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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:32:18 UTC

Update Date

2022-03-07 02:53:51 UTC

HMDB ID

HMDB0033776

Secondary Accession Numbers

HMDB33776

Metabolite Identification

Common Name

Apiole

Description

Apiole is found in dill. Apiole occurs in Sassafras albidum (sassafras) and Anethum graveolens (dill) Apiol is an organic chemical compound, also known as parsley apiol, apiole or parsley camphor. It is found in celery, parsley seeds, and the essential oil of parsley. Heinrich Christoph Link, an apothecary in Leipzig, discovered the substance in 1715 as greenish crystals reduced by steam from oil of parsley. In 1855 Joret and Homolle discovered that apiol was an effective treatment of amenorrea or lack of menstruation. In medicine it has been used, as essential oil or in purified form, for the treatment of menstrual disorders. It is an irritant and in high doses it is toxic and can cause liver and kidney damage.

Structure

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

HMDB0033776
     RDKit          3D
Apiole
 30 31  0  0  0  0  0  0  0  0999 V2000
    3.4945    1.5334    1.4122 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8268    0.4502    1.0520 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0013    0.4760   -0.1664 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5819    0.2025    0.0967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3518    1.2139    0.0950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6822    0.9553    0.3414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5972    1.9885    0.3335 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1274    3.2914    0.0687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0701   -0.3655    0.5956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1475   -1.3862    0.6005 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1800   -1.0923    0.3493 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1140   -2.0850    0.3481 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4963   -2.8427   -0.7783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8369   -2.5476    0.8791 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1941   -2.2984    0.5738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3361   -0.9001    0.8722 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4325    2.4382    0.8094 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1240    1.5660    2.3116 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9269   -0.4221    1.6917 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1731    1.4339   -0.6894 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4219   -0.3035   -0.8706 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0332    2.2155   -0.1120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5060    3.3361   -0.8438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0307    3.9351   -0.0844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5247    3.6635    0.9267 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6033   -2.7937   -0.8350 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0800   -2.4499   -1.7244 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1402   -3.8813   -0.5974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8858   -2.8934    1.2026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3392   -2.4375   -0.5078 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  1  0
  7  8  1  0
  6  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 10 14  1  0
 14 15  1  0
 15 16  1  0
 11  4  1  0
 16  9  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
  8 23  1  0
  8 24  1  0
  8 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

  Mrv0541 05061307212D          

 16 17  0  0  0  0            999 V2000
    4.7812    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.5396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  2  0  0  0  0
  5  4  1  0  0  0  0
  8  5  1  0  0  0  0
  8  6  2  0  0  0  0
  9  6  1  0  0  0  0
 10  8  1  0  0  0  0
 11  9  2  0  0  0  0
 12 10  2  0  0  0  0
 12 11  1  0  0  0  0
 13  2  1  0  0  0  0
 13  9  1  0  0  0  0
 14  3  1  0  0  0  0
 14 10  1  0  0  0  0
 15  7  1  0  0  0  0
 15 11  1  0  0  0  0
 16  7  1  0  0  0  0
 16 12  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033776

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C2OCOC2=C(OC)C(CC=C)=C1

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

> <INCHI_KEY>
QQRSPHJOOXUALR-UHFFFAOYSA-N

> <FORMULA>
C12H14O4

> <MOLECULAR_WEIGHT>
222.2372

> <EXACT_MASS>
222.089208936

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
22.87027944669294

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4,7-dimethoxy-5-(prop-2-en-1-yl)-2H-1,3-benzodioxole

> <ALOGPS_LOGP>
2.34

> <JCHEM_LOGP>
2.3797074853333333

> <ALOGPS_LOGS>
-2.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.39471840723923

> <JCHEM_POLAR_SURFACE_AREA>
36.92

> <JCHEM_REFRACTIVITY>
59.03860000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.33e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
apiol

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0033776
     RDKit          3D
Apiole
 30 31  0  0  0  0  0  0  0  0999 V2000
    3.4945    1.5334    1.4122 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8268    0.4502    1.0520 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0013    0.4760   -0.1664 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5819    0.2025    0.0967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3518    1.2139    0.0950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6822    0.9553    0.3414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5972    1.9885    0.3335 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1274    3.2914    0.0687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0701   -0.3655    0.5956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1475   -1.3862    0.6005 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1800   -1.0923    0.3493 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1140   -2.0850    0.3481 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4963   -2.8427   -0.7783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8369   -2.5476    0.8791 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1941   -2.2984    0.5738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3361   -0.9001    0.8722 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4325    2.4382    0.8094 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1240    1.5660    2.3116 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9269   -0.4221    1.6917 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1731    1.4339   -0.6894 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4219   -0.3035   -0.8706 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0332    2.2155   -0.1120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5060    3.3361   -0.8438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0307    3.9351   -0.0844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5247    3.6635    0.9267 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6033   -2.7937   -0.8350 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0800   -2.4499   -1.7244 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1402   -3.8813   -0.5974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8858   -2.8934    1.2026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3392   -2.4375   -0.5078 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  1  0
  7  8  1  0
  6  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 10 14  1  0
 14 15  1  0
 15 16  1  0
 11  4  1  0
 16  9  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
  8 23  1  0
  8 24  1  0
  8 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                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       8.925   6.693   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.258  -1.007   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.590   6.693   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.591   5.923   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.591   4.383   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       4.924  -0.237   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       4.924   5.923   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       2.126   1.597   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       2.126   4.089   0.000  0.00  0.00           O+0
CONECT    1    4                                                            
CONECT    2   13                                                            
CONECT    3   14                                                            
CONECT    4    1    5                                                       
CONECT    5    4    8                                                       
CONECT    6    8    9                                                       
CONECT    7   15   16                                                       
CONECT    8    5    6   10                                                  
CONECT    9    6   11   13                                                  
CONECT   10    8   12   14                                                  
CONECT   11    9   12   15                                                  
CONECT   12   10   11   16                                                  
CONECT   13    2    9                                                       
CONECT   14    3   10                                                       
CONECT   15    7   11                                                       
CONECT   16    7   12                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

COMPND    HMDB0033776
HETATM    1  C1  UNL     1       3.494   1.533   1.412  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.827   0.450   1.052  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.001   0.476  -0.166  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.582   0.202   0.097  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.352   1.214   0.095  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.682   0.955   0.341  1.00  0.00           C  
HETATM    7  O1  UNL     1      -2.597   1.988   0.333  1.00  0.00           O  
HETATM    8  C7  UNL     1      -2.127   3.291   0.069  1.00  0.00           C  
HETATM    9  C8  UNL     1      -2.070  -0.366   0.596  1.00  0.00           C  
HETATM   10  C9  UNL     1      -1.148  -1.386   0.601  1.00  0.00           C  
HETATM   11  C10 UNL     1       0.180  -1.092   0.349  1.00  0.00           C  
HETATM   12  O2  UNL     1       1.114  -2.085   0.348  1.00  0.00           O  
HETATM   13  C11 UNL     1       1.496  -2.843  -0.778  1.00  0.00           C  
HETATM   14  O3  UNL     1      -1.837  -2.548   0.879  1.00  0.00           O  
HETATM   15  C12 UNL     1      -3.194  -2.298   0.574  1.00  0.00           C  
HETATM   16  O4  UNL     1      -3.336  -0.900   0.872  1.00  0.00           O  
HETATM   17  H1  UNL     1       3.432   2.438   0.809  1.00  0.00           H  
HETATM   18  H2  UNL     1       4.124   1.566   2.312  1.00  0.00           H  
HETATM   19  H3  UNL     1       2.927  -0.422   1.692  1.00  0.00           H  
HETATM   20  H4  UNL     1       2.173   1.434  -0.689  1.00  0.00           H  
HETATM   21  H5  UNL     1       2.422  -0.303  -0.871  1.00  0.00           H  
HETATM   22  H6  UNL     1       0.033   2.216  -0.112  1.00  0.00           H  
HETATM   23  H7  UNL     1      -1.506   3.336  -0.844  1.00  0.00           H  
HETATM   24  H8  UNL     1      -3.031   3.935  -0.084  1.00  0.00           H  
HETATM   25  H9  UNL     1      -1.525   3.663   0.927  1.00  0.00           H  
HETATM   26  H10 UNL     1       2.603  -2.794  -0.835  1.00  0.00           H  
HETATM   27  H11 UNL     1       1.080  -2.450  -1.724  1.00  0.00           H  
HETATM   28  H12 UNL     1       1.140  -3.881  -0.597  1.00  0.00           H  
HETATM   29  H13 UNL     1      -3.886  -2.893   1.203  1.00  0.00           H  
HETATM   30  H14 UNL     1      -3.339  -2.438  -0.508  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    9    9
CONECT    7    8
CONECT    8   23   24   25
CONECT    9   10   16
CONECT   10   11   11   14
CONECT   11   12
CONECT   12   13
CONECT   13   26   27   28
CONECT   14   15
CONECT   15   16   29   30
END

HMDB0033776
     RDKit          3D
Apiole
 30 31  0  0  0  0  0  0  0  0999 V2000
    3.4945    1.5334    1.4122 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8268    0.4502    1.0520 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0013    0.4760   -0.1664 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5819    0.2025    0.0967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3518    1.2139    0.0950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6822    0.9553    0.3414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5972    1.9885    0.3335 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1274    3.2914    0.0687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0701   -0.3655    0.5956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1475   -1.3862    0.6005 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1800   -1.0923    0.3493 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1140   -2.0850    0.3481 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4963   -2.8427   -0.7783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8369   -2.5476    0.8791 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1941   -2.2984    0.5738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3361   -0.9001    0.8722 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4325    2.4382    0.8094 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1240    1.5660    2.3116 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9269   -0.4221    1.6917 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1731    1.4339   -0.6894 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4219   -0.3035   -0.8706 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0332    2.2155   -0.1120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5060    3.3361   -0.8438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0307    3.9351   -0.0844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5247    3.6635    0.9267 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6033   -2.7937   -0.8350 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0800   -2.4499   -1.7244 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1402   -3.8813   -0.5974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8858   -2.8934    1.2026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3392   -2.4375   -0.5078 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  1  0
  7  8  1  0
  6  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 10 14  1  0
 14 15  1  0
 15 16  1  0
 11  4  1  0
 16  9  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
  8 23  1  0
  8 24  1  0
  8 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
1-Allyl-2,5-dimethoxy-3, 4-(methylenedioxy)benzene	HMDB
1-Allyl-2,5-dimethoxy-3,4-(methylenedioxy)-benzene	HMDB
1-Allyl-2,5-dimethoxy-3,4-(methylenedioxy)benzene	HMDB
1-Allyl-2,5-dimethoxy-3,4-methylenedioxybenzene	HMDB, MeSH
4,7-Dimethoxy-5-(2-propen-1-yl)-1,3-benzodioxole	HMDB, MeSH
4,7-Dimethoxy-5-(2-propenyl)-1,3-benzodioxole	HMDB
4,7-Dimethoxy-5-(2-propenyl)-1,3-benzodioxole, 9ci	HMDB
5-Allyl-4,7-dimethoxy-1,3-benzodioxol	HMDB
5-Allyl-4,7-dimethoxy-1,3-benzodioxole	HMDB
Apiol	HMDB
Apiole (parsley)	HMDB
Apioline	HMDB
Camphre de persil	HMDB
Parsley apiol	HMDB
Parsley apiole	HMDB
Parsley camphor	HMDB
Petersiliencampher	HMDB

Chemical Formula

C₁₂H₁₄O₄

Average Molecular Weight

222.2372

Monoisotopic Molecular Weight

222.089208936

IUPAC Name

4,7-dimethoxy-5-(prop-2-en-1-yl)-2H-1,3-benzodioxole

Traditional Name

apiol

CAS Registry Number

523-80-8

SMILES

COC1=C2OCOC2=C(OC)C(CC=C)=C1

InChI Identifier

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

InChI Key

QQRSPHJOOXUALR-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:70353 )

Ontology

Cellular substructure

Extracellular (HMDB: HMDB0033776)
Cytoplasm (HMDB: HMDB0033776)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033776)

Source

Exogenous

Exogenous (HMDB: HMDB0033776)

Food

Food (HMDB: HMDB0033776)

Herb and spice

Spice

Wild celery (FooDB: FOOD00015)

Herb

Dill (FooDB: FOOD00013)
Fennel (FooDB: FOOD00082)
Parsley (FooDB: FOOD00131)
Lovage (FooDB: FOOD00100)

Herbs and Spices (FooDB: FOOD00866)

Tea

Endogenous

Plant

Plant (HMDB: HMDB0033776)

Process

Not Available

Role

Biological role

Industrial application

Abortifacient (HMDB: HMDB0033776)
Antipyretic (HMDB: HMDB0033776)
Central nervous system stimulant (HMDB: HMDB0033776)
Vasodilator agent (HMDB: HMDB0033776)

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

Diuretic (HMDB: HMDB0033776)

Agriculture

Pesticide

Insecticide (HMDB: HMDB0033776)

Pesticide (HMDB: HMDB0033776)

Indirect biological role

Metabotoxin

Reprotoxin (HMDB: HMDB0033776)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	30 °C	Not Available
Boiling Point	294.00 to 295.00 °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	3.481 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	146.083	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001126

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.63 g/L	ALOGPS
logP	2.34	ALOGPS
logP	2.38	ChemAxon
logS	-2.6	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	22.87 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]+	152.014	31661259
DarkChem	[M-H]-	147.429	31661259
DeepCCS	[M+H]+	147.452	30932474
DeepCCS	[M-H]-	145.094	30932474
DeepCCS	[M-2H]-	179.407	30932474
DeepCCS	[M+Na]+	154.028	30932474
AllCCS	[M+H]+	148.2	32859911
AllCCS	[M+H-H2O]+	144.1	32859911
AllCCS	[M+NH4]+	152.0	32859911
AllCCS	[M+Na]+	153.1	32859911
AllCCS	[M-H]-	150.8	32859911
AllCCS	[M+Na-2H]-	150.9	32859911
AllCCS	[M+HCOO]-	151.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Apiole	COC1=C2OCOC2=C(OC)C(CC=C)=C1	2478.7	Standard polar	33892256
Apiole	COC1=C2OCOC2=C(OC)C(CC=C)=C1	1647.8	Standard non polar	33892256
Apiole	COC1=C2OCOC2=C(OC)C(CC=C)=C1	1684.7	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 - Apiole GC-MS (Non-derivatized) - 70eV, Positive	splash10-052f-2920000000-1cc8f418618578cdd948	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Apiole GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Apiole GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-00di-5890000000-b5cf6efedda43e9d694c	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 - Apiole 10V, Positive-QTOF	splash10-00di-0190000000-2a13687cd8d861844f6a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Apiole 20V, Positive-QTOF	splash10-00di-2390000000-527ad08f36c5b6d7fc09	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Apiole 40V, Positive-QTOF	splash10-03di-3900000000-54ca6ec7708d663c0eec	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Apiole 10V, Negative-QTOF	splash10-00di-0090000000-2497b3799235c68f1f37	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Apiole 20V, Negative-QTOF	splash10-00di-0690000000-e9c82cedbafb1cfbb38d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Apiole 40V, Negative-QTOF	splash10-0aos-3900000000-4c9e9c13ad062d6f79d3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Apiole 10V, Negative-QTOF	splash10-00di-0090000000-e696c56af8179794e7ad	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Apiole 20V, Negative-QTOF	splash10-00dl-0980000000-013e17a78d3735e96600	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Apiole 40V, Negative-QTOF	splash10-004i-2900000000-d0e703a0356e829446de	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Apiole 10V, Positive-QTOF	splash10-00di-0090000000-b55ce853fd840758bfab	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Apiole 20V, Positive-QTOF	splash10-00di-0290000000-9af70ca3804ef5b209f9	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Apiole 40V, Positive-QTOF	splash10-01bc-6940000000-4f291648385a3987c36e	2021-09-24	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

Apiole

METLIN ID

Not Available

PubChem Compound

10659

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1011001

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 Apiole (HMDB0033776)

MOL for HMDB0033776 (Apiole)

3D MOL for HMDB0033776 (Apiole)

3D SDF for HMDB0033776 (Apiole)

3D-SDF for HMDB0033776 (Apiole)

PDB for HMDB0033776 (Apiole)

3D PDB for HMDB0033776 (Apiole)

SMILES for HMDB0033776 (Apiole)

INCHI for HMDB0033776 (Apiole)

Structure for HMDB0033776 (Apiole)

3D Structure for HMDB0033776 (Apiole)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra