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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-07-22 19:49:12 UTC

Update Date

2021-09-14 15:46:31 UTC

HMDB ID

HMDB0061122

Secondary Accession Numbers

HMDB61122

Metabolite Identification

Common Name

4-Hydroxy-alprenolol

Description

4-Hydroxy-alprenolol is a metabolite of alprenolol. Alprenolol, or alfeprol, alpheprol, and alprenololum (Gubernal, Regletin, Yobir, Apllobal, Aptine, Aptol Duriles), is a non-selective beta blocker as well as 5-HT1A receptor antagonist, used in the treatment of angina pectoris. It is no longer marketed by AstraZeneca, but may still be available from other pharmaceutical companies or generically. (Wikipedia)

Structure

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

HMDB0061122
     RDKit          3D
4-Hydroxy-alprenolol
 42 42  0  0  0  0  0  0  0  0999 V2000
   -2.5351    2.7580   -1.2835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4529    1.8144   -1.2023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8401    1.3009    0.1221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5691   -0.1413    0.2784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5486   -1.0755    0.2052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2941   -2.4209    0.3410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2981   -3.3832    0.2655 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0126   -2.8599    0.5597 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9822   -1.9225    0.6409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2367   -0.5706    0.5035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3047    0.3645    0.5740 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0241    0.4578    0.7334 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9451   -0.0692   -0.3251 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8814   -1.4007   -0.6107 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3719    0.2823    0.1002 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2699   -0.0163   -0.9796 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6116    0.3492   -0.5834 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0787   -0.4599    0.5818 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6288    1.8373   -0.3010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1924    3.1921   -2.2244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0865    3.1323   -0.3763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8935    1.4485   -2.1337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9282    1.5019    0.2395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3358    1.9109    0.8988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5782   -0.7450    0.0323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5185   -3.7810   -0.6433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7664   -3.9136    0.6718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9938   -2.3288    0.8420 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2742    1.5489    0.9444 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4020   -0.0417    1.7026 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7317    0.4590   -1.3194 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2641   -1.9042    0.1598 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5704   -0.3287    1.0153 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3935    1.3399    0.3935 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2354   -1.0236   -1.2454 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2831    0.1542   -1.4743 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0264   -1.0083    0.2987 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2568    0.1941    1.4650 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3605   -1.2724    0.8205 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3216    2.0176    0.7448 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5996    2.3068   -0.4857 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8367    2.2966   -0.9509 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 10  4  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  5 25  1  0
  7 26  1  0
  8 27  1  0
  9 28  1  0
 12 29  1  0
 12 30  1  0
 13 31  1  0
 14 32  1  0
 15 33  1  0
 15 34  1  0
 16 35  1  0
 17 36  1  0
 18 37  1  0
 18 38  1  0
 18 39  1  0
 19 40  1  0
 19 41  1  0
 19 42  1  0
M  END

  Mrv0541 07221312492D          

 19 19  0  0  0  0            999 V2000
   -0.8250   -0.7323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2332   -0.0251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.7323    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2332   -1.4394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0626   -0.0251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8076    0.7017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4103   -1.4394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0626   -1.4394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4729   -0.7323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2266    1.4307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2353   -1.4394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8076    2.1510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6457   -0.7323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6457   -2.1510    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2353   -0.0251    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6457    0.6842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2353    1.3936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4729    0.6842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2979   -0.7323    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  2  0  0  0  0
  2  5  2  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
  4  8  1  0  0  0  0
  5  9  1  0  0  0  0
  6 10  1  0  0  0  0
  7 11  1  0  0  0  0
  8  9  2  0  0  0  0
 10 12  2  0  0  0  0
 11 13  1  0  0  0  0
 11 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
  9 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0061122

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)NCC(O)COC1=CC=C(O)C=C1CC=C

> <INCHI_IDENTIFIER>
InChI=1S/C15H23NO3/c1-4-5-12-8-13(17)6-7-15(12)19-10-14(18)9-16-11(2)3/h4,6-8,11,14,16-18H,1,5,9-10H2,2-3H3

> <INCHI_KEY>
HNXRWPIZRBNFDD-UHFFFAOYSA-N

> <FORMULA>
C15H23NO3

> <MOLECULAR_WEIGHT>
265.348

> <EXACT_MASS>
265.167793607

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
30.384025954958048

> <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}-3-(prop-2-en-1-yl)phenol

> <ALOGPS_LOGP>
1.52

> <JCHEM_LOGP>
1.859338248650214

> <ALOGPS_LOGS>
-2.43

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.08797767653665

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.066535489681012

> <JCHEM_PKA_STRONGEST_BASIC>
9.445426118802299

> <JCHEM_POLAR_SURFACE_AREA>
61.72

> <JCHEM_REFRACTIVITY>
76.64370000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.95e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-[2-hydroxy-3-(isopropylamino)propoxy]-3-(prop-2-en-1-yl)phenol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0061122
     RDKit          3D
4-Hydroxy-alprenolol
 42 42  0  0  0  0  0  0  0  0999 V2000
   -2.5351    2.7580   -1.2835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4529    1.8144   -1.2023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8401    1.3009    0.1221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5691   -0.1413    0.2784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5486   -1.0755    0.2052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2941   -2.4209    0.3410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2981   -3.3832    0.2655 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0126   -2.8599    0.5597 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9822   -1.9225    0.6409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2367   -0.5706    0.5035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3047    0.3645    0.5740 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0241    0.4578    0.7334 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9451   -0.0692   -0.3251 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8814   -1.4007   -0.6107 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3719    0.2823    0.1002 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2699   -0.0163   -0.9796 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6116    0.3492   -0.5834 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0787   -0.4599    0.5818 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6288    1.8373   -0.3010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1924    3.1921   -2.2244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0865    3.1323   -0.3763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8935    1.4485   -2.1337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9282    1.5019    0.2395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3358    1.9109    0.8988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5782   -0.7450    0.0323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5185   -3.7810   -0.6433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7664   -3.9136    0.6718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9938   -2.3288    0.8420 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2742    1.5489    0.9444 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4020   -0.0417    1.7026 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7317    0.4590   -1.3194 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2641   -1.9042    0.1598 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5704   -0.3287    1.0153 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3935    1.3399    0.3935 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2354   -1.0236   -1.2454 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2831    0.1542   -1.4743 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0264   -1.0083    0.2987 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2568    0.1941    1.4650 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3605   -1.2724    0.8205 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3216    2.0176    0.7448 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5996    2.3068   -0.4857 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8367    2.2966   -0.9509 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 10  4  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  5 25  1  0
  7 26  1  0
  8 27  1  0
  9 28  1  0
 12 29  1  0
 12 30  1  0
 13 31  1  0
 14 32  1  0
 15 33  1  0
 15 34  1  0
 16 35  1  0
 17 36  1  0
 18 37  1  0
 18 38  1  0
 18 39  1  0
 19 40  1  0
 19 41  1  0
 19 42  1  0
M  END

HEADER    PROTEIN                                 22-JUL-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-JUL-13         0                                  
HETATM    1  C   UNK     0      -1.540  -1.367   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.302  -0.047   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.000  -1.367   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -2.302  -2.687   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.850  -0.047   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.508   1.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.766  -2.687   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.850  -2.687   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.616  -1.367   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.290   2.671   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.306  -2.687   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.508   4.015   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.072  -1.367   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       3.072  -4.015   0.000  0.00  0.00           O+0
HETATM   15  N   UNK     0       2.306  -0.047   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0       3.072   1.277   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.306   2.601   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.616   1.277   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -6.156  -1.367   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6                                                  
CONECT    3    1    7                                                       
CONECT    4    1    8                                                       
CONECT    5    2    9                                                       
CONECT    6    2   10                                                       
CONECT    7    3   11                                                       
CONECT    8    4    9                                                       
CONECT    9    5    8   19                                                  
CONECT   10    6   12                                                       
CONECT   11    7   13   14                                                  
CONECT   12   10                                                            
CONECT   13   11   15                                                       
CONECT   14   11                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19    9                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   38    0
END

COMPND    HMDB0061122
HETATM    1  C1  UNL     1      -2.535   2.758  -1.284  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.453   1.814  -1.202  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.840   1.301   0.122  1.00  0.00           C  
HETATM    4  C4  UNL     1      -3.569  -0.141   0.278  1.00  0.00           C  
HETATM    5  C5  UNL     1      -4.549  -1.076   0.205  1.00  0.00           C  
HETATM    6  C6  UNL     1      -4.294  -2.421   0.341  1.00  0.00           C  
HETATM    7  O1  UNL     1      -5.298  -3.383   0.266  1.00  0.00           O  
HETATM    8  C7  UNL     1      -3.013  -2.860   0.560  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.982  -1.922   0.641  1.00  0.00           C  
HETATM   10  C9  UNL     1      -2.237  -0.571   0.503  1.00  0.00           C  
HETATM   11  O2  UNL     1      -1.305   0.364   0.574  1.00  0.00           O  
HETATM   12  C10 UNL     1       0.024   0.458   0.733  1.00  0.00           C  
HETATM   13  C11 UNL     1       0.945  -0.069  -0.325  1.00  0.00           C  
HETATM   14  O3  UNL     1       0.881  -1.401  -0.611  1.00  0.00           O  
HETATM   15  C12 UNL     1       2.372   0.282   0.100  1.00  0.00           C  
HETATM   16  N1  UNL     1       3.270  -0.016  -0.980  1.00  0.00           N  
HETATM   17  C13 UNL     1       4.612   0.349  -0.583  1.00  0.00           C  
HETATM   18  C14 UNL     1       5.079  -0.460   0.582  1.00  0.00           C  
HETATM   19  C15 UNL     1       4.629   1.837  -0.301  1.00  0.00           C  
HETATM   20  H1  UNL     1      -2.192   3.192  -2.224  1.00  0.00           H  
HETATM   21  H2  UNL     1      -2.087   3.132  -0.376  1.00  0.00           H  
HETATM   22  H3  UNL     1      -3.893   1.448  -2.134  1.00  0.00           H  
HETATM   23  H4  UNL     1      -4.928   1.502   0.240  1.00  0.00           H  
HETATM   24  H5  UNL     1      -3.336   1.911   0.899  1.00  0.00           H  
HETATM   25  H6  UNL     1      -5.578  -0.745   0.032  1.00  0.00           H  
HETATM   26  H7  UNL     1      -5.519  -3.781  -0.643  1.00  0.00           H  
HETATM   27  H8  UNL     1      -2.766  -3.914   0.672  1.00  0.00           H  
HETATM   28  H9  UNL     1      -0.994  -2.329   0.842  1.00  0.00           H  
HETATM   29  H10 UNL     1       0.274   1.549   0.944  1.00  0.00           H  
HETATM   30  H11 UNL     1       0.402  -0.042   1.703  1.00  0.00           H  
HETATM   31  H12 UNL     1       0.732   0.459  -1.319  1.00  0.00           H  
HETATM   32  H13 UNL     1       1.264  -1.904   0.160  1.00  0.00           H  
HETATM   33  H14 UNL     1       2.570  -0.329   1.015  1.00  0.00           H  
HETATM   34  H15 UNL     1       2.393   1.340   0.393  1.00  0.00           H  
HETATM   35  H16 UNL     1       3.235  -1.024  -1.245  1.00  0.00           H  
HETATM   36  H17 UNL     1       5.283   0.154  -1.474  1.00  0.00           H  
HETATM   37  H18 UNL     1       6.026  -1.008   0.299  1.00  0.00           H  
HETATM   38  H19 UNL     1       5.257   0.194   1.465  1.00  0.00           H  
HETATM   39  H20 UNL     1       4.360  -1.272   0.820  1.00  0.00           H  
HETATM   40  H21 UNL     1       4.322   2.018   0.745  1.00  0.00           H  
HETATM   41  H22 UNL     1       5.600   2.307  -0.486  1.00  0.00           H  
HETATM   42  H23 UNL     1       3.837   2.297  -0.951  1.00  0.00           H  
CONECT    1    2    2   20   21
CONECT    2    3   22
CONECT    3    4   23   24
CONECT    4    5    5   10
CONECT    5    6   25
CONECT    6    7    8    8
CONECT    7   26
CONECT    8    9   27
CONECT    9   10   10   28
CONECT   10   11
CONECT   11   12
CONECT   12   13   29   30
CONECT   13   14   15   31
CONECT   14   32
CONECT   15   16   33   34
CONECT   16   17   35
CONECT   17   18   19   36
CONECT   18   37   38   39
CONECT   19   40   41   42
END

HMDB0061122
     RDKit          3D
4-Hydroxy-alprenolol
 42 42  0  0  0  0  0  0  0  0999 V2000
   -2.5351    2.7580   -1.2835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4529    1.8144   -1.2023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8401    1.3009    0.1221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5691   -0.1413    0.2784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5486   -1.0755    0.2052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2941   -2.4209    0.3410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2981   -3.3832    0.2655 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0126   -2.8599    0.5597 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9822   -1.9225    0.6409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2367   -0.5706    0.5035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3047    0.3645    0.5740 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0241    0.4578    0.7334 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9451   -0.0692   -0.3251 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8814   -1.4007   -0.6107 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3719    0.2823    0.1002 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2699   -0.0163   -0.9796 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6116    0.3492   -0.5834 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0787   -0.4599    0.5818 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6288    1.8373   -0.3010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1924    3.1921   -2.2244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0865    3.1323   -0.3763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8935    1.4485   -2.1337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9282    1.5019    0.2395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3358    1.9109    0.8988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5782   -0.7450    0.0323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5185   -3.7810   -0.6433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7664   -3.9136    0.6718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9938   -2.3288    0.8420 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2742    1.5489    0.9444 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4020   -0.0417    1.7026 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7317    0.4590   -1.3194 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2641   -1.9042    0.1598 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5704   -0.3287    1.0153 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3935    1.3399    0.3935 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2354   -1.0236   -1.2454 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2831    0.1542   -1.4743 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0264   -1.0083    0.2987 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2568    0.1941    1.4650 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3605   -1.2724    0.8205 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3216    2.0176    0.7448 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5996    2.3068   -0.4857 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8367    2.2966   -0.9509 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 10  4  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  5 25  1  0
  7 26  1  0
  8 27  1  0
  9 28  1  0
 12 29  1  0
 12 30  1  0
 13 31  1  0
 14 32  1  0
 15 33  1  0
 15 34  1  0
 16 35  1  0
 17 36  1  0
 18 37  1  0
 18 38  1  0
 18 39  1  0
 19 40  1  0
 19 41  1  0
 19 42  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-Hydroxyalprenolol, (+-)-isomer	HMDB
4-Hydroxyalprenolol hydrochloride	HMDB
4-Hydroxyalprenolol	MeSH

Chemical Formula

C₁₅H₂₃NO₃

Average Molecular Weight

265.348

Monoisotopic Molecular Weight

265.167793607

IUPAC Name

4-{2-hydroxy-3-[(propan-2-yl)amino]propoxy}-3-(prop-2-en-1-yl)phenol

Traditional Name

4-[2-hydroxy-3-(isopropylamino)propoxy]-3-(prop-2-en-1-yl)phenol

CAS Registry Number

Not Available

SMILES

CC(C)NCC(O)COC1=CC=C(O)C=C1CC=C

InChI Identifier

InChI=1S/C15H23NO3/c1-4-5-12-8-13(17)6-7-15(12)19-10-14(18)9-16-11(2)3/h4,6-8,11,14,16-18H,1,5,9-10H2,2-3H3

InChI Key

HNXRWPIZRBNFDD-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 4-alkoxyphenols. These are phenols that carry an alkoxy group at the 4-position of the benzene ring.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

4-alkoxyphenol
Phenoxy compound
Phenol ether
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Secondary alcohol
1,2-aminoalcohol
Secondary amine
Ether
Secondary aliphatic amine
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Amine
Organic nitrogen compound
Alcohol
Organopnictogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0061122)

Organ

Liver (HMDB: HMDB0061122)
Kidney (HMDB: HMDB0061122)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0061122)

Cellular substructure

Cytoplasm (HMDB: HMDB0061122)

Source

Endogenous

Endogenous (HMDB: HMDB0061122)

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 g/L	ALOGPS
logP	1.52	ALOGPS
logP	1.86	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	10.07	ChemAxon
pKa (Strongest Basic)	9.45	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	76.64 m³·mol⁻¹	ChemAxon
Polarizability	30.38 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]+	160.515	31661259
DarkChem	[M-H]-	160.573	31661259
DeepCCS	[M+H]+	162.324	30932474
DeepCCS	[M-H]-	159.966	30932474
DeepCCS	[M-2H]-	193.313	30932474
DeepCCS	[M+Na]+	168.479	30932474
AllCCS	[M+H]+	165.6	32859911
AllCCS	[M+H-H2O]+	162.2	32859911
AllCCS	[M+NH4]+	168.7	32859911
AllCCS	[M+Na]+	169.6	32859911
AllCCS	[M-H]-	166.6	32859911
AllCCS	[M+Na-2H]-	167.1	32859911
AllCCS	[M+HCOO]-	167.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Hydroxy-alprenolol	CC(C)NCC(O)COC1=CC=C(O)C=C1CC=C	3255.1	Standard polar	33892256
4-Hydroxy-alprenolol	CC(C)NCC(O)COC1=CC=C(O)C=C1CC=C	2191.2	Standard non polar	33892256
4-Hydroxy-alprenolol	CC(C)NCC(O)COC1=CC=C(O)C=C1CC=C	2163.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-Hydroxy-alprenolol,1TMS,isomer #1	C=CCC1=CC(O)=CC=C1OCC(CNC(C)C)O[Si](C)(C)C	2160.8	Semi standard non polar	33892256
4-Hydroxy-alprenolol,1TMS,isomer #2	C=CCC1=CC(O[Si](C)(C)C)=CC=C1OCC(O)CNC(C)C	2109.7	Semi standard non polar	33892256
4-Hydroxy-alprenolol,1TMS,isomer #3	C=CCC1=CC(O)=CC=C1OCC(O)CN(C(C)C)[Si](C)(C)C	2310.5	Semi standard non polar	33892256
4-Hydroxy-alprenolol,2TMS,isomer #1	C=CCC1=CC(O[Si](C)(C)C)=CC=C1OCC(CNC(C)C)O[Si](C)(C)C	2093.9	Semi standard non polar	33892256
4-Hydroxy-alprenolol,2TMS,isomer #2	C=CCC1=CC(O)=CC=C1OCC(CN(C(C)C)[Si](C)(C)C)O[Si](C)(C)C	2334.5	Semi standard non polar	33892256
4-Hydroxy-alprenolol,2TMS,isomer #3	C=CCC1=CC(O[Si](C)(C)C)=CC=C1OCC(O)CN(C(C)C)[Si](C)(C)C	2296.8	Semi standard non polar	33892256
4-Hydroxy-alprenolol,3TMS,isomer #1	C=CCC1=CC(O[Si](C)(C)C)=CC=C1OCC(CN(C(C)C)[Si](C)(C)C)O[Si](C)(C)C	2335.2	Semi standard non polar	33892256
4-Hydroxy-alprenolol,3TMS,isomer #1	C=CCC1=CC(O[Si](C)(C)C)=CC=C1OCC(CN(C(C)C)[Si](C)(C)C)O[Si](C)(C)C	2315.1	Standard non polar	33892256
4-Hydroxy-alprenolol,3TMS,isomer #1	C=CCC1=CC(O[Si](C)(C)C)=CC=C1OCC(CN(C(C)C)[Si](C)(C)C)O[Si](C)(C)C	2451.4	Standard polar	33892256
4-Hydroxy-alprenolol,1TBDMS,isomer #1	C=CCC1=CC(O)=CC=C1OCC(CNC(C)C)O[Si](C)(C)C(C)(C)C	2395.2	Semi standard non polar	33892256
4-Hydroxy-alprenolol,1TBDMS,isomer #2	C=CCC1=CC(O[Si](C)(C)C(C)(C)C)=CC=C1OCC(O)CNC(C)C	2346.0	Semi standard non polar	33892256
4-Hydroxy-alprenolol,1TBDMS,isomer #3	C=CCC1=CC(O)=CC=C1OCC(O)CN(C(C)C)[Si](C)(C)C(C)(C)C	2560.0	Semi standard non polar	33892256
4-Hydroxy-alprenolol,2TBDMS,isomer #1	C=CCC1=CC(O[Si](C)(C)C(C)(C)C)=CC=C1OCC(CNC(C)C)O[Si](C)(C)C(C)(C)C	2533.3	Semi standard non polar	33892256
4-Hydroxy-alprenolol,2TBDMS,isomer #2	C=CCC1=CC(O)=CC=C1OCC(CN(C(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2805.0	Semi standard non polar	33892256
4-Hydroxy-alprenolol,2TBDMS,isomer #3	C=CCC1=CC(O[Si](C)(C)C(C)(C)C)=CC=C1OCC(O)CN(C(C)C)[Si](C)(C)C(C)(C)C	2756.1	Semi standard non polar	33892256
4-Hydroxy-alprenolol,3TBDMS,isomer #1	C=CCC1=CC(O[Si](C)(C)C(C)(C)C)=CC=C1OCC(CN(C(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2980.1	Semi standard non polar	33892256
4-Hydroxy-alprenolol,3TBDMS,isomer #1	C=CCC1=CC(O[Si](C)(C)C(C)(C)C)=CC=C1OCC(CN(C(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2892.5	Standard non polar	33892256
4-Hydroxy-alprenolol,3TBDMS,isomer #1	C=CCC1=CC(O[Si](C)(C)C(C)(C)C)=CC=C1OCC(CN(C(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2723.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxy-alprenolol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0uk9-9620000000-d14d23d1e5df360da99e	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxy-alprenolol GC-MS (2 TMS) - 70eV, Positive	splash10-00dl-8229000000-acf1b0eaeec0730d0ae1	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxy-alprenolol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxy-alprenolol 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-Hydroxy-alprenolol 10V, Positive-QTOF	splash10-014i-1290000000-5fa6264542e41cb1f613	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-alprenolol 20V, Positive-QTOF	splash10-00di-9570000000-faf719c7ad297ea8732b	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-alprenolol 40V, Positive-QTOF	splash10-05gl-9200000000-f95fffa79d89f3644dcf	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-alprenolol 10V, Negative-QTOF	splash10-03dj-1590000000-48c9d70677c024e397c0	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-alprenolol 20V, Negative-QTOF	splash10-0002-0900000000-a8c2fec677337aab90ee	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-alprenolol 40V, Negative-QTOF	splash10-0a4j-2900000000-0474bc91645edb1610ba	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-alprenolol 10V, Negative-QTOF	splash10-03di-0920000000-70eee85ef7926c991fce	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-alprenolol 20V, Negative-QTOF	splash10-0002-1900000000-056bea127ffd10c18fd7	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-alprenolol 40V, Negative-QTOF	splash10-0a4j-9500000000-47c5e74c113807ed37a5	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-alprenolol 10V, Positive-QTOF	splash10-014i-0090000000-4e146c2147293d54f35a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-alprenolol 20V, Positive-QTOF	splash10-00xs-9640000000-9892af4087b99ffabe59	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-alprenolol 40V, Positive-QTOF	splash10-05fr-9300000000-131bf0104097437c3a7e	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

171322

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-Hydroxy-alprenolol (HMDB0061122)

MOL for HMDB0061122 (4-Hydroxy-alprenolol)

3D MOL for HMDB0061122 (4-Hydroxy-alprenolol)

3D SDF for HMDB0061122 (4-Hydroxy-alprenolol)

3D-SDF for HMDB0061122 (4-Hydroxy-alprenolol)

PDB for HMDB0061122 (4-Hydroxy-alprenolol)

3D PDB for HMDB0061122 (4-Hydroxy-alprenolol)

SMILES for HMDB0061122 (4-Hydroxy-alprenolol)

INCHI for HMDB0061122 (4-Hydroxy-alprenolol)

Structure for HMDB0061122 (4-Hydroxy-alprenolol)

3D Structure for HMDB0061122 (4-Hydroxy-alprenolol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra