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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:38:39 UTC

Update Date

2022-03-07 02:52:40 UTC

HMDB ID

HMDB0030725

Secondary Accession Numbers

HMDB30725

Metabolite Identification

Common Name

Dillapiol

Description

Dillapiol 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. Dillapiol is a spice and wood tasting compound. Dillapiol is found, on average, in the highest concentration within dills (Anethum graveolens) and cumins (Cuminum cyminum). Dillapiol has also been detected, but not quantified in, several different foods, such as corianders (Coriandrum sativum), fennels (Foeniculum vulgare), herbs and spices, and parsleys (Petroselinum crispum). This could make dillapiol a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Dillapiol.

Structure

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

HMDB0030725
     RDKit          3D
Dillapiol
 30 31  0  0  0  0  0  0  0  0999 V2000
    4.2920    0.1197    0.0735 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1376   -0.5378   -0.0543 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1370   -0.5209    1.0205 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8211    0.0375    0.6379 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6040    1.3802    0.9940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5835    1.9998    0.6754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5479    1.2779    0.0037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3711   -0.0376   -0.3610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3220   -0.7837   -1.0354 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3137   -1.5555   -0.4128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1616   -0.6482   -0.0294 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0232   -1.9583   -0.3873 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5419   -2.2877   -1.6511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6318    2.1186   -0.1946 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4929    3.2275    0.6541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0991    3.2801    0.8776 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0359    0.1216   -0.6965 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5283    0.6915    0.9861 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9669   -1.0760   -0.9613 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0040   -1.5766    1.3844 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5439    0.0508    1.8878 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3692    1.9254    1.5170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1634   -1.7593   -1.1065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8584   -2.5345   -0.0904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7445   -1.0732    0.4709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2162   -2.7505   -2.3205 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8877   -1.3715   -2.1814 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4533   -2.9476   -1.5665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9601    3.0241    1.6584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8799    4.1645    0.2078 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  8 11  2  0
 11 12  1  0
 12 13  1  0
  7 14  1  0
 14 15  1  0
 15 16  1  0
 11  4  1  0
 16  6  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  3 20  1  0
  3 21  1  0
  5 22  1  0
 10 23  1  0
 10 24  1  0
 10 25  1  0
 13 26  1  0
 13 27  1  0
 13 28  1  0
 15 29  1  0
 15 30  1  0
M  END

Dillapiole
  Mrv1652309251700152D          

 16 17  0  0  0  0            999 V2000
    1.7383   -0.6126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7383    0.7151    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6625   -0.7737    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2334   -1.5987    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9480    0.4637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5190   -0.3611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5190    0.4637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9480   -0.3611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2334   -0.7737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2334    0.8763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6625    0.8763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2568    0.0513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6625    1.7013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3771   -0.3611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9480   -2.0112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3771    2.1138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  1 12  1  0  0  0  0
  2  7  1  0  0  0  0
  2 12  1  0  0  0  0
  3  8  1  0  0  0  0
  3 14  1  0  0  0  0
  4  9  1  0  0  0  0
  4 15  1  0  0  0  0
  5  8  1  0  0  0  0
  5 10  2  0  0  0  0
  5 11  1  0  0  0  0
  6  7  2  0  0  0  0
  6  9  1  0  0  0  0
  7 10  1  0  0  0  0
  8  9  2  0  0  0  0
 11 13  1  0  0  0  0
 13 16  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030725

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(OC)C(CC=C)=CC2=C1OCO2

> <INCHI_IDENTIFIER>
InChI=1S/C12H14O4/c1-4-5-8-6-9-11(16-7-15-9)12(14-3)10(8)13-2/h4,6H,1,5,7H2,2-3H3

> <INCHI_KEY>
LIKYNOPXHGPMIH-UHFFFAOYSA-N

> <FORMULA>
C12H14O4

> <MOLECULAR_WEIGHT>
222.2372

> <EXACT_MASS>
222.089208936

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
22.944835214004673

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4,5-dimethoxy-6-(prop-2-en-1-yl)-2H-1,3-benzodioxole

> <ALOGPS_LOGP>
2.33

> <JCHEM_LOGP>
2.3797074853333333

> <ALOGPS_LOGS>
-2.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.401145947371453

> <JCHEM_POLAR_SURFACE_AREA>
36.92

> <JCHEM_REFRACTIVITY>
59.03860000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.46e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
dillapiol

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0030725
     RDKit          3D
Dillapiol
 30 31  0  0  0  0  0  0  0  0999 V2000
    4.2920    0.1197    0.0735 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1376   -0.5378   -0.0543 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1370   -0.5209    1.0205 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8211    0.0375    0.6379 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6040    1.3802    0.9940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5835    1.9998    0.6754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5479    1.2779    0.0037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3711   -0.0376   -0.3610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3220   -0.7837   -1.0354 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3137   -1.5555   -0.4128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1616   -0.6482   -0.0294 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0232   -1.9583   -0.3873 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5419   -2.2877   -1.6511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6318    2.1186   -0.1946 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4929    3.2275    0.6541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0991    3.2801    0.8776 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0359    0.1216   -0.6965 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5283    0.6915    0.9861 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9669   -1.0760   -0.9613 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0040   -1.5766    1.3844 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5439    0.0508    1.8878 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3692    1.9254    1.5170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1634   -1.7593   -1.1065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8584   -2.5345   -0.0904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7445   -1.0732    0.4709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2162   -2.7505   -2.3205 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8877   -1.3715   -2.1814 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4533   -2.9476   -1.5665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9601    3.0241    1.6584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8799    4.1645    0.2078 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  8 11  2  0
 11 12  1  0
 12 13  1  0
  7 14  1  0
 14 15  1  0
 15 16  1  0
 11  4  1  0
 16  6  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  3 20  1  0
  3 21  1  0
  5 22  1  0
 10 23  1  0
 10 24  1  0
 10 25  1  0
 13 26  1  0
 13 27  1  0
 13 28  1  0
 15 29  1  0
 15 30  1  0
M  END

HEADER    PROTEIN                                 25-SEP-17   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Dillapiole                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-SEP-17         0                                  
HETATM    1  O   UNK     0       3.245  -1.143   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       3.245   1.335   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       8.703  -1.444   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       6.036  -2.984   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       7.370   0.866   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.702  -0.674   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.702   0.866   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.370  -0.674   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.036  -1.444   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.036   1.636   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.703   1.636   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.346   0.096   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.703   3.176   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.037  -0.674   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.370  -3.754   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.037   3.946   0.000  0.00  0.00           C+0
CONECT    1    6   12                                                       
CONECT    2    7   12                                                       
CONECT    3    8   14                                                       
CONECT    4    9   15                                                       
CONECT    5    8   10   11                                                  
CONECT    6    1    7    9                                                  
CONECT    7    2    6   10                                                  
CONECT    8    3    5    9                                                  
CONECT    9    4    6    8                                                  
CONECT   10    5    7                                                       
CONECT   11    5   13                                                       
CONECT   12    1    2                                                       
CONECT   13   11   16                                                       
CONECT   14    3                                                            
CONECT   15    4                                                            
CONECT   16   13                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

COMPND    HMDB0030725
HETATM    1  C1  UNL     1       4.292   0.120   0.074  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.138  -0.538  -0.054  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.137  -0.521   1.021  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.821   0.038   0.638  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.604   1.380   0.994  1.00  0.00           C  
HETATM    6  C6  UNL     1      -0.583   2.000   0.675  1.00  0.00           C  
HETATM    7  C7  UNL     1      -1.548   1.278   0.004  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.371  -0.038  -0.361  1.00  0.00           C  
HETATM    9  O1  UNL     1      -2.322  -0.784  -1.035  1.00  0.00           O  
HETATM   10  C9  UNL     1      -3.314  -1.556  -0.413  1.00  0.00           C  
HETATM   11  C10 UNL     1      -0.162  -0.648  -0.029  1.00  0.00           C  
HETATM   12  O2  UNL     1       0.023  -1.958  -0.387  1.00  0.00           O  
HETATM   13  C11 UNL     1       0.542  -2.288  -1.651  1.00  0.00           C  
HETATM   14  O3  UNL     1      -2.632   2.119  -0.195  1.00  0.00           O  
HETATM   15  C12 UNL     1      -2.493   3.227   0.654  1.00  0.00           C  
HETATM   16  O4  UNL     1      -1.099   3.280   0.878  1.00  0.00           O  
HETATM   17  H1  UNL     1       5.036   0.122  -0.696  1.00  0.00           H  
HETATM   18  H2  UNL     1       4.528   0.691   0.986  1.00  0.00           H  
HETATM   19  H3  UNL     1       2.967  -1.076  -0.961  1.00  0.00           H  
HETATM   20  H4  UNL     1       2.004  -1.577   1.384  1.00  0.00           H  
HETATM   21  H5  UNL     1       2.544   0.051   1.888  1.00  0.00           H  
HETATM   22  H6  UNL     1       1.369   1.925   1.517  1.00  0.00           H  
HETATM   23  H7  UNL     1      -4.163  -1.759  -1.106  1.00  0.00           H  
HETATM   24  H8  UNL     1      -2.858  -2.534  -0.090  1.00  0.00           H  
HETATM   25  H9  UNL     1      -3.744  -1.073   0.471  1.00  0.00           H  
HETATM   26  H10 UNL     1      -0.216  -2.751  -2.320  1.00  0.00           H  
HETATM   27  H11 UNL     1       0.888  -1.371  -2.181  1.00  0.00           H  
HETATM   28  H12 UNL     1       1.453  -2.948  -1.566  1.00  0.00           H  
HETATM   29  H13 UNL     1      -2.960   3.024   1.658  1.00  0.00           H  
HETATM   30  H14 UNL     1      -2.880   4.164   0.208  1.00  0.00           H  
CONECT    1    2    2   17   18
CONECT    2    3   19
CONECT    3    4   20   21
CONECT    4    5    5   11
CONECT    5    6   22
CONECT    6    7    7   16
CONECT    7    8   14
CONECT    8    9   11   11
CONECT    9   10
CONECT   10   23   24   25
CONECT   11   12
CONECT   12   13
CONECT   13   26   27   28
CONECT   14   15
CONECT   15   16   29   30
END

HMDB0030725
     RDKit          3D
Dillapiol
 30 31  0  0  0  0  0  0  0  0999 V2000
    4.2920    0.1197    0.0735 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1376   -0.5378   -0.0543 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1370   -0.5209    1.0205 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8211    0.0375    0.6379 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6040    1.3802    0.9940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5835    1.9998    0.6754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5479    1.2779    0.0037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3711   -0.0376   -0.3610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3220   -0.7837   -1.0354 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3137   -1.5555   -0.4128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1616   -0.6482   -0.0294 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0232   -1.9583   -0.3873 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5419   -2.2877   -1.6511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6318    2.1186   -0.1946 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4929    3.2275    0.6541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0991    3.2801    0.8776 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0359    0.1216   -0.6965 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5283    0.6915    0.9861 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9669   -1.0760   -0.9613 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0040   -1.5766    1.3844 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5439    0.0508    1.8878 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3692    1.9254    1.5170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1634   -1.7593   -1.1065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8584   -2.5345   -0.0904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7445   -1.0732    0.4709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2162   -2.7505   -2.3205 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8877   -1.3715   -2.1814 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4533   -2.9476   -1.5665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9601    3.0241    1.6584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8799    4.1645    0.2078 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  8 11  2  0
 11 12  1  0
 12 13  1  0
  7 14  1  0
 14 15  1  0
 15 16  1  0
 11  4  1  0
 16  6  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  3 20  1  0
  3 21  1  0
  5 22  1  0
 10 23  1  0
 10 24  1  0
 10 25  1  0
 13 26  1  0
 13 27  1  0
 13 28  1  0
 15 29  1  0
 15 30  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
5-Allyl 6,7-dimethoxy 1,3-benzodioxole	MeSH
1-Allyl-2,3-dimethoxy-4,5-(methylenedioxy)benzene	MeSH
2-Methyl-5-(1-methylethenyl)-1,3-benzodioxole	MeSH
1,3-Benzodioxole, 4,5-dimethoxy-6-(2-propenyl)- (9ci)	HMDB
1-Allyl-2,3-dimethoxy-4,5-(methylenedioxy)-benzene	HMDB
1-Allyl-2,3-dimethoxy-4,5-methylenedioxybenzene	HMDB
4,5-Dimethoxy-6-(2-propenyl)-1,3-benzodioxole	HMDB
4,5-Dimethoxy-6-(2-propenyl)-1,3-benzodioxole, 9ci	HMDB
6-Allyl-4,5-dimethoxy-1,3-benzodioxole	HMDB
Apiole (dill)	HMDB
Dill apiol	HMDB
Dill apiole	HMDB
Dillapiole	HMDB
Dillapiol	KEGG

Chemical Formula

C₁₂H₁₄O₄

Average Molecular Weight

222.2372

Monoisotopic Molecular Weight

222.089208936

IUPAC Name

4,5-dimethoxy-6-(prop-2-en-1-yl)-2H-1,3-benzodioxole

Traditional Name

dillapiol

CAS Registry Number

484-31-1

SMILES

COC1=C(OC)C(CC=C)=CC2=C1OCO2

InChI Identifier

InChI=1S/C12H14O4/c1-4-5-8-6-9-11(16-7-15-9)12(14-3)10(8)13-2/h4,6H,1,5,7H2,2-3H3

InChI Key

LIKYNOPXHGPMIH-UHFFFAOYSA-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
Anisole
Alkyl aryl ether
Benzenoid
Oxacycle
Ether
Acetal
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

benzodioxoles (CHEBI:70453 )

Ontology

Cellular substructure

Extracellular (HMDB: HMDB0030725)
Cytoplasm (HMDB: HMDB0030725)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030725)

Source

Exogenous

Exogenous (HMDB: HMDB0030725)

Food

Food (HMDB: HMDB0030725)

Herb and spice

Herb

Coriander (FooDB: FOOD00061)
Dill (FooDB: FOOD00013)
Fennel (FooDB: FOOD00082)
Parsley (FooDB: FOOD00131)

Spice

Cumin (FooDB: FOOD00067)

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Plant

Plant (HMDB: HMDB0030725)

Process

Not Available

Role

Biological role

Anti bacterial (HMDB: HMDB0030725)

Industrial application

Agriculture

Pesticide

Insecticide (HMDB: HMDB0030725)

Pesticide (HMDB: HMDB0030725)

Molluscicide (HMDB: HMDB0030725)

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

Sedative (HMDB: HMDB0030725)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	29.5 °C	Not Available
Boiling Point	285.00 to 292.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	27.68 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	2.343 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.65 g/L	ALOGPS
logP	2.33	ALOGPS
logP	2.38	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	36.92 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	59.04 m³·mol⁻¹	ChemAxon
Polarizability	22.94 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	151.563	31661259
DarkChem	[M-H]-	148.937	31661259
DeepCCS	[M+H]+	143.438	30932474
DeepCCS	[M-H]-	140.915	30932474
DeepCCS	[M-2H]-	176.516	30932474
DeepCCS	[M+Na]+	152.054	30932474
AllCCS	[M+H]+	148.1	32859911
AllCCS	[M+H-H2O]+	144.0	32859911
AllCCS	[M+NH4]+	151.9	32859911
AllCCS	[M+Na]+	153.0	32859911
AllCCS	[M-H]-	150.7	32859911
AllCCS	[M+Na-2H]-	150.7	32859911
AllCCS	[M+HCOO]-	150.9	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. Predicted by Afia on May 17, 2022.	5.74 minutes	32390414
Predicted by Siyang on May 30, 2022	16.2744 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.97 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2210.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	498.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	203.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	314.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	158.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	618.8 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	822.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	140.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1382.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	502.3 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	1561.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	473.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	392.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	523.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	585.6 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	18.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dillapiol	COC1=C(OC)C(CC=C)=CC2=C1OCO2	2433.1	Standard polar	33892256
Dillapiol	COC1=C(OC)C(CC=C)=CC2=C1OCO2	1601.1	Standard non polar	33892256
Dillapiol	COC1=C(OC)C(CC=C)=CC2=C1OCO2	1625.8	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 - Dillapiol GC-MS (Non-derivatized) - 70eV, Positive	splash10-052f-1930000000-759fd9f5828da82064eb	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dillapiol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-00di-9660000000-7cd909d21ca4a4c8bb1e	2015-03-01	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dillapiol 10V, Positive-QTOF	splash10-00di-0190000000-65afe20a9d6ea8212ae4	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dillapiol 20V, Positive-QTOF	splash10-00dl-2490000000-a585b5b3566814b251fc	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dillapiol 40V, Positive-QTOF	splash10-03g3-6900000000-e4d0d60144cac96a91bb	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dillapiol 10V, Negative-QTOF	splash10-00di-0090000000-a993c42f8477ed292846	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dillapiol 20V, Negative-QTOF	splash10-00di-0690000000-969d0f40c3543ae56108	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dillapiol 40V, Negative-QTOF	splash10-0040-7900000000-72a37bef985f024191df	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dillapiol 10V, Positive-QTOF	splash10-00di-0090000000-434847f7ec0085e24b80	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dillapiol 20V, Positive-QTOF	splash10-00di-0390000000-7be09d177fcf76fa1e71	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dillapiol 40V, Positive-QTOF	splash10-0ldi-9520000000-f36f591d0e5c5b2747dd	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dillapiol 10V, Negative-QTOF	splash10-00di-0090000000-e696c56af8179794e7ad	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dillapiol 20V, Negative-QTOF	splash10-00di-0970000000-d9ab44e0dc7f91b8576e	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dillapiol 40V, Negative-QTOF	splash10-03fr-9700000000-dc4990fb9e6601280905	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Dillapiole

METLIN ID

Not Available

PubChem Compound

10231

PDB ID

Not Available

ChEBI ID

544678

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1019661

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 Dillapiol (HMDB0030725)

MOL for HMDB0030725 (Dillapiol)

3D MOL for HMDB0030725 (Dillapiol)

3D SDF for HMDB0030725 (Dillapiol)

3D-SDF for HMDB0030725 (Dillapiol)

PDB for HMDB0030725 (Dillapiol)

3D PDB for HMDB0030725 (Dillapiol)

SMILES for HMDB0030725 (Dillapiol)

INCHI for HMDB0030725 (Dillapiol)

Structure for HMDB0030725 (Dillapiol)

3D Structure for HMDB0030725 (Dillapiol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra