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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-07-09 16:11:15 UTC

Update Date

2021-09-14 15:46:31 UTC

HMDB ID

HMDB0060989

Secondary Accession Numbers

HMDB60989

Metabolite Identification

Common Name

4'-hydroxypropanolol

Description

4'-hydroxypropanolol is a metabolite of propranolol. Propranolol is a sympatholytic non-selective beta blocker. Sympatholytics are used to treat hypertension, anxiety and panic. It was the first successful beta blocker developed. Propranolol is available in generic form as propranolol hydrochloride, as well as an AstraZeneca and Wyeth product under the brand names Inderal, Inderal LA, Avlocardyl, Deralin, Dociton, Inderalici, InnoPran XL, Sumial, Anaprilinum, Bedranol SR. (Wikipedia)

Structure

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

HMDB0060989
     RDKit          3D
4'-hydroxypropanolol
 41 42  0  0  0  0  0  0  0  0999 V2000
    5.5482    0.6006   -0.4381 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6255   -0.4280    0.1787 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1978   -0.9359    1.4837 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3175    0.1439    0.3927 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7379    0.5110   -0.8637 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3859    1.1477   -0.7765 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3685    2.3096   -0.0480 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3776    0.1248   -0.3416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9529    0.6155   -0.4477 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0036   -0.2013   -0.0906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8302   -1.4879    0.3717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9042   -2.2787    0.7194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2131   -1.7936    0.6123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2774   -2.5973    0.9649 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3824   -0.4987    0.1467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6407    0.0608    0.0091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8111    1.3674   -0.4611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7335    2.1448   -0.8039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4916    1.5860   -0.6658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2884    0.2844   -0.1993 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2843    1.6051   -0.0406 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4110    0.5582   -1.5363 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5888    0.3093   -0.1464 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5859   -1.2708   -0.5292 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8028   -1.8530    1.3504 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8198   -0.1345    1.9652 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3884   -1.1423    2.2087 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3287    0.8820    1.1075 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4634    1.1725   -1.4086 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7081   -0.4391   -1.4783 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0901    1.4228   -1.8362 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1029    2.1984    0.9008 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5840   -0.2197    0.6967 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4392   -0.7295   -1.0749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8284   -1.9050    0.4706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7589   -3.2827    1.0789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2209   -2.3107    0.9114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5109   -0.5241    0.2708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8081    1.7560   -0.5498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8718    3.1587   -1.1676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6281    2.2039   -0.9363 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
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 10  1  0
 20 15  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  3 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  7 32  1  0
  8 33  1  0
  8 34  1  0
 11 35  1  0
 12 36  1  0
 14 37  1  0
 16 38  1  0
 17 39  1  0
 18 40  1  0
 19 41  1  0
M  END


  Mrv0541 07091309112D          

 20 21  0  0  0  0            999 V2000
    5.7158   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.0625    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    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
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    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
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    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
   -0.7145   -1.2375    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
   -0.7145   -2.0625    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
    4.2868   -0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 O   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
    1.4289   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  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  9  1  0  0  0  0
 12 10  1  0  0  0  0
 13  5  2  0  0  0  0
 14  6  2  0  0  0  0
 14 13  1  0  0  0  0
 15  7  2  0  0  0  0
 15 13  1  0  0  0  0
 16  8  2  0  0  0  0
 16 14  1  0  0  0  0
 17  9  1  0  0  0  0
 17 11  1  0  0  0  0
 18 12  1  0  0  0  0
 19 15  1  0  0  0  0
 20 10  1  0  0  0  0
 20 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060989

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)NCC(O)COC1=CC=C(O)C2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C16H21NO3/c1-11(2)17-9-12(18)10-20-16-8-7-15(19)13-5-3-4-6-14(13)16/h3-8,11-12,17-19H,9-10H2,1-2H3

> <INCHI_KEY>
CWEPACWBWIOYID-UHFFFAOYSA-N

> <FORMULA>
C16H21NO3

> <MOLECULAR_WEIGHT>
275.3428

> <EXACT_MASS>
275.152143543

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
30.789079670337088

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-{2-hydroxy-3-[(propan-2-yl)amino]propoxy}naphthalen-1-ol

> <ALOGPS_LOGP>
1.63

> <JCHEM_LOGP>
1.5727338287143204

> <ALOGPS_LOGS>
-3.34

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.087943340442305

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.301042836344411

> <JCHEM_PKA_STRONGEST_BASIC>
9.912127928928367

> <JCHEM_POLAR_SURFACE_AREA>
61.72

> <JCHEM_REFRACTIVITY>
78.8066

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.24e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-[2-hydroxy-3-(isopropylamino)propoxy]naphthalen-1-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060989
     RDKit          3D
4'-hydroxypropanolol
 41 42  0  0  0  0  0  0  0  0999 V2000
    5.5482    0.6006   -0.4381 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6255   -0.4280    0.1787 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1978   -0.9359    1.4837 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3175    0.1439    0.3927 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7379    0.5110   -0.8637 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3859    1.1477   -0.7765 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3685    2.3096   -0.0480 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3776    0.1248   -0.3416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9529    0.6155   -0.4477 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0036   -0.2013   -0.0906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8302   -1.4879    0.3717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9042   -2.2787    0.7194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2131   -1.7936    0.6123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2774   -2.5973    0.9649 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3824   -0.4987    0.1467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6407    0.0608    0.0091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8111    1.3674   -0.4611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7335    2.1448   -0.8039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4916    1.5860   -0.6658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2884    0.2844   -0.1993 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2843    1.6051   -0.0406 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4110    0.5582   -1.5363 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5888    0.3093   -0.1464 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5859   -1.2708   -0.5292 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8028   -1.8530    1.3504 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8198   -0.1345    1.9652 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3884   -1.1423    2.2087 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3287    0.8820    1.1075 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4634    1.1725   -1.4086 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7081   -0.4391   -1.4783 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0901    1.4228   -1.8362 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1029    2.1984    0.9008 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5840   -0.2197    0.6967 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4392   -0.7295   -1.0749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8284   -1.9050    0.4706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7589   -3.2827    1.0789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2209   -2.3107    0.9114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5109   -0.5241    0.2708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8081    1.7560   -0.5498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8718    3.1587   -1.1676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6281    2.2039   -0.9363 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
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 10  1  0
 20 15  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  3 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  7 32  1  0
  8 33  1  0
  8 34  1  0
 11 35  1  0
 12 36  1  0
 14 37  1  0
 16 38  1  0
 17 39  1  0
 18 40  1  0
 19 41  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      10.669  -1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.336  -3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334   0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.667  -1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000  -4.620   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       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335  -1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000  -1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.334  -3.850   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       8.002  -1.540   0.000  0.00  0.00           N+0
HETATM   18  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       2.667  -1.540   0.000  0.00  0.00           O+0
CONECT    1   11                                                            
CONECT    2   11                                                            
CONECT    3    4    5                                                       
CONECT    4    3    6                                                       
CONECT    5    3   13                                                       
CONECT    6    4   14                                                       
CONECT    7    8   15                                                       
CONECT    8    7   16                                                       
CONECT    9   12   17                                                       
CONECT   10   12   20                                                       
CONECT   11    1    2   17                                                  
CONECT   12    9   10   18                                                  
CONECT   13    5   14   15                                                  
CONECT   14    6   13   16                                                  
CONECT   15    7   13   19                                                  
CONECT   16    8   14   20                                                  
CONECT   17    9   11                                                       
CONECT   18   12                                                            
CONECT   19   15                                                            
CONECT   20   10   16                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

COMPND    HMDB0060989
HETATM    1  C1  UNL     1       5.548   0.601  -0.438  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.625  -0.428   0.179  1.00  0.00           C  
HETATM    3  C3  UNL     1       5.198  -0.936   1.484  1.00  0.00           C  
HETATM    4  N1  UNL     1       3.318   0.144   0.393  1.00  0.00           N  
HETATM    5  C4  UNL     1       2.738   0.511  -0.864  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.386   1.148  -0.777  1.00  0.00           C  
HETATM    7  O1  UNL     1       1.369   2.310  -0.048  1.00  0.00           O  
HETATM    8  C6  UNL     1       0.378   0.125  -0.342  1.00  0.00           C  
HETATM    9  O2  UNL     1      -0.953   0.616  -0.448  1.00  0.00           O  
HETATM   10  C7  UNL     1      -2.004  -0.201  -0.091  1.00  0.00           C  
HETATM   11  C8  UNL     1      -1.830  -1.488   0.372  1.00  0.00           C  
HETATM   12  C9  UNL     1      -2.904  -2.279   0.719  1.00  0.00           C  
HETATM   13  C10 UNL     1      -4.213  -1.794   0.612  1.00  0.00           C  
HETATM   14  O3  UNL     1      -5.277  -2.597   0.965  1.00  0.00           O  
HETATM   15  C11 UNL     1      -4.382  -0.499   0.147  1.00  0.00           C  
HETATM   16  C12 UNL     1      -5.641   0.061   0.009  1.00  0.00           C  
HETATM   17  C13 UNL     1      -5.811   1.367  -0.461  1.00  0.00           C  
HETATM   18  C14 UNL     1      -4.734   2.145  -0.804  1.00  0.00           C  
HETATM   19  C15 UNL     1      -3.492   1.586  -0.666  1.00  0.00           C  
HETATM   20  C16 UNL     1      -3.288   0.284  -0.199  1.00  0.00           C  
HETATM   21  H1  UNL     1       5.284   1.605  -0.041  1.00  0.00           H  
HETATM   22  H2  UNL     1       5.411   0.558  -1.536  1.00  0.00           H  
HETATM   23  H3  UNL     1       6.589   0.309  -0.146  1.00  0.00           H  
HETATM   24  H4  UNL     1       4.586  -1.271  -0.529  1.00  0.00           H  
HETATM   25  H5  UNL     1       5.803  -1.853   1.350  1.00  0.00           H  
HETATM   26  H6  UNL     1       5.820  -0.135   1.965  1.00  0.00           H  
HETATM   27  H7  UNL     1       4.388  -1.142   2.209  1.00  0.00           H  
HETATM   28  H8  UNL     1       3.329   0.882   1.108  1.00  0.00           H  
HETATM   29  H9  UNL     1       3.463   1.173  -1.409  1.00  0.00           H  
HETATM   30  H10 UNL     1       2.708  -0.439  -1.478  1.00  0.00           H  
HETATM   31  H11 UNL     1       1.090   1.423  -1.836  1.00  0.00           H  
HETATM   32  H12 UNL     1       1.103   2.198   0.901  1.00  0.00           H  
HETATM   33  H13 UNL     1       0.584  -0.220   0.697  1.00  0.00           H  
HETATM   34  H14 UNL     1       0.439  -0.729  -1.075  1.00  0.00           H  
HETATM   35  H15 UNL     1      -0.828  -1.905   0.471  1.00  0.00           H  
HETATM   36  H16 UNL     1      -2.759  -3.283   1.079  1.00  0.00           H  
HETATM   37  H17 UNL     1      -6.221  -2.311   0.911  1.00  0.00           H  
HETATM   38  H18 UNL     1      -6.511  -0.524   0.271  1.00  0.00           H  
HETATM   39  H19 UNL     1      -6.808   1.756  -0.550  1.00  0.00           H  
HETATM   40  H20 UNL     1      -4.872   3.159  -1.168  1.00  0.00           H  
HETATM   41  H21 UNL     1      -2.628   2.204  -0.936  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3    4   24
CONECT    3   25   26   27
CONECT    4    5   28
CONECT    5    6   29   30
CONECT    6    7    8   31
CONECT    7   32
CONECT    8    9   33   34
CONECT    9   10
CONECT   10   11   11   20
CONECT   11   12   35
CONECT   12   13   13   36
CONECT   13   14   15
CONECT   14   37
CONECT   15   16   16   20
CONECT   16   17   38
CONECT   17   18   18   39
CONECT   18   19   40
CONECT   19   20   20   41
END

HMDB0060989
     RDKit          3D
4'-hydroxypropanolol
 41 42  0  0  0  0  0  0  0  0999 V2000
    5.5482    0.6006   -0.4381 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6255   -0.4280    0.1787 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1978   -0.9359    1.4837 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3175    0.1439    0.3927 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7379    0.5110   -0.8637 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3859    1.1477   -0.7765 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3685    2.3096   -0.0480 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3776    0.1248   -0.3416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9529    0.6155   -0.4477 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0036   -0.2013   -0.0906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8302   -1.4879    0.3717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9042   -2.2787    0.7194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2131   -1.7936    0.6123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2774   -2.5973    0.9649 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3824   -0.4987    0.1467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6407    0.0608    0.0091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8111    1.3674   -0.4611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7335    2.1448   -0.8039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4916    1.5860   -0.6658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2884    0.2844   -0.1993 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2843    1.6051   -0.0406 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4110    0.5582   -1.5363 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5888    0.3093   -0.1464 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5859   -1.2708   -0.5292 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8028   -1.8530    1.3504 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8198   -0.1345    1.9652 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3884   -1.1423    2.2087 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3287    0.8820    1.1075 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4634    1.1725   -1.4086 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7081   -0.4391   -1.4783 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0901    1.4228   -1.8362 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1029    2.1984    0.9008 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5840   -0.2197    0.6967 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4392   -0.7295   -1.0749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8284   -1.9050    0.4706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7589   -3.2827    1.0789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2209   -2.3107    0.9114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5109   -0.5241    0.2708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8081    1.7560   -0.5498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8718    3.1587   -1.1676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6281    2.2039   -0.9363 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
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 10  1  0
 20 15  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  3 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  7 32  1  0
  8 33  1  0
  8 34  1  0
 11 35  1  0
 12 36  1  0
 14 37  1  0
 16 38  1  0
 17 39  1  0
 18 40  1  0
 19 41  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-Hydroxy propranolol	HMDB
4-HYDROXYPROPRANOLOL sulfuric acid	HMDB
4-HYDROXYPROPRANOLOL sulphate	HMDB
4-HYDROXYPROPRANOLOL sulphuric acid	HMDB
1-(4-Hydroxynaphth-1-yloxy)-3-isopropylamino-2- propanol	HMDB
4-Hydroxypropranolol, (R)-isomer	HMDB
4-Hydroxypropranolol, (S)-isomer	HMDB
4-Hydroxypropranolol hydrochloride	HMDB
4-Hydroxypropranolol hydrochloride, (+-)-isomer	HMDB
4-Hydroxypropranolol, (+-)-isomer	HMDB

Chemical Formula

C₁₆H₂₁NO₃

Average Molecular Weight

275.3428

Monoisotopic Molecular Weight

275.152143543

IUPAC Name

4-{2-hydroxy-3-[(propan-2-yl)amino]propoxy}naphthalen-1-ol

Traditional Name

4-[2-hydroxy-3-(isopropylamino)propoxy]naphthalen-1-ol

CAS Registry Number

Not Available

SMILES

CC(C)NCC(O)COC1=CC=C(O)C2=CC=CC=C12

InChI Identifier

InChI=1S/C16H21NO3/c1-11(2)17-9-12(18)10-20-16-8-7-15(19)13-5-3-4-6-14(13)16/h3-8,11-12,17-19H,9-10H2,1-2H3

InChI Key

CWEPACWBWIOYID-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthols and derivatives. These are naphthalene derivatives carrying one or more hydroxyl (-OH) groups at any ring position.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Naphthalenes

Sub Class

Naphthols and derivatives

Direct Parent

Naphthols and derivatives

Alternative Parents

Substituents

1-naphthol
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
1,2-aminoalcohol
Secondary alcohol
Secondary aliphatic amine
Ether
Secondary amine
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organopnictogen compound
Amine
Organic oxygen compound
Alcohol
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Kidney (HMDB: HMDB0060989)
Liver (HMDB: HMDB0060989)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060989)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060989)

Cellular substructure

Cytoplasm (HMDB: HMDB0060989)

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	0.12 g/L	ALOGPS
logP	1.63	ALOGPS
logP	1.57	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	9.3	ChemAxon
pKa (Strongest Basic)	9.91	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	6	ChemAxon
Refractivity	78.81 m³·mol⁻¹	ChemAxon
Polarizability	30.79 Å³	ChemAxon
Number of Rings	2	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]+	163.518	31661259
DarkChem	[M-H]-	161.821	31661259
DeepCCS	[M-2H]-	195.082	30932474
DeepCCS	[M+Na]+	170.647	30932474
AllCCS	[M+H]+	166.3	32859911
AllCCS	[M+H-H2O]+	163.0	32859911
AllCCS	[M+NH4]+	169.4	32859911
AllCCS	[M+Na]+	170.3	32859911
AllCCS	[M-H]-	168.9	32859911
AllCCS	[M+Na-2H]-	169.1	32859911
AllCCS	[M+HCOO]-	169.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4'-hydroxypropanolol	CC(C)NCC(O)COC1=CC=C(O)C2=CC=CC=C12	3363.2	Standard polar	33892256
4'-hydroxypropanolol	CC(C)NCC(O)COC1=CC=C(O)C2=CC=CC=C12	2352.8	Standard non polar	33892256
4'-hydroxypropanolol	CC(C)NCC(O)COC1=CC=C(O)C2=CC=CC=C12	2416.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4'-hydroxypropanolol,1TMS,isomer #1	CC(C)NCC(COC1=CC=C(O)C2=CC=CC=C12)O[Si](C)(C)C	2475.4	Semi standard non polar	33892256
4'-hydroxypropanolol,1TMS,isomer #2	CC(C)NCC(O)COC1=CC=C(O[Si](C)(C)C)C2=CC=CC=C12	2443.1	Semi standard non polar	33892256
4'-hydroxypropanolol,1TMS,isomer #3	CC(C)N(CC(O)COC1=CC=C(O)C2=CC=CC=C12)[Si](C)(C)C	2602.7	Semi standard non polar	33892256
4'-hydroxypropanolol,2TMS,isomer #1	CC(C)NCC(COC1=CC=C(O[Si](C)(C)C)C2=CC=CC=C12)O[Si](C)(C)C	2391.7	Semi standard non polar	33892256
4'-hydroxypropanolol,2TMS,isomer #2	CC(C)N(CC(COC1=CC=C(O)C2=CC=CC=C12)O[Si](C)(C)C)[Si](C)(C)C	2648.4	Semi standard non polar	33892256
4'-hydroxypropanolol,2TMS,isomer #3	CC(C)N(CC(O)COC1=CC=C(O[Si](C)(C)C)C2=CC=CC=C12)[Si](C)(C)C	2575.0	Semi standard non polar	33892256
4'-hydroxypropanolol,3TMS,isomer #1	CC(C)N(CC(COC1=CC=C(O[Si](C)(C)C)C2=CC=CC=C12)O[Si](C)(C)C)[Si](C)(C)C	2610.3	Semi standard non polar	33892256
4'-hydroxypropanolol,3TMS,isomer #1	CC(C)N(CC(COC1=CC=C(O[Si](C)(C)C)C2=CC=CC=C12)O[Si](C)(C)C)[Si](C)(C)C	2590.4	Standard non polar	33892256
4'-hydroxypropanolol,3TMS,isomer #1	CC(C)N(CC(COC1=CC=C(O[Si](C)(C)C)C2=CC=CC=C12)O[Si](C)(C)C)[Si](C)(C)C	2734.1	Standard polar	33892256
4'-hydroxypropanolol,1TBDMS,isomer #1	CC(C)NCC(COC1=CC=C(O)C2=CC=CC=C12)O[Si](C)(C)C(C)(C)C	2731.0	Semi standard non polar	33892256
4'-hydroxypropanolol,1TBDMS,isomer #2	CC(C)NCC(O)COC1=CC=C(O[Si](C)(C)C(C)(C)C)C2=CC=CC=C12	2718.9	Semi standard non polar	33892256
4'-hydroxypropanolol,1TBDMS,isomer #3	CC(C)N(CC(O)COC1=CC=C(O)C2=CC=CC=C12)[Si](C)(C)C(C)(C)C	2863.4	Semi standard non polar	33892256
4'-hydroxypropanolol,2TBDMS,isomer #1	CC(C)NCC(COC1=CC=C(O[Si](C)(C)C(C)(C)C)C2=CC=CC=C12)O[Si](C)(C)C(C)(C)C	2880.5	Semi standard non polar	33892256
4'-hydroxypropanolol,2TBDMS,isomer #2	CC(C)N(CC(COC1=CC=C(O)C2=CC=CC=C12)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3118.1	Semi standard non polar	33892256
4'-hydroxypropanolol,2TBDMS,isomer #3	CC(C)N(CC(O)COC1=CC=C(O[Si](C)(C)C(C)(C)C)C2=CC=CC=C12)[Si](C)(C)C(C)(C)C	3084.1	Semi standard non polar	33892256
4'-hydroxypropanolol,3TBDMS,isomer #1	CC(C)N(CC(COC1=CC=C(O[Si](C)(C)C(C)(C)C)C2=CC=CC=C12)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3291.8	Semi standard non polar	33892256
4'-hydroxypropanolol,3TBDMS,isomer #1	CC(C)N(CC(COC1=CC=C(O[Si](C)(C)C(C)(C)C)C2=CC=CC=C12)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3175.5	Standard non polar	33892256
4'-hydroxypropanolol,3TBDMS,isomer #1	CC(C)N(CC(COC1=CC=C(O[Si](C)(C)C(C)(C)C)C2=CC=CC=C12)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3009.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4'-hydroxypropanolol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0759-9610000000-a9018aef243706ee9894	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4'-hydroxypropanolol GC-MS (2 TMS) - 70eV, Positive	splash10-0g4i-9253300000-e397bbaa4c4dbe33005b	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4'-hydroxypropanolol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4'-hydroxypropanolol 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 - 4'-hydroxypropanolol 10V, Positive-QTOF	splash10-004i-1190000000-6d6d2f69c29c5e9841be	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4'-hydroxypropanolol 20V, Positive-QTOF	splash10-00xr-8490000000-21dbe2d2312cf3ec034b	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4'-hydroxypropanolol 40V, Positive-QTOF	splash10-05gi-9300000000-d9a8363f652f70d55a9f	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4'-hydroxypropanolol 10V, Negative-QTOF	splash10-05fr-1690000000-ff5bb68f749a06ea9fcd	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4'-hydroxypropanolol 20V, Negative-QTOF	splash10-0a4i-0900000000-795ea8788211bcca170e	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4'-hydroxypropanolol 40V, Negative-QTOF	splash10-0a4i-0900000000-e2b9d74bb51e694a4856	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4'-hydroxypropanolol 10V, Positive-QTOF	splash10-004i-0090000000-ce6120337226cb43c4c7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4'-hydroxypropanolol 20V, Positive-QTOF	splash10-00tb-8690000000-f8588013d872e030c139	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4'-hydroxypropanolol 40V, Positive-QTOF	splash10-0a4i-9200000000-27cf42b6e98044df3f67	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4'-hydroxypropanolol 10V, Negative-QTOF	splash10-00di-0930000000-43448593777c6d80ad64	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4'-hydroxypropanolol 20V, Negative-QTOF	splash10-0a4i-1900000000-dc352582aa68187e2735	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4'-hydroxypropanolol 40V, Negative-QTOF	splash10-0a4i-3900000000-eabf6f73a10e417acc95	2021-09-25	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

91565

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 4'-hydroxypropanolol (HMDB0060989)

MOL for HMDB0060989 (4'-hydroxypropanolol)

3D MOL for HMDB0060989 (4'-hydroxypropanolol)

3D SDF for HMDB0060989 (4'-hydroxypropanolol)

3D-SDF for HMDB0060989 (4'-hydroxypropanolol)

PDB for HMDB0060989 (4'-hydroxypropanolol)

3D PDB for HMDB0060989 (4'-hydroxypropanolol)

SMILES for HMDB0060989 (4'-hydroxypropanolol)

INCHI for HMDB0060989 (4'-hydroxypropanolol)

Structure for HMDB0060989 (4'-hydroxypropanolol)

3D Structure for HMDB0060989 (4'-hydroxypropanolol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra