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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 23:19:35 UTC

Update Date

2021-09-26 22:55:17 UTC

HMDB ID

HMDB0246297

Secondary Accession Numbers

None

Metabolite Identification

Common Name

4-(8-Amino-1,2,3,4-tetrahydro-2-methyl-4-isoquinolinyl)phenol

Description

4-(8-Amino-1,2,3,4-tetrahydro-2-methyl-4-isoquinolinyl)phenol, also known as nomifensine M1 or 4'-hydroxynomifensine, belongs to the class of organic compounds known as 4-phenyltetrahydroisoquinolines. 4-phenyltetrahydroisoquinolines are compounds containing a phenyl group attached to the C4-atom of a tetrahydroisoquinoline moiety. Based on a literature review very few articles have been published on 4-(8-Amino-1,2,3,4-tetrahydro-2-methyl-4-isoquinolinyl)phenol. This compound has been identified in human blood as reported by (PMID: 31557052 ). 4-(8-amino-1,2,3,4-tetrahydro-2-methyl-4-isoquinolinyl)phenol is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 4-(8-Amino-1,2,3,4-tetrahydro-2-methyl-4-isoquinolinyl)phenol is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0246297
     RDKit          3D
4-(8-Amino-1,2,3,4-tetrahydro-2-methyl-4-isoquinolinyl)phenol
 37 39  0  0  0  0  0  0  0  0999 V2000
    2.4338    2.5571   -1.2482 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5043    1.4949   -1.1085 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0175    0.2087   -0.8774 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5747   -0.2867    0.4637 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4085   -1.1699    1.1133 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6281   -1.5784    0.5180 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0498   -1.6667    2.3678 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8596   -1.2565    2.9284 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0359   -0.3641    2.2520 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3740    0.1357    1.0145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4914    1.0735    0.3018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6987    0.3328   -0.1945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7242   -0.3075   -1.4162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8653   -0.9858   -1.8444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0041   -1.0428   -1.0696 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1258   -1.7254   -1.5213 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9725   -0.3998    0.1526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8422    0.2707    0.5741 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1838    1.8109   -0.8051 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6579    3.1157   -0.3166 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1116    3.2947   -2.0114 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3943    2.1223   -1.6420 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1248    0.2364   -0.9326 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6603   -0.5463   -1.6184 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5483   -1.5310    0.9927 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6155   -1.9529   -0.4599 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7112   -2.3588    2.8678 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5715   -1.6388    3.9066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8845   -0.0897    2.7607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8782    1.8085    1.0686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8584   -0.2835   -2.0404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8724   -1.4918   -2.8198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2325   -2.7090   -1.3027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8659   -0.4492    0.7511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8268    0.7709    1.5321 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1238    2.9174   -0.6018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4463    1.6842   -1.7351 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  2  0
  5  6  1  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 11 19  1  0
 19  2  1  0
 10  4  1  0
 18 12  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  3 24  1  0
  6 25  1  0
  6 26  1  0
  7 27  1  0
  8 28  1  0
  9 29  1  0
 11 30  1  0
 13 31  1  0
 14 32  1  0
 16 33  1  0
 17 34  1  0
 18 35  1  0
 19 36  1  0
 19 37  1  0
M  END

  Mrv1652309112101192D          

 19 21  0  0  0  0            999 V2000
   -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 N   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   -1.6500    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
    0.0000   -0.0000    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
    2.1434   -0.4125    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
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 N   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   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  2  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  5 11  1  0  0  0  0
  8 12  1  0  0  0  0
  4 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 13 18  1  0  0  0  0
 16 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0246297

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1CC(C2=CC=C(O)C=C2)C2=C(C1)C(N)=CC=C2

> <INCHI_IDENTIFIER>
InChI=1S/C16H18N2O/c1-18-9-14(11-5-7-12(19)8-6-11)13-3-2-4-16(17)15(13)10-18/h2-8,14,19H,9-10,17H2,1H3

> <INCHI_KEY>
IDYRXWOMWZHWEO-UHFFFAOYSA-N

> <FORMULA>
C16H18N2O

> <MOLECULAR_WEIGHT>
254.333

> <EXACT_MASS>
254.141913208

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
28.560671767382594

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-(8-amino-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)phenol

> <ALOGPS_LOGP>
2.08

> <JCHEM_LOGP>
2.118712158092736

> <ALOGPS_LOGS>
-2.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.06596234620962

> <JCHEM_PKA_STRONGEST_BASIC>
8.628822030899387

> <JCHEM_POLAR_SURFACE_AREA>
49.489999999999995

> <JCHEM_REFRACTIVITY>
79.15820000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.73e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-(8-amino-2-methyl-3,4-dihydro-1H-isoquinolin-4-yl)phenol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0246297
     RDKit          3D
4-(8-Amino-1,2,3,4-tetrahydro-2-methyl-4-isoquinolinyl)phenol
 37 39  0  0  0  0  0  0  0  0999 V2000
    2.4338    2.5571   -1.2482 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5043    1.4949   -1.1085 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0175    0.2087   -0.8774 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5747   -0.2867    0.4637 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4085   -1.1699    1.1133 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6281   -1.5784    0.5180 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0498   -1.6667    2.3678 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8596   -1.2565    2.9284 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0359   -0.3641    2.2520 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3740    0.1357    1.0145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4914    1.0735    0.3018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6987    0.3328   -0.1945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7242   -0.3075   -1.4162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8653   -0.9858   -1.8444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0041   -1.0428   -1.0696 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1258   -1.7254   -1.5213 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9725   -0.3998    0.1526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8422    0.2707    0.5741 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1838    1.8109   -0.8051 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6579    3.1157   -0.3166 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1116    3.2947   -2.0114 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3943    2.1223   -1.6420 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1248    0.2364   -0.9326 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6603   -0.5463   -1.6184 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5483   -1.5310    0.9927 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6155   -1.9529   -0.4599 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7112   -2.3588    2.8678 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5715   -1.6388    3.9066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8845   -0.0897    2.7607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8782    1.8085    1.0686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8584   -0.2835   -2.0404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8724   -1.4918   -2.8198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2325   -2.7090   -1.3027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8659   -0.4492    0.7511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8268    0.7709    1.5321 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1238    2.9174   -0.6018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4463    1.6842   -1.7351 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  2  0
  5  6  1  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 11 19  1  0
 19  2  1  0
 10  4  1  0
 18 12  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  3 24  1  0
  6 25  1  0
  6 26  1  0
  7 27  1  0
  8 28  1  0
  9 29  1  0
 11 30  1  0
 13 31  1  0
 14 32  1  0
 16 33  1  0
 17 34  1  0
 18 35  1  0
 19 36  1  0
 19 37  1  0
M  END

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0      -1.334  -0.770   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -3.080   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       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -0.770   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       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       2.667   1.540   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       0.000  -9.240   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   13                                                  
CONECT    5    4    6   11                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6    2                                                       
CONECT    8    6    9   12                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    5                                                       
CONECT   12    8                                                            
CONECT   13    4   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   17   13                                                       
CONECT   19   16                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

COMPND    HMDB0246297
HETATM    1  C1  UNL     1       2.434   2.557  -1.248  1.00  0.00           C  
HETATM    2  N1  UNL     1       1.504   1.495  -1.109  1.00  0.00           N  
HETATM    3  C2  UNL     1       2.017   0.209  -0.877  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.575  -0.287   0.464  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.409  -1.170   1.113  1.00  0.00           C  
HETATM    6  N2  UNL     1       3.628  -1.578   0.518  1.00  0.00           N  
HETATM    7  C5  UNL     1       2.050  -1.667   2.368  1.00  0.00           C  
HETATM    8  C6  UNL     1       0.860  -1.257   2.928  1.00  0.00           C  
HETATM    9  C7  UNL     1       0.036  -0.364   2.252  1.00  0.00           C  
HETATM   10  C8  UNL     1       0.374   0.136   1.015  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.491   1.074   0.302  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.699   0.333  -0.194  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.724  -0.307  -1.416  1.00  0.00           C  
HETATM   14  C12 UNL     1      -2.865  -0.986  -1.844  1.00  0.00           C  
HETATM   15  C13 UNL     1      -4.004  -1.043  -1.070  1.00  0.00           C  
HETATM   16  O1  UNL     1      -5.126  -1.725  -1.521  1.00  0.00           O  
HETATM   17  C14 UNL     1      -3.973  -0.400   0.153  1.00  0.00           C  
HETATM   18  C15 UNL     1      -2.842   0.271   0.574  1.00  0.00           C  
HETATM   19  C16 UNL     1       0.184   1.811  -0.805  1.00  0.00           C  
HETATM   20  H1  UNL     1       2.658   3.116  -0.317  1.00  0.00           H  
HETATM   21  H2  UNL     1       2.112   3.295  -2.011  1.00  0.00           H  
HETATM   22  H3  UNL     1       3.394   2.122  -1.642  1.00  0.00           H  
HETATM   23  H4  UNL     1       3.125   0.236  -0.933  1.00  0.00           H  
HETATM   24  H5  UNL     1       1.660  -0.546  -1.618  1.00  0.00           H  
HETATM   25  H6  UNL     1       4.548  -1.531   0.993  1.00  0.00           H  
HETATM   26  H7  UNL     1       3.616  -1.953  -0.460  1.00  0.00           H  
HETATM   27  H8  UNL     1       2.711  -2.359   2.868  1.00  0.00           H  
HETATM   28  H9  UNL     1       0.571  -1.639   3.907  1.00  0.00           H  
HETATM   29  H10 UNL     1      -0.884  -0.090   2.761  1.00  0.00           H  
HETATM   30  H11 UNL     1      -0.878   1.808   1.069  1.00  0.00           H  
HETATM   31  H12 UNL     1      -0.858  -0.283  -2.040  1.00  0.00           H  
HETATM   32  H13 UNL     1      -2.872  -1.492  -2.820  1.00  0.00           H  
HETATM   33  H14 UNL     1      -5.232  -2.709  -1.303  1.00  0.00           H  
HETATM   34  H15 UNL     1      -4.866  -0.449   0.751  1.00  0.00           H  
HETATM   35  H16 UNL     1      -2.827   0.771   1.532  1.00  0.00           H  
HETATM   36  H17 UNL     1       0.124   2.917  -0.602  1.00  0.00           H  
HETATM   37  H18 UNL     1      -0.446   1.684  -1.735  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3   19
CONECT    3    4   23   24
CONECT    4    5    5   10
CONECT    5    6    7
CONECT    6   25   26
CONECT    7    8    8   27
CONECT    8    9   28
CONECT    9   10   10   29
CONECT   10   11
CONECT   11   12   19   30
CONECT   12   13   13   18
CONECT   13   14   31
CONECT   14   15   15   32
CONECT   15   16   17
CONECT   16   33
CONECT   17   18   18   34
CONECT   18   35
CONECT   19   36   37
END

HMDB0246297
     RDKit          3D
4-(8-Amino-1,2,3,4-tetrahydro-2-methyl-4-isoquinolinyl)phenol
 37 39  0  0  0  0  0  0  0  0999 V2000
    2.4338    2.5571   -1.2482 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5043    1.4949   -1.1085 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0175    0.2087   -0.8774 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5747   -0.2867    0.4637 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4085   -1.1699    1.1133 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6281   -1.5784    0.5180 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0498   -1.6667    2.3678 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8596   -1.2565    2.9284 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0359   -0.3641    2.2520 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3740    0.1357    1.0145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4914    1.0735    0.3018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6987    0.3328   -0.1945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7242   -0.3075   -1.4162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8653   -0.9858   -1.8444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0041   -1.0428   -1.0696 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1258   -1.7254   -1.5213 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9725   -0.3998    0.1526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8422    0.2707    0.5741 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1838    1.8109   -0.8051 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6579    3.1157   -0.3166 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1116    3.2947   -2.0114 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3943    2.1223   -1.6420 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1248    0.2364   -0.9326 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6603   -0.5463   -1.6184 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5483   -1.5310    0.9927 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6155   -1.9529   -0.4599 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7112   -2.3588    2.8678 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5715   -1.6388    3.9066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8845   -0.0897    2.7607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8782    1.8085    1.0686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8584   -0.2835   -2.0404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8724   -1.4918   -2.8198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2325   -2.7090   -1.3027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8659   -0.4492    0.7511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8268    0.7709    1.5321 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1238    2.9174   -0.6018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4463    1.6842   -1.7351 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  2  0
  5  6  1  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 11 19  1  0
 19  2  1  0
 10  4  1  0
 18 12  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  3 24  1  0
  6 25  1  0
  6 26  1  0
  7 27  1  0
  8 28  1  0
  9 29  1  0
 11 30  1  0
 13 31  1  0
 14 32  1  0
 16 33  1  0
 17 34  1  0
 18 35  1  0
 19 36  1  0
 19 37  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4'-Hydroxynomifensine	HMDB
Nomifensine m1	HMDB

Chemical Formula

C₁₆H₁₈N₂O

Average Molecular Weight

254.333

Monoisotopic Molecular Weight

254.141913208

IUPAC Name

4-(8-amino-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)phenol

Traditional Name

4-(8-amino-2-methyl-3,4-dihydro-1H-isoquinolin-4-yl)phenol

CAS Registry Number

Not Available

SMILES

CN1CC(C2=CC=C(O)C=C2)C2=C(C1)C(N)=CC=C2

InChI Identifier

InChI=1S/C16H18N2O/c1-18-9-14(11-5-7-12(19)8-6-11)13-3-2-4-16(17)15(13)10-18/h2-8,14,19H,9-10,17H2,1H3

InChI Key

IDYRXWOMWZHWEO-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 4-phenyltetrahydroisoquinolines. 4-Phenyltetrahydroisoquinolines are compounds containing a phenyl group attached to the C4-atom of a tetrahydroisoquinoline moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Tetrahydroisoquinolines

Sub Class

4-phenyltetrahydroisoquinolines

Direct Parent

4-phenyltetrahydroisoquinolines

Alternative Parents

Substituents

4-phenyltetrahydroisoquinoline
1-hydroxy-2-unsubstituted benzenoid
Phenol
Aralkylamine
Monocyclic benzene moiety
Benzenoid
Tertiary amine
Tertiary aliphatic amine
Azacycle
Organic nitrogen compound
Hydrocarbon derivative
Primary amine
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	2.08	ALOGPS
logP	2.12	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	10.07	ChemAxon
pKa (Strongest Basic)	8.63	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	49.49 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	79.16 m³·mol⁻¹	ChemAxon
Polarizability	28.56 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	162.045	30932474
DeepCCS	[M-H]-	159.687	30932474
DeepCCS	[M-2H]-	192.573	30932474
DeepCCS	[M+Na]+	168.138	30932474
AllCCS	[M+H]+	159.5	32859911
AllCCS	[M+H-H2O]+	155.6	32859911
AllCCS	[M+NH4]+	163.1	32859911
AllCCS	[M+Na]+	164.2	32859911
AllCCS	[M-H]-	165.9	32859911
AllCCS	[M+Na-2H]-	165.6	32859911
AllCCS	[M+HCOO]-	165.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-(8-Amino-1,2,3,4-tetrahydro-2-methyl-4-isoquinolinyl)phenol	CN1CC(C2=CC=C(O)C=C2)C2=C(C1)C(N)=CC=C2	3792.1	Standard polar	33892256
4-(8-Amino-1,2,3,4-tetrahydro-2-methyl-4-isoquinolinyl)phenol	CN1CC(C2=CC=C(O)C=C2)C2=C(C1)C(N)=CC=C2	2492.8	Standard non polar	33892256
4-(8-Amino-1,2,3,4-tetrahydro-2-methyl-4-isoquinolinyl)phenol	CN1CC(C2=CC=C(O)C=C2)C2=C(C1)C(N)=CC=C2	2486.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-(8-Amino-1,2,3,4-tetrahydro-2-methyl-4-isoquinolinyl)phenol,2TMS,isomer #1	CN1CC2=C(N[Si](C)(C)C)C=CC=C2C(C2=CC=C(O[Si](C)(C)C)C=C2)C1	2483.6	Semi standard non polar	33892256
4-(8-Amino-1,2,3,4-tetrahydro-2-methyl-4-isoquinolinyl)phenol,2TMS,isomer #1	CN1CC2=C(N[Si](C)(C)C)C=CC=C2C(C2=CC=C(O[Si](C)(C)C)C=C2)C1	2608.1	Standard non polar	33892256
4-(8-Amino-1,2,3,4-tetrahydro-2-methyl-4-isoquinolinyl)phenol,2TMS,isomer #1	CN1CC2=C(N[Si](C)(C)C)C=CC=C2C(C2=CC=C(O[Si](C)(C)C)C=C2)C1	2879.3	Standard polar	33892256
4-(8-Amino-1,2,3,4-tetrahydro-2-methyl-4-isoquinolinyl)phenol,2TMS,isomer #2	CN1CC2=C(C=CC=C2N([Si](C)(C)C)[Si](C)(C)C)C(C2=CC=C(O)C=C2)C1	2570.3	Semi standard non polar	33892256
4-(8-Amino-1,2,3,4-tetrahydro-2-methyl-4-isoquinolinyl)phenol,2TMS,isomer #2	CN1CC2=C(C=CC=C2N([Si](C)(C)C)[Si](C)(C)C)C(C2=CC=C(O)C=C2)C1	2759.6	Standard non polar	33892256
4-(8-Amino-1,2,3,4-tetrahydro-2-methyl-4-isoquinolinyl)phenol,2TMS,isomer #2	CN1CC2=C(C=CC=C2N([Si](C)(C)C)[Si](C)(C)C)C(C2=CC=C(O)C=C2)C1	2939.0	Standard polar	33892256
4-(8-Amino-1,2,3,4-tetrahydro-2-methyl-4-isoquinolinyl)phenol,3TMS,isomer #1	CN1CC2=C(C=CC=C2N([Si](C)(C)C)[Si](C)(C)C)C(C2=CC=C(O[Si](C)(C)C)C=C2)C1	2497.8	Semi standard non polar	33892256
4-(8-Amino-1,2,3,4-tetrahydro-2-methyl-4-isoquinolinyl)phenol,3TMS,isomer #1	CN1CC2=C(C=CC=C2N([Si](C)(C)C)[Si](C)(C)C)C(C2=CC=C(O[Si](C)(C)C)C=C2)C1	2714.2	Standard non polar	33892256
4-(8-Amino-1,2,3,4-tetrahydro-2-methyl-4-isoquinolinyl)phenol,3TMS,isomer #1	CN1CC2=C(C=CC=C2N([Si](C)(C)C)[Si](C)(C)C)C(C2=CC=C(O[Si](C)(C)C)C=C2)C1	2710.6	Standard polar	33892256
4-(8-Amino-1,2,3,4-tetrahydro-2-methyl-4-isoquinolinyl)phenol,2TBDMS,isomer #1	CN1CC2=C(N[Si](C)(C)C(C)(C)C)C=CC=C2C(C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)C1	2926.0	Semi standard non polar	33892256
4-(8-Amino-1,2,3,4-tetrahydro-2-methyl-4-isoquinolinyl)phenol,2TBDMS,isomer #1	CN1CC2=C(N[Si](C)(C)C(C)(C)C)C=CC=C2C(C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)C1	3134.1	Standard non polar	33892256
4-(8-Amino-1,2,3,4-tetrahydro-2-methyl-4-isoquinolinyl)phenol,2TBDMS,isomer #1	CN1CC2=C(N[Si](C)(C)C(C)(C)C)C=CC=C2C(C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)C1	3110.1	Standard polar	33892256
4-(8-Amino-1,2,3,4-tetrahydro-2-methyl-4-isoquinolinyl)phenol,2TBDMS,isomer #2	CN1CC2=C(C=CC=C2N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(C2=CC=C(O)C=C2)C1	2987.4	Semi standard non polar	33892256
4-(8-Amino-1,2,3,4-tetrahydro-2-methyl-4-isoquinolinyl)phenol,2TBDMS,isomer #2	CN1CC2=C(C=CC=C2N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(C2=CC=C(O)C=C2)C1	3265.9	Standard non polar	33892256
4-(8-Amino-1,2,3,4-tetrahydro-2-methyl-4-isoquinolinyl)phenol,2TBDMS,isomer #2	CN1CC2=C(C=CC=C2N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(C2=CC=C(O)C=C2)C1	3107.5	Standard polar	33892256
4-(8-Amino-1,2,3,4-tetrahydro-2-methyl-4-isoquinolinyl)phenol,3TBDMS,isomer #1	CN1CC2=C(C=CC=C2N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)C1	3106.2	Semi standard non polar	33892256
4-(8-Amino-1,2,3,4-tetrahydro-2-methyl-4-isoquinolinyl)phenol,3TBDMS,isomer #1	CN1CC2=C(C=CC=C2N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)C1	3384.8	Standard non polar	33892256
4-(8-Amino-1,2,3,4-tetrahydro-2-methyl-4-isoquinolinyl)phenol,3TBDMS,isomer #1	CN1CC2=C(C=CC=C2N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)C1	2995.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4-(8-Amino-1,2,3,4-tetrahydro-2-methyl-4-isoquinolinyl)phenol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0iki-0590000000-51521f41b0a9c9862745	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-(8-Amino-1,2,3,4-tetrahydro-2-methyl-4-isoquinolinyl)phenol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-(8-Amino-1,2,3,4-tetrahydro-2-methyl-4-isoquinolinyl)phenol GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-(8-Amino-1,2,3,4-tetrahydro-2-methyl-4-isoquinolinyl)phenol GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-(8-Amino-1,2,3,4-tetrahydro-2-methyl-4-isoquinolinyl)phenol GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-(8-Amino-1,2,3,4-tetrahydro-2-methyl-4-isoquinolinyl)phenol GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(8-Amino-1,2,3,4-tetrahydro-2-methyl-4-isoquinolinyl)phenol 10V, Positive-QTOF	splash10-0a4i-0090000000-64482d76eb2af9290a78	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(8-Amino-1,2,3,4-tetrahydro-2-methyl-4-isoquinolinyl)phenol 20V, Positive-QTOF	splash10-0a4i-0490000000-fcdcb70f444eeda6afa3	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(8-Amino-1,2,3,4-tetrahydro-2-methyl-4-isoquinolinyl)phenol 40V, Positive-QTOF	splash10-0a4i-1910000000-638f6033a9e0f83d4de1	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(8-Amino-1,2,3,4-tetrahydro-2-methyl-4-isoquinolinyl)phenol 10V, Negative-QTOF	splash10-0udi-0090000000-6955ca0e1ca8673198f8	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(8-Amino-1,2,3,4-tetrahydro-2-methyl-4-isoquinolinyl)phenol 20V, Negative-QTOF	splash10-0udi-0190000000-977dcbde6ac28fa8ec0e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(8-Amino-1,2,3,4-tetrahydro-2-methyl-4-isoquinolinyl)phenol 40V, Negative-QTOF	splash10-1000-1970000000-464ead737845c000d789	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

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

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

142909

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

162784

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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

Showing metabocard for 4-(8-Amino-1,2,3,4-tetrahydro-2-methyl-4-isoquinolinyl)phenol (HMDB0246297)

MOL for HMDB0246297 (4-(8-Amino-1,2,3,4-tetrahydro-2-methyl-4-isoquinolinyl)phenol)

3D MOL for HMDB0246297 (4-(8-Amino-1,2,3,4-tetrahydro-2-methyl-4-isoquinolinyl)phenol)

3D SDF for HMDB0246297 (4-(8-Amino-1,2,3,4-tetrahydro-2-methyl-4-isoquinolinyl)phenol)

3D-SDF for HMDB0246297 (4-(8-Amino-1,2,3,4-tetrahydro-2-methyl-4-isoquinolinyl)phenol)

PDB for HMDB0246297 (4-(8-Amino-1,2,3,4-tetrahydro-2-methyl-4-isoquinolinyl)phenol)

3D PDB for HMDB0246297 (4-(8-Amino-1,2,3,4-tetrahydro-2-methyl-4-isoquinolinyl)phenol)

SMILES for HMDB0246297 (4-(8-Amino-1,2,3,4-tetrahydro-2-methyl-4-isoquinolinyl)phenol)

INCHI for HMDB0246297 (4-(8-Amino-1,2,3,4-tetrahydro-2-methyl-4-isoquinolinyl)phenol)

Structure for HMDB0246297 (4-(8-Amino-1,2,3,4-tetrahydro-2-methyl-4-isoquinolinyl)phenol)

3D Structure for HMDB0246297 (4-(8-Amino-1,2,3,4-tetrahydro-2-methyl-4-isoquinolinyl)phenol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra