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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2022-03-07 02:51:35 UTC

HMDB ID

HMDB0014333

Secondary Accession Numbers

HMDB14333

Metabolite Identification

Common Name

Esmolol

Description

Esmolol (trade name Brevibloc) is a cardioselective beta1 receptor blocker with rapid onset, a very short duration of action, and no significant intrinsic sympathomimetic or membrane stabilising activity at therapeutic dosages. Esmolol decreases the force and rate of heart contractions by blocking beta-adrenergic receptors of the sympathetic nervous system, which are found in the heart and other organs of the body. Esmolol prevents the action of two naturally occurring substances: epinephrine and norepinephrine.

Structure

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

HMDB0243679
     RDKit          3D
(R)-Esmolol
 46 46  0  0  0  0  0  0  0  0999 V2000
   -8.6641   -0.3285   -0.8998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3058   -0.0116   -1.1651 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2904   -0.6701   -0.4918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6504   -1.5474    0.3466 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8403   -0.4108   -0.6943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3010    0.3581    0.4875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8549    0.6533    0.3719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4051    1.8097   -0.2376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0659    2.1006   -0.3432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1463    1.2203    0.1700 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1979    1.5257    0.0579 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1134    0.6019    0.6010 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5685    1.0559    0.4115 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6586    2.3189    1.0590 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4058    0.0757    1.1905 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3799   -1.2010    0.6343 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9820   -1.5124   -0.5851 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4952   -1.2647   -0.4423 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4687   -0.9661   -1.8466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5979    0.0712    0.7751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9288   -0.2471    0.8956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2876    0.1005   -1.7111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9728    0.1878    0.0428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7981   -1.4240   -0.8098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6901    0.2147   -1.6058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3361   -1.3771   -0.8324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9082    1.2989    0.5512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5294   -0.1956    1.4421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1154    2.5269   -0.6529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7673    3.0351   -0.8380 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0399   -0.3872    0.0892 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9826    0.4587    1.6942 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8458    1.2116   -0.6198 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0416    2.9318    0.5726 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8979    0.0193    2.2037 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4090    0.4827    1.4421 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6384   -1.9399    1.3552 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9472   -2.6494   -0.6718 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0721   -1.9349   -1.1163 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7671   -0.2378   -0.6890 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7771   -1.5682    0.5922 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9913   -0.0790   -2.2438 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3783   -0.7815   -1.8570 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6110   -1.7390   -2.6634 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1130   -0.6545    1.1951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3263   -1.1316    1.3613 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  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  2  0
 21  7  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  5 25  1  0
  5 26  1  0
  6 27  1  0
  6 28  1  0
  8 29  1  0
  9 30  1  0
 12 31  1  0
 12 32  1  0
 13 33  1  0
 14 34  1  0
 15 35  1  0
 15 36  1  0
 16 37  1  0
 17 38  1  0
 18 39  1  0
 18 40  1  0
 18 41  1  0
 19 42  1  0
 19 43  1  0
 19 44  1  0
 20 45  1  0
 21 46  1  0
M  END

187
  Mrv0541 02231214302D          

 21 21  0  0  1  0            999 V2000
    3.0790    1.0313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    2.6812    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -3.9188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -3.9188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079    3.5062    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934    2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079    2.6812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2223    3.9188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934    1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2223    4.7438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9369    3.5062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3644   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3644   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3644   -2.6812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3644   -3.5062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -4.7438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  9  1  0  0  0  0
  1 14  1  0  0  0  0
  2  6  1  0  0  0  0
  3 20  1  0  0  0  0
  3 21  1  0  0  0  0
  4 20  2  0  0  0  0
  5  7  1  0  0  0  0
  5  8  1  0  0  0  0
  6  7  1  0  0  0  0
  6  9  1  0  0  0  0
  8 10  1  0  0  0  0
  8 11  1  0  0  0  0
 12 13  1  0  0  0  0
 12 15  2  0  0  0  0
 12 16  1  0  0  0  0
 13 19  1  0  0  0  0
 14 17  2  0  0  0  0
 14 18  1  0  0  0  0
 15 17  1  0  0  0  0
 16 18  2  0  0  0  0
 19 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014333

> <DATABASE_NAME>
hmdb

> <SMILES>
COC(=O)CCC1=CC=C(OCC(O)CNC(C)C)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H25NO4/c1-12(2)17-10-14(18)11-21-15-7-4-13(5-8-15)6-9-16(19)20-3/h4-5,7-8,12,14,17-18H,6,9-11H2,1-3H3

> <INCHI_KEY>
AQNDDEOPVVGCPG-UHFFFAOYSA-N

> <FORMULA>
C16H25NO4

> <MOLECULAR_WEIGHT>
295.374

> <EXACT_MASS>
295.178358293

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
33.67622024849671

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 3-(4-{2-hydroxy-3-[(propan-2-yl)amino]propoxy}phenyl)propanoate

> <ALOGPS_LOGP>
2.02

> <JCHEM_LOGP>
1.8224301829999994

> <ALOGPS_LOGS>
-3.31

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.087971415863226

> <JCHEM_PKA_STRONGEST_BASIC>
9.666166605708492

> <JCHEM_POLAR_SURFACE_AREA>
67.78999999999999

> <JCHEM_REFRACTIVITY>
81.0532

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.44e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
esmolol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0243679
     RDKit          3D
(R)-Esmolol
 46 46  0  0  0  0  0  0  0  0999 V2000
   -8.6641   -0.3285   -0.8998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3058   -0.0116   -1.1651 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2904   -0.6701   -0.4918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6504   -1.5474    0.3466 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8403   -0.4108   -0.6943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3010    0.3581    0.4875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8549    0.6533    0.3719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4051    1.8097   -0.2376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0659    2.1006   -0.3432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1463    1.2203    0.1700 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1979    1.5257    0.0579 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1134    0.6019    0.6010 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5685    1.0559    0.4115 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6586    2.3189    1.0590 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4058    0.0757    1.1905 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3799   -1.2010    0.6343 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9820   -1.5124   -0.5851 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4952   -1.2647   -0.4423 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4687   -0.9661   -1.8466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5979    0.0712    0.7751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9288   -0.2471    0.8956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2876    0.1005   -1.7111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9728    0.1878    0.0428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7981   -1.4240   -0.8098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6901    0.2147   -1.6058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3361   -1.3771   -0.8324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9082    1.2989    0.5512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5294   -0.1956    1.4421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1154    2.5269   -0.6529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7673    3.0351   -0.8380 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0399   -0.3872    0.0892 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9826    0.4587    1.6942 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8458    1.2116   -0.6198 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0416    2.9318    0.5726 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8979    0.0193    2.2037 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4090    0.4827    1.4421 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6384   -1.9399    1.3552 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9472   -2.6494   -0.6718 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0721   -1.9349   -1.1163 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7671   -0.2378   -0.6890 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7771   -1.5682    0.5922 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9913   -0.0790   -2.2438 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3783   -0.7815   -1.8570 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6110   -1.7390   -2.6634 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1130   -0.6545    1.1951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3263   -1.1316    1.3613 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  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  2  0
 21  7  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  5 25  1  0
  5 26  1  0
  6 27  1  0
  6 28  1  0
  8 29  1  0
  9 30  1  0
 12 31  1  0
 12 32  1  0
 13 33  1  0
 14 34  1  0
 15 35  1  0
 15 36  1  0
 16 37  1  0
 17 38  1  0
 18 39  1  0
 18 40  1  0
 18 41  1  0
 19 42  1  0
 19 43  1  0
 19 44  1  0
 20 45  1  0
 21 46  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 187                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       5.747   1.925   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       5.747   5.005   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       3.080  -7.315   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       5.747  -7.315   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0       8.415   6.545   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       7.081   4.235   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.415   5.005   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.748   7.315   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.081   2.695   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.748   8.855   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.082   6.545   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.747  -2.695   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.747  -4.235   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.747   0.385   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.414  -1.925   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.081  -1.925   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.414  -0.385   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.081  -0.385   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.414  -5.005   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.414  -6.545   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.080  -8.855   0.000  0.00  0.00           C+0
CONECT    1    9   14                                                       
CONECT    2    6                                                            
CONECT    3   20   21                                                       
CONECT    4   20                                                            
CONECT    5    7    8                                                       
CONECT    6    2    7    9                                                  
CONECT    7    5    6                                                       
CONECT    8    5   10   11                                                  
CONECT    9    1    6                                                       
CONECT   10    8                                                            
CONECT   11    8                                                            
CONECT   12   13   15   16                                                  
CONECT   13   12   19                                                       
CONECT   14    1   17   18                                                  
CONECT   15   12   17                                                       
CONECT   16   12   18                                                       
CONECT   17   14   15                                                       
CONECT   18   14   16                                                       
CONECT   19   13   20                                                       
CONECT   20    3    4   19                                                  
CONECT   21    3                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   42    0
END

COMPND    HMDB0243679
HETATM    1  C1  UNL     1      -8.664  -0.329  -0.900  1.00  0.00           C  
HETATM    2  O1  UNL     1      -7.306  -0.012  -1.165  1.00  0.00           O  
HETATM    3  C2  UNL     1      -6.290  -0.670  -0.492  1.00  0.00           C  
HETATM    4  O2  UNL     1      -6.650  -1.547   0.347  1.00  0.00           O  
HETATM    5  C3  UNL     1      -4.840  -0.411  -0.694  1.00  0.00           C  
HETATM    6  C4  UNL     1      -4.301   0.358   0.487  1.00  0.00           C  
HETATM    7  C5  UNL     1      -2.855   0.653   0.372  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.405   1.810  -0.238  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.066   2.101  -0.343  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.146   1.220   0.170  1.00  0.00           C  
HETATM   11  O3  UNL     1       1.198   1.526   0.058  1.00  0.00           O  
HETATM   12  C9  UNL     1       2.113   0.602   0.601  1.00  0.00           C  
HETATM   13  C10 UNL     1       3.569   1.056   0.412  1.00  0.00           C  
HETATM   14  O4  UNL     1       3.659   2.319   1.059  1.00  0.00           O  
HETATM   15  C11 UNL     1       4.406   0.076   1.191  1.00  0.00           C  
HETATM   16  N1  UNL     1       4.380  -1.201   0.634  1.00  0.00           N  
HETATM   17  C12 UNL     1       4.982  -1.512  -0.585  1.00  0.00           C  
HETATM   18  C13 UNL     1       6.495  -1.265  -0.442  1.00  0.00           C  
HETATM   19  C14 UNL     1       4.469  -0.966  -1.847  1.00  0.00           C  
HETATM   20  C15 UNL     1      -0.598   0.071   0.775  1.00  0.00           C  
HETATM   21  C16 UNL     1      -1.929  -0.247   0.896  1.00  0.00           C  
HETATM   22  H1  UNL     1      -9.288   0.101  -1.711  1.00  0.00           H  
HETATM   23  H2  UNL     1      -8.973   0.188   0.043  1.00  0.00           H  
HETATM   24  H3  UNL     1      -8.798  -1.424  -0.810  1.00  0.00           H  
HETATM   25  H4  UNL     1      -4.690   0.215  -1.606  1.00  0.00           H  
HETATM   26  H5  UNL     1      -4.336  -1.377  -0.832  1.00  0.00           H  
HETATM   27  H6  UNL     1      -4.908   1.299   0.551  1.00  0.00           H  
HETATM   28  H7  UNL     1      -4.529  -0.196   1.442  1.00  0.00           H  
HETATM   29  H8  UNL     1      -3.115   2.527  -0.653  1.00  0.00           H  
HETATM   30  H9  UNL     1      -0.767   3.035  -0.838  1.00  0.00           H  
HETATM   31  H10 UNL     1       2.040  -0.387   0.089  1.00  0.00           H  
HETATM   32  H11 UNL     1       1.983   0.459   1.694  1.00  0.00           H  
HETATM   33  H12 UNL     1       3.846   1.212  -0.620  1.00  0.00           H  
HETATM   34  H13 UNL     1       3.042   2.932   0.573  1.00  0.00           H  
HETATM   35  H14 UNL     1       3.898   0.019   2.204  1.00  0.00           H  
HETATM   36  H15 UNL     1       5.409   0.483   1.442  1.00  0.00           H  
HETATM   37  H16 UNL     1       4.638  -1.940   1.355  1.00  0.00           H  
HETATM   38  H17 UNL     1       4.947  -2.649  -0.672  1.00  0.00           H  
HETATM   39  H18 UNL     1       7.072  -1.935  -1.116  1.00  0.00           H  
HETATM   40  H19 UNL     1       6.767  -0.238  -0.689  1.00  0.00           H  
HETATM   41  H20 UNL     1       6.777  -1.568   0.592  1.00  0.00           H  
HETATM   42  H21 UNL     1       4.991  -0.079  -2.244  1.00  0.00           H  
HETATM   43  H22 UNL     1       3.378  -0.781  -1.857  1.00  0.00           H  
HETATM   44  H23 UNL     1       4.611  -1.739  -2.663  1.00  0.00           H  
HETATM   45  H24 UNL     1       0.113  -0.654   1.195  1.00  0.00           H  
HETATM   46  H25 UNL     1      -2.326  -1.132   1.361  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3
CONECT    3    4    4    5
CONECT    5    6   25   26
CONECT    6    7   27   28
CONECT    7    8    8   21
CONECT    8    9   29
CONECT    9   10   10   30
CONECT   10   11   20
CONECT   11   12
CONECT   12   13   31   32
CONECT   13   14   15   33
CONECT   14   34
CONECT   15   16   35   36
CONECT   16   17   37
CONECT   17   18   19   38
CONECT   18   39   40   41
CONECT   19   42   43   44
CONECT   20   21   21   45
CONECT   21   46
END

HMDB0243679
     RDKit          3D
(R)-Esmolol
 46 46  0  0  0  0  0  0  0  0999 V2000
   -8.6641   -0.3285   -0.8998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3058   -0.0116   -1.1651 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2904   -0.6701   -0.4918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6504   -1.5474    0.3466 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8403   -0.4108   -0.6943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3010    0.3581    0.4875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8549    0.6533    0.3719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4051    1.8097   -0.2376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0659    2.1006   -0.3432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1463    1.2203    0.1700 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1979    1.5257    0.0579 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1134    0.6019    0.6010 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5685    1.0559    0.4115 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6586    2.3189    1.0590 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4058    0.0757    1.1905 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3799   -1.2010    0.6343 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9820   -1.5124   -0.5851 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4952   -1.2647   -0.4423 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4687   -0.9661   -1.8466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5979    0.0712    0.7751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9288   -0.2471    0.8956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2876    0.1005   -1.7111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9728    0.1878    0.0428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7981   -1.4240   -0.8098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6901    0.2147   -1.6058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3361   -1.3771   -0.8324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9082    1.2989    0.5512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5294   -0.1956    1.4421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1154    2.5269   -0.6529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7673    3.0351   -0.8380 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0399   -0.3872    0.0892 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9826    0.4587    1.6942 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8458    1.2116   -0.6198 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0416    2.9318    0.5726 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8979    0.0193    2.2037 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4090    0.4827    1.4421 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6384   -1.9399    1.3552 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9472   -2.6494   -0.6718 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0721   -1.9349   -1.1163 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7671   -0.2378   -0.6890 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7771   -1.5682    0.5922 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9913   -0.0790   -2.2438 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3783   -0.7815   -1.8570 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6110   -1.7390   -2.6634 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1130   -0.6545    1.1951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3263   -1.1316    1.3613 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  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  2  0
 21  7  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  5 25  1  0
  5 26  1  0
  6 27  1  0
  6 28  1  0
  8 29  1  0
  9 30  1  0
 12 31  1  0
 12 32  1  0
 13 33  1  0
 14 34  1  0
 15 35  1  0
 15 36  1  0
 16 37  1  0
 17 38  1  0
 18 39  1  0
 18 40  1  0
 18 41  1  0
 19 42  1  0
 19 43  1  0
 19 44  1  0
 20 45  1  0
 21 46  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Brevibloc	HMDB
Esmolol hydrochloride	HMDB

Chemical Formula

C₁₆H₂₅NO₄

Average Molecular Weight

295.374

Monoisotopic Molecular Weight

295.178358293

IUPAC Name

methyl 3-(4-{2-hydroxy-3-[(propan-2-yl)amino]propoxy}phenyl)propanoate

Traditional Name

esmolol

CAS Registry Number

103598-03-4

SMILES

COC(=O)CCC1=CC=C(OCC(O)CNC(C)C)C=C1

InChI Identifier

InChI=1S/C16H25NO4/c1-12(2)17-10-14(18)11-21-15-7-4-13(5-8-15)6-9-16(19)20-3/h4-5,7-8,12,14,17-18H,6,9-11H2,1-3H3

InChI Key

AQNDDEOPVVGCPG-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenol ethers. These are aromatic compounds containing an ether group substituted with a benzene ring.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenol ethers

Sub Class

Not Available

Direct Parent

Phenol ethers

Alternative Parents

Substituents

Phenoxy compound
Phenol ether
Alkyl aryl ether
Fatty acid ester
Monocyclic benzene moiety
Fatty acyl
Methyl ester
1,2-aminoalcohol
Secondary alcohol
Amino acid or derivatives
Carboxylic acid ester
Secondary amine
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Secondary aliphatic amine
Ether
Hydrocarbon derivative
Organopnictogen compound
Organonitrogen compound
Organooxygen compound
Carbonyl group
Organic oxygen compound
Organic oxide
Amine
Organic nitrogen compound
Alcohol
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

aromatic ether (CHEBI:4856 )
secondary alcohol (CHEBI:4856 )
secondary amino compound (CHEBI:4856 )
methyl ester (CHEBI:4856 )
ethanolamines (CHEBI:4856 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0014333)

Source

Exogenous

Exogenous (HMDB: HMDB0014333)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Esmolol Action Pathway (PathBank: SMP0000301)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.14 g/L	Not Available
LogP	1.7	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.14 g/L	ALOGPS
logP	2.02	ALOGPS
logP	1.82	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	14.09	ChemAxon
pKa (Strongest Basic)	9.67	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	67.79 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	81.05 m³·mol⁻¹	ChemAxon
Polarizability	33.68 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]+	170.945	31661259
DarkChem	[M-H]-	170.332	31661259
DeepCCS	[M+H]+	171.444	30932474
DeepCCS	[M-H]-	169.086	30932474
DeepCCS	[M-2H]-	201.972	30932474
DeepCCS	[M+Na]+	177.537	30932474
AllCCS	[M+H]+	173.5	32859911
AllCCS	[M+H-H2O]+	170.5	32859911
AllCCS	[M+NH4]+	176.3	32859911
AllCCS	[M+Na]+	177.1	32859911
AllCCS	[M-H]-	174.0	32859911
AllCCS	[M+Na-2H]-	174.8	32859911
AllCCS	[M+HCOO]-	175.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Esmolol	COC(=O)CCC1=CC=C(OCC(O)CNC(C)C)C=C1	3107.9	Standard polar	33892256
Esmolol	COC(=O)CCC1=CC=C(OCC(O)CNC(C)C)C=C1	2243.6	Standard non polar	33892256
Esmolol	COC(=O)CCC1=CC=C(OCC(O)CNC(C)C)C=C1	2264.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Esmolol,1TMS,isomer #1	COC(=O)CCC1=CC=C(OCC(CNC(C)C)O[Si](C)(C)C)C=C1	2274.3	Semi standard non polar	33892256
Esmolol,1TMS,isomer #2	COC(=O)CCC1=CC=C(OCC(O)CN(C(C)C)[Si](C)(C)C)C=C1	2404.3	Semi standard non polar	33892256
Esmolol,2TMS,isomer #1	COC(=O)CCC1=CC=C(OCC(CN(C(C)C)[Si](C)(C)C)O[Si](C)(C)C)C=C1	2458.8	Semi standard non polar	33892256
Esmolol,2TMS,isomer #1	COC(=O)CCC1=CC=C(OCC(CN(C(C)C)[Si](C)(C)C)O[Si](C)(C)C)C=C1	2477.4	Standard non polar	33892256
Esmolol,2TMS,isomer #1	COC(=O)CCC1=CC=C(OCC(CN(C(C)C)[Si](C)(C)C)O[Si](C)(C)C)C=C1	2797.9	Standard polar	33892256
Esmolol,1TBDMS,isomer #1	COC(=O)CCC1=CC=C(OCC(CNC(C)C)O[Si](C)(C)C(C)(C)C)C=C1	2508.3	Semi standard non polar	33892256
Esmolol,1TBDMS,isomer #2	COC(=O)CCC1=CC=C(OCC(O)CN(C(C)C)[Si](C)(C)C(C)(C)C)C=C1	2664.1	Semi standard non polar	33892256
Esmolol,2TBDMS,isomer #1	COC(=O)CCC1=CC=C(OCC(CN(C(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C=C1	2921.6	Semi standard non polar	33892256
Esmolol,2TBDMS,isomer #1	COC(=O)CCC1=CC=C(OCC(CN(C(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C=C1	2884.5	Standard non polar	33892256
Esmolol,2TBDMS,isomer #1	COC(=O)CCC1=CC=C(OCC(CN(C(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C=C1	2985.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Esmolol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fk9-9630000000-d551ff7db097920ee10a	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Esmolol GC-MS (1 TMS) - 70eV, Positive	splash10-006x-4912000000-8428bd5b9c71bba4b8e3	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Esmolol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Esmolol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Esmolol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Esmolol GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Esmolol GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Esmolol GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Esmolol , positive-QTOF	splash10-0002-0490000000-55cd388bbf570d69d195	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Esmolol 35V, Positive-QTOF	splash10-0002-2790000000-6706374761e30b94ee80	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Esmolol 10V, Positive-QTOF	splash10-01ot-1190000000-7d08c97e98a5d306d8da	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Esmolol 20V, Positive-QTOF	splash10-00di-8590000000-da4f55d9275617bd6402	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Esmolol 40V, Positive-QTOF	splash10-05fr-9500000000-08aa89fd1914ce6a579d	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Esmolol 10V, Negative-QTOF	splash10-0006-1590000000-c5f36e8382810e69c6aa	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Esmolol 20V, Negative-QTOF	splash10-01r2-1900000000-6a2e2bd7c87493c461a3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Esmolol 40V, Negative-QTOF	splash10-0002-2900000000-fc3c798f1e113b4150cc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Esmolol 10V, Negative-QTOF	splash10-0006-0390000000-1773723453dc96f5b346	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Esmolol 20V, Negative-QTOF	splash10-02u4-2910000000-c1491f7c9453e0749da0	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Esmolol 40V, Negative-QTOF	splash10-014i-0900000000-01422e7fd5494fac871d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Esmolol 10V, Positive-QTOF	splash10-01ot-0090000000-bd4de0fe533de344ee51	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Esmolol 20V, Positive-QTOF	splash10-00dj-9560000000-c9cf7efcc6b351e9a679	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Esmolol 40V, Positive-QTOF	splash10-0ab9-9200000000-3eca3647d51aee83826b	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Esmolol 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 DB00187	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00187	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00187

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

53916

KEGG Compound ID

C06980

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Esmolol

METLIN ID

Not Available

PubChem Compound

59768

PDB ID

Not Available

ChEBI ID

88206

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. Beta-1 adrenergic receptor

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

References

Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Jahn P, Eckrich B, Schneidrowski B, Volz-Zang C, Schulte B, Mutschler E, Palm D: Beta 1-adrenoceptor subtype selective antagonism of esmolol and its major metabolite in vitro and in man. Investigations using tricresylphosphate as red blood cell carboxylesterase inhibitor. Arzneimittelforschung. 1995 May;45(5):536-41. [PubMed:7612051 ]
Volz-Zang C, Eckrich B, Jahn P, Schneidrowski B, Schulte B, Palm D: Esmolol, an ultrashort-acting, selective beta 1-adrenoceptor antagonist: pharmacodynamic and pharmacokinetic properties. Eur J Clin Pharmacol. 1994;46(5):399-404. [PubMed:7957532 ]
Kirshenbaum JM: Nonthrombolytic intervention in acute myocardial infarction. Am J Cardiol. 1989 Jul 18;64(4):25B-28B. [PubMed:2568748 ]
Jacobs JR, Maier GW, Rankin JS, Reves JG: Esmolol and left ventricular function in the awake dog. Anesthesiology. 1988 Mar;68(3):373-8. [PubMed:2894187 ]
Howie MB, Black HA, Zvara D, McSweeney TD, Martin DJ, Coffman JA: Esmolol reduces autonomic hypersensitivity and length of seizures induced by electroconvulsive therapy. Anesth Analg. 1990 Oct;71(4):384-8. [PubMed:1975995 ]

Showing metabocard for Esmolol (HMDB0014333)

MOL for HMDB0014333 (Esmolol)

3D MOL for HMDB0014333 (Esmolol)

3D SDF for HMDB0014333 (Esmolol)

3D-SDF for HMDB0014333 (Esmolol)

PDB for HMDB0014333 (Esmolol)

3D PDB for HMDB0014333 (Esmolol)

SMILES for HMDB0014333 (Esmolol)

INCHI for HMDB0014333 (Esmolol)

Structure for HMDB0014333 (Esmolol)

3D Structure for HMDB0014333 (Esmolol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References