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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 19:11:43 UTC

Update Date

2022-03-07 02:54:04 UTC

HMDB ID

HMDB0034371

Secondary Accession Numbers

HMDB34371

Metabolite Identification

Common Name

Piperettine

Description

Piperettine 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. Piperettine is found, on average, in the highest concentration within pepper (spice). Piperettine has also been detected, but not quantified in, herbs and spices. This could make piperettine a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Piperettine.

Structure

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

HMDB0034371
     RDKit          3D
Piperettine
 44 46  0  0  0  0  0  0  0  0999 V2000
   -4.4170    2.5387    1.2504 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7821    1.4576    0.8158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3873    1.6094    0.7029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4893    0.7064    0.3805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0894    1.0692    0.3037 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8542    0.1338   -0.0349 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2058    0.5330   -0.1026 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3578    0.8723   -0.1605 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6548    0.3357   -0.4737 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8446   -0.9716   -0.8111 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0966   -1.5180   -1.0997 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1855   -0.6811   -1.0345 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0583    0.6452   -0.7029 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7842    1.1293   -0.4263 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3187    1.2088   -0.7322 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2660    0.1553   -0.6918 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5481   -0.9334   -1.2609 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6790    0.3854    0.5637 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3078   -0.8483   -0.0612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4305   -1.6068   -0.6654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7498   -1.5471    0.0138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1229   -0.1249    0.3759 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0294    0.5953    1.0430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9565    2.6245    0.9065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8048   -0.3011    0.2057 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2578    2.0671    0.5057 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4044   -0.8207   -0.2069 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5654   -0.7486   -0.5142 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4473    2.0039    0.1489 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0360   -1.6917   -0.8777 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1391   -2.5477   -1.3531 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6955    2.1607   -0.1762 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4688   -0.0917    0.3762 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1629    0.3159   -1.2798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6126   -0.6438   -0.9456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8084   -1.4752    0.7058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5388   -1.4039   -1.7845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1361   -2.7084   -0.6845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7746   -2.2297    0.8902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5281   -1.9147   -0.6924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5085    0.4250   -0.4765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9766   -0.2452    1.1081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2545    1.7025    0.9236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9676    0.3789    2.1423 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  2  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
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
  2 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 14  9  1  0
 23 18  1  0
 17 12  1  0
  3 24  1  0
  4 25  1  0
  5 26  1  0
  6 27  1  0
  7 28  1  0
  8 29  1  0
 10 30  1  0
 11 31  1  0
 14 32  1  0
 16 33  1  0
 16 34  1  0
 19 35  1  0
 19 36  1  0
 20 37  1  0
 20 38  1  0
 21 39  1  0
 21 40  1  0
 22 41  1  0
 22 42  1  0
 23 43  1  0
 23 44  1  0
M  END

  Mrv0541 05061307462D          

 23 25  0  0  0  0            999 V2000
    6.1368   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1368   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5658   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8513   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2802   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8513   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8513   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2802   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8513   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5658   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5658   -3.7125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2802   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  4  1  1  0  0  0  0
  5  2  1  0  0  0  0
  6  3  1  0  0  0  0
  7  3  1  0  0  0  0
  8  4  2  0  0  0  0
  9  5  2  0  0  0  0
 11 10  2  0  0  0  0
 12  6  1  0  0  0  0
 13  7  1  0  0  0  0
 16  8  1  0  0  0  0
 16 10  1  0  0  0  0
 16 14  2  0  0  0  0
 17 11  1  0  0  0  0
 18 14  1  0  0  0  0
 18 17  2  0  0  0  0
 19  9  1  0  0  0  0
 20 12  1  0  0  0  0
 20 13  1  0  0  0  0
 20 19  1  0  0  0  0
 21 19  2  0  0  0  0
 22 15  1  0  0  0  0
 22 17  1  0  0  0  0
 23 15  1  0  0  0  0
 23 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0034371

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C19H21NO3/c21-19(20-12-6-3-7-13-20)9-5-2-1-4-8-16-10-11-17-18(14-16)23-15-22-17/h1-2,4-5,8-11,14H,3,6-7,12-13,15H2/b2-1+,8-4+,9-5+

> <INCHI_KEY>
DLKOUKNODPCIHZ-UMYWTXKFSA-N

> <FORMULA>
C19H21NO3

> <MOLECULAR_WEIGHT>
311.3749

> <EXACT_MASS>
311.152143543

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
36.043483489414854

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E,4E,6E)-7-(2H-1,3-benzodioxol-5-yl)-1-(piperidin-1-yl)hepta-2,4,6-trien-1-one

> <ALOGPS_LOGP>
4.03

> <JCHEM_LOGP>
3.3045267236666667

> <ALOGPS_LOGS>
-4.36

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
2.3685199525885285

> <JCHEM_POLAR_SURFACE_AREA>
38.77

> <JCHEM_REFRACTIVITY>
93.2216

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.34e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E,4E,6E)-7-(2H-1,3-benzodioxol-5-yl)-1-(piperidin-1-yl)hepta-2,4,6-trien-1-one

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0034371
     RDKit          3D
Piperettine
 44 46  0  0  0  0  0  0  0  0999 V2000
   -4.4170    2.5387    1.2504 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7821    1.4576    0.8158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3873    1.6094    0.7029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4893    0.7064    0.3805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0894    1.0692    0.3037 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8542    0.1338   -0.0349 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2058    0.5330   -0.1026 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3578    0.8723   -0.1605 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6548    0.3357   -0.4737 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8446   -0.9716   -0.8111 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0966   -1.5180   -1.0997 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1855   -0.6811   -1.0345 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0583    0.6452   -0.7029 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7842    1.1293   -0.4263 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3187    1.2088   -0.7322 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2660    0.1553   -0.6918 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5481   -0.9334   -1.2609 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6790    0.3854    0.5637 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3078   -0.8483   -0.0612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4305   -1.6068   -0.6654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7498   -1.5471    0.0138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1229   -0.1249    0.3759 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0294    0.5953    1.0430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9565    2.6245    0.9065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8048   -0.3011    0.2057 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2578    2.0671    0.5057 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4044   -0.8207   -0.2069 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5654   -0.7486   -0.5142 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4473    2.0039    0.1489 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0360   -1.6917   -0.8777 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1391   -2.5477   -1.3531 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6955    2.1607   -0.1762 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4688   -0.0917    0.3762 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1629    0.3159   -1.2798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6126   -0.6438   -0.9456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8084   -1.4752    0.7058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5388   -1.4039   -1.7845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1361   -2.7084   -0.6845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7746   -2.2297    0.8902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5281   -1.9147   -0.6924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5085    0.4250   -0.4765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9766   -0.2452    1.1081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2545    1.7025    0.9236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9676    0.3789    2.1423 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  2  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
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
  2 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 14  9  1  0
 23 18  1  0
 17 12  1  0
  3 24  1  0
  4 25  1  0
  5 26  1  0
  6 27  1  0
  7 28  1  0
  8 29  1  0
 10 30  1  0
 11 31  1  0
 14 32  1  0
 16 33  1  0
 16 34  1  0
 19 35  1  0
 19 36  1  0
 20 37  1  0
 20 38  1  0
 21 39  1  0
 21 40  1  0
 22 41  1  0
 22 42  1  0
 23 43  1  0
 23 44  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      11.455  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.455  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      14.123 -10.010   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.122   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.789  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      15.456  -9.240   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.789  -9.240   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.788  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.789  -4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      15.456  -7.700   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.789  -7.700   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.454   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      14.123  -5.390   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0      14.123  -6.930   0.000  0.00  0.00           N+0
HETATM   21  O   UNK     0      15.456  -4.620   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       3.322   2.016   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       3.322  -0.476   0.000  0.00  0.00           O+0
CONECT    1    2    4                                                       
CONECT    2    1    5                                                       
CONECT    3    6    7                                                       
CONECT    4    1    8                                                       
CONECT    5    2    9                                                       
CONECT    6    3   12                                                       
CONECT    7    3   13                                                       
CONECT    8    4   16                                                       
CONECT    9    5   19                                                       
CONECT   10   11   16                                                       
CONECT   11   10   17                                                       
CONECT   12    6   20                                                       
CONECT   13    7   20                                                       
CONECT   14   16   18                                                       
CONECT   15   22   23                                                       
CONECT   16    8   10   14                                                  
CONECT   17   11   18   22                                                  
CONECT   18   14   17   23                                                  
CONECT   19    9   20   21                                                  
CONECT   20   12   13   19                                                  
CONECT   21   19                                                            
CONECT   22   15   17                                                       
CONECT   23   15   18                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

COMPND    HMDB0034371
HETATM    1  O1  UNL     1      -4.417   2.539   1.250  1.00  0.00           O  
HETATM    2  C1  UNL     1      -3.782   1.458   0.816  1.00  0.00           C  
HETATM    3  C2  UNL     1      -2.387   1.609   0.703  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.489   0.706   0.380  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.089   1.069   0.304  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.854   0.134  -0.035  1.00  0.00           C  
HETATM    7  C6  UNL     1       2.206   0.533  -0.103  1.00  0.00           C  
HETATM    8  C7  UNL     1       3.358   0.872  -0.161  1.00  0.00           C  
HETATM    9  C8  UNL     1       4.655   0.336  -0.474  1.00  0.00           C  
HETATM   10  C9  UNL     1       4.845  -0.972  -0.811  1.00  0.00           C  
HETATM   11  C10 UNL     1       6.097  -1.518  -1.100  1.00  0.00           C  
HETATM   12  C11 UNL     1       7.185  -0.681  -1.034  1.00  0.00           C  
HETATM   13  C12 UNL     1       7.058   0.645  -0.703  1.00  0.00           C  
HETATM   14  C13 UNL     1       5.784   1.129  -0.426  1.00  0.00           C  
HETATM   15  O2  UNL     1       8.319   1.209  -0.732  1.00  0.00           O  
HETATM   16  C14 UNL     1       9.266   0.155  -0.692  1.00  0.00           C  
HETATM   17  O3  UNL     1       8.548  -0.933  -1.261  1.00  0.00           O  
HETATM   18  N1  UNL     1      -4.679   0.385   0.564  1.00  0.00           N  
HETATM   19  C15 UNL     1      -4.308  -0.848  -0.061  1.00  0.00           C  
HETATM   20  C16 UNL     1      -5.431  -1.607  -0.665  1.00  0.00           C  
HETATM   21  C17 UNL     1      -6.750  -1.547   0.014  1.00  0.00           C  
HETATM   22  C18 UNL     1      -7.123  -0.125   0.376  1.00  0.00           C  
HETATM   23  C19 UNL     1      -6.029   0.595   1.043  1.00  0.00           C  
HETATM   24  H1  UNL     1      -1.957   2.625   0.907  1.00  0.00           H  
HETATM   25  H2  UNL     1      -1.805  -0.301   0.206  1.00  0.00           H  
HETATM   26  H3  UNL     1       0.258   2.067   0.506  1.00  0.00           H  
HETATM   27  H4  UNL     1       0.404  -0.821  -0.207  1.00  0.00           H  
HETATM   28  H5  UNL     1       2.565  -0.749  -0.514  1.00  0.00           H  
HETATM   29  H6  UNL     1       3.447   2.004   0.149  1.00  0.00           H  
HETATM   30  H7  UNL     1       4.036  -1.692  -0.878  1.00  0.00           H  
HETATM   31  H8  UNL     1       6.139  -2.548  -1.353  1.00  0.00           H  
HETATM   32  H9  UNL     1       5.696   2.161  -0.176  1.00  0.00           H  
HETATM   33  H10 UNL     1       9.469  -0.092   0.376  1.00  0.00           H  
HETATM   34  H11 UNL     1      10.163   0.316  -1.280  1.00  0.00           H  
HETATM   35  H12 UNL     1      -3.613  -0.644  -0.946  1.00  0.00           H  
HETATM   36  H13 UNL     1      -3.808  -1.475   0.706  1.00  0.00           H  
HETATM   37  H14 UNL     1      -5.539  -1.404  -1.784  1.00  0.00           H  
HETATM   38  H15 UNL     1      -5.136  -2.708  -0.685  1.00  0.00           H  
HETATM   39  H16 UNL     1      -6.775  -2.230   0.890  1.00  0.00           H  
HETATM   40  H17 UNL     1      -7.528  -1.915  -0.692  1.00  0.00           H  
HETATM   41  H18 UNL     1      -7.508   0.425  -0.477  1.00  0.00           H  
HETATM   42  H19 UNL     1      -7.977  -0.245   1.108  1.00  0.00           H  
HETATM   43  H20 UNL     1      -6.254   1.703   0.924  1.00  0.00           H  
HETATM   44  H21 UNL     1      -5.968   0.379   2.142  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   18
CONECT    3    4    4   24
CONECT    4    5   25
CONECT    5    6    6   26
CONECT    6    7   27
CONECT    7    8    8   28
CONECT    8    9   29
CONECT    9   10   10   14
CONECT   10   11   30
CONECT   11   12   12   31
CONECT   12   13   17
CONECT   13   14   14   15
CONECT   14   32
CONECT   15   16
CONECT   16   17   33   34
CONECT   18   19   23
CONECT   19   20   35   36
CONECT   20   21   37   38
CONECT   21   22   39   40
CONECT   22   23   41   42
CONECT   23   43   44
END

HMDB0034371
     RDKit          3D
Piperettine
 44 46  0  0  0  0  0  0  0  0999 V2000
   -4.4170    2.5387    1.2504 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7821    1.4576    0.8158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3873    1.6094    0.7029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4893    0.7064    0.3805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0894    1.0692    0.3037 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8542    0.1338   -0.0349 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2058    0.5330   -0.1026 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3578    0.8723   -0.1605 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6548    0.3357   -0.4737 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8446   -0.9716   -0.8111 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0966   -1.5180   -1.0997 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1855   -0.6811   -1.0345 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0583    0.6452   -0.7029 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7842    1.1293   -0.4263 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3187    1.2088   -0.7322 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2660    0.1553   -0.6918 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5481   -0.9334   -1.2609 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6790    0.3854    0.5637 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3078   -0.8483   -0.0612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4305   -1.6068   -0.6654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7498   -1.5471    0.0138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1229   -0.1249    0.3759 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0294    0.5953    1.0430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9565    2.6245    0.9065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8048   -0.3011    0.2057 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2578    2.0671    0.5057 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4044   -0.8207   -0.2069 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5654   -0.7486   -0.5142 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4473    2.0039    0.1489 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0360   -1.6917   -0.8777 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1391   -2.5477   -1.3531 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6955    2.1607   -0.1762 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4688   -0.0917    0.3762 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1629    0.3159   -1.2798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6126   -0.6438   -0.9456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8084   -1.4752    0.7058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5388   -1.4039   -1.7845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1361   -2.7084   -0.6845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7746   -2.2297    0.8902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5281   -1.9147   -0.6924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5085    0.4250   -0.4765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9766   -0.2452    1.1081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2545    1.7025    0.9236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9676    0.3789    2.1423 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  2  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
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
  2 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 14  9  1  0
 23 18  1  0
 17 12  1  0
  3 24  1  0
  4 25  1  0
  5 26  1  0
  6 27  1  0
  7 28  1  0
  8 29  1  0
 10 30  1  0
 11 31  1  0
 14 32  1  0
 16 33  1  0
 16 34  1  0
 19 35  1  0
 19 36  1  0
 20 37  1  0
 20 38  1  0
 21 39  1  0
 21 40  1  0
 22 41  1  0
 22 42  1  0
 23 43  1  0
 23 44  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-[7-(1,3-Benzodioxol-5-yl)-1-oxo-2,4,6-heptatrienyl]piperidine, 9ci	HMDB
1-[7-(3,4-Methylenedioxyphenyl)heptatrienoyl]piperidine	HMDB

Chemical Formula

C₁₉H₂₁NO₃

Average Molecular Weight

311.3749

Monoisotopic Molecular Weight

311.152143543

IUPAC Name

(2E,4E,6E)-7-(2H-1,3-benzodioxol-5-yl)-1-(piperidin-1-yl)hepta-2,4,6-trien-1-one

Traditional Name

(2E,4E,6E)-7-(2H-1,3-benzodioxol-5-yl)-1-(piperidin-1-yl)hepta-2,4,6-trien-1-one

CAS Registry Number

583-34-6

SMILES

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

InChI Identifier

InChI=1S/C19H21NO3/c21-19(20-12-6-3-7-13-20)9-5-2-1-4-8-16-10-11-17-18(14-16)23-15-22-17/h1-2,4-5,8-11,14H,3,6-7,12-13,15H2/b2-1+,8-4+,9-5+

InChI Key

DLKOUKNODPCIHZ-UMYWTXKFSA-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
Styrene
Piperidine
Benzenoid
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

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0034371)
Cell membrane (HMDB: HMDB0034371)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0034371)

Source

Exogenous

Exogenous (HMDB: HMDB0034371)

Food

Food (HMDB: HMDB0034371)

Herb and spice

Spice

Pepper (Spice) (FooDB: FOOD00139)

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Plant

Plant (HMDB: HMDB0034371)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0034371)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	148 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	1.65 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	0.013 g/L	ALOGPS
logP	4.03	ALOGPS
logP	3.3	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Basic)	2.37	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	93.22 m³·mol⁻¹	ChemAxon
Polarizability	36.04 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]+	179.191	31661259
DarkChem	[M-H]-	175.819	31661259
DeepCCS	[M+H]+	173.223	30932474
DeepCCS	[M-H]-	170.866	30932474
DeepCCS	[M-2H]-	204.696	30932474
DeepCCS	[M+Na]+	179.924	30932474
AllCCS	[M+H]+	176.9	32859911
AllCCS	[M+H-H2O]+	173.5	32859911
AllCCS	[M+NH4]+	180.1	32859911
AllCCS	[M+Na]+	181.0	32859911
AllCCS	[M-H]-	180.2	32859911
AllCCS	[M+Na-2H]-	180.2	32859911
AllCCS	[M+HCOO]-	180.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Piperettine	O=C(\C=C\C=C\C=C\C1=CC2=C(OCO2)C=C1)N1CCCCC1	4253.3	Standard polar	33892256
Piperettine	O=C(\C=C\C=C\C=C\C1=CC2=C(OCO2)C=C1)N1CCCCC1	2742.7	Standard non polar	33892256
Piperettine	O=C(\C=C\C=C\C=C\C1=CC2=C(OCO2)C=C1)N1CCCCC1	3240.6	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Piperettine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0044-5791000000-53d30d4ea33d89883995	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Piperettine 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 - Piperettine 10V, Positive-QTOF	splash10-03di-3329000000-f436b5a2c510abc6c915	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperettine 20V, Positive-QTOF	splash10-000i-5922000000-60ea5fb06b0216ae1c77	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperettine 40V, Positive-QTOF	splash10-0ktr-9300000000-9f939b4d1404740f5427	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperettine 10V, Negative-QTOF	splash10-03di-0019000000-8875f6beb5bd859ce3c3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperettine 20V, Negative-QTOF	splash10-03e9-9567000000-e4866fadcad572dd5c0b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperettine 40V, Negative-QTOF	splash10-001i-9110000000-c0df613b78a564cc0ec3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperettine 10V, Negative-QTOF	splash10-03di-0009000000-9bf675b2e28db05b0d3b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperettine 20V, Negative-QTOF	splash10-03di-0359000000-50e3ed3ab9a77b7bb3ad	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperettine 40V, Negative-QTOF	splash10-0a4m-6985000000-6ef14a5b839b3c828a4f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperettine 10V, Positive-QTOF	splash10-03di-0049000000-9b514018f50e56011c40	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperettine 20V, Positive-QTOF	splash10-01p9-1794000000-7d96232be1ccd0b8f197	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperettine 40V, Positive-QTOF	splash10-001i-4920000000-05a5c50e2bdd7a49f994	2021-09-23	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

FDB012745

KNApSAcK ID

C00055295

Chemspider ID

8420440

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10244953

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1629131

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 Piperettine (HMDB0034371)

MOL for HMDB0034371 (Piperettine)

3D MOL for HMDB0034371 (Piperettine)

3D SDF for HMDB0034371 (Piperettine)

3D-SDF for HMDB0034371 (Piperettine)

PDB for HMDB0034371 (Piperettine)

3D PDB for HMDB0034371 (Piperettine)

SMILES for HMDB0034371 (Piperettine)

INCHI for HMDB0034371 (Piperettine)

Structure for HMDB0034371 (Piperettine)

3D Structure for HMDB0034371 (Piperettine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra