Showing metabocard for Piperonal (MMDBc0033706)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-19 04:59:45 UTC
Update Date2022-08-31 22:37:54 UTC
Metabolite IDMMDBc0033706
Metabolite Identification
Common NamePiperonal
Description3,4-Methylenedioxybenzaldehyde, also known as heliotropin or piperonyl aldehyde, 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. 3,4-Methylenedioxybenzaldehyde is a sweet, bitter, and coconut tasting compound. 3,4-Methylenedioxybenzaldehyde has been detected, but not quantified in, several different foods, such as highbush blueberries (Vaccinium corymbosum), pepper (spice), rabbiteye blueberries (Vaccinium virgatum), and vanillas (Vanilla). This could make 3,4-methylenedioxybenzaldehyde a potential biomarker for the consumption of these foods. 3,4-Methylenedioxybenzaldehyde is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on 3,4-Methylenedioxybenzaldehyde.
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007f12411dfe70>

Piperonal
  Mrv1652303202019012D          

 12 13  0  0  0  0            999 V2000
    2.6868   -0.6936    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6868    0.6340    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3254   -0.4423    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4674   -0.4423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4674    0.3827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1819   -0.8548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2053   -0.0297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1819    0.7952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8964   -0.4423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8964    0.3827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6109   -0.8548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6109   -1.3663    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  0  0  0  0
  1  7  1  0  0  0  0
  2  5  1  0  0  0  0
  2  7  1  0  0  0  0
  3 11  2  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  5  8  1  0  0  0  0
  6  9  2  0  0  0  0
  8 10  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x00007f12411dfe70>

HMDB0032612
     RDKit          3D
3,4-Methylenedioxybenzaldehyde
 17 18  0  0  0  0  0  0  0  0999 V2000
   -3.3822   -1.3966   -0.7214 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0298   -0.3354   -0.1499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6149   -0.0000   -0.0563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1973    1.1584    0.5655 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1535    1.4738    0.6521 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1045    0.6481    0.1256 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7150   -0.5017   -0.4932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6344   -0.8148   -0.5786 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8871   -1.1416   -0.9303 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9474   -0.6495   -0.0956 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5097    0.7080    0.0654 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8121    0.2877    0.2517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9656    1.8020    0.9777 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4664    2.3978    1.1494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9401   -1.7221   -1.0670 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8693   -1.1916    0.8767 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9234   -0.7223   -0.5718 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
  8  3  1  0
 11  6  1  0
  2 12  1  0
  4 13  1  0
  5 14  1  0
  8 15  1  0
 10 16  1  0
 10 17  1  0
M  END
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3D SDF for #<Metabolite:0x00007f12411dfe70>

Piperonal
  Mrv1652303202019012D          

 12 13  0  0  0  0            999 V2000
    2.6868   -0.6936    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6868    0.6340    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3254   -0.4423    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4674   -0.4423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4674    0.3827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1819   -0.8548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2053   -0.0297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1819    0.7952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8964   -0.4423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8964    0.3827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6109   -0.8548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6109   -1.3663    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  0  0  0  0
  1  7  1  0  0  0  0
  2  5  1  0  0  0  0
  2  7  1  0  0  0  0
  3 11  2  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  5  8  1  0  0  0  0
  6  9  2  0  0  0  0
  8 10  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0033706

> <DATABASE_NAME>
MIME

> <SMILES>
[H]C(=O)C1=CC2=C(OCO2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C8H6O3/c9-4-6-1-2-7-8(3-6)11-5-10-7/h1-4H,5H2

> <INCHI_KEY>
SATCULPHIDQDRE-UHFFFAOYSA-N

> <FORMULA>
C8H6O3

> <MOLECULAR_WEIGHT>
150.1314

> <EXACT_MASS>
150.031694058

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
14.248836806071637

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2H-1,3-benzodioxole-5-carbaldehyde

> <ALOGPS_LOGP>
0.79

> <JCHEM_LOGP>
1.3089816283333333

> <ALOGPS_LOGS>
-1.26

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.748857576577568

> <JCHEM_POLAR_SURFACE_AREA>
35.53

> <JCHEM_REFRACTIVITY>
38.4089

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.28e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
piperonal

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for #<Metabolite:0x00007f12411dfe70>

HMDB0032612
     RDKit          3D
3,4-Methylenedioxybenzaldehyde
 17 18  0  0  0  0  0  0  0  0999 V2000
   -3.3822   -1.3966   -0.7214 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0298   -0.3354   -0.1499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6149   -0.0000   -0.0563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1973    1.1584    0.5655 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1535    1.4738    0.6521 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1045    0.6481    0.1256 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7150   -0.5017   -0.4932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6344   -0.8148   -0.5786 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8871   -1.1416   -0.9303 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9474   -0.6495   -0.0956 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5097    0.7080    0.0654 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8121    0.2877    0.2517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9656    1.8020    0.9777 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4664    2.3978    1.1494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9401   -1.7221   -1.0670 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8693   -1.1916    0.8767 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9234   -0.7223   -0.5718 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
  8  3  1  0
 11  6  1  0
  2 12  1  0
  4 13  1  0
  5 14  1  0
  8 15  1  0
 10 16  1  0
 10 17  1  0
M  END
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PDB for #<Metabolite:0x00007f12411dfe70>

HEADER    PROTEIN                                 20-MAR-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Piperonal                                         
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAR-20         0                                  
HETATM    1  O   UNK     0       5.015  -1.295   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       5.015   1.183   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      11.807  -0.826   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       6.472  -0.826   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.472   0.714   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.806  -1.596   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.117  -0.055   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.806   1.484   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.140  -0.826   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.140   0.714   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.474  -1.596   0.000  0.00  0.00           C+0
HETATM   12  H   UNK     0      10.474  -2.550   0.000  0.00  0.00           H+0
CONECT    1    4    7                                                       
CONECT    2    5    7                                                       
CONECT    3   11                                                            
CONECT    4    1    5    6                                                  
CONECT    5    2    4    8                                                  
CONECT    6    4    9                                                       
CONECT    7    1    2                                                       
CONECT    8    5   10                                                       
CONECT    9    6   10   11                                                  
CONECT   10    8    9                                                       
CONECT   11    3    9   12                                                  
CONECT   12   11                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END
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3D PDB for #<Metabolite:0x00007f12411dfe70>

COMPND    HMDB0032612
HETATM    1  O1  UNL     1      -3.382  -1.397  -0.721  1.00  0.00           O  
HETATM    2  C1  UNL     1      -3.030  -0.335  -0.150  1.00  0.00           C  
HETATM    3  C2  UNL     1      -1.615  -0.000  -0.056  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.197   1.158   0.565  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.153   1.474   0.652  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.104   0.648   0.126  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.715  -0.502  -0.493  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.634  -0.815  -0.579  1.00  0.00           C  
HETATM    9  O2  UNL     1       1.887  -1.142  -0.930  1.00  0.00           O  
HETATM   10  C8  UNL     1       2.947  -0.649  -0.096  1.00  0.00           C  
HETATM   11  O3  UNL     1       2.510   0.708   0.065  1.00  0.00           O  
HETATM   12  H1  UNL     1      -3.812   0.288   0.252  1.00  0.00           H  
HETATM   13  H2  UNL     1      -1.966   1.802   0.978  1.00  0.00           H  
HETATM   14  H3  UNL     1       0.466   2.398   1.149  1.00  0.00           H  
HETATM   15  H4  UNL     1      -0.940  -1.722  -1.067  1.00  0.00           H  
HETATM   16  H5  UNL     1       2.869  -1.192   0.877  1.00  0.00           H  
HETATM   17  H6  UNL     1       3.923  -0.722  -0.572  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   12
CONECT    3    4    4    8
CONECT    4    5   13
CONECT    5    6    6   14
CONECT    6    7   11
CONECT    7    8    8    9
CONECT    8   15
CONECT    9   10
CONECT   10   11   16   17
END
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SMILES for #<Metabolite:0x00007f12411dfe70>

[H]C(=O)C1=CC2=C(OCO2)C=C1
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INCHI for #<Metabolite:0x00007f12411dfe70>

InChI=1S/C8H6O3/c9-4-6-1-2-7-8(3-6)11-5-10-7/h1-4H,5H2
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Synonyms
ValueSource
1,3-Benzodioxole-5-carboxaldehydeChEBI
3,4-(Methylenedioxy)benzaldehydeChEBI
3,4-Dihydroxybenzaldehyde methylene ketalChEBI
5-Formyl-1,3-benzodioxoleChEBI
HeliotropinChEBI
HeliotropineChEBI
PiperonaldehydeChEBI
Piperonyl aldehydeChEBI
PiperonylaldehydeChEBI
Protocatechuic aldehyde methylene etherChEBI
1,3-Benzodioxole-5-carbaldehydeHMDB
1,3-Benzodioxole-5-carboxaldehyde, 9ciHMDB
3, 4-(Methylenedioxy)benzaldehydeHMDB
3, 4-Bis(methylenedioxy)benzaldehydeHMDB
3,4-(Methylenedioxy)-benzaldehydeHMDB
3,4-Bis(methylenedioxy)benzaldehydeHMDB
3,4-DimethylenedioxybenzaldehydeHMDB
3,4-METHYLEN-dioxy-benzaldehydeHMDB
3,4-Methylene-dihydroxybenzaldehydeHMDB
Blue PHMDB
Dioxymethylene protocatechuic aldehydeHMDB
Dioxymethylene-protocatechuic aldehydeHMDB
FEMA 2911HMDB
GeliotropinHMDB
Heliotropine (piperonal)HMDB
PiperanalHMDB
PiperonalHMDB
Piperonal, 8ciHMDB
3,4-MethylenedioxybenzaldehydeChEBI
HeliotrinMeSH
Molecular FormulaC8H6O3
Average Mass150.1314
Monoisotopic Mass150.031694058
IUPAC Name2H-1,3-benzodioxole-5-carbaldehyde
Traditional Namepiperonal
CAS Registry Number120-57-0
SMILES
[H]C(=O)C1=CC2=C(OCO2)C=C1
InChI Identifier
InChI=1S/C8H6O3/c9-4-6-1-2-7-8(3-6)11-5-10-7/h1-4H,5H2
InChI KeySATCULPHIDQDRE-UHFFFAOYSA-N