Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2) Show 2 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:52 UTC

Update Date

2022-03-07 02:51:59 UTC

HMDB ID

HMDB0015447

Secondary Accession Numbers

HMDB15447

Metabolite Identification

Common Name

Penbutolol

Description

Penbutolol is only found in individuals that have used or taken this drug. It is a medication in the class of beta blockers, used in the treatment of high blood pressure. [Wikipedia ]Penbutolol competes with adrenergic neurotransmitters such as catecholamines for binding at beta(1)-adrenergic receptors in the heart and vascular smooth muscle and beta(2)-receptors in the bronchial and vascular smooth muscle. Beta(1)-receptor blockade results in a decrease in resting and exercise heart rate and cardiac output, a decrease in both systolic and diastolic blood pressure, and, possibly, a reduction in reflex orthostatic hypotension.

Structure

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

HMDB0015447
     RDKit          3D
Penbutolol
 50 51  0  0  0  0  0  0  0  0999 V2000
   -4.8793    1.6345   -0.9287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7646    0.1536   -0.6581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6464   -0.1269    0.5464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2949   -0.6771   -1.8028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3790   -0.1459   -0.3803 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8731    0.4778    0.7852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4410    0.0821    1.0627 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1067    0.7547    2.2581 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5646    0.5841   -0.0548 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7845    0.4037    0.1370 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5488   -0.7191    0.2492 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0544   -2.0053    0.1502 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8695   -3.1398    0.2687 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2223   -2.9747    0.4929 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7595   -1.7053    0.5975 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9333   -0.6312    0.4764 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4797    0.7434    0.5631 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8380    0.8584    1.1331 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8573    0.8623    0.0459 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0923    0.9111   -1.2586 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6871    1.2689   -0.8616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7964    2.1732    0.0318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7974    1.8943   -1.4966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0270    1.9391   -1.5825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6770   -0.2579    0.1595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3787   -1.0777    1.0567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6683    0.7386    1.2375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1810   -1.3088   -1.4965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5273   -1.3753   -2.1785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6524   -0.0781   -2.6521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7935   -0.1663   -1.2128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4699    0.2975    1.6996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8972    1.5864    0.6242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3569   -0.9803    1.2591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4434    0.1972    2.7395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7669    1.6750   -0.1618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8544    0.0734   -0.9923 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0215   -2.2221   -0.0409 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4692   -4.1419    0.1877 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9146   -3.8092    0.5968 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8217   -1.5579    0.7711 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7449    1.3960    1.0425 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8836    1.8411    1.6924 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1226    0.1042    1.8876 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5184   -0.0346    0.0493 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5104    1.7518    0.1386 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1117   -0.0791   -1.7709 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4985    1.7209   -1.9132 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4766    2.3469   -0.9200 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0170    0.7438   -1.5776 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  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 16 11  1  0
 21 17  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  0
  6 32  1  0
  6 33  1  0
  7 34  1  1
  8 35  1  0
  9 36  1  0
  9 37  1  0
 12 38  1  0
 13 39  1  0
 14 40  1  0
 15 41  1  0
 17 42  1  0
 18 43  1  0
 18 44  1  0
 19 45  1  0
 19 46  1  0
 20 47  1  0
 20 48  1  0
 21 49  1  0
 21 50  1  0
M  END

1359
  Mrv0541 02231215242D          

 21 22  0  0  1  0            999 V2000
    5.9370   -0.2223    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.6028    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.2223    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659    0.6028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0334    1.0877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6985    1.0877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7784    1.8723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9534    1.8723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659   -0.2223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515   -0.6348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0804   -0.6348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.6348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.2223    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7935   -0.6348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -0.6348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515   -1.4598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0804   -1.4598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -1.3492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    0.0797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.0473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659   -1.8723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 10  1  0  0  0  0
  1 15  1  0  0  0  0
 13  2  1  6  0  0  0
  3 12  1  0  0  0  0
  3 14  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  4  9  1  0  0  0  0
  5  7  1  0  0  0  0
  6  8  1  0  0  0  0
  7  8  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
 10 16  2  0  0  0  0
 11 17  1  0  0  0  0
 12 18  1  0  0  0  0
 12 19  1  0  0  0  0
 12 20  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 16 21  1  0  0  0  0
 17 21  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015447

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)(C)NC[C@H](O)COC1=CC=CC=C1C1CCCC1

> <INCHI_IDENTIFIER>
InChI=1S/C18H29NO2/c1-18(2,3)19-12-15(20)13-21-17-11-7-6-10-16(17)14-8-4-5-9-14/h6-7,10-11,14-15,19-20H,4-5,8-9,12-13H2,1-3H3/t15-/m0/s1

> <INCHI_KEY>
KQXKVJAGOJTNJS-HNNXBMFYSA-N

> <FORMULA>
C18H29NO2

> <MOLECULAR_WEIGHT>
291.4284

> <EXACT_MASS>
291.219829177

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
34.57855846758339

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-1-(tert-butylamino)-3-(2-cyclopentylphenoxy)propan-2-ol

> <ALOGPS_LOGP>
3.84

> <JCHEM_LOGP>
3.545216419

> <ALOGPS_LOGS>
-4.14

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.087581172508457

> <JCHEM_PKA_STRONGEST_BASIC>
9.75952324837285

> <JCHEM_POLAR_SURFACE_AREA>
41.49

> <JCHEM_REFRACTIVITY>
86.60430000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.12e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-1-(tert-butylamino)-3-(2-cyclopentylphenoxy)propan-2-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015447
     RDKit          3D
Penbutolol
 50 51  0  0  0  0  0  0  0  0999 V2000
   -4.8793    1.6345   -0.9287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7646    0.1536   -0.6581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6464   -0.1269    0.5464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2949   -0.6771   -1.8028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3790   -0.1459   -0.3803 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8731    0.4778    0.7852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4410    0.0821    1.0627 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1067    0.7547    2.2581 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5646    0.5841   -0.0548 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7845    0.4037    0.1370 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5488   -0.7191    0.2492 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0544   -2.0053    0.1502 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8695   -3.1398    0.2687 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2223   -2.9747    0.4929 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7595   -1.7053    0.5975 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9333   -0.6312    0.4764 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4797    0.7434    0.5631 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8380    0.8584    1.1331 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8573    0.8623    0.0459 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0923    0.9111   -1.2586 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6871    1.2689   -0.8616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7964    2.1732    0.0318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7974    1.8943   -1.4966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0270    1.9391   -1.5825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6770   -0.2579    0.1595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3787   -1.0777    1.0567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6683    0.7386    1.2375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1810   -1.3088   -1.4965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5273   -1.3753   -2.1785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6524   -0.0781   -2.6521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7935   -0.1663   -1.2128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4699    0.2975    1.6996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8972    1.5864    0.6242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3569   -0.9803    1.2591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4434    0.1972    2.7395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7669    1.6750   -0.1618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8544    0.0734   -0.9923 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0215   -2.2221   -0.0409 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4692   -4.1419    0.1877 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9146   -3.8092    0.5968 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8217   -1.5579    0.7711 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7449    1.3960    1.0425 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8836    1.8411    1.6924 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1226    0.1042    1.8876 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5184   -0.0346    0.0493 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5104    1.7518    0.1386 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1117   -0.0791   -1.7709 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4985    1.7209   -1.9132 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4766    2.3469   -0.9200 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0170    0.7438   -1.5776 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  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 16 11  1  0
 21 17  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  0
  6 32  1  0
  6 33  1  0
  7 34  1  1
  8 35  1  0
  9 36  1  0
  9 37  1  0
 12 38  1  0
 13 39  1  0
 14 40  1  0
 15 41  1  0
 17 42  1  0
 18 43  1  0
 18 44  1  0
 19 45  1  0
 19 46  1  0
 20 47  1  0
 20 48  1  0
 21 49  1  0
 21 50  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1359                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      11.082  -0.415   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       8.415   1.125   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0       5.748  -0.415   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      13.750   1.125   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      14.996   2.030   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.504   2.030   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      14.520   3.495   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.980   3.495   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      13.750  -0.415   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.416  -1.185   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      15.083  -1.185   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.414  -1.185   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.415  -0.415   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.081  -1.185   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.748  -1.185   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.416  -2.725   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      15.083  -2.725   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.184  -2.519   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.644   0.149   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.080  -1.955   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.750  -3.495   0.000  0.00  0.00           C+0
CONECT    1   10   15                                                       
CONECT    2   13                                                            
CONECT    3   12   14                                                       
CONECT    4    5    6    9                                                  
CONECT    5    4    7                                                       
CONECT    6    4    8                                                       
CONECT    7    5    8                                                       
CONECT    8    6    7                                                       
CONECT    9    4   10   11                                                  
CONECT   10    1    9   16                                                  
CONECT   11    9   17                                                       
CONECT   12    3   18   19   20                                             
CONECT   13    2   14   15                                                  
CONECT   14    3   13                                                       
CONECT   15    1   13                                                       
CONECT   16   10   21                                                       
CONECT   17   11   21                                                       
CONECT   18   12                                                            
CONECT   19   12                                                            
CONECT   20   12                                                            
CONECT   21   16   17                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

COMPND    HMDB0015447
HETATM    1  C1  UNL     1      -4.879   1.635  -0.929  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.765   0.154  -0.658  1.00  0.00           C  
HETATM    3  C3  UNL     1      -5.646  -0.127   0.546  1.00  0.00           C  
HETATM    4  C4  UNL     1      -5.295  -0.677  -1.803  1.00  0.00           C  
HETATM    5  N1  UNL     1      -3.379  -0.146  -0.380  1.00  0.00           N  
HETATM    6  C5  UNL     1      -2.873   0.478   0.785  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.441   0.082   1.063  1.00  0.00           C  
HETATM    8  O1  UNL     1      -1.107   0.755   2.258  1.00  0.00           O  
HETATM    9  C7  UNL     1      -0.565   0.584  -0.055  1.00  0.00           C  
HETATM   10  O2  UNL     1       0.784   0.404   0.137  1.00  0.00           O  
HETATM   11  C8  UNL     1       1.549  -0.719   0.249  1.00  0.00           C  
HETATM   12  C9  UNL     1       1.054  -2.005   0.150  1.00  0.00           C  
HETATM   13  C10 UNL     1       1.869  -3.140   0.269  1.00  0.00           C  
HETATM   14  C11 UNL     1       3.222  -2.975   0.493  1.00  0.00           C  
HETATM   15  C12 UNL     1       3.760  -1.705   0.597  1.00  0.00           C  
HETATM   16  C13 UNL     1       2.933  -0.631   0.476  1.00  0.00           C  
HETATM   17  C14 UNL     1       3.480   0.743   0.563  1.00  0.00           C  
HETATM   18  C15 UNL     1       4.838   0.858   1.133  1.00  0.00           C  
HETATM   19  C16 UNL     1       5.857   0.862   0.046  1.00  0.00           C  
HETATM   20  C17 UNL     1       5.092   0.911  -1.259  1.00  0.00           C  
HETATM   21  C18 UNL     1       3.687   1.269  -0.862  1.00  0.00           C  
HETATM   22  H1  UNL     1      -4.796   2.173   0.032  1.00  0.00           H  
HETATM   23  H2  UNL     1      -5.797   1.894  -1.497  1.00  0.00           H  
HETATM   24  H3  UNL     1      -4.027   1.939  -1.583  1.00  0.00           H  
HETATM   25  H4  UNL     1      -6.677  -0.258   0.160  1.00  0.00           H  
HETATM   26  H5  UNL     1      -5.379  -1.078   1.057  1.00  0.00           H  
HETATM   27  H6  UNL     1      -5.668   0.739   1.237  1.00  0.00           H  
HETATM   28  H7  UNL     1      -6.181  -1.309  -1.496  1.00  0.00           H  
HETATM   29  H8  UNL     1      -4.527  -1.375  -2.178  1.00  0.00           H  
HETATM   30  H9  UNL     1      -5.652  -0.078  -2.652  1.00  0.00           H  
HETATM   31  H10 UNL     1      -2.793  -0.166  -1.213  1.00  0.00           H  
HETATM   32  H11 UNL     1      -3.470   0.297   1.700  1.00  0.00           H  
HETATM   33  H12 UNL     1      -2.897   1.586   0.624  1.00  0.00           H  
HETATM   34  H13 UNL     1      -1.357  -0.980   1.259  1.00  0.00           H  
HETATM   35  H14 UNL     1      -0.443   0.197   2.739  1.00  0.00           H  
HETATM   36  H15 UNL     1      -0.767   1.675  -0.162  1.00  0.00           H  
HETATM   37  H16 UNL     1      -0.854   0.073  -0.992  1.00  0.00           H  
HETATM   38  H17 UNL     1       0.021  -2.222  -0.041  1.00  0.00           H  
HETATM   39  H18 UNL     1       1.469  -4.142   0.188  1.00  0.00           H  
HETATM   40  H19 UNL     1       3.915  -3.809   0.597  1.00  0.00           H  
HETATM   41  H20 UNL     1       4.822  -1.558   0.771  1.00  0.00           H  
HETATM   42  H21 UNL     1       2.745   1.396   1.042  1.00  0.00           H  
HETATM   43  H22 UNL     1       4.884   1.841   1.692  1.00  0.00           H  
HETATM   44  H23 UNL     1       5.123   0.104   1.888  1.00  0.00           H  
HETATM   45  H24 UNL     1       6.518  -0.035   0.049  1.00  0.00           H  
HETATM   46  H25 UNL     1       6.510   1.752   0.139  1.00  0.00           H  
HETATM   47  H26 UNL     1       5.112  -0.079  -1.771  1.00  0.00           H  
HETATM   48  H27 UNL     1       5.499   1.721  -1.913  1.00  0.00           H  
HETATM   49  H28 UNL     1       3.477   2.347  -0.920  1.00  0.00           H  
HETATM   50  H29 UNL     1       3.017   0.744  -1.578  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3    4    5
CONECT    3   25   26   27
CONECT    4   28   29   30
CONECT    5    6   31
CONECT    6    7   32   33
CONECT    7    8    9   34
CONECT    8   35
CONECT    9   10   36   37
CONECT   10   11
CONECT   11   12   12   16
CONECT   12   13   38
CONECT   13   14   14   39
CONECT   14   15   40
CONECT   15   16   16   41
CONECT   16   17
CONECT   17   18   21   42
CONECT   18   19   43   44
CONECT   19   20   45   46
CONECT   20   21   47   48
CONECT   21   49   50
END

HMDB0015447
     RDKit          3D
Penbutolol
 50 51  0  0  0  0  0  0  0  0999 V2000
   -4.8793    1.6345   -0.9287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7646    0.1536   -0.6581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6464   -0.1269    0.5464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2949   -0.6771   -1.8028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3790   -0.1459   -0.3803 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8731    0.4778    0.7852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4410    0.0821    1.0627 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1067    0.7547    2.2581 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5646    0.5841   -0.0548 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7845    0.4037    0.1370 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5488   -0.7191    0.2492 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0544   -2.0053    0.1502 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8695   -3.1398    0.2687 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2223   -2.9747    0.4929 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7595   -1.7053    0.5975 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9333   -0.6312    0.4764 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4797    0.7434    0.5631 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8380    0.8584    1.1331 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8573    0.8623    0.0459 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0923    0.9111   -1.2586 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6871    1.2689   -0.8616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7964    2.1732    0.0318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7974    1.8943   -1.4966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0270    1.9391   -1.5825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6770   -0.2579    0.1595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3787   -1.0777    1.0567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6683    0.7386    1.2375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1810   -1.3088   -1.4965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5273   -1.3753   -2.1785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6524   -0.0781   -2.6521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7935   -0.1663   -1.2128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4699    0.2975    1.6996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8972    1.5864    0.6242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3569   -0.9803    1.2591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4434    0.1972    2.7395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7669    1.6750   -0.1618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8544    0.0734   -0.9923 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0215   -2.2221   -0.0409 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4692   -4.1419    0.1877 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9146   -3.8092    0.5968 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8217   -1.5579    0.7711 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7449    1.3960    1.0425 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8836    1.8411    1.6924 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1226    0.1042    1.8876 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5184   -0.0346    0.0493 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5104    1.7518    0.1386 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1117   -0.0791   -1.7709 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4985    1.7209   -1.9132 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4766    2.3469   -0.9200 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0170    0.7438   -1.5776 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  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 16 11  1  0
 21 17  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  0
  6 32  1  0
  6 33  1  0
  7 34  1  1
  8 35  1  0
  9 36  1  0
  9 37  1  0
 12 38  1  0
 13 39  1  0
 14 40  1  0
 15 41  1  0
 17 42  1  0
 18 43  1  0
 18 44  1  0
 19 45  1  0
 19 46  1  0
 20 47  1  0
 20 48  1  0
 21 49  1  0
 21 50  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Levatol	HMDB
Hoe-893D	HMDB
Penbutolol sulfate	HMDB
Betapressin	HMDB
Hoe893d	HMDB
Sulfate, penbutolol	HMDB
Hoe 893D	HMDB
Penbutolol sulfate (2:1)	HMDB

Chemical Formula

C₁₈H₂₉NO₂

Average Molecular Weight

291.4284

Monoisotopic Molecular Weight

291.219829177

IUPAC Name

(2S)-1-(tert-butylamino)-3-(2-cyclopentylphenoxy)propan-2-ol

Traditional Name

(2S)-1-(tert-butylamino)-3-(2-cyclopentylphenoxy)propan-2-ol

CAS Registry Number

36507-48-9

SMILES

CC(C)(C)NC[C@H](O)COC1=CC=CC=C1C1CCCC1

InChI Identifier

InChI=1S/C18H29NO2/c1-18(2,3)19-12-15(20)13-21-17-11-7-6-10-16(17)14-8-4-5-9-14/h6-7,10-11,14-15,19-20H,4-5,8-9,12-13H2,1-3H3/t15-/m0/s1

InChI Key

KQXKVJAGOJTNJS-HNNXBMFYSA-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

ethanolamines (CHEBI:7954 )

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

Extracellular (HMDB: HMDB0015447)
Membrane (HMDB: HMDB0015447)

Source

Exogenous

Exogenous (HMDB: HMDB0015447)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Penbutolol Action Pathway (PathBank: SMP0000305)

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	0.021 g/L	Not Available
LogP	4.15	HANSCH,C ET AL. (1995)

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.021 g/L	ALOGPS
logP	3.84	ALOGPS
logP	3.55	ChemAxon
logS	-4.1	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	7	ChemAxon
Refractivity	86.6 m³·mol⁻¹	ChemAxon
Polarizability	34.58 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	167.754	31661259
DarkChem	[M-H]-	165.89	31661259
DeepCCS	[M+H]+	169.285	30932474
DeepCCS	[M-H]-	166.927	30932474
DeepCCS	[M-2H]-	200.061	30932474
DeepCCS	[M+Na]+	175.378	30932474
AllCCS	[M+H]+	172.4	32859911
AllCCS	[M+H-H2O]+	169.3	32859911
AllCCS	[M+NH4]+	175.3	32859911
AllCCS	[M+Na]+	176.1	32859911
AllCCS	[M-H]-	176.0	32859911
AllCCS	[M+Na-2H]-	176.5	32859911
AllCCS	[M+HCOO]-	177.3	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.	5.0 minutes	32390414
Predicted by Siyang on May 30, 2022	12.3845 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.48 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	46.3 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2019.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	242.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	179.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	167.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	163.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	444.6 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	442.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	124.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1003.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	463.2 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	1249.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	301.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	337.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	247.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	137.1 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	8.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Penbutolol	CC(C)(C)NC[C@H](O)COC1=CC=CC=C1C1CCCC1	2747.1	Standard polar	33892256
Penbutolol	CC(C)(C)NC[C@H](O)COC1=CC=CC=C1C1CCCC1	2137.0	Standard non polar	33892256
Penbutolol	CC(C)(C)NC[C@H](O)COC1=CC=CC=C1C1CCCC1	2157.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Penbutolol,1TMS,isomer #1	CC(C)(C)NC[C@@H](COC1=CC=CC=C1C1CCCC1)O[Si](C)(C)C	2116.8	Semi standard non polar	33892256
Penbutolol,1TMS,isomer #2	CC(C)(C)N(C[C@H](O)COC1=CC=CC=C1C1CCCC1)[Si](C)(C)C	2301.2	Semi standard non polar	33892256
Penbutolol,2TMS,isomer #1	CC(C)(C)N(C[C@@H](COC1=CC=CC=C1C1CCCC1)O[Si](C)(C)C)[Si](C)(C)C	2347.0	Semi standard non polar	33892256
Penbutolol,2TMS,isomer #1	CC(C)(C)N(C[C@@H](COC1=CC=CC=C1C1CCCC1)O[Si](C)(C)C)[Si](C)(C)C	2443.1	Standard non polar	33892256
Penbutolol,2TMS,isomer #1	CC(C)(C)N(C[C@@H](COC1=CC=CC=C1C1CCCC1)O[Si](C)(C)C)[Si](C)(C)C	2590.0	Standard polar	33892256
Penbutolol,1TBDMS,isomer #1	CC(C)(C)NC[C@@H](COC1=CC=CC=C1C1CCCC1)O[Si](C)(C)C(C)(C)C	2331.2	Semi standard non polar	33892256
Penbutolol,1TBDMS,isomer #2	CC(C)(C)N(C[C@H](O)COC1=CC=CC=C1C1CCCC1)[Si](C)(C)C(C)(C)C	2555.6	Semi standard non polar	33892256
Penbutolol,2TBDMS,isomer #1	CC(C)(C)N(C[C@@H](COC1=CC=CC=C1C1CCCC1)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2818.2	Semi standard non polar	33892256
Penbutolol,2TBDMS,isomer #1	CC(C)(C)N(C[C@@H](COC1=CC=CC=C1C1CCCC1)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2891.4	Standard non polar	33892256
Penbutolol,2TBDMS,isomer #1	CC(C)(C)N(C[C@@H](COC1=CC=CC=C1C1CCCC1)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2785.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Penbutolol GC-MS (Non-derivatized) - 70eV, Positive	splash10-07jr-9670000000-a79fb91d287e7cfdc751	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Penbutolol GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9723000000-f4da418202c281b26d1c	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Penbutolol 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 - Penbutolol 10V, Positive-QTOF	splash10-0006-2290000000-ace7f5ff44fdb9b5b791	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Penbutolol 20V, Positive-QTOF	splash10-000i-9570000000-00b3838f0255ecd5c823	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Penbutolol 40V, Positive-QTOF	splash10-00dr-9200000000-cebecfe8b8e40ed053bd	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Penbutolol 10V, Negative-QTOF	splash10-01ox-1790000000-ca08d570c87a1a04dad1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Penbutolol 20V, Negative-QTOF	splash10-03di-1900000000-d9272a3fe0f9ad9dbffe	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Penbutolol 40V, Negative-QTOF	splash10-03xu-8900000000-2e9694efe38bd6f12d89	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Penbutolol 10V, Positive-QTOF	splash10-0006-2090000000-64af498c50d53a85c9da	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Penbutolol 20V, Positive-QTOF	splash10-00ko-3390000000-f73c88fee4aee3b02b3f	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Penbutolol 40V, Positive-QTOF	splash10-0a4i-9200000000-5d04f85a5d512559ca56	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Penbutolol 10V, Negative-QTOF	splash10-01ox-0790000000-19293d327932c94fb42c	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Penbutolol 20V, Negative-QTOF	splash10-03di-0910000000-b2fd879060ccb5ebf563	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Penbutolol 40V, Negative-QTOF	splash10-02tc-8900000000-992ab80beaa1f5031430	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Penbutolol 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 DB01359	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01359	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01359

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

34369

KEGG Compound ID

C07416

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Penbutolol

METLIN ID

Not Available

PubChem Compound

37464

PDB ID

Not Available

ChEBI ID

354975

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

Hjorth S: (-)-Penbutolol as a blocker of central 5-HT1A receptor-mediated responses. Eur J Pharmacol. 1992 Nov 3;222(1):121-7. [PubMed:1468487 ]
Martinez Jorda R, Aguirre C, Calvo R, Rodriguez-Sasiain JM, Erill S: Decrease in penbutolol central response as a cause of changes in its serum protein binding. J Pharm Pharmacol. 1990 Mar;42(3):164-6. [PubMed:1974610 ]
Frishman WH, Covey S: Penbutolol and carteolol: two new beta-adrenergic blockers with partial agonism. J Clin Pharmacol. 1990 May;30(5):412-21. [PubMed:2189902 ]
Pepe S, Scalici G, D'Angelo A, Curiale B, Corrao S, Agnello C: [Validity of the use of penbutolol in essential arterial hypertension]. Minerva Med. 1990 Jun;81(6):471-3. [PubMed:2359502 ]
Aguirre C, Rodriguez-Sasiain JM, Calvo R: Decrease in penbutolol protein binding as a consequence of treatment with some alkylating agents. Cancer Chemother Pharmacol. 1994;34(1):86-8. [PubMed:8174208 ]
Maurer HH, Tenberken O, Kratzsch C, Weber AA, Peters FT: Screening for library-assisted identification and fully validated quantification of 22 beta-blockers in blood plasma by liquid chromatography-mass spectrometry with atmospheric pressure chemical ionization. J Chromatogr A. 2004 Nov 26;1058(1-2):169-81. [PubMed:15595665 ]

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

Venter CP, Joubert PH: Ethnic differences in beta-1-adrenoceptor sensitivity. S Afr Med J. 1982 Nov 27;62(23):849-50. [PubMed:6755764 ]
Sanchez C: Effect of serotonergic drugs on footshock-induced ultrasonic vocalization in adult male rats. Behav Pharmacol. 1993 Jun;4(3):269-277. [PubMed:11224195 ]
Doze P, Elsinga PH, Maas B, Van Waarde A, Wegman T, Vaalburg W: Synthesis and evaluation of radiolabeled antagonists for imaging of beta-adrenoceptors in the brain with PET. Neurochem Int. 2002 Feb;40(2):145-55. [PubMed:11738481 ]

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

Kulkarni RD, DaSilva LM, Chabria NL, Chadha DR: Beta-2 adrenoceptor blocking activity of penbutolol and propranolol at very low doses. Clin Pharmacol Ther. 1977 Jun;21(6):685-90. [PubMed:16716 ]
Hjorth S, Sharp T: In vivo microdialysis evidence for central serotonin1A and serotonin1B autoreceptor blocking properties of the beta adrenoceptor antagonist (-)penbutolol. J Pharmacol Exp Ther. 1993 May;265(2):707-12. [PubMed:8098761 ]
Hjorth S, Bengtsson HJ, Milano S: Raphe 5-HT1A autoreceptors, but not postsynaptic 5-HT1A receptors or beta-adrenoceptors, restrain the citalopram-induced increase in extracellular 5-hydroxytryptamine in vivo. Eur J Pharmacol. 1996 Nov 28;316(1):43-7. [PubMed:8982649 ]
Sanchez C: Effect of serotonergic drugs on footshock-induced ultrasonic vocalization in adult male rats. Behav Pharmacol. 1993 Jun;4(3):269-277. [PubMed:11224195 ]
Ijzerman AP, Nagesser A, Garritsen A: The membrane stabilizing activity of beta-adrenoceptor ligands. Quantitative evaluation of the interaction of phenoxypropanolamines with the [3H]batrachotoxinin A 20-alpha-benzoate binding site on voltage-sensitive sodium channels in rat brain. Biochem Pharmacol. 1987 Dec 15;36(24):4239-44. [PubMed:2446632 ]

Showing metabocard for Penbutolol (HMDB0015447)

MOL for HMDB0015447 (Penbutolol)

3D MOL for HMDB0015447 (Penbutolol)

3D SDF for HMDB0015447 (Penbutolol)

3D-SDF for HMDB0015447 (Penbutolol)

PDB for HMDB0015447 (Penbutolol)

3D PDB for HMDB0015447 (Penbutolol)

SMILES for HMDB0015447 (Penbutolol)

INCHI for HMDB0015447 (Penbutolol)

Structure for HMDB0015447 (Penbutolol)

3D Structure for HMDB0015447 (Penbutolol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References