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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 17:36:14 UTC

Update Date

2022-09-22 18:34:24 UTC

HMDB ID

HMDB0030341

Secondary Accession Numbers

HMDB30341

Metabolite Identification

Common Name

Piplartine

Description

Piplartine, also known as piperlongumine, belongs to the class of organic compounds known as cinnamic acids and derivatives. These are organic aromatic compounds containing a benzene and a carboxylic acid group (or a derivative thereof) forming 3-phenylprop-2-enoic acid. Based on a literature review a significant number of articles have been published on Piplartine.

Structure

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

HMDB0030341
     RDKit          3D
Piplartine
 42 43  0  0  0  0  0  0  0  0999 V2000
   -4.0508    3.7118    0.5030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2969    2.3418    0.5764 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3478    1.3570    0.4533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0249    1.6513    0.2393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0410    0.6721    0.1107 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3315    1.0919   -0.1143 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3373    0.2463   -0.2495 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6756    0.7722   -0.4719 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7822    2.0516   -0.5168 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8325   -0.0230   -0.6356 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1266    0.6628   -0.8332 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1603    0.0391    0.0442 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1802   -1.4343    0.0544 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1001   -2.1100   -0.2584 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8379   -1.4352   -0.6290 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8339   -2.0858   -0.9208 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4403   -0.6378    0.2064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7852   -0.9586    0.4245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1434   -2.2789    0.5140 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1676   -3.2838    0.3874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7382    0.0360    0.5479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0478   -0.3332    0.7617 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9692   -0.5712   -0.2827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0906    4.1136   -0.5296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1247    4.0362    1.0174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8863    4.2281    1.0591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7537    2.6884    0.1706 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5303    2.1647   -0.1728 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1509   -0.8215   -0.1883 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0272    1.7243   -0.5420 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4334    0.6258   -1.8927 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1632    0.3941   -0.2749 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0517    0.3908    1.1004 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1174   -1.9561    0.3283 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1651   -3.1979   -0.2356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7103   -1.4286    0.1125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3903   -3.1049    1.1868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6062   -3.1842   -0.5700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5649   -4.2977    0.5159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4457   -0.5565   -1.2714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4765   -1.5318   -0.1489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7350    0.2308   -0.3246 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
  5 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 18 21  2  0
 21 22  1  0
 22 23  1  0
 21  3  1  0
 15 10  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  6 28  1  0
  7 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  0
 12 33  1  0
 13 34  1  0
 14 35  1  0
 17 36  1  0
 20 37  1  0
 20 38  1  0
 20 39  1  0
 23 40  1  0
 23 41  1  0
 23 42  1  0
M  END


  Mrv0541 05061305102D          

 23 24  0  0  0  0            999 V2000
   -5.7158    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
  6  4  2  0  0  0  0
  8  7  2  0  0  0  0
  9  5  1  0  0  0  0
 12  7  1  0  0  0  0
 12 10  2  0  0  0  0
 12 11  1  0  0  0  0
 13 10  1  0  0  0  0
 14 11  2  0  0  0  0
 15  6  1  0  0  0  0
 16  8  1  0  0  0  0
 17 13  2  0  0  0  0
 17 14  1  0  0  0  0
 18  9  1  0  0  0  0
 18 15  1  0  0  0  0
 18 16  1  0  0  0  0
 19 15  2  0  0  0  0
 20 16  2  0  0  0  0
 21  1  1  0  0  0  0
 21 13  1  0  0  0  0
 22  2  1  0  0  0  0
 22 14  1  0  0  0  0
 23  3  1  0  0  0  0
 23 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030341

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC(\C=C\C(=O)N2CCC=CC2=O)=CC(OC)=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C17H19NO5/c1-21-13-10-12(11-14(22-2)17(13)23-3)7-8-16(20)18-9-5-4-6-15(18)19/h4,6-8,10-11H,5,9H2,1-3H3/b8-7+

> <INCHI_KEY>
VABYUUZNAVQNPG-BQYQJAHWSA-N

> <FORMULA>
C17H19NO5

> <MOLECULAR_WEIGHT>
317.3365

> <EXACT_MASS>
317.126322723

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
33.45237913488001

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-[(2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]-1,2,5,6-tetrahydropyridin-2-one

> <ALOGPS_LOGP>
2.32

> <JCHEM_LOGP>
1.7378093393333336

> <ALOGPS_LOGS>
-3.86

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.76506242333467

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2807232544006673

> <JCHEM_POLAR_SURFACE_AREA>
65.07000000000001

> <JCHEM_REFRACTIVITY>
87.32389999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.40e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
piperlongumine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030341
     RDKit          3D
Piplartine
 42 43  0  0  0  0  0  0  0  0999 V2000
   -4.0508    3.7118    0.5030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2969    2.3418    0.5764 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3478    1.3570    0.4533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0249    1.6513    0.2393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0410    0.6721    0.1107 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3315    1.0919   -0.1143 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3373    0.2463   -0.2495 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6756    0.7722   -0.4719 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7822    2.0516   -0.5168 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8325   -0.0230   -0.6356 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1266    0.6628   -0.8332 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1603    0.0391    0.0442 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1802   -1.4343    0.0544 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1001   -2.1100   -0.2584 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8379   -1.4352   -0.6290 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8339   -2.0858   -0.9208 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4403   -0.6378    0.2064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7852   -0.9586    0.4245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1434   -2.2789    0.5140 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1676   -3.2838    0.3874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7382    0.0360    0.5479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0478   -0.3332    0.7617 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9692   -0.5712   -0.2827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0906    4.1136   -0.5296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1247    4.0362    1.0174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8863    4.2281    1.0591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7537    2.6884    0.1706 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5303    2.1647   -0.1728 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1509   -0.8215   -0.1883 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0272    1.7243   -0.5420 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4334    0.6258   -1.8927 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1632    0.3941   -0.2749 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0517    0.3908    1.1004 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1174   -1.9561    0.3283 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1651   -3.1979   -0.2356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7103   -1.4286    0.1125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3903   -3.1049    1.1868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6062   -3.1842   -0.5700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5649   -4.2977    0.5159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4457   -0.5565   -1.2714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4765   -1.5318   -0.1489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7350    0.2308   -0.3246 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
  5 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 18 21  2  0
 21 22  1  0
 22 23  1  0
 21  3  1  0
 15 10  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  6 28  1  0
  7 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  0
 12 33  1  0
 13 34  1  0
 14 35  1  0
 17 36  1  0
 20 37  1  0
 20 38  1  0
 20 39  1  0
 23 40  1  0
 23 41  1  0
 23 42  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     -10.669   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -8.002   4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -9.336   3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -5.335   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -8.002   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -6.668   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -8.002   1.540   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0      -2.667  -4.620   0.000  0.00  0.00           N+0
HETATM   19  O   UNK     0      -5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -6.668   3.850   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -9.336   2.310   0.000  0.00  0.00           O+0
CONECT    1   21                                                            
CONECT    2   22                                                            
CONECT    3   23                                                            
CONECT    4    5    6                                                       
CONECT    5    4    9                                                       
CONECT    6    4   15                                                       
CONECT    7    8   12                                                       
CONECT    8    7   16                                                       
CONECT    9    5   18                                                       
CONECT   10   12   13                                                       
CONECT   11   12   14                                                       
CONECT   12    7   10   11                                                  
CONECT   13   10   17   21                                                  
CONECT   14   11   17   22                                                  
CONECT   15    6   18   19                                                  
CONECT   16    8   18   20                                                  
CONECT   17   13   14   23                                                  
CONECT   18    9   15   16                                                  
CONECT   19   15                                                            
CONECT   20   16                                                            
CONECT   21    1   13                                                       
CONECT   22    2   14                                                       
CONECT   23    3   17                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

COMPND    HMDB0030341
HETATM    1  C1  UNL     1      -4.051   3.712   0.503  1.00  0.00           C  
HETATM    2  O1  UNL     1      -4.297   2.342   0.576  1.00  0.00           O  
HETATM    3  C2  UNL     1      -3.348   1.357   0.453  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.025   1.651   0.239  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.041   0.672   0.111  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.332   1.092  -0.114  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.337   0.246  -0.250  1.00  0.00           C  
HETATM    8  C7  UNL     1       2.676   0.772  -0.472  1.00  0.00           C  
HETATM    9  O2  UNL     1       2.782   2.052  -0.517  1.00  0.00           O  
HETATM   10  N1  UNL     1       3.833  -0.023  -0.636  1.00  0.00           N  
HETATM   11  C8  UNL     1       5.127   0.663  -0.833  1.00  0.00           C  
HETATM   12  C9  UNL     1       6.160   0.039   0.044  1.00  0.00           C  
HETATM   13  C10 UNL     1       6.180  -1.434   0.054  1.00  0.00           C  
HETATM   14  C11 UNL     1       5.100  -2.110  -0.258  1.00  0.00           C  
HETATM   15  C12 UNL     1       3.838  -1.435  -0.629  1.00  0.00           C  
HETATM   16  O3  UNL     1       2.834  -2.086  -0.921  1.00  0.00           O  
HETATM   17  C13 UNL     1      -1.440  -0.638   0.206  1.00  0.00           C  
HETATM   18  C14 UNL     1      -2.785  -0.959   0.424  1.00  0.00           C  
HETATM   19  O4  UNL     1      -3.143  -2.279   0.514  1.00  0.00           O  
HETATM   20  C15 UNL     1      -2.168  -3.284   0.387  1.00  0.00           C  
HETATM   21  C16 UNL     1      -3.738   0.036   0.548  1.00  0.00           C  
HETATM   22  O5  UNL     1      -5.048  -0.333   0.762  1.00  0.00           O  
HETATM   23  C17 UNL     1      -5.969  -0.571  -0.283  1.00  0.00           C  
HETATM   24  H1  UNL     1      -4.091   4.114  -0.530  1.00  0.00           H  
HETATM   25  H2  UNL     1      -3.125   4.036   1.017  1.00  0.00           H  
HETATM   26  H3  UNL     1      -4.886   4.228   1.059  1.00  0.00           H  
HETATM   27  H4  UNL     1      -1.754   2.688   0.171  1.00  0.00           H  
HETATM   28  H5  UNL     1       0.530   2.165  -0.173  1.00  0.00           H  
HETATM   29  H6  UNL     1       1.151  -0.821  -0.188  1.00  0.00           H  
HETATM   30  H7  UNL     1       5.027   1.724  -0.542  1.00  0.00           H  
HETATM   31  H8  UNL     1       5.433   0.626  -1.893  1.00  0.00           H  
HETATM   32  H9  UNL     1       7.163   0.394  -0.275  1.00  0.00           H  
HETATM   33  H10 UNL     1       6.052   0.391   1.100  1.00  0.00           H  
HETATM   34  H11 UNL     1       7.117  -1.956   0.328  1.00  0.00           H  
HETATM   35  H12 UNL     1       5.165  -3.198  -0.236  1.00  0.00           H  
HETATM   36  H13 UNL     1      -0.710  -1.429   0.113  1.00  0.00           H  
HETATM   37  H14 UNL     1      -1.390  -3.105   1.187  1.00  0.00           H  
HETATM   38  H15 UNL     1      -1.606  -3.184  -0.570  1.00  0.00           H  
HETATM   39  H16 UNL     1      -2.565  -4.298   0.516  1.00  0.00           H  
HETATM   40  H17 UNL     1      -5.446  -0.556  -1.271  1.00  0.00           H  
HETATM   41  H18 UNL     1      -6.476  -1.532  -0.149  1.00  0.00           H  
HETATM   42  H19 UNL     1      -6.735   0.231  -0.325  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3
CONECT    3    4    4   21
CONECT    4    5   27
CONECT    5    6   17   17
CONECT    6    7    7   28
CONECT    7    8   29
CONECT    8    9    9   10
CONECT   10   11   15
CONECT   11   12   30   31
CONECT   12   13   32   33
CONECT   13   14   14   34
CONECT   14   15   35
CONECT   15   16   16
CONECT   17   18   36
CONECT   18   19   21   21
CONECT   19   20
CONECT   20   37   38   39
CONECT   21   22
CONECT   22   23
CONECT   23   40   41   42
END

HMDB0030341
     RDKit          3D
Piplartine
 42 43  0  0  0  0  0  0  0  0999 V2000
   -4.0508    3.7118    0.5030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2969    2.3418    0.5764 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3478    1.3570    0.4533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0249    1.6513    0.2393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0410    0.6721    0.1107 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3315    1.0919   -0.1143 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3373    0.2463   -0.2495 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6756    0.7722   -0.4719 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7822    2.0516   -0.5168 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8325   -0.0230   -0.6356 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1266    0.6628   -0.8332 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1603    0.0391    0.0442 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1802   -1.4343    0.0544 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1001   -2.1100   -0.2584 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8379   -1.4352   -0.6290 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8339   -2.0858   -0.9208 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4403   -0.6378    0.2064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7852   -0.9586    0.4245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1434   -2.2789    0.5140 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1676   -3.2838    0.3874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7382    0.0360    0.5479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0478   -0.3332    0.7617 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9692   -0.5712   -0.2827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0906    4.1136   -0.5296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1247    4.0362    1.0174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8863    4.2281    1.0591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7537    2.6884    0.1706 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5303    2.1647   -0.1728 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1509   -0.8215   -0.1883 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0272    1.7243   -0.5420 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4334    0.6258   -1.8927 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1632    0.3941   -0.2749 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0517    0.3908    1.1004 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1174   -1.9561    0.3283 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1651   -3.1979   -0.2356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7103   -1.4286    0.1125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3903   -3.1049    1.1868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6062   -3.1842   -0.5700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5649   -4.2977    0.5159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4457   -0.5565   -1.2714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4765   -1.5318   -0.1489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7350    0.2308   -0.3246 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
  5 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 18 21  2  0
 21 22  1  0
 22 23  1  0
 21  3  1  0
 15 10  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  6 28  1  0
  7 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  0
 12 33  1  0
 13 34  1  0
 14 35  1  0
 17 36  1  0
 20 37  1  0
 20 38  1  0
 20 39  1  0
 23 40  1  0
 23 41  1  0
 23 42  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Piperlongumine	Kegg
5,6-Dihydro-1-(3,4,5-trimethoxycinnamoyl)-2(1H)-pyridinone	HMDB
5,6-Dihydro-1-[1-oxo-3-(3,4,5-trimethoxyphenyl)-2-propenyl]-2(1H)-pyridinone, 9ci	HMDB
N-(3,4,5-Trimethoxycinnamoyl)-D3-piperidin-2-one	HMDB
Piperlonguminine	HMDB

Chemical Formula

C₁₇H₁₉NO₅

Average Molecular Weight

317.3365

Monoisotopic Molecular Weight

317.126322723

IUPAC Name

1-[(2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]-1,2,5,6-tetrahydropyridin-2-one

Traditional Name

piperlongumine

CAS Registry Number

20069-09-4

SMILES

COC1=CC(\C=C\C(=O)N2CCC=CC2=O)=CC(OC)=C1OC

InChI Identifier

InChI=1S/C17H19NO5/c1-21-13-10-12(11-14(22-2)17(13)23-3)7-8-16(20)18-9-5-4-6-15(18)19/h4,6-8,10-11H,5,9H2,1-3H3/b8-7+

InChI Key

VABYUUZNAVQNPG-BQYQJAHWSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cinnamic acids and derivatives. These are organic aromatic compounds containing a benzene and a carboxylic acid group (or a derivative thereof) forming 3-phenylprop-2-enoic acid.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Not Available

Direct Parent

Cinnamic acids and derivatives

Alternative Parents

Substituents

Cinnamic acid or derivatives
Phenoxy compound
Anisole
Methoxybenzene
Styrene
Phenol ether
Alkyl aryl ether
Monocyclic benzene moiety
Hydropyridine
Benzenoid
Carboxylic acid imide, n-substituted
Carboxylic acid imide
Dicarboximide
Carboxylic acid derivative
Azacycle
Ether
Organoheterocyclic compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Organic nitrogen compound
Carbonyl group
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

cinnamamides (CHEBI:8241 )
Piperidine alkaloids (C10166 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cytoplasm (FooDB: )
Extracellular (FooDB: )

Route of exposure

Enteral

Ingestion (FooDB: )

Source

Endogenous

Endogenous (FooDB: )

Plant

Plant (FooDB: )

Exogenous

Food

Food (FooDB: )

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Antineoplastic agent

Anticancer agent (FooDB: )

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	124 °C	Not Available
Boiling Point	475.61 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	1030 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	2.340 (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	176.149	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001468

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.044 g/L	ALOGPS
logP	2.32	ALOGPS
logP	1.74	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	17.77	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	65.07 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	87.32 m³·mol⁻¹	ChemAxon
Polarizability	33.45 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	177.024	31661259
DarkChem	[M-H]-	174.343	31661259
DeepCCS	[M+H]+	172.773	30932474
DeepCCS	[M-H]-	170.415	30932474
DeepCCS	[M-2H]-	203.641	30932474
DeepCCS	[M+Na]+	178.868	30932474
AllCCS	[M+H]+	175.0	32859911
AllCCS	[M+H-H2O]+	171.7	32859911
AllCCS	[M+NH4]+	178.0	32859911
AllCCS	[M+Na]+	178.9	32859911
AllCCS	[M-H]-	177.5	32859911
AllCCS	[M+Na-2H]-	177.6	32859911
AllCCS	[M+HCOO]-	177.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Piplartine	COC1=CC(\C=C\C(=O)N2CCC=CC2=O)=CC(OC)=C1OC	4216.7	Standard polar	33892256
Piplartine	COC1=CC(\C=C\C(=O)N2CCC=CC2=O)=CC(OC)=C1OC	2658.2	Standard non polar	33892256
Piplartine	COC1=CC(\C=C\C(=O)N2CCC=CC2=O)=CC(OC)=C1OC	2834.3	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 - Piplartine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f6x-8696000000-1b169be7f9827d7d5bb9	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Piplartine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Piplartine LC-ESI-qTof , Positive-QTOF	splash10-006x-2920000000-d1b540d4ec0c4f0488b5	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Piplartine , positive-QTOF	splash10-006x-2920000000-d1b540d4ec0c4f0488b5	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Piplartine 6V, Positive-QTOF	splash10-00xr-0095000000-893ac7feee23d135f48f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Piplartine 6V, Positive-QTOF	splash10-00di-0490000000-9bfa59dabc3856292b2d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Piplartine 6V, Positive-QTOF	splash10-00xr-0095000000-9ce911783fc7fee41f72	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Piplartine 6V, Positive-QTOF	splash10-00di-0691000000-f25b002ae4f7d0b949c4	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Piplartine 10V, Positive-QTOF	splash10-00xr-0094000000-893ac7feee23d135f48f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Piplartine 10V, Positive-QTOF	splash10-00di-0490000000-1caef8816d72c8b3ed31	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Piplartine 50V, Positive-QTOF	splash10-01p2-1900000000-78c9457ea36bb5f39548	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Piplartine 10V, Positive-QTOF	splash10-00di-0094000000-f13710ea1ae4605875e6	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Piplartine 30V, Positive-QTOF	splash10-0006-0920000000-3b5ae74c1ff52ea177e2	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Piplartine 10V, Positive-QTOF	splash10-00di-0490000000-b037dc0f31c179d7ffcf	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Piplartine 10V, Positive-QTOF	splash10-00xr-0095000000-90ecae44d143ba28ff4e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Piplartine 10V, Positive-QTOF	splash10-00di-0691000000-3919a66965da314b796b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Piplartine 30V, Positive-QTOF	splash10-0006-0920000000-036fa5848d79b8e9cc7b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Piplartine 50V, Positive-QTOF	splash10-0f72-1900000000-2f07ed81f41453d1345b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Piplartine 6V, Positive-QTOF	splash10-0f72-1900000000-926af03c5b2bb1c4be9d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Piplartine 6V, Positive-QTOF	splash10-0006-0920000000-ee6613da7c274bef4f9a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Piplartine 50V, Positive-QTOF	splash10-0o6r-1900000000-159da23824e105e3f5bf	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piplartine 10V, Positive-QTOF	splash10-014i-3129000000-e8f337c9dcd6328a666a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piplartine 20V, Positive-QTOF	splash10-00r2-9766000000-04c2336d1dc5322a75b5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piplartine 40V, Positive-QTOF	splash10-0gwf-9820000000-e13571d089d563c5dfc7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piplartine 10V, Negative-QTOF	splash10-014i-0019000000-31c4ea7df9de2482d546	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piplartine 20V, Negative-QTOF	splash10-014j-9278000000-870683a5557a7e8eac4e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piplartine 40V, Negative-QTOF	splash10-0002-9110000000-bac2f04584920167606f	2016-08-03	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	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

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

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

Piperlongumine

METLIN ID

Not Available

PubChem Compound

637858

PDB ID

Not Available

ChEBI ID

564921

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1672441

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Kong EH, Kim YJ, Kim YJ, Cho HJ, Yu SN, Kim KY, Chang JH, Ahn SC: Piplartine induces caspase-mediated apoptosis in PC-3 human prostate cancer cells. Oncol Rep. 2008 Oct;20(4):785-92. [PubMed:18813819 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Piplartine (HMDB0030341)

MOL for HMDB0030341 (Piplartine)

3D MOL for HMDB0030341 (Piplartine)

3D SDF for HMDB0030341 (Piplartine)

3D-SDF for HMDB0030341 (Piplartine)

PDB for HMDB0030341 (Piplartine)

3D PDB for HMDB0030341 (Piplartine)

SMILES for HMDB0030341 (Piplartine)

INCHI for HMDB0030341 (Piplartine)

Structure for HMDB0030341 (Piplartine)

3D Structure for HMDB0030341 (Piplartine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra