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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 03:10:43 UTC

Update Date

2022-03-07 02:57:02 UTC

HMDB ID

HMDB0041488

Secondary Accession Numbers

HMDB41488

Metabolite Identification

Common Name

4,5-Dihydropiperlonguminine

Description

4,5-Dihydropiperlonguminine 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. 4,5-Dihydropiperlonguminine has been detected, but not quantified in, herbs and spices. This could make 4,5-dihydropiperlonguminine a potential biomarker for the consumption of these foods. Based on a literature review a small amount of articles have been published on 4,5-Dihydropiperlonguminine.

Structure

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

HMDB0041488
     RDKit          3D
4,5-Dihydropiperlonguminine
 41 42  0  0  0  0  0  0  0  0999 V2000
   -6.9708   -0.8309    0.2810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5480   -0.4335    0.6950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4590    1.0437    0.9532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6296   -0.8152   -0.4286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2774   -0.4722   -0.1111 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2476   -0.7492   -1.0419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5479   -1.2929   -2.1313 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8770   -0.3986   -0.7138 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1316   -0.6271   -1.5324 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5100   -0.2893   -1.2344 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7676    0.3519    0.0808 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2552    0.6049    0.1594 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8027    1.7764   -0.2864 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1600    1.9726   -0.1994 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9977    1.0066    0.3330 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4484   -0.1725    0.7819 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0938   -0.3519    0.6878 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5054   -0.9675    1.2669 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7123   -0.3973    0.7361 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3785    0.9626    0.5289 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9995   -1.9419    0.3916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7168   -0.3617    0.9379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1149   -0.6000   -0.7852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3322   -1.0165    1.6043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5396    1.6059    0.0110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5234    1.2459    1.5136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2874    1.3069    1.6734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6770   -1.9115   -0.6144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9104   -0.3073   -1.3713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0775   -0.0169    0.8174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6585    0.0644    0.2254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0930   -1.0939   -2.4780 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8686    0.4246   -2.0280 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1370   -1.1837   -1.3354 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5255   -0.2462    0.9566 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2852    1.3441    0.2014 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1366    2.5326   -0.7045 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5981    2.9108   -0.5565 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6776   -1.2950    1.0499 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9318   -0.8487   -0.2609 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5639   -0.5323    1.4184 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  1  0
  6  7  2  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  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
  5 30  1  0
  8 31  1  0
  9 32  1  0
 10 33  1  0
 10 34  1  0
 11 35  1  0
 11 36  1  0
 13 37  1  0
 14 38  1  0
 17 39  1  0
 19 40  1  0
 19 41  1  0
M  END


  Mrv0541 02241210482D          

 20 21  0  0  0  0            999 V2000
   -2.5803    0.4111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8665   -0.0014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8665   -0.8264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5803   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2939   -0.8264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2939   -0.0014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0804    0.2529    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5644   -0.4153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0804   -1.0821    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1515    0.4111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4379   -0.0014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2771    0.4111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9921   -0.0014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7057    0.4111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7057    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4207   -0.0014    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1344    0.4111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8494   -0.8264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8494   -0.0014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5644    0.4111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  2  0  0  0  0
  2  3  2  0  0  0  0
  2 10  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  5  9  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 19  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0041488

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)CNC(=O)\C=C\CCC1=CC=C2OCOC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H21NO3/c1-12(2)10-17-16(18)6-4-3-5-13-7-8-14-15(9-13)20-11-19-14/h4,6-9,12H,3,5,10-11H2,1-2H3,(H,17,18)/b6-4+

> <INCHI_KEY>
CSGDXLXTJVRNEA-GQCTYLIASA-N

> <FORMULA>
C16H21NO3

> <MOLECULAR_WEIGHT>
275.3428

> <EXACT_MASS>
275.152143543

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
31.76725673496084

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-5-(2H-1,3-benzodioxol-5-yl)-N-(2-methylpropyl)pent-2-enamide

> <ALOGPS_LOGP>
3.27

> <JCHEM_LOGP>
3.226793685666667

> <ALOGPS_LOGS>
-4.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.508281064792207

> <JCHEM_PKA_STRONGEST_BASIC>
2.3463140797056727

> <JCHEM_POLAR_SURFACE_AREA>
47.56

> <JCHEM_REFRACTIVITY>
78.49190000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.34e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-5-(2H-1,3-benzodioxol-5-yl)-N-(2-methylpropyl)pent-2-enamide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0041488
     RDKit          3D
4,5-Dihydropiperlonguminine
 41 42  0  0  0  0  0  0  0  0999 V2000
   -6.9708   -0.8309    0.2810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5480   -0.4335    0.6950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4590    1.0437    0.9532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6296   -0.8152   -0.4286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2774   -0.4722   -0.1111 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2476   -0.7492   -1.0419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5479   -1.2929   -2.1313 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8770   -0.3986   -0.7138 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1316   -0.6271   -1.5324 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5100   -0.2893   -1.2344 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7676    0.3519    0.0808 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2552    0.6049    0.1594 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8027    1.7764   -0.2864 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1600    1.9726   -0.1994 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9977    1.0066    0.3330 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4484   -0.1725    0.7819 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0938   -0.3519    0.6878 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5054   -0.9675    1.2669 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7123   -0.3973    0.7361 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3785    0.9626    0.5289 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9995   -1.9419    0.3916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7168   -0.3617    0.9379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1149   -0.6000   -0.7852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3322   -1.0165    1.6043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5396    1.6059    0.0110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5234    1.2459    1.5136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2874    1.3069    1.6734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6770   -1.9115   -0.6144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9104   -0.3073   -1.3713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0775   -0.0169    0.8174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6585    0.0644    0.2254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0930   -1.0939   -2.4780 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8686    0.4246   -2.0280 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1370   -1.1837   -1.3354 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5255   -0.2462    0.9566 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2852    1.3441    0.2014 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1366    2.5326   -0.7045 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5981    2.9108   -0.5565 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6776   -1.2950    1.0499 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9318   -0.8487   -0.2609 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5639   -0.5323    1.4184 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  1  0
  6  7  2  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  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
  5 30  1  0
  8 31  1  0
  9 32  1  0
 10 33  1  0
 10 34  1  0
 11 35  1  0
 11 36  1  0
 13 37  1  0
 14 38  1  0
 17 39  1  0
 19 40  1  0
 19 41  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -4.817   0.767   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.484  -0.003   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.484  -1.543   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.817  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.149  -1.543   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -6.149  -0.003   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -7.617   0.472   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -8.520  -0.775   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -7.617  -2.020   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -2.149   0.767   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.817  -0.003   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.517   0.767   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.852  -0.003   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.184   0.767   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       3.184   2.310   0.000  0.00  0.00           O+0
HETATM   16  N   UNK     0       4.519  -0.003   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0       5.851   0.767   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.186  -1.543   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.186  -0.003   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.520   0.767   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   10                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    9                                                  
CONECT    6    1    5    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    5    8                                                       
CONECT   10    2   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   19                                                       
CONECT   18   19                                                            
CONECT   19   17   18   20                                                  
CONECT   20   19                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

COMPND    HMDB0041488
HETATM    1  C1  UNL     1      -6.971  -0.831   0.281  1.00  0.00           C  
HETATM    2  C2  UNL     1      -5.548  -0.434   0.695  1.00  0.00           C  
HETATM    3  C3  UNL     1      -5.459   1.044   0.953  1.00  0.00           C  
HETATM    4  C4  UNL     1      -4.630  -0.815  -0.429  1.00  0.00           C  
HETATM    5  N1  UNL     1      -3.277  -0.472  -0.111  1.00  0.00           N  
HETATM    6  C5  UNL     1      -2.248  -0.749  -1.042  1.00  0.00           C  
HETATM    7  O1  UNL     1      -2.548  -1.293  -2.131  1.00  0.00           O  
HETATM    8  C6  UNL     1      -0.877  -0.399  -0.714  1.00  0.00           C  
HETATM    9  C7  UNL     1       0.132  -0.627  -1.532  1.00  0.00           C  
HETATM   10  C8  UNL     1       1.510  -0.289  -1.234  1.00  0.00           C  
HETATM   11  C9  UNL     1       1.768   0.352   0.081  1.00  0.00           C  
HETATM   12  C10 UNL     1       3.255   0.605   0.159  1.00  0.00           C  
HETATM   13  C11 UNL     1       3.803   1.776  -0.286  1.00  0.00           C  
HETATM   14  C12 UNL     1       5.160   1.973  -0.199  1.00  0.00           C  
HETATM   15  C13 UNL     1       5.998   1.007   0.333  1.00  0.00           C  
HETATM   16  C14 UNL     1       5.448  -0.172   0.782  1.00  0.00           C  
HETATM   17  C15 UNL     1       4.094  -0.352   0.688  1.00  0.00           C  
HETATM   18  O2  UNL     1       6.505  -0.968   1.267  1.00  0.00           O  
HETATM   19  C16 UNL     1       7.712  -0.397   0.736  1.00  0.00           C  
HETATM   20  O3  UNL     1       7.378   0.963   0.529  1.00  0.00           O  
HETATM   21  H1  UNL     1      -6.999  -1.942   0.392  1.00  0.00           H  
HETATM   22  H2  UNL     1      -7.717  -0.362   0.938  1.00  0.00           H  
HETATM   23  H3  UNL     1      -7.115  -0.600  -0.785  1.00  0.00           H  
HETATM   24  H4  UNL     1      -5.332  -1.016   1.604  1.00  0.00           H  
HETATM   25  H5  UNL     1      -5.540   1.606   0.011  1.00  0.00           H  
HETATM   26  H6  UNL     1      -4.523   1.246   1.514  1.00  0.00           H  
HETATM   27  H7  UNL     1      -6.287   1.307   1.673  1.00  0.00           H  
HETATM   28  H8  UNL     1      -4.677  -1.912  -0.614  1.00  0.00           H  
HETATM   29  H9  UNL     1      -4.910  -0.307  -1.371  1.00  0.00           H  
HETATM   30  H10 UNL     1      -3.077  -0.017   0.817  1.00  0.00           H  
HETATM   31  H11 UNL     1      -0.658   0.064   0.225  1.00  0.00           H  
HETATM   32  H12 UNL     1      -0.093  -1.094  -2.478  1.00  0.00           H  
HETATM   33  H13 UNL     1       1.869   0.425  -2.028  1.00  0.00           H  
HETATM   34  H14 UNL     1       2.137  -1.184  -1.335  1.00  0.00           H  
HETATM   35  H15 UNL     1       1.526  -0.246   0.957  1.00  0.00           H  
HETATM   36  H16 UNL     1       1.285   1.344   0.201  1.00  0.00           H  
HETATM   37  H17 UNL     1       3.137   2.533  -0.704  1.00  0.00           H  
HETATM   38  H18 UNL     1       5.598   2.911  -0.557  1.00  0.00           H  
HETATM   39  H19 UNL     1       3.678  -1.295   1.050  1.00  0.00           H  
HETATM   40  H20 UNL     1       7.932  -0.849  -0.261  1.00  0.00           H  
HETATM   41  H21 UNL     1       8.564  -0.532   1.418  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   30
CONECT    6    7    7    8
CONECT    8    9    9   31
CONECT    9   10   32
CONECT   10   11   33   34
CONECT   11   12   35   36
CONECT   12   13   13   17
CONECT   13   14   37
CONECT   14   15   15   38
CONECT   15   16   20
CONECT   16   17   17   18
CONECT   17   39
CONECT   18   19
CONECT   19   20   40   41
END

HMDB0041488
     RDKit          3D
4,5-Dihydropiperlonguminine
 41 42  0  0  0  0  0  0  0  0999 V2000
   -6.9708   -0.8309    0.2810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5480   -0.4335    0.6950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4590    1.0437    0.9532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6296   -0.8152   -0.4286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2774   -0.4722   -0.1111 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2476   -0.7492   -1.0419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5479   -1.2929   -2.1313 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8770   -0.3986   -0.7138 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1316   -0.6271   -1.5324 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5100   -0.2893   -1.2344 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7676    0.3519    0.0808 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2552    0.6049    0.1594 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8027    1.7764   -0.2864 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1600    1.9726   -0.1994 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9977    1.0066    0.3330 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4484   -0.1725    0.7819 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0938   -0.3519    0.6878 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5054   -0.9675    1.2669 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7123   -0.3973    0.7361 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3785    0.9626    0.5289 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9995   -1.9419    0.3916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7168   -0.3617    0.9379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1149   -0.6000   -0.7852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3322   -1.0165    1.6043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5396    1.6059    0.0110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5234    1.2459    1.5136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2874    1.3069    1.6734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6770   -1.9115   -0.6144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9104   -0.3073   -1.3713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0775   -0.0169    0.8174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6585    0.0644    0.2254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0930   -1.0939   -2.4780 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8686    0.4246   -2.0280 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1370   -1.1837   -1.3354 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5255   -0.2462    0.9566 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2852    1.3441    0.2014 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1366    2.5326   -0.7045 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5981    2.9108   -0.5565 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6776   -1.2950    1.0499 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9318   -0.8487   -0.2609 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5639   -0.5323    1.4184 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  1  0
  6  7  2  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  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
  5 30  1  0
  8 31  1  0
  9 32  1  0
 10 33  1  0
 10 34  1  0
 11 35  1  0
 11 36  1  0
 13 37  1  0
 14 38  1  0
 17 39  1  0
 19 40  1  0
 19 41  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
56-Dihydropiperlonguminine	ChEMBL, HMDB
5-(1,3-Benzodioxol-5-yl)-N-(2-methylpropyl)-2-pentenamide, 9ci	HMDB
Da,b-dihydropiperlonguminine	HMDB
N-Isobutyl-5-(3,4-methylenedioxyphenyl)-2-pentenamide, 8ci	HMDB
(2E)-5-(2H-1,3-Benzodioxol-5-yl)-N-(2-methylpropyl)pent-2-enimidate	Generator
4,5-Dihydropiperlonguminine	MeSH

Chemical Formula

C₁₆H₂₁NO₃

Average Molecular Weight

275.3428

Monoisotopic Molecular Weight

275.152143543

IUPAC Name

(2E)-5-(2H-1,3-benzodioxol-5-yl)-N-(2-methylpropyl)pent-2-enamide

Traditional Name

(2E)-5-(2H-1,3-benzodioxol-5-yl)-N-(2-methylpropyl)pent-2-enamide

CAS Registry Number

23512-53-0

SMILES

CC(C)CNC(=O)\C=C\CCC1=CC=C2OCOC2=C1

InChI Identifier

InChI=1S/C16H21NO3/c1-12(2)10-17-16(18)6-4-3-5-13-7-8-14-15(9-13)20-11-19-14/h4,6-9,12H,3,5,10-11H2,1-2H3,(H,17,18)/b6-4+

InChI Key

CSGDXLXTJVRNEA-GQCTYLIASA-N

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzodioxoles

Sub Class

Not Available

Direct Parent

Benzodioxoles

Alternative Parents

Substituents

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0041488)

Cellular substructure

Extracellular (HMDB: HMDB0041488)
Membrane (HMDB: HMDB0041488)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0041488)

Source

Endogenous

Endogenous (HMDB: HMDB0041488)

Plant

Plant (HMDB: HMDB0041488)

Exogenous

Food

Food (HMDB: HMDB0041488)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Process

Naturally occurring process

Biological process

Cellular process

Cell signaling (HMDB: HMDB0041488)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0041488)

Nutrient

Nutrient (HMDB: HMDB0041488)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0041488)

Emulsifier (HMDB: HMDB0041488)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	110 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.023 g/L	ALOGPS
logP	3.27	ALOGPS
logP	3.23	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	15.51	ChemAxon
pKa (Strongest Basic)	2.35	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	47.56 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	78.49 m³·mol⁻¹	ChemAxon
Polarizability	31.77 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]+	163.716	30932474
DeepCCS	[M-H]-	161.358	30932474
DeepCCS	[M-2H]-	194.244	30932474
DeepCCS	[M+Na]+	169.809	30932474
AllCCS	[M+H]+	165.3	32859911
AllCCS	[M+H-H2O]+	161.9	32859911
AllCCS	[M+NH4]+	168.5	32859911
AllCCS	[M+Na]+	169.4	32859911
AllCCS	[M-H]-	171.2	32859911
AllCCS	[M+Na-2H]-	171.3	32859911
AllCCS	[M+HCOO]-	171.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4,5-Dihydropiperlonguminine	CC(C)CNC(=O)\C=C\CCC1=CC=C2OCOC2=C1	3653.8	Standard polar	33892256
4,5-Dihydropiperlonguminine	CC(C)CNC(=O)\C=C\CCC1=CC=C2OCOC2=C1	2273.0	Standard non polar	33892256
4,5-Dihydropiperlonguminine	CC(C)CNC(=O)\C=C\CCC1=CC=C2OCOC2=C1	2408.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4,5-Dihydropiperlonguminine,1TMS,isomer #1	CC(C)CN(C(=O)/C=C/CCC1=CC=C2OCOC2=C1)[Si](C)(C)C	2331.5	Semi standard non polar	33892256
4,5-Dihydropiperlonguminine,1TMS,isomer #1	CC(C)CN(C(=O)/C=C/CCC1=CC=C2OCOC2=C1)[Si](C)(C)C	2386.9	Standard non polar	33892256
4,5-Dihydropiperlonguminine,1TBDMS,isomer #1	CC(C)CN(C(=O)/C=C/CCC1=CC=C2OCOC2=C1)[Si](C)(C)C(C)(C)C	2523.1	Semi standard non polar	33892256
4,5-Dihydropiperlonguminine,1TBDMS,isomer #1	CC(C)CN(C(=O)/C=C/CCC1=CC=C2OCOC2=C1)[Si](C)(C)C(C)(C)C	2590.7	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4,5-Dihydropiperlonguminine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udr-3790000000-be7b8f1947dad2849620	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4,5-Dihydropiperlonguminine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,5-Dihydropiperlonguminine 10V, Positive-QTOF	splash10-056r-7090000000-2dbec725f383df18b65f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,5-Dihydropiperlonguminine 20V, Positive-QTOF	splash10-0a4i-9110000000-b1288cd44074565efef3	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,5-Dihydropiperlonguminine 40V, Positive-QTOF	splash10-0a4i-9100000000-d3a26ada8655ef65598f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,5-Dihydropiperlonguminine 10V, Negative-QTOF	splash10-00di-0090000000-736af215e74a895a14d8	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,5-Dihydropiperlonguminine 20V, Negative-QTOF	splash10-00di-5490000000-f3dfb53408668ecd0d0b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,5-Dihydropiperlonguminine 40V, Negative-QTOF	splash10-00dl-9520000000-eee0df9028ef56f4f715	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,5-Dihydropiperlonguminine 10V, Negative-QTOF	splash10-00di-0090000000-74dd643ca4390458802e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,5-Dihydropiperlonguminine 20V, Negative-QTOF	splash10-00di-0190000000-ea117276dd5c5ad30744	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,5-Dihydropiperlonguminine 40V, Negative-QTOF	splash10-006t-2910000000-c1503d02c3b72acbf6d0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,5-Dihydropiperlonguminine 10V, Positive-QTOF	splash10-004i-0190000000-c31c416e2788c3ca5ea7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,5-Dihydropiperlonguminine 20V, Positive-QTOF	splash10-0pdi-5890000000-572eee2cb5c5f52b4e31	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,5-Dihydropiperlonguminine 40V, Positive-QTOF	splash10-0a4i-9810000000-4206cb45b18c182e58eb	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB021456

KNApSAcK ID

C00054290

Chemspider ID

22914129

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12682184

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

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 4,5-Dihydropiperlonguminine (HMDB0041488)

MOL for HMDB0041488 (4,5-Dihydropiperlonguminine)

3D MOL for HMDB0041488 (4,5-Dihydropiperlonguminine)

3D SDF for HMDB0041488 (4,5-Dihydropiperlonguminine)

3D-SDF for HMDB0041488 (4,5-Dihydropiperlonguminine)

PDB for HMDB0041488 (4,5-Dihydropiperlonguminine)

3D PDB for HMDB0041488 (4,5-Dihydropiperlonguminine)

SMILES for HMDB0041488 (4,5-Dihydropiperlonguminine)

INCHI for HMDB0041488 (4,5-Dihydropiperlonguminine)

Structure for HMDB0041488 (4,5-Dihydropiperlonguminine)

3D Structure for HMDB0041488 (4,5-Dihydropiperlonguminine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra