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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 21:17:22 UTC

Update Date

2021-09-23 21:17:23 UTC

HMDB ID

HMDB0302866

Secondary Accession Numbers

None

Metabolite Identification

Common Name

2-trans-8-trans-Piperamide-C-9-2

Description

2-trans-8-trans-piperamide-c-9-2 is a member of the class of compounds known as benzodioxoles. Benzodioxoles are organic compounds containing a benzene ring fused to either isomers of dioxole. Dioxole is a five-membered unsaturated ring of two oxygen atoms and three carbon atoms. 2-trans-8-trans-piperamide-c-9-2 is practically insoluble (in water) and a moderately basic compound (based on its pKa). 2-trans-8-trans-piperamide-c-9-2 can be found in pepper (spice), which makes 2-trans-8-trans-piperamide-c-9-2 a potential biomarker for the consumption of this food product.

Structure

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

HMDB0302866
     RDKit          3D
2-trans-8-trans-Piperamide-C-9-2
 49 51  0  0  0  0  0  0  0  0999 V2000
   -5.1715    2.2018   -1.2237 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8186    1.1218   -0.5658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4306    0.8957   -0.3505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8916   -0.1013    0.2703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4076   -0.2469    0.4436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6813    0.8962   -0.1890 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8201    0.7524   -0.0155 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3509   -0.4952   -0.6318 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8239   -0.5585   -0.4137 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5329    0.3399    0.2255 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9577    0.2897    0.4427 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5955    1.3055    1.1369 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9485    1.3267    1.3828 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7224    0.2840    0.9168 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1336   -0.7432    0.2249 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7442   -0.7359   -0.0111 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1192   -1.6430   -0.1210 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3423   -0.9409   -0.1187 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0942   -0.0323    0.9708 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9087    0.3388   -0.1682 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3338    0.7091   -0.4686 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.7300    1.3407    0.3238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3471    1.2003   -1.4513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6178   -1.1868   -1.4310 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.8046   -0.9299    1.6168 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv0541 02241212542D          

 24 26  0  0  0  0            999 V2000
    7.5638    4.5457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8481    4.5457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.1336    3.3082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.2954    3.3082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0800    3.0533    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    7.4561    5.3637    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  1 24  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0302866

> <DATABASE_NAME>
hmdb

> <SMILES>
O=C(\C=C\CCCC\C=C\C1=CC=C2OCOC2=C1)N1CCCC1

> <INCHI_IDENTIFIER>
InChI=1S/C20H25NO3/c22-20(21-13-7-8-14-21)10-6-4-2-1-3-5-9-17-11-12-18-19(15-17)24-16-23-18/h5-6,9-12,15H,1-4,7-8,13-14,16H2/b9-5+,10-6+

> <INCHI_KEY>
BYKNKNBUHGFXQF-NXZHAISVSA-N

> <FORMULA>
C20H25NO3

> <MOLECULAR_WEIGHT>
327.4174

> <EXACT_MASS>
327.183443671

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
38.594227410428225

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E,8E)-9-(2H-1,3-benzodioxol-5-yl)-1-(pyrrolidin-1-yl)nona-2,8-dien-1-one

> <ALOGPS_LOGP>
4.49

> <JCHEM_LOGP>
4.111017045333334

> <ALOGPS_LOGS>
-4.86

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
2.1718108996643624

> <JCHEM_POLAR_SURFACE_AREA>
38.77

> <JCHEM_REFRACTIVITY>
96.706

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.55e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E,8E)-9-(2H-1,3-benzodioxol-5-yl)-1-(pyrrolidin-1-yl)nona-2,8-dien-1-one

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0302866
     RDKit          3D
2-trans-8-trans-Piperamide-C-9-2
 49 51  0  0  0  0  0  0  0  0999 V2000
   -5.1715    2.2018   -1.2237 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8186    1.1218   -0.5658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4306    0.8957   -0.3505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8916   -0.1013    0.2703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4076   -0.2469    0.4436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6813    0.8962   -0.1890 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8201    0.7524   -0.0155 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3509   -0.4952   -0.6318 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8239   -0.5585   -0.4137 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5329    0.3399    0.2255 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9577    0.2897    0.4427 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5955    1.3055    1.1369 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9485    1.3267    1.3828 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7224    0.2840    0.9168 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1336   -0.7432    0.2249 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7442   -0.7359   -0.0111 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1192   -1.6430   -0.1210 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3423   -0.9409   -0.1187 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0942   -0.0323    0.9708 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9087    0.3388   -0.1682 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3338    0.7091   -0.4686 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.5288   -2.3858    0.6098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8046   -0.9299    1.6168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5527   -0.8312    1.5995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4531   -1.7393    0.0030 H   0  0  0  0  0  0  0  0  0  0  0  0
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 12 37  1  0
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 24 48  1  0
 24 49  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      14.119   8.485   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.450   8.485   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.116   7.715   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.116   6.175   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.782   5.405   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.551   6.175   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -2.016   5.699   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -2.921   6.945   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -2.016   8.191   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -0.551   7.715   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.782   8.485   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0      15.607   8.087   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0      16.804   9.056   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      18.095   8.217   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      17.696   6.730   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      16.159   6.649   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.783   7.715   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.117   8.485   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.451   7.715   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.784   8.485   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.118   7.715   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.452   8.485   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.786   7.715   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      13.918  10.012   0.000  0.00  0.00           O+0
CONECT    1   12   23   24                                                  
CONECT    2    3   17                                                       
CONECT    3    2    4   11                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   10                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    6   11                                                  
CONECT   11   10    3                                                       
CONECT   12    1   13   16                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   12                                                       
CONECT   17    2   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22    1                                                       
CONECT   24    1                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

COMPND    HMDB0302866
HETATM    1  O1  UNL     1      -5.172   2.202  -1.224  1.00  0.00           O  
HETATM    2  C1  UNL     1      -4.819   1.122  -0.566  1.00  0.00           C  
HETATM    3  C2  UNL     1      -3.431   0.896  -0.350  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.892  -0.101   0.270  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.408  -0.247   0.444  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.681   0.896  -0.189  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.820   0.752  -0.015  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.351  -0.495  -0.632  1.00  0.00           C  
HETATM    9  C8  UNL     1       2.824  -0.559  -0.414  1.00  0.00           C  
HETATM   10  C9  UNL     1       3.533   0.340   0.225  1.00  0.00           C  
HETATM   11  C10 UNL     1       4.958   0.290   0.443  1.00  0.00           C  
HETATM   12  C11 UNL     1       5.596   1.305   1.137  1.00  0.00           C  
HETATM   13  C12 UNL     1       6.948   1.327   1.383  1.00  0.00           C  
HETATM   14  C13 UNL     1       7.722   0.284   0.917  1.00  0.00           C  
HETATM   15  C14 UNL     1       7.134  -0.743   0.225  1.00  0.00           C  
HETATM   16  C15 UNL     1       5.744  -0.736  -0.011  1.00  0.00           C  
HETATM   17  O2  UNL     1       8.119  -1.643  -0.121  1.00  0.00           O  
HETATM   18  C16 UNL     1       9.342  -0.941  -0.119  1.00  0.00           C  
HETATM   19  O3  UNL     1       9.094  -0.032   0.971  1.00  0.00           O  
HETATM   20  N1  UNL     1      -5.909   0.339  -0.168  1.00  0.00           N  
HETATM   21  C17 UNL     1      -7.334   0.709  -0.469  1.00  0.00           C  
HETATM   22  C18 UNL     1      -7.996  -0.655  -0.541  1.00  0.00           C  
HETATM   23  C19 UNL     1      -7.400  -1.304   0.675  1.00  0.00           C  
HETATM   24  C20 UNL     1      -5.923  -0.892   0.554  1.00  0.00           C  
HETATM   25  H1  UNL     1      -2.695   1.653  -0.754  1.00  0.00           H  
HETATM   26  H2  UNL     1      -3.477  -0.881   0.697  1.00  0.00           H  
HETATM   27  H3  UNL     1      -1.108  -1.226   0.061  1.00  0.00           H  
HETATM   28  H4  UNL     1      -1.207  -0.232   1.535  1.00  0.00           H  
HETATM   29  H5  UNL     1      -0.855   0.961  -1.280  1.00  0.00           H  
HETATM   30  H6  UNL     1      -0.982   1.832   0.329  1.00  0.00           H  
HETATM   31  H7  UNL     1       1.064   0.754   1.064  1.00  0.00           H  
HETATM   32  H8  UNL     1       1.353   1.627  -0.471  1.00  0.00           H  
HETATM   33  H9  UNL     1       1.147  -0.598  -1.702  1.00  0.00           H  
HETATM   34  H10 UNL     1       0.929  -1.392  -0.128  1.00  0.00           H  
HETATM   35  H11 UNL     1       3.374  -1.426  -0.818  1.00  0.00           H  
HETATM   36  H12 UNL     1       2.987   1.196   0.625  1.00  0.00           H  
HETATM   37  H13 UNL     1       5.000   2.144   1.516  1.00  0.00           H  
HETATM   38  H14 UNL     1       7.419   2.139   1.931  1.00  0.00           H  
HETATM   39  H15 UNL     1       5.328  -1.566  -0.560  1.00  0.00           H  
HETATM   40  H16 UNL     1      10.212  -1.577   0.087  1.00  0.00           H  
HETATM   41  H17 UNL     1       9.408  -0.395  -1.082  1.00  0.00           H  
HETATM   42  H18 UNL     1      -7.730   1.341   0.324  1.00  0.00           H  
HETATM   43  H19 UNL     1      -7.347   1.200  -1.451  1.00  0.00           H  
HETATM   44  H20 UNL     1      -7.618  -1.187  -1.431  1.00  0.00           H  
HETATM   45  H21 UNL     1      -9.084  -0.595  -0.524  1.00  0.00           H  
HETATM   46  H22 UNL     1      -7.529  -2.386   0.610  1.00  0.00           H  
HETATM   47  H23 UNL     1      -7.805  -0.930   1.617  1.00  0.00           H  
HETATM   48  H24 UNL     1      -5.553  -0.831   1.599  1.00  0.00           H  
HETATM   49  H25 UNL     1      -5.453  -1.739   0.003  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   20
CONECT    3    4    4   25
CONECT    4    5   26
CONECT    5    6   27   28
CONECT    6    7   29   30
CONECT    7    8   31   32
CONECT    8    9   33   34
CONECT    9   10   10   35
CONECT   10   11   36
CONECT   11   12   12   16
CONECT   12   13   37
CONECT   13   14   14   38
CONECT   14   15   19
CONECT   15   16   16   17
CONECT   16   39
CONECT   17   18
CONECT   18   19   40   41
CONECT   20   21   24
CONECT   21   22   42   43
CONECT   22   23   44   45
CONECT   23   24   46   47
CONECT   24   48   49
END

HMDB0302866
     RDKit          3D
2-trans-8-trans-Piperamide-C-9-2
 49 51  0  0  0  0  0  0  0  0999 V2000
   -5.1715    2.2018   -1.2237 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8186    1.1218   -0.5658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4306    0.8957   -0.3505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8916   -0.1013    0.2703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4076   -0.2469    0.4436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6813    0.8962   -0.1890 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8201    0.7524   -0.0155 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3509   -0.4952   -0.6318 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8239   -0.5585   -0.4137 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5329    0.3399    0.2255 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9577    0.2897    0.4427 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5955    1.3055    1.1369 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9485    1.3267    1.3828 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7224    0.2840    0.9168 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1336   -0.7432    0.2249 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7442   -0.7359   -0.0111 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1192   -1.6430   -0.1210 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3423   -0.9409   -0.1187 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0942   -0.0323    0.9708 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9087    0.3388   -0.1682 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3338    0.7091   -0.4686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9963   -0.6548   -0.5415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4004   -1.3035    0.6751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9227   -0.8917    0.5541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6950    1.6526   -0.7542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4773   -0.8807    0.6967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1078   -1.2259    0.0613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2074   -0.2321    1.5347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8554    0.9614   -1.2803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9815    1.8319    0.3286 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0638    0.7542    1.0636 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3529    1.6274   -0.4708 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1475   -0.5980   -1.7020 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9286   -1.3922   -0.1278 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3736   -1.4265   -0.8178 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9870    1.1963    0.6247 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9995    2.1440    1.5161 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4191    2.1386    1.9308 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3283   -1.5660   -0.5600 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2121   -1.5767    0.0873 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4082   -0.3954   -1.0819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7300    1.3407    0.3238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3471    1.2003   -1.4513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6178   -1.1868   -1.4310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0843   -0.5953   -0.5236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5288   -2.3858    0.6098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8046   -0.9299    1.6168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5527   -0.8312    1.5995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4531   -1.7393    0.0030 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  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
  2 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 16 11  1  0
 24 20  1  0
 19 14  1  0
  3 25  1  0
  4 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
  7 32  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  0
 10 36  1  0
 12 37  1  0
 13 38  1  0
 16 39  1  0
 18 40  1  0
 18 41  1  0
 21 42  1  0
 21 43  1  0
 22 44  1  0
 22 45  1  0
 23 46  1  0
 23 47  1  0
 24 48  1  0
 24 49  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₂₀H₂₅NO₃

Average Molecular Weight

327.4174

Monoisotopic Molecular Weight

327.183443671

IUPAC Name

(2E,8E)-9-(2H-1,3-benzodioxol-5-yl)-1-(pyrrolidin-1-yl)nona-2,8-dien-1-one

Traditional Name

(2E,8E)-9-(2H-1,3-benzodioxol-5-yl)-1-(pyrrolidin-1-yl)nona-2,8-dien-1-one

CAS Registry Number

Not Available

SMILES

O=C(\C=C\CCCC\C=C\C1=CC=C2OCOC2=C1)N1CCCC1

InChI Identifier

InChI=1S/C20H25NO3/c22-20(21-13-7-8-14-21)10-6-4-2-1-3-5-9-17-11-12-18-19(15-17)24-16-23-18/h5-6,9-12,15H,1-4,7-8,13-14,16H2/b9-5+,10-6+

InChI Key

BYKNKNBUHGFXQF-NXZHAISVSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzodioxoles. These are organic compounds containing a benzene ring fused to either isomers of dioxole. Dioxole is a five-membered unsaturated ring of two oxygen atoms and three carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzodioxoles

Sub Class

Not Available

Direct Parent

Benzodioxoles

Alternative Parents

Substituents

Benzodioxole
N-acylpyrrolidine
Styrene
Benzenoid
Pyrrolidine
Tertiary carboxylic acid amide
Carboxamide group
Acetal
Carboxylic acid derivative
Oxacycle
Azacycle
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organic nitrogen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

benzodioxoles (CHEBI:70096 )

Ontology

Not Available

Exogenous (HMDB: HMDB0302866)

Food

Herb and spice

Spice

Pepper (Spice) (FooDB: FOOD00139)

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	4.49	ALOGPS
logP	4.11	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Basic)	2.17	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	38.77 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	96.71 m³·mol⁻¹	ChemAxon
Polarizability	38.59 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]+	182.731	32859911
AllCCS	[M+H-H2O]+	179.482	32859911
AllCCS	[M+Na]+	186.604	32859911
AllCCS	[M+NH4]+	185.74	32859911
AllCCS	[M-H]-	185.695	32859911
AllCCS	[M+Na-2H]-	186.107	32859911
AllCCS	[M+HCOO]-	186.71	32859911
DeepCCS	[M+H]+	178.135	30932474
DeepCCS	[M-H]-	175.777	30932474
DeepCCS	[M-2H]-	209.566	30932474
DeepCCS	[M+Na]+	184.819	30932474

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	18.3526 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.13 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2785.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	459.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	229.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	246.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	447.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	792.9 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	782.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	127.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1703.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	553.9 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	1711.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	553.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	461.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	349.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	404.5 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

Not Available

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-trans-8-trans-Piperamide-C-9-2 10V, Positive-QTOF	splash10-004i-3129000000-75276aec8e22abe871d5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-trans-8-trans-Piperamide-C-9-2 20V, Positive-QTOF	splash10-00di-9873000000-99fd950b035b5635d155	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-trans-8-trans-Piperamide-C-9-2 40V, Positive-QTOF	splash10-00di-9110000000-7330f79e6579d4baa229	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-trans-8-trans-Piperamide-C-9-2 10V, Negative-QTOF	splash10-004i-1019000000-266d0c3f83e53dd2cc6b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-trans-8-trans-Piperamide-C-9-2 20V, Negative-QTOF	splash10-00b9-9177000000-c5bec6a8562f15b011a8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-trans-8-trans-Piperamide-C-9-2 40V, Negative-QTOF	splash10-00di-9120000000-1770d2b3fcee52432715	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-trans-8-trans-Piperamide-C-9-2 10V, Positive-QTOF	splash10-004i-0039000000-24e6e045ae7c9f4647ca	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-trans-8-trans-Piperamide-C-9-2 20V, Positive-QTOF	splash10-00fr-7195000000-7a98d0f6337f47ac0408	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-trans-8-trans-Piperamide-C-9-2 40V, Positive-QTOF	splash10-00di-9620000000-733ed85208556583b907	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-trans-8-trans-Piperamide-C-9-2 10V, Negative-QTOF	splash10-004i-0009000000-c190b500bc564229fe0d	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-trans-8-trans-Piperamide-C-9-2 20V, Negative-QTOF	splash10-004i-1029000000-5b3993b2976817baa1ff	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-trans-8-trans-Piperamide-C-9-2 40V, Negative-QTOF	splash10-006t-2965000000-32479a3fa7b64991052c	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

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

FDB006604

KNApSAcK ID

C00055285

Chemspider ID

10192703

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14162526

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

Not Available

Showing metabocard for 2-trans-8-trans-Piperamide-C-9-2 (HMDB0302866)

MOL for HMDB0302866 (2-trans-8-trans-Piperamide-C-9-2)

3D MOL for HMDB0302866 (2-trans-8-trans-Piperamide-C-9-2)

3D SDF for HMDB0302866 (2-trans-8-trans-Piperamide-C-9-2)

3D-SDF for HMDB0302866 (2-trans-8-trans-Piperamide-C-9-2)

PDB for HMDB0302866 (2-trans-8-trans-Piperamide-C-9-2)

3D PDB for HMDB0302866 (2-trans-8-trans-Piperamide-C-9-2)

SMILES for HMDB0302866 (2-trans-8-trans-Piperamide-C-9-2)

INCHI for HMDB0302866 (2-trans-8-trans-Piperamide-C-9-2)

Structure for HMDB0302866 (2-trans-8-trans-Piperamide-C-9-2)

3D Structure for HMDB0302866 (2-trans-8-trans-Piperamide-C-9-2)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

MS/MS Spectra