Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:29:41 UTC

Update Date

2022-03-07 02:53:50 UTC

HMDB ID

HMDB0033735

Secondary Accession Numbers

HMDB33735

Metabolite Identification

Common Name

Graveolone

Description

Graveolone belongs to the class of organic compounds known as linear pyranocoumarins. These are organic compounds containing a pyran (or a hydrogenated derivative) linearly fused to a coumarin moiety. Graveolone has been detected, but not quantified in, a few different foods, such as dills (Anethum graveolens), herbs and spices, and parsleys (Petroselinum crispum). This could make graveolone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Graveolone.

Structure

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

HMDB0033735
     RDKit          3D
Graveolone
 30 32  0  0  0  0  0  0  0  0999 V2000
   -3.5933    0.5503    1.2139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5278    0.0706    0.2200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0940   -1.1206   -0.5403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3146    1.1763   -0.7589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0025    0.9974   -1.4372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8185    1.2833   -2.6495 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1233    0.4698   -0.6752 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4335    0.5613   -1.0963 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4904    0.0596   -0.3692 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8022    0.1453   -0.7798 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8467   -0.3668   -0.0310 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5257   -0.9824    1.1717 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4201   -1.4727    1.9089 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2809   -1.0572    1.5494 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2646   -0.5685    0.8384 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9574   -0.6670    1.2719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0985   -0.1595    0.5340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3928   -0.2625    0.9733 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0404    1.1570    1.9751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3411    1.1953    0.7218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0448   -0.3146    1.7424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1717   -0.9375   -0.7482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5491   -1.2261   -1.4973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0141   -2.0534    0.0342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2762    2.1329   -0.1873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1548    1.1617   -1.4806 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6079    1.0555   -2.0460 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0244    0.6285   -1.7184 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8844   -0.2933   -0.3665 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7726   -1.1628    2.2265 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18  2  1  0
 17  7  1  0
 15  9  2  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  8 27  1  0
 10 28  1  0
 11 29  1  0
 16 30  1  0
M  END

  Mrv0541 02241220172D          

 18 20  0  0  0  0            999 V2000
   -4.8027   -4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5171   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5171   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8027   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0882   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0882   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3737   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3737   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6593   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6593   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2316   -4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9448   -4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9448   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2304   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2304   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9448   -7.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5159   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5159   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  1  6  1  0  0  0  0
  7  6  1  0  0  0  0
  6  5  2  0  0  0  0
  5  8  1  0  0  0  0
  8  9  2  0  0  0  0
  7 10  2  0  0  0  0
  2 11  2  0  0  0  0
 12 10  1  0  0  0  0
 10  9  1  0  0  0  0
  9 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 12 15  1  0  0  0  0
 13 16  2  0  0  0  0
 15 17  1  0  0  0  0
 15 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033735

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1(C)CC(=O)C2=CC3=C(OC(=O)C=C3)C=C2O1

> <INCHI_IDENTIFIER>
InChI=1S/C14H12O4/c1-14(2)7-10(15)9-5-8-3-4-13(16)17-11(8)6-12(9)18-14/h3-6H,7H2,1-2H3

> <INCHI_KEY>
WEDGVCZUPFZNDE-UHFFFAOYSA-N

> <FORMULA>
C14H12O4

> <MOLECULAR_WEIGHT>
244.2427

> <EXACT_MASS>
244.073558872

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
24.86595039297392

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
13,13-dimethyl-4,14-dioxatricyclo[8.4.0.0³,⁸]tetradeca-1,3(8),6,9-tetraene-5,11-dione

> <ALOGPS_LOGP>
2.37

> <JCHEM_LOGP>
1.8188293203333334

> <ALOGPS_LOGS>
-3.47

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.011300740673128

> <JCHEM_PKA_STRONGEST_BASIC>
-4.924175223851121

> <JCHEM_POLAR_SURFACE_AREA>
52.6

> <JCHEM_REFRACTIVITY>
65.6119

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.18e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
13,13-dimethyl-4,14-dioxatricyclo[8.4.0.0³,⁸]tetradeca-1,3(8),6,9-tetraene-5,11-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0033735
     RDKit          3D
Graveolone
 30 32  0  0  0  0  0  0  0  0999 V2000
   -3.5933    0.5503    1.2139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5278    0.0706    0.2200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0940   -1.1206   -0.5403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3146    1.1763   -0.7589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0025    0.9974   -1.4372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8185    1.2833   -2.6495 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1233    0.4698   -0.6752 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4335    0.5613   -1.0963 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4904    0.0596   -0.3692 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8022    0.1453   -0.7798 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8467   -0.3668   -0.0310 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5257   -0.9824    1.1717 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4201   -1.4727    1.9089 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2809   -1.0572    1.5494 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2646   -0.5685    0.8384 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9574   -0.6670    1.2719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0985   -0.1595    0.5340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3928   -0.2625    0.9733 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0404    1.1570    1.9751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3411    1.1953    0.7218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0448   -0.3146    1.7424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1717   -0.9375   -0.7482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5491   -1.2261   -1.4973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0141   -2.0534    0.0342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2762    2.1329   -0.1873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1548    1.1617   -1.4806 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6079    1.0555   -2.0460 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0244    0.6285   -1.7184 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8844   -0.2933   -0.3665 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7726   -1.1628    2.2265 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18  2  1  0
 17  7  1  0
 15  9  2  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  8 27  1  0
 10 28  1  0
 11 29  1  0
 16 30  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  O   UNK     0      -8.965  -8.470   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0     -10.299  -9.240   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -10.299 -10.780   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -8.965 -11.550   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -7.631 -10.780   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -7.631  -9.240   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -6.298  -8.470   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -6.298 -11.550   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.964 -10.780   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.964  -9.240   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0     -11.632  -8.470   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -3.630  -8.470   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -3.630 -11.550   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.297 -10.780   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.297  -9.240   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -3.630 -13.090   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -0.963  -8.470   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.963 -10.010   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   11                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    8                                                  
CONECT    6    1    7    5                                                  
CONECT    7    6   10                                                       
CONECT    8    5    9                                                       
CONECT    9    8   10   13                                                  
CONECT   10    7   12    9                                                  
CONECT   11    2                                                            
CONECT   12   10   15                                                       
CONECT   13    9   14   16                                                  
CONECT   14   13   15                                                       
CONECT   15   14   12   17   18                                             
CONECT   16   13                                                            
CONECT   17   15                                                            
CONECT   18   15                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   40    0
END

COMPND    HMDB0033735
HETATM    1  C1  UNL     1      -3.593   0.550   1.214  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.528   0.071   0.220  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.094  -1.121  -0.540  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.315   1.176  -0.759  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.002   0.997  -1.437  1.00  0.00           C  
HETATM    6  O1  UNL     1      -0.819   1.283  -2.649  1.00  0.00           O  
HETATM    7  C6  UNL     1       0.123   0.470  -0.675  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.434   0.561  -1.096  1.00  0.00           C  
HETATM    9  C8  UNL     1       2.490   0.060  -0.369  1.00  0.00           C  
HETATM   10  C9  UNL     1       3.802   0.145  -0.780  1.00  0.00           C  
HETATM   11  C10 UNL     1       4.847  -0.367  -0.031  1.00  0.00           C  
HETATM   12  C11 UNL     1       4.526  -0.982   1.172  1.00  0.00           C  
HETATM   13  O2  UNL     1       5.420  -1.473   1.909  1.00  0.00           O  
HETATM   14  O3  UNL     1       3.281  -1.057   1.549  1.00  0.00           O  
HETATM   15  C12 UNL     1       2.265  -0.568   0.838  1.00  0.00           C  
HETATM   16  C13 UNL     1       0.957  -0.667   1.272  1.00  0.00           C  
HETATM   17  C14 UNL     1      -0.098  -0.160   0.534  1.00  0.00           C  
HETATM   18  O4  UNL     1      -1.393  -0.263   0.973  1.00  0.00           O  
HETATM   19  H1  UNL     1      -3.040   1.157   1.975  1.00  0.00           H  
HETATM   20  H2  UNL     1      -4.341   1.195   0.722  1.00  0.00           H  
HETATM   21  H3  UNL     1      -4.045  -0.315   1.742  1.00  0.00           H  
HETATM   22  H4  UNL     1      -4.172  -0.938  -0.748  1.00  0.00           H  
HETATM   23  H5  UNL     1      -2.549  -1.226  -1.497  1.00  0.00           H  
HETATM   24  H6  UNL     1      -3.014  -2.053   0.034  1.00  0.00           H  
HETATM   25  H7  UNL     1      -2.276   2.133  -0.187  1.00  0.00           H  
HETATM   26  H8  UNL     1      -3.155   1.162  -1.481  1.00  0.00           H  
HETATM   27  H9  UNL     1       1.608   1.056  -2.046  1.00  0.00           H  
HETATM   28  H10 UNL     1       4.024   0.629  -1.718  1.00  0.00           H  
HETATM   29  H11 UNL     1       5.884  -0.293  -0.366  1.00  0.00           H  
HETATM   30  H12 UNL     1       0.773  -1.163   2.227  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3    4   18
CONECT    3   22   23   24
CONECT    4    5   25   26
CONECT    5    6    6    7
CONECT    7    8    8   17
CONECT    8    9   27
CONECT    9   10   15   15
CONECT   10   11   11   28
CONECT   11   12   29
CONECT   12   13   13   14
CONECT   14   15
CONECT   15   16
CONECT   16   17   17   30
CONECT   17   18
END

HMDB0033735
     RDKit          3D
Graveolone
 30 32  0  0  0  0  0  0  0  0999 V2000
   -3.5933    0.5503    1.2139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5278    0.0706    0.2200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0940   -1.1206   -0.5403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3146    1.1763   -0.7589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0025    0.9974   -1.4372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8185    1.2833   -2.6495 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1233    0.4698   -0.6752 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4335    0.5613   -1.0963 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4904    0.0596   -0.3692 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8022    0.1453   -0.7798 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8467   -0.3668   -0.0310 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5257   -0.9824    1.1717 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4201   -1.4727    1.9089 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2809   -1.0572    1.5494 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2646   -0.5685    0.8384 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9574   -0.6670    1.2719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0985   -0.1595    0.5340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3928   -0.2625    0.9733 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0404    1.1570    1.9751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3411    1.1953    0.7218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0448   -0.3146    1.7424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1717   -0.9375   -0.7482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5491   -1.2261   -1.4973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0141   -2.0534    0.0342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2762    2.1329   -0.1873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1548    1.1617   -1.4806 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6079    1.0555   -2.0460 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0244    0.6285   -1.7184 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8844   -0.2933   -0.3665 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7726   -1.1628    2.2265 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18  2  1  0
 17  7  1  0
 15  9  2  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  8 27  1  0
 10 28  1  0
 11 29  1  0
 16 30  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
6,7-dihydro-8,8-Dimethyl-2H,8H-benzo-(1,2b:5,4')-dipyran-2,6-dione	HMDB
6,7-dihydro-8,8-Dimethyl-2H,8H-benzo[1,2-b:5,4-b']dipyran-2,6-dione	HMDB
8,8-Dimethyl-7,8-dihydro-pyrano[3,2-g]chromene-2,6-dione	HMDB

Chemical Formula

C₁₄H₁₂O₄

Average Molecular Weight

244.2427

Monoisotopic Molecular Weight

244.073558872

IUPAC Name

13,13-dimethyl-4,14-dioxatricyclo[8.4.0.0³,⁸]tetradeca-1,3(8),6,9-tetraene-5,11-dione

Traditional Name

13,13-dimethyl-4,14-dioxatricyclo[8.4.0.0³,⁸]tetradeca-1,3(8),6,9-tetraene-5,11-dione

CAS Registry Number

16499-05-1

SMILES

CC1(C)CC(=O)C2=CC3=C(OC(=O)C=C3)C=C2O1

InChI Identifier

InChI=1S/C14H12O4/c1-14(2)7-10(15)9-5-8-3-4-13(16)17-11(8)6-12(9)18-14/h3-6H,7H2,1-2H3

InChI Key

WEDGVCZUPFZNDE-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as linear pyranocoumarins. These are organic compounds containing a pyran (or a hydrogenated derivative) linearly fused to a coumarin moiety.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Pyranocoumarins

Direct Parent

Linear pyranocoumarins

Alternative Parents

Substituents

Linear pyranocoumarin
Pyranochromene
2,2-dimethyl-1-benzopyran
Chromone
Chromane
Benzopyran
1-benzopyran
Aryl alkyl ketone
Aryl ketone
Alkyl aryl ether
Pyranone
Benzenoid
Pyran
Heteroaromatic compound
Ketone
Lactone
Ether
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0033735)
Cytoplasm (HMDB: HMDB0033735)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033735)

Source

Exogenous

Exogenous (HMDB: HMDB0033735)

Food

Food (HMDB: HMDB0033735)

Herb and spice

Herb

Dill (FooDB: FOOD00013)
Parsley (FooDB: FOOD00131)

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Plant

Plant (HMDB: HMDB0033735)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0033735)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	177.5 - 178 °C	Not Available
Boiling Point	439.00 to 440.00 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	467.2 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	2.670 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.082 g/L	ALOGPS
logP	2.37	ALOGPS
logP	1.82	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	15.01	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	52.6 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	65.61 m³·mol⁻¹	ChemAxon
Polarizability	24.87 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	156.903	31661259
DarkChem	[M-H]-	154.389	31661259
DeepCCS	[M+H]+	160.572	30932474
DeepCCS	[M-H]-	158.214	30932474
DeepCCS	[M-2H]-	191.1	30932474
DeepCCS	[M+Na]+	166.665	30932474
AllCCS	[M+H]+	152.7	32859911
AllCCS	[M+H-H2O]+	148.6	32859911
AllCCS	[M+NH4]+	156.5	32859911
AllCCS	[M+Na]+	157.6	32859911
AllCCS	[M-H]-	158.1	32859911
AllCCS	[M+Na-2H]-	157.6	32859911
AllCCS	[M+HCOO]-	157.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Graveolone	CC1(C)CC(=O)C2=CC3=C(OC(=O)C=C3)C=C2O1	3074.0	Standard polar	33892256
Graveolone	CC1(C)CC(=O)C2=CC3=C(OC(=O)C=C3)C=C2O1	2219.5	Standard non polar	33892256
Graveolone	CC1(C)CC(=O)C2=CC3=C(OC(=O)C=C3)C=C2O1	2210.1	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 - Graveolone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0v04-1490000000-7a6369d0bc5de809c822	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Graveolone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Graveolone 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 - Graveolone 10V, Negative-QTOF	splash10-0006-0190000000-99d4fe5456bf67dcebe3	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Graveolone 20V, Negative-QTOF	splash10-0006-0490000000-8381a207dd70772c1cfc	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Graveolone 40V, Negative-QTOF	splash10-0a4u-4910000000-a9e396f685ac07b07483	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Graveolone 10V, Negative-QTOF	splash10-0006-0090000000-c3ceff739ebba19f299c	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Graveolone 20V, Negative-QTOF	splash10-0006-0090000000-9acfa2e26a204df2f25a	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Graveolone 40V, Negative-QTOF	splash10-004i-0790000000-15e9b26d19629b4e0947	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Graveolone 10V, Positive-QTOF	splash10-0002-0190000000-f8c8fdb3c697796b2901	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Graveolone 20V, Positive-QTOF	splash10-000b-2490000000-0a2c1ec23384a04b14d5	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Graveolone 40V, Positive-QTOF	splash10-052s-5900000000-c5eda937cca4cc3ed621	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Graveolone 10V, Positive-QTOF	splash10-0002-0090000000-5665d475819ffb7ca28c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Graveolone 20V, Positive-QTOF	splash10-0002-0190000000-c4ba5da418678027f39d	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Graveolone 40V, Positive-QTOF	splash10-0a70-2930000000-5dbca00f9547c335e286	2021-09-23	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

FDB011859

KNApSAcK ID

C00054134

Chemspider ID

154741

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

177751

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1583871

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.. .
(). Ashok S. Mujumdar and Ramesh N. Usgaonkar, â€œBenzodipyrans. Part V. Synthesis of a linear dihydrobenzodipyrandione isolated from dill and of other similar benzodipyrandiones,â€ Journal of the Chemical Society, Perkin Transactions 1 (1974): 2236-2239. [Structure]. .

Showing metabocard for Graveolone (HMDB0033735)

MOL for HMDB0033735 (Graveolone)

3D MOL for HMDB0033735 (Graveolone)

3D SDF for HMDB0033735 (Graveolone)

3D-SDF for HMDB0033735 (Graveolone)

PDB for HMDB0033735 (Graveolone)

3D PDB for HMDB0033735 (Graveolone)

SMILES for HMDB0033735 (Graveolone)

INCHI for HMDB0033735 (Graveolone)

Structure for HMDB0033735 (Graveolone)

3D Structure for HMDB0033735 (Graveolone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra