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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:38:50 UTC

Update Date

2022-03-07 02:53:53 UTC

HMDB ID

HMDB0033874

Secondary Accession Numbers

HMDB33874

Metabolite Identification

Common Name

Piperanine

Description

Piperanine 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. Piperanine has been detected, but not quantified in, herbs and spices and pepper (spice). This could make piperanine a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Piperanine.

Structure

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

HMDB0033874
     RDKit          3D
Piperanine
 42 44  0  0  0  0  0  0  0  0999 V2000
   -0.7268   -2.4137   -1.5571 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9928   -1.5428   -0.5852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2414   -1.8106    0.5773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2051   -1.1945    1.7175 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7043   -1.6829    2.8443 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6439   -0.5470    3.1531 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4361   -0.2127    1.9294 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6361   -0.8487    1.7074 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3587   -0.5299    0.5715 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8932    0.4157   -0.3406 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6858    1.0226   -0.0700 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9342    0.7305    1.0551 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4349    1.9138   -1.1065 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5123    1.9174   -2.0131 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3705    0.9294   -1.5238 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9457   -0.5512   -0.8980 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4812   -0.5928   -2.2571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8211    0.0035   -2.4352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9197    1.3745   -1.7754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5351    1.3034   -0.3412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3854    0.4328    0.0182 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4491   -2.6967    0.5431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7791   -0.3444    1.9193 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2162   -2.6064    2.5508 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0533   -1.8365    3.7271 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0362    0.3144    3.4753 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3315   -0.8509    3.9761 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0280   -1.5924    2.4006 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3033   -1.0250    0.3887 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9879    1.2351    1.2257 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0935    1.6679   -3.0114 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9838    2.9189   -2.0767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7084   -0.1756   -2.9375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5567   -1.6806   -2.5508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6317   -0.6463   -2.0990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9740    0.1837   -3.5191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9853    1.6762   -1.8456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3261    2.1280   -2.3369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2442    2.3591   -0.0473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4217    1.1000    0.3109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4798    1.0361    0.2890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7319   -0.1390    0.9470 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  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
  2 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 12  7  1  0
 21 16  1  0
 15 10  1  0
  3 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  6 26  1  0
  6 27  1  0
  8 28  1  0
  9 29  1  0
 12 30  1  0
 14 31  1  0
 14 32  1  0
 17 33  1  0
 17 34  1  0
 18 35  1  0
 18 36  1  0
 19 37  1  0
 19 38  1  0
 20 39  1  0
 20 40  1  0
 21 41  1  0
 21 42  1  0
M  END

  Mrv0541 02241208082D          

 21 23  0  0  0  0            999 V2000
   -2.9358   -0.8252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9358    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7211    0.2558    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2080   -0.4126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7211   -1.0824    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2220   -1.2378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5094   -0.8252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5094    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2220    0.4112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7942    0.4112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0790    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6362    0.4112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3514    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0666    0.4112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7818    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0666    1.2378    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7818   -0.8252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4956   -1.2378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2080   -0.8252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2080    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4956    0.4112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  5  1  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  2  9  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  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  1  0  0  0  0
 14 16  2  0  0  0  0
 15 17  1  0  0  0  0
 15 21  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033874

> <DATABASE_NAME>
hmdb

> <SMILES>
O=C(\C=C\CCC1=CC2=C(OCO2)C=C1)N1CCCCC1

> <INCHI_IDENTIFIER>
InChI=1S/C17H21NO3/c19-17(18-10-4-1-5-11-18)7-3-2-6-14-8-9-15-16(12-14)21-13-20-15/h3,7-9,12H,1-2,4-6,10-11,13H2/b7-3+

> <INCHI_KEY>
QHWOFMXDKFORMO-XVNBXDOJSA-N

> <FORMULA>
C17H21NO3

> <MOLECULAR_WEIGHT>
287.3535

> <EXACT_MASS>
287.152143543

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
32.72132058897919

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-5-(2H-1,3-benzodioxol-5-yl)-1-(piperidin-1-yl)pent-2-en-1-one

> <ALOGPS_LOGP>
3.48

> <JCHEM_LOGP>
3.0565327070000006

> <ALOGPS_LOGS>
-3.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
2.4709512561866833

> <JCHEM_POLAR_SURFACE_AREA>
38.77

> <JCHEM_REFRACTIVITY>
81.7864

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.61e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-5-(2H-1,3-benzodioxol-5-yl)-1-(piperidin-1-yl)pent-2-en-1-one

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0033874
     RDKit          3D
Piperanine
 42 44  0  0  0  0  0  0  0  0999 V2000
   -0.7268   -2.4137   -1.5571 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9928   -1.5428   -0.5852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2414   -1.8106    0.5773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2051   -1.1945    1.7175 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7043   -1.6829    2.8443 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6439   -0.5470    3.1531 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4361   -0.2127    1.9294 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6361   -0.8487    1.7074 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3587   -0.5299    0.5715 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8932    0.4157   -0.3406 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6858    1.0226   -0.0700 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9342    0.7305    1.0551 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4349    1.9138   -1.1065 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5123    1.9174   -2.0131 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3705    0.9294   -1.5238 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9457   -0.5512   -0.8980 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4812   -0.5928   -2.2571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8211    0.0035   -2.4352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9197    1.3745   -1.7754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5351    1.3034   -0.3412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3854    0.4328    0.0182 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4491   -2.6967    0.5431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7791   -0.3444    1.9193 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2162   -2.6064    2.5508 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0533   -1.8365    3.7271 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0362    0.3144    3.4753 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3315   -0.8509    3.9761 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0280   -1.5924    2.4006 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3033   -1.0250    0.3887 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9879    1.2351    1.2257 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0935    1.6679   -3.0114 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9838    2.9189   -2.0767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7084   -0.1756   -2.9375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5567   -1.6806   -2.5508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6317   -0.6463   -2.0990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9740    0.1837   -3.5191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9853    1.6762   -1.8456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3261    2.1280   -2.3369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2442    2.3591   -0.0473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4217    1.1000    0.3109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4798    1.0361    0.2890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7319   -0.1390    0.9470 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  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
  2 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 12  7  1  0
 21 16  1  0
 15 10  1  0
  3 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  6 26  1  0
  6 27  1  0
  8 28  1  0
  9 29  1  0
 12 30  1  0
 14 31  1  0
 14 32  1  0
 17 33  1  0
 17 34  1  0
 18 35  1  0
 18 36  1  0
 19 37  1  0
 19 38  1  0
 20 39  1  0
 20 40  1  0
 21 41  1  0
 21 42  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      -5.480  -1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.480   0.000   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -6.946   0.477   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -7.855  -0.770   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -6.946  -2.020   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -4.148  -2.311   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.818  -1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.818   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.148   0.768   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.483   0.768   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.147   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.188   0.768   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.523   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.858   0.768   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       5.193   0.000   0.000  0.00  0.00           N+0
HETATM   16  O   UNK     0       3.858   2.311   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       5.193  -1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.525  -2.311   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.855  -1.540   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.855   0.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.525   0.768   0.000  0.00  0.00           C+0
CONECT    1    2    5    6                                                  
CONECT    2    1    3    9                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    1    4                                                       
CONECT    6    1    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    2    8                                                       
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14   17   21                                                  
CONECT   16   14                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   15   20                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    HMDB0033874
HETATM    1  O1  UNL     1      -0.727  -2.414  -1.557  1.00  0.00           O  
HETATM    2  C1  UNL     1      -0.993  -1.543  -0.585  1.00  0.00           C  
HETATM    3  C2  UNL     1      -0.241  -1.811   0.577  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.205  -1.194   1.718  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.704  -1.683   2.844  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.644  -0.547   3.153  1.00  0.00           C  
HETATM    7  C6  UNL     1       2.436  -0.213   1.929  1.00  0.00           C  
HETATM    8  C7  UNL     1       3.636  -0.849   1.707  1.00  0.00           C  
HETATM    9  C8  UNL     1       4.359  -0.530   0.572  1.00  0.00           C  
HETATM   10  C9  UNL     1       3.893   0.416  -0.341  1.00  0.00           C  
HETATM   11  C10 UNL     1       2.686   1.023  -0.070  1.00  0.00           C  
HETATM   12  C11 UNL     1       1.934   0.731   1.055  1.00  0.00           C  
HETATM   13  O2  UNL     1       2.435   1.914  -1.107  1.00  0.00           O  
HETATM   14  C12 UNL     1       3.512   1.917  -2.013  1.00  0.00           C  
HETATM   15  O3  UNL     1       4.370   0.929  -1.524  1.00  0.00           O  
HETATM   16  N1  UNL     1      -1.946  -0.551  -0.898  1.00  0.00           N  
HETATM   17  C13 UNL     1      -2.481  -0.593  -2.257  1.00  0.00           C  
HETATM   18  C14 UNL     1      -3.821   0.003  -2.435  1.00  0.00           C  
HETATM   19  C15 UNL     1      -3.920   1.374  -1.775  1.00  0.00           C  
HETATM   20  C16 UNL     1      -3.535   1.303  -0.341  1.00  0.00           C  
HETATM   21  C17 UNL     1      -2.385   0.433   0.018  1.00  0.00           C  
HETATM   22  H1  UNL     1       0.449  -2.697   0.543  1.00  0.00           H  
HETATM   23  H2  UNL     1      -0.779  -0.344   1.919  1.00  0.00           H  
HETATM   24  H3  UNL     1       1.216  -2.606   2.551  1.00  0.00           H  
HETATM   25  H4  UNL     1       0.053  -1.837   3.727  1.00  0.00           H  
HETATM   26  H5  UNL     1       1.036   0.314   3.475  1.00  0.00           H  
HETATM   27  H6  UNL     1       2.331  -0.851   3.976  1.00  0.00           H  
HETATM   28  H7  UNL     1       4.028  -1.592   2.401  1.00  0.00           H  
HETATM   29  H8  UNL     1       5.303  -1.025   0.389  1.00  0.00           H  
HETATM   30  H9  UNL     1       0.988   1.235   1.226  1.00  0.00           H  
HETATM   31  H10 UNL     1       3.094   1.668  -3.011  1.00  0.00           H  
HETATM   32  H11 UNL     1       3.984   2.919  -2.077  1.00  0.00           H  
HETATM   33  H12 UNL     1      -1.708  -0.176  -2.938  1.00  0.00           H  
HETATM   34  H13 UNL     1      -2.557  -1.681  -2.551  1.00  0.00           H  
HETATM   35  H14 UNL     1      -4.632  -0.646  -2.099  1.00  0.00           H  
HETATM   36  H15 UNL     1      -3.974   0.184  -3.519  1.00  0.00           H  
HETATM   37  H16 UNL     1      -4.985   1.676  -1.846  1.00  0.00           H  
HETATM   38  H17 UNL     1      -3.326   2.128  -2.337  1.00  0.00           H  
HETATM   39  H18 UNL     1      -3.244   2.359  -0.047  1.00  0.00           H  
HETATM   40  H19 UNL     1      -4.422   1.100   0.311  1.00  0.00           H  
HETATM   41  H20 UNL     1      -1.480   1.036   0.289  1.00  0.00           H  
HETATM   42  H21 UNL     1      -2.732  -0.139   0.947  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   16
CONECT    3    4    4   22
CONECT    4    5   23
CONECT    5    6   24   25
CONECT    6    7   26   27
CONECT    7    8    8   12
CONECT    8    9   28
CONECT    9   10   10   29
CONECT   10   11   15
CONECT   11   12   12   13
CONECT   12   30
CONECT   13   14
CONECT   14   15   31   32
CONECT   16   17   21
CONECT   17   18   33   34
CONECT   18   19   35   36
CONECT   19   20   37   38
CONECT   20   21   39   40
CONECT   21   41   42
END

HMDB0033874
     RDKit          3D
Piperanine
 42 44  0  0  0  0  0  0  0  0999 V2000
   -0.7268   -2.4137   -1.5571 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9928   -1.5428   -0.5852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2414   -1.8106    0.5773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2051   -1.1945    1.7175 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7043   -1.6829    2.8443 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6439   -0.5470    3.1531 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4361   -0.2127    1.9294 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6361   -0.8487    1.7074 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3587   -0.5299    0.5715 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8932    0.4157   -0.3406 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6858    1.0226   -0.0700 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9342    0.7305    1.0551 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4349    1.9138   -1.1065 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5123    1.9174   -2.0131 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3705    0.9294   -1.5238 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9457   -0.5512   -0.8980 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4812   -0.5928   -2.2571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8211    0.0035   -2.4352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9197    1.3745   -1.7754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5351    1.3034   -0.3412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3854    0.4328    0.0182 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4491   -2.6967    0.5431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7791   -0.3444    1.9193 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2162   -2.6064    2.5508 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0533   -1.8365    3.7271 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0362    0.3144    3.4753 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3315   -0.8509    3.9761 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0280   -1.5924    2.4006 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3033   -1.0250    0.3887 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9879    1.2351    1.2257 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0935    1.6679   -3.0114 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9838    2.9189   -2.0767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7084   -0.1756   -2.9375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5567   -1.6806   -2.5508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6317   -0.6463   -2.0990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9740    0.1837   -3.5191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9853    1.6762   -1.8456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3261    2.1280   -2.3369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2442    2.3591   -0.0473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4217    1.1000    0.3109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4798    1.0361    0.2890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7319   -0.1390    0.9470 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  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
  2 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 12  7  1  0
 21 16  1  0
 15 10  1  0
  3 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  6 26  1  0
  6 27  1  0
  8 28  1  0
  9 29  1  0
 12 30  1  0
 14 31  1  0
 14 32  1  0
 17 33  1  0
 17 34  1  0
 18 35  1  0
 18 36  1  0
 19 37  1  0
 19 38  1  0
 20 39  1  0
 20 40  1  0
 21 41  1  0
 21 42  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Delata-Alpha	ChEMBL, HMDB
Beta-Dihydropiperine	ChEMBL, HMDB
Dalpha	ChEMBL, HMDB
Delata-a	Generator, HMDB
Delata-α	Generator, HMDB
b-Dihydropiperine	Generator, HMDB
β-dihydropiperine	Generator, HMDB
1-[5-(1,3-Benzodioxol-5-yl)-1-oxo-2-pentenyl]piperidine	HMDB
5-(3,4-Methylenedioxyphenyl)-2-pentenoic acid piperidide	HMDB
b-Hydropiperylpiperidine	HMDB
Da,b-dihydropiperine	HMDB

Chemical Formula

C₁₇H₂₁NO₃

Average Molecular Weight

287.3535

Monoisotopic Molecular Weight

287.152143543

IUPAC Name

(2E)-5-(2H-1,3-benzodioxol-5-yl)-1-(piperidin-1-yl)pent-2-en-1-one

Traditional Name

(2E)-5-(2H-1,3-benzodioxol-5-yl)-1-(piperidin-1-yl)pent-2-en-1-one

CAS Registry Number

23512-46-1

SMILES

O=C(\C=C\CCC1=CC2=C(OCO2)C=C1)N1CCCCC1

InChI Identifier

InChI=1S/C17H21NO3/c19-17(18-10-4-1-5-11-18)7-3-2-6-14-8-9-15-16(12-14)21-13-20-15/h3,7-9,12H,1-2,4-6,10-11,13H2/b7-3+

InChI Key

QHWOFMXDKFORMO-XVNBXDOJSA-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-acyl-piperidine
Piperidine
Benzenoid
Tertiary carboxylic acid amide
Carboxamide group
Azacycle
Carboxylic acid derivative
Acetal
Oxacycle
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Carbonyl group
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0033874)
Cell membrane (HMDB: HMDB0033874)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033874)

Source

Exogenous

Exogenous (HMDB: HMDB0033874)

Food

Food (HMDB: HMDB0033874)

Herb and spice

Spice

Pepper (Spice) (FooDB: FOOD00139)

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Plant

Plant (HMDB: HMDB0033874)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0033874)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	79 - 80 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	6.74 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.16 g/L	ALOGPS
logP	3.48	ALOGPS
logP	3.06	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Basic)	2.47	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	4	ChemAxon
Refractivity	81.79 m³·mol⁻¹	ChemAxon
Polarizability	32.72 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	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	169.501	31661259
DarkChem	[M-H]-	170.171	31661259
DeepCCS	[M+H]+	165.505	30932474
DeepCCS	[M-H]-	163.123	30932474
DeepCCS	[M-2H]-	196.159	30932474
DeepCCS	[M+Na]+	171.574	30932474
AllCCS	[M+H]+	169.6	32859911
AllCCS	[M+H-H2O]+	166.1	32859911
AllCCS	[M+NH4]+	172.9	32859911
AllCCS	[M+Na]+	173.8	32859911
AllCCS	[M-H]-	174.0	32859911
AllCCS	[M+Na-2H]-	174.0	32859911
AllCCS	[M+HCOO]-	174.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Piperanine	O=C(\C=C\CCC1=CC2=C(OCO2)C=C1)N1CCCCC1	3667.3	Standard polar	33892256
Piperanine	O=C(\C=C\CCC1=CC2=C(OCO2)C=C1)N1CCCCC1	2343.6	Standard non polar	33892256
Piperanine	O=C(\C=C\CCC1=CC2=C(OCO2)C=C1)N1CCCCC1	2634.2	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 - Piperanine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f79-3950000000-bcd7117a5db53c825b49	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Piperanine 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Piperanine LC-ESI-qTof , Positive-QTOF	splash10-067i-0900000000-501111d1497bebd73175	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Piperanine , positive-QTOF	splash10-000i-0910000000-02c27ecc1fbd16661431	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Piperanine , positive-QTOF	splash10-000i-0910000000-6c87b10e6d03efc37120	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperanine 10V, Positive-QTOF	splash10-000i-2290000000-50752c83b7a1b2c76931	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperanine 20V, Positive-QTOF	splash10-000i-6960000000-4f522a781663933a605f	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperanine 40V, Positive-QTOF	splash10-052r-9300000000-a48b20e34a96fc77a1a8	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperanine 10V, Negative-QTOF	splash10-000i-0090000000-a6c24185982a09c089f3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperanine 20V, Negative-QTOF	splash10-001r-5490000000-b721e5b0b0d32bc8f89b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperanine 40V, Negative-QTOF	splash10-001i-9310000000-8edaeb5f6a0de61f4f87	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperanine 10V, Positive-QTOF	splash10-000i-0090000000-3724bfaaf393a959b2f8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperanine 20V, Positive-QTOF	splash10-000i-1490000000-b8e8c9fb7b120dedf357	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperanine 40V, Positive-QTOF	splash10-01sr-4920000000-be8efcea844fe5793c15	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperanine 10V, Negative-QTOF	splash10-000i-0090000000-32affc6af32f5da1d257	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperanine 20V, Negative-QTOF	splash10-000i-0290000000-28e9199aca5bd12b6b59	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperanine 40V, Negative-QTOF	splash10-001i-2590000000-8e9636d54485b7ff8113	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

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

FDB012066

KNApSAcK ID

Not Available

Chemspider ID

4478657

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5320618

PDB ID

Not Available

ChEBI ID

167837

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1629081

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Piperanine (HMDB0033874)

MOL for HMDB0033874 (Piperanine)

3D MOL for HMDB0033874 (Piperanine)

3D SDF for HMDB0033874 (Piperanine)

3D-SDF for HMDB0033874 (Piperanine)

PDB for HMDB0033874 (Piperanine)

3D PDB for HMDB0033874 (Piperanine)

SMILES for HMDB0033874 (Piperanine)

INCHI for HMDB0033874 (Piperanine)

Structure for HMDB0033874 (Piperanine)

3D Structure for HMDB0033874 (Piperanine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra