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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 15:44:13 UTC

Update Date

2021-09-26 23:11:01 UTC

HMDB ID

HMDB0255850

Secondary Accession Numbers

None

Metabolite Identification

Common Name

O-Demethylmetoprolol

Description

1-[4-(2-hydroxyethyl)phenoxy]-3-[(propan-2-yl)amino]propan-2-ol 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. Based on a literature review a significant number of articles have been published on 1-[4-(2-hydroxyethyl)phenoxy]-3-[(propan-2-yl)amino]propan-2-ol. This compound has been identified in human blood as reported by (PMID: 31557052 ). O-demethylmetoprolol is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically O-Demethylmetoprolol is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0255850
     RDKit          3D
O-Demethylmetoprolol
 41 41  0  0  0  0  0  0  0  0999 V2000
   -4.0677   -1.9302   -0.1135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0986   -0.4903    0.3267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4778    0.0896    0.0088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0805    0.2875   -0.3830 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6437    1.3623    0.5010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7112    2.3146   -0.1809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3204    2.9203   -1.2910 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4569    1.5878   -0.5793 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1133    1.0149    0.5792 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2925    0.3177    0.4431 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8743    0.2113   -0.7916 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0470   -0.4886   -0.9136 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6375   -1.0785    0.1877 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8927   -1.8279   -0.0007 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1163   -0.9622    0.1663 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1218   -0.4471    1.4425 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0617   -0.9775    1.4348 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8645   -0.2585    1.5375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6633   -2.5635    0.7221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0961   -2.2672   -0.4099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3735   -2.1019   -0.9665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9556   -0.4435    1.4281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3388    0.9383   -0.7034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9535    0.4831    0.9468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1516   -0.6513   -0.4449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5183    0.6479   -1.2585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0403    0.8525    1.3033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4993    1.8633    1.0077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4388    3.0916    0.5697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6965    3.6245   -1.5960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7102    0.7993   -1.3340 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2488    2.2605   -1.1105 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4256    0.6703   -1.6715 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5116   -0.5745   -1.9027 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8722   -2.6577    0.7587 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8744   -2.3218   -0.9992 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0485   -1.5387   -0.0628 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0371   -0.1301   -0.5534 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3065    0.0070    1.7023 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4977   -1.4284    2.3282 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4486   -0.2049    2.5516 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 13 17  1  0
 17 18  2  0
 18 10  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  7 30  1  0
  8 31  1  0
  8 32  1  0
 11 33  1  0
 12 34  1  0
 14 35  1  0
 14 36  1  0
 15 37  1  0
 15 38  1  0
 16 39  1  0
 17 40  1  0
 18 41  1  0
M  END


  Mrv1652306031607202D          

 18 18  0  0  0  0            999 V2000
    6.4302   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  3  1  0  0  0  0
  6  4  2  0  0  0  0
  8  7  1  0  0  0  0
 11  1  1  0  0  0  0
 11  2  1  0  0  0  0
 12  3  2  0  0  0  0
 12  4  1  0  0  0  0
 12  7  1  0  0  0  0
 13  9  1  0  0  0  0
 13 10  1  0  0  0  0
 14  5  2  0  0  0  0
 14  6  1  0  0  0  0
 15  9  1  0  0  0  0
 15 11  1  0  0  0  0
 16  8  1  0  0  0  0
 17 13  1  0  0  0  0
 18 10  1  0  0  0  0
 18 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0255850

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C14H23NO3/c1-11(2)15-9-13(17)10-18-14-5-3-12(4-6-14)7-8-16/h3-6,11,13,15-17H,7-10H2,1-2H3

> <INCHI_KEY>
CUKXSBOAIJILRY-UHFFFAOYSA-N

> <FORMULA>
C14H23NO3

> <MOLECULAR_WEIGHT>
253.342

> <EXACT_MASS>
253.167793605

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
29.521420064506806

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.17

> <JCHEM_LOGP>
1.1155306103333331

> <ALOGPS_LOGS>
-2.58

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
15.913916136225822

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.081429887614242

> <JCHEM_PKA_STRONGEST_BASIC>
9.66616635612965

> <JCHEM_POLAR_SURFACE_AREA>
61.72

> <JCHEM_REFRACTIVITY>
71.94640000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.72e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-[4-(2-hydroxyethyl)phenoxy]-3-(isopropylamino)propan-2-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0255850
     RDKit          3D
O-Demethylmetoprolol
 41 41  0  0  0  0  0  0  0  0999 V2000
   -4.0677   -1.9302   -0.1135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0986   -0.4903    0.3267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4778    0.0896    0.0088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0805    0.2875   -0.3830 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6437    1.3623    0.5010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7112    2.3146   -0.1809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3204    2.9203   -1.2910 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4569    1.5878   -0.5793 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1133    1.0149    0.5792 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2925    0.3177    0.4431 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8743    0.2113   -0.7916 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0470   -0.4886   -0.9136 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6375   -1.0785    0.1877 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8927   -1.8279   -0.0007 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1163   -0.9622    0.1663 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1218   -0.4471    1.4425 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0617   -0.9775    1.4348 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8645   -0.2585    1.5375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6633   -2.5635    0.7221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0961   -2.2672   -0.4099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3735   -2.1019   -0.9665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9556   -0.4435    1.4281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3388    0.9383   -0.7034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9535    0.4831    0.9468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1516   -0.6513   -0.4449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5183    0.6479   -1.2585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0403    0.8525    1.3033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4993    1.8633    1.0077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4388    3.0916    0.5697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6965    3.6245   -1.5960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7102    0.7993   -1.3340 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2488    2.2605   -1.1105 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4256    0.6703   -1.6715 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5116   -0.5745   -1.9027 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8722   -2.6577    0.7587 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8744   -2.3218   -0.9992 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0485   -1.5387   -0.0628 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0371   -0.1301   -0.5534 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3065    0.0070    1.7023 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4977   -1.4284    2.3282 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4486   -0.2049    2.5516 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 13 17  1  0
 17 18  2  0
 18 10  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  7 30  1  0
  8 31  1  0
  8 32  1  0
 11 33  1  0
 12 34  1  0
 14 35  1  0
 14 36  1  0
 15 37  1  0
 15 38  1  0
 16 39  1  0
 17 40  1  0
 18 41  1  0
M  END

HEADER    PROTEIN                                 03-JUN-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-JUN-16         0                                  
HETATM    1  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       9.336  -0.770   0.000  0.00  0.00           N+0
HETATM   16  O   UNK     0      -2.667   4.620   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
CONECT    1   11                                                            
CONECT    2   11                                                            
CONECT    3    5   12                                                       
CONECT    4    6   12                                                       
CONECT    5    3   14                                                       
CONECT    6    4   14                                                       
CONECT    7    8   12                                                       
CONECT    8    7   16                                                       
CONECT    9   13   15                                                       
CONECT   10   13   18                                                       
CONECT   11    1    2   15                                                  
CONECT   12    3    4    7                                                  
CONECT   13    9   10   17                                                  
CONECT   14    5    6   18                                                  
CONECT   15    9   11                                                       
CONECT   16    8                                                            
CONECT   17   13                                                            
CONECT   18   10   14                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   36    0
END

COMPND    HMDB0255850
HETATM    1  C1  UNL     1      -4.068  -1.930  -0.114  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.099  -0.490   0.327  1.00  0.00           C  
HETATM    3  C3  UNL     1      -5.478   0.090   0.009  1.00  0.00           C  
HETATM    4  N1  UNL     1      -3.081   0.288  -0.383  1.00  0.00           N  
HETATM    5  C4  UNL     1      -2.644   1.362   0.501  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.711   2.315  -0.181  1.00  0.00           C  
HETATM    7  O1  UNL     1      -2.320   2.920  -1.291  1.00  0.00           O  
HETATM    8  C6  UNL     1      -0.457   1.588  -0.579  1.00  0.00           C  
HETATM    9  O2  UNL     1       0.113   1.015   0.579  1.00  0.00           O  
HETATM   10  C7  UNL     1       1.292   0.318   0.443  1.00  0.00           C  
HETATM   11  C8  UNL     1       1.874   0.211  -0.792  1.00  0.00           C  
HETATM   12  C9  UNL     1       3.047  -0.489  -0.914  1.00  0.00           C  
HETATM   13  C10 UNL     1       3.638  -1.079   0.188  1.00  0.00           C  
HETATM   14  C11 UNL     1       4.893  -1.828  -0.001  1.00  0.00           C  
HETATM   15  C12 UNL     1       6.116  -0.962   0.166  1.00  0.00           C  
HETATM   16  O3  UNL     1       6.122  -0.447   1.442  1.00  0.00           O  
HETATM   17  C13 UNL     1       3.062  -0.977   1.435  1.00  0.00           C  
HETATM   18  C14 UNL     1       1.865  -0.259   1.537  1.00  0.00           C  
HETATM   19  H1  UNL     1      -3.663  -2.563   0.722  1.00  0.00           H  
HETATM   20  H2  UNL     1      -5.096  -2.267  -0.410  1.00  0.00           H  
HETATM   21  H3  UNL     1      -3.373  -2.102  -0.966  1.00  0.00           H  
HETATM   22  H4  UNL     1      -3.956  -0.444   1.428  1.00  0.00           H  
HETATM   23  H5  UNL     1      -5.339   0.938  -0.703  1.00  0.00           H  
HETATM   24  H6  UNL     1      -5.953   0.483   0.947  1.00  0.00           H  
HETATM   25  H7  UNL     1      -6.152  -0.651  -0.445  1.00  0.00           H  
HETATM   26  H8  UNL     1      -3.518   0.648  -1.258  1.00  0.00           H  
HETATM   27  H9  UNL     1      -2.040   0.853   1.303  1.00  0.00           H  
HETATM   28  H10 UNL     1      -3.499   1.863   1.008  1.00  0.00           H  
HETATM   29  H11 UNL     1      -1.439   3.092   0.570  1.00  0.00           H  
HETATM   30  H12 UNL     1      -1.697   3.624  -1.596  1.00  0.00           H  
HETATM   31  H13 UNL     1      -0.710   0.799  -1.334  1.00  0.00           H  
HETATM   32  H14 UNL     1       0.249   2.260  -1.111  1.00  0.00           H  
HETATM   33  H15 UNL     1       1.426   0.670  -1.672  1.00  0.00           H  
HETATM   34  H16 UNL     1       3.512  -0.574  -1.903  1.00  0.00           H  
HETATM   35  H17 UNL     1       4.872  -2.658   0.759  1.00  0.00           H  
HETATM   36  H18 UNL     1       4.874  -2.322  -0.999  1.00  0.00           H  
HETATM   37  H19 UNL     1       7.048  -1.539  -0.063  1.00  0.00           H  
HETATM   38  H20 UNL     1       6.037  -0.130  -0.553  1.00  0.00           H  
HETATM   39  H21 UNL     1       5.306   0.007   1.702  1.00  0.00           H  
HETATM   40  H22 UNL     1       3.498  -1.428   2.328  1.00  0.00           H  
HETATM   41  H23 UNL     1       1.449  -0.205   2.552  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3    4   22
CONECT    3   23   24   25
CONECT    4    5   26
CONECT    5    6   27   28
CONECT    6    7    8   29
CONECT    7   30
CONECT    8    9   31   32
CONECT    9   10
CONECT   10   11   11   18
CONECT   11   12   33
CONECT   12   13   13   34
CONECT   13   14   17
CONECT   14   15   35   36
CONECT   15   16   37   38
CONECT   16   39
CONECT   17   18   18   40
CONECT   18   41
END

HMDB0255850
     RDKit          3D
O-Demethylmetoprolol
 41 41  0  0  0  0  0  0  0  0999 V2000
   -4.0677   -1.9302   -0.1135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0986   -0.4903    0.3267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4778    0.0896    0.0088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0805    0.2875   -0.3830 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6437    1.3623    0.5010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7112    2.3146   -0.1809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3204    2.9203   -1.2910 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4569    1.5878   -0.5793 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1133    1.0149    0.5792 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2925    0.3177    0.4431 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8743    0.2113   -0.7916 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0470   -0.4886   -0.9136 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6375   -1.0785    0.1877 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8927   -1.8279   -0.0007 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1163   -0.9622    0.1663 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1218   -0.4471    1.4425 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0617   -0.9775    1.4348 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8645   -0.2585    1.5375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6633   -2.5635    0.7221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0961   -2.2672   -0.4099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3735   -2.1019   -0.9665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9556   -0.4435    1.4281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3388    0.9383   -0.7034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9535    0.4831    0.9468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1516   -0.6513   -0.4449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5183    0.6479   -1.2585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0403    0.8525    1.3033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4993    1.8633    1.0077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4388    3.0916    0.5697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6965    3.6245   -1.5960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7102    0.7993   -1.3340 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2488    2.2605   -1.1105 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4256    0.6703   -1.6715 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5116   -0.5745   -1.9027 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8722   -2.6577    0.7587 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8744   -2.3218   -0.9992 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0485   -1.5387   -0.0628 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0371   -0.1301   -0.5534 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3065    0.0070    1.7023 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4977   -1.4284    2.3282 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4486   -0.2049    2.5516 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 13 17  1  0
 17 18  2  0
 18 10  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  7 30  1  0
  8 31  1  0
  8 32  1  0
 11 33  1  0
 12 34  1  0
 14 35  1  0
 14 36  1  0
 15 37  1  0
 15 38  1  0
 16 39  1  0
 17 40  1  0
 18 41  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
H105-22, (+-)-Isomer	MeSH

Chemical Formula

C₁₄H₂₃NO₃

Average Molecular Weight

253.342

Monoisotopic Molecular Weight

253.167793605

IUPAC Name

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

Traditional Name

1-[4-(2-hydroxyethyl)phenoxy]-3-(isopropylamino)propan-2-ol

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C14H23NO3/c1-11(2)15-9-13(17)10-18-14-5-3-12(4-6-14)7-8-16/h3-6,11,13,15-17H,7-10H2,1-2H3

InChI Key

CUKXSBOAIJILRY-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
Secondary alcohol
1,2-aminoalcohol
Secondary amine
Ether
Secondary aliphatic amine
Organopnictogen compound
Primary alcohol
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Amine
Organic nitrogen compound
Alcohol
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Physical Properties

State

Not Available

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	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	1.17	ALOGPS
logP	1.12	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	14.08	ChemAxon
pKa (Strongest Basic)	9.67	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	61.72 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	71.95 m³·mol⁻¹	ChemAxon
Polarizability	29.52 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
DeepCCS	[M+H]+	158.995	30932474
DeepCCS	[M-H]-	156.637	30932474
DeepCCS	[M-2H]-	190.345	30932474
DeepCCS	[M+Na]+	165.305	30932474
AllCCS	[M+H]+	162.3	32859911
AllCCS	[M+H-H2O]+	159.1	32859911
AllCCS	[M+NH4]+	165.3	32859911
AllCCS	[M+Na]+	166.1	32859911
AllCCS	[M-H]-	162.5	32859911
AllCCS	[M+Na-2H]-	163.3	32859911
AllCCS	[M+HCOO]-	164.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
O-Demethylmetoprolol	CC(C)NCC(O)COC1=CC=C(CCO)C=C1	3145.7	Standard polar	33892256
O-Demethylmetoprolol	CC(C)NCC(O)COC1=CC=C(CCO)C=C1	2046.1	Standard non polar	33892256
O-Demethylmetoprolol	CC(C)NCC(O)COC1=CC=C(CCO)C=C1	2077.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
O-Demethylmetoprolol,3TMS,isomer #1	CC(C)N(CC(COC1=CC=C(CCO[Si](C)(C)C)C=C1)O[Si](C)(C)C)[Si](C)(C)C	2351.4	Semi standard non polar	33892256
O-Demethylmetoprolol,3TMS,isomer #1	CC(C)N(CC(COC1=CC=C(CCO[Si](C)(C)C)C=C1)O[Si](C)(C)C)[Si](C)(C)C	2375.8	Standard non polar	33892256
O-Demethylmetoprolol,3TMS,isomer #1	CC(C)N(CC(COC1=CC=C(CCO[Si](C)(C)C)C=C1)O[Si](C)(C)C)[Si](C)(C)C	2435.2	Standard polar	33892256
O-Demethylmetoprolol,3TBDMS,isomer #1	CC(C)N(CC(COC1=CC=C(CCO[Si](C)(C)C(C)(C)C)C=C1)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3027.6	Semi standard non polar	33892256
O-Demethylmetoprolol,3TBDMS,isomer #1	CC(C)N(CC(COC1=CC=C(CCO[Si](C)(C)C(C)(C)C)C=C1)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2926.1	Standard non polar	33892256
O-Demethylmetoprolol,3TBDMS,isomer #1	CC(C)N(CC(COC1=CC=C(CCO[Si](C)(C)C(C)(C)C)C=C1)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2727.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - O-Demethylmetoprolol GC-MS (Non-derivatized) - 70eV, Positive	splash10-059i-7920000000-23117fa3f9d70cb65e85	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - O-Demethylmetoprolol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - O-Demethylmetoprolol GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - O-Demethylmetoprolol GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - O-Demethylmetoprolol GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - O-Demethylmetoprolol GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - O-Demethylmetoprolol GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - O-Demethylmetoprolol GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - O-Demethylmetoprolol GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - O-Demethylmetoprolol GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - O-Demethylmetoprolol GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - O-Demethylmetoprolol GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - O-Demethylmetoprolol GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - O-Demethylmetoprolol GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - O-Demethylmetoprolol 60V, Positive-QTOF	splash10-05fr-6900000000-2efb4c0d326d4a9cb5ef	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - O-Demethylmetoprolol 90V, Positive-QTOF	splash10-0pbd-9600000000-bf796a9e34f6eb2f304d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - O-Demethylmetoprolol 45V, Positive-QTOF	splash10-0kor-5910000000-eada6a8fc07fc23d1ce7	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - O-Demethylmetoprolol 180V, Positive-QTOF	splash10-0fr2-9200000000-eba2d01aefc2791ffb79	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - O-Demethylmetoprolol 75V, Positive-QTOF	splash10-05fu-8900000000-128ebe6a353f776313bd	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - O-Demethylmetoprolol 45V, Positive-QTOF	splash10-0kor-5910000000-0029fbf3ef0abbfbc13f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - O-Demethylmetoprolol 60V, Positive-QTOF	splash10-05fr-6900000000-cd0714383b55b9e5834d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - O-Demethylmetoprolol 45V, Positive-QTOF	splash10-0kor-5910000000-9e35acc99b49ad465b3a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - O-Demethylmetoprolol 30V, Positive-QTOF	splash10-0udi-1290000000-8205e802d3a4ceb4266d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - O-Demethylmetoprolol 15V, Positive-QTOF	splash10-0udi-0090000000-9bc726d13128176915b3	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - O-Demethylmetoprolol 75V, Positive-QTOF	splash10-05fu-9800000000-0de5050ddc9d36354a72	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - O-Demethylmetoprolol 75V, Positive-QTOF	splash10-05fu-9800000000-893993b5f6a69dfd9dfe	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - O-Demethylmetoprolol 90V, Positive-QTOF	splash10-0kfy-9500000000-cf22b3e1c106d1650240	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - O-Demethylmetoprolol 150V, Positive-QTOF	splash10-00kb-9200000000-e546dab265be6a79140a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - O-Demethylmetoprolol 120V, Positive-QTOF	splash10-052e-9300000000-f92869c6237df88096a3	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Demethylmetoprolol 10V, Positive-QTOF	splash10-0f79-0390000000-1ee1832fbe3322c8cf58	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Demethylmetoprolol 20V, Positive-QTOF	splash10-00di-6940000000-d44eeb1769882df1d65d	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Demethylmetoprolol 40V, Positive-QTOF	splash10-00di-9500000000-2b7b6b0dfcca9f6d1795	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Demethylmetoprolol 10V, Negative-QTOF	splash10-0udi-1490000000-8307200337a9b7694cc0	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Demethylmetoprolol 20V, Negative-QTOF	splash10-0a4r-0910000000-38ee79fe6a9281d47295	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Demethylmetoprolol 40V, Negative-QTOF	splash10-0aor-2900000000-986892a9160efac046ec	2019-02-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

142425

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

162181

PDB ID

Not Available

ChEBI ID

Not Available

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for O-Demethylmetoprolol (HMDB0255850)

MOL for HMDB0255850 (O-Demethylmetoprolol)

3D MOL for HMDB0255850 (O-Demethylmetoprolol)

3D SDF for HMDB0255850 (O-Demethylmetoprolol)

3D-SDF for HMDB0255850 (O-Demethylmetoprolol)

PDB for HMDB0255850 (O-Demethylmetoprolol)

3D PDB for HMDB0255850 (O-Demethylmetoprolol)

SMILES for HMDB0255850 (O-Demethylmetoprolol)

INCHI for HMDB0255850 (O-Demethylmetoprolol)

Structure for HMDB0255850 (O-Demethylmetoprolol)

3D Structure for HMDB0255850 (O-Demethylmetoprolol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra