NP-MRD: Showing NP-Card for Piperine (NP0000084)

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Record Information

Version

2.0

Created at

2012-09-11 17:30:03 UTC

Updated at

2021-08-19 20:22:33 UTC

NP-MRD ID

NP0000084

Secondary Accession Numbers

None

Natural Product 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


  Mrv1652306242117433D          

 40 42  0  0  0  0            999 V2000
   -2.4029    2.5115    0.5952 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4722    1.2530    0.4893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2432    0.4869    0.3141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0579    1.0880    0.2631 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1690    0.3118    0.0872 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3220    0.9030    0.0381 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5557    0.1616   -0.1353 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6443   -1.2016   -0.2630 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8767   -1.8478   -0.4280 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0564   -1.1432   -0.4695 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9827    0.2256   -0.3426 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7727    0.8619   -0.1804 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3093    0.6750   -0.4194 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1838   -0.4129   -0.1814 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.4004   -1.4998   -0.6187 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7016    0.5560    0.5347 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9171    1.3154    0.7145 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.0803    0.8023   -0.0613 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.7104   -0.3754   -0.9095 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.0815   -1.4048    0.0408 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7048   -0.8781    0.4035 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2247   -0.5836    0.2196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0219    2.1552    0.3539 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0828   -0.7523    0.0011 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3239    1.9906    0.1337 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7432   -1.7910   -0.2358 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9188   -2.9218   -0.5262 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7200    1.9392   -0.0810 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3285   -0.4859    0.9308 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1438   -0.3173   -0.7169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1656    1.3075    1.8047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7077    2.3819    0.4695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8727    0.4400    0.6497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4813    1.6271   -0.6882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6323   -0.7804   -1.3665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9441   -0.1644   -1.6667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9428   -2.3393   -0.5200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7154   -1.5984    0.9071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0509   -1.1158   -0.4691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4027   -1.3800    1.3287 H   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
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  2 16  1  0  0  0  0
 16 17  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
 12  7  1  0  0  0  0
 21 16  1  0  0  0  0
 15 10  1  0  0  0  0
  3 22  1  0  0  0  0
  4 23  1  0  0  0  0
  5 24  1  0  0  0  0
  6 25  1  0  0  0  0
  8 26  1  0  0  0  0
  9 27  1  0  0  0  0
 12 28  1  0  0  0  0
 14 29  1  0  0  0  0
 14 30  1  0  0  0  0
 17 31  1  0  0  0  0
 17 32  1  0  0  0  0
 18 33  1  0  0  0  0
 18 34  1  0  0  0  0
 19 35  1  0  0  0  0
 19 36  1  0  0  0  0
 20 37  1  0  0  0  0
 20 38  1  0  0  0  0
 21 39  1  0  0  0  0
 21 40  1  0  0  0  0
M  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


  Mrv1652306242117433D          

 40 42  0  0  0  0            999 V2000
   -2.4029    2.5115    0.5952 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4722    1.2530    0.4893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2432    0.4869    0.3141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0579    1.0880    0.2631 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1690    0.3118    0.0872 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3220    0.9030    0.0381 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5557    0.1616   -0.1353 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6443   -1.2016   -0.2630 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8767   -1.8478   -0.4280 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0564   -1.1432   -0.4695 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9827    0.2256   -0.3426 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7727    0.8619   -0.1804 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3093    0.6750   -0.4194 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1838   -0.4129   -0.1814 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.4004   -1.4998   -0.6187 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7016    0.5560    0.5347 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9171    1.3154    0.7145 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.0803    0.8023   -0.0613 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.7104   -0.3754   -0.9095 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.0815   -1.4048    0.0408 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7048   -0.8781    0.4035 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2247   -0.5836    0.2196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0219    2.1552    0.3539 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0828   -0.7523    0.0011 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3239    1.9906    0.1337 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7432   -1.7910   -0.2358 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9188   -2.9218   -0.5262 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7200    1.9392   -0.0810 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3285   -0.4859    0.9308 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1438   -0.3173   -0.7169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1656    1.3075    1.8047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7077    2.3819    0.4695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8727    0.4400    0.6497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4813    1.6271   -0.6882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6323   -0.7804   -1.3665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9441   -0.1644   -1.6667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9428   -2.3393   -0.5200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7154   -1.5984    0.9071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0509   -1.1158   -0.4691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4027   -1.3800    1.3287 H   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
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  2 16  1  0  0  0  0
 16 17  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
 12  7  1  0  0  0  0
 21 16  1  0  0  0  0
 15 10  1  0  0  0  0
  3 22  1  0  0  0  0
  4 23  1  0  0  0  0
  5 24  1  0  0  0  0
  6 25  1  0  0  0  0
  8 26  1  0  0  0  0
  9 27  1  0  0  0  0
 12 28  1  0  0  0  0
 14 29  1  0  0  0  0
 14 30  1  0  0  0  0
 17 31  1  0  0  0  0
 17 32  1  0  0  0  0
 18 33  1  0  0  0  0
 18 34  1  0  0  0  0
 19 35  1  0  0  0  0
 19 36  1  0  0  0  0
 20 37  1  0  0  0  0
 20 38  1  0  0  0  0
 21 39  1  0  0  0  0
 21 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000084

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]\C(\C(\[H])=C(/[H])C1=C([H])C([H])=C2OC([H])([H])OC2=C1[H])=C(\[H])C(=O)N1C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H]

> <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

> <ALOGPS_LOGP>
3.38

> <JCHEM_LOGP>
2.777311050333333

> <ALOGPS_LOGS>
-3.28

> <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

> <ALOGPS_SOLUBILITY>
1.49e-01 g/l

> <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                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  O   UNK     0      -2.403   2.511   0.595  0.00  0.00           O+0
HETATM    2  C   UNK     0      -2.472   1.253   0.489  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.243   0.487   0.314  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.058   1.088   0.263  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.169   0.312   0.087  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.322   0.903   0.038  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.556   0.162  -0.135  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.644  -1.202  -0.263  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.877  -1.848  -0.428  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.056  -1.143  -0.470  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.983   0.226  -0.343  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.773   0.862  -0.180  0.00  0.00           C+0
HETATM   13  O   UNK     0       7.309   0.675  -0.419  0.00  0.00           O+0
HETATM   14  C   UNK     0       8.184  -0.413  -0.181  0.00  0.00           C+0
HETATM   15  O   UNK     0       7.400  -1.500  -0.619  0.00  0.00           O+0
HETATM   16  N   UNK     0      -3.702   0.556   0.535  0.00  0.00           N+0
HETATM   17  C   UNK     0      -4.917   1.315   0.715  0.00  0.00           C+0
HETATM   18  C   UNK     0      -6.080   0.802  -0.061  0.00  0.00           C+0
HETATM   19  C   UNK     0      -5.710  -0.375  -0.910  0.00  0.00           C+0
HETATM   20  C   UNK     0      -5.082  -1.405   0.041  0.00  0.00           C+0
HETATM   21  C   UNK     0      -3.705  -0.878   0.404  0.00  0.00           C+0
HETATM   22  H   UNK     0      -1.225  -0.584   0.220  0.00  0.00           H+0
HETATM   23  H   UNK     0      -0.022   2.155   0.354  0.00  0.00           H+0
HETATM   24  H   UNK     0       1.083  -0.752   0.001  0.00  0.00           H+0
HETATM   25  H   UNK     0       2.324   1.991   0.134  0.00  0.00           H+0
HETATM   26  H   UNK     0       2.743  -1.791  -0.236  0.00  0.00           H+0
HETATM   27  H   UNK     0       4.919  -2.922  -0.526  0.00  0.00           H+0
HETATM   28  H   UNK     0       4.720   1.939  -0.081  0.00  0.00           H+0
HETATM   29  H   UNK     0       8.329  -0.486   0.931  0.00  0.00           H+0
HETATM   30  H   UNK     0       9.144  -0.317  -0.717  0.00  0.00           H+0
HETATM   31  H   UNK     0      -5.166   1.308   1.805  0.00  0.00           H+0
HETATM   32  H   UNK     0      -4.708   2.382   0.470  0.00  0.00           H+0
HETATM   33  H   UNK     0      -6.873   0.440   0.650  0.00  0.00           H+0
HETATM   34  H   UNK     0      -6.481   1.627  -0.688  0.00  0.00           H+0
HETATM   35  H   UNK     0      -6.632  -0.780  -1.367  0.00  0.00           H+0
HETATM   36  H   UNK     0      -4.944  -0.164  -1.667  0.00  0.00           H+0
HETATM   37  H   UNK     0      -4.943  -2.339  -0.520  0.00  0.00           H+0
HETATM   38  H   UNK     0      -5.715  -1.598   0.907  0.00  0.00           H+0
HETATM   39  H   UNK     0      -3.051  -1.116  -0.469  0.00  0.00           H+0
HETATM   40  H   UNK     0      -3.403  -1.380   1.329  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3   16                                                  
CONECT    3    2    4   22                                                  
CONECT    4    3    5   23                                                  
CONECT    5    4    6   24                                                  
CONECT    6    5    7   25                                                  
CONECT    7    6    8   12                                                  
CONECT    8    7    9   26                                                  
CONECT    9    8   10   27                                                  
CONECT   10    9   11   15                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11    7   28                                                  
CONECT   13   11   14                                                       
CONECT   14   13   15   29   30                                             
CONECT   15   14   10                                                       
CONECT   16    2   17   21                                                  
CONECT   17   16   18   31   32                                             
CONECT   18   17   19   33   34                                             
CONECT   19   18   20   35   36                                             
CONECT   20   19   21   37   38                                             
CONECT   21   20   16   39   40                                             
CONECT   22    3                                                            
CONECT   23    4                                                            
CONECT   24    5                                                            
CONECT   25    6                                                            
CONECT   26    8                                                            
CONECT   27    9                                                            
CONECT   28   12                                                            
CONECT   29   14                                                            
CONECT   30   14                                                            
CONECT   31   17                                                            
CONECT   32   17                                                            
CONECT   33   18                                                            
CONECT   34   18                                                            
CONECT   35   19                                                            
CONECT   36   19                                                            
CONECT   37   20                                                            
CONECT   38   20                                                            
CONECT   39   21                                                            
CONECT   40   21                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   84    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
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M  END

View in JSmol

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
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	HMDB
Piperine, (Z,e)-isomer	HMDB
Piperine, (Z,Z)-isomer	HMDB
((1-5-(1,3)-Benzodioxol-5-yl)-1-oxo-2,4-pentadienyl)piperidine	HMDB
(1-(5-(1,3)-Benzodioxol-5-yl)-1-oxo-2,4-pentadienyl)piperidine	HMDB
Piperine, (e,e)-isomer	HMDB
Bioperine	HMDB

Chemical Formula

C₁₇H₁₉NO₃

Average Mass

285.3377 Da

Monoisotopic Mass

285.13649 Da

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

[H]\C(\C(\[H])=C(/[H])C1=C([H])C([H])=C2OC([H])([H])OC2=C1[H])=C(\[H])C(=O)N1C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H]

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

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Aglaia perviridis	LOTUS Database	35616633
Anethum graveolens	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Boletinus cavipes	-	KNApSAcK
Capsicum annuum	FooDB	PHYTOHUB
Piper acutisleginum	KNApSAcK Database	22123792
Piper attenuatum	LOTUS Database	35616633
Piper betle	KNApSAcK Database	22123792
Piper boehmeriifolium	LOTUS Database	35616633
Piper capense	LOTUS Database	35616633
Piper chaba	KNApSAcK Database	22123792
Piper cubeba	LOTUS Database	35616633
Piper guineense	LOTUS Database	35616633
Piper guineense Schum.et Thom.	KNApSAcK Database	22123792
Piper khasiana	KNApSAcK Database	22123792
Piper longum	KNApSAcK Database	22123792
Piper nigrum	KNApSAcK Database	22123792
Piper nigrum L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Piper officinarum	KNApSAcK Database	22123792
Piper pedicellatum	LOTUS Database	35616633
Piper retrofractum	Plant	KNApSAcK
Piper retrofractum Vahl.	KNApSAcK Database	22123792
Piper swartzianum	LOTUS Database	35616633
Piper thomsoni	KNApSAcK Database	22123792
Piper thomsonii	LOTUS Database	35616633
Piper trichostachyon	KNApSAcK Database	22123792
Piper tuberculatum	LOTUS Database	35616633

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 )

Physical Properties

State

Solid

Experimental 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

Predicted Properties

Property	Value	Source
Water Solubility	0.15 g/L	ALOGPS
logP	3.38	ALOGPS
logP	2.78	ChemAxon
logS	-3.3	ALOGPS
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

External Links

HMDB ID

HMDB0029377

DrugBank ID

DB12582

Phenol Explorer Compound ID

Not Available

FoodDB 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

Good Scents ID

rw1033851

References

General References

Lin Z, Hoult JR, Bennett DC, Raman A: Stimulation of mouse melanocyte proliferation by Piper nigrum fruit extract and its main alkaloid, piperine. Planta Med. 1999 Oct;65(7):600-3. doi: 10.1055/s-1999-14031. [PubMed:10575373 ]
Pradeep CR, Kuttan G: Piperine is a potent inhibitor of nuclear factor-kappaB (NF-kappaB), c-Fos, CREB, ATF-2 and proinflammatory cytokine gene expression in B16F-10 melanoma cells. Int Immunopharmacol. 2004 Dec 20;4(14):1795-803. doi: 10.1016/j.intimp.2004.08.005. [PubMed:15531295 ]
Wattanathorn J, Chonpathompikunlert P, Muchimapura S, Priprem A, Tankamnerdthai O: Piperine, the potential functional food for mood and cognitive disorders. Food Chem Toxicol. 2008 Sep;46(9):3106-10. doi: 10.1016/j.fct.2008.06.014. Epub 2008 Jun 29. [PubMed:18639606 ]
D'Cruz SC, Vaithinathan S, Saradha B, Mathur PP: Piperine activates testicular apoptosis in adult rats. J Biochem Mol Toxicol. 2008 Nov-Dec;22(6):382-8. doi: 10.1002/jbt.20251. [PubMed:19110999 ]
Lin Y, Xu J, Liao H, Li L, Pan L: Piperine induces apoptosis of lung cancer A549 cells via p53-dependent mitochondrial signaling pathway. Tumour Biol. 2014 Apr;35(4):3305-10. doi: 10.1007/s13277-013-1433-4. Epub 2013 Nov 24. [PubMed:24272201 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing NP-Card for Piperine (NP0000084)

MOL for NP0000084 (Piperine)

3D MOL for NP0000084 (Piperine)

3D SDF for NP0000084 (Piperine)

3D-SDF for NP0000084 (Piperine)

PDB for NP0000084 (Piperine)

3D PDB for NP0000084 (Piperine)

SMILES for NP0000084 (Piperine)

INCHI for NP0000084 (Piperine)

Structure for NP0000084 (Piperine)

3D Structure for NP0000084 (Piperine)