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enzymes (1) Show 1 protein

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:52 UTC

Update Date

2022-03-07 02:52:00 UTC

HMDB ID

HMDB0015508

Secondary Accession Numbers

HMDB15508

Metabolite Identification

Common Name

Fencamfamine

Description

Fencamfamine (Glucoenergan, Reactivan) is a stimulant which was developed in the 1960s as an appetite suppressant, but was later withdrawn for this application due to problems with dependence and abuse. It is around half the potency of dexamphetamine, and is prescribed at a dose of 10-60mg, although abusers of the drug tend to rapidly develop tolerance and escalate their dose. Reactivan is still rarely used for treating depressive day-time fatigue, lack of concentration and lethargy, particularly in individuals who have chronic medical conditions, as its favourable safety profile makes it the most suitable drug in some cases. [Wikipedia ]

Structure

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

HMDB0015508
     RDKit          3D
Fencamfamine
 37 39  0  0  0  0  0  0  0  0999 V2000
   -2.4688   -3.0568    0.0462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4855   -1.5327   -0.1289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0850   -1.1295   -0.1173 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9245    0.2808   -0.2753 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5154    1.1211    0.8319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8400    2.4812    0.2498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4646    3.0345   -0.0673 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5219    1.9833    0.4746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2952    1.5501    1.6672 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4360    0.8068   -0.4531 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5687   -0.0973   -0.4645 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0075   -0.9068    0.5596 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1045   -1.7486    0.4660 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8316   -1.8165   -0.6970 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4311   -1.0306   -1.7371 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3391   -0.1989   -1.6301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3548   -3.5234   -0.9704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3699   -3.3977    0.5648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5874   -3.3676    0.6276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9822   -1.1157    0.7518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9997   -1.2546   -1.0607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7473   -1.3821    0.8613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5799    0.5145   -1.1771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2929    0.6753    1.4130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4561    2.3264   -0.6575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3737    3.1148    0.9942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3146    3.9472    0.5459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3089    3.2015   -1.1491 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4955    2.3683    0.6786 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1133    0.7893    2.2953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5567    2.4972    2.2135 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4349    1.3184   -1.4862 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4853   -0.8944    1.4775 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4076   -2.3615    1.2959 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6978   -2.4867   -0.7592 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0215   -1.0971   -2.6561 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1066    0.3879   -2.5280 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  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 10  4  1  0
 16 11  1  0
  9  5  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  3 22  1  0
  4 23  1  0
  5 24  1  0
  6 25  1  0
  6 26  1  0
  7 27  1  0
  7 28  1  0
  8 29  1  0
  9 30  1  0
  9 31  1  0
 10 32  1  0
 12 33  1  0
 13 34  1  0
 14 35  1  0
 15 36  1  0
 16 37  1  0
M  END

1463
  Mrv0541 02231215302D          

 16 18  0  0  1  0            999 V2000
    2.6602    0.9070    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2984    0.8040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5119    1.6008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8696   -0.0210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4571    0.6934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9042    2.4115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8097    0.1780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0231    0.9748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6561   -0.8177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4467    1.7039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8592   -1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2394   -1.4011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6499    1.9173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6457   -1.8282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0258   -2.1979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2289   -2.4115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  1  0  0  0  0
  1 10  1  0  0  0  0
  2  4  1  0  0  0  0
  2  6  1  0  0  0  0
  2  7  1  0  0  0  0
  3  5  1  0  0  0  0
  3  6  1  0  0  0  0
  3  8  1  0  0  0  0
  4  5  1  0  0  0  0
  4  9  1  0  0  0  0
  7  8  1  0  0  0  0
  9 11  2  0  0  0  0
  9 12  1  0  0  0  0
 10 13  1  0  0  0  0
 11 14  1  0  0  0  0
 12 15  2  0  0  0  0
 14 16  2  0  0  0  0
 15 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015508

> <DATABASE_NAME>
hmdb

> <SMILES>
CCNC1C2CCC(C2)C1C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H21N/c1-2-16-15-13-9-8-12(10-13)14(15)11-6-4-3-5-7-11/h3-7,12-16H,2,8-10H2,1H3

> <INCHI_KEY>
IKFBPFGUINLYQI-UHFFFAOYSA-N

> <FORMULA>
C15H21N

> <MOLECULAR_WEIGHT>
215.3339

> <EXACT_MASS>
215.167399677

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
26.12991500811218

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-ethyl-3-phenylbicyclo[2.2.1]heptan-2-amine

> <ALOGPS_LOGP>
3.46

> <JCHEM_LOGP>
3.2056741686666665

> <ALOGPS_LOGS>
-4.86

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
10.563142373934664

> <JCHEM_POLAR_SURFACE_AREA>
12.03

> <JCHEM_REFRACTIVITY>
67.63980000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.95e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
fencamfamine

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0015508
     RDKit          3D
Fencamfamine
 37 39  0  0  0  0  0  0  0  0999 V2000
   -2.4688   -3.0568    0.0462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4855   -1.5327   -0.1289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0850   -1.1295   -0.1173 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9245    0.2808   -0.2753 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5154    1.1211    0.8319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8400    2.4812    0.2498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4646    3.0345   -0.0673 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5219    1.9833    0.4746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2952    1.5501    1.6672 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4360    0.8068   -0.4531 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5687   -0.0973   -0.4645 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0075   -0.9068    0.5596 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1045   -1.7486    0.4660 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8316   -1.8165   -0.6970 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4311   -1.0306   -1.7371 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3391   -0.1989   -1.6301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3548   -3.5234   -0.9704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3699   -3.3977    0.5648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5874   -3.3676    0.6276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9822   -1.1157    0.7518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9997   -1.2546   -1.0607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7473   -1.3821    0.8613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5799    0.5145   -1.1771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2929    0.6753    1.4130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4561    2.3264   -0.6575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3737    3.1148    0.9942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3146    3.9472    0.5459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3089    3.2015   -1.1491 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4955    2.3683    0.6786 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1133    0.7893    2.2953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5567    2.4972    2.2135 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4349    1.3184   -1.4862 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4853   -0.8944    1.4775 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4076   -2.3615    1.2959 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6978   -2.4867   -0.7592 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0215   -1.0971   -2.6561 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1066    0.3879   -2.5280 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  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 10  4  1  0
 16 11  1  0
  9  5  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  3 22  1  0
  4 23  1  0
  5 24  1  0
  6 25  1  0
  6 26  1  0
  7 27  1  0
  7 28  1  0
  8 29  1  0
  9 30  1  0
  9 31  1  0
 10 32  1  0
 12 33  1  0
 13 34  1  0
 14 35  1  0
 15 36  1  0
 16 37  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1463                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  N   UNK     0       4.966   1.693   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       9.890   1.501   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.289   2.988   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.223  -0.039   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.453   1.294   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.155   4.501   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.711   0.332   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      13.110   1.820   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.825  -1.526   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.567   3.181   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.337  -1.925   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.913  -2.615   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.080   3.579   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.939  -3.413   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.515  -4.103   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.027  -4.501   0.000  0.00  0.00           C+0
CONECT    1    5   10                                                       
CONECT    2    4    6    7                                                  
CONECT    3    5    6    8                                                  
CONECT    4    2    5    9                                                  
CONECT    5    1    3    4                                                  
CONECT    6    2    3                                                       
CONECT    7    2    8                                                       
CONECT    8    3    7                                                       
CONECT    9    4   11   12                                                  
CONECT   10    1   13                                                       
CONECT   11    9   14                                                       
CONECT   12    9   15                                                       
CONECT   13   10                                                            
CONECT   14   11   16                                                       
CONECT   15   12   16                                                       
CONECT   16   14   15                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   36    0
END

COMPND    HMDB0015508
HETATM    1  C1  UNL     1      -2.469  -3.057   0.046  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.486  -1.533  -0.129  1.00  0.00           C  
HETATM    3  N1  UNL     1      -1.085  -1.129  -0.117  1.00  0.00           N  
HETATM    4  C3  UNL     1      -0.924   0.281  -0.275  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.515   1.121   0.832  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.840   2.481   0.250  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.465   3.034  -0.067  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.522   1.983   0.475  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.295   1.550   1.667  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.436   0.807  -0.453  1.00  0.00           C  
HETATM   11  C10 UNL     1       1.569  -0.097  -0.465  1.00  0.00           C  
HETATM   12  C11 UNL     1       2.008  -0.907   0.560  1.00  0.00           C  
HETATM   13  C12 UNL     1       3.105  -1.749   0.466  1.00  0.00           C  
HETATM   14  C13 UNL     1       3.832  -1.816  -0.697  1.00  0.00           C  
HETATM   15  C14 UNL     1       3.431  -1.031  -1.737  1.00  0.00           C  
HETATM   16  C15 UNL     1       2.339  -0.199  -1.630  1.00  0.00           C  
HETATM   17  H1  UNL     1      -2.355  -3.523  -0.970  1.00  0.00           H  
HETATM   18  H2  UNL     1      -3.370  -3.398   0.565  1.00  0.00           H  
HETATM   19  H3  UNL     1      -1.587  -3.368   0.628  1.00  0.00           H  
HETATM   20  H4  UNL     1      -2.982  -1.116   0.752  1.00  0.00           H  
HETATM   21  H5  UNL     1      -3.000  -1.255  -1.061  1.00  0.00           H  
HETATM   22  H6  UNL     1      -0.747  -1.382   0.861  1.00  0.00           H  
HETATM   23  H7  UNL     1      -1.580   0.514  -1.177  1.00  0.00           H  
HETATM   24  H8  UNL     1      -2.293   0.675   1.413  1.00  0.00           H  
HETATM   25  H9  UNL     1      -2.456   2.326  -0.657  1.00  0.00           H  
HETATM   26  H10 UNL     1      -2.374   3.115   0.994  1.00  0.00           H  
HETATM   27  H11 UNL     1      -0.315   3.947   0.546  1.00  0.00           H  
HETATM   28  H12 UNL     1      -0.309   3.202  -1.149  1.00  0.00           H  
HETATM   29  H13 UNL     1       1.495   2.368   0.679  1.00  0.00           H  
HETATM   30  H14 UNL     1       0.113   0.789   2.295  1.00  0.00           H  
HETATM   31  H15 UNL     1      -0.557   2.497   2.213  1.00  0.00           H  
HETATM   32  H16 UNL     1       0.435   1.318  -1.486  1.00  0.00           H  
HETATM   33  H17 UNL     1       1.485  -0.894   1.478  1.00  0.00           H  
HETATM   34  H18 UNL     1       3.408  -2.362   1.296  1.00  0.00           H  
HETATM   35  H19 UNL     1       4.698  -2.487  -0.759  1.00  0.00           H  
HETATM   36  H20 UNL     1       4.022  -1.097  -2.656  1.00  0.00           H  
HETATM   37  H21 UNL     1       2.107   0.388  -2.528  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3   20   21
CONECT    3    4   22
CONECT    4    5   10   23
CONECT    5    6    9   24
CONECT    6    7   25   26
CONECT    7    8   27   28
CONECT    8    9   10   29
CONECT    9   30   31
CONECT   10   11   32
CONECT   11   12   12   16
CONECT   12   13   33
CONECT   13   14   14   34
CONECT   14   15   35
CONECT   15   16   16   36
CONECT   16   37
END

HMDB0015508
     RDKit          3D
Fencamfamine
 37 39  0  0  0  0  0  0  0  0999 V2000
   -2.4688   -3.0568    0.0462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4855   -1.5327   -0.1289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0850   -1.1295   -0.1173 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9245    0.2808   -0.2753 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5154    1.1211    0.8319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8400    2.4812    0.2498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4646    3.0345   -0.0673 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5219    1.9833    0.4746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2952    1.5501    1.6672 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4360    0.8068   -0.4531 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5687   -0.0973   -0.4645 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0075   -0.9068    0.5596 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1045   -1.7486    0.4660 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8316   -1.8165   -0.6970 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4311   -1.0306   -1.7371 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3391   -0.1989   -1.6301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3548   -3.5234   -0.9704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3699   -3.3977    0.5648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5874   -3.3676    0.6276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9822   -1.1157    0.7518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9997   -1.2546   -1.0607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7473   -1.3821    0.8613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5799    0.5145   -1.1771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2929    0.6753    1.4130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4561    2.3264   -0.6575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3737    3.1148    0.9942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3146    3.9472    0.5459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3089    3.2015   -1.1491 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4955    2.3683    0.6786 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1133    0.7893    2.2953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5567    2.4972    2.2135 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4349    1.3184   -1.4862 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4853   -0.8944    1.4775 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4076   -2.3615    1.2959 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6978   -2.4867   -0.7592 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0215   -1.0971   -2.6561 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1066    0.3879   -2.5280 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  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 10  4  1  0
 16 11  1  0
  9  5  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  3 22  1  0
  4 23  1  0
  5 24  1  0
  6 25  1  0
  6 26  1  0
  7 27  1  0
  7 28  1  0
  8 29  1  0
  9 30  1  0
  9 31  1  0
 10 32  1  0
 12 33  1  0
 13 34  1  0
 14 35  1  0
 15 36  1  0
 16 37  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-Aethylamino-3-phenyl-nor-camphan	HMDB
Fencamfamin	HMDB
Fencamfamina	HMDB
2-Ethylamino-3-phenylnorcamphane	HMDB
N-Ethyl-3-phenylbicyclo(2.2.1)heptan-2-amine	HMDB
Reactivan	HMDB
Fencamfamine hydrochloride	HMDB
Fencamfamine	MeSH

Chemical Formula

C₁₅H₂₁N

Average Molecular Weight

215.3339

Monoisotopic Molecular Weight

215.167399677

IUPAC Name

N-ethyl-3-phenylbicyclo[2.2.1]heptan-2-amine

Traditional Name

fencamfamine

CAS Registry Number

1209-98-9

SMILES

CCNC1C2CCC(C2)C1C1=CC=CC=C1

InChI Identifier

InChI=1S/C15H21N/c1-2-16-15-13-9-8-12(10-13)14(15)11-6-4-3-5-7-11/h3-7,12-16H,2,8-10H2,1H3

InChI Key

IKFBPFGUINLYQI-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Bicyclic monoterpenoids

Alternative Parents

Substituents

Bicyclic monoterpenoid
Aromatic monoterpenoid
Aralkylamine
Benzenoid
Monocyclic benzene moiety
Secondary amine
Secondary aliphatic amine
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Amine
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0015508)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.003 g/L	Not Available
LogP	3.20	SANGSTER (1994)

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.003 g/L	ALOGPS
logP	3.46	ALOGPS
logP	3.21	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Basic)	10.56	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	12.03 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	67.64 m³·mol⁻¹	ChemAxon
Polarizability	26.13 Å³	ChemAxon
Number of Rings	3	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]+	150.66	31661259
DarkChem	[M-H]-	147.545	31661259
DeepCCS	[M+H]+	149.644	30932474
DeepCCS	[M-H]-	147.286	30932474
DeepCCS	[M-2H]-	181.713	30932474
DeepCCS	[M+Na]+	156.94	30932474
AllCCS	[M+H]+	152.2	32859911
AllCCS	[M+H-H2O]+	148.2	32859911
AllCCS	[M+NH4]+	155.9	32859911
AllCCS	[M+Na]+	157.0	32859911
AllCCS	[M-H]-	159.5	32859911
AllCCS	[M+Na-2H]-	159.6	32859911
AllCCS	[M+HCOO]-	159.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Fencamfamine	CCNC1C2CCC(C2)C1C1=CC=CC=C1	2165.7	Standard polar	33892256
Fencamfamine	CCNC1C2CCC(C2)C1C1=CC=CC=C1	1692.6	Standard non polar	33892256
Fencamfamine	CCNC1C2CCC(C2)C1C1=CC=CC=C1	1693.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Fencamfamine,1TMS,isomer #1	CCN(C1C2CCC(C2)C1C1=CC=CC=C1)[Si](C)(C)C	1834.7	Semi standard non polar	33892256
Fencamfamine,1TMS,isomer #1	CCN(C1C2CCC(C2)C1C1=CC=CC=C1)[Si](C)(C)C	1977.2	Standard non polar	33892256
Fencamfamine,1TMS,isomer #1	CCN(C1C2CCC(C2)C1C1=CC=CC=C1)[Si](C)(C)C	2263.2	Standard polar	33892256
Fencamfamine,1TBDMS,isomer #1	CCN(C1C2CCC(C2)C1C1=CC=CC=C1)[Si](C)(C)C(C)(C)C	2074.6	Semi standard non polar	33892256
Fencamfamine,1TBDMS,isomer #1	CCN(C1C2CCC(C2)C1C1=CC=CC=C1)[Si](C)(C)C(C)(C)C	2215.6	Standard non polar	33892256
Fencamfamine,1TBDMS,isomer #1	CCN(C1C2CCC(C2)C1C1=CC=CC=C1)[Si](C)(C)C(C)(C)C	2425.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Fencamfamine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0g2j-6910000000-0272b165bf404087b355	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Fencamfamine 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 - Fencamfamine 10V, Positive-QTOF	splash10-014i-1290000000-1061401d35301018c5ad	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fencamfamine 20V, Positive-QTOF	splash10-01b9-7980000000-0349f1ea830df9893202	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fencamfamine 40V, Positive-QTOF	splash10-00nf-9300000000-35d4a9a54b631f17acab	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fencamfamine 10V, Negative-QTOF	splash10-03di-0090000000-3a3e0a649a37059d1618	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fencamfamine 20V, Negative-QTOF	splash10-03di-1290000000-8b877af7795509948959	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fencamfamine 40V, Negative-QTOF	splash10-0006-9300000000-527fa30d6841f9e3199e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fencamfamine 10V, Positive-QTOF	splash10-014i-0090000000-c482668b0d76ffc30f05	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fencamfamine 20V, Positive-QTOF	splash10-014i-3390000000-e8e234a796762242b1b1	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fencamfamine 40V, Positive-QTOF	splash10-0006-9400000000-9aabde47aadb6e14eb6e	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fencamfamine 10V, Negative-QTOF	splash10-03di-0090000000-96f048bbd45b899ef624	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fencamfamine 20V, Negative-QTOF	splash10-0229-2960000000-4efd34d61daedd5e0119	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fencamfamine 40V, Negative-QTOF	splash10-01r6-9830000000-4ba9471318e612878a1e	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01463	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01463	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01463

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

13922

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Fencamfamine

METLIN ID

Not Available

PubChem Compound

14584

PDB ID

Not Available

ChEBI ID

101009

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

DeLucia R, Planeta CS: Fencamfamine. Gen Pharmacol. 1990;21(2):161-3. [PubMed:1970543 ]
Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
South African Electronic Package Inserts [Link]

Enzymes

Enzyme Details

1. Sodium-dependent dopamine transporter

General function:: Involved in neurotransmitter:sodium symporter activity
Specific function:: Amine transporter. Terminates the action of dopamine by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name:: SLC6A3
Uniprot ID:: Q01959
Molecular weight:: 68494.255

References

Seyfried CA: Dopamine uptake inhibiting versus dopamine releasing properties of fencamfamine: an in vitro study. Biochem Pharmacol. 1983 Aug 1;32(15):2329-31. [PubMed:6136281 ]
Li SM, Campbell BL, Katz JL: Interactions of cocaine with dopamine uptake inhibitors or dopamine releasers in rats discriminating cocaine. J Pharmacol Exp Ther. 2006 Jun;317(3):1088-96. Epub 2006 Feb 14. [PubMed:16478825 ]

Showing metabocard for Fencamfamine (HMDB0015508)

MOL for HMDB0015508 (Fencamfamine)

3D MOL for HMDB0015508 (Fencamfamine)

3D SDF for HMDB0015508 (Fencamfamine)

3D-SDF for HMDB0015508 (Fencamfamine)

PDB for HMDB0015508 (Fencamfamine)

3D PDB for HMDB0015508 (Fencamfamine)

SMILES for HMDB0015508 (Fencamfamine)

INCHI for HMDB0015508 (Fencamfamine)

Structure for HMDB0015508 (Fencamfamine)

3D Structure for HMDB0015508 (Fencamfamine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References