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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-13 11:49:59 UTC

Update Date

2019-07-23 06:35:18 UTC

HMDB ID

HMDB0041958

Secondary Accession Numbers

HMDB41958

Metabolite Identification

Common Name

Normeperidine

Description

Pethidine (INN) or meperidine hydrochloride (USAN) (commonly referred to as Demerol in the US but also referred to as: isonipecaine; lidol; pethanol; piridosal; Algil; Alodan; Centralgin; Dispadol; Dolantin; Mialgin (in Indonesia); Petidin Dolargan (in Poland); Dolestine; Dolosal; Dolsin; Mefedina) is a fast-acting opioid analgesic drug. Pethidine is quickly hydrolysed in the liver to pethidinic acid and is also demethylated to norpethidine, which has half the analgesic activity of pethidine but a longer elimination half-life (8-12 hours); accumulating with regular administration, or in renal failure. Norpethidine is toxic and has convulsant and hallucinogenic effects. The toxic effects mediated by the metabolites cannot be countered with opioid receptor antagonists such as naloxone or naltrexone and are probably primarily due to norpethidine's anticholinergic activity probably due to its structural similarity to atropine though its pharmacology has not been thoroughly explored. The neurotoxicity of pethidine's metabolites is a unique feature of pethidine compared to other opioids. Pethidine's metabolites are further conjugated with glucuronic acid and excreted into the urine.

Structure

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

HMDB0041958
     RDKit          3D
Normeperidine
 36 37  0  0  0  0  0  0  0  0999 V2000
    3.8307   -0.9337   -0.9168 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2455   -1.4881    0.3613 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8323   -1.5172    0.3242 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1694   -0.3151    0.1527 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8453    0.7264    0.0401 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3058   -0.1987    0.0954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6439    1.2542   -0.0031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5369    1.7345   -0.9339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8367    3.0928   -0.9883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2417    3.9728   -0.1091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3421    3.5275    0.8374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0670    2.1767    0.8651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9508   -0.6721    1.3847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1409   -2.1673    1.2608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1242   -2.5156    0.2726 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0563   -1.6937   -0.9136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7408   -1.0038   -1.0796 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0778    0.1609   -0.8081 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8176   -1.4269   -1.0827 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2006   -1.1200   -1.8003 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5358   -0.7866    1.1774 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6702   -2.5082    0.5289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0278    1.0728   -1.6428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5435    3.4659   -1.7266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4756    5.0374   -0.1508 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1438    4.1884    1.5429 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6450    1.8163    1.6307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3884   -0.4165    2.2788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9549   -0.2124    1.4395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1615   -2.6347    1.1004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5453   -2.5073    2.2537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0882   -2.4192    0.6674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1554   -2.4071   -1.7844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9345   -1.0238   -0.9915 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0087   -1.8375   -1.2657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7604   -0.4212   -2.0164 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
  4  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
  6 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17  6  1  0
 12  7  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  8 23  1  0
  9 24  1  0
 10 25  1  0
 11 26  1  0
 12 27  1  0
 13 28  1  0
 13 29  1  0
 14 30  1  0
 14 31  1  0
 15 32  1  0
 16 33  1  0
 16 34  1  0
 17 35  1  0
 17 36  1  0
M  END


  Mrv0541 09131211502D          

 17 18  0  0  0  0            999 V2000
   -3.8735    3.6176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1320    3.2559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6490    0.0576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9345    0.4701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3635    0.4701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9345    1.2951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3635    1.2951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8245    2.5614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0862    3.2322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4372    3.2898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6989    3.9607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6490    1.7076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3330    2.0713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6490    2.5326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8744    3.9894    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7701    1.3716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0745    2.4329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  2  0  0  0  0
 10  8  1  0  0  0  0
 11  9  1  0  0  0  0
 12  6  2  0  0  0  0
 12  7  1  0  0  0  0
 14  8  1  0  0  0  0
 14  9  1  0  0  0  0
 14 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15 10  1  0  0  0  0
 15 11  1  0  0  0  0
 16 13  2  0  0  0  0
 17  2  1  0  0  0  0
 17 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0041958

> <DATABASE_NAME>
hmdb

> <SMILES>
CCOC(=O)C1(CCNCC1)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C14H19NO2/c1-2-17-13(16)14(8-10-15-11-9-14)12-6-4-3-5-7-12/h3-7,15H,2,8-11H2,1H3

> <INCHI_KEY>
QKHMFBKXTNQCTM-UHFFFAOYSA-N

> <FORMULA>
C14H19NO2

> <MOLECULAR_WEIGHT>
233.3062

> <EXACT_MASS>
233.141578857

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
26.130123392422377

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
ethyl 4-phenylpiperidine-4-carboxylate

> <ALOGPS_LOGP>
1.45

> <JCHEM_LOGP>
2.072752458666666

> <ALOGPS_LOGS>
-2.86

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.332288475477153

> <JCHEM_POLAR_SURFACE_AREA>
38.33

> <JCHEM_REFRACTIVITY>
67.18900000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.22e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
norpethidine

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0041958
     RDKit          3D
Normeperidine
 36 37  0  0  0  0  0  0  0  0999 V2000
    3.8307   -0.9337   -0.9168 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2455   -1.4881    0.3613 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8323   -1.5172    0.3242 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1694   -0.3151    0.1527 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8453    0.7264    0.0401 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3058   -0.1987    0.0954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6439    1.2542   -0.0031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5369    1.7345   -0.9339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8367    3.0928   -0.9883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2417    3.9728   -0.1091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3421    3.5275    0.8374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0670    2.1767    0.8651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9508   -0.6721    1.3847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1409   -2.1673    1.2608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1242   -2.5156    0.2726 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0563   -1.6937   -0.9136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7408   -1.0038   -1.0796 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0778    0.1609   -0.8081 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8176   -1.4269   -1.0827 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2006   -1.1200   -1.8003 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5358   -0.7866    1.1774 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6702   -2.5082    0.5289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0278    1.0728   -1.6428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5435    3.4659   -1.7266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4756    5.0374   -0.1508 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1438    4.1884    1.5429 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6450    1.8163    1.6307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3884   -0.4165    2.2788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9549   -0.2124    1.4395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1615   -2.6347    1.1004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5453   -2.5073    2.2537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0882   -2.4192    0.6674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1554   -2.4071   -1.7844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9345   -1.0238   -0.9915 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0087   -1.8375   -1.2657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7604   -0.4212   -2.0164 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
  4  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
  6 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17  6  1  0
 12  7  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  8 23  1  0
  9 24  1  0
 10 25  1  0
 11 26  1  0
 12 27  1  0
 13 28  1  0
 13 29  1  0
 14 30  1  0
 14 31  1  0
 15 32  1  0
 16 33  1  0
 16 34  1  0
 17 35  1  0
 17 36  1  0
M  END

HEADER    PROTEIN                                 13-SEP-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-SEP-12         0                                  
HETATM    1  C   UNK     0      -7.231   6.753   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.846   6.078   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.078   0.108   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.744   0.878   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.412   0.878   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.744   2.418   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.412   2.418   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.539   4.781   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.894   6.033   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.816   6.141   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.171   7.393   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.078   3.188   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.355   3.866   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.078   4.728   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0      -1.632   7.447   0.000  0.00  0.00           N+0
HETATM   16  O   UNK     0      -5.171   2.560   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -5.739   4.541   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1   17                                                       
CONECT    3    4    5                                                       
CONECT    4    3    6                                                       
CONECT    5    3    7                                                       
CONECT    6    4   12                                                       
CONECT    7    5   12                                                       
CONECT    8   10   14                                                       
CONECT    9   11   14                                                       
CONECT   10    8   15                                                       
CONECT   11    9   15                                                       
CONECT   12    6    7   14                                                  
CONECT   13   14   16   17                                                  
CONECT   14    8    9   12   13                                             
CONECT   15   10   11                                                       
CONECT   16   13                                                            
CONECT   17    2   13                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

COMPND    HMDB0041958
HETATM    1  C1  UNL     1       3.831  -0.934  -0.917  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.245  -1.488   0.361  1.00  0.00           C  
HETATM    3  O1  UNL     1       1.832  -1.517   0.324  1.00  0.00           O  
HETATM    4  C3  UNL     1       1.169  -0.315   0.153  1.00  0.00           C  
HETATM    5  O2  UNL     1       1.845   0.726   0.040  1.00  0.00           O  
HETATM    6  C4  UNL     1      -0.306  -0.199   0.095  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.644   1.254  -0.003  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.537   1.735  -0.934  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.837   3.093  -0.988  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.242   3.973  -0.109  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.342   3.527   0.837  1.00  0.00           C  
HETATM   12  C10 UNL     1      -0.067   2.177   0.865  1.00  0.00           C  
HETATM   13  C11 UNL     1      -0.951  -0.672   1.385  1.00  0.00           C  
HETATM   14  C12 UNL     1      -1.141  -2.167   1.261  1.00  0.00           C  
HETATM   15  N1  UNL     1      -2.124  -2.516   0.273  1.00  0.00           N  
HETATM   16  C13 UNL     1      -2.056  -1.694  -0.914  1.00  0.00           C  
HETATM   17  C14 UNL     1      -0.741  -1.004  -1.080  1.00  0.00           C  
HETATM   18  H1  UNL     1       4.078   0.161  -0.808  1.00  0.00           H  
HETATM   19  H2  UNL     1       4.818  -1.427  -1.083  1.00  0.00           H  
HETATM   20  H3  UNL     1       3.201  -1.120  -1.800  1.00  0.00           H  
HETATM   21  H4  UNL     1       3.536  -0.787   1.177  1.00  0.00           H  
HETATM   22  H5  UNL     1       3.670  -2.508   0.529  1.00  0.00           H  
HETATM   23  H6  UNL     1      -2.028   1.073  -1.643  1.00  0.00           H  
HETATM   24  H7  UNL     1      -2.544   3.466  -1.727  1.00  0.00           H  
HETATM   25  H8  UNL     1      -1.476   5.037  -0.151  1.00  0.00           H  
HETATM   26  H9  UNL     1       0.144   4.188   1.543  1.00  0.00           H  
HETATM   27  H10 UNL     1       0.645   1.816   1.631  1.00  0.00           H  
HETATM   28  H11 UNL     1      -0.388  -0.416   2.279  1.00  0.00           H  
HETATM   29  H12 UNL     1      -1.955  -0.212   1.440  1.00  0.00           H  
HETATM   30  H13 UNL     1      -0.162  -2.635   1.100  1.00  0.00           H  
HETATM   31  H14 UNL     1      -1.545  -2.507   2.254  1.00  0.00           H  
HETATM   32  H15 UNL     1      -3.088  -2.419   0.667  1.00  0.00           H  
HETATM   33  H16 UNL     1      -2.155  -2.407  -1.784  1.00  0.00           H  
HETATM   34  H17 UNL     1      -2.934  -1.024  -0.991  1.00  0.00           H  
HETATM   35  H18 UNL     1       0.009  -1.837  -1.266  1.00  0.00           H  
HETATM   36  H19 UNL     1      -0.760  -0.421  -2.016  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3   21   22
CONECT    3    4
CONECT    4    5    5    6
CONECT    6    7   13   17
CONECT    7    8    8   12
CONECT    8    9   23
CONECT    9   10   10   24
CONECT   10   11   25
CONECT   11   12   12   26
CONECT   12   27
CONECT   13   14   28   29
CONECT   14   15   30   31
CONECT   15   16   32
CONECT   16   17   33   34
CONECT   17   35   36
END

HMDB0041958
     RDKit          3D
Normeperidine
 36 37  0  0  0  0  0  0  0  0999 V2000
    3.8307   -0.9337   -0.9168 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2455   -1.4881    0.3613 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8323   -1.5172    0.3242 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1694   -0.3151    0.1527 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8453    0.7264    0.0401 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3058   -0.1987    0.0954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6439    1.2542   -0.0031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5369    1.7345   -0.9339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8367    3.0928   -0.9883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2417    3.9728   -0.1091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3421    3.5275    0.8374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0670    2.1767    0.8651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9508   -0.6721    1.3847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1409   -2.1673    1.2608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1242   -2.5156    0.2726 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0563   -1.6937   -0.9136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7408   -1.0038   -1.0796 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0778    0.1609   -0.8081 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8176   -1.4269   -1.0827 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2006   -1.1200   -1.8003 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5358   -0.7866    1.1774 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6702   -2.5082    0.5289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0278    1.0728   -1.6428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5435    3.4659   -1.7266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4756    5.0374   -0.1508 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1438    4.1884    1.5429 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6450    1.8163    1.6307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3884   -0.4165    2.2788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9549   -0.2124    1.4395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1615   -2.6347    1.1004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5453   -2.5073    2.2537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0882   -2.4192    0.6674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1554   -2.4071   -1.7844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9345   -1.0238   -0.9915 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0087   -1.8375   -1.2657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7604   -0.4212   -2.0164 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
  4  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
  6 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17  6  1  0
 12  7  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  8 23  1  0
  9 24  1  0
 10 25  1  0
 11 26  1  0
 12 27  1  0
 13 28  1  0
 13 29  1  0
 14 30  1  0
 14 31  1  0
 15 32  1  0
 16 33  1  0
 16 34  1  0
 17 35  1  0
 17 36  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-(Ethoxycarbonyl)-4-phenylpiperidine	HMDB
4-Carbethoxy-4-phenylpiperidine	HMDB
4-Phenyl-4-carbethoxypiperidine	HMDB
Ethyl 4-phenyl-4-piperidinecarboxylate	HMDB
Ethyl 4-phenylisonipecotate	HMDB
Ethyl 4-phenylpiperidine-4-carboxylate	HMDB
Isonipecotic acid, 4-phenyl-, ethyl ester	HMDB
Nordolsin	HMDB
Norpethidine	HMDB
Normeperidine carbonate (2:1)	HMDB
Normeperidine hydrochloride	HMDB
Normeperidine, 3H-labeled CPD	HMDB
Ethyl 4-phenylpiperidine-4-carboxylic acid	HMDB
Normeperidine	MeSH

Chemical Formula

C₁₄H₁₉NO₂

Average Molecular Weight

233.3062

Monoisotopic Molecular Weight

233.141578857

IUPAC Name

ethyl 4-phenylpiperidine-4-carboxylate

Traditional Name

norpethidine

CAS Registry Number

77-17-8

SMILES

CCOC(=O)C1(CCNCC1)C1=CC=CC=C1

InChI Identifier

InChI=1S/C14H19NO2/c1-2-17-13(16)14(8-10-15-11-9-14)12-6-4-3-5-7-12/h3-7,15H,2,8-11H2,1H3

InChI Key

QKHMFBKXTNQCTM-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylpiperidines. Phenylpiperidines are compounds containing a phenylpiperidine skeleton, which consists of a piperidine bound to a phenyl group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Piperidines

Sub Class

Phenylpiperidines

Direct Parent

Phenylpiperidines

Alternative Parents

Substituents

Phenylpiperidine
Piperidinecarboxylic acid
Aralkylamine
Monocyclic benzene moiety
Benzenoid
Amino acid or derivatives
Carboxylic acid ester
Carboxylic acid derivative
Secondary aliphatic amine
Monocarboxylic acid or derivatives
Secondary amine
Azacycle
Organonitrogen compound
Organic nitrogen compound
Organopnictogen compound
Amine
Organooxygen compound
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0041958)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.32 g/L	ALOGPS
logP	1.45	ALOGPS
logP	2.07	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Basic)	9.33	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	38.33 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	67.19 m³·mol⁻¹	ChemAxon
Polarizability	26.13 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	154.977	31661259
DarkChem	[M-H]-	154.734	31661259
DeepCCS	[M+H]+	155.804	30932474
DeepCCS	[M-H]-	153.446	30932474
DeepCCS	[M-2H]-	186.698	30932474
DeepCCS	[M+Na]+	161.897	30932474
AllCCS	[M+H]+	153.3	32859911
AllCCS	[M+H-H2O]+	149.4	32859911
AllCCS	[M+NH4]+	157.0	32859911
AllCCS	[M+Na]+	158.0	32859911
AllCCS	[M-H]-	158.7	32859911
AllCCS	[M+Na-2H]-	158.9	32859911
AllCCS	[M+HCOO]-	159.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Normeperidine	CCOC(=O)C1(CCNCC1)C1=CC=CC=C1	2334.5	Standard polar	33892256
Normeperidine	CCOC(=O)C1(CCNCC1)C1=CC=CC=C1	1757.1	Standard non polar	33892256
Normeperidine	CCOC(=O)C1(CCNCC1)C1=CC=CC=C1	1773.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Normeperidine,1TMS,isomer #1	CCOC(=O)C1(C2=CC=CC=C2)CCN([Si](C)(C)C)CC1	1892.7	Semi standard non polar	33892256
Normeperidine,1TMS,isomer #1	CCOC(=O)C1(C2=CC=CC=C2)CCN([Si](C)(C)C)CC1	1970.2	Standard non polar	33892256
Normeperidine,1TBDMS,isomer #1	CCOC(=O)C1(C2=CC=CC=C2)CCN([Si](C)(C)C(C)(C)C)CC1	2166.9	Semi standard non polar	33892256
Normeperidine,1TBDMS,isomer #1	CCOC(=O)C1(C2=CC=CC=C2)CCN([Si](C)(C)C(C)(C)C)CC1	2185.1	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Normeperidine GC-MS (Non-derivatized) - 70eV, Positive	splash10-03di-1900000000-b43cba7846535ead29d3	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Normeperidine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Normeperidine 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 - Normeperidine 10V, Positive-QTOF	splash10-001i-0390000000-a12c5e20253fed706008	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Normeperidine 20V, Positive-QTOF	splash10-0019-2950000000-a36e1982a192e3f1c1bf	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Normeperidine 40V, Positive-QTOF	splash10-06z9-9800000000-3668d1535fc2fd012219	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Normeperidine 10V, Negative-QTOF	splash10-001i-0190000000-80f29ac48e0d76a75265	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Normeperidine 20V, Negative-QTOF	splash10-001r-3790000000-ce9fd6d72143008eb0d0	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Normeperidine 40V, Negative-QTOF	splash10-01t9-9710000000-1ca41e452381ae5965df	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Normeperidine 10V, Positive-QTOF	splash10-01q9-0790000000-a2020f59c6a5cdbc4d8b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Normeperidine 20V, Positive-QTOF	splash10-03di-1920000000-5d0c5488f282a077b42b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Normeperidine 40V, Positive-QTOF	splash10-01q1-2910000000-e533559084fd0b22eba3	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Normeperidine 10V, Negative-QTOF	splash10-001i-0090000000-116620fb1c68c1372159	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Normeperidine 20V, Negative-QTOF	splash10-001r-0960000000-72346e33aa360c50adf1	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Normeperidine 40V, Negative-QTOF	splash10-0pb9-2900000000-bf3685fbe38972677d87	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

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

30039

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Pethidine

METLIN ID

Not Available

PubChem Compound

32414

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Normeperidine (HMDB0041958)

MOL for HMDB0041958 (Normeperidine)

3D MOL for HMDB0041958 (Normeperidine)

3D SDF for HMDB0041958 (Normeperidine)

3D-SDF for HMDB0041958 (Normeperidine)

PDB for HMDB0041958 (Normeperidine)

3D PDB for HMDB0041958 (Normeperidine)

SMILES for HMDB0041958 (Normeperidine)

INCHI for HMDB0041958 (Normeperidine)

Structure for HMDB0041958 (Normeperidine)

3D Structure for HMDB0041958 (Normeperidine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra