Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (5) Show 5 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:54 UTC

HMDB ID

HMDB0015207

Secondary Accession Numbers

HMDB15207

Metabolite Identification

Common Name

Perhexiline

Description

Perhexiline is only found in individuals that have used or taken this drug. It is a coronary vasodilator used especially for angina of effort. It may cause neuropathy and hepatitis. [PubChem]Perhexiline binds to the mitochondrial enzyme carnitine palmitoyltransferase (CPT)-1 and CPT-2. It acts by shifting myocardial substrate utilisation from long chain fatty acids to carbohydrates through inhibition of CPT-1 and, to a lesser extent, CPT-2, resulting in increased glucose and lactate utilization. This results in increased ATP production for the same O2 consumption as before and consequently increases myocardial efficiency.

Structure

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

HMDB0015207
     RDKit          3D
Perhexiline
 55 57  0  0  0  0  0  0  0  0999 V2000
   -3.2380   -3.6186    0.1541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2518   -3.4693    1.2880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0941   -2.5875    0.9398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5609   -1.2514    0.3995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3125   -0.4991   -0.1676 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6554   -0.3589    0.9588 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9761    0.2771    0.7241 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7961   -0.4962   -0.3246 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9023    0.3915   -0.7874 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4365    1.1196    0.4303 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2019    0.2392    1.6370 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7927    0.1311    1.9494 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7554    0.7269   -0.8655 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1863    1.6305   -1.5366 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2145    3.0630   -0.9835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1208    3.6857   -1.2837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1814    2.7582   -0.7631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6024    1.6297    0.0660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5752   -1.4343   -0.6789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7725   -2.2792   -0.2618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8097   -4.1355   -0.7013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0825   -4.2209    0.5360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7829   -3.1516    2.2075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8466   -4.4847    1.4980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4236   -3.1251    0.2745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6280   -2.3761    1.9564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0068   -0.7160    1.2422 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1267   -1.2093   -0.8728 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9509   -1.4281    1.2579 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1643   -0.0076    1.9022 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9941    1.3182    0.3906 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1791   -1.4410    0.1094 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1111   -0.7649   -1.1287 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5771    1.0785   -1.5683 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7097   -0.2742   -1.2038 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5352    1.2878    0.3736 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8807    2.0619    0.6034 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6789   -0.7574    1.5350 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6916    0.7330    2.5029 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5181    0.8421    2.6557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5195    0.4453   -1.6654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1934    1.8479   -2.6213 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2028    1.3483   -1.7266 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9576    3.5898   -1.6487 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5473    3.1411    0.0414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1891    4.7095   -0.8656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2049    3.7944   -2.3870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8598    2.3794   -1.5577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8277    3.3533   -0.0756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9676    2.0945    0.8445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4690    1.0915    0.4887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9545   -0.4952   -1.1440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0785   -2.0233   -1.5034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2936   -1.7423    0.5291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3844   -2.4215   -1.1732 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
  9 10  1  0
 10 11  1  0
 11 12  1  0
  5 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
  4 19  1  0
 19 20  1  0
 20  1  1  0
 12  7  1  0
 18 13  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  2 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
  8 32  1  0
  8 33  1  0
  9 34  1  0
  9 35  1  0
 10 36  1  0
 10 37  1  0
 11 38  1  0
 11 39  1  0
 12 40  1  0
 13 41  1  0
 14 42  1  0
 14 43  1  0
 15 44  1  0
 15 45  1  0
 16 46  1  0
 16 47  1  0
 17 48  1  0
 17 49  1  0
 18 50  1  0
 18 51  1  0
 19 52  1  0
 19 53  1  0
 20 54  1  0
 20 55  1  0
M  END

1074
  Mrv0541 02231215132D          

 20 22  0  0  1  0            999 V2000
    5.9370   -0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 10  1  0  0  0  0
  1 19  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  2  5  1  0  0  0  0
  3  6  1  0  0  0  0
  3  7  1  0  0  0  0
  4  8  1  0  0  0  0
  4  9  1  0  0  0  0
  5 10  1  0  0  0  0
  6 11  1  0  0  0  0
  7 12  1  0  0  0  0
  8 13  1  0  0  0  0
  9 14  1  0  0  0  0
 10 17  1  0  0  0  0
 11 15  1  0  0  0  0
 12 15  1  0  0  0  0
 13 16  1  0  0  0  0
 14 16  1  0  0  0  0
 17 18  1  0  0  0  0
 18 20  1  0  0  0  0
 19 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015207

> <DATABASE_NAME>
hmdb

> <SMILES>
C(C(C1CCCCC1)C1CCCCC1)C1CCCCN1

> <INCHI_IDENTIFIER>
InChI=1S/C19H35N/c1-3-9-16(10-4-1)19(17-11-5-2-6-12-17)15-18-13-7-8-14-20-18/h16-20H,1-15H2

> <INCHI_KEY>
CYXKNKQEMFBLER-UHFFFAOYSA-N

> <FORMULA>
C19H35N

> <MOLECULAR_WEIGHT>
277.4879

> <EXACT_MASS>
277.276950125

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
36.215217448600754

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(2,2-dicyclohexylethyl)piperidine

> <ALOGPS_LOGP>
5.87

> <JCHEM_LOGP>
5.531308548333334

> <ALOGPS_LOGS>
-7.01

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
10.57935259054534

> <JCHEM_POLAR_SURFACE_AREA>
12.03

> <JCHEM_REFRACTIVITY>
87.22859999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.72e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
perhexiline

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0015207
     RDKit          3D
Perhexiline
 55 57  0  0  0  0  0  0  0  0999 V2000
   -3.2380   -3.6186    0.1541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2518   -3.4693    1.2880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0941   -2.5875    0.9398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5609   -1.2514    0.3995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3125   -0.4991   -0.1676 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6554   -0.3589    0.9588 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9761    0.2771    0.7241 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7961   -0.4962   -0.3246 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9023    0.3915   -0.7874 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4365    1.1196    0.4303 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2019    0.2392    1.6370 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7927    0.1311    1.9494 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7554    0.7269   -0.8655 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1863    1.6305   -1.5366 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2145    3.0630   -0.9835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1208    3.6857   -1.2837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1814    2.7582   -0.7631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6024    1.6297    0.0660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5752   -1.4343   -0.6789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7725   -2.2792   -0.2618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8097   -4.1355   -0.7013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0825   -4.2209    0.5360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7829   -3.1516    2.2075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8466   -4.4847    1.4980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4236   -3.1251    0.2745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6280   -2.3761    1.9564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0068   -0.7160    1.2422 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1267   -1.2093   -0.8728 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9509   -1.4281    1.2579 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1643   -0.0076    1.9022 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9941    1.3182    0.3906 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1791   -1.4410    0.1094 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1111   -0.7649   -1.1287 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5771    1.0785   -1.5683 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7097   -0.2742   -1.2038 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5352    1.2878    0.3736 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8807    2.0619    0.6034 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6789   -0.7574    1.5350 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6916    0.7330    2.5029 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5181    0.8421    2.6557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5195    0.4453   -1.6654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1934    1.8479   -2.6213 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2028    1.3483   -1.7266 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9576    3.5898   -1.6487 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5473    3.1411    0.0414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1891    4.7095   -0.8656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2049    3.7944   -2.3870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8598    2.3794   -1.5577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8277    3.3533   -0.0756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9676    2.0945    0.8445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4690    1.0915    0.4887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9545   -0.4952   -1.1440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0785   -2.0233   -1.5034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2936   -1.7423    0.5291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3844   -2.4215   -1.1732 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
  9 10  1  0
 10 11  1  0
 11 12  1  0
  5 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
  4 19  1  0
 19 20  1  0
 20  1  1  0
 12  7  1  0
 18 13  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  2 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
  8 32  1  0
  8 33  1  0
  9 34  1  0
  9 35  1  0
 10 36  1  0
 10 37  1  0
 11 38  1  0
 11 39  1  0
 12 40  1  0
 13 41  1  0
 14 42  1  0
 14 43  1  0
 15 44  1  0
 15 45  1  0
 16 46  1  0
 16 47  1  0
 17 48  1  0
 17 49  1  0
 18 50  1  0
 18 51  1  0
 19 52  1  0
 19 53  1  0
 20 54  1  0
 20 55  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1074                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  N   UNK     0      11.082  -1.540   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       7.081  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.748  -1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.081   0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.415  -1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.748  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.414  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.415   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.748   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.748  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.414  -3.850   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.080  -1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.415   3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.748   3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.080  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.081   3.850   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.748   0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.082   1.540   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.416  -0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.416   0.770   0.000  0.00  0.00           C+0
CONECT    1   10   19                                                       
CONECT    2    3    4    5                                                  
CONECT    3    2    6    7                                                  
CONECT    4    2    8    9                                                  
CONECT    5    2   10                                                       
CONECT    6    3   11                                                       
CONECT    7    3   12                                                       
CONECT    8    4   13                                                       
CONECT    9    4   14                                                       
CONECT   10    1    5   17                                                  
CONECT   11    6   15                                                       
CONECT   12    7   15                                                       
CONECT   13    8   16                                                       
CONECT   14    9   16                                                       
CONECT   15   11   12                                                       
CONECT   16   13   14                                                       
CONECT   17   10   18                                                       
CONECT   18   17   20                                                       
CONECT   19    1   20                                                       
CONECT   20   18   19                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

COMPND    HMDB0015207
HETATM    1  C1  UNL     1      -3.238  -3.619   0.154  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.252  -3.469   1.288  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.094  -2.587   0.940  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.561  -1.251   0.400  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.312  -0.499  -0.168  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.655  -0.359   0.959  1.00  0.00           C  
HETATM    7  C7  UNL     1       1.976   0.277   0.724  1.00  0.00           C  
HETATM    8  C8  UNL     1       2.796  -0.496  -0.325  1.00  0.00           C  
HETATM    9  C9  UNL     1       3.902   0.392  -0.787  1.00  0.00           C  
HETATM   10  C10 UNL     1       4.437   1.120   0.430  1.00  0.00           C  
HETATM   11  C11 UNL     1       4.202   0.239   1.637  1.00  0.00           C  
HETATM   12  N1  UNL     1       2.793   0.131   1.949  1.00  0.00           N  
HETATM   13  C12 UNL     1      -0.755   0.727  -0.865  1.00  0.00           C  
HETATM   14  C13 UNL     1       0.186   1.631  -1.537  1.00  0.00           C  
HETATM   15  C14 UNL     1       0.215   3.063  -0.983  1.00  0.00           C  
HETATM   16  C15 UNL     1      -1.121   3.686  -1.284  1.00  0.00           C  
HETATM   17  C16 UNL     1      -2.181   2.758  -0.763  1.00  0.00           C  
HETATM   18  C17 UNL     1      -1.602   1.630   0.066  1.00  0.00           C  
HETATM   19  C18 UNL     1      -2.575  -1.434  -0.679  1.00  0.00           C  
HETATM   20  C19 UNL     1      -3.773  -2.279  -0.262  1.00  0.00           C  
HETATM   21  H1  UNL     1      -2.810  -4.135  -0.701  1.00  0.00           H  
HETATM   22  H2  UNL     1      -4.083  -4.221   0.536  1.00  0.00           H  
HETATM   23  H3  UNL     1      -2.783  -3.152   2.208  1.00  0.00           H  
HETATM   24  H4  UNL     1      -1.847  -4.485   1.498  1.00  0.00           H  
HETATM   25  H5  UNL     1      -0.424  -3.125   0.275  1.00  0.00           H  
HETATM   26  H6  UNL     1      -0.628  -2.376   1.956  1.00  0.00           H  
HETATM   27  H7  UNL     1      -2.007  -0.716   1.242  1.00  0.00           H  
HETATM   28  H8  UNL     1       0.127  -1.209  -0.873  1.00  0.00           H  
HETATM   29  H9  UNL     1       0.951  -1.428   1.258  1.00  0.00           H  
HETATM   30  H10 UNL     1       0.164  -0.008   1.902  1.00  0.00           H  
HETATM   31  H11 UNL     1       1.994   1.318   0.391  1.00  0.00           H  
HETATM   32  H12 UNL     1       3.179  -1.441   0.109  1.00  0.00           H  
HETATM   33  H13 UNL     1       2.111  -0.765  -1.129  1.00  0.00           H  
HETATM   34  H14 UNL     1       3.577   1.079  -1.568  1.00  0.00           H  
HETATM   35  H15 UNL     1       4.710  -0.274  -1.204  1.00  0.00           H  
HETATM   36  H16 UNL     1       5.535   1.288   0.374  1.00  0.00           H  
HETATM   37  H17 UNL     1       3.881   2.062   0.603  1.00  0.00           H  
HETATM   38  H18 UNL     1       4.679  -0.757   1.535  1.00  0.00           H  
HETATM   39  H19 UNL     1       4.692   0.733   2.503  1.00  0.00           H  
HETATM   40  H20 UNL     1       2.518   0.842   2.656  1.00  0.00           H  
HETATM   41  H21 UNL     1      -1.519   0.445  -1.665  1.00  0.00           H  
HETATM   42  H22 UNL     1      -0.193   1.848  -2.621  1.00  0.00           H  
HETATM   43  H23 UNL     1       1.203   1.348  -1.727  1.00  0.00           H  
HETATM   44  H24 UNL     1       0.958   3.590  -1.649  1.00  0.00           H  
HETATM   45  H25 UNL     1       0.547   3.141   0.041  1.00  0.00           H  
HETATM   46  H26 UNL     1      -1.189   4.710  -0.866  1.00  0.00           H  
HETATM   47  H27 UNL     1      -1.205   3.794  -2.387  1.00  0.00           H  
HETATM   48  H28 UNL     1      -2.860   2.379  -1.558  1.00  0.00           H  
HETATM   49  H29 UNL     1      -2.828   3.353  -0.076  1.00  0.00           H  
HETATM   50  H30 UNL     1      -0.968   2.095   0.844  1.00  0.00           H  
HETATM   51  H31 UNL     1      -2.469   1.091   0.489  1.00  0.00           H  
HETATM   52  H32 UNL     1      -2.955  -0.495  -1.144  1.00  0.00           H  
HETATM   53  H33 UNL     1      -2.078  -2.023  -1.503  1.00  0.00           H  
HETATM   54  H34 UNL     1      -4.294  -1.742   0.529  1.00  0.00           H  
HETATM   55  H35 UNL     1      -4.384  -2.422  -1.173  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3   23   24
CONECT    3    4   25   26
CONECT    4    5   19   27
CONECT    5    6   13   28
CONECT    6    7   29   30
CONECT    7    8   12   31
CONECT    8    9   32   33
CONECT    9   10   34   35
CONECT   10   11   36   37
CONECT   11   12   38   39
CONECT   12   40
CONECT   13   14   18   41
CONECT   14   15   42   43
CONECT   15   16   44   45
CONECT   16   17   46   47
CONECT   17   18   48   49
CONECT   18   50   51
CONECT   19   20   52   53
CONECT   20   54   55
END

HMDB0015207
     RDKit          3D
Perhexiline
 55 57  0  0  0  0  0  0  0  0999 V2000
   -3.2380   -3.6186    0.1541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2518   -3.4693    1.2880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0941   -2.5875    0.9398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5609   -1.2514    0.3995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3125   -0.4991   -0.1676 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6554   -0.3589    0.9588 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9761    0.2771    0.7241 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7961   -0.4962   -0.3246 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9023    0.3915   -0.7874 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4365    1.1196    0.4303 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2019    0.2392    1.6370 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7927    0.1311    1.9494 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7554    0.7269   -0.8655 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1863    1.6305   -1.5366 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2145    3.0630   -0.9835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1208    3.6857   -1.2837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1814    2.7582   -0.7631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6024    1.6297    0.0660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5752   -1.4343   -0.6789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7725   -2.2792   -0.2618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8097   -4.1355   -0.7013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0825   -4.2209    0.5360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7829   -3.1516    2.2075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8466   -4.4847    1.4980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4236   -3.1251    0.2745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6280   -2.3761    1.9564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0068   -0.7160    1.2422 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1267   -1.2093   -0.8728 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9509   -1.4281    1.2579 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1643   -0.0076    1.9022 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9941    1.3182    0.3906 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1791   -1.4410    0.1094 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1111   -0.7649   -1.1287 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5771    1.0785   -1.5683 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7097   -0.2742   -1.2038 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5352    1.2878    0.3736 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8807    2.0619    0.6034 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6789   -0.7574    1.5350 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6916    0.7330    2.5029 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5181    0.8421    2.6557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5195    0.4453   -1.6654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1934    1.8479   -2.6213 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2028    1.3483   -1.7266 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9576    3.5898   -1.6487 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5473    3.1411    0.0414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1891    4.7095   -0.8656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2049    3.7944   -2.3870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8598    2.3794   -1.5577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8277    3.3533   -0.0756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9676    2.0945    0.8445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4690    1.0915    0.4887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9545   -0.4952   -1.1440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0785   -2.0233   -1.5034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2936   -1.7423    0.5291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3844   -2.4215   -1.1732 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
  9 10  1  0
 10 11  1  0
 11 12  1  0
  5 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
  4 19  1  0
 19 20  1  0
 20  1  1  0
 12  7  1  0
 18 13  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  2 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
  8 32  1  0
  8 33  1  0
  9 34  1  0
  9 35  1  0
 10 36  1  0
 10 37  1  0
 11 38  1  0
 11 39  1  0
 12 40  1  0
 13 41  1  0
 14 42  1  0
 14 43  1  0
 15 44  1  0
 15 45  1  0
 16 46  1  0
 16 47  1  0
 17 48  1  0
 17 49  1  0
 18 50  1  0
 18 51  1  0
 19 52  1  0
 19 53  1  0
 20 54  1  0
 20 55  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Perhexilene	ChEBI
(+)-2-(2,2-Dicyclohexylethyl)piperidine	HMDB
(-)-2-(2,2-Dicyclohexylethyl)piperidine	HMDB
2-(2,2-Dicyclohexylethyl)piperidine	HMDB
Perhexilline	HMDB

Chemical Formula

C₁₉H₃₅N

Average Molecular Weight

277.4879

Monoisotopic Molecular Weight

277.276950125

IUPAC Name

2-(2,2-dicyclohexylethyl)piperidine

Traditional Name

perhexiline

CAS Registry Number

6621-47-2

SMILES

C(C(C1CCCCC1)C1CCCCC1)C1CCCCN1

InChI Identifier

InChI=1S/C19H35N/c1-3-9-16(10-4-1)19(17-11-5-2-6-12-17)15-18-13-7-8-14-20-18/h16-20H,1-15H2

InChI Key

CYXKNKQEMFBLER-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as piperidines. Piperidines are compounds containing a piperidine ring, which is a saturated aliphatic six-member ring with one nitrogen atom and five carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Piperidines

Sub Class

Not Available

Direct Parent

Piperidines

Alternative Parents

Substituents

Piperidine
Azacycle
Secondary amine
Secondary aliphatic amine
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Amine
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

piperidines (CHEBI:35553 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0015207)
Membrane (HMDB: HMDB0015207)

Source

Exogenous

Exogenous (HMDB: HMDB0015207)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Cardiovascular drug (HMDB: HMDB0015207)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	2.7e-05 g/L	Not Available
LogP	6.2	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	179.849	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001066

Predicted Molecular Properties

Property	Value	Source
Water Solubility	2.7e-05 g/L	ALOGPS
logP	5.87	ALOGPS
logP	5.53	ChemAxon
logS	-7	ALOGPS
pKa (Strongest Basic)	10.58	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	4	ChemAxon
Refractivity	87.23 m³·mol⁻¹	ChemAxon
Polarizability	36.22 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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]+	166.631	31661259
DarkChem	[M-H]-	164.651	31661259
DeepCCS	[M+H]+	168.033	30932474
DeepCCS	[M-H]-	165.675	30932474
DeepCCS	[M-2H]-	198.671	30932474
DeepCCS	[M+Na]+	174.127	30932474
AllCCS	[M+H]+	175.3	32859911
AllCCS	[M+H-H2O]+	172.1	32859911
AllCCS	[M+NH4]+	178.4	32859911
AllCCS	[M+Na]+	179.2	32859911
AllCCS	[M-H]-	180.9	32859911
AllCCS	[M+Na-2H]-	181.2	32859911
AllCCS	[M+HCOO]-	181.7	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.	6.4 minutes	32390414
Predicted by Siyang on May 30, 2022	16.859 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.35 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	43.4 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2265.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	371.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	216.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	194.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	466.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	630.4 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	555.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	310.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1528.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	497.5 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	1464.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	426.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	396.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	349.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	281.0 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	14.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Perhexiline	C(C(C1CCCCC1)C1CCCCC1)C1CCCCN1	1927.1	Standard polar	33892256
Perhexiline	C(C(C1CCCCC1)C1CCCCC1)C1CCCCN1	2166.5	Standard non polar	33892256
Perhexiline	C(C(C1CCCCC1)C1CCCCC1)C1CCCCN1	2182.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Perhexiline,1TMS,isomer #1	C[Si](C)(C)N1CCCCC1CC(C1CCCCC1)C1CCCCC1	2276.1	Semi standard non polar	33892256
Perhexiline,1TMS,isomer #1	C[Si](C)(C)N1CCCCC1CC(C1CCCCC1)C1CCCCC1	2365.8	Standard non polar	33892256
Perhexiline,1TMS,isomer #1	C[Si](C)(C)N1CCCCC1CC(C1CCCCC1)C1CCCCC1	2759.4	Standard polar	33892256
Perhexiline,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1CCCCC1CC(C1CCCCC1)C1CCCCC1	2536.5	Semi standard non polar	33892256
Perhexiline,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1CCCCC1CC(C1CCCCC1)C1CCCCC1	2549.6	Standard non polar	33892256
Perhexiline,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1CCCCC1CC(C1CCCCC1)C1CCCCC1	2914.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Perhexiline GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-9240000000-7d469dd2b3d8bdb97f5c	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Perhexiline GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Perhexiline GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-001i-9000000000-e8335ba9964dd32ada29	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Perhexiline 10V, Positive-QTOF	splash10-004i-1090000000-f6b8ccc29365a1b9553f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Perhexiline 20V, Positive-QTOF	splash10-057i-4190000000-e00b24bda85621e90894	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Perhexiline 40V, Positive-QTOF	splash10-052f-5290000000-6389e823b74d83649abe	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Perhexiline 10V, Negative-QTOF	splash10-004i-0090000000-956a531f36ba4bf82719	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Perhexiline 20V, Negative-QTOF	splash10-004i-0090000000-6374e56bfc2eb8609794	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Perhexiline 40V, Negative-QTOF	splash10-001i-9170000000-3d144881a6a7aec9d111	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Perhexiline 10V, Positive-QTOF	splash10-004i-0090000000-745fd042a988e5d1440b	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Perhexiline 20V, Positive-QTOF	splash10-004i-2190000000-9d556eceea83c2bc4021	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Perhexiline 40V, Positive-QTOF	splash10-000t-9200000000-2793cdd7988a27b7095e	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Perhexiline 10V, Negative-QTOF	splash10-004i-0090000000-f4712ee2d57b7f19751d	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Perhexiline 20V, Negative-QTOF	splash10-004i-0090000000-4b2ad669814aa4255d88	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Perhexiline 40V, Negative-QTOF	splash10-00di-0090000000-8d81ed304a7cf5c905ea	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
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 DB01074	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01074	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

DB01074

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4584

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Perhexiline

METLIN ID

Not Available

PubChem Compound

4746

PDB ID

Not Available

ChEBI ID

35553

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

Enzymes

Enzyme Details

1. Carnitine O-palmitoyltransferase 1, liver isoform

General function:: Involved in acyltransferase activity
Specific function:: Catalyzes the transfer of the acyl group of long-chain fatty acid-CoA conjugates onto carnitine, an essential step for the mitochondrial uptake of long-chain fatty acids and their subsequent beta-oxidation in the mitochondrion. Plays an important role in triglyceride metabolism.
Gene Name:: CPT1A
Uniprot ID:: P50416
Molecular weight:: 86238.415

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Kennedy JA, Kiosoglous AJ, Murphy GA, Pelle MA, Horowitz JD: Effect of perhexiline and oxfenicine on myocardial function and metabolism during low-flow ischemia/reperfusion in the isolated rat heart. J Cardiovasc Pharmacol. 2000 Dec;36(6):794-801. [PubMed:11117381 ]
Unger SA, Kennedy JA, McFadden-Lewis K, Minerds K, Murphy GA, Horowitz JD: Dissociation between metabolic and efficiency effects of perhexiline in normoxic rat myocardium. J Cardiovasc Pharmacol. 2005 Dec;46(6):849-55. [PubMed:16306812 ]
Kennedy JA, Unger SA, Horowitz JD: Inhibition of carnitine palmitoyltransferase-1 in rat heart and liver by perhexiline and amiodarone. Biochem Pharmacol. 1996 Jul 26;52(2):273-80. [PubMed:8694852 ]
Ashrafian H, Horowitz JD, Frenneaux MP: Perhexiline. Cardiovasc Drug Rev. 2007 Spring;25(1):76-97. [PubMed:17445089 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzyme Details

2. Carnitine O-palmitoyltransferase 2, mitochondrial

General function:: Involved in acyltransferase activity
Specific function:: Not Available
Gene Name:: CPT2
Uniprot ID:: P23786
Molecular weight:: 73776.335

References

Kennedy JA, Kiosoglous AJ, Murphy GA, Pelle MA, Horowitz JD: Effect of perhexiline and oxfenicine on myocardial function and metabolism during low-flow ischemia/reperfusion in the isolated rat heart. J Cardiovasc Pharmacol. 2000 Dec;36(6):794-801. [PubMed:11117381 ]
Unger SA, Kennedy JA, McFadden-Lewis K, Minerds K, Murphy GA, Horowitz JD: Dissociation between metabolic and efficiency effects of perhexiline in normoxic rat myocardium. J Cardiovasc Pharmacol. 2005 Dec;46(6):849-55. [PubMed:16306812 ]
Kennedy JA, Unger SA, Horowitz JD: Inhibition of carnitine palmitoyltransferase-1 in rat heart and liver by perhexiline and amiodarone. Biochem Pharmacol. 1996 Jul 26;52(2):273-80. [PubMed:8694852 ]

Enzyme Details

3. Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

4. Cytochrome P450 2D6

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:: CYP2D6
Uniprot ID:: P10635
Molecular weight:: 55768.94

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

5. Cytochrome P450 2B6

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,4-cineole 2-exo-monooxygenase.
Gene Name:: CYP2B6
Uniprot ID:: P20813
Molecular weight:: 56277.81

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Showing metabocard for Perhexiline (HMDB0015207)

MOL for HMDB0015207 (Perhexiline)

3D MOL for HMDB0015207 (Perhexiline)

3D SDF for HMDB0015207 (Perhexiline)

3D-SDF for HMDB0015207 (Perhexiline)

PDB for HMDB0015207 (Perhexiline)

3D PDB for HMDB0015207 (Perhexiline)

SMILES for HMDB0015207 (Perhexiline)

INCHI for HMDB0015207 (Perhexiline)

Structure for HMDB0015207 (Perhexiline)

3D Structure for HMDB0015207 (Perhexiline)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

References

References