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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 02:24:00 UTC

Update Date

2022-03-07 02:56:44 UTC

HMDB ID

HMDB0040811

Secondary Accession Numbers

HMDB40811

Metabolite Identification

Common Name

Dehydropipernonaline

Description

Dehydropipernonaline 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. Dehydropipernonaline has been detected, but not quantified in, herbs and spices and pepper (spice). This could make dehydropipernonaline a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Dehydropipernonaline.

Structure

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

HMDB0040811
     RDKit          3D
Dehydropipernonaline
 50 52  0  0  0  0  0  0  0  0999 V2000
   -4.8754   -2.1607   -0.3294 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8149   -0.8968   -0.2512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5252   -0.2554   -0.0400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4523   -1.0049    0.0646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1326   -0.4212    0.2767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0390   -1.1348    0.3861 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2534   -0.4272    0.6014 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1749   -0.7724   -0.5609 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4792   -0.0767   -0.3718 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5655   -0.8092   -0.2771 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9110   -0.2684   -0.0905 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1522    1.0777    0.0029 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4576    1.5598    0.1819 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5370    0.7119    0.2700 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2977   -0.6433    0.1765 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0092   -1.1163   -0.0001 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5429   -1.2490    0.2961 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5874   -0.3121    0.1018 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9176    0.9000    0.4438 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0028   -0.1113   -0.3697 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8702    1.3167   -0.2726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1441    2.0511   -0.5405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2424    1.3580    0.2510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4677   -0.0141   -0.2794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2440   -0.7998   -0.5771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4646    0.8148    0.0276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5639   -2.0735   -0.0098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0348    0.6655    0.3504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1126   -2.2072    0.3165 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6856   -0.7820    1.5518 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1304    0.6549    0.5983 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3001   -1.8721   -0.5300 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6818   -0.5069   -1.5027 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5380    1.0053   -0.3129 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4336   -1.9018   -0.3453 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3487    1.7913   -0.0588 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6443    2.6307    0.2556 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8160   -2.1784   -0.0741 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8024   -0.3239   -1.0028 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.4672   -0.4958    0.7156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5243    1.5757    0.7628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0554    1.6960   -0.9426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0662    3.0803   -0.1360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3815    2.1048   -1.6199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1932    1.9151    0.2304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8369    1.2585    1.2937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0642    0.0872   -1.2308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1672   -0.5411    0.4251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2323   -1.6952    0.1108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2260   -1.2041   -1.6183 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
  2 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 16 11  1  0
 25 20  1  0
 19 14  1  0
  3 26  1  0
  4 27  1  0
  5 28  1  0
  6 29  1  0
  7 30  1  0
  7 31  1  0
  8 32  1  0
  8 33  1  0
  9 34  1  0
 10 35  1  0
 12 36  1  0
 13 37  1  0
 16 38  1  0
 18 39  1  0
 18 40  1  0
 21 41  1  0
 21 42  1  0
 22 43  1  0
 22 44  1  0
 23 45  1  0
 23 46  1  0
 24 47  1  0
 24 48  1  0
 25 49  1  0
 25 50  1  0
M  END


  Mrv0541 02241219022D          

 25 27  0  0  0  0            999 V2000
   -2.9358   -0.8249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6513   -1.2377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3668   -0.8249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1512   -1.0795    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6369   -0.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1512    0.2552    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3668    0.0007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6513    0.4135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9358    0.0007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2215    0.4135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5074    0.0007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7933    0.4135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0791    0.0007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6350    0.4135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3493    0.0007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0634    0.4135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7775    0.0007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4917    0.4135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2058    0.0007    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2058   -0.8249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9241   -1.2377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6369   -0.8249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6369    0.0007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9241    0.4135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4917    1.2377    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  9  2  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  7  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 25  2  0  0  0  0
 19 20  1  0  0  0  0
 19 24  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0040811

> <DATABASE_NAME>
hmdb

> <SMILES>
O=C(\C=C\C=C\CC\C=C\C1=CC=C2OCOC2=C1)N1CCCCC1

> <INCHI_IDENTIFIER>
InChI=1S/C21H25NO3/c23-21(22-14-8-5-9-15-22)11-7-4-2-1-3-6-10-18-12-13-19-20(16-18)25-17-24-19/h2,4,6-7,10-13,16H,1,3,5,8-9,14-15,17H2/b4-2+,10-6+,11-7+

> <INCHI_KEY>
KAYVDASZRFLFRZ-PQECNABGSA-N

> <FORMULA>
C21H25NO3

> <MOLECULAR_WEIGHT>
339.4281

> <EXACT_MASS>
339.183443671

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
40.06676556625195

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E,4E,8E)-9-(2H-1,3-benzodioxol-5-yl)-1-(piperidin-1-yl)nona-2,4,8-trien-1-one

> <ALOGPS_LOGP>
4.85

> <JCHEM_LOGP>
4.193664053666667

> <ALOGPS_LOGS>
-5.00

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
2.370272995323456

> <JCHEM_POLAR_SURFACE_AREA>
38.77

> <JCHEM_REFRACTIVITY>
102.42359999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.42e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E,4E,8E)-9-(2H-1,3-benzodioxol-5-yl)-1-(piperidin-1-yl)nona-2,4,8-trien-1-one

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0040811
     RDKit          3D
Dehydropipernonaline
 50 52  0  0  0  0  0  0  0  0999 V2000
   -4.8754   -2.1607   -0.3294 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8149   -0.8968   -0.2512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5252   -0.2554   -0.0400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4523   -1.0049    0.0646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1326   -0.4212    0.2767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0390   -1.1348    0.3861 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2534   -0.4272    0.6014 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1749   -0.7724   -0.5609 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4792   -0.0767   -0.3718 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5655   -0.8092   -0.2771 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9110   -0.2684   -0.0905 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1522    1.0777    0.0029 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4576    1.5598    0.1819 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5370    0.7119    0.2700 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2977   -0.6433    0.1765 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0092   -1.1163   -0.0001 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5429   -1.2490    0.2961 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5874   -0.3121    0.1018 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9176    0.9000    0.4438 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0028   -0.1113   -0.3697 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8702    1.3167   -0.2726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1441    2.0511   -0.5405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2424    1.3580    0.2510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4677   -0.0141   -0.2794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2440   -0.7998   -0.5771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4646    0.8148    0.0276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5639   -2.0735   -0.0098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0348    0.6655    0.3504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1126   -2.2072    0.3165 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6856   -0.7820    1.5518 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1304    0.6549    0.5983 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3001   -1.8721   -0.5300 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6818   -0.5069   -1.5027 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5380    1.0053   -0.3129 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4336   -1.9018   -0.3453 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3487    1.7913   -0.0588 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6443    2.6307    0.2556 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8160   -2.1784   -0.0741 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8024   -0.3239   -1.0028 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.4672   -0.4958    0.7156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5243    1.5757    0.7628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0554    1.6960   -0.9426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0662    3.0803   -0.1360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3815    2.1048   -1.6199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1932    1.9151    0.2304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8369    1.2585    1.2937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0642    0.0872   -1.2308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1672   -0.5411    0.4251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2323   -1.6952    0.1108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2260   -1.2041   -1.6183 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
  2 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 16 11  1  0
 25 20  1  0
 19 14  1  0
  3 26  1  0
  4 27  1  0
  5 28  1  0
  6 29  1  0
  7 30  1  0
  7 31  1  0
  8 32  1  0
  8 33  1  0
  9 34  1  0
 10 35  1  0
 12 36  1  0
 13 37  1  0
 16 38  1  0
 18 39  1  0
 18 40  1  0
 21 41  1  0
 21 42  1  0
 22 43  1  0
 22 44  1  0
 23 45  1  0
 23 46  1  0
 24 47  1  0
 24 48  1  0
 25 49  1  0
 25 50  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      -5.480  -1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.816  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -8.151  -1.540   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -9.616  -2.015   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0     -10.522  -0.769   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -9.616   0.476   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -8.151   0.001   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -6.816   0.772   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.480   0.001   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.147   0.772   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.814   0.001   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.481   0.772   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.148   0.001   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.185   0.772   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.519   0.001   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.852   0.772   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.185   0.001   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.518   0.772   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       7.851   0.001   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0       7.851  -1.540   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.192  -2.310   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.522  -1.540   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.522   0.001   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.192   0.772   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       6.518   2.310   0.000  0.00  0.00           O+0
CONECT    1    2    9                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    7                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    3    6    8                                                  
CONECT    8    7    9                                                       
CONECT    9    1    8   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   25                                                  
CONECT   19   18   20   24                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   19   23                                                       
CONECT   25   18                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

COMPND    HMDB0040811
HETATM    1  O1  UNL     1      -4.875  -2.161  -0.329  1.00  0.00           O  
HETATM    2  C1  UNL     1      -4.815  -0.897  -0.251  1.00  0.00           C  
HETATM    3  C2  UNL     1      -3.525  -0.255  -0.040  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.452  -1.005   0.065  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.133  -0.421   0.277  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.039  -1.135   0.386  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.253  -0.427   0.601  1.00  0.00           C  
HETATM    8  C7  UNL     1       2.175  -0.772  -0.561  1.00  0.00           C  
HETATM    9  C8  UNL     1       3.479  -0.077  -0.372  1.00  0.00           C  
HETATM   10  C9  UNL     1       4.566  -0.809  -0.277  1.00  0.00           C  
HETATM   11  C10 UNL     1       5.911  -0.268  -0.091  1.00  0.00           C  
HETATM   12  C11 UNL     1       6.152   1.078   0.003  1.00  0.00           C  
HETATM   13  C12 UNL     1       7.458   1.560   0.182  1.00  0.00           C  
HETATM   14  C13 UNL     1       8.537   0.712   0.270  1.00  0.00           C  
HETATM   15  C14 UNL     1       8.298  -0.643   0.176  1.00  0.00           C  
HETATM   16  C15 UNL     1       7.009  -1.116  -0.000  1.00  0.00           C  
HETATM   17  O2  UNL     1       9.543  -1.249   0.296  1.00  0.00           O  
HETATM   18  C16 UNL     1      10.587  -0.312   0.102  1.00  0.00           C  
HETATM   19  O3  UNL     1       9.918   0.900   0.444  1.00  0.00           O  
HETATM   20  N1  UNL     1      -6.003  -0.111  -0.370  1.00  0.00           N  
HETATM   21  C17 UNL     1      -5.870   1.317  -0.273  1.00  0.00           C  
HETATM   22  C18 UNL     1      -7.144   2.051  -0.541  1.00  0.00           C  
HETATM   23  C19 UNL     1      -8.242   1.358   0.251  1.00  0.00           C  
HETATM   24  C20 UNL     1      -8.468  -0.014  -0.279  1.00  0.00           C  
HETATM   25  C21 UNL     1      -7.244  -0.800  -0.577  1.00  0.00           C  
HETATM   26  H1  UNL     1      -3.465   0.815   0.028  1.00  0.00           H  
HETATM   27  H2  UNL     1      -2.564  -2.074  -0.010  1.00  0.00           H  
HETATM   28  H3  UNL     1      -1.035   0.666   0.350  1.00  0.00           H  
HETATM   29  H4  UNL     1      -0.113  -2.207   0.316  1.00  0.00           H  
HETATM   30  H5  UNL     1       1.686  -0.782   1.552  1.00  0.00           H  
HETATM   31  H6  UNL     1       1.130   0.655   0.598  1.00  0.00           H  
HETATM   32  H7  UNL     1       2.300  -1.872  -0.530  1.00  0.00           H  
HETATM   33  H8  UNL     1       1.682  -0.507  -1.503  1.00  0.00           H  
HETATM   34  H9  UNL     1       3.538   1.005  -0.313  1.00  0.00           H  
HETATM   35  H10 UNL     1       4.434  -1.902  -0.345  1.00  0.00           H  
HETATM   36  H11 UNL     1       5.349   1.791  -0.059  1.00  0.00           H  
HETATM   37  H12 UNL     1       7.644   2.631   0.256  1.00  0.00           H  
HETATM   38  H13 UNL     1       6.816  -2.178  -0.074  1.00  0.00           H  
HETATM   39  H14 UNL     1      10.802  -0.324  -1.003  1.00  0.00           H  
HETATM   40  H15 UNL     1      11.467  -0.496   0.716  1.00  0.00           H  
HETATM   41  H16 UNL     1      -5.524   1.576   0.763  1.00  0.00           H  
HETATM   42  H17 UNL     1      -5.055   1.696  -0.943  1.00  0.00           H  
HETATM   43  H18 UNL     1      -7.066   3.080  -0.136  1.00  0.00           H  
HETATM   44  H19 UNL     1      -7.382   2.105  -1.620  1.00  0.00           H  
HETATM   45  H20 UNL     1      -9.193   1.915   0.230  1.00  0.00           H  
HETATM   46  H21 UNL     1      -7.837   1.258   1.294  1.00  0.00           H  
HETATM   47  H22 UNL     1      -9.064   0.087  -1.231  1.00  0.00           H  
HETATM   48  H23 UNL     1      -9.167  -0.541   0.425  1.00  0.00           H  
HETATM   49  H24 UNL     1      -7.232  -1.695   0.111  1.00  0.00           H  
HETATM   50  H25 UNL     1      -7.226  -1.204  -1.618  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   20
CONECT    3    4    4   26
CONECT    4    5   27
CONECT    5    6    6   28
CONECT    6    7   29
CONECT    7    8   30   31
CONECT    8    9   32   33
CONECT    9   10   10   34
CONECT   10   11   35
CONECT   11   12   12   16
CONECT   12   13   36
CONECT   13   14   14   37
CONECT   14   15   19
CONECT   15   16   16   17
CONECT   16   38
CONECT   17   18
CONECT   18   19   39   40
CONECT   20   21   25
CONECT   21   22   41   42
CONECT   22   23   43   44
CONECT   23   24   45   46
CONECT   24   25   47   48
CONECT   25   49   50
END

HMDB0040811
     RDKit          3D
Dehydropipernonaline
 50 52  0  0  0  0  0  0  0  0999 V2000
   -4.8754   -2.1607   -0.3294 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8149   -0.8968   -0.2512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5252   -0.2554   -0.0400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4523   -1.0049    0.0646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1326   -0.4212    0.2767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0390   -1.1348    0.3861 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2534   -0.4272    0.6014 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1749   -0.7724   -0.5609 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4792   -0.0767   -0.3718 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5655   -0.8092   -0.2771 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9110   -0.2684   -0.0905 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1522    1.0777    0.0029 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4576    1.5598    0.1819 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5370    0.7119    0.2700 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2977   -0.6433    0.1765 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0092   -1.1163   -0.0001 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5429   -1.2490    0.2961 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5874   -0.3121    0.1018 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9176    0.9000    0.4438 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0028   -0.1113   -0.3697 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8702    1.3167   -0.2726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1441    2.0511   -0.5405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2424    1.3580    0.2510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4677   -0.0141   -0.2794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2440   -0.7998   -0.5771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4646    0.8148    0.0276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5639   -2.0735   -0.0098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0348    0.6655    0.3504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1126   -2.2072    0.3165 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6856   -0.7820    1.5518 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1304    0.6549    0.5983 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3001   -1.8721   -0.5300 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6818   -0.5069   -1.5027 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5380    1.0053   -0.3129 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4336   -1.9018   -0.3453 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3487    1.7913   -0.0588 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6443    2.6307    0.2556 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8160   -2.1784   -0.0741 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8024   -0.3239   -1.0028 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.4672   -0.4958    0.7156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5243    1.5757    0.7628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0554    1.6960   -0.9426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0662    3.0803   -0.1360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3815    2.1048   -1.6199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1932    1.9151    0.2304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8369    1.2585    1.2937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0642    0.0872   -1.2308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1672   -0.5411    0.4251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2323   -1.6952    0.1108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2260   -1.2041   -1.6183 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
  2 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 16 11  1  0
 25 20  1  0
 19 14  1  0
  3 26  1  0
  4 27  1  0
  5 28  1  0
  6 29  1  0
  7 30  1  0
  7 31  1  0
  8 32  1  0
  8 33  1  0
  9 34  1  0
 10 35  1  0
 12 36  1  0
 13 37  1  0
 16 38  1  0
 18 39  1  0
 18 40  1  0
 21 41  1  0
 21 42  1  0
 22 43  1  0
 22 44  1  0
 23 45  1  0
 23 46  1  0
 24 47  1  0
 24 48  1  0
 25 49  1  0
 25 50  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
9-(3,4-Methylenedioxy)-2,4,8-nonatrienoic acid piperidide	HMDB
N-(9-(3,4-Methylenedioxyphenyl)-2,4,8-nonatrienoyl)piperidine	MeSH
Dehydropipernonaline	MeSH

Chemical Formula

C₂₁H₂₅NO₃

Average Molecular Weight

339.4281

Monoisotopic Molecular Weight

339.183443671

IUPAC Name

(2E,4E,8E)-9-(2H-1,3-benzodioxol-5-yl)-1-(piperidin-1-yl)nona-2,4,8-trien-1-one

Traditional Name

(2E,4E,8E)-9-(2H-1,3-benzodioxol-5-yl)-1-(piperidin-1-yl)nona-2,4,8-trien-1-one

CAS Registry Number

107584-38-3

SMILES

O=C(\C=C\C=C\CC\C=C\C1=CC=C2OCOC2=C1)N1CCCCC1

InChI Identifier

InChI=1S/C21H25NO3/c23-21(22-14-8-5-9-15-22)11-7-4-2-1-3-6-10-18-12-13-19-20(16-18)25-17-24-19/h2,4,6-7,10-13,16H,1,3,5,8-9,14-15,17H2/b4-2+,10-6+,11-7+

InChI Key

KAYVDASZRFLFRZ-PQECNABGSA-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-piperidine
Styrene
Piperidine
Benzenoid
Tertiary carboxylic acid amide
Carboxamide group
Acetal
Carboxylic acid derivative
Oxacycle
Azacycle
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organic nitrogen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0040811)

Cellular substructure

Membrane (HMDB: HMDB0040811)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0040811)

Source

Exogenous

Food

Food (HMDB: HMDB0040811)

Herb and spice

Spice

Pepper (Spice) (FooDB: FOOD00139)

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Plant

Plant (HMDB: HMDB0040811)

Not Available

Nutrient (HMDB: HMDB0040811)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	98 - 99 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.16 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	0.0034 g/L	ALOGPS
logP	4.85	ALOGPS
logP	4.19	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Basic)	2.37	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	38.77 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	102.42 m³·mol⁻¹	ChemAxon
Polarizability	40.07 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	185.058	31661259
DarkChem	[M-H]-	183.959	31661259
DeepCCS	[M+H]+	180.465	30932474
DeepCCS	[M-H]-	178.107	30932474
DeepCCS	[M-2H]-	212.163	30932474
DeepCCS	[M+Na]+	187.39	30932474
AllCCS	[M+H]+	186.3	32859911
AllCCS	[M+H-H2O]+	183.2	32859911
AllCCS	[M+NH4]+	189.3	32859911
AllCCS	[M+Na]+	190.1	32859911
AllCCS	[M-H]-	188.0	32859911
AllCCS	[M+Na-2H]-	188.4	32859911
AllCCS	[M+HCOO]-	189.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dehydropipernonaline	O=C(\C=C\C=C\CC\C=C\C1=CC=C2OCOC2=C1)N1CCCCC1	4449.1	Standard polar	33892256
Dehydropipernonaline	O=C(\C=C\C=C\CC\C=C\C1=CC=C2OCOC2=C1)N1CCCCC1	2900.6	Standard non polar	33892256
Dehydropipernonaline	O=C(\C=C\C=C\CC\C=C\C1=CC=C2OCOC2=C1)N1CCCCC1	3377.9	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 - Dehydropipernonaline GC-MS (Non-derivatized) - 70eV, Positive	splash10-0cg3-5923000000-9d62c3b8145efebb29f1	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dehydropipernonaline 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 - Dehydropipernonaline 10V, Positive-QTOF	splash10-0006-3119000000-3d94e6a9227dc34d2d8d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydropipernonaline 20V, Positive-QTOF	splash10-000i-7983000000-7892aacbdaa95eee41f1	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydropipernonaline 40V, Positive-QTOF	splash10-000i-9210000000-1cd3fdbcc6da59c29247	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydropipernonaline 10V, Negative-QTOF	splash10-000i-0009000000-c0283db600dce772b31e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydropipernonaline 20V, Negative-QTOF	splash10-001r-8239000000-ee0b629c5237c33a4317	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydropipernonaline 40V, Negative-QTOF	splash10-001i-9010000000-1f41920040766ce6c492	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydropipernonaline 10V, Negative-QTOF	splash10-000i-0009000000-0ab7a62a80795c1812b7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydropipernonaline 20V, Negative-QTOF	splash10-000i-0319000000-c92b8db95a323f445419	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydropipernonaline 40V, Negative-QTOF	splash10-000l-5926000000-aeea3887564cc0d11aee	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydropipernonaline 10V, Positive-QTOF	splash10-0006-0029000000-16b29f21f2918f96db13	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydropipernonaline 20V, Positive-QTOF	splash10-0006-2196000000-90e371ea7421e81afd08	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydropipernonaline 40V, Positive-QTOF	splash10-001j-7950000000-91ecdf36e2612d654675	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

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

FDB020627

KNApSAcK ID

C00034476

Chemspider ID

4944315

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6439947

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1886591

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 Dehydropipernonaline (HMDB0040811)

MOL for HMDB0040811 (Dehydropipernonaline)

3D MOL for HMDB0040811 (Dehydropipernonaline)

3D SDF for HMDB0040811 (Dehydropipernonaline)

3D-SDF for HMDB0040811 (Dehydropipernonaline)

PDB for HMDB0040811 (Dehydropipernonaline)

3D PDB for HMDB0040811 (Dehydropipernonaline)

SMILES for HMDB0040811 (Dehydropipernonaline)

INCHI for HMDB0040811 (Dehydropipernonaline)

Structure for HMDB0040811 (Dehydropipernonaline)

3D Structure for HMDB0040811 (Dehydropipernonaline)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra