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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2022-03-07 02:51:44 UTC

HMDB ID

HMDB0014750

Secondary Accession Numbers

HMDB14750

Metabolite Identification

Common Name

Bisoprolol

Description

Bisoprolol is a cardioselective β1-adrenergic blocking agent used for secondary prevention of myocardial infarction (MI), heart failure, angina pectoris and mild to moderate hypertension. Bisoprolol is structurally similar to metoprolol, acebutolol and atenolol in that it has two substituents in the para position of the benzene ring. The β1-selectivity of these agents is thought to be due in part to the large substituents in the para position. At lower doses (less than 20 mg daily), bisoprolol selectively blocks cardiac β1-adrenergic receptors with little activity against β2-adrenergic receptors of the lungs and vascular smooth muscle. Receptor selectivity decreases with daily doses of 20 mg or greater. Unlike propranolol and pindolol, bisoprolol does not exhibit membrane-stabilizing or sympathomimetic activity. Bisoprolol possesses a single chiral centre and is administered as a racemic mixture. Only l-bisoprolol exhibits significant β-blocking activity.

Structure

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

HMDB0257069
     RDKit          3D
r-(+)-bisoprolol
 54 54  0  0  0  0  0  0  0  0999 V2000
    7.0369   -1.1437    0.0093 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6089    0.0136   -0.8962 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9326    0.3250   -1.6715 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2952    1.1770   -0.2118 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2911    1.3505    0.7094 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8524    1.3989    0.3176 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1506    1.5975    1.5352 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2979    0.2087   -0.3751 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9933    0.2052   -0.6646 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7483    0.2015   -0.1994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2780    0.2388   -1.1677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5835    0.2347   -0.7655 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9676    0.1956    0.5514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3698    0.1943    1.0007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9827   -1.0562    0.9642 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1259   -1.6180   -0.2604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0654   -0.9870   -1.2258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3792   -0.9272   -0.9006 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8340   -0.2994    0.1984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6402   -1.3204    1.0231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8223    0.8043   -0.2753 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9602    0.1579    1.5122 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3547    0.1617    1.1150 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6447   -0.6677    0.8109 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6020   -1.8424   -0.6353 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2044   -1.6785    0.4544 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9566   -0.3794   -1.6824 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5833    0.8495   -0.9436 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3132   -0.6342   -2.0210 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6260    0.9619   -2.5265 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1319    1.7955   -0.0743 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4825    2.3404    1.2528 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3239    0.6279    1.5862 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6419    2.2896   -0.3519 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5695    0.9554    2.1776 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8459    0.1194   -1.3874 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5671   -0.7417    0.1982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0347    0.2684   -2.2160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3916    0.2675   -1.5074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4154    0.5337    2.0538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9356    0.9572    0.4212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1502   -1.8671   -0.7715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5531   -2.6561   -0.0679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0057   -1.5572   -2.2057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7567    0.0622   -1.4983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1201    0.1660    0.8665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5792   -1.5836    0.4690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9902   -2.1784    1.2159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9029   -0.8539    2.0059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3073    1.3023   -1.1198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0005    1.5126    0.5751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7282    0.2804   -0.6078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2654    0.1267    2.5642 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0908    0.1103    1.8899 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  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 13 22  1  0
 22 23  2  0
 23 10  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  3 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  6 34  1  0
  7 35  1  0
  8 36  1  0
  8 37  1  0
 11 38  1  0
 12 39  1  0
 14 40  1  0
 14 41  1  0
 16 42  1  0
 16 43  1  0
 17 44  1  0
 17 45  1  0
 19 46  1  0
 20 47  1  0
 20 48  1  0
 20 49  1  0
 21 50  1  0
 21 51  1  0
 21 52  1  0
 22 53  1  0
 23 54  1  0
M  END

612
  Mrv0541 02231214482D          

 23 23  0  0  1  0            999 V2000
    4.5080    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    3.3001    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -4.1251    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    4.1251    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    3.3001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    2.8876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    4.5376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659    4.1251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    5.3626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -4.5376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -2.8876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -3.3001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -5.3626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -4.1251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  9  1  0  0  0  0
  1 12  1  0  0  0  0
  2  7  1  0  0  0  0
  3 14  1  0  0  0  0
  3 18  1  0  0  0  0
  4 15  1  0  0  0  0
  4 19  1  0  0  0  0
  5  6  1  0  0  0  0
  5  8  1  0  0  0  0
  6  7  1  0  0  0  0
  7  9  1  0  0  0  0
  8 10  1  0  0  0  0
  8 11  1  0  0  0  0
 12 16  2  0  0  0  0
 12 17  1  0  0  0  0
 13 14  1  0  0  0  0
 13 20  2  0  0  0  0
 13 21  1  0  0  0  0
 15 22  1  0  0  0  0
 15 23  1  0  0  0  0
 16 20  1  0  0  0  0
 17 21  2  0  0  0  0
 18 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014750

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)NCC(O)COC1=CC=C(COCCOC(C)C)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C18H31NO4/c1-14(2)19-11-17(20)13-23-18-7-5-16(6-8-18)12-21-9-10-22-15(3)4/h5-8,14-15,17,19-20H,9-13H2,1-4H3

> <INCHI_KEY>
VHYCDWMUTMEGQY-UHFFFAOYSA-N

> <FORMULA>
C18H31NO4

> <MOLECULAR_WEIGHT>
325.443

> <EXACT_MASS>
325.225308485

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
38.49740221234476

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-[(propan-2-yl)amino]-3-(4-{[2-(propan-2-yloxy)ethoxy]methyl}phenoxy)propan-2-ol

> <ALOGPS_LOGP>
2.30

> <JCHEM_LOGP>
2.1964033799999996

> <ALOGPS_LOGS>
-3.66

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.087971415762247

> <JCHEM_PKA_STRONGEST_BASIC>
9.666166605708403

> <JCHEM_POLAR_SURFACE_AREA>
59.95

> <JCHEM_REFRACTIVITY>
92.15350000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.07e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-{4-[(2-isopropoxyethoxy)methyl]phenoxy}-3-(isopropylamino)propan-2-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0257069
     RDKit          3D
r-(+)-bisoprolol
 54 54  0  0  0  0  0  0  0  0999 V2000
    7.0369   -1.1437    0.0093 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6089    0.0136   -0.8962 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9326    0.3250   -1.6715 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2952    1.1770   -0.2118 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2911    1.3505    0.7094 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8524    1.3989    0.3176 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1506    1.5975    1.5352 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2979    0.2087   -0.3751 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9933    0.2052   -0.6646 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7483    0.2015   -0.1994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2780    0.2388   -1.1677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5835    0.2347   -0.7655 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9676    0.1956    0.5514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3698    0.1943    1.0007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9827   -1.0562    0.9642 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1259   -1.6180   -0.2604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0654   -0.9870   -1.2258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3792   -0.9272   -0.9006 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8340   -0.2994    0.1984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6402   -1.3204    1.0231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8223    0.8043   -0.2753 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9602    0.1579    1.5122 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3547    0.1617    1.1150 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6447   -0.6677    0.8109 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6020   -1.8424   -0.6353 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2044   -1.6785    0.4544 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9566   -0.3794   -1.6824 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5833    0.8495   -0.9436 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3132   -0.6342   -2.0210 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6260    0.9619   -2.5265 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1319    1.7955   -0.0743 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4825    2.3404    1.2528 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3239    0.6279    1.5862 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6419    2.2896   -0.3519 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5695    0.9554    2.1776 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8459    0.1194   -1.3874 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5671   -0.7417    0.1982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0347    0.2684   -2.2160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3916    0.2675   -1.5074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4154    0.5337    2.0538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9356    0.9572    0.4212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1502   -1.8671   -0.7715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5531   -2.6561   -0.0679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0057   -1.5572   -2.2057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7567    0.0622   -1.4983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1201    0.1660    0.8665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5792   -1.5836    0.4690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9902   -2.1784    1.2159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9029   -0.8539    2.0059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3073    1.3023   -1.1198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0005    1.5126    0.5751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7282    0.2804   -0.6078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2654    0.1267    2.5642 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0908    0.1103    1.8899 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  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 13 22  1  0
 22 23  2  0
 23 10  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  3 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  6 34  1  0
  7 35  1  0
  8 36  1  0
  8 37  1  0
 11 38  1  0
 12 39  1  0
 14 40  1  0
 14 41  1  0
 16 42  1  0
 16 43  1  0
 17 44  1  0
 17 45  1  0
 19 46  1  0
 20 47  1  0
 20 48  1  0
 20 49  1  0
 21 50  1  0
 21 51  1  0
 21 52  1  0
 22 53  1  0
 23 54  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 612                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       8.415   3.080   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       8.415   6.160   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       7.081  -3.850   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       5.748  -7.700   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0      11.082   7.700   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      11.082   6.160   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.748   5.390   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.416   8.470   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.748   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.750   7.700   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.416  10.010   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.415   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.415  -1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.415  -3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.414  -8.470   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.081   0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.748   0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.081  -5.390   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.748  -6.160   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.081  -0.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.748  -0.770   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.414 -10.010   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.080  -7.700   0.000  0.00  0.00           C+0
CONECT    1    9   12                                                       
CONECT    2    7                                                            
CONECT    3   14   18                                                       
CONECT    4   15   19                                                       
CONECT    5    6    8                                                       
CONECT    6    5    7                                                       
CONECT    7    2    6    9                                                  
CONECT    8    5   10   11                                                  
CONECT    9    1    7                                                       
CONECT   10    8                                                            
CONECT   11    8                                                            
CONECT   12    1   16   17                                                  
CONECT   13   14   20   21                                                  
CONECT   14    3   13                                                       
CONECT   15    4   22   23                                                  
CONECT   16   12   20                                                       
CONECT   17   12   21                                                       
CONECT   18    3   19                                                       
CONECT   19    4   18                                                       
CONECT   20   13   16                                                       
CONECT   21   13   17                                                       
CONECT   22   15                                                            
CONECT   23   15                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   46    0
END

COMPND    HMDB0014750
HETATM    1  C1  UNL     1       7.275   1.176   0.452  1.00  0.00           C  
HETATM    2  C2  UNL     1       6.041   0.309   0.600  1.00  0.00           C  
HETATM    3  C3  UNL     1       6.543  -0.958   1.328  1.00  0.00           C  
HETATM    4  N1  UNL     1       5.042   0.871   1.423  1.00  0.00           N  
HETATM    5  C4  UNL     1       4.442   2.091   1.044  1.00  0.00           C  
HETATM    6  C5  UNL     1       3.591   1.929  -0.185  1.00  0.00           C  
HETATM    7  O1  UNL     1       4.299   1.499  -1.278  1.00  0.00           O  
HETATM    8  C6  UNL     1       2.508   0.892   0.142  1.00  0.00           C  
HETATM    9  O2  UNL     1       1.694   0.800  -1.008  1.00  0.00           O  
HETATM   10  C7  UNL     1       0.612  -0.071  -1.017  1.00  0.00           C  
HETATM   11  C8  UNL     1       0.352  -0.833   0.110  1.00  0.00           C  
HETATM   12  C9  UNL     1      -0.697  -1.708   0.160  1.00  0.00           C  
HETATM   13  C10 UNL     1      -1.534  -1.857  -0.927  1.00  0.00           C  
HETATM   14  C11 UNL     1      -2.681  -2.792  -0.924  1.00  0.00           C  
HETATM   15  O3  UNL     1      -3.256  -3.000   0.298  1.00  0.00           O  
HETATM   16  C12 UNL     1      -3.779  -1.863   0.885  1.00  0.00           C  
HETATM   17  C13 UNL     1      -4.859  -1.214   0.059  1.00  0.00           C  
HETATM   18  O4  UNL     1      -5.300  -0.092   0.753  1.00  0.00           O  
HETATM   19  C14 UNL     1      -6.297   0.519   0.011  1.00  0.00           C  
HETATM   20  C15 UNL     1      -7.596   0.580   0.823  1.00  0.00           C  
HETATM   21  C16 UNL     1      -5.916   1.933  -0.386  1.00  0.00           C  
HETATM   22  C17 UNL     1      -1.268  -1.103  -2.029  1.00  0.00           C  
HETATM   23  C18 UNL     1      -0.217  -0.221  -2.088  1.00  0.00           C  
HETATM   24  H1  UNL     1       8.094   0.504   0.107  1.00  0.00           H  
HETATM   25  H2  UNL     1       7.145   1.925  -0.373  1.00  0.00           H  
HETATM   26  H3  UNL     1       7.593   1.623   1.392  1.00  0.00           H  
HETATM   27  H4  UNL     1       5.747  -0.026  -0.396  1.00  0.00           H  
HETATM   28  H5  UNL     1       5.741  -1.703   1.324  1.00  0.00           H  
HETATM   29  H6  UNL     1       6.718  -0.645   2.377  1.00  0.00           H  
HETATM   30  H7  UNL     1       7.487  -1.304   0.864  1.00  0.00           H  
HETATM   31  H8  UNL     1       4.386   0.151   1.757  1.00  0.00           H  
HETATM   32  H9  UNL     1       3.717   2.369   1.868  1.00  0.00           H  
HETATM   33  H10 UNL     1       5.147   2.946   0.961  1.00  0.00           H  
HETATM   34  H11 UNL     1       3.071   2.904  -0.403  1.00  0.00           H  
HETATM   35  H12 UNL     1       3.816   0.847  -1.843  1.00  0.00           H  
HETATM   36  H13 UNL     1       1.961   1.219   1.043  1.00  0.00           H  
HETATM   37  H14 UNL     1       2.978  -0.102   0.317  1.00  0.00           H  
HETATM   38  H15 UNL     1       1.012  -0.711   0.959  1.00  0.00           H  
HETATM   39  H16 UNL     1      -0.870  -2.282   1.046  1.00  0.00           H  
HETATM   40  H17 UNL     1      -3.383  -2.502  -1.724  1.00  0.00           H  
HETATM   41  H18 UNL     1      -2.253  -3.787  -1.248  1.00  0.00           H  
HETATM   42  H19 UNL     1      -4.237  -2.160   1.850  1.00  0.00           H  
HETATM   43  H20 UNL     1      -2.976  -1.144   1.099  1.00  0.00           H  
HETATM   44  H21 UNL     1      -4.471  -0.852  -0.917  1.00  0.00           H  
HETATM   45  H22 UNL     1      -5.718  -1.896  -0.036  1.00  0.00           H  
HETATM   46  H23 UNL     1      -6.453  -0.059  -0.914  1.00  0.00           H  
HETATM   47  H24 UNL     1      -8.456   0.518   0.132  1.00  0.00           H  
HETATM   48  H25 UNL     1      -7.665   1.491   1.432  1.00  0.00           H  
HETATM   49  H26 UNL     1      -7.664  -0.316   1.480  1.00  0.00           H  
HETATM   50  H27 UNL     1      -5.468   2.500   0.458  1.00  0.00           H  
HETATM   51  H28 UNL     1      -6.803   2.519  -0.702  1.00  0.00           H  
HETATM   52  H29 UNL     1      -5.207   1.952  -1.238  1.00  0.00           H  
HETATM   53  H30 UNL     1      -1.927  -1.209  -2.905  1.00  0.00           H  
HETATM   54  H31 UNL     1      -0.061   0.345  -2.988  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3    4   27
CONECT    3   28   29   30
CONECT    4    5   31
CONECT    5    6   32   33
CONECT    6    7    8   34
CONECT    7   35
CONECT    8    9   36   37
CONECT    9   10
CONECT   10   11   11   23
CONECT   11   12   38
CONECT   12   13   13   39
CONECT   13   14   22
CONECT   14   15   40   41
CONECT   15   16
CONECT   16   17   42   43
CONECT   17   18   44   45
CONECT   18   19
CONECT   19   20   21   46
CONECT   20   47   48   49
CONECT   21   50   51   52
CONECT   22   23   23   53
CONECT   23   54
END

HMDB0257069
     RDKit          3D
r-(+)-bisoprolol
 54 54  0  0  0  0  0  0  0  0999 V2000
    7.0369   -1.1437    0.0093 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6089    0.0136   -0.8962 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9326    0.3250   -1.6715 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2952    1.1770   -0.2118 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2911    1.3505    0.7094 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8524    1.3989    0.3176 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1506    1.5975    1.5352 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2979    0.2087   -0.3751 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9933    0.2052   -0.6646 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7483    0.2015   -0.1994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2780    0.2388   -1.1677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5835    0.2347   -0.7655 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9676    0.1956    0.5514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3698    0.1943    1.0007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9827   -1.0562    0.9642 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1259   -1.6180   -0.2604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0654   -0.9870   -1.2258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3792   -0.9272   -0.9006 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8340   -0.2994    0.1984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6402   -1.3204    1.0231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8223    0.8043   -0.2753 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9602    0.1579    1.5122 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3547    0.1617    1.1150 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6447   -0.6677    0.8109 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6020   -1.8424   -0.6353 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2044   -1.6785    0.4544 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9566   -0.3794   -1.6824 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5833    0.8495   -0.9436 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3132   -0.6342   -2.0210 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6260    0.9619   -2.5265 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1319    1.7955   -0.0743 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4825    2.3404    1.2528 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3239    0.6279    1.5862 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6419    2.2896   -0.3519 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5695    0.9554    2.1776 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8459    0.1194   -1.3874 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5671   -0.7417    0.1982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0347    0.2684   -2.2160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3916    0.2675   -1.5074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4154    0.5337    2.0538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9356    0.9572    0.4212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1502   -1.8671   -0.7715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5531   -2.6561   -0.0679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0057   -1.5572   -2.2057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7567    0.0622   -1.4983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1201    0.1660    0.8665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5792   -1.5836    0.4690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9902   -2.1784    1.2159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9029   -0.8539    2.0059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3073    1.3023   -1.1198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0005    1.5126    0.5751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7282    0.2804   -0.6078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2654    0.1267    2.5642 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0908    0.1103    1.8899 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  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 13 22  1  0
 22 23  2  0
 23 10  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  3 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  6 34  1  0
  7 35  1  0
  8 36  1  0
  8 37  1  0
 11 38  1  0
 12 39  1  0
 14 40  1  0
 14 41  1  0
 16 42  1  0
 16 43  1  0
 17 44  1  0
 17 45  1  0
 19 46  1  0
 20 47  1  0
 20 48  1  0
 20 49  1  0
 21 50  1  0
 21 51  1  0
 21 52  1  0
 22 53  1  0
 23 54  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(+-)-1-((alpha-(2-Isopropoxyethoxy)-p-tolyl)oxy)-3-(isopropylamino)-2-propanol	ChEBI
(RS)-1-(4-(2-Isopropoxyethoxymethyl)phenoxy)-3-(isopropylamino)-2-propanol	ChEBI
Bisoprololum	ChEBI
(+-)-1-((a-(2-Isopropoxyethoxy)-p-tolyl)oxy)-3-(isopropylamino)-2-propanol	Generator
(+-)-1-((Α-(2-isopropoxyethoxy)-p-tolyl)oxy)-3-(isopropylamino)-2-propanol	Generator
Bisoprolol fumarate	HMDB
Bisoprolol fumerate	HMDB
Bisoprolol hemifumarate	HMDB
Bisoprolol fumarate (2:1) salt, (+-)-isomer	MeSH, HMDB
Bisoprolol, (-)-isomer	MeSH, HMDB
Bisoprolol, fumarate (1:1) salt	MeSH, HMDB
Merck brand OF bisoprolol fumarate	MeSH, HMDB
Bisoprolol hydrochloride	MeSH, HMDB
Bisoprolol, (+-)-isomer	MeSH, HMDB
Bisoprolol, fumarate (2:1) salt	MeSH, HMDB
Fumarate, bisoprolol	MeSH, HMDB
Bisoprolol fumarate (1:1) salt, (+-)-isomer	MeSH, HMDB
Bisoprolol methanesulfonate salt	MeSH, HMDB
Concor	MeSH, HMDB
Hydrochloride, bisoprolol	MeSH, HMDB

Chemical Formula

C₁₈H₃₁NO₄

Average Molecular Weight

325.443

Monoisotopic Molecular Weight

325.225308485

IUPAC Name

1-[(propan-2-yl)amino]-3-(4-{[2-(propan-2-yloxy)ethoxy]methyl}phenoxy)propan-2-ol

Traditional Name

1-{4-[(2-isopropoxyethoxy)methyl]phenoxy}-3-(isopropylamino)propan-2-ol

CAS Registry Number

66722-44-9

SMILES

CC(C)NCC(O)COC1=CC=C(COCCOC(C)C)C=C1

InChI Identifier

InChI=1S/C18H31NO4/c1-14(2)19-11-17(20)13-23-18-7-5-16(6-8-18)12-21-9-10-22-15(3)4/h5-8,14-15,17,19-20H,9-13H2,1-4H3

InChI Key

VHYCDWMUTMEGQY-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzylethers. These are aromatic ethers with the general formula ROCR' (R = alkyl, aryl; R'=benzene).

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzylethers

Direct Parent

Benzylethers

Alternative Parents

Substituents

Benzylether
Phenoxy compound
Phenol ether
Alkyl aryl ether
1,2-aminoalcohol
Secondary alcohol
Dialkyl ether
Secondary amine
Secondary aliphatic amine
Ether
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organopnictogen compound
Amine
Organic oxygen compound
Alcohol
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

secondary alcohol (CHEBI:3127 )
secondary amine (CHEBI:3127 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0014750)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Bisoprolol Action Pathway (PathBank: SMP0000300)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	100 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.071 g/L	Not Available
LogP	2.2	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	192.2	30932474

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.071 g/L	ALOGPS
logP	2.3	ALOGPS
logP	2.2	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	14.09	ChemAxon
pKa (Strongest Basic)	9.67	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	59.95 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	92.15 m³·mol⁻¹	ChemAxon
Polarizability	38.5 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	177.624	31661259
DarkChem	[M-H]-	176.492	31661259
DeepCCS	[M+H]+	186.222	30932474
DeepCCS	[M-H]-	183.864	30932474
DeepCCS	[M-2H]-	216.751	30932474
DeepCCS	[M+Na]+	192.315	30932474
AllCCS	[M+H]+	184.0	32859911
AllCCS	[M+H-H2O]+	181.3	32859911
AllCCS	[M+NH4]+	186.4	32859911
AllCCS	[M+Na]+	187.1	32859911
AllCCS	[M-H]-	180.2	32859911
AllCCS	[M+Na-2H]-	181.3	32859911
AllCCS	[M+HCOO]-	182.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Bisoprolol	CC(C)NCC(O)COC1=CC=C(COCCOC(C)C)C=C1	2841.6	Standard polar	33892256
Bisoprolol	CC(C)NCC(O)COC1=CC=C(COCCOC(C)C)C=C1	2316.0	Standard non polar	33892256
Bisoprolol	CC(C)NCC(O)COC1=CC=C(COCCOC(C)C)C=C1	2320.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Bisoprolol,1TMS,isomer #1	CC(C)NCC(COC1=CC=C(COCCOC(C)C)C=C1)O[Si](C)(C)C	2364.0	Semi standard non polar	33892256
Bisoprolol,1TMS,isomer #2	CC(C)OCCOCC1=CC=C(OCC(O)CN(C(C)C)[Si](C)(C)C)C=C1	2518.6	Semi standard non polar	33892256
Bisoprolol,2TMS,isomer #1	CC(C)OCCOCC1=CC=C(OCC(CN(C(C)C)[Si](C)(C)C)O[Si](C)(C)C)C=C1	2541.3	Semi standard non polar	33892256
Bisoprolol,2TMS,isomer #1	CC(C)OCCOCC1=CC=C(OCC(CN(C(C)C)[Si](C)(C)C)O[Si](C)(C)C)C=C1	2465.9	Standard non polar	33892256
Bisoprolol,2TMS,isomer #1	CC(C)OCCOCC1=CC=C(OCC(CN(C(C)C)[Si](C)(C)C)O[Si](C)(C)C)C=C1	2772.7	Standard polar	33892256
Bisoprolol,1TBDMS,isomer #1	CC(C)NCC(COC1=CC=C(COCCOC(C)C)C=C1)O[Si](C)(C)C(C)(C)C	2576.9	Semi standard non polar	33892256
Bisoprolol,1TBDMS,isomer #2	CC(C)OCCOCC1=CC=C(OCC(O)CN(C(C)C)[Si](C)(C)C(C)(C)C)C=C1	2762.7	Semi standard non polar	33892256
Bisoprolol,2TBDMS,isomer #1	CC(C)OCCOCC1=CC=C(OCC(CN(C(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C=C1	2998.6	Semi standard non polar	33892256
Bisoprolol,2TBDMS,isomer #1	CC(C)OCCOCC1=CC=C(OCC(CN(C(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C=C1	2819.1	Standard non polar	33892256
Bisoprolol,2TBDMS,isomer #1	CC(C)OCCOCC1=CC=C(OCC(CN(C(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C=C1	2961.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Bisoprolol GC-MS (Non-derivatized) - 70eV, Positive	splash10-05g0-9851000000-9065ddf0b986c238395e	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bisoprolol GC-MS (1 TMS) - 70eV, Positive	splash10-0006-9562000000-44cee6d913e8cf6bf735	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bisoprolol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bisoprolol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bisoprolol GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bisoprolol GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bisoprolol GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bisoprolol LC-ESI-QFT , positive-QTOF	splash10-004i-0109000000-564ffde4ea3f59c4126f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bisoprolol LC-ESI-QFT , positive-QTOF	splash10-014i-2903000000-5e5b905ef2026aa7f011	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bisoprolol LC-ESI-QFT , positive-QTOF	splash10-00xr-9800000000-99ce6ca7b3171d63af09	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bisoprolol LC-ESI-QFT , positive-QTOF	splash10-00di-9600000000-bfefc02f00a4439a34ba	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bisoprolol LC-ESI-QFT , positive-QTOF	splash10-05fr-9500000000-4b91d206ced038eff35c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bisoprolol LC-ESI-QFT , positive-QTOF	splash10-0ab9-9400000000-dd6baeb57f900d719aa9	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bisoprolol LC-ESI-QTOF , positive-QTOF	splash10-004i-0209000000-0f37dcfed3fc1c82c470	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bisoprolol LC-ESI-QTOF , positive-QTOF	splash10-014i-5902000000-dae2a435db6b3ea664cd	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bisoprolol LC-ESI-QTOF , positive-QTOF	splash10-05fr-9200000000-1cce569461a677bb6467	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bisoprolol , positive-QTOF	splash10-004i-0209000000-65dd49cd88f0ec134445	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bisoprolol LC-ESI-QFT , positive-QTOF	splash10-00or-5709000000-360e67ed724045a9c01b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bisoprolol 50V, Positive-QTOF	splash10-00ls-0900000000-9da1c89fab3eea35e2eb	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bisoprolol 20V, Positive-QTOF	splash10-004i-0109000000-0803087ee41a5f4756c4	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bisoprolol 10V, Positive-QTOF	splash10-004i-0009000000-4d3d24ad95cf8450432d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bisoprolol 30V, Positive-QTOF	splash10-014i-2903000000-a9ff8f842678e678f910	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bisoprolol 30V, Positive-QTOF	splash10-02vj-0902000000-601e7b32ea2f0c989a17	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bisoprolol 40V, Positive-QTOF	splash10-001j-0900000000-215dd14dd5c87dd8442f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bisoprolol 15V, Positive-QTOF	splash10-004i-0109000000-0e51abd9a44743e421b7	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bisoprolol 40V, Positive-QTOF	splash10-05fr-9200000000-1462679b0a1084c8ae26	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bisoprolol 10V, Positive-QTOF	splash10-00b9-4297000000-cc0bff99b7a745bbca62	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bisoprolol 20V, Positive-QTOF	splash10-00xr-7491000000-d270467937f89462ccd9	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bisoprolol 40V, Positive-QTOF	splash10-074l-9100000000-4cf48884e326a5069985	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bisoprolol 10V, Negative-QTOF	splash10-0ab9-5389000000-210c2d248c7ee6203c45	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bisoprolol 20V, Negative-QTOF	splash10-0a4i-7790000000-a567fd9f374a204b97ff	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bisoprolol 40V, Negative-QTOF	splash10-0a4i-9400000000-6a382f7e8c32a2d8a71c	2016-08-03	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Bisoprolol 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 DB00612	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00612	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00612

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2312

KEGG Compound ID

C06852

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Bisoprolol

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

3127

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

References

Horikiri Y, Suzuki T, Mizobe M: Pharmacokinetics and metabolism of bisoprolol enantiomers in humans. J Pharm Sci. 1998 Mar;87(3):289-94. [PubMed:9523980 ]
Horikiri Y, Suzuki T, Mizobe M: Stereoselective metabolism of bisoprolol enantiomers in dogs and humans. Life Sci. 1998;63(13):1097-108. [PubMed:9763205 ]
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. 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

Horikiri Y, Suzuki T, Mizobe M: Pharmacokinetics and metabolism of bisoprolol enantiomers in humans. J Pharm Sci. 1998 Mar;87(3):289-94. [PubMed:9523980 ]
Horikiri Y, Suzuki T, Mizobe M: Stereoselective metabolism of bisoprolol enantiomers in dogs and humans. Life Sci. 1998;63(13):1097-108. [PubMed:9763205 ]
Nozawa T, Taguchi M, Tahara K, Hashimoto Y, Igarashi N, Nonomura M, Kato B, Igawa A, Inoue H: Influence of CYP2D6 genotype on metoprolol plasma concentration and beta-adrenergic inhibition during long-term treatment: a comparison with bisoprolol. J Cardiovasc Pharmacol. 2005 Nov;46(5):713-20. [PubMed:16220080 ]
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

3. 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

Breed JG, Ciampricotti R, Tromp GP, Valster FA, Lageweg E, Van Bortel LM: Quality of life perception during antihypertensive treatment: a comparative study of bisoprolol and enalapril. J Cardiovasc Pharmacol. 1992;20(5):750-5. [PubMed:1280737 ]
Brouri F, Hanoun N, Mediani O, Saurini F, Hamon M, Vanhoutte PM, Lechat P: Blockade of beta 1- and desensitization of beta 2-adrenoceptors reduce isoprenaline-induced cardiac fibrosis. Eur J Pharmacol. 2004 Feb 6;485(1-3):227-34. [PubMed:14757145 ]
Bruck H, Leineweber K, Temme T, Weber M, Heusch G, Philipp T, Brodde OE: The Arg389Gly beta1-adrenoceptor polymorphism and catecholamine effects on plasma-renin activity. J Am Coll Cardiol. 2005 Dec 6;46(11):2111-5. Epub 2005 Nov 4. [PubMed:16325050 ]
Lipworth BJ, Irvine NA, McDevitt DG: A dose-ranging study to evaluate the beta 1-adrenoceptor selectivity of bisoprolol. Eur J Clin Pharmacol. 1991;40(2):135-9. [PubMed:1676675 ]
Mauz AB, Pelzer H: Beta-adrenoceptor-binding studies of the cardioselective beta blockers bisoprolol, H-I 42 BS, and HX-CH 44 BS to heart membranes and intact ventricular myocytes of adult rats: two beta 1-binding sites for bisoprolol. J Cardiovasc Pharmacol. 1990 Mar;15(3):421-7. [PubMed:1691366 ]
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. 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

Brouri F, Hanoun N, Mediani O, Saurini F, Hamon M, Vanhoutte PM, Lechat P: Blockade of beta 1- and desensitization of beta 2-adrenoceptors reduce isoprenaline-induced cardiac fibrosis. Eur J Pharmacol. 2004 Feb 6;485(1-3):227-34. [PubMed:14757145 ]
Bruck H, Poller U, Lussenhop H, Ponicke K, Temme T, Heusch G, Philipp T, Brodde OE: Beta 2-adrenoceptor-mediated intrinsic sympathomimetic activity of carteolol: an in vivo study. Naunyn Schmiedebergs Arch Pharmacol. 2004 Nov;370(5):361-8. Epub 2004 Oct 23. [PubMed:15526107 ]
Motomura S, Reinhard-Zerkowski H, Daul A, Brodde OE: On the physiologic role of beta-2 adrenoceptors in the human heart: in vitro and in vivo studies. Am Heart J. 1990 Mar;119(3 Pt 1):608-19. [PubMed:1968697 ]
Brodde OE: Bisoprolol (EMD 33512), a highly selective beta 1-adrenoceptor antagonist: in vitro and in vivo studies. J Cardiovasc Pharmacol. 1986;8 Suppl 11:S29-35. [PubMed:2439795 ]
Daul A, Johnston T, Reher M, Kruger M, Brodde OE: Differential haemodynamic effects induced by beta 1-(bisoprolol) or beta 2-(ICI 118,551) adrenoceptor blockade in man. J Hypertens Suppl. 1986 Dec;4(6):S99-102. [PubMed:2886573 ]

Showing metabocard for Bisoprolol (HMDB0014750)

MOL for HMDB0014750 (Bisoprolol)

3D MOL for HMDB0014750 (Bisoprolol)

3D SDF for HMDB0014750 (Bisoprolol)

3D-SDF for HMDB0014750 (Bisoprolol)

PDB for HMDB0014750 (Bisoprolol)

3D PDB for HMDB0014750 (Bisoprolol)

SMILES for HMDB0014750 (Bisoprolol)

INCHI for HMDB0014750 (Bisoprolol)

Structure for HMDB0014750 (Bisoprolol)

3D Structure for HMDB0014750 (Bisoprolol)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

References