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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 13:20:45 UTC

Update Date

2021-09-26 23:07:58 UTC

HMDB ID

HMDB0254159

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Loperamide oxide

Description

4-[4-(4-chlorophenyl)-4-hydroxy-1-oxo-1λ⁵-piperidin-1-yl]-N,N-dimethyl-2,2-diphenylbutanamide belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups. 4-[4-(4-chlorophenyl)-4-hydroxy-1-oxo-1λ⁵-piperidin-1-yl]-N,N-dimethyl-2,2-diphenylbutanamide is a drug. Based on a literature review very few articles have been published on 4-[4-(4-chlorophenyl)-4-hydroxy-1-oxo-1λ⁵-piperidin-1-yl]-N,N-dimethyl-2,2-diphenylbutanamide. This compound has been identified in human blood as reported by (PMID: 31557052 ). Loperamide oxide is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Loperamide oxide 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


  Mrv1572001281600052D          

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   -0.6322    2.7197    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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 30 34  1  0  0  0  0
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M  CHG  2   2  -1   5   1
M  END

HMDB0254159
     RDKit          3D
Loperamide oxide
 68 71  0  0  0  0  0  0  0  0999 V2000
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 32 65  1  0
 33 66  1  0
 34 67  1  0
 35 68  1  0
M  CHG  2   9   1  10  -1
M  END


  Mrv1572001281600052D          

 35 38  0  0  0  0            999 V2000
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 29 35  2  0  0  0  0
 30 34  1  0  0  0  0
 31 35  1  0  0  0  0
M  CHG  2   2  -1   5   1
M  END
> <DATABASE_ID>
HMDB0254159

> <DATABASE_NAME>
hmdb

> <SMILES>
CN(C)C(=O)C(CC[N+]1([O-])CCC(O)(CC1)C1=CC=C(Cl)C=C1)(C1=CC=CC=C1)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C29H33ClN2O3/c1-31(2)27(33)29(24-9-5-3-6-10-24,25-11-7-4-8-12-25)19-22-32(35)20-17-28(34,18-21-32)23-13-15-26(30)16-14-23/h3-16,34H,17-22H2,1-2H3

> <INCHI_KEY>
KXVSBTJVTUVNPM-UHFFFAOYSA-N

> <FORMULA>
C29H33ClN2O3

> <MOLECULAR_WEIGHT>
493.04

> <EXACT_MASS>
492.2179706

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
53.82935286311855

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-(4-chlorophenyl)-1-[3-(dimethylcarbamoyl)-3,3-diphenylpropyl]-4-hydroxypiperidin-1-ium-1-olate

> <ALOGPS_LOGP>
3.56

> <JCHEM_LOGP>
3.6468156753333334

> <ALOGPS_LOGS>
-6.35

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.661169057218636

> <JCHEM_PKA_STRONGEST_BASIC>
4.010321924246174

> <JCHEM_POLAR_SURFACE_AREA>
63.6

> <JCHEM_REFRACTIVITY>
141.36390000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.21e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-(4-chlorophenyl)-1-[3-(dimethylcarbamoyl)-3,3-diphenylpropyl]-4-hydroxypiperidin-1-ium-1-olate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0254159
     RDKit          3D
Loperamide oxide
 68 71  0  0  0  0  0  0  0  0999 V2000
   -5.1922   -0.8966   -0.6748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0609   -1.7437   -0.4539 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3566   -3.1941   -0.6092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7597   -1.4221   -0.1270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9122   -2.3663    0.0203 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1878   -0.0141    0.0839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7055   -0.1746   -0.0306 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1684    0.9952    0.1482 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5789    0.6763   -0.0714 N   0  0  0  0  0  4  0  0  0  0  0  0
    2.1627    1.8241   -0.4967 O   0  0  0  0  0  1  0  0  0  0  0  0
    2.2724    0.2798    1.1206 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1527   -0.9180    0.9695 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0290   -0.9486   -0.2275 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2176   -2.3110   -0.5789 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3824   -0.3881   -0.0439 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8117    0.2963    1.0603 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1035    0.7979    1.1702 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9670    0.5887    0.1201 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6260    1.1911    0.2029 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.5670   -0.0965   -1.0054 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2730   -0.5929   -1.1015 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2842   -0.3241   -1.4005 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7781   -0.2935   -1.1249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6923    0.4629    1.3778 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5190   -0.3602    2.1453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9824    0.0730    3.3498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6701    1.3159    3.8679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8520    2.1118    3.0927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3641    1.7064    1.8702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7599    0.6994   -1.1112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1841    1.9782   -1.1103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6750    2.5827   -2.2656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7396    1.8827   -3.4421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3164    0.5747   -3.4793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8350   -0.0068   -2.3352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0633   -1.3929   -0.1353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4914   -0.9862   -1.7476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1593    0.1068   -0.2879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3339   -3.4931   -1.6552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3539   -3.3736   -0.1630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6403   -3.7756    0.0028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4202   -0.9986    0.6969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4834   -0.6616   -1.0313 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1544    1.2479    1.2590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0919    1.8814   -0.4140 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8471    1.1214    1.6029 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5327    0.0008    1.9316 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6909   -1.0670    1.9290 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4687   -1.8143    0.8999 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9988   -2.6757   -0.0876 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1466    0.4606    1.8731 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4267    1.3370    2.0578 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3007   -0.2395   -1.8174 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9945   -1.1237   -1.9935 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5162   -0.8561   -2.3401 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6019    0.7294   -1.4728 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4199   -1.3141   -0.8700 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2911    0.0338   -2.0551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7941   -1.3725    1.7836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6369   -0.5511    3.9758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0441    1.6462    4.8410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5613    3.1147    3.4459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7011    2.4090    1.3195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1888    2.5946   -0.2526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0077    3.6320   -2.2460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1319    2.3675   -4.3553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3905    0.0689   -4.4380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5057   -1.0420   -2.3733 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 13 22  1  0
 22 23  1  0
  6 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
  6 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 33 34  1  0
 34 35  2  0
 23  9  1  0
 29 24  1  0
 35 30  1  0
 21 15  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  3 39  1  0
  3 40  1  0
  3 41  1  0
  7 42  1  0
  7 43  1  0
  8 44  1  0
  8 45  1  0
 11 46  1  0
 11 47  1  0
 12 48  1  0
 12 49  1  0
 14 50  1  0
 16 51  1  0
 17 52  1  0
 20 53  1  0
 21 54  1  0
 22 55  1  0
 22 56  1  0
 23 57  1  0
 23 58  1  0
 25 59  1  0
 26 60  1  0
 27 61  1  0
 28 62  1  0
 29 63  1  0
 31 64  1  0
 32 65  1  0
 33 66  1  0
 34 67  1  0
 35 68  1  0
M  CHG  2   9   1  10  -1
M  END

HEADER    PROTEIN                                 28-JAN-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-JAN-16         0                                  
HETATM    1 Cl   UNK     0      -5.016  -7.955   0.000  0.00  0.00          Cl+0
HETATM    2  O   UNK     0      -2.706   1.793   0.000  0.00  0.00           O-1
HETATM    3  O   UNK     0      -1.166  -3.954   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      -1.524   3.127   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0      -1.936   0.460   0.000  0.00  0.00           N+1
HETATM    6  N   UNK     0      -1.180   5.077   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      -1.936  -2.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.603  -0.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.270  -0.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.603  -1.850   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.270  -1.850   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.166   1.793   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.373   1.793   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.143   3.127   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.706  -3.954   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.913   4.461   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.477   2.357   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.190   3.897   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.246  -3.954   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.936  -5.288   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.477   0.817   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.454   4.461   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.811   3.127   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.143   5.795   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -5.016  -5.288   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -2.706  -6.621   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -4.246  -6.621   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.224   5.795   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.811   0.047   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.913   7.128   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.145   2.357   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -2.697   4.809   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -0.653   6.524   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       3.454   7.128   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       5.145   0.817   0.000  0.00  0.00           C+0
CONECT    1   27                                                            
CONECT    2    5                                                            
CONECT    3    7                                                            
CONECT    4   18                                                            
CONECT    5    2    8    9   12                                             
CONECT    6   18   32   33                                                  
CONECT    7    3   10   11   15                                             
CONECT    8    5   10                                                       
CONECT    9    5   11                                                       
CONECT   10    7    8                                                       
CONECT   11    7    9                                                       
CONECT   12    5   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   16   17   18                                             
CONECT   15    7   19   20                                                  
CONECT   16   14   22   24                                                  
CONECT   17   14   21   23                                                  
CONECT   18    4    6   14                                                  
CONECT   19   15   25                                                       
CONECT   20   15   26                                                       
CONECT   21   17   29                                                       
CONECT   22   16   28                                                       
CONECT   23   17   31                                                       
CONECT   24   16   30                                                       
CONECT   25   19   27                                                       
CONECT   26   20   27                                                       
CONECT   27    1   25   26                                                  
CONECT   28   22   34                                                       
CONECT   29   21   35                                                       
CONECT   30   24   34                                                       
CONECT   31   23   35                                                       
CONECT   32    6                                                            
CONECT   33    6                                                            
CONECT   34   28   30                                                       
CONECT   35   29   31                                                       
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

COMPND    HMDB0254159
HETATM    1  C1  UNL     1      -5.192  -0.897  -0.675  1.00  0.00           C  
HETATM    2  N1  UNL     1      -4.061  -1.744  -0.454  1.00  0.00           N  
HETATM    3  C2  UNL     1      -4.357  -3.194  -0.609  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.760  -1.422  -0.127  1.00  0.00           C  
HETATM    5  O1  UNL     1      -1.912  -2.366   0.020  1.00  0.00           O  
HETATM    6  C4  UNL     1      -2.188  -0.014   0.084  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.706  -0.175  -0.031  1.00  0.00           C  
HETATM    8  C6  UNL     1       0.168   0.995   0.148  1.00  0.00           C  
HETATM    9  N2  UNL     1       1.579   0.676  -0.071  1.00  0.00           N1+
HETATM   10  O2  UNL     1       2.163   1.824  -0.497  1.00  0.00           O1-
HETATM   11  C7  UNL     1       2.272   0.280   1.121  1.00  0.00           C  
HETATM   12  C8  UNL     1       3.153  -0.918   0.969  1.00  0.00           C  
HETATM   13  C9  UNL     1       4.029  -0.949  -0.227  1.00  0.00           C  
HETATM   14  O3  UNL     1       4.218  -2.311  -0.579  1.00  0.00           O  
HETATM   15  C10 UNL     1       5.382  -0.388  -0.044  1.00  0.00           C  
HETATM   16  C11 UNL     1       5.812   0.296   1.060  1.00  0.00           C  
HETATM   17  C12 UNL     1       7.103   0.798   1.170  1.00  0.00           C  
HETATM   18  C13 UNL     1       7.967   0.589   0.120  1.00  0.00           C  
HETATM   19 CL1  UNL     1       9.626   1.191   0.203  1.00  0.00          CL  
HETATM   20  C14 UNL     1       7.567  -0.096  -1.005  1.00  0.00           C  
HETATM   21  C15 UNL     1       6.273  -0.593  -1.102  1.00  0.00           C  
HETATM   22  C16 UNL     1       3.284  -0.324  -1.401  1.00  0.00           C  
HETATM   23  C17 UNL     1       1.778  -0.293  -1.125  1.00  0.00           C  
HETATM   24  C18 UNL     1      -2.692   0.463   1.378  1.00  0.00           C  
HETATM   25  C19 UNL     1      -3.519  -0.360   2.145  1.00  0.00           C  
HETATM   26  C20 UNL     1      -3.982   0.073   3.350  1.00  0.00           C  
HETATM   27  C21 UNL     1      -3.670   1.316   3.868  1.00  0.00           C  
HETATM   28  C22 UNL     1      -2.852   2.112   3.093  1.00  0.00           C  
HETATM   29  C23 UNL     1      -2.364   1.706   1.870  1.00  0.00           C  
HETATM   30  C24 UNL     1      -2.760   0.699  -1.111  1.00  0.00           C  
HETATM   31  C25 UNL     1      -3.184   1.978  -1.110  1.00  0.00           C  
HETATM   32  C26 UNL     1      -3.675   2.583  -2.266  1.00  0.00           C  
HETATM   33  C27 UNL     1      -3.740   1.883  -3.442  1.00  0.00           C  
HETATM   34  C28 UNL     1      -3.316   0.575  -3.479  1.00  0.00           C  
HETATM   35  C29 UNL     1      -2.835  -0.007  -2.335  1.00  0.00           C  
HETATM   36  H1  UNL     1      -6.063  -1.393  -0.135  1.00  0.00           H  
HETATM   37  H2  UNL     1      -5.491  -0.986  -1.748  1.00  0.00           H  
HETATM   38  H3  UNL     1      -5.159   0.107  -0.288  1.00  0.00           H  
HETATM   39  H4  UNL     1      -4.334  -3.493  -1.655  1.00  0.00           H  
HETATM   40  H5  UNL     1      -5.354  -3.374  -0.163  1.00  0.00           H  
HETATM   41  H6  UNL     1      -3.640  -3.776   0.003  1.00  0.00           H  
HETATM   42  H7  UNL     1      -0.420  -0.999   0.697  1.00  0.00           H  
HETATM   43  H8  UNL     1      -0.483  -0.662  -1.031  1.00  0.00           H  
HETATM   44  H9  UNL     1       0.154   1.248   1.259  1.00  0.00           H  
HETATM   45  H10 UNL     1      -0.092   1.881  -0.414  1.00  0.00           H  
HETATM   46  H11 UNL     1       2.847   1.121   1.603  1.00  0.00           H  
HETATM   47  H12 UNL     1       1.533   0.001   1.932  1.00  0.00           H  
HETATM   48  H13 UNL     1       3.691  -1.067   1.929  1.00  0.00           H  
HETATM   49  H14 UNL     1       2.469  -1.814   0.900  1.00  0.00           H  
HETATM   50  H15 UNL     1       4.999  -2.676  -0.088  1.00  0.00           H  
HETATM   51  H16 UNL     1       5.147   0.461   1.873  1.00  0.00           H  
HETATM   52  H17 UNL     1       7.427   1.337   2.058  1.00  0.00           H  
HETATM   53  H18 UNL     1       8.301  -0.240  -1.817  1.00  0.00           H  
HETATM   54  H19 UNL     1       5.995  -1.124  -1.994  1.00  0.00           H  
HETATM   55  H20 UNL     1       3.516  -0.856  -2.340  1.00  0.00           H  
HETATM   56  H21 UNL     1       3.602   0.729  -1.473  1.00  0.00           H  
HETATM   57  H22 UNL     1       1.420  -1.314  -0.870  1.00  0.00           H  
HETATM   58  H23 UNL     1       1.291   0.034  -2.055  1.00  0.00           H  
HETATM   59  H24 UNL     1      -3.794  -1.372   1.784  1.00  0.00           H  
HETATM   60  H25 UNL     1      -4.637  -0.551   3.976  1.00  0.00           H  
HETATM   61  H26 UNL     1      -4.044   1.646   4.841  1.00  0.00           H  
HETATM   62  H27 UNL     1      -2.561   3.115   3.446  1.00  0.00           H  
HETATM   63  H28 UNL     1      -1.701   2.409   1.320  1.00  0.00           H  
HETATM   64  H29 UNL     1      -3.189   2.595  -0.253  1.00  0.00           H  
HETATM   65  H30 UNL     1      -4.008   3.632  -2.246  1.00  0.00           H  
HETATM   66  H31 UNL     1      -4.132   2.368  -4.355  1.00  0.00           H  
HETATM   67  H32 UNL     1      -3.390   0.069  -4.438  1.00  0.00           H  
HETATM   68  H33 UNL     1      -2.506  -1.042  -2.373  1.00  0.00           H  
CONECT    1    2   36   37   38
CONECT    2    3    4
CONECT    3   39   40   41
CONECT    4    5    5    6
CONECT    6    7   24   30
CONECT    7    8   42   43
CONECT    8    9   44   45
CONECT    9   10   11   23
CONECT   11   12   46   47
CONECT   12   13   48   49
CONECT   13   14   15   22
CONECT   14   50
CONECT   15   16   16   21
CONECT   16   17   51
CONECT   17   18   18   52
CONECT   18   19   20
CONECT   20   21   21   53
CONECT   21   54
CONECT   22   23   55   56
CONECT   23   57   58
CONECT   24   25   25   29
CONECT   25   26   59
CONECT   26   27   27   60
CONECT   27   28   61
CONECT   28   29   29   62
CONECT   29   63
CONECT   30   31   31   35
CONECT   31   32   64
CONECT   32   33   33   65
CONECT   33   34   66
CONECT   34   35   35   67
CONECT   35   68
END

HMDB0254159
     RDKit          3D
Loperamide oxide
 68 71  0  0  0  0  0  0  0  0999 V2000
   -5.1922   -0.8966   -0.6748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0609   -1.7437   -0.4539 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3566   -3.1941   -0.6092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7597   -1.4221   -0.1270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9122   -2.3663    0.0203 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1878   -0.0141    0.0839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7055   -0.1746   -0.0306 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1684    0.9952    0.1482 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5789    0.6763   -0.0714 N   0  0  0  0  0  4  0  0  0  0  0  0
    2.1627    1.8241   -0.4967 O   0  0  0  0  0  1  0  0  0  0  0  0
    2.2724    0.2798    1.1206 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1527   -0.9180    0.9695 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0290   -0.9486   -0.2275 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2176   -2.3110   -0.5789 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3824   -0.3881   -0.0439 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8117    0.2963    1.0603 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1035    0.7979    1.1702 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9670    0.5887    0.1201 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6260    1.1911    0.2029 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.5670   -0.0965   -1.0054 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2730   -0.5929   -1.1015 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2842   -0.3241   -1.4005 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7781   -0.2935   -1.1249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6923    0.4629    1.3778 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5190   -0.3602    2.1453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9824    0.0730    3.3498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6701    1.3159    3.8679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8520    2.1118    3.0927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3641    1.7064    1.8702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7599    0.6994   -1.1112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1841    1.9782   -1.1103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6750    2.5827   -2.2656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7396    1.8827   -3.4421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3164    0.5747   -3.4793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8350   -0.0068   -2.3352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0633   -1.3929   -0.1353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4914   -0.9862   -1.7476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1593    0.1068   -0.2879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3339   -3.4931   -1.6552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3539   -3.3736   -0.1630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6403   -3.7756    0.0028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4202   -0.9986    0.6969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4834   -0.6616   -1.0313 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1544    1.2479    1.2590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0919    1.8814   -0.4140 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8471    1.1214    1.6029 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5327    0.0008    1.9316 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6909   -1.0670    1.9290 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4687   -1.8143    0.8999 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9988   -2.6757   -0.0876 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1466    0.4606    1.8731 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4267    1.3370    2.0578 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3007   -0.2395   -1.8174 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9945   -1.1237   -1.9935 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5162   -0.8561   -2.3401 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6019    0.7294   -1.4728 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4199   -1.3141   -0.8700 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2911    0.0338   -2.0551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7941   -1.3725    1.7836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6369   -0.5511    3.9758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0441    1.6462    4.8410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5613    3.1147    3.4459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7011    2.4090    1.3195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1888    2.5946   -0.2526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0077    3.6320   -2.2460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1319    2.3675   -4.3553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3905    0.0689   -4.4380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5057   -1.0420   -2.3733 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 13 22  1  0
 22 23  1  0
  6 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
  6 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 33 34  1  0
 34 35  2  0
 23  9  1  0
 29 24  1  0
 35 30  1  0
 21 15  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  3 39  1  0
  3 40  1  0
  3 41  1  0
  7 42  1  0
  7 43  1  0
  8 44  1  0
  8 45  1  0
 11 46  1  0
 11 47  1  0
 12 48  1  0
 12 49  1  0
 14 50  1  0
 16 51  1  0
 17 52  1  0
 20 53  1  0
 21 54  1  0
 22 55  1  0
 22 56  1  0
 23 57  1  0
 23 58  1  0
 25 59  1  0
 26 60  1  0
 27 61  1  0
 28 62  1  0
 29 63  1  0
 31 64  1  0
 32 65  1  0
 33 66  1  0
 34 67  1  0
 35 68  1  0
M  CHG  2   9   1  10  -1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Loperamide oxide monohydrate	MeSH
Arestal	MeSH
Loperamide oxide	MeSH
Loperamide oxide anhydrous	MeSH
4-((1R,4S)-4-(4-Chlorophenyl)-4-hydroxy-1-oxido-1-piperidinyl)-N,N-dimethyl-2,2-diphenylbutanamide	MeSH

Chemical Formula

C₂₉H₃₃ClN₂O₃

Average Molecular Weight

493.04

Monoisotopic Molecular Weight

492.2179706

IUPAC Name

4-(4-chlorophenyl)-1-[3-(dimethylcarbamoyl)-3,3-diphenylpropyl]-4-hydroxypiperidin-1-ium-1-olate

Traditional Name

4-(4-chlorophenyl)-1-[3-(dimethylcarbamoyl)-3,3-diphenylpropyl]-4-hydroxypiperidin-1-ium-1-olate

CAS Registry Number

Not Available

SMILES

CN(C)C(=O)C(CC[N+]1([O-])CCC(O)(CC1)C1=CC=C(Cl)C=C1)(C1=CC=CC=C1)C1=CC=CC=C1

InChI Identifier

InChI=1S/C29H33ClN2O3/c1-31(2)27(33)29(24-9-5-3-6-10-24,25-11-7-4-8-12-25)19-22-32(35)20-17-28(34,18-21-32)23-13-15-26(30)16-14-23/h3-16,34H,17-22H2,1-2H3

InChI Key

KXVSBTJVTUVNPM-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Diphenylmethanes

Direct Parent

Diphenylmethanes

Alternative Parents

Substituents

Diphenylmethane
Phenylpiperidine
Phenylacetamide
Halobenzene
Chlorobenzene
N-acyl-amine
Aryl chloride
Aryl halide
Piperidine
Tertiary carboxylic acid amide
Tertiary alcohol
Trialkyl amine oxide
Carboxamide group
Trisubstituted n-oxide
N-oxide
Organoheterocyclic compound
Azacycle
Carboxylic acid derivative
Alcohol
Organohalogen compound
Organochloride
Organonitrogen compound
Organooxygen compound
Organic zwitterion
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (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	3.56	ALOGPS
logP	3.65	ChemAxon
logS	-6.4	ALOGPS
pKa (Strongest Acidic)	13.66	ChemAxon
pKa (Strongest Basic)	4.01	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	141.36 m³·mol⁻¹	ChemAxon
Polarizability	53.83 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	201.507	30932474
DeepCCS	[M-H]-	199.112	30932474
DeepCCS	[M-2H]-	232.035	30932474
DeepCCS	[M+Na]+	207.42	30932474
AllCCS	[M+H]+	217.6	32859911
AllCCS	[M+H-H2O]+	215.7	32859911
AllCCS	[M+NH4]+	219.3	32859911
AllCCS	[M+Na]+	219.8	32859911
AllCCS	[M-H]-	216.6	32859911
AllCCS	[M+Na-2H]-	217.8	32859911
AllCCS	[M+HCOO]-	219.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Loperamide oxide	CN(C)C(=O)C(CC[N+]1([O-])CCC(O)(CC1)C1=CC=C(Cl)C=C1)(C1=CC=CC=C1)C1=CC=CC=C1	4728.1	Standard polar	33892256
Loperamide oxide	CN(C)C(=O)C(CC[N+]1([O-])CCC(O)(CC1)C1=CC=C(Cl)C=C1)(C1=CC=CC=C1)C1=CC=CC=C1	3024.2	Standard non polar	33892256
Loperamide oxide	CN(C)C(=O)C(CC[N+]1([O-])CCC(O)(CC1)C1=CC=C(Cl)C=C1)(C1=CC=CC=C1)C1=CC=CC=C1	3865.2	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Loperamide oxide GC-MS (Non-derivatized) - 70eV, Positive	splash10-01b9-5942500000-f6f47eb36fc0b4cab6d5	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Loperamide oxide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Loperamide oxide GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Loperamide oxide GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-04	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

DBSALT001714

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

64511

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71421

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 Loperamide oxide (HMDB0254159)

MOL for HMDB0254159 (Loperamide oxide)

3D MOL for HMDB0254159 (Loperamide oxide)

3D SDF for HMDB0254159 (Loperamide oxide)

3D-SDF for HMDB0254159 (Loperamide oxide)

PDB for HMDB0254159 (Loperamide oxide)

3D PDB for HMDB0254159 (Loperamide oxide)

SMILES for HMDB0254159 (Loperamide oxide)

INCHI for HMDB0254159 (Loperamide oxide)

Structure for HMDB0254159 (Loperamide oxide)

3D Structure for HMDB0254159 (Loperamide oxide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra