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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (4) Show 4 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:49 UTC

HMDB ID

HMDB0015004

Secondary Accession Numbers

HMDB15004

Metabolite Identification

Common Name

Alprenolol

Description

Alprenolol is only found in individuals that have used or taken this drug. It is one of the adrenergic beta-antagonists used as an antihypertensive, anti-anginal, and anti-arrhythmic agent. [PubChem]Alprenolol non-selectively blocks beta-1 adrenergic receptors mainly in the heart, inhibiting the effects of epinephrine and norepinephrine resulting in a decrease in heart rate and blood pressure. Also, with a more minor effect, by binding beta-2 receptors in the juxtaglomerular apparatus, alprenolol inhibits the production of renin, thereby inhibiting angiotensin II and aldosterone production and therefore inhibits the vasoconstriction and water retention due to angiotensin II and aldosterone, respectively.

Structure

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

HMDB0015004
     RDKit          3D
Alprenolol
 41 41  0  0  0  0  0  0  0  0999 V2000
    5.1055    1.9256    1.1437 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9334    1.5377    0.6927 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7404    1.2966   -0.7490 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3297   -0.1070   -1.0093 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2155   -1.0217   -1.5066 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7957   -2.3292   -1.7388 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5106   -2.6993   -1.4731 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6195   -1.7574   -0.9666 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9921   -0.4575   -0.7238 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1535    0.4957   -0.2273 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1692    0.5003    0.1323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1692    0.2385   -0.9446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0176    1.2166   -1.9797 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5664    0.3593   -0.3799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7953   -0.6005    0.6541 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1752   -0.5357    1.1447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1768   -0.8658    0.0820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4513    0.8615    1.7158 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2860    2.1144    2.2089 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9691    2.0848    0.4952 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1191    1.3969    1.3721 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9385    2.0060   -1.1082 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6755    1.5529   -1.3102 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2254   -0.6883   -1.7036 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5348   -3.0013   -2.1291 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1713   -3.7187   -1.6509 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6095   -2.0807   -0.7484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3834    1.5119    0.5905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3624   -0.1981    1.0059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1084   -0.7467   -1.4169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4223    0.7943   -2.6541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2602    0.2290   -1.2440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6869    1.4149   -0.0287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2321   -0.3277    1.5101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2221   -1.2383    2.0009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3950    0.0768   -0.4969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7287   -1.6003   -0.5968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1098   -1.2639    0.5315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5879    1.1768    2.3558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5725    1.6034    0.9207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3327    0.8440    2.3822 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
  9  4  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  5 24  1  0
  6 25  1  0
  7 26  1  0
  8 27  1  0
 11 28  1  0
 11 29  1  0
 12 30  1  0
 13 31  1  0
 14 32  1  0
 14 33  1  0
 15 34  1  0
 16 35  1  0
 17 36  1  0
 17 37  1  0
 17 38  1  0
 18 39  1  0
 18 40  1  0
 18 41  1  0
M  END

866
  Mrv0541 02231215042D          

 18 18  0  0  1  0            999 V2000
    4.5080   -0.6188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.0313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    1.8563    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659    1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    3.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -3.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  7  1  0  0  0  0
  1 10  1  0  0  0  0
  2  4  1  0  0  0  0
  3  5  1  0  0  0  0
  3  6  1  0  0  0  0
  4  5  1  0  0  0  0
  4  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6  9  1  0  0  0  0
 10 11  1  0  0  0  0
 10 13  2  0  0  0  0
 11 12  1  0  0  0  0
 11 14  2  0  0  0  0
 12 17  1  0  0  0  0
 13 15  1  0  0  0  0
 14 16  1  0  0  0  0
 15 16  2  0  0  0  0
 17 18  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015004

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)NCC(O)COC1=CC=CC=C1CC=C

> <INCHI_IDENTIFIER>
InChI=1S/C15H23NO2/c1-4-7-13-8-5-6-9-15(13)18-11-14(17)10-16-12(2)3/h4-6,8-9,12,14,16-17H,1,7,10-11H2,2-3H3

> <INCHI_KEY>
PAZJSJFMUHDSTF-UHFFFAOYSA-N

> <FORMULA>
C15H23NO2

> <MOLECULAR_WEIGHT>
249.3486

> <EXACT_MASS>
249.172878985

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
29.383222905592554

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-[2-(prop-2-en-1-yl)phenoxy]-3-[(propan-2-yl)amino]propan-2-ol

> <ALOGPS_LOGP>
2.59

> <JCHEM_LOGP>
2.6927899056666664

> <ALOGPS_LOGS>
-3.12

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.087952044634939

> <JCHEM_PKA_STRONGEST_BASIC>
9.666166510504235

> <JCHEM_POLAR_SURFACE_AREA>
41.49

> <JCHEM_REFRACTIVITY>
74.66280000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.88e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-(isopropylamino)-3-[2-(prop-2-en-1-yl)phenoxy]propan-2-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015004
     RDKit          3D
Alprenolol
 41 41  0  0  0  0  0  0  0  0999 V2000
    5.1055    1.9256    1.1437 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9334    1.5377    0.6927 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7404    1.2966   -0.7490 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3297   -0.1070   -1.0093 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2155   -1.0217   -1.5066 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7957   -2.3292   -1.7388 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5106   -2.6993   -1.4731 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6195   -1.7574   -0.9666 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9921   -0.4575   -0.7238 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1535    0.4957   -0.2273 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1692    0.5003    0.1323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1692    0.2385   -0.9446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0176    1.2166   -1.9797 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5664    0.3593   -0.3799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7953   -0.6005    0.6541 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1752   -0.5357    1.1447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1768   -0.8658    0.0820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4513    0.8615    1.7158 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2860    2.1144    2.2089 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9691    2.0848    0.4952 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1191    1.3969    1.3721 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9385    2.0060   -1.1082 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6755    1.5529   -1.3102 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2254   -0.6883   -1.7036 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5348   -3.0013   -2.1291 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1713   -3.7187   -1.6509 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6095   -2.0807   -0.7484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3834    1.5119    0.5905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3624   -0.1981    1.0059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1084   -0.7467   -1.4169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4223    0.7943   -2.6541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2602    0.2290   -1.2440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6869    1.4149   -0.0287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2321   -0.3277    1.5101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2221   -1.2383    2.0009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3950    0.0768   -0.4969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7287   -1.6003   -0.5968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1098   -1.2639    0.5315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5879    1.1768    2.3558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5725    1.6034    0.9207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3327    0.8440    2.3822 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
  9  4  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  5 24  1  0
  6 25  1  0
  7 26  1  0
  8 27  1  0
 11 28  1  0
 11 29  1  0
 12 30  1  0
 13 31  1  0
 14 32  1  0
 14 33  1  0
 15 34  1  0
 16 35  1  0
 17 36  1  0
 17 37  1  0
 17 38  1  0
 18 39  1  0
 18 40  1  0
 18 41  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 866                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       8.415  -1.155   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       8.415   1.925   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0      11.082   3.465   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       9.748   1.155   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.082   1.925   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.416   4.235   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.748  -0.385   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      13.750   3.465   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.416   5.775   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.415  -2.695   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.081  -3.465   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.748  -2.695   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.748  -3.465   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.081  -5.005   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.748  -5.005   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.415  -5.775   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.414  -3.465   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.080  -2.695   0.000  0.00  0.00           C+0
CONECT    1    7   10                                                       
CONECT    2    4                                                            
CONECT    3    5    6                                                       
CONECT    4    2    5    7                                                  
CONECT    5    3    4                                                       
CONECT    6    3    8    9                                                  
CONECT    7    1    4                                                       
CONECT    8    6                                                            
CONECT    9    6                                                            
CONECT   10    1   11   13                                                  
CONECT   11   10   12   14                                                  
CONECT   12   11   17                                                       
CONECT   13   10   15                                                       
CONECT   14   11   16                                                       
CONECT   15   13   16                                                       
CONECT   16   14   15                                                       
CONECT   17   12   18                                                       
CONECT   18   17                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   36    0
END

COMPND    HMDB0015004
HETATM    1  C1  UNL     1       5.105   1.926   1.144  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.933   1.538   0.693  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.740   1.297  -0.749  1.00  0.00           C  
HETATM    4  C4  UNL     1       3.330  -0.107  -1.009  1.00  0.00           C  
HETATM    5  C5  UNL     1       4.216  -1.022  -1.507  1.00  0.00           C  
HETATM    6  C6  UNL     1       3.796  -2.329  -1.739  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.511  -2.699  -1.473  1.00  0.00           C  
HETATM    8  C8  UNL     1       1.619  -1.757  -0.967  1.00  0.00           C  
HETATM    9  C9  UNL     1       1.992  -0.458  -0.724  1.00  0.00           C  
HETATM   10  O1  UNL     1       1.153   0.496  -0.227  1.00  0.00           O  
HETATM   11  C10 UNL     1      -0.169   0.500   0.132  1.00  0.00           C  
HETATM   12  C11 UNL     1      -1.169   0.239  -0.945  1.00  0.00           C  
HETATM   13  O2  UNL     1      -1.018   1.217  -1.980  1.00  0.00           O  
HETATM   14  C12 UNL     1      -2.566   0.359  -0.380  1.00  0.00           C  
HETATM   15  N1  UNL     1      -2.795  -0.600   0.654  1.00  0.00           N  
HETATM   16  C13 UNL     1      -4.175  -0.536   1.145  1.00  0.00           C  
HETATM   17  C14 UNL     1      -5.177  -0.866   0.082  1.00  0.00           C  
HETATM   18  C15 UNL     1      -4.451   0.861   1.716  1.00  0.00           C  
HETATM   19  H1  UNL     1       5.286   2.114   2.209  1.00  0.00           H  
HETATM   20  H2  UNL     1       5.969   2.085   0.495  1.00  0.00           H  
HETATM   21  H3  UNL     1       3.119   1.397   1.372  1.00  0.00           H  
HETATM   22  H4  UNL     1       2.938   2.006  -1.108  1.00  0.00           H  
HETATM   23  H5  UNL     1       4.676   1.553  -1.310  1.00  0.00           H  
HETATM   24  H6  UNL     1       5.225  -0.688  -1.704  1.00  0.00           H  
HETATM   25  H7  UNL     1       4.535  -3.001  -2.129  1.00  0.00           H  
HETATM   26  H8  UNL     1       2.171  -3.719  -1.651  1.00  0.00           H  
HETATM   27  H9  UNL     1       0.609  -2.081  -0.748  1.00  0.00           H  
HETATM   28  H10 UNL     1      -0.383   1.512   0.590  1.00  0.00           H  
HETATM   29  H11 UNL     1      -0.362  -0.198   1.006  1.00  0.00           H  
HETATM   30  H12 UNL     1      -1.108  -0.747  -1.417  1.00  0.00           H  
HETATM   31  H13 UNL     1      -0.422   0.794  -2.654  1.00  0.00           H  
HETATM   32  H14 UNL     1      -3.260   0.229  -1.244  1.00  0.00           H  
HETATM   33  H15 UNL     1      -2.687   1.415  -0.029  1.00  0.00           H  
HETATM   34  H16 UNL     1      -2.232  -0.328   1.510  1.00  0.00           H  
HETATM   35  H17 UNL     1      -4.222  -1.238   2.001  1.00  0.00           H  
HETATM   36  H18 UNL     1      -5.395   0.077  -0.497  1.00  0.00           H  
HETATM   37  H19 UNL     1      -4.729  -1.600  -0.597  1.00  0.00           H  
HETATM   38  H20 UNL     1      -6.110  -1.264   0.532  1.00  0.00           H  
HETATM   39  H21 UNL     1      -3.588   1.177   2.356  1.00  0.00           H  
HETATM   40  H22 UNL     1      -4.573   1.603   0.921  1.00  0.00           H  
HETATM   41  H23 UNL     1      -5.333   0.844   2.382  1.00  0.00           H  
CONECT    1    2    2   19   20
CONECT    2    3   21
CONECT    3    4   22   23
CONECT    4    5    5    9
CONECT    5    6   24
CONECT    6    7    7   25
CONECT    7    8   26
CONECT    8    9    9   27
CONECT    9   10
CONECT   10   11
CONECT   11   12   28   29
CONECT   12   13   14   30
CONECT   13   31
CONECT   14   15   32   33
CONECT   15   16   34
CONECT   16   17   18   35
CONECT   17   36   37   38
CONECT   18   39   40   41
END

HMDB0015004
     RDKit          3D
Alprenolol
 41 41  0  0  0  0  0  0  0  0999 V2000
    5.1055    1.9256    1.1437 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9334    1.5377    0.6927 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7404    1.2966   -0.7490 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3297   -0.1070   -1.0093 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2155   -1.0217   -1.5066 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7957   -2.3292   -1.7388 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5106   -2.6993   -1.4731 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6195   -1.7574   -0.9666 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9921   -0.4575   -0.7238 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1535    0.4957   -0.2273 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1692    0.5003    0.1323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1692    0.2385   -0.9446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0176    1.2166   -1.9797 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5664    0.3593   -0.3799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7953   -0.6005    0.6541 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1752   -0.5357    1.1447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1768   -0.8658    0.0820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4513    0.8615    1.7158 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2860    2.1144    2.2089 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9691    2.0848    0.4952 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1191    1.3969    1.3721 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9385    2.0060   -1.1082 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6755    1.5529   -1.3102 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2254   -0.6883   -1.7036 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5348   -3.0013   -2.1291 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1713   -3.7187   -1.6509 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6095   -2.0807   -0.7484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3834    1.5119    0.5905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3624   -0.1981    1.0059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1084   -0.7467   -1.4169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4223    0.7943   -2.6541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2602    0.2290   -1.2440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6869    1.4149   -0.0287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2321   -0.3277    1.5101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2221   -1.2383    2.0009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3950    0.0768   -0.4969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7287   -1.6003   -0.5968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1098   -1.2639    0.5315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5879    1.1768    2.3558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5725    1.6034    0.9207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3327    0.8440    2.3822 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
  9  4  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  5 24  1  0
  6 25  1  0
  7 26  1  0
  8 27  1  0
 11 28  1  0
 11 29  1  0
 12 30  1  0
 13 31  1  0
 14 32  1  0
 14 33  1  0
 15 34  1  0
 16 35  1  0
 17 36  1  0
 17 37  1  0
 17 38  1  0
 18 39  1  0
 18 40  1  0
 18 41  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-(2-Allylphenoxy)-3-isopropylamino-2-propanol	ChEBI
1-(O-Allylphenoxy)-3-(isopropylamino)-2-propanol	ChEBI
Alfeprol	ChEBI
Alprenololum	ChEBI
Alpheprol	HMDB
Alprenolol hydrochloride	HMDB
AptinDuriles	HMDB
Aptina	HMDB
Astra brand OF alprenolol hydrochloride	HMDB
Aptin	HMDB
Aptine	HMDB
Made brand OF alprenolol hydrochloride	HMDB
Astra brand OF alprenolol benzoate	HMDB
Aptin duriles	HMDB
Aptin-duriles	HMDB

Chemical Formula

C₁₅H₂₃NO₂

Average Molecular Weight

249.3486

Monoisotopic Molecular Weight

249.172878985

IUPAC Name

1-[2-(prop-2-en-1-yl)phenoxy]-3-[(propan-2-yl)amino]propan-2-ol

Traditional Name

1-(isopropylamino)-3-[2-(prop-2-en-1-yl)phenoxy]propan-2-ol

CAS Registry Number

13655-52-2

SMILES

CC(C)NCC(O)COC1=CC=CC=C1CC=C

InChI Identifier

InChI=1S/C15H23NO2/c1-4-7-13-8-5-6-9-15(13)18-11-14(17)10-16-12(2)3/h4-6,8-9,12,14,16-17H,1,7,10-11H2,2-3H3

InChI Key

PAZJSJFMUHDSTF-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
Monocyclic benzene moiety
1,2-aminoalcohol
Secondary alcohol
Secondary aliphatic amine
Secondary amine
Ether
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organopnictogen compound
Amine
Organic oxygen compound
Alcohol
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

secondary alcohol (CHEBI:51211 )
secondary amino compound (CHEBI:51211 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0015004)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Alprenolol Action Pathway (PathBank: SMP0000297)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	107 - 109 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.19 g/L	Not Available
LogP	2.8	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	159.5	30932474

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.19 g/L	ALOGPS
logP	2.59	ALOGPS
logP	2.69	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	14.09	ChemAxon
pKa (Strongest Basic)	9.67	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	8	ChemAxon
Refractivity	74.66 m³·mol⁻¹	ChemAxon
Polarizability	29.38 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	159.991	31661259
DarkChem	[M-H]-	158.061	31661259
DeepCCS	[M+H]+	157.162	30932474
DeepCCS	[M-H]-	154.804	30932474
DeepCCS	[M-2H]-	188.692	30932474
DeepCCS	[M+Na]+	163.616	30932474
AllCCS	[M+H]+	162.3	32859911
AllCCS	[M+H-H2O]+	158.8	32859911
AllCCS	[M+NH4]+	165.5	32859911
AllCCS	[M+Na]+	166.4	32859911
AllCCS	[M-H]-	164.0	32859911
AllCCS	[M+Na-2H]-	164.6	32859911
AllCCS	[M+HCOO]-	165.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Alprenolol	CC(C)NCC(O)COC1=CC=CC=C1CC=C	2417.2	Standard polar	33892256
Alprenolol	CC(C)NCC(O)COC1=CC=CC=C1CC=C	1869.3	Standard non polar	33892256
Alprenolol	CC(C)NCC(O)COC1=CC=CC=C1CC=C	1826.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Alprenolol,1TMS,isomer #1	C=CCC1=CC=CC=C1OCC(CNC(C)C)O[Si](C)(C)C	1843.8	Semi standard non polar	33892256
Alprenolol,1TMS,isomer #2	C=CCC1=CC=CC=C1OCC(O)CN(C(C)C)[Si](C)(C)C	2015.5	Semi standard non polar	33892256
Alprenolol,2TMS,isomer #1	C=CCC1=CC=CC=C1OCC(CN(C(C)C)[Si](C)(C)C)O[Si](C)(C)C	2061.3	Semi standard non polar	33892256
Alprenolol,2TMS,isomer #1	C=CCC1=CC=CC=C1OCC(CN(C(C)C)[Si](C)(C)C)O[Si](C)(C)C	2083.7	Standard non polar	33892256
Alprenolol,2TMS,isomer #1	C=CCC1=CC=CC=C1OCC(CN(C(C)C)[Si](C)(C)C)O[Si](C)(C)C	2323.8	Standard polar	33892256
Alprenolol,1TBDMS,isomer #1	C=CCC1=CC=CC=C1OCC(CNC(C)C)O[Si](C)(C)C(C)(C)C	2060.5	Semi standard non polar	33892256
Alprenolol,1TBDMS,isomer #2	C=CCC1=CC=CC=C1OCC(O)CN(C(C)C)[Si](C)(C)C(C)(C)C	2267.2	Semi standard non polar	33892256
Alprenolol,2TBDMS,isomer #1	C=CCC1=CC=CC=C1OCC(CN(C(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2526.5	Semi standard non polar	33892256
Alprenolol,2TBDMS,isomer #1	C=CCC1=CC=CC=C1OCC(CN(C(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2500.7	Standard non polar	33892256
Alprenolol,2TBDMS,isomer #1	C=CCC1=CC=CC=C1OCC(CN(C(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2526.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Alprenolol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0089-8920000000-21e1f9aacdf6f681239a	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Alprenolol GC-MS (1 TMS) - 70eV, Positive	splash10-000x-3911000000-c0508ebc2143aa8f5821	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Alprenolol 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 - Alprenolol 10V, Positive-QTOF	splash10-0udi-2390000000-b40bd20c564639646d59	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alprenolol 20V, Positive-QTOF	splash10-00xu-9840000000-b699adf3065f5f8a80a9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alprenolol 40V, Positive-QTOF	splash10-006x-9200000000-38c31766bb53b5388936	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alprenolol 10V, Negative-QTOF	splash10-000t-1790000000-9b9b80a1076fdfb513b5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alprenolol 20V, Negative-QTOF	splash10-001i-1900000000-5b3c063605beb0203b32	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alprenolol 40V, Negative-QTOF	splash10-001l-5900000000-1e30f9cbcedc79974a16	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alprenolol 10V, Positive-QTOF	splash10-0udi-0090000000-ebc8021939e29e76e29b	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alprenolol 20V, Positive-QTOF	splash10-00xs-9410000000-bdcec11d9de911234e56	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alprenolol 40V, Positive-QTOF	splash10-0abc-9300000000-c05013c8c607b53957ec	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alprenolol 10V, Negative-QTOF	splash10-0002-1930000000-654f956176d89c449364	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alprenolol 20V, Negative-QTOF	splash10-001i-3900000000-d1e7ef0730ac98b18463	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alprenolol 40V, Negative-QTOF	splash10-0a59-9500000000-3126ac2735ee817eaba9	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
Alprenolol 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 DB00866	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00866	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00866

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2035

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Alprenolol

METLIN ID

Not Available

PubChem Compound

2119

PDB ID

Not Available

ChEBI ID

51211

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. Cytochrome P450 2D6

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:: CYP2D6
Uniprot ID:: P10635
Molecular weight:: 55768.94

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

2. 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

Surman AJ, Doggrell SA: Alprenolol and bromoacetylalprenololmenthane are competitive slowly reversible antagonists at the beta 1-adrenoceptors of rat left atria. J Cardiovasc Pharmacol. 1993 Jan;21(1):35-9. [PubMed:7678677 ]
De Ponti F, Cosentino M, Costa A, Girani M, Gibelli G, D'Angelo L, Frigo G, Crema A: Inhibitory effects of SR 58611A on canine colonic motility: evidence for a role of beta 3-adrenoceptors. Br J Pharmacol. 1995 Apr;114(7):1447-53. [PubMed:7606348 ]
Varma DR, Shen H, Deng XF, Peri KG, Chemtob S, Mulay S: Inverse agonist activities of beta-adrenoceptor antagonists in rat myocardium. Br J Pharmacol. 1999 Jun;127(4):895-902. [PubMed:10433496 ]
Brahmadevara N, Shaw AM, MacDonald A: Evidence against beta 3-adrenoceptors or low affinity state of beta 1-adrenoceptors mediating relaxation in rat isolated aorta. Br J Pharmacol. 2003 Jan;138(1):99-106. [PubMed:12522078 ]
Im MJ, Holzhofer A, Bottinger H, Pfeuffer T, Helmreich EJ: Interactions of pure beta gamma-subunits of G-proteins with purified beta 1-adrenoceptor. FEBS Lett. 1988 Jan 25;227(2):225-9. [PubMed:2828119 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzyme Details

3. 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

Brodde OE, Wang XL, O'Hara N, Daul A, Schiess W: Effect of propranolol, alprenolol, pindolol, and bopindolol on beta 2-adrenoceptor density in human lymphocytes. J Cardiovasc Pharmacol. 1986;8 Suppl 6:S70-3. [PubMed:2439825 ]
Brodde OE, Daul A, Stuka N, O'Hara N, Borchard U: Effects of beta-adrenoceptor antagonist administration on beta 2-adrenoceptor density in human lymphocytes. The role of the "intrinsic sympathomimetic activity". Naunyn Schmiedebergs Arch Pharmacol. 1985 Feb;328(4):417-22. [PubMed:2859531 ]
Abrahamsson T: The beta 1- and beta 2-adrenoceptor stimulatory effects of alprenolol, oxprenolol and pindolol: a study in the isolated right atrium and uterus of the rat. Br J Pharmacol. 1986 Apr;87(4):657-64. [PubMed:2871880 ]

Enzyme Details

4. 5-hydroxytryptamine receptor 1A

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. The activity of this receptor is mediated by G proteins that inhibit adenylate cyclase activity
Gene Name:: HTR1A
Uniprot ID:: P08908
Molecular weight:: 46106.3

References

Millan MJ, Rivet JM, Canton H, Lejeune F, Bervoets K, Brocco M, Gobert A, Lefebvre de Ladonchamps B, Le Marouille-Girardon S, Verriele L, et al.: S 14671: a naphtylpiperazine 5-hydroxytryptamine1A agonist of exceptional potency and high efficacy possessing antagonist activity at 5-hydroxytryptamine1C/2 receptors. J Pharmacol Exp Ther. 1992 Aug;262(2):451-63. [PubMed:1323650 ]
Darmani NA: Role of the inhibitory adrenergic alpha 2 and serotonergic 5-HT1A components of cocaine's actions on the DOI-induced head-twitch response in 5-HT2-receptor supersensitive mice. Pharmacol Biochem Behav. 1993 Jun;45(2):269-74. [PubMed:8392199 ]
Kuipers W, Link R, Standaar PJ, Stoit AR, Van Wijngaarden I, Leurs R, Ijzerman AP: Study of the interaction between aryloxypropanolamines and Asn386 in helix VII of the human 5-hydroxytryptamine1A receptor. Mol Pharmacol. 1997 May;51(5):889-96. [PubMed:9145928 ]
Misane I, Johansson C, Ogren SO: Analysis of the 5-HT1A receptor involvement in passive avoidance in the rat. Br J Pharmacol. 1998 Oct;125(3):499-509. [PubMed:9806333 ]

Showing metabocard for Alprenolol (HMDB0015004)

MOL for HMDB0015004 (Alprenolol)

3D MOL for HMDB0015004 (Alprenolol)

3D SDF for HMDB0015004 (Alprenolol)

3D-SDF for HMDB0015004 (Alprenolol)

PDB for HMDB0015004 (Alprenolol)

3D PDB for HMDB0015004 (Alprenolol)

SMILES for HMDB0015004 (Alprenolol)

INCHI for HMDB0015004 (Alprenolol)

Structure for HMDB0015004 (Alprenolol)

3D Structure for HMDB0015004 (Alprenolol)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

References