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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 15:16:52 UTC

Update Date

2022-03-07 02:52:05 UTC

HMDB ID

HMDB0015696

Secondary Accession Numbers

HMDB15696

Metabolite Identification

Common Name

Bopindolol

Description

Bopindolol is only found in individuals that have used or taken this drug. It is a beta blocker. It is an ester which acts as a prodrug for 'pindolol':http://drugbank.ca/drugs/DB00960. Bopindolol (as 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

44112
  Mrv0541 02241214202D          

 28 30  0  0  1  0            999 V2000
    5.2224    0.9875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -0.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    2.2251    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    0.5750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7176   -2.9764    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    1.4001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    1.7020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    0.2731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -1.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -1.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -2.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7176   -1.6486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1991   -2.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -1.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -3.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    1.8126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -2.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0241   -2.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    2.2251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    1.8126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    3.0501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659    2.2251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    3.4626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659    3.0501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  8  1  0  0  0  0
  1 20  1  0  0  0  0
  2 12  1  0  0  0  0
  2 14  1  0  0  0  0
  3 20  2  0  0  0  0
  4  6  1  0  0  0  0
  4  7  1  0  0  0  0
  5 15  1  0  0  0  0
  5 17  1  0  0  0  0
  6  9  1  0  0  0  0
  6 10  1  0  0  0  0
  6 11  1  0  0  0  0
  7  8  1  0  0  0  0
  8 12  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
 13 16  1  0  0  0  0
 14 18  2  0  0  0  0
 15 19  1  0  0  0  0
 16 17  2  0  0  0  0
 17 22  1  0  0  0  0
 18 21  1  0  0  0  0
 19 21  2  0  0  0  0
 20 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 24 26  1  0  0  0  0
 25 27  2  0  0  0  0
 26 28  2  0  0  0  0
 27 28  1  0  0  0  0
M  END

HMDB0015696
     RDKit          3D
Bopindolol
 56 58  0  0  0  0  0  0  0  0999 V2000
    5.9372    1.9454    2.0934 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2050    0.9568    1.2533 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8285    0.8155    1.1284 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5497   -0.2087    0.2583 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3826   -0.7666   -0.2201 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1483   -0.2992    0.1718 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0217   -0.8978   -0.3413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2658   -0.2268    0.2258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4950   -0.9255   -0.3387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4596   -2.2836    0.0883 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5538   -3.0905   -0.3612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8935   -2.6598    0.1275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2995   -4.5104    0.1530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6020   -3.2047   -1.8752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2143    1.1249   -0.1451 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1923    2.0983    0.8153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2178    1.8097    2.0604 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1387    3.5023    0.4447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1206    4.4927    1.4038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0694    5.8160    1.0595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0360    6.1346   -0.2793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0536    5.1615   -1.2328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1053    3.8186   -0.9078 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4427   -1.8132   -1.1085 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6564   -2.3107   -1.5257 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8253   -1.7450   -1.0409 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7846   -0.6896   -0.1452 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7583    0.0209    0.4612 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3017    2.1911    2.9568 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0777    2.8661    1.4755 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9012    1.5213    2.3911 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0956    1.4210    1.6407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0081   -0.7667   -1.4304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0735   -1.9584   -0.0142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2828   -0.3287    1.3239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3920   -0.8812   -1.4518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4209   -0.3876   -0.0959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1629   -2.4590    1.0517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5373   -3.5868    0.1754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4266   -1.9924   -0.5904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8989   -2.2613    1.1649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1360   -4.4172    1.2465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3519   -4.8323   -0.3050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1356   -5.1830   -0.1113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8433   -2.2486   -2.3714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6476   -3.6503   -2.1918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4051   -3.9391   -2.1171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1487    4.1991    2.4527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0552    6.6074    1.8151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9954    7.1771   -0.5473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0260    5.4612   -2.2785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1190    3.0430   -1.6663 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5566   -2.2861   -1.5134 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7695   -3.1266   -2.2175 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8049   -2.1095   -1.3459 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7800   -0.1374    0.3309 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 11 14  1  0
  8 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
  5 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28  2  1  0
 27  4  1  0
 23 18  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  3 32  1  0
  7 33  1  0
  7 34  1  0
  8 35  1  0
  9 36  1  0
  9 37  1  0
 10 38  1  0
 12 39  1  0
 12 40  1  0
 12 41  1  0
 13 42  1  0
 13 43  1  0
 13 44  1  0
 14 45  1  0
 14 46  1  0
 14 47  1  0
 19 48  1  0
 20 49  1  0
 21 50  1  0
 22 51  1  0
 23 52  1  0
 24 53  1  0
 25 54  1  0
 26 55  1  0
 28 56  1  0
M  END

44112
  Mrv0541 02241214202D          

 28 30  0  0  1  0            999 V2000
    5.2224    0.9875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -0.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    2.2251    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    0.5750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7176   -2.9764    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    1.4001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    1.7020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    0.2731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -1.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -1.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -2.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7176   -1.6486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1991   -2.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -1.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -3.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    1.8126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -2.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0241   -2.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    2.2251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    1.8126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    3.0501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659    2.2251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    3.4626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659    3.0501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  8  1  0  0  0  0
  1 20  1  0  0  0  0
  2 12  1  0  0  0  0
  2 14  1  0  0  0  0
  3 20  2  0  0  0  0
  4  6  1  0  0  0  0
  4  7  1  0  0  0  0
  5 15  1  0  0  0  0
  5 17  1  0  0  0  0
  6  9  1  0  0  0  0
  6 10  1  0  0  0  0
  6 11  1  0  0  0  0
  7  8  1  0  0  0  0
  8 12  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
 13 16  1  0  0  0  0
 14 18  2  0  0  0  0
 15 19  1  0  0  0  0
 16 17  2  0  0  0  0
 17 22  1  0  0  0  0
 18 21  1  0  0  0  0
 19 21  2  0  0  0  0
 20 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 24 26  1  0  0  0  0
 25 27  2  0  0  0  0
 26 28  2  0  0  0  0
 27 28  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015696

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=CC2=C(N1)C=CC=C2OCC(CNC(C)(C)C)OC(=O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C23H28N2O3/c1-16-13-19-20(25-16)11-8-12-21(19)27-15-18(14-24-23(2,3)4)28-22(26)17-9-6-5-7-10-17/h5-13,18,24-25H,14-15H2,1-4H3

> <INCHI_KEY>
UUOJIACWOAYWEZ-UHFFFAOYSA-N

> <FORMULA>
C23H28N2O3

> <MOLECULAR_WEIGHT>
380.48

> <EXACT_MASS>
380.209992772

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
43.08334286783953

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-(tert-butylamino)-3-[(2-methyl-1H-indol-4-yl)oxy]propan-2-yl benzoate

> <ALOGPS_LOGP>
4.45

> <JCHEM_LOGP>
4.668419005666666

> <ALOGPS_LOGS>
-5.38

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.797941540338005

> <JCHEM_PKA_STRONGEST_BASIC>
9.290179388621109

> <JCHEM_POLAR_SURFACE_AREA>
63.35

> <JCHEM_REFRACTIVITY>
111.0719

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.60e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
bopindolol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015696
     RDKit          3D
Bopindolol
 56 58  0  0  0  0  0  0  0  0999 V2000
    5.9372    1.9454    2.0934 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2050    0.9568    1.2533 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8285    0.8155    1.1284 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5497   -0.2087    0.2583 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3826   -0.7666   -0.2201 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1483   -0.2992    0.1718 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0217   -0.8978   -0.3413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2658   -0.2268    0.2258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4950   -0.9255   -0.3387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4596   -2.2836    0.0883 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5538   -3.0905   -0.3612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8935   -2.6598    0.1275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2995   -4.5104    0.1530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6020   -3.2047   -1.8752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2143    1.1249   -0.1451 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1923    2.0983    0.8153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2178    1.8097    2.0604 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1387    3.5023    0.4447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1206    4.4927    1.4038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0694    5.8160    1.0595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0360    6.1346   -0.2793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0536    5.1615   -1.2328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1053    3.8186   -0.9078 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4427   -1.8132   -1.1085 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6564   -2.3107   -1.5257 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8253   -1.7450   -1.0409 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7846   -0.6896   -0.1452 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7583    0.0209    0.4612 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3017    2.1911    2.9568 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0777    2.8661    1.4755 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9012    1.5213    2.3911 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0956    1.4210    1.6407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0081   -0.7667   -1.4304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0735   -1.9584   -0.0142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2828   -0.3287    1.3239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3920   -0.8812   -1.4518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4209   -0.3876   -0.0959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1629   -2.4590    1.0517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5373   -3.5868    0.1754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4266   -1.9924   -0.5904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8989   -2.2613    1.1649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1360   -4.4172    1.2465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3519   -4.8323   -0.3050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1356   -5.1830   -0.1113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8433   -2.2486   -2.3714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6476   -3.6503   -2.1918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4051   -3.9391   -2.1171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1487    4.1991    2.4527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0552    6.6074    1.8151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9954    7.1771   -0.5473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0260    5.4612   -2.2785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1190    3.0430   -1.6663 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5566   -2.2861   -1.5134 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7695   -3.1266   -2.2175 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8049   -2.1095   -1.3459 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7800   -0.1374    0.3309 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 11 14  1  0
  8 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
  5 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28  2  1  0
 27  4  1  0
 23 18  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  3 32  1  0
  7 33  1  0
  7 34  1  0
  8 35  1  0
  9 36  1  0
  9 37  1  0
 10 38  1  0
 12 39  1  0
 12 40  1  0
 12 41  1  0
 13 42  1  0
 13 43  1  0
 13 44  1  0
 14 45  1  0
 14 46  1  0
 14 47  1  0
 19 48  1  0
 20 49  1  0
 21 50  1  0
 22 51  1  0
 23 52  1  0
 24 53  1  0
 25 54  1  0
 26 55  1  0
 28 56  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 44112                                             
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0       9.748   1.843   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       9.748  -1.237   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       8.415   4.154   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       5.747   1.073   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0      12.540  -5.556   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       4.414   1.843   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.081   1.843   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.415   1.073   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.080   2.614   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.184   3.177   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.644   0.510   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.415  -0.467   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.082  -3.547   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.748  -2.777   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.082  -5.087   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.540  -3.077   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.438  -4.317   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.415  -3.547   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.748  -5.857   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.748   3.384   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.415  -5.087   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      14.978  -4.317   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      11.082   4.154   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      12.416   3.384   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      11.082   5.694   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      13.750   4.154   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      12.416   6.464   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      13.750   5.694   0.000  0.00  0.00           C+0
CONECT    1    8   20                                                       
CONECT    2   12   14                                                       
CONECT    3   20                                                            
CONECT    4    6    7                                                       
CONECT    5   15   17                                                       
CONECT    6    4    9   10   11                                             
CONECT    7    4    8                                                       
CONECT    8    1    7   12                                                  
CONECT    9    6                                                            
CONECT   10    6                                                            
CONECT   11    6                                                            
CONECT   12    2    8                                                       
CONECT   13   14   15   16                                                  
CONECT   14    2   13   18                                                  
CONECT   15    5   13   19                                                  
CONECT   16   13   17                                                       
CONECT   17    5   16   22                                                  
CONECT   18   14   21                                                       
CONECT   19   15   21                                                       
CONECT   20    1    3   23                                                  
CONECT   21   18   19                                                       
CONECT   22   17                                                            
CONECT   23   20   24   25                                                  
CONECT   24   23   26                                                       
CONECT   25   23   27                                                       
CONECT   26   24   28                                                       
CONECT   27   25   28                                                       
CONECT   28   26   27                                                       
MASTER        0    0    0    0    0    0    0    0   28    0   60    0
END

COMPND    HMDB0015696
HETATM    1  C1  UNL     1       5.937   1.945   2.093  1.00  0.00           C  
HETATM    2  C2  UNL     1       5.205   0.957   1.253  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.829   0.815   1.128  1.00  0.00           C  
HETATM    4  C4  UNL     1       3.550  -0.209   0.258  1.00  0.00           C  
HETATM    5  C5  UNL     1       2.383  -0.767  -0.220  1.00  0.00           C  
HETATM    6  O1  UNL     1       1.148  -0.299   0.172  1.00  0.00           O  
HETATM    7  C6  UNL     1      -0.022  -0.898  -0.341  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.266  -0.227   0.226  1.00  0.00           C  
HETATM    9  C8  UNL     1      -2.495  -0.926  -0.339  1.00  0.00           C  
HETATM   10  N1  UNL     1      -2.460  -2.284   0.088  1.00  0.00           N  
HETATM   11  C9  UNL     1      -3.554  -3.091  -0.361  1.00  0.00           C  
HETATM   12  C10 UNL     1      -4.894  -2.660   0.128  1.00  0.00           C  
HETATM   13  C11 UNL     1      -3.299  -4.510   0.153  1.00  0.00           C  
HETATM   14  C12 UNL     1      -3.602  -3.205  -1.875  1.00  0.00           C  
HETATM   15  O2  UNL     1      -1.214   1.125  -0.145  1.00  0.00           O  
HETATM   16  C13 UNL     1      -1.192   2.098   0.815  1.00  0.00           C  
HETATM   17  O3  UNL     1      -1.218   1.810   2.060  1.00  0.00           O  
HETATM   18  C14 UNL     1      -1.139   3.502   0.445  1.00  0.00           C  
HETATM   19  C15 UNL     1      -1.121   4.493   1.404  1.00  0.00           C  
HETATM   20  C16 UNL     1      -1.069   5.816   1.060  1.00  0.00           C  
HETATM   21  C17 UNL     1      -1.036   6.135  -0.279  1.00  0.00           C  
HETATM   22  C18 UNL     1      -1.054   5.161  -1.233  1.00  0.00           C  
HETATM   23  C19 UNL     1      -1.105   3.819  -0.908  1.00  0.00           C  
HETATM   24  C20 UNL     1       2.443  -1.813  -1.108  1.00  0.00           C  
HETATM   25  C21 UNL     1       3.656  -2.311  -1.526  1.00  0.00           C  
HETATM   26  C22 UNL     1       4.825  -1.745  -1.041  1.00  0.00           C  
HETATM   27  C23 UNL     1       4.785  -0.690  -0.145  1.00  0.00           C  
HETATM   28  N2  UNL     1       5.758   0.021   0.461  1.00  0.00           N  
HETATM   29  H1  UNL     1       5.302   2.191   2.957  1.00  0.00           H  
HETATM   30  H2  UNL     1       6.078   2.866   1.476  1.00  0.00           H  
HETATM   31  H3  UNL     1       6.901   1.521   2.391  1.00  0.00           H  
HETATM   32  H4  UNL     1       3.096   1.421   1.641  1.00  0.00           H  
HETATM   33  H5  UNL     1      -0.008  -0.767  -1.430  1.00  0.00           H  
HETATM   34  H6  UNL     1      -0.073  -1.958  -0.014  1.00  0.00           H  
HETATM   35  H7  UNL     1      -1.283  -0.329   1.324  1.00  0.00           H  
HETATM   36  H8  UNL     1      -2.392  -0.881  -1.452  1.00  0.00           H  
HETATM   37  H9  UNL     1      -3.421  -0.388  -0.096  1.00  0.00           H  
HETATM   38  H10 UNL     1      -2.163  -2.459   1.052  1.00  0.00           H  
HETATM   39  H11 UNL     1      -5.537  -3.587   0.175  1.00  0.00           H  
HETATM   40  H12 UNL     1      -5.427  -1.992  -0.590  1.00  0.00           H  
HETATM   41  H13 UNL     1      -4.899  -2.261   1.165  1.00  0.00           H  
HETATM   42  H14 UNL     1      -3.136  -4.417   1.247  1.00  0.00           H  
HETATM   43  H15 UNL     1      -2.352  -4.832  -0.305  1.00  0.00           H  
HETATM   44  H16 UNL     1      -4.136  -5.183  -0.111  1.00  0.00           H  
HETATM   45  H17 UNL     1      -3.843  -2.249  -2.371  1.00  0.00           H  
HETATM   46  H18 UNL     1      -2.648  -3.650  -2.192  1.00  0.00           H  
HETATM   47  H19 UNL     1      -4.405  -3.939  -2.117  1.00  0.00           H  
HETATM   48  H20 UNL     1      -1.149   4.199   2.453  1.00  0.00           H  
HETATM   49  H21 UNL     1      -1.055   6.607   1.815  1.00  0.00           H  
HETATM   50  H22 UNL     1      -0.995   7.177  -0.547  1.00  0.00           H  
HETATM   51  H23 UNL     1      -1.026   5.461  -2.279  1.00  0.00           H  
HETATM   52  H24 UNL     1      -1.119   3.043  -1.666  1.00  0.00           H  
HETATM   53  H25 UNL     1       1.557  -2.286  -1.513  1.00  0.00           H  
HETATM   54  H26 UNL     1       3.770  -3.127  -2.218  1.00  0.00           H  
HETATM   55  H27 UNL     1       5.805  -2.109  -1.346  1.00  0.00           H  
HETATM   56  H28 UNL     1       6.780  -0.137   0.331  1.00  0.00           H  
CONECT    1    2   29   30   31
CONECT    2    3    3   28
CONECT    3    4   32
CONECT    4    5    5   27
CONECT    5    6   24
CONECT    6    7
CONECT    7    8   33   34
CONECT    8    9   15   35
CONECT    9   10   36   37
CONECT   10   11   38
CONECT   11   12   13   14
CONECT   12   39   40   41
CONECT   13   42   43   44
CONECT   14   45   46   47
CONECT   15   16
CONECT   16   17   17   18
CONECT   18   19   19   23
CONECT   19   20   48
CONECT   20   21   21   49
CONECT   21   22   50
CONECT   22   23   23   51
CONECT   23   52
CONECT   24   25   25   53
CONECT   25   26   54
CONECT   26   27   27   55
CONECT   27   28
CONECT   28   56
END

HMDB0015696
     RDKit          3D
Bopindolol
 56 58  0  0  0  0  0  0  0  0999 V2000
    5.9372    1.9454    2.0934 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2050    0.9568    1.2533 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8285    0.8155    1.1284 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5497   -0.2087    0.2583 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3826   -0.7666   -0.2201 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1483   -0.2992    0.1718 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0217   -0.8978   -0.3413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2658   -0.2268    0.2258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4950   -0.9255   -0.3387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4596   -2.2836    0.0883 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5538   -3.0905   -0.3612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8935   -2.6598    0.1275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2995   -4.5104    0.1530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6020   -3.2047   -1.8752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2143    1.1249   -0.1451 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1923    2.0983    0.8153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2178    1.8097    2.0604 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1387    3.5023    0.4447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1206    4.4927    1.4038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0694    5.8160    1.0595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0360    6.1346   -0.2793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0536    5.1615   -1.2328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1053    3.8186   -0.9078 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4427   -1.8132   -1.1085 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6564   -2.3107   -1.5257 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8253   -1.7450   -1.0409 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7846   -0.6896   -0.1452 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7583    0.0209    0.4612 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3017    2.1911    2.9568 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0777    2.8661    1.4755 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9012    1.5213    2.3911 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0956    1.4210    1.6407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0081   -0.7667   -1.4304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0735   -1.9584   -0.0142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2828   -0.3287    1.3239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3920   -0.8812   -1.4518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4209   -0.3876   -0.0959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1629   -2.4590    1.0517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5373   -3.5868    0.1754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4266   -1.9924   -0.5904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8989   -2.2613    1.1649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1360   -4.4172    1.2465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3519   -4.8323   -0.3050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1356   -5.1830   -0.1113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8433   -2.2486   -2.3714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6476   -3.6503   -2.1918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4051   -3.9391   -2.1171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1487    4.1991    2.4527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0552    6.6074    1.8151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9954    7.1771   -0.5473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0260    5.4612   -2.2785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1190    3.0430   -1.6663 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5566   -2.2861   -1.5134 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7695   -3.1266   -2.2175 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8049   -2.1095   -1.3459 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7800   -0.1374    0.3309 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 11 14  1  0
  8 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
  5 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28  2  1  0
 27  4  1  0
 23 18  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  3 32  1  0
  7 33  1  0
  7 34  1  0
  8 35  1  0
  9 36  1  0
  9 37  1  0
 10 38  1  0
 12 39  1  0
 12 40  1  0
 12 41  1  0
 13 42  1  0
 13 43  1  0
 13 44  1  0
 14 45  1  0
 14 46  1  0
 14 47  1  0
 19 48  1  0
 20 49  1  0
 21 50  1  0
 22 51  1  0
 23 52  1  0
 24 53  1  0
 25 54  1  0
 26 55  1  0
 28 56  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Sandonorm	Kegg
1-(Tert-butylamino)-3-((2-methylindo)-4-yl)-2-propanol benzoate	HMDB
Bopindolol, (+-)-isomer	HMDB

Chemical Formula

C₂₃H₂₈N₂O₃

Average Molecular Weight

380.48

Monoisotopic Molecular Weight

380.209992772

IUPAC Name

1-(tert-butylamino)-3-[(2-methyl-1H-indol-4-yl)oxy]propan-2-yl benzoate

Traditional Name

bopindolol

CAS Registry Number

69010-88-4

SMILES

CC1=CC2=C(N1)C=CC=C2OCC(CNC(C)(C)C)OC(=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C23H28N2O3/c1-16-13-19-20(25-16)11-8-12-21(19)27-15-18(14-24-23(2,3)4)28-22(26)17-9-6-5-7-10-17/h5-13,18,24-25H,14-15H2,1-4H3

InChI Key

UUOJIACWOAYWEZ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Benzoic acid esters

Alternative Parents

Substituents

Benzoate ester
Indole
Indole or derivatives
Benzoyl
Alkyl aryl ether
Substituted pyrrole
Heteroaromatic compound
Pyrrole
Amino acid or derivatives
Carboxylic acid ester
Carboxylic acid derivative
Secondary aliphatic amine
Ether
Azacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Secondary amine
Amine
Hydrocarbon derivative
Organic oxygen compound
Organopnictogen compound
Organic oxide
Organonitrogen compound
Organooxygen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

indoles (CHEBI:76749 )

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: HMDB0015696)

Source

Exogenous

Exogenous (HMDB: HMDB0015696)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Bopindolol Action Pathway (PathBank: SMP0000657)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	152 - 153 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0016 g/L	ALOGPS
logP	4.45	ALOGPS
logP	4.67	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	16.8	ChemAxon
pKa (Strongest Basic)	9.29	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	63.35 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	111.07 m³·mol⁻¹	ChemAxon
Polarizability	43.08 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	189.259	31661259
DarkChem	[M-H]-	189.502	31661259
DeepCCS	[M+H]+	191.966	30932474
DeepCCS	[M-H]-	189.579	30932474
DeepCCS	[M-2H]-	223.905	30932474
DeepCCS	[M+Na]+	199.241	30932474
AllCCS	[M+H]+	194.7	32859911
AllCCS	[M+H-H2O]+	191.9	32859911
AllCCS	[M+NH4]+	197.2	32859911
AllCCS	[M+Na]+	197.9	32859911
AllCCS	[M-H]-	198.3	32859911
AllCCS	[M+Na-2H]-	198.2	32859911
AllCCS	[M+HCOO]-	198.2	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.	7.26 minutes	32390414
Predicted by Siyang on May 30, 2022	13.9871 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.15 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	39.2 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2707.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	285.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	187.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	176.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	186.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	560.6 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	450.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	67.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	925.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	540.6 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	1500.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	374.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	383.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	235.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	128.2 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	8.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Bopindolol	CC1=CC2=C(N1)C=CC=C2OCC(CNC(C)(C)C)OC(=O)C1=CC=CC=C1	4268.9	Standard polar	33892256
Bopindolol	CC1=CC2=C(N1)C=CC=C2OCC(CNC(C)(C)C)OC(=O)C1=CC=CC=C1	2998.6	Standard non polar	33892256
Bopindolol	CC1=CC2=C(N1)C=CC=C2OCC(CNC(C)(C)C)OC(=O)C1=CC=CC=C1	2978.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Bopindolol,1TMS,isomer #1	CC1=CC2=C(OCC(CNC(C)(C)C)OC(=O)C3=CC=CC=C3)C=CC=C2N1[Si](C)(C)C	3012.7	Semi standard non polar	33892256
Bopindolol,1TMS,isomer #1	CC1=CC2=C(OCC(CNC(C)(C)C)OC(=O)C3=CC=CC=C3)C=CC=C2N1[Si](C)(C)C	2894.0	Standard non polar	33892256
Bopindolol,1TMS,isomer #1	CC1=CC2=C(OCC(CNC(C)(C)C)OC(=O)C3=CC=CC=C3)C=CC=C2N1[Si](C)(C)C	3646.1	Standard polar	33892256
Bopindolol,1TMS,isomer #2	CC1=CC2=C(OCC(CN(C(C)(C)C)[Si](C)(C)C)OC(=O)C3=CC=CC=C3)C=CC=C2[NH]1	3176.2	Semi standard non polar	33892256
Bopindolol,1TMS,isomer #2	CC1=CC2=C(OCC(CN(C(C)(C)C)[Si](C)(C)C)OC(=O)C3=CC=CC=C3)C=CC=C2[NH]1	3118.4	Standard non polar	33892256
Bopindolol,1TMS,isomer #2	CC1=CC2=C(OCC(CN(C(C)(C)C)[Si](C)(C)C)OC(=O)C3=CC=CC=C3)C=CC=C2[NH]1	3828.2	Standard polar	33892256
Bopindolol,2TMS,isomer #1	CC1=CC2=C(OCC(CN(C(C)(C)C)[Si](C)(C)C)OC(=O)C3=CC=CC=C3)C=CC=C2N1[Si](C)(C)C	3192.6	Semi standard non polar	33892256
Bopindolol,2TMS,isomer #1	CC1=CC2=C(OCC(CN(C(C)(C)C)[Si](C)(C)C)OC(=O)C3=CC=CC=C3)C=CC=C2N1[Si](C)(C)C	3051.6	Standard non polar	33892256
Bopindolol,2TMS,isomer #1	CC1=CC2=C(OCC(CN(C(C)(C)C)[Si](C)(C)C)OC(=O)C3=CC=CC=C3)C=CC=C2N1[Si](C)(C)C	3547.9	Standard polar	33892256
Bopindolol,1TBDMS,isomer #1	CC1=CC2=C(OCC(CNC(C)(C)C)OC(=O)C3=CC=CC=C3)C=CC=C2N1[Si](C)(C)C(C)(C)C	3190.3	Semi standard non polar	33892256
Bopindolol,1TBDMS,isomer #1	CC1=CC2=C(OCC(CNC(C)(C)C)OC(=O)C3=CC=CC=C3)C=CC=C2N1[Si](C)(C)C(C)(C)C	3120.4	Standard non polar	33892256
Bopindolol,1TBDMS,isomer #1	CC1=CC2=C(OCC(CNC(C)(C)C)OC(=O)C3=CC=CC=C3)C=CC=C2N1[Si](C)(C)C(C)(C)C	3690.0	Standard polar	33892256
Bopindolol,1TBDMS,isomer #2	CC1=CC2=C(OCC(CN(C(C)(C)C)[Si](C)(C)C(C)(C)C)OC(=O)C3=CC=CC=C3)C=CC=C2[NH]1	3432.3	Semi standard non polar	33892256
Bopindolol,1TBDMS,isomer #2	CC1=CC2=C(OCC(CN(C(C)(C)C)[Si](C)(C)C(C)(C)C)OC(=O)C3=CC=CC=C3)C=CC=C2[NH]1	3294.8	Standard non polar	33892256
Bopindolol,1TBDMS,isomer #2	CC1=CC2=C(OCC(CN(C(C)(C)C)[Si](C)(C)C(C)(C)C)OC(=O)C3=CC=CC=C3)C=CC=C2[NH]1	3839.6	Standard polar	33892256
Bopindolol,2TBDMS,isomer #1	CC1=CC2=C(OCC(CN(C(C)(C)C)[Si](C)(C)C(C)(C)C)OC(=O)C3=CC=CC=C3)C=CC=C2N1[Si](C)(C)C(C)(C)C	3605.8	Semi standard non polar	33892256
Bopindolol,2TBDMS,isomer #1	CC1=CC2=C(OCC(CN(C(C)(C)C)[Si](C)(C)C(C)(C)C)OC(=O)C3=CC=CC=C3)C=CC=C2N1[Si](C)(C)C(C)(C)C	3432.5	Standard non polar	33892256
Bopindolol,2TBDMS,isomer #1	CC1=CC2=C(OCC(CN(C(C)(C)C)[Si](C)(C)C(C)(C)C)OC(=O)C3=CC=CC=C3)C=CC=C2N1[Si](C)(C)C(C)(C)C	3641.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Bopindolol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-7911000000-408594fb00778767ea81	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bopindolol 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 - Bopindolol 10V, Positive-QTOF	splash10-053r-0659000000-0b5a95ba7db5f64b371e	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bopindolol 20V, Positive-QTOF	splash10-0a59-3943000000-057c41afa69ae73f20ef	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bopindolol 40V, Positive-QTOF	splash10-0a59-3900000000-dfe073c414f0adca5ffe	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bopindolol 10V, Negative-QTOF	splash10-00ba-2926000000-db6f18d6a7284c3cb754	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bopindolol 20V, Negative-QTOF	splash10-0002-1900000000-058c780f09bbe5de8612	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bopindolol 40V, Negative-QTOF	splash10-000t-1900000000-e499cd0c6a8423dc66a5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bopindolol 10V, Positive-QTOF	splash10-001i-0239000000-262fbf226d3c984088f5	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bopindolol 20V, Positive-QTOF	splash10-0zi0-2894000000-cdb9d72cc2695ceff72c	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bopindolol 40V, Positive-QTOF	splash10-0a4i-5900000000-b1d6ff0f3bc22ddb8af9	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bopindolol 10V, Negative-QTOF	splash10-004i-0319000000-3a4a7e375a97ecf4e5ab	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bopindolol 20V, Negative-QTOF	splash10-03mi-1920000000-d0f867cab949edc4db68	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bopindolol 40V, Negative-QTOF	splash10-004i-9700000000-d0de49d04fe8b4c83f4c	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
Bopindolol 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 DB08807	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB08807	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB08807

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

40146

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Bopindolol

METLIN ID

Not Available

PubChem Compound

44112

PDB ID

Not Available

ChEBI ID

143782

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. Beta-1 adrenergic receptor

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

References

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

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

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

3. 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

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

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 ]

Enzyme Details

5. Beta-3 adrenergic receptor

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

References

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 Bopindolol (HMDB0015696)

MOL for HMDB0015696 (Bopindolol)

3D MOL for HMDB0015696 (Bopindolol)

3D SDF for HMDB0015696 (Bopindolol)

3D-SDF for HMDB0015696 (Bopindolol)

PDB for HMDB0015696 (Bopindolol)

3D PDB for HMDB0015696 (Bopindolol)

SMILES for HMDB0015696 (Bopindolol)

INCHI for HMDB0015696 (Bopindolol)

Structure for HMDB0015696 (Bopindolol)

3D Structure for HMDB0015696 (Bopindolol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

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