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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2017-11-21 17:34:33 UTC

Update Date

2022-03-07 03:18:13 UTC

HMDB ID

HMDB0240221

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Histapyrrodine

Description

Histapyrrodine belongs to the class of organic compounds known as phenylbenzamines. These are aromatic compounds consisting of a benzyl group that is N-linked to a benzamine. In humans, histapyrrodine is involved in the histapyrrodine h1-antihistamine action pathway. Histapyrrodine is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review very few articles have been published on Histapyrrodine.

Structure

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

HMDB0240221
     RDKit          3D
Histapyrrodine
 45 47  0  0  0  0  0  0  0  0999 V2000
   -3.1537   -3.6441   -0.6131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8255   -3.6113   -0.2714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2693   -2.4883    0.3471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0508   -1.3945    0.6237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5097   -0.1762    1.2702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8527    0.7193    0.3785 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4016    0.3447   -0.2293 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5141    0.2763    0.8249 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7138   -0.0662    0.1492 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8010   -1.3765   -0.4012 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2141   -1.3218   -1.0110 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9627   -0.4249   -0.0278 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8864   -0.0330    1.0037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3756    2.0128    0.0128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9353    3.1614    0.6219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4448    4.4107    0.2642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4094    4.4786   -0.7222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8578    3.3242   -1.3390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3470    2.0828   -0.9793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3900   -1.4486    0.2707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9499   -2.5571   -0.3426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5764   -4.5366   -1.1000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2269   -4.4860   -0.4984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2148   -2.5420    0.5815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3372    0.4046    1.7734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7826   -0.4898    2.0599 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3191   -0.6177   -0.7584 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7419    1.1000   -0.9870 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5960    1.2563    1.3391 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1978   -0.4694    1.5953 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0497   -1.5797   -1.1941 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8063   -2.1547    0.3931 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6495   -2.3150   -1.1114 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0834   -0.7903   -1.9934 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8069   -0.9532    0.4377 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2566    0.5212   -0.5415 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0744    0.9217    1.4812 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8717   -0.8863    1.7346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1827    3.1084    1.3887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0905    5.3035    0.7456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8144    5.4385   -1.0142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6153    3.4516   -2.1051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6983    1.2025   -1.4603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0256   -0.5779    0.4875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0109   -2.5782   -0.6143 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  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
 12 13  1  0
  6 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
  4 20  1  0
 20 21  2  0
 21  1  1  0
 13  9  1  0
 19 14  1  0
  1 22  1  0
  2 23  1  0
  3 24  1  0
  5 25  1  0
  5 26  1  0
  7 27  1  0
  7 28  1  0
  8 29  1  0
  8 30  1  0
 10 31  1  0
 10 32  1  0
 11 33  1  0
 11 34  1  0
 12 35  1  0
 12 36  1  0
 13 37  1  0
 13 38  1  0
 15 39  1  0
 16 40  1  0
 17 41  1  0
 18 42  1  0
 19 43  1  0
 20 44  1  0
 21 45  1  0
M  END


  Mrv1652309181718272D          

 21 23  0  0  0  0            999 V2000
   -3.2366   -1.2285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9510   -1.6410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9510   -2.4661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2366   -2.8786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5221   -2.4661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5221   -1.6410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2366   -0.4035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5222    0.0090    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5222    0.8340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8077   -0.4034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0932    0.0090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3787   -0.4034    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2924   -1.2239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5144   -1.3954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9269   -0.6809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3749   -0.0679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8078    1.2464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8078    2.0715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5221    2.4841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2367    2.0716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2367    1.2465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  1  1  0  0  0  0
  1  7  1  0  0  0  0
 10 11  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
  9 17  2  0  0  0  0
 21  9  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 16  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0240221

> <DATABASE_NAME>
hmdb

> <SMILES>
C(CN1CCCC1)N(CC1=CC=CC=C1)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C19H24N2/c1-3-9-18(10-4-1)17-21(19-11-5-2-6-12-19)16-15-20-13-7-8-14-20/h1-6,9-12H,7-8,13-17H2

> <INCHI_KEY>
MXHODDGKGSGCDI-UHFFFAOYSA-N

> <FORMULA>
C19H24N2

> <MOLECULAR_WEIGHT>
280.415

> <EXACT_MASS>
280.193948781

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
33.75832756836

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-benzyl-N-[2-(pyrrolidin-1-yl)ethyl]aniline

> <ALOGPS_LOGP>
4.20

> <JCHEM_LOGP>
4.230204781

> <ALOGPS_LOGS>
-3.67

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.268358939552924

> <JCHEM_POLAR_SURFACE_AREA>
6.48

> <JCHEM_REFRACTIVITY>
90.65930000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.97e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
histapyrrodine

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0240221
     RDKit          3D
Histapyrrodine
 45 47  0  0  0  0  0  0  0  0999 V2000
   -3.1537   -3.6441   -0.6131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8255   -3.6113   -0.2714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2693   -2.4883    0.3471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0508   -1.3945    0.6237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5097   -0.1762    1.2702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8527    0.7193    0.3785 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4016    0.3447   -0.2293 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5141    0.2763    0.8249 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7138   -0.0662    0.1492 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8010   -1.3765   -0.4012 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2141   -1.3218   -1.0110 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9627   -0.4249   -0.0278 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8864   -0.0330    1.0037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3756    2.0128    0.0128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9353    3.1614    0.6219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4448    4.4107    0.2642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4094    4.4786   -0.7222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8578    3.3242   -1.3390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3470    2.0828   -0.9793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3900   -1.4486    0.2707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9499   -2.5571   -0.3426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5764   -4.5366   -1.1000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2269   -4.4860   -0.4984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2148   -2.5420    0.5815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3372    0.4046    1.7734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7826   -0.4898    2.0599 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3191   -0.6177   -0.7584 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7419    1.1000   -0.9870 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5960    1.2563    1.3391 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1978   -0.4694    1.5953 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0497   -1.5797   -1.1941 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8063   -2.1547    0.3931 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6495   -2.3150   -1.1114 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0834   -0.7903   -1.9934 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8069   -0.9532    0.4377 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2566    0.5212   -0.5415 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0744    0.9217    1.4812 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8717   -0.8863    1.7346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1827    3.1084    1.3887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0905    5.3035    0.7456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8144    5.4385   -1.0142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6153    3.4516   -2.1051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6983    1.2025   -1.4603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0256   -0.5779    0.4875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0109   -2.5782   -0.6143 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  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
 12 13  1  0
  6 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
  4 20  1  0
 20 21  2  0
 21  1  1  0
 13  9  1  0
 19 14  1  0
  1 22  1  0
  2 23  1  0
  3 24  1  0
  5 25  1  0
  5 26  1  0
  7 27  1  0
  7 28  1  0
  8 29  1  0
  8 30  1  0
 10 31  1  0
 10 32  1  0
 11 33  1  0
 11 34  1  0
 12 35  1  0
 12 36  1  0
 13 37  1  0
 13 38  1  0
 15 39  1  0
 16 40  1  0
 17 41  1  0
 18 42  1  0
 19 43  1  0
 20 44  1  0
 21 45  1  0
M  END

HEADER    PROTEIN                                 18-SEP-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-SEP-17         0                                  
HETATM    1  C   UNK     0      -6.042  -2.293   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -7.375  -3.063   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -7.375  -4.603   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.042  -5.373   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.708  -4.603   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.708  -3.063   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -6.042  -0.753   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0      -4.708   0.017   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      -4.708   1.557   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.374  -0.753   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.041   0.017   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0      -0.707  -0.753   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0      -0.546  -2.285   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.960  -2.605   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.730  -1.271   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.700  -0.127   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.375   2.327   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -3.375   3.867   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.708   4.637   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -6.042   3.867   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -6.042   2.327   0.000  0.00  0.00           C+0
CONECT    1    2    6    7                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    1    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9   17   21    8                                                  
CONECT   10   11    8                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   16                                                  
CONECT   13   14   12                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   12                                                       
CONECT   17   18    9                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20    9                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    HMDB0240221
HETATM    1  C1  UNL     1      -3.154  -3.644  -0.613  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.826  -3.611  -0.271  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.269  -2.488   0.347  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.051  -1.394   0.624  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.510  -0.176   1.270  1.00  0.00           C  
HETATM    6  N1  UNL     1      -0.853   0.719   0.379  1.00  0.00           N  
HETATM    7  C6  UNL     1       0.402   0.345  -0.229  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.514   0.276   0.825  1.00  0.00           C  
HETATM    9  N2  UNL     1       2.714  -0.066   0.149  1.00  0.00           N  
HETATM   10  C8  UNL     1       2.801  -1.376  -0.401  1.00  0.00           C  
HETATM   11  C9  UNL     1       4.214  -1.322  -1.011  1.00  0.00           C  
HETATM   12  C10 UNL     1       4.963  -0.425  -0.028  1.00  0.00           C  
HETATM   13  C11 UNL     1       3.886  -0.033   1.004  1.00  0.00           C  
HETATM   14  C12 UNL     1      -1.376   2.013   0.013  1.00  0.00           C  
HETATM   15  C13 UNL     1      -0.935   3.161   0.622  1.00  0.00           C  
HETATM   16  C14 UNL     1      -1.445   4.411   0.264  1.00  0.00           C  
HETATM   17  C15 UNL     1      -2.409   4.479  -0.722  1.00  0.00           C  
HETATM   18  C16 UNL     1      -2.858   3.324  -1.339  1.00  0.00           C  
HETATM   19  C17 UNL     1      -2.347   2.083  -0.979  1.00  0.00           C  
HETATM   20  C18 UNL     1      -3.390  -1.449   0.271  1.00  0.00           C  
HETATM   21  C19 UNL     1      -3.950  -2.557  -0.343  1.00  0.00           C  
HETATM   22  H1  UNL     1      -3.576  -4.537  -1.100  1.00  0.00           H  
HETATM   23  H2  UNL     1      -1.227  -4.486  -0.498  1.00  0.00           H  
HETATM   24  H3  UNL     1      -0.215  -2.542   0.581  1.00  0.00           H  
HETATM   25  H4  UNL     1      -2.337   0.405   1.773  1.00  0.00           H  
HETATM   26  H5  UNL     1      -0.783  -0.490   2.060  1.00  0.00           H  
HETATM   27  H6  UNL     1       0.319  -0.618  -0.758  1.00  0.00           H  
HETATM   28  H7  UNL     1       0.742   1.100  -0.987  1.00  0.00           H  
HETATM   29  H8  UNL     1       1.596   1.256   1.339  1.00  0.00           H  
HETATM   30  H9  UNL     1       1.198  -0.469   1.595  1.00  0.00           H  
HETATM   31  H10 UNL     1       2.050  -1.580  -1.194  1.00  0.00           H  
HETATM   32  H11 UNL     1       2.806  -2.155   0.393  1.00  0.00           H  
HETATM   33  H12 UNL     1       4.649  -2.315  -1.111  1.00  0.00           H  
HETATM   34  H13 UNL     1       4.083  -0.790  -1.993  1.00  0.00           H  
HETATM   35  H14 UNL     1       5.807  -0.953   0.438  1.00  0.00           H  
HETATM   36  H15 UNL     1       5.257   0.521  -0.541  1.00  0.00           H  
HETATM   37  H16 UNL     1       4.074   0.922   1.481  1.00  0.00           H  
HETATM   38  H17 UNL     1       3.872  -0.886   1.735  1.00  0.00           H  
HETATM   39  H18 UNL     1      -0.183   3.108   1.389  1.00  0.00           H  
HETATM   40  H19 UNL     1      -1.090   5.304   0.746  1.00  0.00           H  
HETATM   41  H20 UNL     1      -2.814   5.438  -1.014  1.00  0.00           H  
HETATM   42  H21 UNL     1      -3.615   3.452  -2.105  1.00  0.00           H  
HETATM   43  H22 UNL     1      -2.698   1.202  -1.460  1.00  0.00           H  
HETATM   44  H23 UNL     1      -4.026  -0.578   0.487  1.00  0.00           H  
HETATM   45  H24 UNL     1      -5.011  -2.578  -0.614  1.00  0.00           H  
CONECT    1    2    2   21   22
CONECT    2    3   23
CONECT    3    4    4   24
CONECT    4    5   20
CONECT    5    6   25   26
CONECT    6    7   14
CONECT    7    8   27   28
CONECT    8    9   29   30
CONECT    9   10   13
CONECT   10   11   31   32
CONECT   11   12   33   34
CONECT   12   13   35   36
CONECT   13   37   38
CONECT   14   15   15   19
CONECT   15   16   39
CONECT   16   17   17   40
CONECT   17   18   41
CONECT   18   19   19   42
CONECT   19   43
CONECT   20   21   21   44
CONECT   21   45
END

HMDB0240221
     RDKit          3D
Histapyrrodine
 45 47  0  0  0  0  0  0  0  0999 V2000
   -3.1537   -3.6441   -0.6131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8255   -3.6113   -0.2714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2693   -2.4883    0.3471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0508   -1.3945    0.6237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5097   -0.1762    1.2702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8527    0.7193    0.3785 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4016    0.3447   -0.2293 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5141    0.2763    0.8249 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7138   -0.0662    0.1492 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8010   -1.3765   -0.4012 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2141   -1.3218   -1.0110 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9627   -0.4249   -0.0278 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8864   -0.0330    1.0037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3756    2.0128    0.0128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9353    3.1614    0.6219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4448    4.4107    0.2642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4094    4.4786   -0.7222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8578    3.3242   -1.3390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3470    2.0828   -0.9793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3900   -1.4486    0.2707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9499   -2.5571   -0.3426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5764   -4.5366   -1.1000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2269   -4.4860   -0.4984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2148   -2.5420    0.5815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3372    0.4046    1.7734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7826   -0.4898    2.0599 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3191   -0.6177   -0.7584 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7419    1.1000   -0.9870 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5960    1.2563    1.3391 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1978   -0.4694    1.5953 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0497   -1.5797   -1.1941 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8063   -2.1547    0.3931 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6495   -2.3150   -1.1114 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0834   -0.7903   -1.9934 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8069   -0.9532    0.4377 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2566    0.5212   -0.5415 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0744    0.9217    1.4812 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8717   -0.8863    1.7346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1827    3.1084    1.3887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0905    5.3035    0.7456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8144    5.4385   -1.0142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6153    3.4516   -2.1051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6983    1.2025   -1.4603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0256   -0.5779    0.4875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0109   -2.5782   -0.6143 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  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
 12 13  1  0
  6 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
  4 20  1  0
 20 21  2  0
 21  1  1  0
 13  9  1  0
 19 14  1  0
  1 22  1  0
  2 23  1  0
  3 24  1  0
  5 25  1  0
  5 26  1  0
  7 27  1  0
  7 28  1  0
  8 29  1  0
  8 30  1  0
 10 31  1  0
 10 32  1  0
 11 33  1  0
 11 34  1  0
 12 35  1  0
 12 36  1  0
 13 37  1  0
 13 38  1  0
 15 39  1  0
 16 40  1  0
 17 41  1  0
 18 42  1  0
 19 43  1  0
 20 44  1  0
 21 45  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Luvistin	HMDB
Histapyrrodine	HMDB
Histapyrrodine hydrochloride	MeSH, HMDB
N-Phenyl-N-benzyl-1-pyrrolidineethanamine	MeSH, HMDB
Domistan	MeSH, HMDB

Chemical Formula

C₁₉H₂₄N₂

Average Molecular Weight

280.415

Monoisotopic Molecular Weight

280.193948781

IUPAC Name

N-benzyl-N-[2-(pyrrolidin-1-yl)ethyl]aniline

Traditional Name

histapyrrodine

CAS Registry Number

493-80-1

SMILES

C(CN1CCCC1)N(CC1=CC=CC=C1)C1=CC=CC=C1

InChI Identifier

InChI=1S/C19H24N2/c1-3-9-18(10-4-1)17-21(19-11-5-2-6-12-19)16-15-20-13-7-8-14-20/h1-6,9-12H,7-8,13-17H2

InChI Key

MXHODDGKGSGCDI-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylbenzamines. These are aromatic compounds consisting of a benzyl group that is N-linked to a benzamine.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenylmethylamines

Direct Parent

Phenylbenzamines

Alternative Parents

Substituents

Phenylbenzamine
Benzylamine
Tertiary aliphatic/aromatic amine
Aniline or substituted anilines
Dialkylarylamine
Aralkylamine
N-alkylpyrrolidine
Pyrrolidine
Tertiary amine
Tertiary aliphatic amine
Azacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organopnictogen compound
Organonitrogen compound
Organic nitrogen compound
Amine
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

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	4.2	ALOGPS
logP	4.23	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Basic)	9.27	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	6.48 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	90.66 m³·mol⁻¹	ChemAxon
Polarizability	33.76 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	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
AllCCS	[M-H]-	173.573	31661259
AllCCS	[M+H]+	168.564	31661259
DeepCCS	[M+H]+	168.14	30932474
DeepCCS	[M-H]-	165.782	30932474
DeepCCS	[M-2H]-	198.668	30932474
DeepCCS	[M+Na]+	174.233	30932474
AllCCS	[M+H]+	168.6	32859911
AllCCS	[M+H-H2O]+	165.1	32859911
AllCCS	[M+NH4]+	171.8	32859911
AllCCS	[M+Na]+	172.7	32859911
AllCCS	[M-H]-	173.6	32859911
AllCCS	[M+Na-2H]-	173.3	32859911
AllCCS	[M+HCOO]-	173.1	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.	5.34 minutes	32390414
Predicted by Siyang on May 30, 2022	12.0168 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.23 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1416.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	259.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	181.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	179.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	101.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	451.2 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	418.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	230.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1115.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	356.4 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	1343.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	308.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	332.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	375.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	265.0 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	8.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Histapyrrodine	C(CN1CCCC1)N(CC1=CC=CC=C1)C1=CC=CC=C1	2917.2	Standard polar	33892256
Histapyrrodine	C(CN1CCCC1)N(CC1=CC=CC=C1)C1=CC=CC=C1	2322.9	Standard non polar	33892256
Histapyrrodine	C(CN1CCCC1)N(CC1=CC=CC=C1)C1=CC=CC=C1	2266.6	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 - Histapyrrodine GC-MS (Non-derivatized) - 70eV, Positive	splash10-000x-9320000000-3e2412986db4cd0a0192	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Histapyrrodine 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 - Histapyrrodine 10V, Positive-QTOF	splash10-001i-5090000000-60f77a3e77e22bbe506b	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Histapyrrodine 20V, Positive-QTOF	splash10-0007-9020000000-d8a82ac5280feca0a602	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Histapyrrodine 40V, Positive-QTOF	splash10-0006-9000000000-414a981eca34c914be57	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Histapyrrodine 10V, Negative-QTOF	splash10-004i-0190000000-ee5fa81c6e7696c5d19a	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Histapyrrodine 20V, Negative-QTOF	splash10-004i-5690000000-f868f113d2fa858eb241	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Histapyrrodine 40V, Negative-QTOF	splash10-00u6-9500000000-c0365328614524e69165	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Histapyrrodine 10V, Positive-QTOF	splash10-001i-0090000000-898c03610f8e40ccc859	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Histapyrrodine 20V, Positive-QTOF	splash10-01qc-6090000000-32cca95cda0f119d8dc2	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Histapyrrodine 40V, Positive-QTOF	splash10-001i-9000000000-ab3e2f1d9819a6a5ba4b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Histapyrrodine 10V, Negative-QTOF	splash10-004i-0390000000-95aa35ae7dee75559255	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Histapyrrodine 20V, Negative-QTOF	splash10-004i-4590000000-82098facb43bc3065ba9	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Histapyrrodine 40V, Negative-QTOF	splash10-003r-5900000000-21f9c6b5a0a3b7fab244	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Histapyrrodine H1-Antihistamine Action		Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB13479

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

61430

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Histapyrrodine

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

SIGWALD J, RAYMONDEAUD C: [Neurosedative action of histapyrrodine; its therapeutic value in anxiety, neurotonic manifestations and states of aggression]. Sem Med Prof Med Soc. 1957 Jan 30;33(4):161-2. [PubMed:13421807 ]

Showing metabocard for Histapyrrodine (HMDB0240221)

MOL for HMDB0240221 (Histapyrrodine)

3D MOL for HMDB0240221 (Histapyrrodine)

3D SDF for HMDB0240221 (Histapyrrodine)

3D-SDF for HMDB0240221 (Histapyrrodine)

PDB for HMDB0240221 (Histapyrrodine)

3D PDB for HMDB0240221 (Histapyrrodine)

SMILES for HMDB0240221 (Histapyrrodine)

INCHI for HMDB0240221 (Histapyrrodine)

Structure for HMDB0240221 (Histapyrrodine)

3D Structure for HMDB0240221 (Histapyrrodine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra