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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-07-09 16:12:09 UTC

Update Date

2019-07-23 07:15:33 UTC

HMDB ID

HMDB0061006

Secondary Accession Numbers

HMDB61006

Metabolite Identification

Common Name

norfentanyl

Description

norfentanyl is a metabolite of fentanyl. Fentanyl (also known as fentanil, brand names Sublimaze, Actiq, Durogesic, Duragesic, Fentora, Matrifen, Haldid, Onsolis, Instanyl, Abstral, Lazanda and others) is a potent, synthetic narcotic analgesic with a rapid onset and short duration of action. It is a strong agonist at the μ-opioid receptors. Historically it has been used to treat breakthrough pain and is commonly used in pre-procedures as a pain reliever as well as an anesthetic in combination with a benzodiazepine. (Wikipedia)

Structure

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

HMDB0061006
     RDKit          3D
norfentanyl
 37 38  0  0  0  0  0  0  0  0999 V2000
    0.0923    4.3350    0.5543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5246    2.9877    0.2333 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4872    1.9423    0.4054 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6563    2.2716    0.7941 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1977    0.5345    0.1423 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2726   -0.3535    0.3057 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3274   -1.3630    1.2087 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4530   -2.2032    1.3227 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5416   -2.0129    0.5054 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5110   -0.9957   -0.4185 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4043   -0.1833   -0.5189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1384    0.2077   -0.3025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8847   -0.4910    0.7805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1543   -1.9310    0.5452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5842   -2.2294   -0.7987 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5669   -1.8481   -1.7199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1067   -0.4214   -1.6258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0099    4.6008    1.6164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4146    5.1541   -0.0126 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1794    4.2961    0.3154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9099    3.0316   -0.8311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4247    2.8022    0.8692 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4897   -1.5330    1.8690 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3966   -2.9830    2.0780 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3883   -2.6799    0.6229 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3485   -0.8343   -1.0580 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3516    0.6305   -1.2463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6779    1.2089   -0.4017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4517   -0.3362    1.7815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9246   -0.0187    0.9118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0020   -2.2897    1.2030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3094   -2.6085    0.7671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5306   -1.8633   -1.0245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9711   -2.0550   -2.7568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6882   -2.5377   -1.6436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0814   -0.3790   -2.0988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7421    0.1476   -2.3744 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
 15 16  1  0
 16 17  1  0
 11  6  1  0
 17 12  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  7 23  1  0
  8 24  1  0
  9 25  1  0
 10 26  1  0
 11 27  1  0
 12 28  1  0
 13 29  1  0
 13 30  1  0
 14 31  1  0
 14 32  1  0
 15 33  1  0
 16 34  1  0
 16 35  1  0
 17 36  1  0
 17 37  1  0
M  END

813
  Mrv0541 02271201042D          

 17 18  0  0  0  0            999 V2000
    1.6500    2.2688    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.2063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    2.2688    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    3.5063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    3.5063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    3.9188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    3.9188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    3.5063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 10  2  0  0  0  0
  2  7  1  0  0  0  0
  2  8  1  0  0  0  0
  3  4  1  0  0  0  0
  3  9  1  0  0  0  0
  3 10  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  5  7  1  0  0  0  0
  6  8  1  0  0  0  0
  9 12  2  0  0  0  0
  9 13  1  0  0  0  0
 10 11  1  0  0  0  0
 11 14  1  0  0  0  0
 12 15  1  0  0  0  0
 13 16  2  0  0  0  0
 15 17  2  0  0  0  0
 16 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0061006

> <DATABASE_NAME>
hmdb

> <SMILES>
CCC(=O)N(C1CCNCC1)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C14H20N2O/c1-2-14(17)16(12-6-4-3-5-7-12)13-8-10-15-11-9-13/h3-7,13,15H,2,8-11H2,1H3

> <INCHI_KEY>
PMCBDBWCQQBSRJ-UHFFFAOYSA-N

> <FORMULA>
C14H20N2O

> <MOLECULAR_WEIGHT>
232.3214

> <EXACT_MASS>
232.157563272

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
26.45569827434535

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-phenyl-N-(piperidin-4-yl)propanamide

> <ALOGPS_LOGP>
2.00

> <JCHEM_LOGP>
1.4193162886666668

> <ALOGPS_LOGS>
-2.39

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
10.027796317997975

> <JCHEM_POLAR_SURFACE_AREA>
32.34

> <JCHEM_REFRACTIVITY>
68.82020000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.50e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
norfentanyl

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0061006
     RDKit          3D
norfentanyl
 37 38  0  0  0  0  0  0  0  0999 V2000
    0.0923    4.3350    0.5543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5246    2.9877    0.2333 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4872    1.9423    0.4054 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6563    2.2716    0.7941 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1977    0.5345    0.1423 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2726   -0.3535    0.3057 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3274   -1.3630    1.2087 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4530   -2.2032    1.3227 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5416   -2.0129    0.5054 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5110   -0.9957   -0.4185 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4043   -0.1833   -0.5189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1384    0.2077   -0.3025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8847   -0.4910    0.7805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1543   -1.9310    0.5452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5842   -2.2294   -0.7987 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5669   -1.8481   -1.7199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1067   -0.4214   -1.6258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0099    4.6008    1.6164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4146    5.1541   -0.0126 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1794    4.2961    0.3154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9099    3.0316   -0.8311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4247    2.8022    0.8692 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4897   -1.5330    1.8690 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3966   -2.9830    2.0780 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3883   -2.6799    0.6229 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3485   -0.8343   -1.0580 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3516    0.6305   -1.2463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6779    1.2089   -0.4017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4517   -0.3362    1.7815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9246   -0.0187    0.9118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0020   -2.2897    1.2030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3094   -2.6085    0.7671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5306   -1.8633   -1.0245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9711   -2.0550   -2.7568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6882   -2.5377   -1.6436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0814   -0.3790   -2.0988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7421    0.1476   -2.3744 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
 15 16  1  0
 16 17  1  0
 11  6  1  0
 17 12  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  7 23  1  0
  8 24  1  0
  9 25  1  0
 10 26  1  0
 11 27  1  0
 12 28  1  0
 13 29  1  0
 13 30  1  0
 14 31  1  0
 14 32  1  0
 15 33  1  0
 16 34  1  0
 16 35  1  0
 17 36  1  0
 17 37  1  0
M  END

HEADER    PROTEIN                                 27-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 813                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-FEB-12         0                                  
HETATM    1  O   UNK     0       3.080   4.235   0.000  0.00  0.00           O+0
HETATM    2  N   UNK     0       5.748  -0.385   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0       5.748   4.235   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       5.748   2.695   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.081   1.925   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.414   1.925   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.081   0.385   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.414   0.385   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.081   5.005   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.414   5.005   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.414   6.545   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.081   6.545   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.415   4.235   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.080   7.315   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.415   7.315   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.748   5.005   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.748   6.545   0.000  0.00  0.00           C+0
CONECT    1   10                                                            
CONECT    2    7    8                                                       
CONECT    3    4    9   10                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4    7                                                       
CONECT    6    4    8                                                       
CONECT    7    2    5                                                       
CONECT    8    2    6                                                       
CONECT    9    3   12   13                                                  
CONECT   10    1    3   11                                                  
CONECT   11   10   14                                                       
CONECT   12    9   15                                                       
CONECT   13    9   16                                                       
CONECT   14   11                                                            
CONECT   15   12   17                                                       
CONECT   16   13   17                                                       
CONECT   17   15   16                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

COMPND    HMDB0061006
HETATM    1  C1  UNL     1       0.092   4.335   0.554  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.525   2.988   0.233  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.487   1.942   0.405  1.00  0.00           C  
HETATM    4  O1  UNL     1       1.656   2.272   0.794  1.00  0.00           O  
HETATM    5  N1  UNL     1       0.198   0.535   0.142  1.00  0.00           N  
HETATM    6  C4  UNL     1       1.273  -0.354   0.306  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.327  -1.363   1.209  1.00  0.00           C  
HETATM    8  C6  UNL     1       2.453  -2.203   1.323  1.00  0.00           C  
HETATM    9  C7  UNL     1       3.542  -2.013   0.505  1.00  0.00           C  
HETATM   10  C8  UNL     1       3.511  -0.996  -0.418  1.00  0.00           C  
HETATM   11  C9  UNL     1       2.404  -0.183  -0.519  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.138   0.208  -0.302  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.885  -0.491   0.781  1.00  0.00           C  
HETATM   14  C12 UNL     1      -2.154  -1.931   0.545  1.00  0.00           C  
HETATM   15  N2  UNL     1      -2.584  -2.229  -0.799  1.00  0.00           N  
HETATM   16  C13 UNL     1      -1.567  -1.848  -1.720  1.00  0.00           C  
HETATM   17  C14 UNL     1      -1.107  -0.421  -1.626  1.00  0.00           C  
HETATM   18  H1  UNL     1      -0.010   4.601   1.616  1.00  0.00           H  
HETATM   19  H2  UNL     1      -0.415   5.154  -0.013  1.00  0.00           H  
HETATM   20  H3  UNL     1       1.179   4.296   0.315  1.00  0.00           H  
HETATM   21  H4  UNL     1      -0.910   3.032  -0.831  1.00  0.00           H  
HETATM   22  H5  UNL     1      -1.425   2.802   0.869  1.00  0.00           H  
HETATM   23  H6  UNL     1       0.490  -1.533   1.869  1.00  0.00           H  
HETATM   24  H7  UNL     1       2.397  -2.983   2.078  1.00  0.00           H  
HETATM   25  H8  UNL     1       4.388  -2.680   0.623  1.00  0.00           H  
HETATM   26  H9  UNL     1       4.349  -0.834  -1.058  1.00  0.00           H  
HETATM   27  H10 UNL     1       2.352   0.631  -1.246  1.00  0.00           H  
HETATM   28  H11 UNL     1      -1.678   1.209  -0.402  1.00  0.00           H  
HETATM   29  H12 UNL     1      -1.452  -0.336   1.781  1.00  0.00           H  
HETATM   30  H13 UNL     1      -2.925  -0.019   0.912  1.00  0.00           H  
HETATM   31  H14 UNL     1      -3.002  -2.290   1.203  1.00  0.00           H  
HETATM   32  H15 UNL     1      -1.309  -2.608   0.767  1.00  0.00           H  
HETATM   33  H16 UNL     1      -3.531  -1.863  -1.024  1.00  0.00           H  
HETATM   34  H17 UNL     1      -1.971  -2.055  -2.757  1.00  0.00           H  
HETATM   35  H18 UNL     1      -0.688  -2.538  -1.644  1.00  0.00           H  
HETATM   36  H19 UNL     1      -0.081  -0.379  -2.099  1.00  0.00           H  
HETATM   37  H20 UNL     1      -1.742   0.148  -2.374  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3   21   22
CONECT    3    4    4    5
CONECT    5    6   12
CONECT    6    7    7   11
CONECT    7    8   23
CONECT    8    9    9   24
CONECT    9   10   25
CONECT   10   11   11   26
CONECT   11   27
CONECT   12   13   17   28
CONECT   13   14   29   30
CONECT   14   15   31   32
CONECT   15   16   33
CONECT   16   17   34   35
CONECT   17   36   37
END

HMDB0061006
     RDKit          3D
norfentanyl
 37 38  0  0  0  0  0  0  0  0999 V2000
    0.0923    4.3350    0.5543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5246    2.9877    0.2333 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4872    1.9423    0.4054 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6563    2.2716    0.7941 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1977    0.5345    0.1423 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2726   -0.3535    0.3057 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3274   -1.3630    1.2087 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4530   -2.2032    1.3227 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5416   -2.0129    0.5054 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5110   -0.9957   -0.4185 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4043   -0.1833   -0.5189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1384    0.2077   -0.3025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8847   -0.4910    0.7805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1543   -1.9310    0.5452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5842   -2.2294   -0.7987 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5669   -1.8481   -1.7199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1067   -0.4214   -1.6258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0099    4.6008    1.6164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4146    5.1541   -0.0126 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1794    4.2961    0.3154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9099    3.0316   -0.8311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4247    2.8022    0.8692 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4897   -1.5330    1.8690 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3966   -2.9830    2.0780 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3883   -2.6799    0.6229 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3485   -0.8343   -1.0580 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3516    0.6305   -1.2463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6779    1.2089   -0.4017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4517   -0.3362    1.7815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9246   -0.0187    0.9118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0020   -2.2897    1.2030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3094   -2.6085    0.7671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5306   -1.8633   -1.0245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9711   -2.0550   -2.7568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6882   -2.5377   -1.6436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0814   -0.3790   -2.0988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7421    0.1476   -2.3744 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
 15 16  1  0
 16 17  1  0
 11  6  1  0
 17 12  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  7 23  1  0
  8 24  1  0
  9 25  1  0
 10 26  1  0
 11 27  1  0
 12 28  1  0
 13 29  1  0
 13 30  1  0
 14 31  1  0
 14 32  1  0
 15 33  1  0
 16 34  1  0
 16 35  1  0
 17 36  1  0
 17 37  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-(N'-phenyl-n'-propionyl)aminopiperidine	ChEBI
4-(N-Propionylanilino)piperidine	ChEBI
N-Phenyl-N-(piperidin-4-yl)propionamide	ChEBI
N-Phenyl-N-4-piperidinylpropanamide	ChEBI
N-Phenyl-N-4-piperidinylpropionamide	ChEBI
Norfentanyl monohydrochloride	HMDB

Chemical Formula

C₁₄H₂₀N₂O

Average Molecular Weight

232.3214

Monoisotopic Molecular Weight

232.157563272

IUPAC Name

N-phenyl-N-(piperidin-4-yl)propanamide

Traditional Name

norfentanyl

CAS Registry Number

Not Available

SMILES

CCC(=O)N(C1CCNCC1)C1=CC=CC=C1

InChI Identifier

InChI=1S/C14H20N2O/c1-2-14(17)16(12-6-4-3-5-7-12)13-8-10-15-11-9-13/h3-7,13,15H,2,8-11H2,1H3

InChI Key

PMCBDBWCQQBSRJ-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
Secondary aliphatic amine
Secondary amine
Organoheterocyclic compound
Azacycle
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Amine
Organic oxide
Carbonyl group
Hydrocarbon derivative
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

piperidines (CHEBI:62685 )
monocarboxylic acid amide (CHEBI:62685 )
anilide (CHEBI:62685 )

Ontology

Not Available

Kidney (HMDB: HMDB0061006)
Liver (HMDB: HMDB0061006)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0061006)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0061006)

Cellular substructure

Cytoplasm (HMDB: HMDB0061006)

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	0.95 g/L	ALOGPS
logP	2	ALOGPS
logP	1.42	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Basic)	10.03	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	32.34 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	68.82 m³·mol⁻¹	ChemAxon
Polarizability	26.46 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]+	154.562	31661259
DarkChem	[M-H]-	154.033	31661259
DeepCCS	[M+H]+	152.905	30932474
DeepCCS	[M-H]-	150.547	30932474
DeepCCS	[M-2H]-	184.049	30932474
DeepCCS	[M+Na]+	158.999	30932474
AllCCS	[M+H]+	155.6	32859911
AllCCS	[M+H-H2O]+	151.8	32859911
AllCCS	[M+NH4]+	159.2	32859911
AllCCS	[M+Na]+	160.2	32859911
AllCCS	[M-H]-	157.9	32859911
AllCCS	[M+Na-2H]-	158.1	32859911
AllCCS	[M+HCOO]-	158.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
norfentanyl	CCC(=O)N(C1CCNCC1)C1=CC=CC=C1	2957.6	Standard polar	33892256
norfentanyl	CCC(=O)N(C1CCNCC1)C1=CC=CC=C1	2028.9	Standard non polar	33892256
norfentanyl	CCC(=O)N(C1CCNCC1)C1=CC=CC=C1	1996.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
norfentanyl,1TMS,isomer #1	CCC(=O)N(C1=CC=CC=C1)C1CCN([Si](C)(C)C)CC1	2051.8	Semi standard non polar	33892256
norfentanyl,1TMS,isomer #1	CCC(=O)N(C1=CC=CC=C1)C1CCN([Si](C)(C)C)CC1	1997.0	Standard non polar	33892256
norfentanyl,1TMS,isomer #1	CCC(=O)N(C1=CC=CC=C1)C1CCN([Si](C)(C)C)CC1	2661.7	Standard polar	33892256
norfentanyl,1TBDMS,isomer #1	CCC(=O)N(C1=CC=CC=C1)C1CCN([Si](C)(C)C(C)(C)C)CC1	2283.8	Semi standard non polar	33892256
norfentanyl,1TBDMS,isomer #1	CCC(=O)N(C1=CC=CC=C1)C1CCN([Si](C)(C)C(C)(C)C)CC1	2193.4	Standard non polar	33892256
norfentanyl,1TBDMS,isomer #1	CCC(=O)N(C1=CC=CC=C1)C1CCN([Si](C)(C)C(C)(C)C)CC1	2799.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - norfentanyl GC-MS (Non-derivatized) - 70eV, Positive	splash10-005c-9810000000-3caed077ea7a0ee21ff1	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - norfentanyl 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - norfentanyl LC-ESI-QTOF , positive-QTOF	splash10-001i-0090000000-30023a9a668dad77c171	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - norfentanyl LC-ESI-QTOF , positive-QTOF	splash10-001i-0490000000-67cd08c1a84bf833feb6	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - norfentanyl LC-ESI-QTOF , positive-QTOF	splash10-0udi-0910000000-a687d66216f3f0f2a542	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - norfentanyl LC-ESI-QTOF , positive-QTOF	splash10-0ue9-0900000000-172bf948c02a137b45d8	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - norfentanyl LC-ESI-QTOF , positive-QTOF	splash10-0f89-0900000000-4dbe3aa7aa26725f2384	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - norfentanyl LC-ESI-QFT , positive-QTOF	splash10-001i-1090000000-0a49897fffa5fde5c225	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - norfentanyl LC-ESI-QFT , positive-QTOF	splash10-001i-9170000000-bfce9be1027a8de7e1e8	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - norfentanyl LC-ESI-QFT , positive-QTOF	splash10-001i-9000000000-850655b66d289ffd449c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - norfentanyl LC-ESI-QFT , positive-QTOF	splash10-001i-9000000000-ad4c9ad4e989e47126dd	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - norfentanyl LC-ESI-QFT , positive-QTOF	splash10-0a59-9000000000-0f96dbb8a332c80da86d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - norfentanyl LC-ESI-QFT , positive-QTOF	splash10-0a4i-9000000000-8bb94389e58a6b848a31	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - norfentanyl LC-ESI-QFT , positive-QTOF	splash10-0a4i-9000000000-8de4a5f24b02ee65a584	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - norfentanyl LC-ESI-QFT , positive-QTOF	splash10-0a4i-9000000000-3728a8f7f46a40ff76ec	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - norfentanyl LC-ESI-QFT , positive-QTOF	splash10-0a4i-9000000000-6d3cc832e8a6d431c3b8	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - norfentanyl 50V, Positive-QTOF	splash10-0f89-0900000000-4dbe3aa7aa26725f2384	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - norfentanyl 40V, Positive-QTOF	splash10-0ue9-0900000000-d764b890a85df217086c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - norfentanyl 15V, Positive-QTOF	splash10-001i-1090000000-fad8ab78c63174bbb4df	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - norfentanyl 30V, Positive-QTOF	splash10-0udi-0910000000-a687d66216f3f0f2a542	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - norfentanyl 40V, Positive-QTOF	splash10-0ue9-0900000000-172bf948c02a137b45d8	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - norfentanyl 10V, Positive-QTOF	splash10-001i-1290000000-2e8cba986c947fbed455	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - norfentanyl 20V, Positive-QTOF	splash10-003r-9440000000-7f5a511cb9530706b2ee	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - norfentanyl 40V, Positive-QTOF	splash10-001i-9100000000-1134c041265e979217df	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - norfentanyl 10V, Negative-QTOF	splash10-001i-0090000000-43b32b3b4df368ab5904	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - norfentanyl 20V, Negative-QTOF	splash10-003r-4690000000-47ce59bca6771457156a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - norfentanyl 40V, Negative-QTOF	splash10-054p-9500000000-f60fe31246330ad46c99	2016-08-03	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

259381

PDB ID

Not Available

ChEBI ID

62685

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 norfentanyl (HMDB0061006)

MOL for HMDB0061006 (norfentanyl)

3D MOL for HMDB0061006 (norfentanyl)

3D SDF for HMDB0061006 (norfentanyl)

3D-SDF for HMDB0061006 (norfentanyl)

PDB for HMDB0061006 (norfentanyl)

3D PDB for HMDB0061006 (norfentanyl)

SMILES for HMDB0061006 (norfentanyl)

INCHI for HMDB0061006 (norfentanyl)

Structure for HMDB0061006 (norfentanyl)

3D Structure for HMDB0061006 (norfentanyl)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra