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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 17:35:21 UTC

Update Date

2022-09-22 18:35:09 UTC

HMDB ID

HMDB0030187

Secondary Accession Numbers

HMDB30187

Metabolite Identification

Common Name

(E,E)-Piperlonguminine

Description

(E,E)-Piperlonguminine, also known as piperlongumine, belongs to the class of organic compounds known as benzodioxoles. These are organic compounds containing a benzene ring fused to either isomers of dioxole. Dioxole is a five-membered unsaturated ring of two oxygen atoms and three carbon atoms (E,E)-Piperlonguminine has been detected, but not quantified in, herbs and spices. This could make (e,e)-piperlonguminine a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on (E,E)-Piperlonguminine.

Structure

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

HMDB0030187
     RDKit          3D
(E,E)-Piperlonguminine
 39 40  0  0  0  0  0  0  0  0999 V2000
   -4.4936   -2.2118    0.3391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6546   -1.0438    1.2501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1074   -0.7938    1.5364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0941    0.2239    0.6233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6924    0.0678    0.3568 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9597    1.1018    0.6160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5718    2.2641    1.1175 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5514    1.0497    0.3984 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1619    2.1370    0.6856 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5158    2.1129    0.4944 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7243    2.0915    0.3238 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6264    1.1381   -0.1659 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0020    1.4103   -0.2553 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8638    0.5341   -0.8232 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4104   -0.6677   -1.3366 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0706   -0.9456   -1.2527 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1998   -0.0718   -0.6841 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8649   -2.1970   -1.8290 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0945   -2.7834   -2.1317 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0203   -1.7325   -1.9591 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6007   -3.1852    0.8514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4846   -2.2100   -0.1586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2700   -2.2234   -0.4798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0831   -1.2736    2.1836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5224   -1.5990    2.2126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6589   -0.7761    0.5761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2878    0.1938    2.0150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6993    0.4578   -0.2660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2460    1.0450    1.3329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6492    2.2872    2.1431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0798    0.1687    0.0181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4259    2.9980    1.0884 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5290    3.4108   -0.0362 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2219    2.9905    0.8347 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3402    2.3651    0.1545 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9221    0.7361   -0.8978 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1504   -0.3061   -0.6254 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2592   -3.6074   -1.3969 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1552   -3.1560   -3.1882 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 17 12  1  0
 20 15  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  3 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  7 30  1  0
  8 31  1  0
  9 32  1  0
 10 33  1  0
 11 34  1  0
 13 35  1  0
 14 36  1  0
 17 37  1  0
 19 38  1  0
 19 39  1  0
M  END


  Mrv0541 05061305032D          

 20 21  0  0  0  0            999 V2000
    8.2802   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8513   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1368   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1368   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5658   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5658   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8513   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8513   -2.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5658   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0  0  0  0
  5  3  2  0  0  0  0
  6  4  2  0  0  0  0
  8  7  2  0  0  0  0
 12  1  1  0  0  0  0
 12  2  1  0  0  0  0
 12 10  1  0  0  0  0
 13  5  1  0  0  0  0
 13  7  1  0  0  0  0
 13  9  2  0  0  0  0
 14  8  1  0  0  0  0
 15  9  1  0  0  0  0
 15 14  2  0  0  0  0
 16  6  1  0  0  0  0
 17 10  1  0  0  0  0
 17 16  2  0  0  0  0
 18 16  1  0  0  0  0
 19 11  1  0  0  0  0
 19 14  1  0  0  0  0
 20 11  1  0  0  0  0
 20 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030187

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)C\N=C(/O)\C=C\C=C\C1=CC2=C(OCO2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H19NO3/c1-12(2)10-17-16(18)6-4-3-5-13-7-8-14-15(9-13)20-11-19-14/h3-9,12H,10-11H2,1-2H3,(H,17,18)/b5-3+,6-4+

> <INCHI_KEY>
WHAAPCGHVWVUEX-GGWOSOGESA-N

> <FORMULA>
C16H19NO3

> <MOLECULAR_WEIGHT>
273.327

> <EXACT_MASS>
273.136493479

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
31.448206446391726

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(Z,2E,4E)-5-(2H-1,3-benzodioxol-5-yl)-N-(2-methylpropyl)penta-2,4-dienimidic acid

> <ALOGPS_LOGP>
3.58

> <JCHEM_LOGP>
3.767176156

> <ALOGPS_LOGS>
-4.66

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.722105029885321

> <JCHEM_PKA_STRONGEST_BASIC>
4.993582043519771

> <JCHEM_POLAR_SURFACE_AREA>
51.05000000000001

> <JCHEM_REFRACTIVITY>
80.1302

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.00e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(Z,2E,4E)-5-(2H-1,3-benzodioxol-5-yl)-N-(2-methylpropyl)penta-2,4-dienimidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030187
     RDKit          3D
(E,E)-Piperlonguminine
 39 40  0  0  0  0  0  0  0  0999 V2000
   -4.4936   -2.2118    0.3391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6546   -1.0438    1.2501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1074   -0.7938    1.5364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0941    0.2239    0.6233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6924    0.0678    0.3568 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9597    1.1018    0.6160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5718    2.2641    1.1175 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5514    1.0497    0.3984 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1619    2.1370    0.6856 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5158    2.1129    0.4944 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7243    2.0915    0.3238 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6264    1.1381   -0.1659 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0020    1.4103   -0.2553 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8638    0.5341   -0.8232 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4104   -0.6677   -1.3366 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0706   -0.9456   -1.2527 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1998   -0.0718   -0.6841 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8649   -2.1970   -1.8290 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0945   -2.7834   -2.1317 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0203   -1.7325   -1.9591 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6007   -3.1852    0.8514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4846   -2.2100   -0.1586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2700   -2.2234   -0.4798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0831   -1.2736    2.1836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5224   -1.5990    2.2126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6589   -0.7761    0.5761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2878    0.1938    2.0150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6993    0.4578   -0.2660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2460    1.0450    1.3329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6492    2.2872    2.1431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0798    0.1687    0.0181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4259    2.9980    1.0884 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5290    3.4108   -0.0362 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2219    2.9905    0.8347 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3402    2.3651    0.1545 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9221    0.7361   -0.8978 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1504   -0.3061   -0.6254 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2592   -3.6074   -1.3969 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1552   -3.1560   -3.1882 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 17 12  1  0
 20 15  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  3 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  7 30  1  0
  8 31  1  0
  9 32  1  0
 10 33  1  0
 11 34  1  0
 13 35  1  0
 14 36  1  0
 17 37  1  0
 19 38  1  0
 19 39  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      15.456  -7.700   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.789  -7.700   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.122   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.455  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.788  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.455  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      14.123  -5.390   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      14.123  -6.930   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.454   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.789  -3.080   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0      12.789  -4.620   0.000  0.00  0.00           N+0
HETATM   18  O   UNK     0      14.123  -2.310   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       3.322   2.016   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       3.322  -0.476   0.000  0.00  0.00           O+0
CONECT    1   12                                                            
CONECT    2   12                                                            
CONECT    3    4    5                                                       
CONECT    4    3    6                                                       
CONECT    5    3   13                                                       
CONECT    6    4   16                                                       
CONECT    7    8   13                                                       
CONECT    8    7   14                                                       
CONECT    9   13   15                                                       
CONECT   10   12   17                                                       
CONECT   11   19   20                                                       
CONECT   12    1    2   10                                                  
CONECT   13    5    7    9                                                  
CONECT   14    8   15   19                                                  
CONECT   15    9   14   20                                                  
CONECT   16    6   17   18                                                  
CONECT   17   10   16                                                       
CONECT   18   16                                                            
CONECT   19   11   14                                                       
CONECT   20   11   15                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

COMPND    HMDB0030187
HETATM    1  C1  UNL     1      -4.494  -2.212   0.339  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.655  -1.044   1.250  1.00  0.00           C  
HETATM    3  C3  UNL     1      -6.107  -0.794   1.536  1.00  0.00           C  
HETATM    4  C4  UNL     1      -4.094   0.224   0.623  1.00  0.00           C  
HETATM    5  N1  UNL     1      -2.692   0.068   0.357  1.00  0.00           N  
HETATM    6  C5  UNL     1      -1.960   1.102   0.616  1.00  0.00           C  
HETATM    7  O1  UNL     1      -2.572   2.264   1.117  1.00  0.00           O  
HETATM    8  C6  UNL     1      -0.551   1.050   0.398  1.00  0.00           C  
HETATM    9  C7  UNL     1       0.162   2.137   0.686  1.00  0.00           C  
HETATM   10  C8  UNL     1       1.516   2.113   0.494  1.00  0.00           C  
HETATM   11  C9  UNL     1       2.724   2.092   0.324  1.00  0.00           C  
HETATM   12  C10 UNL     1       3.626   1.138  -0.166  1.00  0.00           C  
HETATM   13  C11 UNL     1       5.002   1.410  -0.255  1.00  0.00           C  
HETATM   14  C12 UNL     1       5.864   0.534  -0.823  1.00  0.00           C  
HETATM   15  C13 UNL     1       5.410  -0.668  -1.337  1.00  0.00           C  
HETATM   16  C14 UNL     1       4.071  -0.946  -1.253  1.00  0.00           C  
HETATM   17  C15 UNL     1       3.200  -0.072  -0.684  1.00  0.00           C  
HETATM   18  O2  UNL     1       3.865  -2.197  -1.829  1.00  0.00           O  
HETATM   19  C16 UNL     1       5.094  -2.783  -2.132  1.00  0.00           C  
HETATM   20  O3  UNL     1       6.020  -1.732  -1.959  1.00  0.00           O  
HETATM   21  H1  UNL     1      -4.601  -3.185   0.851  1.00  0.00           H  
HETATM   22  H2  UNL     1      -3.485  -2.210  -0.159  1.00  0.00           H  
HETATM   23  H3  UNL     1      -5.270  -2.223  -0.480  1.00  0.00           H  
HETATM   24  H4  UNL     1      -4.083  -1.274   2.184  1.00  0.00           H  
HETATM   25  H5  UNL     1      -6.522  -1.599   2.213  1.00  0.00           H  
HETATM   26  H6  UNL     1      -6.659  -0.776   0.576  1.00  0.00           H  
HETATM   27  H7  UNL     1      -6.288   0.194   2.015  1.00  0.00           H  
HETATM   28  H8  UNL     1      -4.699   0.458  -0.266  1.00  0.00           H  
HETATM   29  H9  UNL     1      -4.246   1.045   1.333  1.00  0.00           H  
HETATM   30  H10 UNL     1      -2.649   2.287   2.143  1.00  0.00           H  
HETATM   31  H11 UNL     1      -0.080   0.169   0.018  1.00  0.00           H  
HETATM   32  H12 UNL     1      -0.426   2.998   1.088  1.00  0.00           H  
HETATM   33  H13 UNL     1       1.529   3.411  -0.036  1.00  0.00           H  
HETATM   34  H14 UNL     1       3.222   2.990   0.835  1.00  0.00           H  
HETATM   35  H15 UNL     1       5.340   2.365   0.155  1.00  0.00           H  
HETATM   36  H16 UNL     1       6.922   0.736  -0.898  1.00  0.00           H  
HETATM   37  H17 UNL     1       2.150  -0.306  -0.625  1.00  0.00           H  
HETATM   38  H18 UNL     1       5.259  -3.607  -1.397  1.00  0.00           H  
HETATM   39  H19 UNL     1       5.155  -3.156  -3.188  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3    4   24
CONECT    3   25   26   27
CONECT    4    5   28   29
CONECT    5    6    6
CONECT    6    7    8
CONECT    7   30
CONECT    8    9    9   31
CONECT    9   10   32
CONECT   10   11   11   33
CONECT   11   12   34
CONECT   12   13   13   17
CONECT   13   14   35
CONECT   14   15   15   36
CONECT   15   16   20
CONECT   16   17   17   18
CONECT   17   37
CONECT   18   19
CONECT   19   20   38   39
END

HMDB0030187
     RDKit          3D
(E,E)-Piperlonguminine
 39 40  0  0  0  0  0  0  0  0999 V2000
   -4.4936   -2.2118    0.3391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6546   -1.0438    1.2501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1074   -0.7938    1.5364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0941    0.2239    0.6233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6924    0.0678    0.3568 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9597    1.1018    0.6160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5718    2.2641    1.1175 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5514    1.0497    0.3984 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1619    2.1370    0.6856 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5158    2.1129    0.4944 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7243    2.0915    0.3238 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6264    1.1381   -0.1659 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0020    1.4103   -0.2553 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8638    0.5341   -0.8232 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4104   -0.6677   -1.3366 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0706   -0.9456   -1.2527 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1998   -0.0718   -0.6841 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8649   -2.1970   -1.8290 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0945   -2.7834   -2.1317 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0203   -1.7325   -1.9591 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6007   -3.1852    0.8514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4846   -2.2100   -0.1586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2700   -2.2234   -0.4798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0831   -1.2736    2.1836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5224   -1.5990    2.2126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6589   -0.7761    0.5761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2878    0.1938    2.0150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6993    0.4578   -0.2660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2460    1.0450    1.3329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6492    2.2872    2.1431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0798    0.1687    0.0181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4259    2.9980    1.0884 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5290    3.4108   -0.0362 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2219    2.9905    0.8347 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3402    2.3651    0.1545 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9221    0.7361   -0.8978 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1504   -0.3061   -0.6254 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2592   -3.6074   -1.3969 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1552   -3.1560   -3.1882 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 17 12  1  0
 20 15  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  3 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  7 30  1  0
  8 31  1  0
  9 32  1  0
 10 33  1  0
 11 34  1  0
 13 35  1  0
 14 36  1  0
 17 37  1  0
 19 38  1  0
 19 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(2E,4E)-5-(2H-1,3-Benzodioxol-5-yl)-N-(2-methylpropyl)penta-2,4-dienimidate	HMDB
Piperlonguminine	HMDB
Piperlongumine	HMDB

Chemical Formula

C₁₆H₁₉NO₃

Average Molecular Weight

273.327

Monoisotopic Molecular Weight

273.136493479

IUPAC Name

(Z,2E,4E)-5-(2H-1,3-benzodioxol-5-yl)-N-(2-methylpropyl)penta-2,4-dienimidic acid

Traditional Name

(Z,2E,4E)-5-(2H-1,3-benzodioxol-5-yl)-N-(2-methylpropyl)penta-2,4-dienimidic acid

CAS Registry Number

5950-12-9

SMILES

CC(C)C\N=C(/O)\C=C\C=C\C1=CC2=C(OCO2)C=C1

InChI Identifier

InChI=1S/C16H19NO3/c1-12(2)10-17-16(18)6-4-3-5-13-7-8-14-15(9-13)20-11-19-14/h3-9,12H,10-11H2,1-2H3,(H,17,18)/b5-3+,6-4+

InChI Key

WHAAPCGHVWVUEX-GGWOSOGESA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzodioxoles. These are organic compounds containing a benzene ring fused to either isomers of dioxole. Dioxole is a five-membered unsaturated ring of two oxygen atoms and three carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzodioxoles

Sub Class

Not Available

Direct Parent

Benzodioxoles

Alternative Parents

Substituents

Benzodioxole
Styrene
N-acyl-amine
Benzenoid
Carboxamide group
Secondary carboxylic acid amide
Carboxylic acid derivative
Acetal
Oxacycle
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Carbonyl group
Organic nitrogen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030187)

Source

Endogenous

Endogenous (HMDB: HMDB0030187)

Plant

Plant (HMDB: HMDB0030187)

Exogenous

Food

Food (HMDB: HMDB0030187)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Exogenous (HMDB: HMDB0030187)

Process

Naturally occurring process

Biological process

Cellular process

Cell signaling (HMDB: HMDB0030187)

Role

Biological role

Energy source (HMDB: HMDB0030187)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0030187)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	167 - 169 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	17.36 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.006 g/L	ALOGPS
logP	3.58	ALOGPS
logP	3.77	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	7.72	ChemAxon
pKa (Strongest Basic)	4.99	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	51.05 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	80.13 m³·mol⁻¹	ChemAxon
Polarizability	31.45 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
DeepCCS	[M+H]+	171.236	30932474
DeepCCS	[M-H]-	168.878	30932474
DeepCCS	[M-2H]-	201.764	30932474
DeepCCS	[M+Na]+	177.33	30932474
AllCCS	[M+H]+	164.2	32859911
AllCCS	[M+H-H2O]+	160.7	32859911
AllCCS	[M+NH4]+	167.5	32859911
AllCCS	[M+Na]+	168.4	32859911
AllCCS	[M-H]-	169.7	32859911
AllCCS	[M+Na-2H]-	169.7	32859911
AllCCS	[M+HCOO]-	169.9	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022.	6.35 minutes	32390414
Predicted by Siyang on May 30, 2022	15.1345 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.11 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	24.8 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2364.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	408.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	181.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	218.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	148.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	647.7 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	614.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	81.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1328.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	517.8 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1527.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	424.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	404.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	340.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	365.0 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(E,E)-Piperlonguminine	CC(C)C\N=C(/O)\C=C\C=C\C1=CC2=C(OCO2)C=C1	3787.8	Standard polar	33892256
(E,E)-Piperlonguminine	CC(C)C\N=C(/O)\C=C\C=C\C1=CC2=C(OCO2)C=C1	2247.1	Standard non polar	33892256
(E,E)-Piperlonguminine	CC(C)C\N=C(/O)\C=C\C=C\C1=CC2=C(OCO2)C=C1	2513.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(E,E)-Piperlonguminine,1TMS,isomer #1	CC(C)C/N=C(/C=C/C=C/C1=CC=C2OCOC2=C1)O[Si](C)(C)C	2451.2	Semi standard non polar	33892256
(E,E)-Piperlonguminine,1TBDMS,isomer #1	CC(C)C/N=C(/C=C/C=C/C1=CC=C2OCOC2=C1)O[Si](C)(C)C(C)(C)C	2661.2	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (E,E)-Piperlonguminine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udl-4290000000-427cd8f96702f4d87b60	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (E,E)-Piperlonguminine GC-MS (1 TMS) - 70eV, Positive	splash10-05fr-9375000000-df52f1f3e0600e0192c6	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (E,E)-Piperlonguminine 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 - (E,E)-Piperlonguminine LC-ESI-qTof , Positive-QTOF	splash10-0udi-0690000000-aa4a8e7d85b84fc68ba6	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (E,E)-Piperlonguminine , positive-QTOF	splash10-00kr-0910000000-2e88b4e4a73fd8b3c4ab	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (E,E)-Piperlonguminine 0V, Positive-QTOF	splash10-00di-0090000000-2c5137df36f0ce8b47f6	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (E,E)-Piperlonguminine 30V, Positive-QTOF	splash10-0a4r-4910000000-d0a82a1892f058f45b67	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (E,E)-Piperlonguminine 0V, Positive-QTOF	splash10-00di-0090000000-5c4aa81e45c8f50e6534	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (E,E)-Piperlonguminine 10V, Positive-QTOF	splash10-00di-0190000000-684772db3f325d77e9b4	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (E,E)-Piperlonguminine 30V, Positive-QTOF	splash10-052r-5910000000-3670d53479869ebd58d1	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (E,E)-Piperlonguminine 10V, Positive-QTOF	splash10-00di-0290000000-ce08f32a865fc569c4f3	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E,E)-Piperlonguminine 10V, Positive-QTOF	splash10-00di-9140000000-e2b9ff384b615e68e484	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E,E)-Piperlonguminine 20V, Positive-QTOF	splash10-00di-9000000000-ce265384b494297a7233	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E,E)-Piperlonguminine 40V, Positive-QTOF	splash10-0a4i-9000000000-a7a86f1ff4ed9259c1c7	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E,E)-Piperlonguminine 10V, Negative-QTOF	splash10-00di-0090000000-25db048f484dbe4caff5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E,E)-Piperlonguminine 20V, Negative-QTOF	splash10-00di-4690000000-73a43e1e711ef3fcecfd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E,E)-Piperlonguminine 40V, Negative-QTOF	splash10-00dm-7910000000-0a3050421629ca7cf18f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E,E)-Piperlonguminine 10V, Positive-QTOF	splash10-00di-0090000000-4aad5806e19a0e184d44	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E,E)-Piperlonguminine 20V, Positive-QTOF	splash10-0h90-2790000000-99eac5e0140f785c8718	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E,E)-Piperlonguminine 40V, Positive-QTOF	splash10-00di-3910000000-609e969720c31ae23e44	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E,E)-Piperlonguminine 10V, Negative-QTOF	splash10-00di-0090000000-9a5ec9d1a8133eb07575	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E,E)-Piperlonguminine 20V, Negative-QTOF	splash10-00di-0290000000-45b698369ecf633548f9	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E,E)-Piperlonguminine 40V, Negative-QTOF	splash10-006t-2910000000-0c3f1dbd52589070c55e	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

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	Adult (>18 years old)	Both	Asthma	33739820	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Asthma	33739820	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

FDB002005

KNApSAcK ID

C00042857

Chemspider ID

4478660

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5320621

PDB ID

Not Available

ChEBI ID

520668

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1771521

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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

Showing metabocard for (E,E)-Piperlonguminine (HMDB0030187)

MOL for HMDB0030187 ((E,E)-Piperlonguminine)

3D MOL for HMDB0030187 ((E,E)-Piperlonguminine)

3D SDF for HMDB0030187 ((E,E)-Piperlonguminine)

3D-SDF for HMDB0030187 ((E,E)-Piperlonguminine)

PDB for HMDB0030187 ((E,E)-Piperlonguminine)

3D PDB for HMDB0030187 ((E,E)-Piperlonguminine)

SMILES for HMDB0030187 ((E,E)-Piperlonguminine)

INCHI for HMDB0030187 ((E,E)-Piperlonguminine)

Structure for HMDB0030187 ((E,E)-Piperlonguminine)

3D Structure for HMDB0030187 ((E,E)-Piperlonguminine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra