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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-07-09 16:12:21 UTC

Update Date

2019-07-23 07:15:34 UTC

HMDB ID

HMDB0061010

Secondary Accession Numbers

HMDB61010

Metabolite Identification

Common Name

Noralfentanil

Description

Noralfentanil is a metabolite of alfentanil. Alfentanil (R-39209, trade name Alfenta, Rapifen in Australia) is a potent but short-acting synthetic opioid analgesic drug, used for anaesthesia in surgery. It is an analogue of fentanyl with around 1/4 the potency of fentanyl and around 1/3 of the duration of action, but with an onset of effects 4x faster than fentanyl. It is an OP3 mu-agonist. (Wikipedia)

Structure

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

HMDB0061010
     RDKit          3D
Noralfentanil
 44 45  0  0  0  0  0  0  0  0999 V2000
   -2.9541    0.5888    3.0802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6040    0.2750    1.6526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1125    0.3810    1.5115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4541    0.7304    2.5033 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4646    0.0957    0.2908 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3313   -0.2710   -0.7867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4964   -1.5477   -1.2384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3495   -1.8754   -2.2883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0510   -0.8845   -2.8938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9212    0.4086   -2.4788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0789    0.7086   -1.4470 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9632    0.1932    0.1740 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4287    1.6293    0.5097 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8254    1.5753    0.3371 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4007    2.8177    0.6038 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4250   -0.0274   -1.2472 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9865   -1.3598   -1.5603 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8190   -1.8710   -0.5003 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9431   -2.0855    0.6339 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6374   -0.6910    1.1725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8789    0.0823    3.4155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0976    1.6812    3.2193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0719    0.3330    3.7148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9834   -0.7178    1.3482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0452    1.0863    1.0144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9697   -2.3702   -0.7910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4200   -2.9307   -2.5800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7172   -1.1224   -3.7079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4748    1.1836   -2.9540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9511    1.7413   -1.0829 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9316    2.3754   -0.1097 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2801    1.8503    1.5710 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4972    2.8023    0.4734 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9293    3.6223   -0.0298 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1578    3.0784    1.6387 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5638    0.2170   -1.9098 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1972    0.7277   -1.4781 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6871   -1.2248   -2.4445 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2466   -2.1470   -1.8107 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2013   -2.8124   -0.7982 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4443   -2.6206    1.4745 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0600   -2.6500    0.3520 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6738   -0.2427    1.3183 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1285   -0.7330    2.1280 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
  5 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 12 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 11  6  1  0
 20 12  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  7 26  1  0
  8 27  1  0
  9 28  1  0
 10 29  1  0
 11 30  1  0
 13 31  1  0
 13 32  1  0
 15 33  1  0
 15 34  1  0
 15 35  1  0
 16 36  1  0
 16 37  1  0
 17 38  1  0
 17 39  1  0
 18 40  1  0
 19 41  1  0
 19 42  1  0
 20 43  1  0
 20 44  1  0
M  END

802
  Mrv0541 02271201072D          

 20 21  0  0  0  0            999 V2000
    2.5791    2.4872    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9916    3.2016    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8166    0.1227    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2291    2.4872    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8166    1.7727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5311    1.3602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1022    1.3602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5311    0.5352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1022    0.5352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4041    2.4872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0541    2.4872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8166    3.2016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2291    3.9161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4667    3.2016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4667    1.7727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1666    3.2016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8166    4.6307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2917    3.2016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2917    1.7727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7042    2.4872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 10  1  0  0  0  0
  1 16  1  0  0  0  0
  2 12  2  0  0  0  0
  3  8  1  0  0  0  0
  3  9  1  0  0  0  0
  4  5  1  0  0  0  0
  4 11  1  0  0  0  0
  4 12  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  5 10  1  0  0  0  0
  6  8  1  0  0  0  0
  7  9  1  0  0  0  0
 11 14  2  0  0  0  0
 11 15  1  0  0  0  0
 12 13  1  0  0  0  0
 13 17  1  0  0  0  0
 14 18  1  0  0  0  0
 15 19  2  0  0  0  0
 18 20  2  0  0  0  0
 19 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0061010

> <DATABASE_NAME>
hmdb

> <SMILES>
CCC(=O)N(C1=CC=CC=C1)C1(COC)CCNCC1

> <INCHI_IDENTIFIER>
InChI=1S/C16H24N2O2/c1-3-15(19)18(14-7-5-4-6-8-14)16(13-20-2)9-11-17-12-10-16/h4-8,17H,3,9-13H2,1-2H3

> <INCHI_KEY>
ULOZGJWEIWAWML-UHFFFAOYSA-N

> <FORMULA>
C16H24N2O2

> <MOLECULAR_WEIGHT>
276.374

> <EXACT_MASS>
276.183778022

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
30.840216858185734

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-[4-(methoxymethyl)piperidin-4-yl]-N-phenylpropanamide

> <ALOGPS_LOGP>
1.42

> <JCHEM_LOGP>
1.2961094939999995

> <ALOGPS_LOGS>
-2.23

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.998371847221238

> <JCHEM_POLAR_SURFACE_AREA>
41.57

> <JCHEM_REFRACTIVITY>
79.75330000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.63e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-[4-(methoxymethyl)piperidin-4-yl]-N-phenylpropanamide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0061010
     RDKit          3D
Noralfentanil
 44 45  0  0  0  0  0  0  0  0999 V2000
   -2.9541    0.5888    3.0802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6040    0.2750    1.6526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1125    0.3810    1.5115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4541    0.7304    2.5033 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4646    0.0957    0.2908 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3313   -0.2710   -0.7867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4964   -1.5477   -1.2384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3495   -1.8754   -2.2883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0510   -0.8845   -2.8938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9212    0.4086   -2.4788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0789    0.7086   -1.4470 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9632    0.1932    0.1740 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4287    1.6293    0.5097 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8254    1.5753    0.3371 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4007    2.8177    0.6038 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4250   -0.0274   -1.2472 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9865   -1.3598   -1.5603 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8190   -1.8710   -0.5003 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9431   -2.0855    0.6339 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6374   -0.6910    1.1725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8789    0.0823    3.4155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0976    1.6812    3.2193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0719    0.3330    3.7148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9834   -0.7178    1.3482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0452    1.0863    1.0144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9697   -2.3702   -0.7910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4200   -2.9307   -2.5800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7172   -1.1224   -3.7079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4748    1.1836   -2.9540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9511    1.7413   -1.0829 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9316    2.3754   -0.1097 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2801    1.8503    1.5710 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4972    2.8023    0.4734 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9293    3.6223   -0.0298 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1578    3.0784    1.6387 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5638    0.2170   -1.9098 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1972    0.7277   -1.4781 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6871   -1.2248   -2.4445 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2466   -2.1470   -1.8107 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2013   -2.8124   -0.7982 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4443   -2.6206    1.4745 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0600   -2.6500    0.3520 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6738   -0.2427    1.3183 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1285   -0.7330    2.1280 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
  5 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 12 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 11  6  1  0
 20 12  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  7 26  1  0
  8 27  1  0
  9 28  1  0
 10 29  1  0
 11 30  1  0
 13 31  1  0
 13 32  1  0
 15 33  1  0
 15 34  1  0
 15 35  1  0
 16 36  1  0
 16 37  1  0
 17 38  1  0
 17 39  1  0
 18 40  1  0
 19 41  1  0
 19 42  1  0
 20 43  1  0
 20 44  1  0
M  END

HEADER    PROTEIN                                 27-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 802                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-FEB-12         0                                  
HETATM    1  O   UNK     0       4.814   4.643   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       5.584   5.976   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0       7.124   0.229   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0       7.894   4.643   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       7.124   3.309   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.458   2.539   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.791   2.539   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.458   0.999   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.791   0.999   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.354   4.643   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.434   4.643   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.124   5.976   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.894   7.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.205   5.976   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.205   3.309   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.044   5.976   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.124   8.644   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.745   5.976   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.745   3.309   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.515   4.643   0.000  0.00  0.00           C+0
CONECT    1   10   16                                                       
CONECT    2   12                                                            
CONECT    3    8    9                                                       
CONECT    4    5   11   12                                                  
CONECT    5    4    6    7   10                                             
CONECT    6    5    8                                                       
CONECT    7    5    9                                                       
CONECT    8    3    6                                                       
CONECT    9    3    7                                                       
CONECT   10    1    5                                                       
CONECT   11    4   14   15                                                  
CONECT   12    2    4   13                                                  
CONECT   13   12   17                                                       
CONECT   14   11   18                                                       
CONECT   15   11   19                                                       
CONECT   16    1                                                            
CONECT   17   13                                                            
CONECT   18   14   20                                                       
CONECT   19   15   20                                                       
CONECT   20   18   19                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

COMPND    HMDB0061010
HETATM    1  C1  UNL     1      -2.954   0.589   3.080  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.604   0.275   1.653  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.112   0.381   1.511  1.00  0.00           C  
HETATM    4  O1  UNL     1      -0.454   0.730   2.503  1.00  0.00           O  
HETATM    5  N1  UNL     1      -0.465   0.096   0.291  1.00  0.00           N  
HETATM    6  C4  UNL     1      -1.331  -0.271  -0.787  1.00  0.00           C  
HETATM    7  C5  UNL     1      -1.496  -1.548  -1.238  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.349  -1.875  -2.288  1.00  0.00           C  
HETATM    9  C7  UNL     1      -3.051  -0.885  -2.894  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.921   0.409  -2.479  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.079   0.709  -1.447  1.00  0.00           C  
HETATM   12  C10 UNL     1       0.963   0.193   0.174  1.00  0.00           C  
HETATM   13  C11 UNL     1       1.429   1.629   0.510  1.00  0.00           C  
HETATM   14  O2  UNL     1       2.825   1.575   0.337  1.00  0.00           O  
HETATM   15  C12 UNL     1       3.401   2.818   0.604  1.00  0.00           C  
HETATM   16  C13 UNL     1       1.425  -0.027  -1.247  1.00  0.00           C  
HETATM   17  C14 UNL     1       1.987  -1.360  -1.560  1.00  0.00           C  
HETATM   18  N2  UNL     1       2.819  -1.871  -0.500  1.00  0.00           N  
HETATM   19  C15 UNL     1       1.943  -2.085   0.634  1.00  0.00           C  
HETATM   20  C16 UNL     1       1.637  -0.691   1.172  1.00  0.00           C  
HETATM   21  H1  UNL     1      -3.879   0.082   3.415  1.00  0.00           H  
HETATM   22  H2  UNL     1      -3.098   1.681   3.219  1.00  0.00           H  
HETATM   23  H3  UNL     1      -2.072   0.333   3.715  1.00  0.00           H  
HETATM   24  H4  UNL     1      -2.983  -0.718   1.348  1.00  0.00           H  
HETATM   25  H5  UNL     1      -3.045   1.086   1.014  1.00  0.00           H  
HETATM   26  H6  UNL     1      -0.970  -2.370  -0.791  1.00  0.00           H  
HETATM   27  H7  UNL     1      -2.420  -2.931  -2.580  1.00  0.00           H  
HETATM   28  H8  UNL     1      -3.717  -1.122  -3.708  1.00  0.00           H  
HETATM   29  H9  UNL     1      -3.475   1.184  -2.954  1.00  0.00           H  
HETATM   30  H10 UNL     1      -1.951   1.741  -1.083  1.00  0.00           H  
HETATM   31  H11 UNL     1       0.932   2.375  -0.110  1.00  0.00           H  
HETATM   32  H12 UNL     1       1.280   1.850   1.571  1.00  0.00           H  
HETATM   33  H13 UNL     1       4.497   2.802   0.473  1.00  0.00           H  
HETATM   34  H14 UNL     1       2.929   3.622  -0.030  1.00  0.00           H  
HETATM   35  H15 UNL     1       3.158   3.078   1.639  1.00  0.00           H  
HETATM   36  H16 UNL     1       0.564   0.217  -1.910  1.00  0.00           H  
HETATM   37  H17 UNL     1       2.197   0.728  -1.478  1.00  0.00           H  
HETATM   38  H18 UNL     1       2.687  -1.225  -2.445  1.00  0.00           H  
HETATM   39  H19 UNL     1       1.247  -2.147  -1.811  1.00  0.00           H  
HETATM   40  H20 UNL     1       3.201  -2.812  -0.798  1.00  0.00           H  
HETATM   41  H21 UNL     1       2.444  -2.621   1.475  1.00  0.00           H  
HETATM   42  H22 UNL     1       1.060  -2.650   0.352  1.00  0.00           H  
HETATM   43  H23 UNL     1       2.674  -0.243   1.318  1.00  0.00           H  
HETATM   44  H24 UNL     1       1.129  -0.733   2.128  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3   24   25
CONECT    3    4    4    5
CONECT    5    6   12
CONECT    6    7    7   11
CONECT    7    8   26
CONECT    8    9    9   27
CONECT    9   10   28
CONECT   10   11   11   29
CONECT   11   30
CONECT   12   13   16   20
CONECT   13   14   31   32
CONECT   14   15
CONECT   15   33   34   35
CONECT   16   17   36   37
CONECT   17   18   38   39
CONECT   18   19   40
CONECT   19   20   41   42
CONECT   20   43   44
END

HMDB0061010
     RDKit          3D
Noralfentanil
 44 45  0  0  0  0  0  0  0  0999 V2000
   -2.9541    0.5888    3.0802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6040    0.2750    1.6526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1125    0.3810    1.5115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4541    0.7304    2.5033 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4646    0.0957    0.2908 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3313   -0.2710   -0.7867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4964   -1.5477   -1.2384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3495   -1.8754   -2.2883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0510   -0.8845   -2.8938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9212    0.4086   -2.4788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0789    0.7086   -1.4470 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9632    0.1932    0.1740 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4287    1.6293    0.5097 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8254    1.5753    0.3371 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4007    2.8177    0.6038 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4250   -0.0274   -1.2472 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9865   -1.3598   -1.5603 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8190   -1.8710   -0.5003 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9431   -2.0855    0.6339 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6374   -0.6910    1.1725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8789    0.0823    3.4155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0976    1.6812    3.2193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0719    0.3330    3.7148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9834   -0.7178    1.3482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0452    1.0863    1.0144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9697   -2.3702   -0.7910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4200   -2.9307   -2.5800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7172   -1.1224   -3.7079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4748    1.1836   -2.9540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9511    1.7413   -1.0829 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9316    2.3754   -0.1097 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2801    1.8503    1.5710 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4972    2.8023    0.4734 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9293    3.6223   -0.0298 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1578    3.0784    1.6387 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5638    0.2170   -1.9098 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1972    0.7277   -1.4781 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6871   -1.2248   -2.4445 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2466   -2.1470   -1.8107 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2013   -2.8124   -0.7982 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4443   -2.6206    1.4745 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0600   -2.6500    0.3520 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6738   -0.2427    1.3183 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1285   -0.7330    2.1280 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
  5 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 12 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 11  6  1  0
 20 12  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  7 26  1  0
  8 27  1  0
  9 28  1  0
 10 29  1  0
 11 30  1  0
 13 31  1  0
 13 32  1  0
 15 33  1  0
 15 34  1  0
 15 35  1  0
 16 36  1  0
 16 37  1  0
 17 38  1  0
 17 39  1  0
 18 40  1  0
 19 41  1  0
 19 42  1  0
 20 43  1  0
 20 44  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-MPPP	HMDB
N-(4-(Methoxymethyl)-4-piperidinyl)-N-phenylpropanamide	HMDB
Noralfentanil, (phenyl-3-t)-labeled CPD	HMDB

Chemical Formula

C₁₆H₂₄N₂O₂

Average Molecular Weight

276.374

Monoisotopic Molecular Weight

276.183778022

IUPAC Name

N-[4-(methoxymethyl)piperidin-4-yl]-N-phenylpropanamide

Traditional Name

N-[4-(methoxymethyl)piperidin-4-yl]-N-phenylpropanamide

CAS Registry Number

61086-18-8

SMILES

CCC(=O)N(C1=CC=CC=C1)C1(COC)CCNCC1

InChI Identifier

InChI=1S/C16H24N2O2/c1-3-15(19)18(14-7-5-4-6-8-14)16(13-20-2)9-11-17-12-10-16/h4-8,17H,3,9-13H2,1-2H3

InChI Key

ULOZGJWEIWAWML-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as anilides. These are organic heterocyclic compounds derived from oxoacids RkE(=O)l(OH)m (l not 0) by replacing an OH group by the NHPh group or derivative formed by ring substitution.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Anilides

Direct Parent

Anilides

Alternative Parents

Substituents

Anilide
Piperidine
Tertiary carboxylic acid amide
Amino acid or derivatives
Carboxamide group
Carboxylic acid derivative
Dialkyl ether
Secondary aliphatic amine
Ether
Secondary amine
Organoheterocyclic compound
Azacycle
Organonitrogen compound
Carbonyl group
Organooxygen compound
Organopnictogen compound
Organic oxygen compound
Organic oxide
Amine
Hydrocarbon derivative
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 (HMDB: HMDB0061010)

Organ

Kidney (HMDB: HMDB0061010)
Liver (HMDB: HMDB0061010)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0061010)

Cellular substructure

Cytoplasm (HMDB: HMDB0061010)

Source

Endogenous

Endogenous (HMDB: HMDB0061010)

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	1.63 g/L	ALOGPS
logP	1.42	ALOGPS
logP	1.3	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Basic)	10	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	41.57 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	79.75 m³·mol⁻¹	ChemAxon
Polarizability	30.84 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
DarkChem	[M+H]+	162.712	31661259
DarkChem	[M-H]-	164.33	31661259
DeepCCS	[M+H]+	164.634	30932474
DeepCCS	[M-H]-	162.277	30932474
DeepCCS	[M-2H]-	195.162	30932474
DeepCCS	[M+Na]+	170.728	30932474
AllCCS	[M+H]+	165.5	32859911
AllCCS	[M+H-H2O]+	162.0	32859911
AllCCS	[M+NH4]+	168.7	32859911
AllCCS	[M+Na]+	169.6	32859911
AllCCS	[M-H]-	168.3	32859911
AllCCS	[M+Na-2H]-	168.6	32859911
AllCCS	[M+HCOO]-	169.0	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.	3.43 minutes	32390414
Predicted by Siyang on May 30, 2022	10.0003 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.23 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1243.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	194.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	141.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	164.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	53.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	256.3 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	298.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	265.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	736.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	302.9 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	1002.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	233.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	235.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	340.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	296.5 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	29.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Noralfentanil	CCC(=O)N(C1=CC=CC=C1)C1(COC)CCNCC1	3201.9	Standard polar	33892256
Noralfentanil	CCC(=O)N(C1=CC=CC=C1)C1(COC)CCNCC1	2111.7	Standard non polar	33892256
Noralfentanil	CCC(=O)N(C1=CC=CC=C1)C1(COC)CCNCC1	2091.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Noralfentanil,1TMS,isomer #1	CCC(=O)N(C1=CC=CC=C1)C1(COC)CCN([Si](C)(C)C)CC1	2154.2	Semi standard non polar	33892256
Noralfentanil,1TMS,isomer #1	CCC(=O)N(C1=CC=CC=C1)C1(COC)CCN([Si](C)(C)C)CC1	2210.5	Standard non polar	33892256
Noralfentanil,1TMS,isomer #1	CCC(=O)N(C1=CC=CC=C1)C1(COC)CCN([Si](C)(C)C)CC1	2829.3	Standard polar	33892256
Noralfentanil,1TBDMS,isomer #1	CCC(=O)N(C1=CC=CC=C1)C1(COC)CCN([Si](C)(C)C(C)(C)C)CC1	2402.3	Semi standard non polar	33892256
Noralfentanil,1TBDMS,isomer #1	CCC(=O)N(C1=CC=CC=C1)C1(COC)CCN([Si](C)(C)C(C)(C)C)CC1	2404.3	Standard non polar	33892256
Noralfentanil,1TBDMS,isomer #1	CCC(=O)N(C1=CC=CC=C1)C1(COC)CCN([Si](C)(C)C(C)(C)C)CC1	2954.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Noralfentanil GC-MS (Non-derivatized) - 70eV, Positive	splash10-004l-7960000000-e3902ef7785f3e4fcae7	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Noralfentanil GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Noralfentanil 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 - Noralfentanil 10V, Positive-QTOF	splash10-004i-0090000000-b50f8d64da344bd3f0d4	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Noralfentanil 20V, Positive-QTOF	splash10-0551-6690000000-bb9bf87f38d973378d29	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Noralfentanil 40V, Positive-QTOF	splash10-0a73-9510000000-0eee630156a75a36bed4	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Noralfentanil 10V, Negative-QTOF	splash10-004i-0090000000-255fc5f958d9915651e1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Noralfentanil 20V, Negative-QTOF	splash10-00mt-2390000000-fbc2b068bf2b3541abff	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Noralfentanil 40V, Negative-QTOF	splash10-05fu-6930000000-3bf8909d6063abcd58df	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Noralfentanil 10V, Negative-QTOF	splash10-004i-0090000000-1213655852961d5e7fbf	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Noralfentanil 20V, Negative-QTOF	splash10-052g-9800000000-64ce4e6b4b9c955d7b35	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Noralfentanil 40V, Negative-QTOF	splash10-0006-9710000000-7b6db57377a8449e2a00	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Noralfentanil 10V, Positive-QTOF	splash10-004i-0090000000-fb5857ed89f2e0e25f59	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Noralfentanil 20V, Positive-QTOF	splash10-002b-9670000000-d9df0f9e679f27e0a446	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Noralfentanil 40V, Positive-QTOF	splash10-002v-6900000000-a50554a475db51dc35c3	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

162172

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 Noralfentanil (HMDB0061010)

MOL for HMDB0061010 (Noralfentanil)

3D MOL for HMDB0061010 (Noralfentanil)

3D SDF for HMDB0061010 (Noralfentanil)

3D-SDF for HMDB0061010 (Noralfentanil)

PDB for HMDB0061010 (Noralfentanil)

3D PDB for HMDB0061010 (Noralfentanil)

SMILES for HMDB0061010 (Noralfentanil)

INCHI for HMDB0061010 (Noralfentanil)

Structure for HMDB0061010 (Noralfentanil)

3D Structure for HMDB0061010 (Noralfentanil)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra