Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (3)transporters (2) Show 5 proteins XML

enzymes (3)transporters (2) Show 5 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:56 UTC

HMDB ID

HMDB0015324

Secondary Accession Numbers

HMDB15324

Metabolite Identification

Common Name

Acebutolol

Description

Acebutolol is only found in individuals that have used or taken this drug. It is a cardioselective beta-adrenergic antagonist with little effect on the bronchial receptors. The drug has stabilizing and quinidine-like effects on cardiac rhythm as well as weak inherent sympathomimetic action. [PubChem]Acebutolol is a selective β1-receptor antagonist. Activation of β1-receptors by epinephrine increases the heart rate and the blood pressure, and the heart consumes more oxygen. Acebutolol blocks these receptors, lowering the heart rate and blood pressure. This drug then has the reverse effect of epinephrine. In addition, beta blockers prevent the release of renin, which is a hormone produced by the kidneys which leads to constriction of blood vessels.

Structure

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

HMDB0015324
     RDKit          3D
Acebutolol
 52 52  0  0  0  0  0  0  0  0999 V2000
   -7.1942    0.3282    1.5820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2417   -1.0942    1.0848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4272   -1.1828   -0.1772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9985   -0.8149    0.0421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6562   -0.5754    1.2072 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0898   -0.7454   -1.0232 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7317   -0.4238   -1.0098 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0366   -0.2366    0.1510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6926    0.1045    0.1011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0198    0.2629   -1.0905 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3195    0.6018   -1.1365 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9709    0.7803    0.1015 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4419    1.1714   -0.0591 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4540    2.3847   -0.8081 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9133    1.4499    1.3456 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9675    0.3047    2.1440 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9631   -0.6605    2.0074 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3074    0.0114    2.3343 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1212   -1.4441    0.7670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7211    0.0736   -2.2554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0903    0.2472   -3.5481 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3156    0.6628   -3.6758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7484    0.0440   -4.6204 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0761   -0.2696   -2.2388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4317    0.3686    2.3914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8579    0.9757    0.7622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1602    0.6478    2.0188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8657   -1.7644    1.8829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2918   -1.3238    0.8052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4829   -2.2629   -0.4875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8882   -0.6098   -1.0048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5050   -0.9707   -1.9995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4764   -0.3398    1.1081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1406    0.2542    0.9968 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8779   -0.1634    0.6780 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4741    1.5538    0.7296 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9512    0.3855   -0.5898 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4454    2.1010   -1.7750 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1371    2.1447    1.8112 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8475    2.0686    1.3479 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5925    0.3473    3.1000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7986   -1.4224    2.8425 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5130    0.7295    1.5229 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2065    0.5869    3.2777 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1260   -0.7300    2.3399 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7514   -2.3589    1.0493 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7051   -0.9522   -0.0464 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1590   -1.7768    0.3437 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9654   -0.0913   -3.2147 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5706    0.7893   -4.7677 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5303    1.6447   -3.1812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6016   -0.4107   -3.1665 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 10 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
 20 24  2  0
 24  7  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  6 32  1  0
  8 33  1  0
  9 34  1  0
 12 35  1  0
 12 36  1  0
 13 37  1  0
 14 38  1  0
 15 39  1  0
 15 40  1  0
 16 41  1  0
 17 42  1  0
 18 43  1  0
 18 44  1  0
 18 45  1  0
 19 46  1  0
 19 47  1  0
 19 48  1  0
 22 49  1  0
 22 50  1  0
 22 51  1  0
 24 52  1  0
M  END

1193
  Mrv0541 02231215182D          

 24 24  0  0  1  0            999 V2000
    5.9370    1.4438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    2.2688    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    2.6813    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0804   -1.4438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    1.4438    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.7949   -0.2063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659    1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0804    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0804    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5094   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5094   -2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659    2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7949   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2239   -2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0804    2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 10  1  0  0  0  0
  1 13  1  0  0  0  0
  2  7  1  0  0  0  0
  3 21  2  0  0  0  0
  4 22  2  0  0  0  0
  5  8  1  0  0  0  0
  5  9  1  0  0  0  0
  6 15  1  0  0  0  0
  6 22  1  0  0  0  0
  7  8  1  0  0  0  0
  7 10  1  0  0  0  0
  9 11  1  0  0  0  0
  9 12  1  0  0  0  0
 13 14  2  0  0  0  0
 13 17  1  0  0  0  0
 14 16  1  0  0  0  0
 14 21  1  0  0  0  0
 15 16  2  0  0  0  0
 15 18  1  0  0  0  0
 17 18  2  0  0  0  0
 19 20  1  0  0  0  0
 19 22  1  0  0  0  0
 20 23  1  0  0  0  0
 21 24  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015324

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCC(=O)NC1=CC(C(C)=O)=C(OCC(O)CNC(C)C)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C18H28N2O4/c1-5-6-18(23)20-14-7-8-17(16(9-14)13(4)21)24-11-15(22)10-19-12(2)3/h7-9,12,15,19,22H,5-6,10-11H2,1-4H3,(H,20,23)

> <INCHI_KEY>
GOEMGAFJFRBGGG-UHFFFAOYSA-N

> <FORMULA>
C18H28N2O4

> <MOLECULAR_WEIGHT>
336.4259

> <EXACT_MASS>
336.204907394

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
38.506102083275465

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-(3-acetyl-4-{2-hydroxy-3-[(propan-2-yl)amino]propoxy}phenyl)butanamide

> <ALOGPS_LOGP>
1.43

> <JCHEM_LOGP>
1.5346815706666663

> <ALOGPS_LOGS>
-3.29

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.561117473592265

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.912071129909538

> <JCHEM_PKA_STRONGEST_BASIC>
9.566244843597062

> <JCHEM_POLAR_SURFACE_AREA>
87.66

> <JCHEM_REFRACTIVITY>
94.8692

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.72e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
acebutolol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015324
     RDKit          3D
Acebutolol
 52 52  0  0  0  0  0  0  0  0999 V2000
   -7.1942    0.3282    1.5820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2417   -1.0942    1.0848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4272   -1.1828   -0.1772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9985   -0.8149    0.0421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6562   -0.5754    1.2072 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0898   -0.7454   -1.0232 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7317   -0.4238   -1.0098 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0366   -0.2366    0.1510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6926    0.1045    0.1011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0198    0.2629   -1.0905 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3195    0.6018   -1.1365 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9709    0.7803    0.1015 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4419    1.1714   -0.0591 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4540    2.3847   -0.8081 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9133    1.4499    1.3456 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9675    0.3047    2.1440 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9631   -0.6605    2.0074 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3074    0.0114    2.3343 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1212   -1.4441    0.7670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7211    0.0736   -2.2554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0903    0.2472   -3.5481 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3156    0.6628   -3.6758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7484    0.0440   -4.6204 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0761   -0.2696   -2.2388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4317    0.3686    2.3914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8579    0.9757    0.7622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1602    0.6478    2.0188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8657   -1.7644    1.8829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2918   -1.3238    0.8052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4829   -2.2629   -0.4875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8882   -0.6098   -1.0048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5050   -0.9707   -1.9995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4764   -0.3398    1.1081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1406    0.2542    0.9968 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8779   -0.1634    0.6780 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4741    1.5538    0.7296 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9512    0.3855   -0.5898 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4454    2.1010   -1.7750 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1371    2.1447    1.8112 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8475    2.0686    1.3479 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5925    0.3473    3.1000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7986   -1.4224    2.8425 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5130    0.7295    1.5229 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2065    0.5869    3.2777 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1260   -0.7300    2.3399 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7514   -2.3589    1.0493 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7051   -0.9522   -0.0464 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1590   -1.7768    0.3437 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9654   -0.0913   -3.2147 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5706    0.7893   -4.7677 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5303    1.6447   -3.1812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6016   -0.4107   -3.1665 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 10 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
 20 24  2  0
 24  7  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  6 32  1  0
  8 33  1  0
  9 34  1  0
 12 35  1  0
 12 36  1  0
 13 37  1  0
 14 38  1  0
 15 39  1  0
 15 40  1  0
 16 41  1  0
 17 42  1  0
 18 43  1  0
 18 44  1  0
 18 45  1  0
 19 46  1  0
 19 47  1  0
 19 48  1  0
 22 49  1  0
 22 50  1  0
 22 51  1  0
 24 52  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1193                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      11.082   2.695   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       8.415   4.235   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      12.416   5.005   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      15.083  -2.695   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0       5.748   2.695   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0      16.417  -0.385   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       8.415   2.695   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.081   1.925   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.414   1.925   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.748   1.925   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.080   2.695   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.414   0.385   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.416   1.925   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.750   2.695   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      15.083   0.385   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      15.083   1.925   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.416   0.385   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.750  -0.385   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      17.751  -2.695   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      17.751  -4.235   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.750   4.235   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      16.417  -1.925   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      19.085  -5.005   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      15.083   5.005   0.000  0.00  0.00           C+0
CONECT    1   10   13                                                       
CONECT    2    7                                                            
CONECT    3   21                                                            
CONECT    4   22                                                            
CONECT    5    8    9                                                       
CONECT    6   15   22                                                       
CONECT    7    2    8   10                                                  
CONECT    8    5    7                                                       
CONECT    9    5   11   12                                                  
CONECT   10    1    7                                                       
CONECT   11    9                                                            
CONECT   12    9                                                            
CONECT   13    1   14   17                                                  
CONECT   14   13   16   21                                                  
CONECT   15    6   16   18                                                  
CONECT   16   14   15                                                       
CONECT   17   13   18                                                       
CONECT   18   15   17                                                       
CONECT   19   20   22                                                       
CONECT   20   19   23                                                       
CONECT   21    3   14   24                                                  
CONECT   22    4    6   19                                                  
CONECT   23   20                                                            
CONECT   24   21                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   48    0
END

COMPND    HMDB0015324
HETATM    1  C1  UNL     1      -7.194   0.328   1.582  1.00  0.00           C  
HETATM    2  C2  UNL     1      -7.242  -1.094   1.085  1.00  0.00           C  
HETATM    3  C3  UNL     1      -6.427  -1.183  -0.177  1.00  0.00           C  
HETATM    4  C4  UNL     1      -4.999  -0.815   0.042  1.00  0.00           C  
HETATM    5  O1  UNL     1      -4.656  -0.575   1.207  1.00  0.00           O  
HETATM    6  N1  UNL     1      -4.090  -0.745  -1.023  1.00  0.00           N  
HETATM    7  C5  UNL     1      -2.732  -0.424  -1.010  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.037  -0.237   0.151  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.693   0.105   0.101  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.020   0.263  -1.091  1.00  0.00           C  
HETATM   11  O2  UNL     1       1.319   0.602  -1.136  1.00  0.00           O  
HETATM   12  C9  UNL     1       1.971   0.780   0.101  1.00  0.00           C  
HETATM   13  C10 UNL     1       3.442   1.171  -0.059  1.00  0.00           C  
HETATM   14  O3  UNL     1       3.454   2.385  -0.808  1.00  0.00           O  
HETATM   15  C11 UNL     1       3.913   1.450   1.346  1.00  0.00           C  
HETATM   16  N2  UNL     1       3.968   0.305   2.144  1.00  0.00           N  
HETATM   17  C12 UNL     1       4.963  -0.660   2.007  1.00  0.00           C  
HETATM   18  C13 UNL     1       6.307   0.011   2.334  1.00  0.00           C  
HETATM   19  C14 UNL     1       5.121  -1.444   0.767  1.00  0.00           C  
HETATM   20  C15 UNL     1      -0.721   0.074  -2.255  1.00  0.00           C  
HETATM   21  C16 UNL     1      -0.090   0.247  -3.548  1.00  0.00           C  
HETATM   22  C17 UNL     1       1.316   0.663  -3.676  1.00  0.00           C  
HETATM   23  O4  UNL     1      -0.748   0.044  -4.620  1.00  0.00           O  
HETATM   24  C18 UNL     1      -2.076  -0.270  -2.239  1.00  0.00           C  
HETATM   25  H1  UNL     1      -6.432   0.369   2.391  1.00  0.00           H  
HETATM   26  H2  UNL     1      -6.858   0.976   0.762  1.00  0.00           H  
HETATM   27  H3  UNL     1      -8.160   0.648   2.019  1.00  0.00           H  
HETATM   28  H4  UNL     1      -6.866  -1.764   1.883  1.00  0.00           H  
HETATM   29  H5  UNL     1      -8.292  -1.324   0.805  1.00  0.00           H  
HETATM   30  H6  UNL     1      -6.483  -2.263  -0.488  1.00  0.00           H  
HETATM   31  H7  UNL     1      -6.888  -0.610  -1.005  1.00  0.00           H  
HETATM   32  H8  UNL     1      -4.505  -0.971  -2.000  1.00  0.00           H  
HETATM   33  H9  UNL     1      -2.476  -0.340   1.108  1.00  0.00           H  
HETATM   34  H10 UNL     1      -0.141   0.254   0.997  1.00  0.00           H  
HETATM   35  H11 UNL     1       1.878  -0.163   0.678  1.00  0.00           H  
HETATM   36  H12 UNL     1       1.474   1.554   0.730  1.00  0.00           H  
HETATM   37  H13 UNL     1       3.951   0.386  -0.590  1.00  0.00           H  
HETATM   38  H14 UNL     1       3.445   2.101  -1.775  1.00  0.00           H  
HETATM   39  H15 UNL     1       3.137   2.145   1.811  1.00  0.00           H  
HETATM   40  H16 UNL     1       4.847   2.069   1.348  1.00  0.00           H  
HETATM   41  H17 UNL     1       3.593   0.347   3.100  1.00  0.00           H  
HETATM   42  H18 UNL     1       4.799  -1.422   2.843  1.00  0.00           H  
HETATM   43  H19 UNL     1       6.513   0.730   1.523  1.00  0.00           H  
HETATM   44  H20 UNL     1       6.207   0.587   3.278  1.00  0.00           H  
HETATM   45  H21 UNL     1       7.126  -0.730   2.340  1.00  0.00           H  
HETATM   46  H22 UNL     1       5.751  -2.359   1.049  1.00  0.00           H  
HETATM   47  H23 UNL     1       5.705  -0.952  -0.046  1.00  0.00           H  
HETATM   48  H24 UNL     1       4.159  -1.777   0.344  1.00  0.00           H  
HETATM   49  H25 UNL     1       1.965  -0.091  -3.215  1.00  0.00           H  
HETATM   50  H26 UNL     1       1.571   0.789  -4.768  1.00  0.00           H  
HETATM   51  H27 UNL     1       1.530   1.645  -3.181  1.00  0.00           H  
HETATM   52  H28 UNL     1      -2.602  -0.411  -3.166  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3   28   29
CONECT    3    4   30   31
CONECT    4    5    5    6
CONECT    6    7   32
CONECT    7    8    8   24
CONECT    8    9   33
CONECT    9   10   10   34
CONECT   10   11   20
CONECT   11   12
CONECT   12   13   35   36
CONECT   13   14   15   37
CONECT   14   38
CONECT   15   16   39   40
CONECT   16   17   41
CONECT   17   18   19   42
CONECT   18   43   44   45
CONECT   19   46   47   48
CONECT   20   21   24   24
CONECT   21   22   23   23
CONECT   22   49   50   51
CONECT   24   52
END

HMDB0015324
     RDKit          3D
Acebutolol
 52 52  0  0  0  0  0  0  0  0999 V2000
   -7.1942    0.3282    1.5820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2417   -1.0942    1.0848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4272   -1.1828   -0.1772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9985   -0.8149    0.0421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6562   -0.5754    1.2072 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0898   -0.7454   -1.0232 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7317   -0.4238   -1.0098 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0366   -0.2366    0.1510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6926    0.1045    0.1011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0198    0.2629   -1.0905 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3195    0.6018   -1.1365 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9709    0.7803    0.1015 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4419    1.1714   -0.0591 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4540    2.3847   -0.8081 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9133    1.4499    1.3456 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9675    0.3047    2.1440 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9631   -0.6605    2.0074 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3074    0.0114    2.3343 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1212   -1.4441    0.7670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7211    0.0736   -2.2554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0903    0.2472   -3.5481 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3156    0.6628   -3.6758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7484    0.0440   -4.6204 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0761   -0.2696   -2.2388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4317    0.3686    2.3914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8579    0.9757    0.7622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1602    0.6478    2.0188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8657   -1.7644    1.8829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2918   -1.3238    0.8052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4829   -2.2629   -0.4875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8882   -0.6098   -1.0048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5050   -0.9707   -1.9995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4764   -0.3398    1.1081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1406    0.2542    0.9968 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8779   -0.1634    0.6780 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4741    1.5538    0.7296 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9512    0.3855   -0.5898 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4454    2.1010   -1.7750 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1371    2.1447    1.8112 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8475    2.0686    1.3479 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5925    0.3473    3.1000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7986   -1.4224    2.8425 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5130    0.7295    1.5229 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2065    0.5869    3.2777 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1260   -0.7300    2.3399 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7514   -2.3589    1.0493 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7051   -0.9522   -0.0464 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1590   -1.7768    0.3437 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9654   -0.0913   -3.2147 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5706    0.7893   -4.7677 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5303    1.6447   -3.1812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6016   -0.4107   -3.1665 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 10 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
 20 24  2  0
 24  7  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  6 32  1  0
  8 33  1  0
  9 34  1  0
 12 35  1  0
 12 36  1  0
 13 37  1  0
 14 38  1  0
 15 39  1  0
 15 40  1  0
 16 41  1  0
 17 42  1  0
 18 43  1  0
 18 44  1  0
 18 45  1  0
 19 46  1  0
 19 47  1  0
 19 48  1  0
 22 49  1  0
 22 50  1  0
 22 51  1  0
 24 52  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(+-)-Acebutolol	ChEBI
3'-Acetyl-4'-(2-hydroxy-3-(isopropylamino)propoxy)butyranilide	ChEBI
5'-Butyramido-2'-(2-hydroxy-3-isopropylaminopropoxy)acetophenone	ChEBI
Acebutololum	ChEBI
Acetobutolol	ChEBI
N-(3-Acetyl-4-[2-hydroxy-3-(isopropylamino)propoxy]phenyl)butanamide	ChEBI
N-[3-Acetyl-4-[2-hydroxy-3-[(1-methylethyl)amino]propoxy]phenyl]butanamide	ChEBI
Acebutolol HCL	HMDB
Acebutolol hydrochloride	HMDB
Acebutololo	HMDB
DL-Acebutolol	HMDB
Lafon ratiopharm brand OF acebutolol hydrochloride	HMDB
NovoAcebutolol	HMDB
Bayer brand OF acebutolol hydrochloride	HMDB
Heumann brand OF acebutolol hydrochloride	HMDB
Italfarmaco brand OF acebutolol hydrochloride	HMDB
m And b 17803 a	HMDB
Novo acebutolol	HMDB
Prent	HMDB
Sectral	HMDB
Specia brand OF acebutolol hydrochloride	HMDB
Acebutolol gepepharm brand	HMDB
Apo acebutolol	HMDB
Apo-acebutolol	HMDB
Apotex brand OF acebutolol hydrochloride	HMDB
Gepepharm brand OF acebutolol	HMDB
Heumann, acebutolol	HMDB
m And b-17803 a	HMDB
m And b17803 a	HMDB
Monitan	HMDB
Novopharm brand OF acebutolol hydrochloride	HMDB
Proctor and gamble brand OF acebutolol hydrochloride	HMDB
Rhône poulenc rorer brand OF acebutolol hydrochloride	HMDB
Acebutolol heumann	HMDB
Acébutolol ratiopharm	HMDB
Acébutolol-ratiopharm	HMDB
Acébutololratiopharm	HMDB
ApoAcebutolol	HMDB
Hydrochloride, acebutolol	HMDB
Lafon-ratiopharm brand OF acebutolol hydrochloride	HMDB
m And b 17803a	HMDB
Neptal	HMDB
Novo-acebutolol	HMDB
Rhodiapharm brand OF acebutolol hydrochloride	HMDB
Rhotral	HMDB
Rhône-poulenc rorer brand OF acebutolol hydrochloride	HMDB
Wyeth brand OF acebutolol hydrochloride	HMDB

Chemical Formula

C₁₈H₂₈N₂O₄

Average Molecular Weight

336.4259

Monoisotopic Molecular Weight

336.204907394

IUPAC Name

N-(3-acetyl-4-{2-hydroxy-3-[(propan-2-yl)amino]propoxy}phenyl)butanamide

Traditional Name

acebutolol

CAS Registry Number

37517-30-9

SMILES

CCCC(=O)NC1=CC(C(C)=O)=C(OCC(O)CNC(C)C)C=C1

InChI Identifier

InChI=1S/C18H28N2O4/c1-5-6-18(23)20-14-7-8-17(16(9-14)13(4)21)24-11-15(22)10-19-12(2)3/h7-9,12,15,19,22H,5-6,10-11H2,1-4H3,(H,20,23)

InChI Key

GOEMGAFJFRBGGG-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Alkyl-phenylketones

Alternative Parents

Substituents

Alkyl-phenylketone
Acetophenone
Benzoyl
Phenol ether
Aryl alkyl ketone
Phenoxy compound
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
1,2-aminoalcohol
Secondary alcohol
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Carboximidic acid
Carboximidic acid derivative
Secondary aliphatic amine
Ether
Secondary amine
Organic oxide
Alcohol
Hydrocarbon derivative
Amine
Organonitrogen compound
Organic nitrogen compound
Organopnictogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

monocarboxylic acid amide (CHEBI:2379 )
secondary amino compound (CHEBI:2379 )
ether (CHEBI:2379 )
aromatic amide (CHEBI:2379 )
ethanolamines (CHEBI:2379 )
propanolamine (CHEBI:2379 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Blood (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0015324)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Acebutolol Action Pathway (PathBank: SMP0000296)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	119 - 123 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.17 g/L	Not Available
LogP	1.7	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	190.2	30932474
[M+H]+	Not Available	188.304	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001316

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.17 g/L	ALOGPS
logP	1.43	ALOGPS
logP	1.53	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	13.91	ChemAxon
pKa (Strongest Basic)	9.57	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	87.66 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	94.87 m³·mol⁻¹	ChemAxon
Polarizability	38.51 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]+	178.551	31661259
DarkChem	[M-H]-	180.135	31661259
DeepCCS	[M+H]+	186.938	30932474
DeepCCS	[M-H]-	184.58	30932474
DeepCCS	[M-2H]-	217.884	30932474
DeepCCS	[M+Na]+	193.11	30932474
AllCCS	[M+H]+	184.7	32859911
AllCCS	[M+H-H2O]+	182.0	32859911
AllCCS	[M+NH4]+	187.1	32859911
AllCCS	[M+Na]+	187.8	32859911
AllCCS	[M-H]-	182.0	32859911
AllCCS	[M+Na-2H]-	182.9	32859911
AllCCS	[M+HCOO]-	184.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Acebutolol	CCCC(=O)NC1=CC(C(C)=O)=C(OCC(O)CNC(C)C)C=C1	3634.3	Standard polar	33892256
Acebutolol	CCCC(=O)NC1=CC(C(C)=O)=C(OCC(O)CNC(C)C)C=C1	2813.6	Standard non polar	33892256
Acebutolol	CCCC(=O)NC1=CC(C(C)=O)=C(OCC(O)CNC(C)C)C=C1	2824.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Acebutolol,1TMS,isomer #1	CCCC(=O)NC1=CC=C(OCC(CNC(C)C)O[Si](C)(C)C)C(C(C)=O)=C1	2895.0	Semi standard non polar	33892256
Acebutolol,1TMS,isomer #2	CCCC(=O)N(C1=CC=C(OCC(O)CNC(C)C)C(C(C)=O)=C1)[Si](C)(C)C	2676.0	Semi standard non polar	33892256
Acebutolol,1TMS,isomer #3	CCCC(=O)NC1=CC=C(OCC(O)CN(C(C)C)[Si](C)(C)C)C(C(C)=O)=C1	2997.7	Semi standard non polar	33892256
Acebutolol,2TMS,isomer #1	CCCC(=O)N(C1=CC=C(OCC(CNC(C)C)O[Si](C)(C)C)C(C(C)=O)=C1)[Si](C)(C)C	2631.0	Semi standard non polar	33892256
Acebutolol,2TMS,isomer #1	CCCC(=O)N(C1=CC=C(OCC(CNC(C)C)O[Si](C)(C)C)C(C(C)=O)=C1)[Si](C)(C)C	2750.4	Standard non polar	33892256
Acebutolol,2TMS,isomer #1	CCCC(=O)N(C1=CC=C(OCC(CNC(C)C)O[Si](C)(C)C)C(C(C)=O)=C1)[Si](C)(C)C	3165.8	Standard polar	33892256
Acebutolol,2TMS,isomer #2	CCCC(=O)NC1=CC=C(OCC(CN(C(C)C)[Si](C)(C)C)O[Si](C)(C)C)C(C(C)=O)=C1	3020.5	Semi standard non polar	33892256
Acebutolol,2TMS,isomer #2	CCCC(=O)NC1=CC=C(OCC(CN(C(C)C)[Si](C)(C)C)O[Si](C)(C)C)C(C(C)=O)=C1	2851.4	Standard non polar	33892256
Acebutolol,2TMS,isomer #2	CCCC(=O)NC1=CC=C(OCC(CN(C(C)C)[Si](C)(C)C)O[Si](C)(C)C)C(C(C)=O)=C1	3419.8	Standard polar	33892256
Acebutolol,2TMS,isomer #3	CCCC(=O)N(C1=CC=C(OCC(O)CN(C(C)C)[Si](C)(C)C)C(C(C)=O)=C1)[Si](C)(C)C	2772.3	Semi standard non polar	33892256
Acebutolol,2TMS,isomer #3	CCCC(=O)N(C1=CC=C(OCC(O)CN(C(C)C)[Si](C)(C)C)C(C(C)=O)=C1)[Si](C)(C)C	2871.6	Standard non polar	33892256
Acebutolol,2TMS,isomer #3	CCCC(=O)N(C1=CC=C(OCC(O)CN(C(C)C)[Si](C)(C)C)C(C(C)=O)=C1)[Si](C)(C)C	3296.9	Standard polar	33892256
Acebutolol,3TMS,isomer #1	CCCC(=O)N(C1=CC=C(OCC(CN(C(C)C)[Si](C)(C)C)O[Si](C)(C)C)C(C(C)=O)=C1)[Si](C)(C)C	2805.1	Semi standard non polar	33892256
Acebutolol,3TMS,isomer #1	CCCC(=O)N(C1=CC=C(OCC(CN(C(C)C)[Si](C)(C)C)O[Si](C)(C)C)C(C(C)=O)=C1)[Si](C)(C)C	2844.6	Standard non polar	33892256
Acebutolol,3TMS,isomer #1	CCCC(=O)N(C1=CC=C(OCC(CN(C(C)C)[Si](C)(C)C)O[Si](C)(C)C)C(C(C)=O)=C1)[Si](C)(C)C	3049.5	Standard polar	33892256
Acebutolol,1TBDMS,isomer #1	CCCC(=O)NC1=CC=C(OCC(CNC(C)C)O[Si](C)(C)C(C)(C)C)C(C(C)=O)=C1	3147.7	Semi standard non polar	33892256
Acebutolol,1TBDMS,isomer #2	CCCC(=O)N(C1=CC=C(OCC(O)CNC(C)C)C(C(C)=O)=C1)[Si](C)(C)C(C)(C)C	2944.8	Semi standard non polar	33892256
Acebutolol,1TBDMS,isomer #3	CCCC(=O)NC1=CC=C(OCC(O)CN(C(C)C)[Si](C)(C)C(C)(C)C)C(C(C)=O)=C1	3269.6	Semi standard non polar	33892256
Acebutolol,2TBDMS,isomer #1	CCCC(=O)N(C1=CC=C(OCC(CNC(C)C)O[Si](C)(C)C(C)(C)C)C(C(C)=O)=C1)[Si](C)(C)C(C)(C)C	3089.5	Semi standard non polar	33892256
Acebutolol,2TBDMS,isomer #1	CCCC(=O)N(C1=CC=C(OCC(CNC(C)C)O[Si](C)(C)C(C)(C)C)C(C(C)=O)=C1)[Si](C)(C)C(C)(C)C	3136.5	Standard non polar	33892256
Acebutolol,2TBDMS,isomer #1	CCCC(=O)N(C1=CC=C(OCC(CNC(C)C)O[Si](C)(C)C(C)(C)C)C(C(C)=O)=C1)[Si](C)(C)C(C)(C)C	3324.2	Standard polar	33892256
Acebutolol,2TBDMS,isomer #2	CCCC(=O)NC1=CC=C(OCC(CN(C(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(C(C)=O)=C1	3522.3	Semi standard non polar	33892256
Acebutolol,2TBDMS,isomer #2	CCCC(=O)NC1=CC=C(OCC(CN(C(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(C(C)=O)=C1	3237.7	Standard non polar	33892256
Acebutolol,2TBDMS,isomer #2	CCCC(=O)NC1=CC=C(OCC(CN(C(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(C(C)=O)=C1	3520.3	Standard polar	33892256
Acebutolol,2TBDMS,isomer #3	CCCC(=O)N(C1=CC=C(OCC(O)CN(C(C)C)[Si](C)(C)C(C)(C)C)C(C(C)=O)=C1)[Si](C)(C)C(C)(C)C	3282.8	Semi standard non polar	33892256
Acebutolol,2TBDMS,isomer #3	CCCC(=O)N(C1=CC=C(OCC(O)CN(C(C)C)[Si](C)(C)C(C)(C)C)C(C(C)=O)=C1)[Si](C)(C)C(C)(C)C	3237.8	Standard non polar	33892256
Acebutolol,2TBDMS,isomer #3	CCCC(=O)N(C1=CC=C(OCC(O)CN(C(C)C)[Si](C)(C)C(C)(C)C)C(C(C)=O)=C1)[Si](C)(C)C(C)(C)C	3427.5	Standard polar	33892256
Acebutolol,3TBDMS,isomer #1	CCCC(=O)N(C1=CC=C(OCC(CN(C(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(C(C)=O)=C1)[Si](C)(C)C(C)(C)C	3517.9	Semi standard non polar	33892256
Acebutolol,3TBDMS,isomer #1	CCCC(=O)N(C1=CC=C(OCC(CN(C(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(C(C)=O)=C1)[Si](C)(C)C(C)(C)C	3381.3	Standard non polar	33892256
Acebutolol,3TBDMS,isomer #1	CCCC(=O)N(C1=CC=C(OCC(CN(C(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(C(C)=O)=C1)[Si](C)(C)C(C)(C)C	3304.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Acebutolol GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-9252000000-7827544ebe33c12ef3bb	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Acebutolol GC-MS (1 TMS) - 70eV, Positive	splash10-006x-4927000000-729380ab7bcc06a189bf	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Acebutolol 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Acebutolol 40V, Positive-QTOF	splash10-015a-0940000000-cd2be0ebcdc412c13c1d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Acebutolol 20V, Negative-QTOF	splash10-014i-0291000000-d2c79f57907dfecd3ab6	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Acebutolol 30V, Negative-QTOF	splash10-004i-0920000000-7ee5e8843c0d3c66cea4	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Acebutolol 50V, Positive-QTOF	splash10-007k-0900000000-86cb0a76fcc4e9480bed	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Acebutolol 40V, Negative-QTOF	splash10-004i-0900000000-d4a06670b3e12a3f0d4d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Acebutolol 10V, Negative-QTOF	splash10-000i-0009000000-72f0325748e2bf5430c4	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Acebutolol 50V, Negative-QTOF	splash10-004i-0900000000-b9cf35fe287fe7fa1e58	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Acebutolol 30V, Positive-QTOF	splash10-014r-0595000000-5ed3946399d12d6cbe7e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Acebutolol 40V, Positive-QTOF	splash10-015a-0940000000-d6b151173b7e6e7831de	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Acebutolol 20V, Positive-QTOF	splash10-000i-0009000000-bc4eec9d529011d6a177	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Acebutolol 10V, Positive-QTOF	splash10-000i-0009000000-6d0d67c3acd18ae44924	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acebutolol 10V, Positive-QTOF	splash10-014r-2095000000-a0c01f6fa89d23cb8b78	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acebutolol 20V, Positive-QTOF	splash10-00xr-6190000000-4fd1c0b6ff7eba1b576f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acebutolol 40V, Positive-QTOF	splash10-00dl-9110000000-5127458f77fd32591066	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acebutolol 10V, Negative-QTOF	splash10-0079-3179000000-b67d7480f1ca6f97c175	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acebutolol 20V, Negative-QTOF	splash10-00di-2490000000-15d368948cd4505e7114	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acebutolol 40V, Negative-QTOF	splash10-0002-4920000000-d65e636290545a9b04c5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acebutolol 10V, Positive-QTOF	splash10-000i-0019000000-80019c4cccdbe0d63d65	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acebutolol 20V, Positive-QTOF	splash10-00xr-9311000000-855c3de48116392e6d1d	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acebutolol 40V, Positive-QTOF	splash10-0abc-9000000000-40e5b46c1b5f9852aafe	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acebutolol 10V, Negative-QTOF	splash10-00kr-0696000000-2aa0e3161d69561d76c6	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acebutolol 20V, Negative-QTOF	splash10-0f6t-0920000000-98a8831324919178688e	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acebutolol 40V, Negative-QTOF	splash10-001i-2910000000-06dafa94cb8131dd5bda	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
Acebutolol 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 DB01193	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01193	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01193

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

1901

KEGG Compound ID

C06803

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Acebutolol

METLIN ID

Not Available

PubChem Compound

1978

PDB ID

Not Available

ChEBI ID

2379

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. Cytochrome P450 2D6

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

References

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

Enzyme Details

2. Beta-1 adrenergic receptor

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

References

van den Meiracker AH, Man in 't Veld AJ, Fischberg DJ, Molinoff PB, van Eck HJ, Boomsma F, Derkx FH, Schalekamp MA: Acute and long-term effects of acebutolol on systemic and renal hemodynamics, body fluid volumes, catecholamines, active renin, aldosterone, and lymphocyte beta-adrenoceptor density. J Cardiovasc Pharmacol. 1988 Apr;11(4):413-23. [PubMed:2453744 ]
Abrahamsson T: Characterization of the beta 1-adrenoceptor stimulatory effects of the partial beta 1-agonists acebutolol, xamoterol, H142/08 and H201/70. Eur J Pharmacol. 1989 May 2;164(1):121-8. [PubMed:2568935 ]
Fraysse B, Garric J: Prediction and experimental validation of acute toxicity of beta-blockers in Ceriodaphnia dubia. Environ Toxicol Chem. 2005 Oct;24(10):2470-6. [PubMed:16268148 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzyme Details

3. Beta-2 adrenergic receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: Beta-adrenergic receptors mediate the catecholamine- induced activation of adenylate cyclase through the action of G proteins. The beta-2-adrenergic receptor binds epinephrine with an approximately 30-fold greater affinity than it does norepinephrine
Gene Name:: ADRB2
Uniprot ID:: P07550
Molecular weight:: 46458.3

References

Fraysse B, Garric J: Prediction and experimental validation of acute toxicity of beta-blockers in Ceriodaphnia dubia. Environ Toxicol Chem. 2005 Oct;24(10):2470-6. [PubMed:16268148 ]
Varma DR, Shen H, Deng XF, Peri KG, Chemtob S, Mulay S: Inverse agonist activities of beta-adrenoceptor antagonists in rat myocardium. Br J Pharmacol. 1999 Jun;127(4):895-902. [PubMed:10433496 ]
Lima JJ: Relationship between beta adrenoceptor occupancy and receptor down-regulation induced by beta antagonists with intrinsic sympathomimetic activity. J Recept Signal Transduct Res. 1996 Sep-Nov;16(5-6):357-72. [PubMed:8968966 ]

Transporters

Enzyme Details

1. Multidrug resistance protein 1

General function:: Involved in ATP binding
Specific function:: Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
Gene Name:: ABCB1
Uniprot ID:: P08183
Molecular weight:: 141477.3

References

Troutman MD, Thakker DR: Novel experimental parameters to quantify the modulation of absorptive and secretory transport of compounds by P-glycoprotein in cell culture models of intestinal epithelium. Pharm Res. 2003 Aug;20(8):1210-24. [PubMed:12948019 ]
Terao T, Hisanaga E, Sai Y, Tamai I, Tsuji A: Active secretion of drugs from the small intestinal epithelium in rats by P-glycoprotein functioning as an absorption barrier. J Pharm Pharmacol. 1996 Oct;48(10):1083-9. [PubMed:8953513 ]

Enzyme Details

2. Solute carrier family 22 member 1

General function:: Involved in ion transmembrane transporter activity
Specific function:: Translocates a broad array of organic cations with various structures and molecular weights including the model compounds 1-methyl-4-phenylpyridinium (MPP), tetraethylammonium (TEA), N-1-methylnicotinamide (NMN), 4-(4-(dimethylamino)styryl)- N-methylpyridinium (ASP), the endogenous compounds choline, guanidine, histamine, epinephrine, adrenaline, noradrenaline and dopamine, and the drugs quinine, and metformin. The transport of organic cations is inhibited by a broad array of compounds like tetramethylammonium (TMA), cocaine, lidocaine, NMDA receptor antagonists, atropine, prazosin, cimetidine, TEA and NMN, guanidine, cimetidine, choline, procainamide, quinine, tetrabutylammonium, and tetrapentylammonium. Translocates organic cations in an electrogenic and pH-independent manner. Translocates organic cations across the plasma membrane in both directions. Transports the polyamines spermine and spermidine. Transports pramipexole across the basolateral membrane of the proximal tubular epithelial cells. The choline transport is activated by MMTS. Regulated by various intracellular signaling pathways including inhibition by protein kinase A activation, and endogenously activation by the calmodulin complex, the calmodulin- dependent kinase II and LCK tyrosine kinase
Gene Name:: SLC22A1
Uniprot ID:: O15245
Molecular weight:: 61187.4

References

Zhang L, Schaner ME, Giacomini KM: Functional characterization of an organic cation transporter (hOCT1) in a transiently transfected human cell line (HeLa). J Pharmacol Exp Ther. 1998 Jul;286(1):354-61. [PubMed:9655880 ]

Showing metabocard for Acebutolol (HMDB0015324)

MOL for HMDB0015324 (Acebutolol)

3D MOL for HMDB0015324 (Acebutolol)

3D SDF for HMDB0015324 (Acebutolol)

3D-SDF for HMDB0015324 (Acebutolol)

PDB for HMDB0015324 (Acebutolol)

3D PDB for HMDB0015324 (Acebutolol)

SMILES for HMDB0015324 (Acebutolol)

INCHI for HMDB0015324 (Acebutolol)

Structure for HMDB0015324 (Acebutolol)

3D Structure for HMDB0015324 (Acebutolol)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

Transporters

References

References