181  -1.549   1.072  1.00  0.00           H  
HETATM   20  H2  UNL     1      -5.187  -0.324   0.291  1.00  0.00           H  
HETATM   21  H3  UNL     1      -4.611  -0.116   2.027  1.00  0.00           H  
HETATM   22  H4  UNL     1      -3.081   2.115   1.609  1.00  0.00           H  
HETATM   23  H5  UNL     1      -2.861   0.648   2.588  1.00  0.00           H  
HETATM   24  H6  UNL     1      -1.497   1.309   1.571  1.00  0.00           H  
HETATM   25  H7  UNL     1      -4.440   1.669  -0.408  1.00  0.00           H  
HETATM   26  H8  UNL     1      -2.726   1.987  -0.710  1.00  0.00           H  
HETATM   27  H9  UNL     1      -3.601   0.635  -1.620  1.00  0.00           H  
HETATM   28  H10 UNL     1      -1.850  -1.328   0.858  1.00  0.00           H  
HETATM   29  H11 UNL     1      -0.418   0.387  -0.046  1.00  0.00           H  
HETATM   30  H12 UNL     1      -1.367   0.237  -1.604  1.00  0.00           H  
HETATM   31  H13 UNL     1      -0.879  -2.213  -1.498  1.00  0.00           H  
HETATM   32  H14 UNL     1       0.342  -3.051   0.085  1.00  0.00           H  
HETATM   33  H15 UNL     1       0.360  -0.902  -2.972  1.00  0.00           H  
HETATM   34  H16 UNL     1       1.369  -2.150  -2.265  1.00  0.00           H  
HETATM   35  H17 UNL     1       2.831  -1.874   0.252  1.00  0.00           H  
HETATM   36  H18 UNL     1       4.703  -1.361   1.701  1.00  0.00           H  
HETATM   37  H19 UNL     1       5.894   0.788   1.428  1.00  0.00           H  
HETATM   38  H20 UNL     1       5.193   2.411  -0.278  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3    4    5
CONECT    3   22   23   24
CONECT    4   25   26   27
CONECT    5    6   28
CONECT    6    7   29   30
CONECT    7    8    9   31
CONECT    8   32
CONECT    9   10   33   34
CONECT   10   11
CONECT   11   12   12   16
CONECT   12   13   35
CONECT   13   14   14   36
CONECT   14   15   37
CONECT   15   16   16   38
CONECT   16   17
CONECT   17   18   18   18
END

HMDB0249440
     RDKit          3D
Bunitrolol
 38 38  0  0  0  0  0  0  0  0999 V2000
   -4.3329   -0.4412    1.0036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0925    0.2709    0.4779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5757    1.1267    1.6060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4751    1.1661   -0.6612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1674   -0.7504    0.0655 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0477   -0.2558   -0.6815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1740   -1.4820   -1.0124 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2321   -2.0585    0.1542 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8906   -1.1394   -1.9961 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8552   -0.2647   -1.6762 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8824   -0.0589   -0.8449 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3354   -0.9104    0.1285 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4078   -0.6279    0.9504 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0594    0.5682    0.7881 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6614    1.4704   -0.1678 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5980    1.1558   -0.9599 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1464    2.0809   -1.9822 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8037    2.8320   -2.7951 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1808   -1.5488    1.0716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1873   -0.3236    0.2908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6109   -0.1163    2.0270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0805    2.1148    1.6085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8614    0.6485    2.5885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4972    1.3090    1.5708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4398    1.6693   -0.4083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7259    1.9873   -0.7096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6013    0.6349   -1.6198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8496   -1.3280    0.8579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4184    0.3873   -0.0465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3667    0.2373   -1.6043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8787   -2.2131   -1.4980 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3416   -3.0509    0.0849 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3601   -0.9015   -2.9724 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3686   -2.1503   -2.2648 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8310   -1.8743    0.2522 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7027   -1.3615    1.7010 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8943    0.7877    1.4276 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1928    2.4108   -0.2776 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  3  0
 16 11  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
  8 32  1  0
  9 33  1  0
  9 34  1  0
 12 35  1  0
 13 36  1  0
 14 37  1  0
 15 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Bunitrolol HCL	ChEMBL

Chemical Formula

C₁₄H₂₀N₂O₂

Average Molecular Weight

248.326

Monoisotopic Molecular Weight

248.152477892

IUPAC Name

2-[3-(tert-butylamino)-2-hydroxypropoxy]benzonitrile

Traditional Name

bunitrolol

CAS Registry Number

Not Available

SMILES

CC(C)(C)NCC(O)COC1=CC=CC=C1C#N

InChI Identifier

InChI=1S/C14H20N2O2/c1-14(2,3)16-9-12(17)10-18-13-7-5-4-6-11(13)8-15/h4-7,12,16-17H,9-10H2,1-3H3

InChI Key

VCVQSRCYSKKPBA-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
Benzonitrile
Phenol ether
Alkyl aryl ether
Monocyclic benzene moiety
1,2-aminoalcohol
Secondary alcohol
Secondary aliphatic amine
Ether
Carbonitrile
Nitrile
Secondary amine
Alcohol
Organic nitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Amine
Organonitrogen compound
Organooxygen compound
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: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	1.84	ALOGPS
logP	1.73	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	14.09	ChemAxon
pKa (Strongest Basic)	9.76	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	65.28 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	70.74 m³·mol⁻¹	ChemAxon
Polarizability	27.67 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	158.146	30932474
DeepCCS	[M-H]-	155.788	30932474
DeepCCS	[M-2H]-	189.694	30932474
DeepCCS	[M+Na]+	164.636	30932474
AllCCS	[M+H]+	157.9	32859911
AllCCS	[M+H-H2O]+	154.5	32859911
AllCCS	[M+NH4]+	161.1	32859911
AllCCS	[M+Na]+	162.0	32859911
AllCCS	[M-H]-	162.0	32859911
AllCCS	[M+Na-2H]-	162.5	32859911
AllCCS	[M+HCOO]-	163.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Bunitrolol	CC(C)(C)NCC(O)COC1=CC=CC=C1C#N	2663.0	Standard polar	33892256
Bunitrolol	CC(C)(C)NCC(O)COC1=CC=CC=C1C#N	1868.5	Standard non polar	33892256
Bunitrolol	CC(C)(C)NCC(O)COC1=CC=CC=C1C#N	1932.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Bunitrolol,2TMS,isomer #1	CC(C)(C)N(CC(COC1=CC=CC=C1C#N)O[Si](C)(C)C)[Si](C)(C)C	2201.1	Semi standard non polar	33892256
Bunitrolol,2TMS,isomer #1	CC(C)(C)N(CC(COC1=CC=CC=C1C#N)O[Si](C)(C)C)[Si](C)(C)C	2163.9	Standard non polar	33892256
Bunitrolol,2TMS,isomer #1	CC(C)(C)N(CC(COC1=CC=CC=C1C#N)O[Si](C)(C)C)[Si](C)(C)C	2538.8	Standard polar	33892256
Bunitrolol,2TBDMS,isomer #1	CC(C)(C)N(CC(COC1=CC=CC=C1C#N)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2709.7	Semi standard non polar	33892256
Bunitrolol,2TBDMS,isomer #1	CC(C)(C)N(CC(COC1=CC=CC=C1C#N)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2595.8	Standard non polar	33892256
Bunitrolol,2TBDMS,isomer #1	CC(C)(C)N(CC(COC1=CC=CC=C1C#N)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2708.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Bunitrolol GC-MS (Non-derivatized) - 70eV, Positive	splash10-05xc-9710000000-70c1ddf8bd11c94273aa	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bunitrolol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bunitrolol GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bunitrolol GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bunitrolol GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bunitrolol GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	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 - Bunitrolol 10V, Positive-QTOF	splash10-0002-1390000000-b9247a116c5d8ccadba7	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bunitrolol 20V, Positive-QTOF	splash10-00a9-7940000000-456d225093c73aa4c110	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bunitrolol 40V, Positive-QTOF	splash10-00di-9200000000-2300e9b93359c6626e40	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bunitrolol 10V, Negative-QTOF	splash10-00kb-1690000000-c6c050b78ac07d38c756	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bunitrolol 20V, Negative-QTOF	splash10-014i-1900000000-f3c4d1271bc91efc6704	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bunitrolol 40V, Negative-QTOF	splash10-00kf-9400000000-a1c2ec2200f008158131	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bunitrolol 10V, Positive-QTOF	splash10-0002-0390000000-5f3d087e4ba20dba7dcb	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bunitrolol 20V, Positive-QTOF	splash10-00di-5900000000-11930844fc80157c7787	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bunitrolol 40V, Positive-QTOF	splash10-0a4i-9400000000-3692c72c5bf976b5ce99	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bunitrolol 10V, Negative-QTOF	splash10-014j-0960000000-6b0637050e38a6208d00	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bunitrolol 20V, Negative-QTOF	splash10-014i-1900000000-c7db937a86633a9b1c41	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bunitrolol 40V, Negative-QTOF	splash10-02t9-6900000000-eafda8760d1e635c0de5	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Bunitrolol

METLIN ID

Not Available

PubChem Compound

2473

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Bunitrolol (HMDB0249440)

MOL for HMDB0249440 (Bunitrolol)

3D MOL for HMDB0249440 (Bunitrolol)

3D SDF for HMDB0249440 (Bunitrolol)

3D-SDF for HMDB0249440 (Bunitrolol)

PDB for HMDB0249440 (Bunitrolol)

3D PDB for HMDB0249440 (Bunitrolol)

SMILES for HMDB0249440 (Bunitrolol)

INCHI for HMDB0249440 (Bunitrolol)

Structure for HMDB0249440 (Bunitrolol)

3D Structure for HMDB0249440 (Bunitrolol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra