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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-05-18 08:50:34 UTC

Update Date

2022-03-07 02:49:11 UTC

HMDB ID

HMDB0001932

Secondary Accession Numbers

HMDB01932

Metabolite Identification

Common Name

Metoprolol

Description

Metoprolol is a selective beta1 receptor blocker used in treatment of several diseases of the cardiovascular system. It is marketed under the brand name Lopressor by Novartis, and Toprol (in the USA); Seleken or Selokeen (elsewhere); A selective adrenergic beta-1-blocking agent with no stimulatory action. It's binding to plasma albumin is weaker than alprenolol and it may be useful in the treatment of several diseases of the cardiovascular system; Metoprolol is a selective beta1 receptor blocker used in treatment of several diseases of the cardiovascular system. It is marketed under the brand name Lopressor by Novartis, and Toprol (in the USA); Seleken or Selokeen (elsewhere); as Minax by Alphapharm (in Australia), as Betaloc by AstraZeneca and as Corvitol by Berlin-Chemie AG; A selective adrenergic beta-1-blocking agent with no stimulatory action. It's binding to plasma albumin is weaker than alprenolol and it may be useful in angina pectoris, hypertension, or cardiac arrhythmias; as Minax by Alphapharm (in Australia), as Betaloc by AstraZeneca and as Corvitol by Berlin-Chemie AG.

Structure

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

HMDB0243688
     RDKit          3D
(R)-Metoprolol
 44 44  0  0  0  0  0  0  0  0999 V2000
    7.0359    0.6727   -1.3012 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6606   -0.3548   -0.4837 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4469   -0.1554    0.1311 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3488   -0.0349   -0.8828 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0268    0.1536   -0.1997 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3540   -0.9720    0.1894 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1156   -0.8291    0.8140 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5757    0.4187    1.0355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6230    0.6027    1.6351 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5927   -0.1623    2.1624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3471   -1.1364    1.3363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2959   -1.7433    2.2188 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0810   -0.5416    0.1608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9934    0.4913    0.5236 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8033    0.9175   -0.5855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6881   -0.2790   -0.9870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0049    1.3582   -1.8004 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3054    1.5623    0.6160 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5244    1.4193    0.0025 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3841    0.9230   -2.1450 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2439    1.5862   -0.6839 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0350    0.4432   -1.7720 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4422    0.8090    0.7270 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2476   -1.0074    0.8529 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5144    0.8607   -1.5376 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3087   -0.9353   -1.5203 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7403   -1.9806    0.0371 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5741   -1.7098    1.1431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2838    0.5020    2.7663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1225   -0.7896    2.9963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7110   -1.9410    0.9760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8279   -2.5392    2.6308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6817   -1.3985   -0.2589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3583   -0.1478   -0.5746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6626    0.2146    1.2784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4814    1.7573   -0.3424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1221   -0.8725   -1.7153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6404    0.0424   -1.4368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7984   -0.8877   -0.0673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3087    0.6154   -2.1784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7893    1.4687   -2.6179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5840    2.3650   -1.6329 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8372    2.5261    0.8112 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0796    2.3097   -0.3212 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  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
  8 18  1  0
 18 19  2  0
 19  5  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  6 27  1  0
  7 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  0
 12 32  1  0
 13 33  1  0
 13 34  1  0
 14 35  1  0
 15 36  1  0
 16 37  1  0
 16 38  1  0
 16 39  1  0
 17 40  1  0
 17 41  1  0
 17 42  1  0
 18 43  1  0
 19 44  1  0
M  END

264
  Mrv1652305271900212D          

 19 19  0  0  1  0            999 V2000
    3.0791    0.6188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    2.2688    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -3.9188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    3.0938    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    3.5063    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
    5.9370    3.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    4.3313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -3.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -4.3313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  8  1  0  0  0  0
  1 11  1  0  0  0  0
  2  5  1  0  0  0  0
  3 18  1  0  0  0  0
  3 19  1  0  0  0  0
  4  6  1  0  0  0  0
  4  7  1  0  0  0  0
  5  6  1  0  0  0  0
  5  8  1  0  0  0  0
  7  9  1  0  0  0  0
  7 10  1  0  0  0  0
 11 14  2  0  0  0  0
 11 15  1  0  0  0  0
 12 13  1  0  0  0  0
 12 16  2  0  0  0  0
 12 17  1  0  0  0  0
 13 18  1  0  0  0  0
 14 16  1  0  0  0  0
 15 17  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001932

> <DATABASE_NAME>
hmdb

> <SMILES>
COCCC1=CC=C(OCC(O)CNC(C)C)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H25NO3/c1-12(2)16-10-14(17)11-19-15-6-4-13(5-7-15)8-9-18-3/h4-7,12,14,16-17H,8-11H2,1-3H3

> <INCHI_KEY>
IUBSYMUCCVWXPE-UHFFFAOYSA-N

> <FORMULA>
C15H25NO3

> <MOLECULAR_WEIGHT>
267.3639

> <EXACT_MASS>
267.183443671

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
31.895891074262103

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-[4-(2-methoxyethyl)phenoxy]-3-[(propan-2-yl)amino]propan-2-ol

> <ALOGPS_LOGP>
1.80

> <JCHEM_LOGP>
1.758657114

> <ALOGPS_LOGS>
-2.82

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.087971415863102

> <JCHEM_PKA_STRONGEST_BASIC>
9.666166605708499

> <JCHEM_POLAR_SURFACE_AREA>
50.72

> <JCHEM_REFRACTIVITY>
76.69760000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.02e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
metoprolol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0243688
     RDKit          3D
(R)-Metoprolol
 44 44  0  0  0  0  0  0  0  0999 V2000
    7.0359    0.6727   -1.3012 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6606   -0.3548   -0.4837 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4469   -0.1554    0.1311 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3488   -0.0349   -0.8828 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0268    0.1536   -0.1997 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3540   -0.9720    0.1894 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1156   -0.8291    0.8140 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5757    0.4187    1.0355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6230    0.6027    1.6351 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5927   -0.1623    2.1624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3471   -1.1364    1.3363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2959   -1.7433    2.2188 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0810   -0.5416    0.1608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9934    0.4913    0.5236 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8033    0.9175   -0.5855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6881   -0.2790   -0.9870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0049    1.3582   -1.8004 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3054    1.5623    0.6160 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5244    1.4193    0.0025 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3841    0.9230   -2.1450 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2439    1.5862   -0.6839 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0350    0.4432   -1.7720 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4422    0.8090    0.7270 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2476   -1.0074    0.8529 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5144    0.8607   -1.5376 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3087   -0.9353   -1.5203 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7403   -1.9806    0.0371 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5741   -1.7098    1.1431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2838    0.5020    2.7663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1225   -0.7896    2.9963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7110   -1.9410    0.9760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8279   -2.5392    2.6308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6817   -1.3985   -0.2589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3583   -0.1478   -0.5746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6626    0.2146    1.2784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4814    1.7573   -0.3424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1221   -0.8725   -1.7153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6404    0.0424   -1.4368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7984   -0.8877   -0.0673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3087    0.6154   -2.1784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7893    1.4687   -2.6179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5840    2.3650   -1.6329 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8372    2.5261    0.8112 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0796    2.3097   -0.3212 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  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
  8 18  1  0
 18 19  2  0
 19  5  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  6 27  1  0
  7 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  0
 12 32  1  0
 13 33  1  0
 13 34  1  0
 14 35  1  0
 15 36  1  0
 16 37  1  0
 16 38  1  0
 16 39  1  0
 17 40  1  0
 17 41  1  0
 17 42  1  0
 18 43  1  0
 19 44  1  0
M  END

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 264                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  O   UNK     0       5.748   1.155   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       5.748   4.235   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       4.414  -7.315   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       8.415   5.775   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       7.081   3.465   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.415   4.235   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.748   6.545   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      11.082   5.775   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.748   8.085   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.748  -0.385   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.748  -3.465   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.748  -5.005   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.414  -1.155   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.081  -1.155   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.414  -2.695   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.081  -2.695   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.414  -5.775   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.080  -8.085   0.000  0.00  0.00           C+0
CONECT    1    8   11                                                       
CONECT    2    5                                                            
CONECT    3   18   19                                                       
CONECT    4    6    7                                                       
CONECT    5    2    6    8                                                  
CONECT    6    4    5                                                       
CONECT    7    4    9   10                                                  
CONECT    8    1    5                                                       
CONECT    9    7                                                            
CONECT   10    7                                                            
CONECT   11    1   14   15                                                  
CONECT   12   13   16   17                                                  
CONECT   13   12   18                                                       
CONECT   14   11   16                                                       
CONECT   15   11   17                                                       
CONECT   16   12   14                                                       
CONECT   17   12   15                                                       
CONECT   18    3   13                                                       
CONECT   19    3                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   38    0
END

COMPND    HMDB0243736
HETATM    1  C1  UNL     1       6.550  -0.470   2.452  1.00  0.00           C  
HETATM    2  O1  UNL     1       6.149  -1.534   1.667  1.00  0.00           O  
HETATM    3  C2  UNL     1       4.929  -1.278   1.109  1.00  0.00           C  
HETATM    4  C3  UNL     1       4.860  -0.068   0.210  1.00  0.00           C  
HETATM    5  C4  UNL     1       3.436  -0.024  -0.279  1.00  0.00           C  
HETATM    6  C5  UNL     1       3.050  -0.668  -1.432  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.766  -0.654  -1.908  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.793   0.029  -1.221  1.00  0.00           C  
HETATM    9  O2  UNL     1      -0.507   0.083  -1.642  1.00  0.00           O  
HETATM   10  C8  UNL     1      -1.458   0.804  -0.887  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.772   0.661  -1.623  1.00  0.00           C  
HETATM   12  O3  UNL     1      -2.538   1.218  -2.906  1.00  0.00           O  
HETATM   13  C10 UNL     1      -3.837   1.476  -0.950  1.00  0.00           C  
HETATM   14  N1  UNL     1      -4.143   1.037   0.338  1.00  0.00           N  
HETATM   15  C11 UNL     1      -4.811  -0.169   0.596  1.00  0.00           C  
HETATM   16  C12 UNL     1      -4.109  -1.445   0.236  1.00  0.00           C  
HETATM   17  C13 UNL     1      -5.163  -0.166   2.100  1.00  0.00           C  
HETATM   18  C14 UNL     1       1.159   0.681  -0.063  1.00  0.00           C  
HETATM   19  C15 UNL     1       2.462   0.663   0.413  1.00  0.00           C  
HETATM   20  H1  UNL     1       6.640   0.425   1.813  1.00  0.00           H  
HETATM   21  H2  UNL     1       5.768  -0.229   3.227  1.00  0.00           H  
HETATM   22  H3  UNL     1       7.524  -0.686   2.978  1.00  0.00           H  
HETATM   23  H4  UNL     1       4.529  -2.151   0.528  1.00  0.00           H  
HETATM   24  H5  UNL     1       4.128  -1.108   1.892  1.00  0.00           H  
HETATM   25  H6  UNL     1       5.543  -0.110  -0.651  1.00  0.00           H  
HETATM   26  H7  UNL     1       4.991   0.865   0.814  1.00  0.00           H  
HETATM   27  H8  UNL     1       3.852  -1.208  -1.961  1.00  0.00           H  
HETATM   28  H9  UNL     1       1.518  -1.173  -2.812  1.00  0.00           H  
HETATM   29  H10 UNL     1      -1.203   1.893  -0.839  1.00  0.00           H  
HETATM   30  H11 UNL     1      -1.478   0.462   0.150  1.00  0.00           H  
HETATM   31  H12 UNL     1      -3.004  -0.391  -1.783  1.00  0.00           H  
HETATM   32  H13 UNL     1      -1.610   0.987  -3.181  1.00  0.00           H  
HETATM   33  H14 UNL     1      -4.737   1.506  -1.645  1.00  0.00           H  
HETATM   34  H15 UNL     1      -3.512   2.556  -0.947  1.00  0.00           H  
HETATM   35  H16 UNL     1      -4.390   1.767   1.023  1.00  0.00           H  
HETATM   36  H17 UNL     1      -5.820  -0.215   0.054  1.00  0.00           H  
HETATM   37  H18 UNL     1      -4.479  -1.821  -0.733  1.00  0.00           H  
HETATM   38  H19 UNL     1      -3.015  -1.349   0.326  1.00  0.00           H  
HETATM   39  H20 UNL     1      -4.433  -2.249   0.966  1.00  0.00           H  
HETATM   40  H21 UNL     1      -5.867  -0.984   2.319  1.00  0.00           H  
HETATM   41  H22 UNL     1      -4.225  -0.185   2.667  1.00  0.00           H  
HETATM   42  H23 UNL     1      -5.681   0.801   2.287  1.00  0.00           H  
HETATM   43  H24 UNL     1       0.403   1.235   0.505  1.00  0.00           H  
HETATM   44  H25 UNL     1       2.743   1.188   1.340  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3
CONECT    3    4   23   24
CONECT    4    5   25   26
CONECT    5    6    6   19
CONECT    6    7   27
CONECT    7    8    8   28
CONECT    8    9   18
CONECT    9   10
CONECT   10   11   29   30
CONECT   11   12   13   31
CONECT   12   32
CONECT   13   14   33   34
CONECT   14   15   35
CONECT   15   16   17   36
CONECT   16   37   38   39
CONECT   17   40   41   42
CONECT   18   19   19   43
CONECT   19   44
END

HMDB0243688
     RDKit          3D
(R)-Metoprolol
 44 44  0  0  0  0  0  0  0  0999 V2000
    7.0359    0.6727   -1.3012 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6606   -0.3548   -0.4837 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4469   -0.1554    0.1311 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3488   -0.0349   -0.8828 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0268    0.1536   -0.1997 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3540   -0.9720    0.1894 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1156   -0.8291    0.8140 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5757    0.4187    1.0355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6230    0.6027    1.6351 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5927   -0.1623    2.1624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3471   -1.1364    1.3363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2959   -1.7433    2.2188 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0810   -0.5416    0.1608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9934    0.4913    0.5236 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8033    0.9175   -0.5855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6881   -0.2790   -0.9870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0049    1.3582   -1.8004 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3054    1.5623    0.6160 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5244    1.4193    0.0025 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3841    0.9230   -2.1450 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2439    1.5862   -0.6839 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0350    0.4432   -1.7720 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4422    0.8090    0.7270 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2476   -1.0074    0.8529 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5144    0.8607   -1.5376 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3087   -0.9353   -1.5203 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7403   -1.9806    0.0371 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5741   -1.7098    1.1431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2838    0.5020    2.7663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1225   -0.7896    2.9963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7110   -1.9410    0.9760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8279   -2.5392    2.6308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6817   -1.3985   -0.2589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3583   -0.1478   -0.5746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6626    0.2146    1.2784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4814    1.7573   -0.3424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1221   -0.8725   -1.7153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6404    0.0424   -1.4368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7984   -0.8877   -0.0673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3087    0.6154   -2.1784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7893    1.4687   -2.6179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5840    2.3650   -1.6329 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8372    2.5261    0.8112 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0796    2.3097   -0.3212 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  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
  8 18  1  0
 18 19  2  0
 19  5  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  6 27  1  0
  7 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  0
 12 32  1  0
 13 33  1  0
 13 34  1  0
 14 35  1  0
 15 36  1  0
 16 37  1  0
 16 38  1  0
 16 39  1  0
 17 40  1  0
 17 41  1  0
 17 42  1  0
 18 43  1  0
 19 44  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(RS)-Metoprolol	ChEBI
1-(Isopropylamino)-3-[4-(2-methoxyethyl)phenoxy]propan-2-ol	ChEBI
(+/-)-metoprolol	HMDB
Beatrolol	HMDB
DL-Metoprolol	HMDB
Lopresor	HMDB
Lopresoretic	HMDB
Lopressor	HMDB, MeSH
Meijoprolol	HMDB
Metohexal	HMDB
Metoprolol succinate	HMDB, MeSH
Metoprolol tartrate	HMDB, MeSH
Metoprololum	HMDB
Preblok	HMDB
Presolol	HMDB
Seloken	HMDB, MeSH
Seroken	HMDB
Spesicor	HMDB, MeSH
Toprol-XL	HMDB, MeSH
Beloc duriles	MeSH, HMDB
Beloc-duriles	MeSH, HMDB
Betaloc	MeSH, HMDB
Succinate, metoprolol	MeSH, HMDB
Toprol	MeSH, HMDB
BelocDuriles	MeSH, HMDB
Betaloc astra	MeSH, HMDB
CR-XL, Metoprolol	MeSH, HMDB
Spesikor	MeSH, HMDB
Tartrate, metoprolol	MeSH, HMDB
Toprol XL	MeSH, HMDB
Metoprolol CR-XL	MeSH, HMDB
Betaloc-astra	MeSH, HMDB
Betalok	MeSH, HMDB
Metoprolol CR XL	MeSH, HMDB
ToprolXL	MeSH, HMDB
BetalocAstra	MeSH, HMDB

Chemical Formula

C₁₅H₂₅NO₃

Average Molecular Weight

267.3639

Monoisotopic Molecular Weight

267.183443671

IUPAC Name

1-[4-(2-methoxyethyl)phenoxy]-3-[(propan-2-yl)amino]propan-2-ol

Traditional Name

metoprolol

CAS Registry Number

37350-58-6

SMILES

COCCC1=CC=C(OCC(O)CNC(C)C)C=C1

InChI Identifier

InChI=1S/C15H25NO3/c1-12(2)16-10-14(17)11-19-15-6-4-13(5-7-15)8-9-18-3/h4-7,12,14,16-17H,8-11H2,1-3H3

InChI Key

IUBSYMUCCVWXPE-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tyrosols and derivatives. Tyrosols and derivatives are compounds containing a hydroxyethyl group attached to the C4 carbon of a phenol group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenols

Sub Class

Tyrosols and derivatives

Direct Parent

Tyrosols and derivatives

Alternative Parents

Substituents

Tyrosol derivative
Phenoxy compound
Phenol ether
Alkyl aryl ether
Monocyclic benzene moiety
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

aromatic ether (CHEBI:6904 )
secondary alcohol (CHEBI:6904 )
secondary amino compound (CHEBI:6904 )
propanolamine (CHEBI:6904 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

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	Not Available	Not Available
LogP	1.88	HANSCH,C ET AL. (1995)

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	172.7	30932474
[M+H]+	Not Available	170.692	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000730

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.4 g/L	ALOGPS
logP	1.8	ALOGPS
logP	1.76	ChemAxon
logS	-2.8	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	50.72 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	76.7 m³·mol⁻¹	ChemAxon
Polarizability	31.9 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]+	163.92	31661259
DarkChem	[M-H]-	164.146	31661259
AllCCS	[M+H]+	166.873	32859911
AllCCS	[M-H]-	168.408	32859911
DeepCCS	[M+H]+	166.877	30932474
DeepCCS	[M-H]-	164.519	30932474
DeepCCS	[M-2H]-	197.405	30932474
DeepCCS	[M+Na]+	172.97	30932474
AllCCS	[M+H]+	166.9	32859911
AllCCS	[M+H-H2O]+	163.6	32859911
AllCCS	[M+NH4]+	169.9	32859911
AllCCS	[M+Na]+	170.7	32859911
AllCCS	[M-H]-	168.4	32859911
AllCCS	[M+Na-2H]-	169.2	32859911
AllCCS	[M+HCOO]-	170.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Metoprolol	COCCC1=CC=C(OCC(O)CNC(C)C)C=C1	2639.5	Standard polar	33892256
Metoprolol	COCCC1=CC=C(OCC(O)CNC(C)C)C=C1	2011.3	Standard non polar	33892256
Metoprolol	COCCC1=CC=C(OCC(O)CNC(C)C)C=C1	2028.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Metoprolol,1TMS,isomer #1	COCCC1=CC=C(OCC(CNC(C)C)O[Si](C)(C)C)C=C1	2063.1	Semi standard non polar	33892256
Metoprolol,1TMS,isomer #2	COCCC1=CC=C(OCC(O)CN(C(C)C)[Si](C)(C)C)C=C1	2204.3	Semi standard non polar	33892256
Metoprolol,2TMS,isomer #1	COCCC1=CC=C(OCC(CN(C(C)C)[Si](C)(C)C)O[Si](C)(C)C)C=C1	2253.9	Semi standard non polar	33892256
Metoprolol,2TMS,isomer #1	COCCC1=CC=C(OCC(CN(C(C)C)[Si](C)(C)C)O[Si](C)(C)C)C=C1	2252.4	Standard non polar	33892256
Metoprolol,2TMS,isomer #1	COCCC1=CC=C(OCC(CN(C(C)C)[Si](C)(C)C)O[Si](C)(C)C)C=C1	2473.2	Standard polar	33892256
Metoprolol,1TBDMS,isomer #1	COCCC1=CC=C(OCC(CNC(C)C)O[Si](C)(C)C(C)(C)C)C=C1	2293.9	Semi standard non polar	33892256
Metoprolol,1TBDMS,isomer #2	COCCC1=CC=C(OCC(O)CN(C(C)C)[Si](C)(C)C(C)(C)C)C=C1	2457.9	Semi standard non polar	33892256
Metoprolol,2TBDMS,isomer #1	COCCC1=CC=C(OCC(CN(C(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C=C1	2709.8	Semi standard non polar	33892256
Metoprolol,2TBDMS,isomer #1	COCCC1=CC=C(OCC(CN(C(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C=C1	2642.0	Standard non polar	33892256
Metoprolol,2TBDMS,isomer #1	COCCC1=CC=C(OCC(CN(C(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C=C1	2685.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Metoprolol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udi-7920000000-15359015d85b4c565e86	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Metoprolol GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9122000000-12f9e089d37951143a41	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Metoprolol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Metoprolol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Metoprolol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Metoprolol GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Metoprolol 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 - Metoprolol Quattro_QQQ 10V, N/A-QTOF (Annotated)	splash10-0v0c-3248359000-0353ef81c3bc6d7fcfd5	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Metoprolol Quattro_QQQ 25V, N/A-QTOF (Annotated)	splash10-014l-2514911000-b5f7785723f1eaf61e6f	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Metoprolol Quattro_QQQ 40V, N/A-QTOF (Annotated)	splash10-05ir-1729351100-fb362124379cb4616c5e	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Metoprolol LC-ESI-QTOF , positive-QTOF	splash10-01b9-9760000000-90ea4861dda115391e26	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Metoprolol LC-ESI-ITFT , positive-QTOF	splash10-014l-0920000000-b7c75fc96ea4b12a1f40	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Metoprolol LC-ESI-ITFT , positive-QTOF	splash10-014i-0090000000-5e678ec3b5c3302abb3c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Metoprolol LC-ESI-ITFT , positive-QTOF	splash10-014i-0190000000-0ea5b7fc1dda907b176b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Metoprolol LC-ESI-ITFT , positive-QTOF	splash10-01b9-4940000000-5e4d95fb248589c9af91	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Metoprolol LC-ESI-ITFT , positive-QTOF	splash10-05gi-4900000000-73204756032f7604c22e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Metoprolol LC-ESI-ITFT , positive-QTOF	splash10-05fr-4900000000-597c5d64a09cf1b8f88d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Metoprolol LC-ESI-ITFT , positive-QTOF	splash10-0zml-5900000000-ca840796f27bfcb3bd0f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Metoprolol LC-ESI-ITFT , positive-QTOF	splash10-014i-0090000000-9ae9e49826b05fa823f5	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Metoprolol LC-ESI-ITFT , positive-QTOF	splash10-014i-0190000000-cfdea758641b8b5c956e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Metoprolol LC-ESI-ITFT , positive-QTOF	splash10-01b9-3940000000-248e03350c5dfe8e1302	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Metoprolol LC-ESI-ITFT , positive-QTOF	splash10-05gi-4900000000-24d3886dc7605253aeb8	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Metoprolol LC-ESI-ITFT , positive-QTOF	splash10-05gi-4900000000-08c6d3455af24f523db2	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Metoprolol LC-ESI-ITFT , positive-QTOF	splash10-0zmi-5900000000-9b22afca158afbaeb6d1	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Metoprolol LC-ESI-ITFT , positive-QTOF	splash10-014l-0920000000-851dcbef33e79ed22643	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Metoprolol LC-ESI-QTOF , positive-QTOF	splash10-014i-0090000000-61bef9702ed80c36d107	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metoprolol 10V, Positive-QTOF	splash10-014i-1290000000-e429d824fc6518e2de0f	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metoprolol 20V, Positive-QTOF	splash10-00xr-9870000000-6859dfe077cd63365e3b	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metoprolol 40V, Positive-QTOF	splash10-00di-9500000000-84deaf041eadbd4d3ea2	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metoprolol 10V, Negative-QTOF	splash10-0gb9-1790000000-1fa6e9e32d3d6f058f89	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metoprolol 20V, Negative-QTOF	splash10-0udi-1900000000-0545f16ae4bdd137d91e	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metoprolol 40V, Negative-QTOF	splash10-0ldr-3900000000-cfffc2daf6eda94b4e60	2017-07-26	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, experimental)	2012-12-05	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Blood
Feces

Tissue Locations

Liver

Pathways

Name	SMPDB/PathBank	KEGG
Metoprolol Action Pathway		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.071 +/- 0.0076 uM	Adult (>18 years old)	Both	Normal	17825632	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details

Associated Disorders and Diseases

Disease References

Colorectal cancer
Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]

Associated OMIM IDs

114500 (Colorectal cancer)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4027

KEGG Compound ID

C07202

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Metoprolol

METLIN ID

Not Available

PubChem Compound

4171

PDB ID

Not Available

ChEBI ID

6904

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Palmer, Sven; Sidenqvist, Michael. Process for the preparation of metoprolol. PCT Int. Appl. (1998), 12 pp.

Material Safety Data Sheet (MSDS)

Not Available

General References

Bauer LA, Horn JR, Maxon MS, Easterling TR, Shen DD, Strandness DE Jr: Effect of metoprolol and verapamil administered separately and concurrently after single doses on liver blood flow and drug disposition. J Clin Pharmacol. 2000 May;40(5):533-43. [PubMed:10806607 ]
Murthy SS, Shetty HU, Nelson WL, Jackson PR, Lennard MS: Enantioselective and diastereoselective aspects of the oxidative metabolism of metoprolol. Biochem Pharmacol. 1990 Oct 1;40(7):1637-44. [PubMed:2222517 ]
Chaturvedi AK, Smith DR, Canfield DV: A fatality caused by accidental production of hydrogen sulfide. Forensic Sci Int. 2001 Dec 1;123(2-3):211-4. [PubMed:11728749 ]

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

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

Showing metabocard for Metoprolol (HMDB0001932)

MOL for HMDB0001932 (Metoprolol)

3D MOL for HMDB0001932 (Metoprolol)

3D SDF for HMDB0001932 (Metoprolol)

3D-SDF for HMDB0001932 (Metoprolol)

PDB for HMDB0001932 (Metoprolol)

3D PDB for HMDB0001932 (Metoprolol)

SMILES for HMDB0001932 (Metoprolol)

INCHI for HMDB0001932 (Metoprolol)

Structure for HMDB0001932 (Metoprolol)

3D Structure for HMDB0001932 (Metoprolol)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes