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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 16:42:20 UTC

Update Date

2021-09-26 23:11:56 UTC

HMDB ID

HMDB0256346

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Perlapine

Description

10-(4-methylpiperazin-1-yl)-9-azatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,9,11,13-heptaene, also known as hypnodin, belongs to the class of organic compounds known as benzazepines. These are organic compounds containing a benzene ring fused to an azepine ring (unsaturated seven-membered heterocycle with one nitrogen atom replacing a carbon atom). Based on a literature review very few articles have been published on 10-(4-methylpiperazin-1-yl)-9-azatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,9,11,13-heptaene. This compound has been identified in human blood as reported by (PMID: 31557052 ). Perlapine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Perlapine is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0256346
     RDKit          3D
Perlapine
 43 46  0  0  0  0  0  0  0  0999 V2000
    4.5846   -0.6574    0.1912 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0330    0.5924   -0.2317 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3645    0.5565   -1.4942 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9849   -0.0926   -1.3670 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2559    0.6070   -0.3536 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1238    0.3824   -0.1794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9411    1.3576   -0.5031 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3523    1.4031   -0.4311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7862    2.7041   -0.3780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1335    2.9358   -0.3056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0099    1.8985   -0.2874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5850    0.5808   -0.3404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2163    0.3368   -0.4142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9548   -1.0998   -0.4627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7355   -1.5355    0.2131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8854   -2.7736    0.7961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8762   -3.4038    1.4950 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3396   -2.7640    1.6153 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5270   -1.5193    1.0428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5149   -0.9188    0.3471 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9225    1.5492    0.4965 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3310    1.2139    0.8407 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4716   -0.8252    1.2949 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6917   -0.7329   -0.0069 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1350   -1.5360   -0.3166 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2987    1.5608   -1.9505 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9443   -0.0729   -2.1790 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5241   -0.0193   -2.3727 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1609   -1.1520   -1.1745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0617    3.5029   -0.3945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4603    3.9661   -0.2643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0708    2.0603   -0.2308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2828   -0.2202   -0.3253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9826   -1.4244   -1.5227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8252   -1.6217    0.0215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8328   -3.3193    0.7266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0483   -4.3954    1.9425 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1594   -3.2200    2.1543 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4609   -0.9788    1.1106 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3628    1.7648    1.4307 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9576    2.5210   -0.0797 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8485    2.1780    1.1040 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3208    0.6112    1.7760 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  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
  5 21  1  0
 21 22  1  0
 22  2  1  0
 20  6  1  0
 13  8  1  0
 20 15  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  9 30  1  0
 10 31  1  0
 11 32  1  0
 12 33  1  0
 14 34  1  0
 14 35  1  0
 16 36  1  0
 17 37  1  0
 18 38  1  0
 19 39  1  0
 21 40  1  0
 21 41  1  0
 22 42  1  0
 22 43  1  0
M  END


  Mrv1572004221606172D          

 22 25  0  0  0  0            999 V2000
    3.2530    5.8201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5451    1.0796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7277    1.0796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7287    1.8840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9113    1.8840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7568    0.8365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0606    0.8365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1239    2.4451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3065    2.4451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0724    5.0152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3598    4.3952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7144    4.2719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0018    3.6519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4087    1.0397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1520    1.3976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6654    1.3976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3356    2.2019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4818    2.2019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8212    2.8469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9962    2.8469    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8950    5.0768    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1791    3.5902    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  4  2  2  0  0  0  0
  5  3  2  0  0  0  0
  6  2  1  0  0  0  0
  7  3  1  0  0  0  0
  8  4  1  0  0  0  0
  9  5  1  0  0  0  0
 12 10  1  0  0  0  0
 13 11  1  0  0  0  0
 15  6  2  0  0  0  0
 15 14  1  0  0  0  0
 16  7  2  0  0  0  0
 16 14  1  0  0  0  0
 17  8  2  0  0  0  0
 17 15  1  0  0  0  0
 18  9  2  0  0  0  0
 18 16  1  0  0  0  0
 19 17  1  0  0  0  0
 20 18  1  0  0  0  0
 20 19  2  0  0  0  0
 21  1  1  0  0  0  0
 21 10  1  0  0  0  0
 21 11  1  0  0  0  0
 22 12  1  0  0  0  0
 22 13  1  0  0  0  0
 22 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0256346

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1CCN(CC1)C1=NC2=CC=CC=C2CC2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C19H21N3/c1-21-10-12-22(13-11-21)19-17-8-4-2-6-15(17)14-16-7-3-5-9-18(16)20-19/h2-9H,10-14H2,1H3

> <INCHI_KEY>
PWRPUAKXMQAFCJ-UHFFFAOYSA-N

> <FORMULA>
C19H21N3

> <MOLECULAR_WEIGHT>
291.398

> <EXACT_MASS>
291.173547688

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
33.4298967003692

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
10-(4-methylpiperazin-1-yl)-9-azatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,9,11,13-heptaene

> <ALOGPS_LOGP>
2.97

> <JCHEM_LOGP>
3.4480645996666666

> <ALOGPS_LOGS>
-3.44

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
7.377207453210181

> <JCHEM_POLAR_SURFACE_AREA>
18.84

> <JCHEM_REFRACTIVITY>
93.80269999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.07e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
perlapine

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0256346
     RDKit          3D
Perlapine
 43 46  0  0  0  0  0  0  0  0999 V2000
    4.5846   -0.6574    0.1912 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0330    0.5924   -0.2317 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3645    0.5565   -1.4942 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9849   -0.0926   -1.3670 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2559    0.6070   -0.3536 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1238    0.3824   -0.1794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9411    1.3576   -0.5031 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3523    1.4031   -0.4311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7862    2.7041   -0.3780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1335    2.9358   -0.3056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0099    1.8985   -0.2874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5850    0.5808   -0.3404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2163    0.3368   -0.4142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9548   -1.0998   -0.4627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7355   -1.5355    0.2131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8854   -2.7736    0.7961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8762   -3.4038    1.4950 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3396   -2.7640    1.6153 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5270   -1.5193    1.0428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5149   -0.9188    0.3471 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9225    1.5492    0.4965 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3310    1.2139    0.8407 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4716   -0.8252    1.2949 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6917   -0.7329   -0.0069 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1350   -1.5360   -0.3166 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2987    1.5608   -1.9505 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9443   -0.0729   -2.1790 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5241   -0.0193   -2.3727 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1609   -1.1520   -1.1745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0617    3.5029   -0.3945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4603    3.9661   -0.2643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0708    2.0603   -0.2308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2828   -0.2202   -0.3253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9826   -1.4244   -1.5227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8252   -1.6217    0.0215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8328   -3.3193    0.7266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0483   -4.3954    1.9425 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1594   -3.2200    2.1543 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4609   -0.9788    1.1106 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3628    1.7648    1.4307 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9576    2.5210   -0.0797 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8485    2.1780    1.1040 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3208    0.6112    1.7760 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  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
  5 21  1  0
 21 22  1  0
 22  2  1  0
 20  6  1  0
 13  8  1  0
 20 15  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  9 30  1  0
 10 31  1  0
 11 32  1  0
 12 33  1  0
 14 34  1  0
 14 35  1  0
 16 36  1  0
 17 37  1  0
 18 38  1  0
 19 39  1  0
 21 40  1  0
 21 41  1  0
 22 42  1  0
 22 43  1  0
M  END

HEADER    PROTEIN                                 22-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-APR-16         0                                  
HETATM    1  C   UNK     0       6.072  10.864   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.618   2.015   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.358   2.015   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.960   3.517   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.701   3.517   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.146   1.561   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.113   1.561   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.831   4.564   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.572   4.564   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.868   9.362   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.272   8.204   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.200   7.974   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.603   6.817   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.630   1.941   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.017   2.609   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.242   2.609   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.360   4.110   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.899   4.110   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.400   5.314   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0       1.860   5.314   0.000  0.00  0.00           N+0
HETATM   21  N   UNK     0       5.404   9.477   0.000  0.00  0.00           N+0
HETATM   22  N   UNK     0       4.068   6.702   0.000  0.00  0.00           N+0
CONECT    1   21                                                            
CONECT    2    4    6                                                       
CONECT    3    5    7                                                       
CONECT    4    2    8                                                       
CONECT    5    3    9                                                       
CONECT    6    2   15                                                       
CONECT    7    3   16                                                       
CONECT    8    4   17                                                       
CONECT    9    5   18                                                       
CONECT   10   12   21                                                       
CONECT   11   13   21                                                       
CONECT   12   10   22                                                       
CONECT   13   11   22                                                       
CONECT   14   15   16                                                       
CONECT   15    6   14   17                                                  
CONECT   16    7   14   18                                                  
CONECT   17    8   15   19                                                  
CONECT   18    9   16   20                                                  
CONECT   19   17   20   22                                                  
CONECT   20   18   19                                                       
CONECT   21    1   10   11                                                  
CONECT   22   12   13   19                                                  
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

COMPND    HMDB0256346
HETATM    1  C1  UNL     1       4.585  -0.657   0.191  1.00  0.00           C  
HETATM    2  N1  UNL     1       4.033   0.592  -0.232  1.00  0.00           N  
HETATM    3  C2  UNL     1       3.364   0.557  -1.494  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.985  -0.093  -1.367  1.00  0.00           C  
HETATM    5  N2  UNL     1       1.256   0.607  -0.354  1.00  0.00           N  
HETATM    6  C4  UNL     1      -0.124   0.382  -0.179  1.00  0.00           C  
HETATM    7  N3  UNL     1      -0.941   1.358  -0.503  1.00  0.00           N  
HETATM    8  C5  UNL     1      -2.352   1.403  -0.431  1.00  0.00           C  
HETATM    9  C6  UNL     1      -2.786   2.704  -0.378  1.00  0.00           C  
HETATM   10  C7  UNL     1      -4.133   2.936  -0.306  1.00  0.00           C  
HETATM   11  C8  UNL     1      -5.010   1.899  -0.287  1.00  0.00           C  
HETATM   12  C9  UNL     1      -4.585   0.581  -0.340  1.00  0.00           C  
HETATM   13  C10 UNL     1      -3.216   0.337  -0.414  1.00  0.00           C  
HETATM   14  C11 UNL     1      -2.955  -1.100  -0.463  1.00  0.00           C  
HETATM   15  C12 UNL     1      -1.735  -1.536   0.213  1.00  0.00           C  
HETATM   16  C13 UNL     1      -1.885  -2.774   0.796  1.00  0.00           C  
HETATM   17  C14 UNL     1      -0.876  -3.404   1.495  1.00  0.00           C  
HETATM   18  C15 UNL     1       0.340  -2.764   1.615  1.00  0.00           C  
HETATM   19  C16 UNL     1       0.527  -1.519   1.043  1.00  0.00           C  
HETATM   20  C17 UNL     1      -0.515  -0.919   0.347  1.00  0.00           C  
HETATM   21  C18 UNL     1       1.923   1.549   0.497  1.00  0.00           C  
HETATM   22  C19 UNL     1       3.331   1.214   0.841  1.00  0.00           C  
HETATM   23  H1  UNL     1       4.472  -0.825   1.295  1.00  0.00           H  
HETATM   24  H2  UNL     1       5.692  -0.733  -0.007  1.00  0.00           H  
HETATM   25  H3  UNL     1       4.135  -1.536  -0.317  1.00  0.00           H  
HETATM   26  H4  UNL     1       3.299   1.561  -1.950  1.00  0.00           H  
HETATM   27  H5  UNL     1       3.944  -0.073  -2.179  1.00  0.00           H  
HETATM   28  H6  UNL     1       1.524  -0.019  -2.373  1.00  0.00           H  
HETATM   29  H7  UNL     1       2.161  -1.152  -1.174  1.00  0.00           H  
HETATM   30  H8  UNL     1      -2.062   3.503  -0.394  1.00  0.00           H  
HETATM   31  H9  UNL     1      -4.460   3.966  -0.264  1.00  0.00           H  
HETATM   32  H10 UNL     1      -6.071   2.060  -0.231  1.00  0.00           H  
HETATM   33  H11 UNL     1      -5.283  -0.220  -0.325  1.00  0.00           H  
HETATM   34  H12 UNL     1      -2.983  -1.424  -1.523  1.00  0.00           H  
HETATM   35  H13 UNL     1      -3.825  -1.622   0.021  1.00  0.00           H  
HETATM   36  H14 UNL     1      -2.833  -3.319   0.727  1.00  0.00           H  
HETATM   37  H15 UNL     1      -1.048  -4.395   1.943  1.00  0.00           H  
HETATM   38  H16 UNL     1       1.159  -3.220   2.154  1.00  0.00           H  
HETATM   39  H17 UNL     1       1.461  -0.979   1.111  1.00  0.00           H  
HETATM   40  H18 UNL     1       1.363   1.765   1.431  1.00  0.00           H  
HETATM   41  H19 UNL     1       1.958   2.521  -0.080  1.00  0.00           H  
HETATM   42  H20 UNL     1       3.849   2.178   1.104  1.00  0.00           H  
HETATM   43  H21 UNL     1       3.321   0.611   1.776  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3   22
CONECT    3    4   26   27
CONECT    4    5   28   29
CONECT    5    6   21
CONECT    6    7    7   20
CONECT    7    8
CONECT    8    9    9   13
CONECT    9   10   30
CONECT   10   11   11   31
CONECT   11   12   32
CONECT   12   13   13   33
CONECT   13   14
CONECT   14   15   34   35
CONECT   15   16   16   20
CONECT   16   17   36
CONECT   17   18   18   37
CONECT   18   19   38
CONECT   19   20   20   39
CONECT   21   22   40   41
CONECT   22   42   43
END

HMDB0256346
     RDKit          3D
Perlapine
 43 46  0  0  0  0  0  0  0  0999 V2000
    4.5846   -0.6574    0.1912 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0330    0.5924   -0.2317 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3645    0.5565   -1.4942 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9849   -0.0926   -1.3670 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2559    0.6070   -0.3536 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1238    0.3824   -0.1794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9411    1.3576   -0.5031 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3523    1.4031   -0.4311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7862    2.7041   -0.3780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1335    2.9358   -0.3056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0099    1.8985   -0.2874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5850    0.5808   -0.3404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2163    0.3368   -0.4142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9548   -1.0998   -0.4627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7355   -1.5355    0.2131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8854   -2.7736    0.7961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8762   -3.4038    1.4950 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3396   -2.7640    1.6153 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5270   -1.5193    1.0428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5149   -0.9188    0.3471 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9225    1.5492    0.4965 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3310    1.2139    0.8407 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4716   -0.8252    1.2949 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6917   -0.7329   -0.0069 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1350   -1.5360   -0.3166 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2987    1.5608   -1.9505 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9443   -0.0729   -2.1790 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5241   -0.0193   -2.3727 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1609   -1.1520   -1.1745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0617    3.5029   -0.3945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4603    3.9661   -0.2643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0708    2.0603   -0.2308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2828   -0.2202   -0.3253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9826   -1.4244   -1.5227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8252   -1.6217    0.0215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8328   -3.3193    0.7266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0483   -4.3954    1.9425 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1594   -3.2200    2.1543 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4609   -0.9788    1.1106 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3628    1.7648    1.4307 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9576    2.5210   -0.0797 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8485    2.1780    1.1040 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3208    0.6112    1.7760 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  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
  5 21  1  0
 21 22  1  0
 22  2  1  0
 20  6  1  0
 13  8  1  0
 20 15  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  9 30  1  0
 10 31  1  0
 11 32  1  0
 12 33  1  0
 14 34  1  0
 14 35  1  0
 16 36  1  0
 17 37  1  0
 18 38  1  0
 19 39  1  0
 21 40  1  0
 21 41  1  0
 22 42  1  0
 22 43  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Hypnodin	Kegg
Perlapine	MeSH
6-(4-Methylpiperazin-1-yl)-11H-dibenzazepine	MeSH
Perlapine monohydrochloride	MeSH
6-(4-Methyl-1-piperazinyl)morphanthridine	MeSH

Chemical Formula

C₁₉H₂₁N₃

Average Molecular Weight

291.398

Monoisotopic Molecular Weight

291.173547688

IUPAC Name

10-(4-methylpiperazin-1-yl)-9-azatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,9,11,13-heptaene

Traditional Name

perlapine

CAS Registry Number

Not Available

SMILES

CN1CCN(CC1)C1=NC2=CC=CC=C2CC2=CC=CC=C12

InChI Identifier

InChI=1S/C19H21N3/c1-21-10-12-22(13-11-21)19-17-8-4-2-6-15(17)14-16-7-3-5-9-18(16)20-19/h2-9H,10-14H2,1H3

InChI Key

PWRPUAKXMQAFCJ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzazepines. These are organic compounds containing a benzene ring fused to an azepine ring (unsaturated seven-membered heterocycle with one nitrogen atom replacing a carbon atom).

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzazepines

Sub Class

Not Available

Direct Parent

Benzazepines

Alternative Parents

Substituents

Benzazepine
Azepine
N-alkylpiperazine
N-methylpiperazine
1,4-diazinane
Piperazine
Imidolactam
Benzenoid
Tertiary amine
Tertiary aliphatic amine
Amidine
Carboxylic acid amidine
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Amine
Hydrocarbon derivative
Organonitrogen compound
Organic nitrogen compound
Organopnictogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

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
logP	2.97	ALOGPS
logP	3.45	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Basic)	7.38	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	18.84 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	93.8 m³·mol⁻¹	ChemAxon
Polarizability	33.43 Å³	ChemAxon
Number of Rings	4	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
DeepCCS	[M-2H]-	196.446	30932474
DeepCCS	[M+Na]+	172.012	30932474
AllCCS	[M+H]+	170.0	32859911
AllCCS	[M+H-H2O]+	166.4	32859911
AllCCS	[M+NH4]+	173.4	32859911
AllCCS	[M+Na]+	174.3	32859911
AllCCS	[M-H]-	179.0	32859911
AllCCS	[M+Na-2H]-	178.4	32859911
AllCCS	[M+HCOO]-	177.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Perlapine	CN1CCN(CC1)C1=NC2=CC=CC=C2CC2=CC=CC=C12	3692.5	Standard polar	33892256
Perlapine	CN1CCN(CC1)C1=NC2=CC=CC=C2CC2=CC=CC=C12	2548.6	Standard non polar	33892256
Perlapine	CN1CCN(CC1)C1=NC2=CC=CC=C2CC2=CC=CC=C12	2486.8	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Perlapine GC-MS (Non-derivatized) - 70eV, Positive	splash10-06vl-5190000000-052fa97ddde13fbf7675	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Perlapine 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 - Perlapine 10V, Positive-QTOF	splash10-0006-0090000000-a602bedab438b026a046	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Perlapine 20V, Positive-QTOF	splash10-0006-0190000000-824c6b65784ae323d476	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Perlapine 40V, Positive-QTOF	splash10-0006-2930000000-03f8b0591f4592c17bf5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Perlapine 10V, Negative-QTOF	splash10-0006-0090000000-a6f81ee393f90c5b5eed	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Perlapine 20V, Negative-QTOF	splash10-0006-0090000000-401c1dfb18f3df4770c5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Perlapine 40V, Negative-QTOF	splash10-006x-8590000000-2fefb281f855f9ee6f0c	2016-08-03	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	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

15291

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Perlapine (HMDB0256346)

MOL for HMDB0256346 (Perlapine)

3D MOL for HMDB0256346 (Perlapine)

3D SDF for HMDB0256346 (Perlapine)

3D-SDF for HMDB0256346 (Perlapine)

PDB for HMDB0256346 (Perlapine)

3D PDB for HMDB0256346 (Perlapine)

SMILES for HMDB0256346 (Perlapine)

INCHI for HMDB0256346 (Perlapine)

Structure for HMDB0256346 (Perlapine)

3D Structure for HMDB0256346 (Perlapine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra