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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:00:50 UTC

Update Date

2021-09-14 15:44:19 UTC

HMDB ID

HMDB0014017

Secondary Accession Numbers

HMDB14017

Metabolite Identification

Common Name

4-Hydroxyketamine

Description

4-Hydroxyketamine is only found in individuals that have used or taken Ketamine. 4-Hydroxyketamine is a metabolite of Ketamine. 4-hydroxyketamine belongs to the family of Phenylmethylamines. These are compounds containing a phenylmethtylamine moiety, which consists of a phenyl group substituted by an methanamine.

Structure

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

HMDB0014017
     RDKit          3D
4-Hydroxyketamine
 33 34  0  0  0  0  0  0  0  0999 V2000
   -0.9180    2.5204    1.1347 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1718    1.8504    0.5265 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0285    0.4893    0.1426 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3039   -0.0004   -0.2995 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5867   -0.4879   -1.5329 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8510   -0.9415   -1.8934 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8587   -0.8926   -0.9564 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5885   -0.4010    0.2958 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3234    0.0459    0.6353 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1302    0.6725    2.2619 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.1128    0.3333   -0.9043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4428   -0.0270   -0.2057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5018    0.2266   -1.0645 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3343   -1.5324    0.0943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9950   -1.7268    0.8198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4815   -0.3721    1.2625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4897   -0.1304    2.4279 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7776    2.7132    0.4696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5369    3.5515    1.4035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1815    2.0637    2.0975 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7425    2.3803   -0.1320 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8207   -0.5312   -2.2899 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0141   -1.3176   -2.8864 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8707   -1.2357   -1.1837 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3910   -0.3593    1.0474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2034    1.2671   -1.4763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9674   -0.5240   -1.5868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5382    0.4637    0.7625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3336    0.3293   -0.5221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1783   -1.8848    0.7165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2890   -2.0162   -0.9040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0799   -2.4184    1.6570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2630   -2.1076    0.0824 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
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  3 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16  3  1  0
  9  4  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  5 22  1  0
  6 23  1  0
  7 24  1  0
  8 25  1  0
 11 26  1  0
 11 27  1  0
 12 28  1  0
 13 29  1  0
 14 30  1  0
 14 31  1  0
 15 32  1  0
 15 33  1  0
M  END


  Mrv0541 06191310402D          

 17 18  0  0  0  0            999 V2000
    9.9629   -4.4984    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.9835   -3.9340    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9999   -3.2196    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.4124   -3.9340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1269   -4.3465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1269   -5.1715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4124   -5.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6979   -4.3465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6979   -5.1715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0444   -3.4037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8197   -3.6859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9011   -2.5913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1750   -3.2196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4515   -3.1556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5331   -2.0610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3084   -2.3432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8413   -5.5840    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1 11  1  0  0  0  0
  2  8  2  0  0  0  0
  3  4  1  0  0  0  0
  3 13  1  0  0  0  0
  4  5  1  0  0  0  0
  4  8  1  0  0  0  0
  4 10  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  9  1  0  0  0  0
  8  9  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
 11 14  2  0  0  0  0
 12 15  1  0  0  0  0
 14 16  1  0  0  0  0
 15 16  2  0  0  0  0
  6 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014017

> <DATABASE_NAME>
hmdb

> <SMILES>
CNC1(CC(O)CCC1=O)C1=CC=CC=C1Cl

> <INCHI_IDENTIFIER>
InChI=1S/C13H16ClNO2/c1-15-13(8-9(16)6-7-12(13)17)10-4-2-3-5-11(10)14/h2-5,9,15-16H,6-8H2,1H3

> <INCHI_KEY>
RHZRNGQIDYHQPV-UHFFFAOYSA-N

> <FORMULA>
C13H16ClNO2

> <MOLECULAR_WEIGHT>
253.725

> <EXACT_MASS>
253.086956468

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
25.79466599909114

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(2-chlorophenyl)-4-hydroxy-2-(methylamino)cyclohexan-1-one

> <ALOGPS_LOGP>
1.25

> <JCHEM_LOGP>
1.8877901329999998

> <ALOGPS_LOGS>
-2.35

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
16.850670831891986

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.107108221170751

> <JCHEM_PKA_STRONGEST_BASIC>
7.043074422848603

> <JCHEM_POLAR_SURFACE_AREA>
49.33

> <JCHEM_REFRACTIVITY>
67.17970000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.12e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(2-chlorophenyl)-4-hydroxy-2-(methylamino)cyclohexan-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014017
     RDKit          3D
4-Hydroxyketamine
 33 34  0  0  0  0  0  0  0  0999 V2000
   -0.9180    2.5204    1.1347 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1718    1.8504    0.5265 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0285    0.4893    0.1426 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3039   -0.0004   -0.2995 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5867   -0.4879   -1.5329 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8510   -0.9415   -1.8934 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8587   -0.8926   -0.9564 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5885   -0.4010    0.2958 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3234    0.0459    0.6353 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1302    0.6725    2.2619 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.1128    0.3333   -0.9043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4428   -0.0270   -0.2057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5018    0.2266   -1.0645 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3343   -1.5324    0.0943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9950   -1.7268    0.8198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4815   -0.3721    1.2625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4897   -0.1304    2.4279 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7776    2.7132    0.4696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5369    3.5515    1.4035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1815    2.0637    2.0975 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7425    2.3803   -0.1320 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8207   -0.5312   -2.2899 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0141   -1.3176   -2.8864 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8707   -1.2357   -1.1837 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3910   -0.3593    1.0474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2034    1.2671   -1.4763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9674   -0.5240   -1.5868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5382    0.4637    0.7625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3336    0.3293   -0.5221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1783   -1.8848    0.7165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2890   -2.0162   -0.9040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0799   -2.4184    1.6570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2630   -2.1076    0.0824 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
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  3 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16  3  1  0
  9  4  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  5 22  1  0
  6 23  1  0
  7 24  1  0
  8 25  1  0
 11 26  1  0
 11 27  1  0
 12 28  1  0
 13 29  1  0
 14 30  1  0
 14 31  1  0
 15 32  1  0
 15 33  1  0
M  END

HEADER    PROTEIN                                 19-JUN-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-13         0                                  
HETATM    1 Cl   UNK     0      18.597  -8.397   0.000  0.00  0.00          Cl+0
HETATM    2  O   UNK     0      13.036  -7.343   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0      14.933  -6.010   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      15.703  -7.343   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      17.037  -8.113   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      17.037  -9.654   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      15.703 -10.424   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      14.369  -8.113   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      14.369  -9.654   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      16.883  -6.354   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      18.330  -6.880   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      16.615  -4.837   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.393  -6.010   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      19.510  -5.890   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      17.795  -3.847   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      19.242  -4.374   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      18.371 -10.424   0.000  0.00  0.00           O+0
CONECT    1   11                                                            
CONECT    2    8                                                            
CONECT    3    4   13                                                       
CONECT    4    3    5    8   10                                             
CONECT    5    4    6                                                       
CONECT    6    5    7   17                                                  
CONECT    7    6    9                                                       
CONECT    8    2    4    9                                                  
CONECT    9    7    8                                                       
CONECT   10    4   11   12                                                  
CONECT   11    1   10   14                                                  
CONECT   12   10   15                                                       
CONECT   13    3                                                            
CONECT   14   11   16                                                       
CONECT   15   12   16                                                       
CONECT   16   14   15                                                       
CONECT   17    6                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

COMPND    HMDB0014017
HETATM    1  C1  UNL     1      -0.918   2.520   1.135  1.00  0.00           C  
HETATM    2  N1  UNL     1       0.172   1.850   0.526  1.00  0.00           N  
HETATM    3  C2  UNL     1      -0.029   0.489   0.143  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.304  -0.000  -0.300  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.587  -0.488  -1.533  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.851  -0.942  -1.893  1.00  0.00           C  
HETATM    7  C6  UNL     1       3.859  -0.893  -0.956  1.00  0.00           C  
HETATM    8  C7  UNL     1       3.588  -0.401   0.296  1.00  0.00           C  
HETATM    9  C8  UNL     1       2.323   0.046   0.635  1.00  0.00           C  
HETATM   10 CL1  UNL     1       2.130   0.672   2.262  1.00  0.00          CL  
HETATM   11  C9  UNL     1      -1.113   0.333  -0.904  1.00  0.00           C  
HETATM   12  C10 UNL     1      -2.443  -0.027  -0.206  1.00  0.00           C  
HETATM   13  O1  UNL     1      -3.502   0.227  -1.064  1.00  0.00           O  
HETATM   14  C11 UNL     1      -2.334  -1.532   0.094  1.00  0.00           C  
HETATM   15  C12 UNL     1      -0.995  -1.727   0.820  1.00  0.00           C  
HETATM   16  C13 UNL     1      -0.482  -0.372   1.262  1.00  0.00           C  
HETATM   17  O2  UNL     1      -0.490  -0.130   2.428  1.00  0.00           O  
HETATM   18  H1  UNL     1      -1.778   2.713   0.470  1.00  0.00           H  
HETATM   19  H2  UNL     1      -0.537   3.552   1.404  1.00  0.00           H  
HETATM   20  H3  UNL     1      -1.181   2.064   2.097  1.00  0.00           H  
HETATM   21  H4  UNL     1       0.742   2.380  -0.132  1.00  0.00           H  
HETATM   22  H5  UNL     1       0.821  -0.531  -2.290  1.00  0.00           H  
HETATM   23  H6  UNL     1       3.014  -1.318  -2.886  1.00  0.00           H  
HETATM   24  H7  UNL     1       4.871  -1.236  -1.184  1.00  0.00           H  
HETATM   25  H8  UNL     1       4.391  -0.359   1.047  1.00  0.00           H  
HETATM   26  H9  UNL     1      -1.203   1.267  -1.476  1.00  0.00           H  
HETATM   27  H10 UNL     1      -0.967  -0.524  -1.587  1.00  0.00           H  
HETATM   28  H11 UNL     1      -2.538   0.464   0.762  1.00  0.00           H  
HETATM   29  H12 UNL     1      -4.334   0.329  -0.522  1.00  0.00           H  
HETATM   30  H13 UNL     1      -3.178  -1.885   0.716  1.00  0.00           H  
HETATM   31  H14 UNL     1      -2.289  -2.016  -0.904  1.00  0.00           H  
HETATM   32  H15 UNL     1      -1.080  -2.418   1.657  1.00  0.00           H  
HETATM   33  H16 UNL     1      -0.263  -2.108   0.082  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3   21
CONECT    3    4   11   16
CONECT    4    5    5    9
CONECT    5    6   22
CONECT    6    7    7   23
CONECT    7    8   24
CONECT    8    9    9   25
CONECT    9   10
CONECT   11   12   26   27
CONECT   12   13   14   28
CONECT   13   29
CONECT   14   15   30   31
CONECT   15   16   32   33
CONECT   16   17   17
END

HMDB0014017
     RDKit          3D
4-Hydroxyketamine
 33 34  0  0  0  0  0  0  0  0999 V2000
   -0.9180    2.5204    1.1347 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1718    1.8504    0.5265 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0285    0.4893    0.1426 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3039   -0.0004   -0.2995 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5867   -0.4879   -1.5329 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8510   -0.9415   -1.8934 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8587   -0.8926   -0.9564 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5885   -0.4010    0.2958 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3234    0.0459    0.6353 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1302    0.6725    2.2619 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.1128    0.3333   -0.9043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4428   -0.0270   -0.2057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5018    0.2266   -1.0645 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3343   -1.5324    0.0943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9950   -1.7268    0.8198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4815   -0.3721    1.2625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4897   -0.1304    2.4279 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7776    2.7132    0.4696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5369    3.5515    1.4035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1815    2.0637    2.0975 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7425    2.3803   -0.1320 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8207   -0.5312   -2.2899 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0141   -1.3176   -2.8864 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8707   -1.2357   -1.1837 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3910   -0.3593    1.0474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2034    1.2671   -1.4763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9674   -0.5240   -1.5868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5382    0.4637    0.7625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3336    0.3293   -0.5221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1783   -1.8848    0.7165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2890   -2.0162   -0.9040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0799   -2.4184    1.6570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2630   -2.1076    0.0824 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
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  3 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16  3  1  0
  9  4  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  5 22  1  0
  6 23  1  0
  7 24  1  0
  8 25  1  0
 11 26  1  0
 11 27  1  0
 12 28  1  0
 13 29  1  0
 14 30  1  0
 14 31  1  0
 15 32  1  0
 15 33  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₃H₁₆ClNO₂

Average Molecular Weight

253.725

Monoisotopic Molecular Weight

253.086956468

IUPAC Name

2-(2-chlorophenyl)-4-hydroxy-2-(methylamino)cyclohexan-1-one

Traditional Name

2-(2-chlorophenyl)-4-hydroxy-2-(methylamino)cyclohexan-1-one

CAS Registry Number

Not Available

SMILES

CNC1(CC(O)CCC1=O)C1=CC=CC=C1Cl

InChI Identifier

InChI=1S/C13H16ClNO2/c1-15-13(8-9(16)6-7-12(13)17)10-4-2-3-5-11(10)14/h2-5,9,15-16H,6-8H2,1H3

InChI Key

RHZRNGQIDYHQPV-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as chlorobenzenes. Chlorobenzenes are compounds containing one or more chlorine atoms attached to a benzene moiety.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Halobenzenes

Direct Parent

Chlorobenzenes

Alternative Parents

Substituents

Chlorobenzene
Aralkylamine
Aryl chloride
Aryl halide
Cyclic alcohol
Cyclic ketone
Secondary alcohol
Ketone
Secondary aliphatic amine
Secondary amine
Alcohol
Organonitrogen compound
Organochloride
Organohalogen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Organic nitrogen compound
Amine
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 (PMID: 21059682)

Organ

Liver (HMDB: HMDB0014017)
Kidney (HMDB: HMDB0014017)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Extracellular (HMDB: HMDB0014017)

Source

Endogenous

Endogenous (HMDB: HMDB0014017)

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	1.12 g/L	ALOGPS
logP	1.25	ALOGPS
logP	1.89	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	15.11	ChemAxon
pKa (Strongest Basic)	7.04	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	49.33 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	67.18 m³·mol⁻¹	ChemAxon
Polarizability	25.79 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
DeepCCS	[M+H]+	155.287	30932474
DeepCCS	[M-H]-	152.929	30932474
DeepCCS	[M-2H]-	186.538	30932474
DeepCCS	[M+Na]+	161.53	30932474
AllCCS	[M+H]+	157.1	32859911
AllCCS	[M+H-H2O]+	153.3	32859911
AllCCS	[M+NH4]+	160.7	32859911
AllCCS	[M+Na]+	161.7	32859911
AllCCS	[M-H]-	158.8	32859911
AllCCS	[M+Na-2H]-	159.0	32859911
AllCCS	[M+HCOO]-	159.4	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	3.78 minutes	32390414
Predicted by Siyang on May 30, 2022	9.8799 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.5 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1077.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	242.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	127.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	175.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	86.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	295.0 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	322.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	602.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	716.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	274.5 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	904.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	184.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	249.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	618.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	330.1 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	107.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Hydroxyketamine	CNC1(CC(O)CCC1=O)C1=CC=CC=C1Cl	2843.4	Standard polar	33892256
4-Hydroxyketamine	CNC1(CC(O)CCC1=O)C1=CC=CC=C1Cl	1960.8	Standard non polar	33892256
4-Hydroxyketamine	CNC1(CC(O)CCC1=O)C1=CC=CC=C1Cl	2048.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-Hydroxyketamine,1TMS,isomer #1	CNC1(C2=CC=CC=C2Cl)CC(O[Si](C)(C)C)CCC1=O	2034.3	Semi standard non polar	33892256
4-Hydroxyketamine,1TMS,isomer #2	CNC1(C2=CC=CC=C2Cl)CC(O)CC=C1O[Si](C)(C)C	2124.3	Semi standard non polar	33892256
4-Hydroxyketamine,1TMS,isomer #3	CN(C1(C2=CC=CC=C2Cl)CC(O)CCC1=O)[Si](C)(C)C	2115.1	Semi standard non polar	33892256
4-Hydroxyketamine,2TMS,isomer #1	CNC1(C2=CC=CC=C2Cl)CC(O[Si](C)(C)C)CC=C1O[Si](C)(C)C	2086.2	Semi standard non polar	33892256
4-Hydroxyketamine,2TMS,isomer #1	CNC1(C2=CC=CC=C2Cl)CC(O[Si](C)(C)C)CC=C1O[Si](C)(C)C	2135.4	Standard non polar	33892256
4-Hydroxyketamine,2TMS,isomer #1	CNC1(C2=CC=CC=C2Cl)CC(O[Si](C)(C)C)CC=C1O[Si](C)(C)C	2536.6	Standard polar	33892256
4-Hydroxyketamine,2TMS,isomer #2	CN(C1(C2=CC=CC=C2Cl)CC(O[Si](C)(C)C)CCC1=O)[Si](C)(C)C	2130.7	Semi standard non polar	33892256
4-Hydroxyketamine,2TMS,isomer #2	CN(C1(C2=CC=CC=C2Cl)CC(O[Si](C)(C)C)CCC1=O)[Si](C)(C)C	2245.5	Standard non polar	33892256
4-Hydroxyketamine,2TMS,isomer #2	CN(C1(C2=CC=CC=C2Cl)CC(O[Si](C)(C)C)CCC1=O)[Si](C)(C)C	2531.1	Standard polar	33892256
4-Hydroxyketamine,2TMS,isomer #3	CN(C1(C2=CC=CC=C2Cl)CC(O)CC=C1O[Si](C)(C)C)[Si](C)(C)C	2201.3	Semi standard non polar	33892256
4-Hydroxyketamine,2TMS,isomer #3	CN(C1(C2=CC=CC=C2Cl)CC(O)CC=C1O[Si](C)(C)C)[Si](C)(C)C	1950.2	Standard non polar	33892256
4-Hydroxyketamine,2TMS,isomer #3	CN(C1(C2=CC=CC=C2Cl)CC(O)CC=C1O[Si](C)(C)C)[Si](C)(C)C	2697.2	Standard polar	33892256
4-Hydroxyketamine,3TMS,isomer #1	CN(C1(C2=CC=CC=C2Cl)CC(O[Si](C)(C)C)CC=C1O[Si](C)(C)C)[Si](C)(C)C	2167.8	Semi standard non polar	33892256
4-Hydroxyketamine,3TMS,isomer #1	CN(C1(C2=CC=CC=C2Cl)CC(O[Si](C)(C)C)CC=C1O[Si](C)(C)C)[Si](C)(C)C	2080.1	Standard non polar	33892256
4-Hydroxyketamine,3TMS,isomer #1	CN(C1(C2=CC=CC=C2Cl)CC(O[Si](C)(C)C)CC=C1O[Si](C)(C)C)[Si](C)(C)C	2440.4	Standard polar	33892256
4-Hydroxyketamine,1TBDMS,isomer #1	CNC1(C2=CC=CC=C2Cl)CC(O[Si](C)(C)C(C)(C)C)CCC1=O	2269.4	Semi standard non polar	33892256
4-Hydroxyketamine,1TBDMS,isomer #2	CNC1(C2=CC=CC=C2Cl)CC(O)CC=C1O[Si](C)(C)C(C)(C)C	2348.1	Semi standard non polar	33892256
4-Hydroxyketamine,1TBDMS,isomer #3	CN(C1(C2=CC=CC=C2Cl)CC(O)CCC1=O)[Si](C)(C)C(C)(C)C	2360.0	Semi standard non polar	33892256
4-Hydroxyketamine,2TBDMS,isomer #1	CNC1(C2=CC=CC=C2Cl)CC(O[Si](C)(C)C(C)(C)C)CC=C1O[Si](C)(C)C(C)(C)C	2509.7	Semi standard non polar	33892256
4-Hydroxyketamine,2TBDMS,isomer #1	CNC1(C2=CC=CC=C2Cl)CC(O[Si](C)(C)C(C)(C)C)CC=C1O[Si](C)(C)C(C)(C)C	2484.3	Standard non polar	33892256
4-Hydroxyketamine,2TBDMS,isomer #1	CNC1(C2=CC=CC=C2Cl)CC(O[Si](C)(C)C(C)(C)C)CC=C1O[Si](C)(C)C(C)(C)C	2731.4	Standard polar	33892256
4-Hydroxyketamine,2TBDMS,isomer #2	CN(C1(C2=CC=CC=C2Cl)CC(O[Si](C)(C)C(C)(C)C)CCC1=O)[Si](C)(C)C(C)(C)C	2607.6	Semi standard non polar	33892256
4-Hydroxyketamine,2TBDMS,isomer #2	CN(C1(C2=CC=CC=C2Cl)CC(O[Si](C)(C)C(C)(C)C)CCC1=O)[Si](C)(C)C(C)(C)C	2727.0	Standard non polar	33892256
4-Hydroxyketamine,2TBDMS,isomer #2	CN(C1(C2=CC=CC=C2Cl)CC(O[Si](C)(C)C(C)(C)C)CCC1=O)[Si](C)(C)C(C)(C)C	2717.7	Standard polar	33892256
4-Hydroxyketamine,2TBDMS,isomer #3	CN(C1(C2=CC=CC=C2Cl)CC(O)CC=C1O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2650.8	Semi standard non polar	33892256
4-Hydroxyketamine,2TBDMS,isomer #3	CN(C1(C2=CC=CC=C2Cl)CC(O)CC=C1O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2302.7	Standard non polar	33892256
4-Hydroxyketamine,2TBDMS,isomer #3	CN(C1(C2=CC=CC=C2Cl)CC(O)CC=C1O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2873.2	Standard polar	33892256
4-Hydroxyketamine,3TBDMS,isomer #1	CN(C1(C2=CC=CC=C2Cl)CC(O[Si](C)(C)C(C)(C)C)CC=C1O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2843.9	Semi standard non polar	33892256
4-Hydroxyketamine,3TBDMS,isomer #1	CN(C1(C2=CC=CC=C2Cl)CC(O[Si](C)(C)C(C)(C)C)CC=C1O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2589.8	Standard non polar	33892256
4-Hydroxyketamine,3TBDMS,isomer #1	CN(C1(C2=CC=CC=C2Cl)CC(O[Si](C)(C)C(C)(C)C)CC=C1O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2701.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxyketamine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udi-1900000000-005ec274d6d3e3b9f99f	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxyketamine GC-MS (1 TMS) - 70eV, Positive	splash10-0udi-2910000000-fa5cdfad2deeca45d0a3	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxyketamine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxyketamine 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-Hydroxyketamine 10V, Positive-QTOF	splash10-0f79-0190000000-f7f244f08e433fd174ab	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxyketamine 20V, Positive-QTOF	splash10-0fri-0390000000-00b802442afd8ac1ff44	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxyketamine 40V, Positive-QTOF	splash10-0ldr-3900000000-f957e97989baa88dbbd8	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxyketamine 10V, Negative-QTOF	splash10-0udi-0290000000-99295fa1b38f3e8e7e91	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxyketamine 20V, Negative-QTOF	splash10-0uxr-0790000000-707042721081f74f5e88	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxyketamine 40V, Negative-QTOF	splash10-03dl-4910000000-20a7c7bb5d8abb786c2a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxyketamine 10V, Negative-QTOF	splash10-0udi-0290000000-a1c3c4187fbb5fa5a044	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxyketamine 20V, Negative-QTOF	splash10-0m60-3960000000-3bf27cb875dd527ba9ac	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxyketamine 40V, Negative-QTOF	splash10-053u-9420000000-15b934eb1a0e3d10b0a4	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxyketamine 10V, Positive-QTOF	splash10-0uk9-0090000000-6f1e85d3f5819231b5b0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxyketamine 20V, Positive-QTOF	splash10-0zfr-0980000000-8bcdb411cf5dbb8a266a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxyketamine 40V, Positive-QTOF	splash10-0uki-1910000000-dbab2465e2fc1531d1f7	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular

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	Taking drug identified by DrugBank entry	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry	21059682	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

35032782

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

86115985

PDB ID

Not Available

ChEBI ID

169880

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-Hydroxyketamine (HMDB0014017)

MOL for HMDB0014017 (4-Hydroxyketamine)

3D MOL for HMDB0014017 (4-Hydroxyketamine)

3D SDF for HMDB0014017 (4-Hydroxyketamine)

3D-SDF for HMDB0014017 (4-Hydroxyketamine)

PDB for HMDB0014017 (4-Hydroxyketamine)

3D PDB for HMDB0014017 (4-Hydroxyketamine)

SMILES for HMDB0014017 (4-Hydroxyketamine)

INCHI for HMDB0014017 (4-Hydroxyketamine)

Structure for HMDB0014017 (4-Hydroxyketamine)

3D Structure for HMDB0014017 (4-Hydroxyketamine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra