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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (5) Show 5 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 02:51:51 UTC

HMDB ID

HMDB0015095

Secondary Accession Numbers

HMDB15095

Metabolite Identification

Common Name

Pindolol

Description

Pindolol is only found in individuals that have used or taken this drug. It is a moderately lipophilic beta blocker (adrenergic beta-antagonists). It is non-cardioselective and has intrinsic sympathomimetic actions, but little membrane-stabilizing activity. (From Martindale, The Extra Pharmocopoeia, 30th ed, p638)Pindolol 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. By binding beta-2 receptors in the juxtaglomerular apparatus, Pindolol 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

HMDB0015095
     RDKit          3D
Pindolol
 38 39  0  0  0  0  0  0  0  0999 V2000
    3.5596    1.2209   -0.5255 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0252   -0.1666   -0.1873 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5390   -0.1093    0.0161 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3465   -0.7680    0.8583 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0304   -1.1659    0.8914 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8694   -0.2692    0.8992 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8257    0.6718    1.9403 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3119    0.2406   -0.3904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0299    0.5108   -0.3258 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1609   -0.1851   -0.1366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3350   -1.5284    0.0472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5915   -2.1113    0.2304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7260   -1.3373    0.2317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5812    0.0088    0.0491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5297    0.9901    0.0067 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9484    2.1855   -0.1949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5934    1.9434   -0.2818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3497    0.5787   -0.1299 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8984    1.5728    0.2982 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4203    1.9356   -0.6010 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0029    1.1660   -1.4798 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9041   -0.8233   -1.1177 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9175   -1.0859    0.3201 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9604    0.1576   -0.9782 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8237    0.6387    0.7583 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9222   -0.9812    1.7132 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9406   -1.8411    1.8393 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8497   -1.9718    0.0989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0257   -0.9804    1.2580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0419    1.1214    1.9479 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5919   -0.4271   -1.2579 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7990    1.2300   -0.6935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4839   -2.1725    0.0324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6587   -3.1730    0.3690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6950   -1.7890    0.3724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5546    0.8500    0.1114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4097    3.1744   -0.2806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8233    2.6894   -0.4435 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
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 10  1  0
 18 14  2  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  7 30  1  0
  8 31  1  0
  8 32  1  0
 11 33  1  0
 12 34  1  0
 13 35  1  0
 15 36  1  0
 16 37  1  0
 17 38  1  0
M  END

960
  Mrv0541 02231215082D          

 18 19  0  0  1  0            999 V2000
    4.5080   -0.4562    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.1938    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    2.0188    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0031   -2.7702    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.7813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    1.1938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    2.4313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.0437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -1.6938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -1.2813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    3.2563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    2.0188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -2.5188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0031   -1.4423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -1.6938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -2.9313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4846   -2.1063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -2.5188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  8  1  0  0  0  0
  1 10  1  0  0  0  0
  2  5  1  0  0  0  0
  3  6  1  0  0  0  0
  3  7  1  0  0  0  0
  4 13  1  0  0  0  0
  4 17  1  0  0  0  0
  5  6  1  0  0  0  0
  5  8  1  0  0  0  0
  7 11  1  0  0  0  0
  7 12  1  0  0  0  0
  9 10  1  0  0  0  0
  9 13  2  0  0  0  0
  9 14  1  0  0  0  0
 10 15  2  0  0  0  0
 13 16  1  0  0  0  0
 14 17  2  0  0  0  0
 15 18  1  0  0  0  0
 16 18  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015095

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)NCC(O)COC1=CC=CC2=C1C=CN2

> <INCHI_IDENTIFIER>
InChI=1S/C14H20N2O2/c1-10(2)16-8-11(17)9-18-14-5-3-4-13-12(14)6-7-15-13/h3-7,10-11,15-17H,8-9H2,1-2H3

> <INCHI_KEY>
JZQKKSLKJUAGIC-UHFFFAOYSA-N

> <FORMULA>
C14H20N2O2

> <MOLECULAR_WEIGHT>
248.3208

> <EXACT_MASS>
248.152477894

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
28.267063591268215

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-(1H-indol-4-yloxy)-3-[(propan-2-yl)amino]propan-2-ol

> <ALOGPS_LOGP>
2.17

> <JCHEM_LOGP>
1.6929811656666667

> <ALOGPS_LOGS>
-2.46

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
16.657561492295873

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.086726064454854

> <JCHEM_PKA_STRONGEST_BASIC>
9.666166355475218

> <JCHEM_POLAR_SURFACE_AREA>
57.28

> <JCHEM_REFRACTIVITY>
71.46200000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.61e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-(1H-indol-4-yloxy)-3-(isopropylamino)propan-2-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015095
     RDKit          3D
Pindolol
 38 39  0  0  0  0  0  0  0  0999 V2000
    3.5596    1.2209   -0.5255 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0252   -0.1666   -0.1873 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5390   -0.1093    0.0161 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3465   -0.7680    0.8583 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0304   -1.1659    0.8914 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8694   -0.2692    0.8992 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8257    0.6718    1.9403 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3119    0.2406   -0.3904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0299    0.5108   -0.3258 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1609   -0.1851   -0.1366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3350   -1.5284    0.0472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5915   -2.1113    0.2304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7260   -1.3373    0.2317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5812    0.0088    0.0491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5297    0.9901    0.0067 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9484    2.1855   -0.1949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5934    1.9434   -0.2818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3497    0.5787   -0.1299 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8984    1.5728    0.2982 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4203    1.9356   -0.6010 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0029    1.1660   -1.4798 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9041   -0.8233   -1.1177 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9175   -1.0859    0.3201 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9604    0.1576   -0.9782 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8237    0.6387    0.7583 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9222   -0.9812    1.7132 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9406   -1.8411    1.8393 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8497   -1.9718    0.0989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0257   -0.9804    1.2580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0419    1.1214    1.9479 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5919   -0.4271   -1.2579 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7990    1.2300   -0.6935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4839   -2.1725    0.0324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6587   -3.1730    0.3690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6950   -1.7890    0.3724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5546    0.8500    0.1114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4097    3.1744   -0.2806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8233    2.6894   -0.4435 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
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 10  1  0
 18 14  2  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  7 30  1  0
  8 31  1  0
  8 32  1  0
 11 33  1  0
 12 34  1  0
 13 35  1  0
 15 36  1  0
 16 37  1  0
 17 38  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 960                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       8.415  -0.852   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       8.415   2.228   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0       5.748   3.768   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0      11.206  -5.171   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       7.081   1.458   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.748   2.228   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.414   4.538   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.081  -0.082   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.748  -3.162   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.415  -2.392   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.414   6.078   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.080   3.768   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.748  -4.702   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.206  -2.692   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.081  -3.162   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.415  -5.472   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.105  -3.932   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.081  -4.702   0.000  0.00  0.00           C+0
CONECT    1    8   10                                                       
CONECT    2    5                                                            
CONECT    3    6    7                                                       
CONECT    4   13   17                                                       
CONECT    5    2    6    8                                                  
CONECT    6    3    5                                                       
CONECT    7    3   11   12                                                  
CONECT    8    1    5                                                       
CONECT    9   10   13   14                                                  
CONECT   10    1    9   15                                                  
CONECT   11    7                                                            
CONECT   12    7                                                            
CONECT   13    4    9   16                                                  
CONECT   14    9   17                                                       
CONECT   15   10   18                                                       
CONECT   16   13   18                                                       
CONECT   17    4   14                                                       
CONECT   18   15   16                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

COMPND    HMDB0243707
HETATM    1  C1  UNL     1      -4.013  -0.876   0.844  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.577   0.466   0.279  1.00  0.00           C  
HETATM    3  C3  UNL     1      -4.434   1.531   0.984  1.00  0.00           C  
HETATM    4  N1  UNL     1      -2.193   0.667   0.501  1.00  0.00           N  
HETATM    5  C4  UNL     1      -1.421   1.268  -0.526  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.167   0.413  -1.755  1.00  0.00           C  
HETATM    7  O1  UNL     1      -2.324   0.004  -2.350  1.00  0.00           O  
HETATM    8  C6  UNL     1      -0.199  -0.666  -1.365  1.00  0.00           C  
HETATM    9  O2  UNL     1       0.957  -0.006  -0.866  1.00  0.00           O  
HETATM   10  C7  UNL     1       2.067  -0.655  -0.371  1.00  0.00           C  
HETATM   11  C8  UNL     1       2.115  -2.031  -0.311  1.00  0.00           C  
HETATM   12  C9  UNL     1       3.236  -2.633   0.190  1.00  0.00           C  
HETATM   13  C10 UNL     1       4.312  -1.862   0.632  1.00  0.00           C  
HETATM   14  C11 UNL     1       4.262  -0.491   0.572  1.00  0.00           C  
HETATM   15  N2  UNL     1       5.127   0.482   0.920  1.00  0.00           N  
HETATM   16  C12 UNL     1       4.628   1.703   0.673  1.00  0.00           C  
HETATM   17  C13 UNL     1       3.376   1.487   0.136  1.00  0.00           C  
HETATM   18  C14 UNL     1       3.137   0.132   0.070  1.00  0.00           C  
HETATM   19  H1  UNL     1      -4.236  -0.825   1.936  1.00  0.00           H  
HETATM   20  H2  UNL     1      -3.174  -1.587   0.685  1.00  0.00           H  
HETATM   21  H3  UNL     1      -4.897  -1.251   0.288  1.00  0.00           H  
HETATM   22  H4  UNL     1      -3.903   0.508  -0.779  1.00  0.00           H  
HETATM   23  H5  UNL     1      -4.044   2.507   0.678  1.00  0.00           H  
HETATM   24  H6  UNL     1      -5.450   1.449   0.589  1.00  0.00           H  
HETATM   25  H7  UNL     1      -4.413   1.324   2.062  1.00  0.00           H  
HETATM   26  H8  UNL     1      -1.950   0.970   1.431  1.00  0.00           H  
HETATM   27  H9  UNL     1      -0.382   1.416  -0.076  1.00  0.00           H  
HETATM   28  H10 UNL     1      -1.718   2.315  -0.785  1.00  0.00           H  
HETATM   29  H11 UNL     1      -0.648   1.091  -2.481  1.00  0.00           H  
HETATM   30  H12 UNL     1      -2.135  -0.826  -2.848  1.00  0.00           H  
HETATM   31  H13 UNL     1       0.067  -1.311  -2.238  1.00  0.00           H  
HETATM   32  H14 UNL     1      -0.625  -1.315  -0.584  1.00  0.00           H  
HETATM   33  H15 UNL     1       1.239  -2.545  -0.662  1.00  0.00           H  
HETATM   34  H16 UNL     1       3.286  -3.718   0.247  1.00  0.00           H  
HETATM   35  H17 UNL     1       5.194  -2.342   1.023  1.00  0.00           H  
HETATM   36  H18 UNL     1       6.081   0.328   1.335  1.00  0.00           H  
HETATM   37  H19 UNL     1       5.154   2.655   0.867  1.00  0.00           H  
HETATM   38  H20 UNL     1       2.666   2.226  -0.197  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3    4   22
CONECT    3   23   24   25
CONECT    4    5   26
CONECT    5    6   27   28
CONECT    6    7    8   29
CONECT    7   30
CONECT    8    9   31   32
CONECT    9   10
CONECT   10   11   11   18
CONECT   11   12   33
CONECT   12   13   13   34
CONECT   13   14   35
CONECT   14   15   18   18
CONECT   15   16   36
CONECT   16   17   17   37
CONECT   17   18   38
END

HMDB0015095
     RDKit          3D
Pindolol
 38 39  0  0  0  0  0  0  0  0999 V2000
    3.5596    1.2209   -0.5255 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0252   -0.1666   -0.1873 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5390   -0.1093    0.0161 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3465   -0.7680    0.8583 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0304   -1.1659    0.8914 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8694   -0.2692    0.8992 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8257    0.6718    1.9403 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3119    0.2406   -0.3904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0299    0.5108   -0.3258 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1609   -0.1851   -0.1366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3350   -1.5284    0.0472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5915   -2.1113    0.2304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7260   -1.3373    0.2317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5812    0.0088    0.0491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5297    0.9901    0.0067 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9484    2.1855   -0.1949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5934    1.9434   -0.2818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3497    0.5787   -0.1299 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8984    1.5728    0.2982 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4203    1.9356   -0.6010 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0029    1.1660   -1.4798 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9041   -0.8233   -1.1177 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9175   -1.0859    0.3201 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9604    0.1576   -0.9782 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8237    0.6387    0.7583 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9222   -0.9812    1.7132 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9406   -1.8411    1.8393 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8497   -1.9718    0.0989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0257   -0.9804    1.2580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0419    1.1214    1.9479 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5919   -0.4271   -1.2579 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7990    1.2300   -0.6935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4839   -2.1725    0.0324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6587   -3.1730    0.3690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6950   -1.7890    0.3724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5546    0.8500    0.1114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4097    3.1744   -0.2806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8233    2.6894   -0.4435 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
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 10  1  0
 18 14  2  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  7 30  1  0
  8 31  1  0
  8 32  1  0
 11 33  1  0
 12 34  1  0
 13 35  1  0
 15 36  1  0
 16 37  1  0
 17 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-(1H-indol-4-Yloxy)-3-(isopropylamino)propan-2-ol	ChEBI
1-(1H-indol-4-Yloxy)-3-(propan-2-ylamino)-propan-2-ol	ChEBI
1-(1H-indol-4-Yloxy)-3-[(1-methylethyl)amino]propan-2-ol	ChEBI
4-(2-Hydroxy-3-isopropylaminopropoxy)-indole	ChEBI
Betapindol	ChEBI
Blockin L	ChEBI
Blocklin L	ChEBI
Blocklin-L	ChEBI
Calvisken	ChEBI
Cardilate	ChEBI
Carvisken	ChEBI
Decreten	ChEBI
Durapindol	ChEBI
Glauco-visken	ChEBI
Pectobloc	ChEBI
Pinbetol	ChEBI
Pindololum	ChEBI
Prinodolol	ChEBI
Pynastin	ChEBI
Visken	ChEBI
Cardilic acid	Generator
LB 46	HMDB
LB-46	HMDB
Prindolol	HMDB

Chemical Formula

C₁₄H₂₀N₂O₂

Average Molecular Weight

248.3208

Monoisotopic Molecular Weight

248.152477894

IUPAC Name

1-(1H-indol-4-yloxy)-3-[(propan-2-yl)amino]propan-2-ol

Traditional Name

1-(1H-indol-4-yloxy)-3-(isopropylamino)propan-2-ol

CAS Registry Number

13523-86-9

SMILES

CC(C)NCC(O)COC1=CC=CC2=C1C=CN2

InChI Identifier

InChI=1S/C14H20N2O2/c1-10(2)16-8-11(17)9-18-14-5-3-4-13-12(14)6-7-15-13/h3-7,10-11,15-17H,8-9H2,1-2H3

InChI Key

JZQKKSLKJUAGIC-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indoles. Indoles are compounds containing an indole moiety, which consists of pyrrole ring fused to benzene to form 2,3-benzopyrrole.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indoles

Direct Parent

Indoles

Alternative Parents

Substituents

Indole
Alkyl aryl ether
Benzenoid
Pyrrole
Heteroaromatic compound
Secondary alcohol
1,2-aminoalcohol
Azacycle
Secondary amine
Ether
Secondary aliphatic amine
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Amine
Organic nitrogen compound
Alcohol
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

indoles (CHEBI:8214 )
secondary amine (CHEBI:8214 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0015095)

Source

Exogenous

Exogenous (HMDB: HMDB0015095)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Pindolol Action Pathway (PathBank: SMP0000306)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	167 - 171 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.86 g/L	Not Available
LogP	1.9	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	159.1	30932474

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.86 g/L	ALOGPS
logP	2.17	ALOGPS
logP	1.69	ChemAxon
logS	-2.5	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	3	ChemAxon
Polar Surface Area	57.28 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	71.46 m³·mol⁻¹	ChemAxon
Polarizability	28.27 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]+	157.971	31661259
DarkChem	[M-H]-	153.651	31661259
DeepCCS	[M+H]+	155.752	30932474
DeepCCS	[M-H]-	153.394	30932474
DeepCCS	[M-2H]-	187.061	30932474
DeepCCS	[M+Na]+	162.34	30932474
AllCCS	[M+H]+	159.5	32859911
AllCCS	[M+H-H2O]+	156.0	32859911
AllCCS	[M+NH4]+	162.8	32859911
AllCCS	[M+Na]+	163.8	32859911
AllCCS	[M-H]-	162.4	32859911
AllCCS	[M+Na-2H]-	162.6	32859911
AllCCS	[M+HCOO]-	163.0	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.	3.08 minutes	32390414
Predicted by Siyang on May 30, 2022	10.358 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	4.06 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	88.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Pindolol	CC(C)NCC(O)COC1=CC=CC2=C1C=CN2	3303.0	Standard polar	33892256
Pindolol	CC(C)NCC(O)COC1=CC=CC2=C1C=CN2	2239.3	Standard non polar	33892256
Pindolol	CC(C)NCC(O)COC1=CC=CC2=C1C=CN2	2264.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Pindolol,1TMS,isomer #1	CC(C)NCC(COC1=CC=CC2=C1C=C[NH]2)O[Si](C)(C)C	2269.7	Semi standard non polar	33892256
Pindolol,1TMS,isomer #2	CC(C)N(CC(O)COC1=CC=CC2=C1C=C[NH]2)[Si](C)(C)C	2459.2	Semi standard non polar	33892256
Pindolol,1TMS,isomer #3	CC(C)NCC(O)COC1=CC=CC2=C1C=CN2[Si](C)(C)C	2348.0	Semi standard non polar	33892256
Pindolol,2TMS,isomer #1	CC(C)N(CC(COC1=CC=CC2=C1C=C[NH]2)O[Si](C)(C)C)[Si](C)(C)C	2482.1	Semi standard non polar	33892256
Pindolol,2TMS,isomer #1	CC(C)N(CC(COC1=CC=CC2=C1C=C[NH]2)O[Si](C)(C)C)[Si](C)(C)C	2447.9	Standard non polar	33892256
Pindolol,2TMS,isomer #1	CC(C)N(CC(COC1=CC=CC2=C1C=C[NH]2)O[Si](C)(C)C)[Si](C)(C)C	2782.4	Standard polar	33892256
Pindolol,2TMS,isomer #2	CC(C)NCC(COC1=CC=CC2=C1C=CN2[Si](C)(C)C)O[Si](C)(C)C	2334.6	Semi standard non polar	33892256
Pindolol,2TMS,isomer #2	CC(C)NCC(COC1=CC=CC2=C1C=CN2[Si](C)(C)C)O[Si](C)(C)C	2358.3	Standard non polar	33892256
Pindolol,2TMS,isomer #2	CC(C)NCC(COC1=CC=CC2=C1C=CN2[Si](C)(C)C)O[Si](C)(C)C	2674.0	Standard polar	33892256
Pindolol,2TMS,isomer #3	CC(C)N(CC(O)COC1=CC=CC2=C1C=CN2[Si](C)(C)C)[Si](C)(C)C	2499.6	Semi standard non polar	33892256
Pindolol,2TMS,isomer #3	CC(C)N(CC(O)COC1=CC=CC2=C1C=CN2[Si](C)(C)C)[Si](C)(C)C	2523.1	Standard non polar	33892256
Pindolol,2TMS,isomer #3	CC(C)N(CC(O)COC1=CC=CC2=C1C=CN2[Si](C)(C)C)[Si](C)(C)C	2800.3	Standard polar	33892256
Pindolol,3TMS,isomer #1	CC(C)N(CC(COC1=CC=CC2=C1C=CN2[Si](C)(C)C)O[Si](C)(C)C)[Si](C)(C)C	2557.5	Semi standard non polar	33892256
Pindolol,3TMS,isomer #1	CC(C)N(CC(COC1=CC=CC2=C1C=CN2[Si](C)(C)C)O[Si](C)(C)C)[Si](C)(C)C	2523.6	Standard non polar	33892256
Pindolol,3TMS,isomer #1	CC(C)N(CC(COC1=CC=CC2=C1C=CN2[Si](C)(C)C)O[Si](C)(C)C)[Si](C)(C)C	2626.3	Standard polar	33892256
Pindolol,1TBDMS,isomer #1	CC(C)NCC(COC1=CC=CC2=C1C=C[NH]2)O[Si](C)(C)C(C)(C)C	2504.8	Semi standard non polar	33892256
Pindolol,1TBDMS,isomer #2	CC(C)N(CC(O)COC1=CC=CC2=C1C=C[NH]2)[Si](C)(C)C(C)(C)C	2708.1	Semi standard non polar	33892256
Pindolol,1TBDMS,isomer #3	CC(C)NCC(O)COC1=CC=CC2=C1C=CN2[Si](C)(C)C(C)(C)C	2569.3	Semi standard non polar	33892256
Pindolol,2TBDMS,isomer #1	CC(C)N(CC(COC1=CC=CC2=C1C=C[NH]2)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2960.6	Semi standard non polar	33892256
Pindolol,2TBDMS,isomer #1	CC(C)N(CC(COC1=CC=CC2=C1C=C[NH]2)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2891.1	Standard non polar	33892256
Pindolol,2TBDMS,isomer #1	CC(C)N(CC(COC1=CC=CC2=C1C=C[NH]2)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2944.8	Standard polar	33892256
Pindolol,2TBDMS,isomer #2	CC(C)NCC(COC1=CC=CC2=C1C=CN2[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2753.8	Semi standard non polar	33892256
Pindolol,2TBDMS,isomer #2	CC(C)NCC(COC1=CC=CC2=C1C=CN2[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2773.5	Standard non polar	33892256
Pindolol,2TBDMS,isomer #2	CC(C)NCC(COC1=CC=CC2=C1C=CN2[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2841.7	Standard polar	33892256
Pindolol,2TBDMS,isomer #3	CC(C)N(CC(O)COC1=CC=CC2=C1C=CN2[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2935.5	Semi standard non polar	33892256
Pindolol,2TBDMS,isomer #3	CC(C)N(CC(O)COC1=CC=CC2=C1C=CN2[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2907.2	Standard non polar	33892256
Pindolol,2TBDMS,isomer #3	CC(C)N(CC(O)COC1=CC=CC2=C1C=CN2[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2949.4	Standard polar	33892256
Pindolol,3TBDMS,isomer #1	CC(C)N(CC(COC1=CC=CC2=C1C=CN2[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3170.6	Semi standard non polar	33892256
Pindolol,3TBDMS,isomer #1	CC(C)N(CC(COC1=CC=CC2=C1C=CN2[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3118.7	Standard non polar	33892256
Pindolol,3TBDMS,isomer #1	CC(C)N(CC(COC1=CC=CC2=C1C=CN2[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2871.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Pindolol GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-9810000000-7bc0638a69aba25ecb87	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pindolol GC-MS (1 TMS) - 70eV, Positive	splash10-0089-9600000000-8fd11cc5a2fed5384868	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pindolol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pindolol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pindolol GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pindolol GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pindolol GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pindolol GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pindolol GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pindolol LC-ESI-ITFT , positive-QTOF	splash10-01b9-2900000000-e773b852c7d4839b531d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pindolol LC-ESI-ITFT , positive-QTOF	splash10-01c3-1900000000-97bebf43acd96bd5cf5b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pindolol LC-ESI-ITFT , positive-QTOF	splash10-01ba-0920000000-9c68ad2e49235b630737	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pindolol LC-ESI-ITFT , positive-QTOF	splash10-01b9-0900000000-e0edd57b20d4dcecb440	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pindolol , positive-QTOF	splash10-0002-1690000000-c5bffa0f5938ebc6de4b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pindolol 50V, Positive-QTOF	splash10-015c-0900000000-7208a6ab59379bc60e74	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pindolol 55V, Positive-QTOF	splash10-01b9-0900000000-762d3fea483c879a01e1	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pindolol 55V, Positive-QTOF	splash10-01b9-2900000000-de1a6711be132a9bc406	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pindolol 30V, Positive-QTOF	splash10-007p-0900000000-c7b76abb87f901266e0c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pindolol 40V, Positive-QTOF	splash10-00l6-0900000000-8b95aec2199af320261b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pindolol 80V, Positive-QTOF	splash10-01c3-1900000000-97bebf43acd96bd5cf5b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pindolol 20V, Positive-QTOF	splash10-0002-0890000000-a3c20cc0c0efe2b51cfd	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pindolol 10V, Positive-QTOF	splash10-0002-0090000000-9425d68d4cc59a32a43c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pindolol 35V, Positive-QTOF	splash10-01ba-0920000000-7f7959d21664f3e06a2e	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pindolol 10V, Positive-QTOF	splash10-0002-1490000000-8f45ac285bc25d656996	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pindolol 20V, Positive-QTOF	splash10-00yi-7940000000-9107bd061a82704636c4	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pindolol 40V, Positive-QTOF	splash10-060r-9400000000-da4f9e474bae11b0421c	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pindolol 10V, Negative-QTOF	splash10-000t-1790000000-f688d386b1973d57f378	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pindolol 20V, Negative-QTOF	splash10-001i-0900000000-cdd2bc6227637ee1b1fa	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pindolol 40V, Negative-QTOF	splash10-001i-2900000000-5d0d9df543fddaa5d1b8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pindolol 10V, Positive-QTOF	splash10-0002-0090000000-29275e6bc02f599a2d5e	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pindolol 20V, Positive-QTOF	splash10-0002-4890000000-dae8e1ddd1e40cf91067	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pindolol 40V, Positive-QTOF	splash10-0ab9-9300000000-f3f457ae6618e846a110	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pindolol 10V, Negative-QTOF	splash10-0002-0940000000-e2efd23ab9a55ae84789	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pindolol 20V, Negative-QTOF	splash10-001i-3900000000-3f95741c34f2779419f4	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
Pindolol 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 DB00960	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00960	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00960

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4662

KEGG Compound ID

C07445

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Pindolol

METLIN ID

Not Available

PubChem Compound

4828

PDB ID

Not Available

ChEBI ID

8214

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)

Download (PDF)

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

Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Joseph SS, Lynham JA, Molenaar P, Grace AA, Colledge WH, Kaumann AJ: Intrinsic sympathomimetic activity of (-)-pindolol mediated through a (-)-propranolol-resistant site of the beta1-adrenoceptor in human atrium and recombinant receptors. Naunyn Schmiedebergs Arch Pharmacol. 2003 Dec;368(6):496-503. Epub 2003 Nov 8. [PubMed:14608456 ]
Doggrell SA: Effects of (+/-)- (+)- and (-)-metoprolol, (+/-)- (+)- and (-)-pindolol, (+/-)-mepindolol and (+/-)-bopindolol on the rat left atria and portal vein. Gen Pharmacol. 1991;22(6):1169-77. [PubMed:1687398 ]
Berendsen HH, Broekkamp CL, Van Delft AM: Antagonism of 8-OH-DPAT-induced behaviour in rats. Eur J Pharmacol. 1990 Oct 2;187(1):97-103. [PubMed:2148726 ]
Watkins DJ, Lawrence AJ, Lewis SJ, Jarrott B: Loss of [125I]-pindolol binding to beta-adrenoceptors on rat nodose ganglion after chronic isoprenaline treatment. J Auton Nerv Syst. 1996 Aug 27;60(1-2):12-6. [PubMed:8884690 ]
Brodde OE, Michel MC, Wang XL, Zerkowski HR: Chronic beta-adrenoceptor antagonist treatment modulates human cardiac and vascular beta-adrenoceptor density in a subtype-selective fashion. J Hypertens Suppl. 1988 Dec;6(4):S497-500. [PubMed:2907348 ]

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

Rubenstein LA, Zauhar RJ, Lanzara RG: Molecular dynamics of a biophysical model for beta2-adrenergic and G protein-coupled receptor activation. J Mol Graph Model. 2006 Dec;25(4):396-409. Epub 2006 Mar 30. [PubMed:16574446 ]
Dejgaard A, Liggett SB, Christensen NJ, Cryer PE, Hilsted J: Adrenergic receptors are a fallible index of adrenergic denervation hypersensitivity. Scand J Clin Lab Invest. 1991 Dec;51(8):659-66. [PubMed:1666931 ]
Wheeldon NM, Newnham DM, Fraser GC, McDevitt DG, Lipworth BJ: The effect of pindolol on creatine kinase is not due to beta 2-adrenoceptor partial agonist activity. Br J Clin Pharmacol. 1991 Jun;31(6):723-4. [PubMed:1678274 ]
Doggrell SA: Effects of (+/-)- (+)- and (-)-metoprolol, (+/-)- (+)- and (-)-pindolol, (+/-)-mepindolol and (+/-)-bopindolol on the rat left atria and portal vein. Gen Pharmacol. 1991;22(6):1169-77. [PubMed:1687398 ]
Doggrell SA: Relaxant and beta 2-adrenoceptor blocking activities of (+/- )-, (+)- and (-)-pindolol on the rat isolated aorta. J Pharm Pharmacol. 1990 Jun;42(6):444-6. [PubMed:1979630 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzyme Details

4. 5-hydroxytryptamine receptor 1B

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:: HTR1B
Uniprot ID:: P28222
Molecular weight:: 43567.5

References

Dawson LA, Nguyen HQ: The role of 5-HT(1A) and 5-HT(1B/1D) receptors on the modulation of acute fluoxetine-induced changes in extracellular 5-HT: the mechanism of action of (+/-)pindolol. Neuropharmacology. 2000 Apr 3;39(6):1044-52. [PubMed:10727715 ]
Ariani K, Hamblin MW, Tan GL, Stratford CA, Ciaranello RD: G protein dependent alterations in [125I]iodocyanopindolol and +/- cyanopindolol binding at 5-HT1B binding sites in rat brain membranes. Neurochem Res. 1989 Sep;14(9):835-43. [PubMed:2512511 ]
Leonhardt S, Herrick-Davis K, Titeler M: Detection of a novel serotonin receptor subtype (5-HT1E) in human brain: interaction with a GTP-binding protein. J Neurochem. 1989 Aug;53(2):465-71. [PubMed:2664084 ]
Herrick-Davis K, Titeler M, Leonhardt S, Struble R, Price D: Serotonin 5-HT1D receptors in human prefrontal cortex and caudate: interaction with a GTP binding protein. J Neurochem. 1988 Dec;51(6):1906-12. [PubMed:3141589 ]
Terron JA, Lopez-Munoz FJ, Hong E, Villalon CM: 2-(2-Aminoethyl)-quinoline (D-1997): a novel agonist at 5-hydroxytryptamine1-like receptors in the canine basilar artery. Arch Int Pharmacodyn Ther. 1994 Jan-Feb;327(1):56-68. [PubMed:7944828 ]

Enzyme Details

5. 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

Smeraldi E, Benedetti F, Barbini B, Campori E, Colombo C: Sustained antidepressant effect of sleep deprivation combined with pindolol in bipolar depression. A placebo-controlled trial. Neuropsychopharmacology. 1999 Apr;20(4):380-5. [PubMed:10088139 ]
Haddjeri N, de Montigny C, Blier P: Modulation of the firing activity of rat serotonin and noradrenaline neurons by (+/-)pindolol. Biol Psychiatry. 1999 May 1;45(9):1163-9. [PubMed:10331108 ]
Gobert A, Millan MJ: Modulation of dialysate levels of dopamine, noradrenaline, and serotonin (5-HT) in the frontal cortex of freely-moving rats by (-)-pindolol alone and in association with 5-HT reuptake inhibitors: comparative roles of beta-adrenergic, 5-HT1A, and 5-HT1B receptors. Neuropsychopharmacology. 1999 Aug;21(2):268-84. [PubMed:10432475 ]
Andree B, Thorberg SO, Halldin C, Farde L: Pindolol binding to 5-HT1A receptors in the human brain confirmed with positron emission tomography. Psychopharmacology (Berl). 1999 Jun;144(3):303-5. [PubMed:10435400 ]
Fornal CA, Martin FJ, Metzler CW, Jacobs BL: Pindolol suppresses serotonergic neuronal activity and does not block the inhibition of serotonergic neurons produced by 8-hydroxy-2-(di-n-propylamino)tetralin in awake cats. J Pharmacol Exp Ther. 1999 Oct;291(1):229-38. [PubMed:10490909 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Showing metabocard for Pindolol (HMDB0015095)

MOL for HMDB0015095 (Pindolol)

3D MOL for HMDB0015095 (Pindolol)

3D SDF for HMDB0015095 (Pindolol)

3D-SDF for HMDB0015095 (Pindolol)

PDB for HMDB0015095 (Pindolol)

3D PDB for HMDB0015095 (Pindolol)

SMILES for HMDB0015095 (Pindolol)

INCHI for HMDB0015095 (Pindolol)

Structure for HMDB0015095 (Pindolol)

3D Structure for HMDB0015095 (Pindolol)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

References

References