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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 17:30:03 UTC

Update Date

2022-09-22 17:44:03 UTC

HMDB ID

HMDB0029377

Secondary Accession Numbers

HMDB29377

Metabolite Identification

Common Name

Piperine

Description

Piperine, also known as fema 2909, belongs to the class of organic compounds known as alkaloids and derivatives. These are naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and more rarely other elements such as chlorine, bromine, and phosphorus. Piperine is a pepper tasting compound. Piperine is found in the highest concentration within pepper (Piper nigrum) and many other Piper species. Piperine has also been detected, but not quantified, in dills and herbs and spices. Piperine is responsible for the hot taste of pepper. Piperine has been used in trials studying the treatment of Multiple Myeloma and Deglutition Disorders. It is used to impart pungent taste to brandy.

Structure

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

HMDB0029377
     RDKit          3D
Piperine
 40 42  0  0  0  0  0  0  0  0999 V2000
    2.5908   -2.4802    0.9031 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4324   -1.3753    0.3475 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1176   -0.7755    0.1285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0016   -1.3693    0.5082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3146   -0.7310    0.2694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4325   -1.2998    0.6361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7067   -0.6666    0.3974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8680   -1.3335    0.8173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1220   -0.7991    0.6278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2889    0.4217    0.0134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1676    1.0888   -0.4040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9092    0.5494   -0.2122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5685    2.2746   -0.9850 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8903    2.5165   -0.5439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3798    1.2039   -0.3139 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5786   -0.6677   -0.0923 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4607    0.6197   -0.7445 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7591    0.8727   -1.5007 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9187    0.9797   -0.5245 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8455   -0.0881    0.5336 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9191   -1.2016    0.0917 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9953    0.1854   -0.3555 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0792   -2.3310    0.9956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3284    0.2205   -0.2173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4051   -2.2634    1.1281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7631   -2.3030    1.3071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9849   -1.3685    0.9776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0529    1.0996   -0.5518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8076    3.0173    0.4540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4928    3.0862   -1.2596 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3126    1.4260    0.0001 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6318    0.6436   -1.4817 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6430    1.7808   -2.1047 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9130   -0.0024   -2.1657 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8637    0.8583   -1.1062 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9373    1.9834   -0.0524 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4187    0.3400    1.4650 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8456   -0.5059    0.6881 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3347   -1.6303   -0.8368 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8872   -1.9760    0.8611 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
 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
  6 25  1  0
  8 26  1  0
  9 27  1  0
 12 28  1  0
 14 29  1  0
 14 30  1  0
 17 31  1  0
 17 32  1  0
 18 33  1  0
 18 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
M  END


  Mrv1652307301919592D          

 21 23  0  0  0  0            999 V2000
    2.0064    1.4143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0064    0.5893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2919    0.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5775    0.5893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1370    0.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8515    0.5893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7209    0.1768    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7209   -0.6482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4354   -1.0607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1498   -0.6482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1498    0.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4354    0.5893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5659   -0.6482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5659    0.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2804    0.5893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9949    0.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7795    0.4317    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2644   -0.2357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7795   -0.9032    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9949   -0.6482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2804   -1.0607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  7  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  7  8  1  0  0  0  0
  7 12  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 13 14  1  0  0  0  0
 13 21  2  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 20  2  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
  6 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0029377

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C17H19NO3/c19-17(18-10-4-1-5-11-18)7-3-2-6-14-8-9-15-16(12-14)21-13-20-15/h2-3,6-9,12H,1,4-5,10-11,13H2/b6-2+,7-3+

> <INCHI_KEY>
MXXWOMGUGJBKIW-YPCIICBESA-N

> <FORMULA>
C17H19NO3

> <MOLECULAR_WEIGHT>
285.3377

> <EXACT_MASS>
285.136493479

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
32.318273106862364

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E,4E)-5-(2H-1,3-benzodioxol-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one

> <JCHEM_LOGP>
2.777311050333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-0.13200194795020026

> <JCHEM_POLAR_SURFACE_AREA>
38.77

> <JCHEM_REFRACTIVITY>
82.90299999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
bioperine

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0029377
     RDKit          3D
Piperine
 40 42  0  0  0  0  0  0  0  0999 V2000
    2.5908   -2.4802    0.9031 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4324   -1.3753    0.3475 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1176   -0.7755    0.1285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0016   -1.3693    0.5082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3146   -0.7310    0.2694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4325   -1.2998    0.6361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7067   -0.6666    0.3974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8680   -1.3335    0.8173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1220   -0.7991    0.6278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2889    0.4217    0.0134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1676    1.0888   -0.4040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9092    0.5494   -0.2122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5685    2.2746   -0.9850 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8903    2.5165   -0.5439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3798    1.2039   -0.3139 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5786   -0.6677   -0.0923 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4607    0.6197   -0.7445 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7591    0.8727   -1.5007 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9187    0.9797   -0.5245 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8455   -0.0881    0.5336 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9191   -1.2016    0.0917 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9953    0.1854   -0.3555 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0792   -2.3310    0.9956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3284    0.2205   -0.2173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4051   -2.2634    1.1281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7631   -2.3030    1.3071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9849   -1.3685    0.9776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0529    1.0996   -0.5518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8076    3.0173    0.4540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4928    3.0862   -1.2596 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3126    1.4260    0.0001 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6318    0.6436   -1.4817 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6430    1.7808   -2.1047 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9130   -0.0024   -2.1657 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8637    0.8583   -1.1062 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9373    1.9834   -0.0524 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4187    0.3400    1.4650 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8456   -0.5059    0.6881 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3347   -1.6303   -0.8368 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8872   -1.9760    0.8611 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
 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
  6 25  1  0
  8 26  1  0
  9 27  1  0
 12 28  1  0
 14 29  1  0
 14 30  1  0
 17 31  1  0
 17 32  1  0
 18 33  1  0
 18 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
M  END

HEADER    PROTEIN                                 30-JUL-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-JUL-19         0                                  
HETATM    1  O   UNK     0       3.745   2.640   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       3.745   1.100   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.412   0.330   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.078   1.100   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.256   0.330   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.589   1.100   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       5.079   0.330   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       5.079  -1.210   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.413  -1.980   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.746  -1.210   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.746   0.330   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.413   1.100   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.923  -1.210   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.923   0.330   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.257   1.100   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -5.590   0.330   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -7.055   0.806   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -7.960  -0.440   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -7.055  -1.686   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -5.590  -1.210   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -4.257  -1.980   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5   14                                                       
CONECT    7    2    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12    7   11                                                       
CONECT   13   14   21                                                       
CONECT   14   13   15    6                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   20                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   16   19   21                                                  
CONECT   21   13   20                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    HMDB0029377
HETATM    1  O1  UNL     1       2.591  -2.480   0.903  1.00  0.00           O  
HETATM    2  C1  UNL     1       2.432  -1.375   0.347  1.00  0.00           C  
HETATM    3  C2  UNL     1       1.118  -0.775   0.129  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.002  -1.369   0.508  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.315  -0.731   0.269  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.432  -1.300   0.636  1.00  0.00           C  
HETATM    7  C6  UNL     1      -3.707  -0.667   0.397  1.00  0.00           C  
HETATM    8  C7  UNL     1      -4.868  -1.334   0.817  1.00  0.00           C  
HETATM    9  C8  UNL     1      -6.122  -0.799   0.628  1.00  0.00           C  
HETATM   10  C9  UNL     1      -6.289   0.422   0.013  1.00  0.00           C  
HETATM   11  C10 UNL     1      -5.168   1.089  -0.404  1.00  0.00           C  
HETATM   12  C11 UNL     1      -3.909   0.549  -0.212  1.00  0.00           C  
HETATM   13  O2  UNL     1      -5.569   2.275  -0.985  1.00  0.00           O  
HETATM   14  C12 UNL     1      -6.890   2.516  -0.544  1.00  0.00           C  
HETATM   15  O3  UNL     1      -7.380   1.204  -0.314  1.00  0.00           O  
HETATM   16  N1  UNL     1       3.579  -0.668  -0.092  1.00  0.00           N  
HETATM   17  C13 UNL     1       3.461   0.620  -0.745  1.00  0.00           C  
HETATM   18  C14 UNL     1       4.759   0.873  -1.501  1.00  0.00           C  
HETATM   19  C15 UNL     1       5.919   0.980  -0.524  1.00  0.00           C  
HETATM   20  C16 UNL     1       5.845  -0.088   0.534  1.00  0.00           C  
HETATM   21  C17 UNL     1       4.919  -1.202   0.092  1.00  0.00           C  
HETATM   22  H1  UNL     1       0.995   0.185  -0.356  1.00  0.00           H  
HETATM   23  H2  UNL     1       0.079  -2.331   0.996  1.00  0.00           H  
HETATM   24  H3  UNL     1      -1.328   0.220  -0.217  1.00  0.00           H  
HETATM   25  H4  UNL     1      -2.405  -2.263   1.128  1.00  0.00           H  
HETATM   26  H5  UNL     1      -4.763  -2.303   1.307  1.00  0.00           H  
HETATM   27  H6  UNL     1      -6.985  -1.369   0.978  1.00  0.00           H  
HETATM   28  H7  UNL     1      -3.053   1.100  -0.552  1.00  0.00           H  
HETATM   29  H8  UNL     1      -6.808   3.017   0.454  1.00  0.00           H  
HETATM   30  H9  UNL     1      -7.493   3.086  -1.260  1.00  0.00           H  
HETATM   31  H10 UNL     1       3.313   1.426   0.000  1.00  0.00           H  
HETATM   32  H11 UNL     1       2.632   0.644  -1.482  1.00  0.00           H  
HETATM   33  H12 UNL     1       4.643   1.781  -2.105  1.00  0.00           H  
HETATM   34  H13 UNL     1       4.913  -0.002  -2.166  1.00  0.00           H  
HETATM   35  H14 UNL     1       6.864   0.858  -1.106  1.00  0.00           H  
HETATM   36  H15 UNL     1       5.937   1.983  -0.052  1.00  0.00           H  
HETATM   37  H16 UNL     1       5.419   0.340   1.465  1.00  0.00           H  
HETATM   38  H17 UNL     1       6.846  -0.506   0.688  1.00  0.00           H  
HETATM   39  H18 UNL     1       5.335  -1.630  -0.837  1.00  0.00           H  
HETATM   40  H19 UNL     1       4.887  -1.976   0.861  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    6   24
CONECT    6    7   25
CONECT    7    8    8   12
CONECT    8    9   26
CONECT    9   10   10   27
CONECT   10   11   15
CONECT   11   12   12   13
CONECT   12   28
CONECT   13   14
CONECT   14   15   29   30
CONECT   16   17   21
CONECT   17   18   31   32
CONECT   18   19   33   34
CONECT   19   20   35   36
CONECT   20   21   37   38
CONECT   21   39   40
END

HMDB0029377
     RDKit          3D
Piperine
 40 42  0  0  0  0  0  0  0  0999 V2000
    2.5908   -2.4802    0.9031 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4324   -1.3753    0.3475 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1176   -0.7755    0.1285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0016   -1.3693    0.5082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3146   -0.7310    0.2694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4325   -1.2998    0.6361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7067   -0.6666    0.3974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8680   -1.3335    0.8173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1220   -0.7991    0.6278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2889    0.4217    0.0134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1676    1.0888   -0.4040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9092    0.5494   -0.2122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5685    2.2746   -0.9850 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8903    2.5165   -0.5439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3798    1.2039   -0.3139 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5786   -0.6677   -0.0923 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4607    0.6197   -0.7445 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7591    0.8727   -1.5007 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9187    0.9797   -0.5245 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8455   -0.0881    0.5336 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9191   -1.2016    0.0917 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9953    0.1854   -0.3555 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0792   -2.3310    0.9956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3284    0.2205   -0.2173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4051   -2.2634    1.1281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7631   -2.3030    1.3071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9849   -1.3685    0.9776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0529    1.0996   -0.5518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8076    3.0173    0.4540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4928    3.0862   -1.2596 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3126    1.4260    0.0001 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6318    0.6436   -1.4817 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6430    1.7808   -2.1047 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9130   -0.0024   -2.1657 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8637    0.8583   -1.1062 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9373    1.9834   -0.0524 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4187    0.3400    1.4650 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8456   -0.5059    0.6881 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3347   -1.6303   -0.8368 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8872   -1.9760    0.8611 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
 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
  6 25  1  0
  8 26  1  0
  9 27  1  0
 12 28  1  0
 14 29  1  0
 14 30  1  0
 17 31  1  0
 17 32  1  0
 18 33  1  0
 18 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
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(e,e)-1-Piperoylpiperidine	ChEBI
1-[(2E,4E)-5-(1,3-Benzodioxol-5-yl)-1-oxo-2,4-pentadienyl]piperidine	ChEBI
1-[(2E,4E)-5-(1,3-Benzodioxol-5-yl)-2,4-pentadienoyl]piperidine	ChEBI
1-Piperoyl-piperidine	ChEBI
1-Piperoylpiperidine	ChEBI
N-[(e,e)-Piperoyl]piperidine	ChEBI
Bioperine	HMDB
1-Piperoyl-(e,e)-piperidine	HMDB
FEMA 2909	HMDB
N-(e,e)-Piperoyl-piperidine	HMDB
N-Ee-piperoyl-piperidine	HMDB
Piperin	HMDB
Piperine, (e,Z)-isomer	MeSH, HMDB
Piperine, (Z,e)-isomer	MeSH, HMDB
Piperine, (Z,Z)-isomer	MeSH, HMDB
((1-5-(1,3)-Benzodioxol-5-yl)-1-oxo-2,4-pentadienyl)piperidine	MeSH, HMDB
(1-(5-(1,3)-Benzodioxol-5-yl)-1-oxo-2,4-pentadienyl)piperidine	MeSH, HMDB
Piperine, (e,e)-isomer	MeSH, HMDB

Chemical Formula

C₁₇H₁₉NO₃

Average Molecular Weight

285.3377

Monoisotopic Molecular Weight

285.136493479

IUPAC Name

(2E,4E)-5-(2H-1,3-benzodioxol-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one

Traditional Name

bioperine

CAS Registry Number

94-62-2

SMILES

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

InChI Identifier

InChI=1S/C17H19NO3/c19-17(18-10-4-1-5-11-18)7-3-2-6-14-8-9-15-16(12-14)21-13-20-15/h2-3,6-9,12H,1,4-5,10-11,13H2/b6-2+,7-3+

InChI Key

MXXWOMGUGJBKIW-YPCIICBESA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alkaloids and derivatives. These are naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and more rarely other elements such as chlorine, bromine, and phosphorus.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Not Available

Sub Class

Not Available

Direct Parent

Alkaloids and derivatives

Alternative Parents

Substituents

Benzodioxole
N-acyl-piperidine
Alkaloid or derivatives
Styrene
Piperidine
Benzenoid
Tertiary carboxylic acid amide
Carboxamide group
Acetal
Carboxylic acid derivative
Oxacycle
Azacycle
Organoheterocyclic compound
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organic nitrogen compound
Carbonyl group
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

N-acylpiperidine (CHEBI:28821 )
benzodioxoles (CHEBI:28821 )
piperidine alkaloid (CHEBI:28821 )
carboxamide (CHEBI:28821 )
Piperidine alkaloids (C03882 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	129 °C	Not Available
Boiling Point	498.00 to 499.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	0.04 mg/mL at 18 °C	Not Available
LogP	2.656 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	171.424	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001364

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.15 g/L	ALOGPS
logP	2.78	ChemAxon
pKa (Strongest Basic)	-0.13	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	3	ChemAxon
Refractivity	82.9 m³·mol⁻¹	ChemAxon
Polarizability	32.32 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]+	171.949	31661259
DarkChem	[M-H]-	170.22	31661259
DeepCCS	[M+H]+	164.999	30932474
DeepCCS	[M-H]-	162.604	30932474
DeepCCS	[M-2H]-	195.828	30932474
DeepCCS	[M+Na]+	171.037	30932474
AllCCS	[M+H]+	167.8	32859911
AllCCS	[M+H-H2O]+	164.3	32859911
AllCCS	[M+NH4]+	171.0	32859911
AllCCS	[M+Na]+	171.9	32859911
AllCCS	[M-H]-	172.9	32859911
AllCCS	[M+Na-2H]-	172.8	32859911
AllCCS	[M+HCOO]-	172.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Piperine	O=C(\C=C\C=C\C1=CC2=C(OCO2)C=C1)N1CCCCC1	3846.8	Standard polar	33892256
Piperine	O=C(\C=C\C=C\C1=CC2=C(OCO2)C=C1)N1CCCCC1	2482.8	Standard non polar	33892256
Piperine	O=C(\C=C\C=C\C1=CC2=C(OCO2)C=C1)N1CCCCC1	2908.8	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Piperine EI-B (Non-derivatized)	splash10-0fe0-0590000000-49115b64f9d288ede20b	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Piperine EI-B (Non-derivatized)	splash10-0uki-1980000000-0d80d5bd56077694f4ab	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Piperine EI-B (Non-derivatized)	splash10-0fe0-0590000000-49115b64f9d288ede20b	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Piperine EI-B (Non-derivatized)	splash10-0uki-1980000000-0d80d5bd56077694f4ab	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Piperine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ru3-5490000000-47caa063ebe950468c83	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Piperine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0v4r-4970000000-d7ea6f47f4b46495acb4	2015-03-01	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Piperine LC-ESI-qTof , Positive-QTOF	splash10-0udi-0910000000-28987f355a39728ed8e4	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Piperine LC-ESI-IT , positive-QTOF	splash10-0udi-0090000000-6221df9a927cf5dae43f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Piperine Linear Ion Trap , positive-QTOF	splash10-0udi-0090000000-f586ee65972a8599fb3e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Piperine Linear Ion Trap , positive-QTOF	splash10-0udi-0190000000-9f77f056ac9f2e385656	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Piperine Linear Ion Trap , positive-QTOF	splash10-0udi-0090000000-d91bf95f43f53499a538	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Piperine Linear Ion Trap , positive-QTOF	splash10-0udi-0190000000-1f5b570135a2c33d60cb	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Piperine Linear Ion Trap , positive-QTOF	splash10-0udi-0190000000-c67e35d994bd1857d3b3	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Piperine Linear Ion Trap , positive-QTOF	splash10-0udi-0190000000-38727bddc27cc1f12b21	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Piperine Linear Ion Trap , positive-QTOF	splash10-004r-0032950000-09b8545ba31f6fbf5243	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Piperine Linear Ion Trap , positive-QTOF	splash10-01ti-0044970000-8efb835b518a1f9d631e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Piperine Linear Ion Trap , positive-QTOF	splash10-004r-0033960000-0ebcac3b31c8914732a9	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Piperine Linear Ion Trap , positive-QTOF	splash10-0a4i-0009700000-45fc15cfc95d4cb7619c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Piperine Linear Ion Trap , positive-QTOF	splash10-0a4i-0009500000-356adf7cecbec3f587a1	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Piperine Linear Ion Trap , positive-QTOF	splash10-004r-0022950000-438f2d66c26e4fad4df9	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Piperine , positive-QTOF	splash10-0uxr-0930000000-08188c35582e879e867f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Piperine 40V, Positive-QTOF	splash10-014i-1900000000-8556d96344dd58005484	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Piperine 60V, Positive-QTOF	splash10-0gbl-0910000000-0cc6374f3392d452f5fa	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Piperine 30V, Positive-QTOF	splash10-0udr-0190000000-1fd31902ba916f49f5c0	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Piperine 15V, Positive-QTOF	splash10-000i-0090000000-d9688e24ce807650b12c	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperine 10V, Positive-QTOF	splash10-000i-2290000000-12a3336a15ec4f2d04ad	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperine 20V, Positive-QTOF	splash10-000i-6960000000-cfbbefb16249f62a712d	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperine 40V, Positive-QTOF	splash10-05q3-9300000000-e0c13b92ad036042aa06	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperine 10V, Negative-QTOF	splash10-001i-0190000000-2e45c46d9e273a3e57f4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperine 20V, Negative-QTOF	splash10-001i-6490000000-03ac1126cea4a744d034	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperine 40V, Negative-QTOF	splash10-001i-9200000000-b9bed611c188499924d5	2016-08-03	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Placenta

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Female	Normal	27355821	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	27015276	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

Associated Disorders and Diseases

Disease References

Colorectal cancer

Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]

Associated OMIM IDs

114500 (Colorectal cancer)

External Links

DrugBank ID

DB12582

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Piperine

METLIN ID

Not Available

PubChem Compound

638024

PDB ID

Not Available

ChEBI ID

28821

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1033851

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Piperine (HMDB0029377)

MOL for HMDB0029377 (Piperine)

3D MOL for HMDB0029377 (Piperine)

3D SDF for HMDB0029377 (Piperine)

3D-SDF for HMDB0029377 (Piperine)

PDB for HMDB0029377 (Piperine)

3D PDB for HMDB0029377 (Piperine)

SMILES for HMDB0029377 (Piperine)

INCHI for HMDB0029377 (Piperine)

Structure for HMDB0029377 (Piperine)

3D Structure for HMDB0029377 (Piperine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra