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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-07-09 16:11:30 UTC

Update Date

2021-09-14 15:45:34 UTC

HMDB ID

HMDB0060994

Secondary Accession Numbers

HMDB60994

Metabolite Identification

Common Name

alpha-Hydroxymetoprolol

Description

alpha-Hydroxymetoprolol is a metabolite of metoprolol. Metoprolol is a selective β1 receptor blocker used in treatment of several diseases of the cardiovascular system, especially hypertension. The active substance metoprolol is employed either as metoprolol succinate or metoprolol tartrate (where 100 mg metoprolol tartrate corresponds to 95 mg metoprolol succinate). The tartrate is an immediate-release and the succinate is an extended-release formulation. (Wikipedia)

Structure

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

HMDB0060994
     RDKit          3D
alpha-Hydroxymetoprolol
 45 45  0  0  0  0  0  0  0  0999 V2000
    5.4241    2.2006    0.1247 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0741    1.1717    0.9561 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3664   -0.0943    0.5272 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7153   -0.4956   -0.7708 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1438   -1.8217   -1.0203 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2348   -0.4974   -0.6463 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5934   -1.4667    0.1128 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2235   -1.4935    0.2496 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4221   -0.5379   -0.3760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9697   -0.5830   -0.2228 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5925   -1.5657    0.5444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1174   -1.4189    0.5821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5257   -2.5049    1.4161 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5048   -0.1258    1.2382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2218    1.0651    0.5509 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9525    1.4242   -0.5962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8929    0.5571   -1.7914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4294    1.6793   -0.3039 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0552    0.4186   -1.1254 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4244    0.4356   -1.2551 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4834    2.2974   -0.1170 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1430    3.1484    0.6699 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7702    2.2247   -0.7889 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9297   -0.7917    1.3050 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4487   -0.3222    0.5234 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0589    0.0870   -1.6363 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1190   -2.3242   -0.1714 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2313   -2.2042    0.5936 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7723   -2.2580    0.8437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1931   -1.6348    1.5805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3901   -2.5488    0.0800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4989   -1.5654   -0.4318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5832   -3.3096    0.8346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9101   -0.0952    2.2101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5762   -0.1601    1.6001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9575    1.8741    1.1181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5633    2.4490   -0.9116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8919    0.1357   -1.9796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7225   -0.1859   -1.8529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0634    1.2383   -2.6938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9324    1.7583   -1.2895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5970    2.6179    0.2301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8961    0.8328    0.2258 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4538    1.1825   -1.6285 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8956    1.2071   -1.8591 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
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
  9 19  1  0
 19 20  2  0
 20  6  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  5 27  1  0
  7 28  1  0
  8 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  0
 13 33  1  0
 14 34  1  0
 14 35  1  0
 15 36  1  0
 16 37  1  0
 17 38  1  0
 17 39  1  0
 17 40  1  0
 18 41  1  0
 18 42  1  0
 18 43  1  0
 19 44  1  0
 20 45  1  0
M  END


  Mrv0541 07091309112D          

 20 20  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
   -2.8579    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
    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
   -1.4289    0.8250    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
   -0.7145    1.2375    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
    3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    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
  6  4  1  0  0  0  0
  7  5  2  0  0  0  0
 11  1  1  0  0  0  0
 11  2  1  0  0  0  0
 12  4  2  0  0  0  0
 12  5  1  0  0  0  0
 13  8  1  0  0  0  0
 13  9  1  0  0  0  0
 14  6  2  0  0  0  0
 14  7  1  0  0  0  0
 15 10  1  0  0  0  0
 15 12  1  0  0  0  0
 16  8  1  0  0  0  0
 16 11  1  0  0  0  0
 17 13  1  0  0  0  0
 18 15  1  0  0  0  0
 19  3  1  0  0  0  0
 19 10  1  0  0  0  0
 20  9  1  0  0  0  0
 20 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060994

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C15H25NO4/c1-11(2)16-8-13(17)9-20-14-6-4-12(5-7-14)15(18)10-19-3/h4-7,11,13,15-18H,8-10H2,1-3H3

> <INCHI_KEY>
OFRYBPCSEMMZHR-UHFFFAOYSA-N

> <FORMULA>
C15H25NO4

> <MOLECULAR_WEIGHT>
283.3633

> <EXACT_MASS>
283.178358293

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
32.22635860507566

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.32

> <JCHEM_LOGP>
0.8396609670000004

> <ALOGPS_LOGS>
-2.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.238113391011563

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.553818504540608

> <JCHEM_PKA_STRONGEST_BASIC>
9.666126787389567

> <JCHEM_POLAR_SURFACE_AREA>
70.95

> <JCHEM_REFRACTIVITY>
77.90510000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.43e+00 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060994
     RDKit          3D
alpha-Hydroxymetoprolol
 45 45  0  0  0  0  0  0  0  0999 V2000
    5.4241    2.2006    0.1247 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0741    1.1717    0.9561 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3664   -0.0943    0.5272 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7153   -0.4956   -0.7708 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1438   -1.8217   -1.0203 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2348   -0.4974   -0.6463 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5934   -1.4667    0.1128 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2235   -1.4935    0.2496 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4221   -0.5379   -0.3760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9697   -0.5830   -0.2228 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5925   -1.5657    0.5444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1174   -1.4189    0.5821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5257   -2.5049    1.4161 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5048   -0.1258    1.2382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2218    1.0651    0.5509 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9525    1.4242   -0.5962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8929    0.5571   -1.7914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4294    1.6793   -0.3039 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0552    0.4186   -1.1254 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4244    0.4356   -1.2551 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4834    2.2974   -0.1170 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1430    3.1484    0.6699 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7702    2.2247   -0.7889 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9297   -0.7917    1.3050 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4487   -0.3222    0.5234 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0589    0.0870   -1.6363 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1190   -2.3242   -0.1714 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2313   -2.2042    0.5936 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7723   -2.2580    0.8437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1931   -1.6348    1.5805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3901   -2.5488    0.0800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4989   -1.5654   -0.4318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5832   -3.3096    0.8346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9101   -0.0952    2.2101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5762   -0.1601    1.6001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9575    1.8741    1.1181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5633    2.4490   -0.9116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8919    0.1357   -1.9796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7225   -0.1859   -1.8529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0634    1.2383   -2.6938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9324    1.7583   -1.2895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5970    2.6179    0.2301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8961    0.8328    0.2258 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4538    1.1825   -1.6285 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8956    1.2071   -1.8591 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
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
  9 19  1  0
 19 20  2  0
 20  6  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  5 27  1  0
  7 28  1  0
  8 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  0
 13 33  1  0
 14 34  1  0
 14 35  1  0
 15 36  1  0
 16 37  1  0
 17 38  1  0
 17 39  1  0
 17 40  1  0
 18 41  1  0
 18 42  1  0
 18 43  1  0
 19 44  1  0
 20 45  1  0
M  END

HEADER    PROTEIN                                 09-JUL-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-JUL-13         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      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.667   1.540   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  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       9.336  -0.770   0.000  0.00  0.00           N+0
HETATM   17  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -4.001   2.310   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
CONECT    1   11                                                            
CONECT    2   11                                                            
CONECT    3   19                                                            
CONECT    4    6   12                                                       
CONECT    5    7   12                                                       
CONECT    6    4   14                                                       
CONECT    7    5   14                                                       
CONECT    8   13   16                                                       
CONECT    9   13   20                                                       
CONECT   10   15   19                                                       
CONECT   11    1    2   16                                                  
CONECT   12    4    5   15                                                  
CONECT   13    8    9   17                                                  
CONECT   14    6    7   20                                                  
CONECT   15   10   12   18                                                  
CONECT   16    8   11                                                       
CONECT   17   13                                                            
CONECT   18   15                                                            
CONECT   19    3   10                                                       
CONECT   20    9   14                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   40    0
END

COMPND    HMDB0060994
HETATM    1  C1  UNL     1       5.424   2.201   0.125  1.00  0.00           C  
HETATM    2  O1  UNL     1       5.074   1.172   0.956  1.00  0.00           O  
HETATM    3  C2  UNL     1       5.366  -0.094   0.527  1.00  0.00           C  
HETATM    4  C3  UNL     1       4.715  -0.496  -0.771  1.00  0.00           C  
HETATM    5  O2  UNL     1       5.144  -1.822  -1.020  1.00  0.00           O  
HETATM    6  C4  UNL     1       3.235  -0.497  -0.646  1.00  0.00           C  
HETATM    7  C5  UNL     1       2.593  -1.467   0.113  1.00  0.00           C  
HETATM    8  C6  UNL     1       1.223  -1.494   0.250  1.00  0.00           C  
HETATM    9  C7  UNL     1       0.422  -0.538  -0.376  1.00  0.00           C  
HETATM   10  O3  UNL     1      -0.970  -0.583  -0.223  1.00  0.00           O  
HETATM   11  C8  UNL     1      -1.593  -1.566   0.544  1.00  0.00           C  
HETATM   12  C9  UNL     1      -3.117  -1.419   0.582  1.00  0.00           C  
HETATM   13  O4  UNL     1      -3.526  -2.505   1.416  1.00  0.00           O  
HETATM   14  C10 UNL     1      -3.505  -0.126   1.238  1.00  0.00           C  
HETATM   15  N1  UNL     1      -3.222   1.065   0.551  1.00  0.00           N  
HETATM   16  C11 UNL     1      -3.952   1.424  -0.596  1.00  0.00           C  
HETATM   17  C12 UNL     1      -3.893   0.557  -1.791  1.00  0.00           C  
HETATM   18  C13 UNL     1      -5.429   1.679  -0.304  1.00  0.00           C  
HETATM   19  C14 UNL     1       1.055   0.419  -1.125  1.00  0.00           C  
HETATM   20  C15 UNL     1       2.424   0.436  -1.255  1.00  0.00           C  
HETATM   21  H1  UNL     1       6.483   2.297  -0.117  1.00  0.00           H  
HETATM   22  H2  UNL     1       5.143   3.148   0.670  1.00  0.00           H  
HETATM   23  H3  UNL     1       4.770   2.225  -0.789  1.00  0.00           H  
HETATM   24  H4  UNL     1       4.930  -0.792   1.305  1.00  0.00           H  
HETATM   25  H5  UNL     1       6.449  -0.322   0.523  1.00  0.00           H  
HETATM   26  H6  UNL     1       5.059   0.087  -1.636  1.00  0.00           H  
HETATM   27  H7  UNL     1       5.119  -2.324  -0.171  1.00  0.00           H  
HETATM   28  H8  UNL     1       3.231  -2.204   0.594  1.00  0.00           H  
HETATM   29  H9  UNL     1       0.772  -2.258   0.844  1.00  0.00           H  
HETATM   30  H10 UNL     1      -1.193  -1.635   1.581  1.00  0.00           H  
HETATM   31  H11 UNL     1      -1.390  -2.549   0.080  1.00  0.00           H  
HETATM   32  H12 UNL     1      -3.499  -1.565  -0.432  1.00  0.00           H  
HETATM   33  H13 UNL     1      -3.583  -3.310   0.835  1.00  0.00           H  
HETATM   34  H14 UNL     1      -2.910  -0.095   2.210  1.00  0.00           H  
HETATM   35  H15 UNL     1      -4.576  -0.160   1.600  1.00  0.00           H  
HETATM   36  H16 UNL     1      -2.958   1.874   1.118  1.00  0.00           H  
HETATM   37  H17 UNL     1      -3.563   2.449  -0.912  1.00  0.00           H  
HETATM   38  H18 UNL     1      -2.892   0.136  -1.980  1.00  0.00           H  
HETATM   39  H19 UNL     1      -4.722  -0.186  -1.853  1.00  0.00           H  
HETATM   40  H20 UNL     1      -4.063   1.238  -2.694  1.00  0.00           H  
HETATM   41  H21 UNL     1      -5.932   1.758  -1.290  1.00  0.00           H  
HETATM   42  H22 UNL     1      -5.597   2.618   0.230  1.00  0.00           H  
HETATM   43  H23 UNL     1      -5.896   0.833   0.226  1.00  0.00           H  
HETATM   44  H24 UNL     1       0.454   1.182  -1.629  1.00  0.00           H  
HETATM   45  H25 UNL     1       2.896   1.207  -1.859  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3
CONECT    3    4   24   25
CONECT    4    5    6   26
CONECT    5   27
CONECT    6    7    7   20
CONECT    7    8   28
CONECT    8    9    9   29
CONECT    9   10   19
CONECT   10   11
CONECT   11   12   30   31
CONECT   12   13   14   32
CONECT   13   33
CONECT   14   15   34   35
CONECT   15   16   36
CONECT   16   17   18   37
CONECT   17   38   39   40
CONECT   18   41   42   43
CONECT   19   20   20   44
CONECT   20   45
END

HMDB0060994
     RDKit          3D
alpha-Hydroxymetoprolol
 45 45  0  0  0  0  0  0  0  0999 V2000
    5.4241    2.2006    0.1247 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0741    1.1717    0.9561 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3664   -0.0943    0.5272 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7153   -0.4956   -0.7708 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1438   -1.8217   -1.0203 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2348   -0.4974   -0.6463 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5934   -1.4667    0.1128 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2235   -1.4935    0.2496 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4221   -0.5379   -0.3760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9697   -0.5830   -0.2228 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5925   -1.5657    0.5444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1174   -1.4189    0.5821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5257   -2.5049    1.4161 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5048   -0.1258    1.2382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2218    1.0651    0.5509 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9525    1.4242   -0.5962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8929    0.5571   -1.7914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4294    1.6793   -0.3039 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0552    0.4186   -1.1254 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4244    0.4356   -1.2551 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4834    2.2974   -0.1170 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1430    3.1484    0.6699 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7702    2.2247   -0.7889 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9297   -0.7917    1.3050 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4487   -0.3222    0.5234 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0589    0.0870   -1.6363 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1190   -2.3242   -0.1714 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2313   -2.2042    0.5936 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7723   -2.2580    0.8437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1931   -1.6348    1.5805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3901   -2.5488    0.0800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4989   -1.5654   -0.4318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5832   -3.3096    0.8346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9101   -0.0952    2.2101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5762   -0.1601    1.6001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9575    1.8741    1.1181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5633    2.4490   -0.9116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8919    0.1357   -1.9796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7225   -0.1859   -1.8529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0634    1.2383   -2.6938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9324    1.7583   -1.2895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5970    2.6179    0.2301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8961    0.8328    0.2258 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4538    1.1825   -1.6285 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8956    1.2071   -1.8591 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
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
  9 19  1  0
 19 20  2  0
 20  6  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  5 27  1  0
  7 28  1  0
  8 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  0
 13 33  1  0
 14 34  1  0
 14 35  1  0
 15 36  1  0
 16 37  1  0
 17 38  1  0
 17 39  1  0
 17 40  1  0
 18 41  1  0
 18 42  1  0
 18 43  1  0
 19 44  1  0
 20 45  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
a-Hydroxymetoprolol	Generator
Α-hydroxymetoprolol	Generator

Chemical Formula

C₁₅H₂₅NO₄

Average Molecular Weight

283.3633

Monoisotopic Molecular Weight

283.178358293

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C15H25NO4/c1-11(2)16-8-13(17)9-20-14-6-4-12(5-7-14)15(18)10-19-3/h4-7,11,13,15-18H,8-10H2,1-3H3

InChI Key

OFRYBPCSEMMZHR-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
Monocyclic benzene moiety
1,2-aminoalcohol
Secondary alcohol
Dialkyl ether
Secondary aliphatic amine
Secondary amine
Ether
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Aromatic alcohol
Hydrocarbon derivative
Organopnictogen compound
Amine
Organic oxygen compound
Alcohol
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Non-excretory biofluid

Blood (HMDB: HMDB0060994)

Excreta

Urine (HMDB: HMDB0060994)

Organ

Kidney (HMDB: HMDB0060994)
Liver (HMDB: HMDB0060994)

Cellular substructure

Cytoplasm (HMDB: HMDB0060994)

Process

Not Available

Role

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
Water Solubility	1.43 g/L	ALOGPS
logP	1.32	ALOGPS
logP	0.84	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	13.55	ChemAxon
pKa (Strongest Basic)	9.67	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	70.95 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	77.91 m³·mol⁻¹	ChemAxon
Polarizability	32.23 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]+	166.34	31661259
DarkChem	[M-H]-	164.801	31661259
DeepCCS	[M+H]+	170.097	30932474
DeepCCS	[M-H]-	167.739	30932474
DeepCCS	[M-2H]-	200.625	30932474
DeepCCS	[M+Na]+	176.19	30932474
AllCCS	[M+H]+	170.4	32859911
AllCCS	[M+H-H2O]+	167.3	32859911
AllCCS	[M+NH4]+	173.3	32859911
AllCCS	[M+Na]+	174.1	32859911
AllCCS	[M-H]-	170.5	32859911
AllCCS	[M+Na-2H]-	171.3	32859911
AllCCS	[M+HCOO]-	172.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
alpha-Hydroxymetoprolol	COCC(O)C1=CC=C(OCC(O)CNC(C)C)C=C1	2982.8	Standard polar	33892256
alpha-Hydroxymetoprolol	COCC(O)C1=CC=C(OCC(O)CNC(C)C)C=C1	2135.7	Standard non polar	33892256
alpha-Hydroxymetoprolol	COCC(O)C1=CC=C(OCC(O)CNC(C)C)C=C1	2172.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
alpha-Hydroxymetoprolol,1TMS,isomer #1	COCC(O[Si](C)(C)C)C1=CC=C(OCC(O)CNC(C)C)C=C1	2219.8	Semi standard non polar	33892256
alpha-Hydroxymetoprolol,1TMS,isomer #2	COCC(O)C1=CC=C(OCC(CNC(C)C)O[Si](C)(C)C)C=C1	2210.8	Semi standard non polar	33892256
alpha-Hydroxymetoprolol,1TMS,isomer #3	COCC(O)C1=CC=C(OCC(O)CN(C(C)C)[Si](C)(C)C)C=C1	2364.5	Semi standard non polar	33892256
alpha-Hydroxymetoprolol,2TMS,isomer #1	COCC(O[Si](C)(C)C)C1=CC=C(OCC(CNC(C)C)O[Si](C)(C)C)C=C1	2167.8	Semi standard non polar	33892256
alpha-Hydroxymetoprolol,2TMS,isomer #2	COCC(O[Si](C)(C)C)C1=CC=C(OCC(O)CN(C(C)C)[Si](C)(C)C)C=C1	2352.7	Semi standard non polar	33892256
alpha-Hydroxymetoprolol,2TMS,isomer #3	COCC(O)C1=CC=C(OCC(CN(C(C)C)[Si](C)(C)C)O[Si](C)(C)C)C=C1	2374.8	Semi standard non polar	33892256
alpha-Hydroxymetoprolol,3TMS,isomer #1	COCC(O[Si](C)(C)C)C1=CC=C(OCC(CN(C(C)C)[Si](C)(C)C)O[Si](C)(C)C)C=C1	2367.0	Semi standard non polar	33892256
alpha-Hydroxymetoprolol,3TMS,isomer #1	COCC(O[Si](C)(C)C)C1=CC=C(OCC(CN(C(C)C)[Si](C)(C)C)O[Si](C)(C)C)C=C1	2298.7	Standard non polar	33892256
alpha-Hydroxymetoprolol,3TMS,isomer #1	COCC(O[Si](C)(C)C)C1=CC=C(OCC(CN(C(C)C)[Si](C)(C)C)O[Si](C)(C)C)C=C1	2555.7	Standard polar	33892256
alpha-Hydroxymetoprolol,1TBDMS,isomer #1	COCC(O[Si](C)(C)C(C)(C)C)C1=CC=C(OCC(O)CNC(C)C)C=C1	2472.3	Semi standard non polar	33892256
alpha-Hydroxymetoprolol,1TBDMS,isomer #2	COCC(O)C1=CC=C(OCC(CNC(C)C)O[Si](C)(C)C(C)(C)C)C=C1	2460.6	Semi standard non polar	33892256
alpha-Hydroxymetoprolol,1TBDMS,isomer #3	COCC(O)C1=CC=C(OCC(O)CN(C(C)C)[Si](C)(C)C(C)(C)C)C=C1	2621.0	Semi standard non polar	33892256
alpha-Hydroxymetoprolol,2TBDMS,isomer #1	COCC(O[Si](C)(C)C(C)(C)C)C1=CC=C(OCC(CNC(C)C)O[Si](C)(C)C(C)(C)C)C=C1	2640.1	Semi standard non polar	33892256
alpha-Hydroxymetoprolol,2TBDMS,isomer #2	COCC(O[Si](C)(C)C(C)(C)C)C1=CC=C(OCC(O)CN(C(C)C)[Si](C)(C)C(C)(C)C)C=C1	2836.4	Semi standard non polar	33892256
alpha-Hydroxymetoprolol,2TBDMS,isomer #3	COCC(O)C1=CC=C(OCC(CN(C(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C=C1	2856.8	Semi standard non polar	33892256
alpha-Hydroxymetoprolol,3TBDMS,isomer #1	COCC(O[Si](C)(C)C(C)(C)C)C1=CC=C(OCC(CN(C(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C=C1	3038.5	Semi standard non polar	33892256
alpha-Hydroxymetoprolol,3TBDMS,isomer #1	COCC(O[Si](C)(C)C(C)(C)C)C1=CC=C(OCC(CN(C(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C=C1	2846.6	Standard non polar	33892256
alpha-Hydroxymetoprolol,3TBDMS,isomer #1	COCC(O[Si](C)(C)C(C)(C)C)C1=CC=C(OCC(CN(C(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C=C1	2842.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - alpha-Hydroxymetoprolol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0g4j-9660000000-e1e9172ae97c378b1032	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - alpha-Hydroxymetoprolol GC-MS (2 TMS) - 70eV, Positive	splash10-00di-9412200000-dc0a050c4c5172ee4ee0	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - alpha-Hydroxymetoprolol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Hydroxymetoprolol 10V, Positive-QTOF	splash10-001i-1290000000-c263e920644986985034	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Hydroxymetoprolol 20V, Positive-QTOF	splash10-00xr-7590000000-728d839fd2e674e4d5d1	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Hydroxymetoprolol 40V, Positive-QTOF	splash10-00di-9400000000-2e611da703deefc1f44e	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Hydroxymetoprolol 10V, Negative-QTOF	splash10-00lr-1690000000-c364da9897e5fbb510cc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Hydroxymetoprolol 20V, Negative-QTOF	splash10-014l-5910000000-ef33561583618bd8d3ca	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Hydroxymetoprolol 40V, Negative-QTOF	splash10-0006-9600000000-f1d438a2ca75b083d463	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Hydroxymetoprolol 10V, Positive-QTOF	splash10-001i-0090000000-eb9370b59c0f91e97b69	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Hydroxymetoprolol 20V, Positive-QTOF	splash10-00xr-9470000000-3155302725eaaade152c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Hydroxymetoprolol 40V, Positive-QTOF	splash10-05fr-9200000000-aa52c785182011a5d0b0	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Hydroxymetoprolol 10V, Negative-QTOF	splash10-001i-0290000000-0465161f5ff9467d5305	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Hydroxymetoprolol 20V, Negative-QTOF	splash10-0079-1910000000-e506686ee47d7b59675e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Hydroxymetoprolol 40V, Negative-QTOF	splash10-000b-1900000000-851c2b41d16c8197b021	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

114962

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

Not Available

Showing metabocard for alpha-Hydroxymetoprolol (HMDB0060994)

MOL for HMDB0060994 (alpha-Hydroxymetoprolol)

3D MOL for HMDB0060994 (alpha-Hydroxymetoprolol)

3D SDF for HMDB0060994 (alpha-Hydroxymetoprolol)

3D-SDF for HMDB0060994 (alpha-Hydroxymetoprolol)

PDB for HMDB0060994 (alpha-Hydroxymetoprolol)

3D PDB for HMDB0060994 (alpha-Hydroxymetoprolol)

SMILES for HMDB0060994 (alpha-Hydroxymetoprolol)

INCHI for HMDB0060994 (alpha-Hydroxymetoprolol)

Structure for HMDB0060994 (alpha-Hydroxymetoprolol)

3D Structure for HMDB0060994 (alpha-Hydroxymetoprolol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra