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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2017-11-21 17:44:01 UTC

Update Date

2022-03-07 03:18:14 UTC

HMDB ID

HMDB0240248

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Pyrrobutamine

Description

Pyrrobutamine belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids. In humans, pyrrobutamine is involved in the pyrrobutamine h1-antihistamine action pathway. Pyrrobutamine 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 Pyrrobutamine.

Structure

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

HMDB0240248
     RDKit          3D
Pyrrobutamine
 44 46  0  0  0  0  0  0  0  0999 V2000
   -6.4110   -2.3004    0.9668 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.7670   -1.8997    0.4984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7298   -1.9263    1.4227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4363   -1.6152    1.0729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1268   -1.2566   -0.2511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7635   -0.9578   -0.6648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1760    0.2577   -0.0161 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7218    0.0843    0.9122 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1952   -1.2112    1.3736 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6116   -1.4280    1.1601 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4183   -0.5729    2.0129 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8068   -0.8242    1.4054 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4653   -0.5814   -0.0710 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0166   -1.0016   -0.1686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6055    1.5936   -0.3859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4306    1.8038   -1.4634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8909    3.0866   -1.8251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4974    4.1582   -1.0731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6811    3.9890    0.0004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2387    2.6962    0.3368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1791   -1.2450   -1.1247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4855   -1.5523   -0.8005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9752   -2.2048    2.4507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6365   -1.6390    1.8005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0326   -1.7637   -0.6280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8218   -0.7478   -1.8007 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1497    1.0132    1.3591 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0168   -1.2332    2.5165 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6316   -2.0449    0.9982 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2126    0.5053    1.8761 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4335   -0.9003    3.0625 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5454   -0.0941    1.7299 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0725   -1.8813    1.5734 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5626    0.5125   -0.2145 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1226   -1.1446   -0.7384 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4007   -0.1163   -0.5007 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8745   -1.8619   -0.8507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7293    0.9654   -2.0687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5379    3.1933   -2.6816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8386    5.1775   -1.3280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3530    4.8394    0.6183 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4028    2.6433    1.2116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0274   -0.9865   -2.1853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2891   -1.5283   -1.5327 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
  7 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  2  0
 22  2  1  0
 14 10  1  0
 20 15  1  0
  3 23  1  0
  4 24  1  0
  6 25  1  0
  6 26  1  0
  8 27  1  0
  9 28  1  0
  9 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  0
 12 33  1  0
 13 34  1  0
 13 35  1  0
 14 36  1  0
 14 37  1  0
 16 38  1  0
 17 39  1  0
 18 40  1  0
 19 41  1  0
 20 42  1  0
 21 43  1  0
 22 44  1  0
M  END

      
  Mrv1652311211718432D          

 22 24  0  0  0  0            999 V2000
   -1.9194    0.9258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3319    0.2114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0944    0.9258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6818    1.6403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6818    0.2114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1568    0.2114    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6419    0.8788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4265    0.6239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4265   -0.2010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6419   -0.4559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1429    1.6403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5555    2.3549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1431    3.0693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6818    3.0694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0944    2.3548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1429    0.2114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5555   -0.5029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3806   -0.5030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7931    0.2113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3806    0.9258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5555    0.9259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6181    0.2113    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
  4 11  2  0  0  0  0
 15  4  1  0  0  0  0
  5 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
 16 17  2  0  0  0  0
 21 16  1  0  0  0  0
 19 22  1  0  0  0  0
  2  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6 10  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0240248

> <DATABASE_NAME>
hmdb

> <SMILES>
ClC1=CC=C(C\C(=C/CN2CCCC2)C2=CC=CC=C2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H22ClN/c21-20-10-8-17(9-11-20)16-19(18-6-2-1-3-7-18)12-15-22-13-4-5-14-22/h1-3,6-12H,4-5,13-16H2/b19-12+

> <INCHI_KEY>
WDYYVNNRTDZKAZ-XDHOZWIPSA-N

> <FORMULA>
C20H22ClN

> <MOLECULAR_WEIGHT>
311.85

> <EXACT_MASS>
311.1440774

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
35.67292382440608

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-[(2E)-4-(4-chlorophenyl)-3-phenylbut-2-en-1-yl]pyrrolidine

> <ALOGPS_LOGP>
5.35

> <JCHEM_LOGP>
5.412167641999999

> <ALOGPS_LOGS>
-5.26

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
8.909880536856198

> <JCHEM_POLAR_SURFACE_AREA>
3.24

> <JCHEM_REFRACTIVITY>
96.24310000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.71e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
C20H22ClN

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0240248
     RDKit          3D
Pyrrobutamine
 44 46  0  0  0  0  0  0  0  0999 V2000
   -6.4110   -2.3004    0.9668 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.7670   -1.8997    0.4984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7298   -1.9263    1.4227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4363   -1.6152    1.0729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1268   -1.2566   -0.2511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7635   -0.9578   -0.6648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1760    0.2577   -0.0161 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7218    0.0843    0.9122 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1952   -1.2112    1.3736 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6116   -1.4280    1.1601 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4183   -0.5729    2.0129 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8068   -0.8242    1.4054 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4653   -0.5814   -0.0710 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0166   -1.0016   -0.1686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6055    1.5936   -0.3859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4306    1.8038   -1.4634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8909    3.0866   -1.8251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4974    4.1582   -1.0731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6811    3.9890    0.0004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2387    2.6962    0.3368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1791   -1.2450   -1.1247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4855   -1.5523   -0.8005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9752   -2.2048    2.4507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6365   -1.6390    1.8005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0326   -1.7637   -0.6280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8218   -0.7478   -1.8007 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1497    1.0132    1.3591 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0168   -1.2332    2.5165 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6316   -2.0449    0.9982 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2126    0.5053    1.8761 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4335   -0.9003    3.0625 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5454   -0.0941    1.7299 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0725   -1.8813    1.5734 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5626    0.5125   -0.2145 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1226   -1.1446   -0.7384 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4007   -0.1163   -0.5007 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8745   -1.8619   -0.8507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7293    0.9654   -2.0687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5379    3.1933   -2.6816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8386    5.1775   -1.3280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3530    4.8394    0.6183 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4028    2.6433    1.2116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0274   -0.9865   -2.1853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2891   -1.5283   -1.5327 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
  7 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  2  0
 22  2  1  0
 14 10  1  0
 20 15  1  0
  3 23  1  0
  4 24  1  0
  6 25  1  0
  6 26  1  0
  8 27  1  0
  9 28  1  0
  9 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  0
 12 33  1  0
 13 34  1  0
 13 35  1  0
 14 36  1  0
 14 37  1  0
 16 38  1  0
 17 39  1  0
 18 40  1  0
 19 41  1  0
 20 42  1  0
 21 43  1  0
 22 44  1  0
M  END

HEADER    PROTEIN                                 21-NOV-17   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-NOV-17         0                                  
HETATM    1  C   UNK     0      -3.583   1.728   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.353   0.395   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.043   1.728   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.273   3.062   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.273   0.395   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      -5.893   0.395   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      -6.798   1.640   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -8.263   1.165   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -8.263  -0.375   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -6.798  -0.851   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.267   3.062   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.037   4.396   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.267   5.729   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.273   5.730   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.043   4.396   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.267   0.395   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.037  -0.939   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.577  -0.939   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.347   0.394   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.577   1.728   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.037   1.728   0.000  0.00  0.00           C+0
HETATM   22 Cl   UNK     0       4.887   0.394   0.000  0.00  0.00          Cl+0
CONECT    1    2    3                                                       
CONECT    2    1    6                                                       
CONECT    3    1    4    5                                                  
CONECT    4    3   11   15                                                  
CONECT    5    3   16                                                       
CONECT    6    2    7   10                                                  
CONECT    7    8    6                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    6                                                       
CONECT   11   12    4                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14    4                                                       
CONECT   16    5   17   21                                                  
CONECT   17   18   16                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   22                                                  
CONECT   20   19   21                                                       
CONECT   21   20   16                                                       
CONECT   22   19                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

COMPND    HMDB0240248
HETATM    1 CL1  UNL     1      -6.411  -2.300   0.967  1.00  0.00          CL  
HETATM    2  C1  UNL     1      -4.767  -1.900   0.498  1.00  0.00           C  
HETATM    3  C2  UNL     1      -3.730  -1.926   1.423  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.436  -1.615   1.073  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.127  -1.257  -0.251  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.764  -0.958  -0.665  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.176   0.258  -0.016  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.722   0.084   0.912  1.00  0.00           C  
HETATM    9  C8  UNL     1       1.195  -1.211   1.374  1.00  0.00           C  
HETATM   10  N1  UNL     1       2.612  -1.428   1.160  1.00  0.00           N  
HETATM   11  C9  UNL     1       3.418  -0.573   2.013  1.00  0.00           C  
HETATM   12  C10 UNL     1       4.807  -0.824   1.405  1.00  0.00           C  
HETATM   13  C11 UNL     1       4.465  -0.581  -0.071  1.00  0.00           C  
HETATM   14  C12 UNL     1       3.017  -1.002  -0.169  1.00  0.00           C  
HETATM   15  C13 UNL     1      -0.606   1.594  -0.386  1.00  0.00           C  
HETATM   16  C14 UNL     1      -1.431   1.804  -1.463  1.00  0.00           C  
HETATM   17  C15 UNL     1      -1.891   3.087  -1.825  1.00  0.00           C  
HETATM   18  C16 UNL     1      -1.497   4.158  -1.073  1.00  0.00           C  
HETATM   19  C17 UNL     1      -0.681   3.989   0.000  1.00  0.00           C  
HETATM   20  C18 UNL     1      -0.239   2.696   0.337  1.00  0.00           C  
HETATM   21  C19 UNL     1      -3.179  -1.245  -1.125  1.00  0.00           C  
HETATM   22  C20 UNL     1      -4.485  -1.552  -0.801  1.00  0.00           C  
HETATM   23  H1  UNL     1      -3.975  -2.205   2.451  1.00  0.00           H  
HETATM   24  H2  UNL     1      -1.637  -1.639   1.801  1.00  0.00           H  
HETATM   25  H3  UNL     1      -0.033  -1.764  -0.628  1.00  0.00           H  
HETATM   26  H4  UNL     1      -0.822  -0.748  -1.801  1.00  0.00           H  
HETATM   27  H5  UNL     1       1.150   1.013   1.359  1.00  0.00           H  
HETATM   28  H6  UNL     1       1.017  -1.233   2.517  1.00  0.00           H  
HETATM   29  H7  UNL     1       0.632  -2.045   0.998  1.00  0.00           H  
HETATM   30  H8  UNL     1       3.213   0.505   1.876  1.00  0.00           H  
HETATM   31  H9  UNL     1       3.434  -0.900   3.063  1.00  0.00           H  
HETATM   32  H10 UNL     1       5.545  -0.094   1.730  1.00  0.00           H  
HETATM   33  H11 UNL     1       5.073  -1.881   1.573  1.00  0.00           H  
HETATM   34  H12 UNL     1       4.563   0.512  -0.214  1.00  0.00           H  
HETATM   35  H13 UNL     1       5.123  -1.145  -0.738  1.00  0.00           H  
HETATM   36  H14 UNL     1       2.401  -0.116  -0.501  1.00  0.00           H  
HETATM   37  H15 UNL     1       2.874  -1.862  -0.851  1.00  0.00           H  
HETATM   38  H16 UNL     1      -1.729   0.965  -2.069  1.00  0.00           H  
HETATM   39  H17 UNL     1      -2.538   3.193  -2.682  1.00  0.00           H  
HETATM   40  H18 UNL     1      -1.839   5.177  -1.328  1.00  0.00           H  
HETATM   41  H19 UNL     1      -0.353   4.839   0.618  1.00  0.00           H  
HETATM   42  H20 UNL     1       0.403   2.643   1.212  1.00  0.00           H  
HETATM   43  H21 UNL     1      -3.027  -0.987  -2.185  1.00  0.00           H  
HETATM   44  H22 UNL     1      -5.289  -1.528  -1.533  1.00  0.00           H  
CONECT    1    2
CONECT    2    3    3   22
CONECT    3    4   23
CONECT    4    5    5   24
CONECT    5    6   21
CONECT    6    7   25   26
CONECT    7    8    8   15
CONECT    8    9   27
CONECT    9   10   28   29
CONECT   10   11   14
CONECT   11   12   30   31
CONECT   12   13   32   33
CONECT   13   14   34   35
CONECT   14   36   37
CONECT   15   16   16   20
CONECT   16   17   38
CONECT   17   18   18   39
CONECT   18   19   40
CONECT   19   20   20   41
CONECT   20   42
CONECT   21   22   22   43
CONECT   22   44
END

HMDB0240248
     RDKit          3D
Pyrrobutamine
 44 46  0  0  0  0  0  0  0  0999 V2000
   -6.4110   -2.3004    0.9668 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.7670   -1.8997    0.4984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7298   -1.9263    1.4227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4363   -1.6152    1.0729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1268   -1.2566   -0.2511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7635   -0.9578   -0.6648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1760    0.2577   -0.0161 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7218    0.0843    0.9122 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1952   -1.2112    1.3736 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6116   -1.4280    1.1601 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4183   -0.5729    2.0129 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8068   -0.8242    1.4054 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4653   -0.5814   -0.0710 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0166   -1.0016   -0.1686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6055    1.5936   -0.3859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4306    1.8038   -1.4634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8909    3.0866   -1.8251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4974    4.1582   -1.0731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6811    3.9890    0.0004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2387    2.6962    0.3368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1791   -1.2450   -1.1247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4855   -1.5523   -0.8005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9752   -2.2048    2.4507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6365   -1.6390    1.8005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0326   -1.7637   -0.6280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8218   -0.7478   -1.8007 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1497    1.0132    1.3591 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0168   -1.2332    2.5165 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6316   -2.0449    0.9982 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2126    0.5053    1.8761 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4335   -0.9003    3.0625 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5454   -0.0941    1.7299 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0725   -1.8813    1.5734 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5626    0.5125   -0.2145 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1226   -1.1446   -0.7384 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4007   -0.1163   -0.5007 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8745   -1.8619   -0.8507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7293    0.9654   -2.0687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5379    3.1933   -2.6816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8386    5.1775   -1.3280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3530    4.8394    0.6183 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4028    2.6433    1.2116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0274   -0.9865   -2.1853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2891   -1.5283   -1.5327 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
  7 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  2  0
 22  2  1  0
 14 10  1  0
 20 15  1  0
  3 23  1  0
  4 24  1  0
  6 25  1  0
  6 26  1  0
  8 27  1  0
  9 28  1  0
  9 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  0
 12 33  1  0
 13 34  1  0
 13 35  1  0
 14 36  1  0
 14 37  1  0
 16 38  1  0
 17 39  1  0
 18 40  1  0
 19 41  1  0
 20 42  1  0
 21 43  1  0
 22 44  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Pyrrobutamine, (Z)-isomer	MeSH
Pyrrobutamine, phosphate (1:2) salt, (e)-isomer	MeSH
1-(gamma-p-Chlorobenzylcinnamyl)pyrrolidine	MeSH
Pirrobutamine	MeSH
Pyrrobutamine, hydrobromide salt, (Z)-isomer	MeSH
Pyrrobutamine, phosphate (1:2) salt	MeSH
Pyrrobutamine, phosphate (2:1) salt, (trans)-isomer	MeSH

Chemical Formula

C₂₀H₂₂ClN

Average Molecular Weight

311.85

Monoisotopic Molecular Weight

311.1440774

IUPAC Name

1-[(2E)-4-(4-chlorophenyl)-3-phenylbut-2-en-1-yl]pyrrolidine

Traditional Name

C20H22ClN

CAS Registry Number

91-82-7

SMILES

ClC1=CC=C(C\C(=C/CN2CCCC2)C2=CC=CC=C2)C=C1

InChI Identifier

InChI=1S/C20H22ClN/c21-20-10-8-17(9-11-20)16-19(18-6-2-1-3-7-18)12-15-22-13-4-5-14-22/h1-3,6-12H,4-5,13-16H2/b19-12+

InChI Key

WDYYVNNRTDZKAZ-XDHOZWIPSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Stilbenes

Sub Class

Not Available

Direct Parent

Stilbenes

Alternative Parents

Substituents

Stilbene
Styrene
Chlorobenzene
Halobenzene
Aryl chloride
Benzenoid
N-alkylpyrrolidine
Aryl halide
Monocyclic benzene moiety
Pyrrolidine
Tertiary aliphatic amine
Tertiary amine
Azacycle
Organoheterocyclic compound
Organonitrogen compound
Organochloride
Organohalogen compound
Amine
Hydrocarbon derivative
Organopnictogen compound
Organic nitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Exogenous (HMDB: HMDB0240248)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Pyrrobutamine H1-Antihistamine Action (PathBank: SMP0062887)

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	5.35	ALOGPS
logP	5.41	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Basic)	8.91	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	3.24 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	96.24 m³·mol⁻¹	ChemAxon
Polarizability	35.67 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
AllCCS	[M+H]+	174.564	31661259
AllCCS	[M-H]-	179.075	31661259
DeepCCS	[M+H]+	177.228	30932474
DeepCCS	[M-H]-	174.87	30932474
DeepCCS	[M-2H]-	207.755	30932474
DeepCCS	[M+Na]+	183.321	30932474
AllCCS	[M+H]+	174.6	32859911
AllCCS	[M+H-H2O]+	171.2	32859911
AllCCS	[M+NH4]+	177.7	32859911
AllCCS	[M+Na]+	178.6	32859911
AllCCS	[M-H]-	179.1	32859911
AllCCS	[M+Na-2H]-	178.7	32859911
AllCCS	[M+HCOO]-	178.3	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.	9.32 minutes	32390414
Predicted by Siyang on May 30, 2022	14.9481 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.64 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1941.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	366.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	208.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	207.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	296.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	641.7 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	693.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	108.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1437.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	569.5 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	1591.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	393.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	403.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	264.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	141.5 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	8.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Pyrrobutamine	ClC1=CC=C(C\C(=C/CN2CCCC2)C2=CC=CC=C2)C=C1	3279.5	Standard polar	33892256
Pyrrobutamine	ClC1=CC=C(C\C(=C/CN2CCCC2)C2=CC=CC=C2)C=C1	2460.4	Standard non polar	33892256
Pyrrobutamine	ClC1=CC=C(C\C(=C/CN2CCCC2)C2=CC=CC=C2)C=C1	2474.2	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 - Pyrrobutamine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pyrrobutamine 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 - Pyrrobutamine 10V, Positive-QTOF	splash10-03di-0129000000-8a96b4d1f332a08cff78	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pyrrobutamine 20V, Positive-QTOF	splash10-03gl-4983000000-f1d9a2fb9ae99efe57f7	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pyrrobutamine 40V, Positive-QTOF	splash10-0fi0-4930000000-ba22a383856747920bc7	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pyrrobutamine 10V, Negative-QTOF	splash10-03di-0009000000-9efb2113a2e783168485	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pyrrobutamine 20V, Negative-QTOF	splash10-03k9-6019000000-eaae45dae1de66ee61fa	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pyrrobutamine 40V, Negative-QTOF	splash10-00di-9010000000-77bfdd6f2c0ef3ac8010	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pyrrobutamine 10V, Negative-QTOF	splash10-004i-0093000000-1b979f80a163c36dd341	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pyrrobutamine 20V, Negative-QTOF	splash10-03di-4098000000-aed83a3b69138b29e505	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pyrrobutamine 40V, Negative-QTOF	splash10-001i-9350000000-f4131d9fcd062dec7d44	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pyrrobutamine 10V, Positive-QTOF	splash10-03dl-0079000000-467b4fd79ab98c330a7a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pyrrobutamine 20V, Positive-QTOF	splash10-01tc-5696000000-f6450bf975e596f9184f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pyrrobutamine 40V, Positive-QTOF	splash10-004i-4931000000-f4eb7364c8ac3bffdf05	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Pyrrobutamine 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

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4447659

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Pyrrobutamine

METLIN ID

Not Available

PubChem Compound

5284614

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

MOTHERSILL MH, MILLS J, LEE HM, ANDERSON RC, HARRIS PN: Chemical and pharmacological characteristics of the antihistaminic compound, pyrrobutamine. Ann Allergy. 1953 Nov-Dec;11(6):754-7. [PubMed:13114796 ]

Showing metabocard for Pyrrobutamine (HMDB0240248)

MOL for HMDB0240248 (Pyrrobutamine)

3D MOL for HMDB0240248 (Pyrrobutamine)

3D SDF for HMDB0240248 (Pyrrobutamine)

3D-SDF for HMDB0240248 (Pyrrobutamine)

PDB for HMDB0240248 (Pyrrobutamine)

3D PDB for HMDB0240248 (Pyrrobutamine)

SMILES for HMDB0240248 (Pyrrobutamine)

INCHI for HMDB0240248 (Pyrrobutamine)

Structure for HMDB0240248 (Pyrrobutamine)

3D Structure for HMDB0240248 (Pyrrobutamine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra