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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:02:11 UTC

Update Date

2022-03-07 02:53:40 UTC

HMDB ID

HMDB0033321

Secondary Accession Numbers

HMDB33321

Metabolite Identification

Common Name

3,5-Dihydroxy-6,7-methylenedioxyflavanone

Description

3,5-Dihydroxy-6,7-methylenedioxyflavanone belongs to the class of organic compounds known as flavanonols. Flavanonols are compounds containing a flavan-3-one moiety, with a structure characterized by a 2-phenyl-3,4-dihydro-2H-1-benzopyran bearing a hydroxyl group and a ketone at the carbon C2 and C3, respectively. 3,5-Dihydroxy-6,7-methylenedioxyflavanone has been detected, but not quantified in, common beets (Beta vulgaris). This could make 3,5-dihydroxy-6,7-methylenedioxyflavanone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 3,5-Dihydroxy-6,7-methylenedioxyflavanone.

Structure

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

HMDB0033321
     RDKit          3D
3,5-Dihydroxy-6,7-methylenedioxyflavanone
 34 37  0  0  0  0  0  0  0  0999 V2000
    0.7070    3.0605   -0.3127 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4380    1.9020    0.0362 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4962    0.9011    0.0068 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0892   -0.4225   -0.0828 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0267   -1.4266   -0.1183 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3554   -1.0773   -0.0626 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7586    0.2354    0.0266 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8203    1.2699    0.0640 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2434    2.5517    0.1531 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1470    0.3051    0.0673 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6565   -1.0108   -0.0813 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5239   -1.8432   -0.0779 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2753   -0.6512   -0.1329 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1812    0.1291    0.6424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5499   -0.3528    0.4350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6093    0.4991    0.2699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8928   -0.0254    0.0707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1380   -1.3804    0.0334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0560   -2.2158    0.2021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7746   -1.7325    0.4010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9687    1.5896    0.4713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1865    2.3161    1.6419 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7286   -2.4417   -0.1868 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8371    3.4250    0.2007 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2222   -1.0902   -1.0431 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2842   -1.2378    0.7965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9302   -0.1042    1.7196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4419    1.5647    0.2985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6995    0.6859   -0.0551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1546   -1.7044   -0.1245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2460   -3.2951    0.1733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9294   -2.4083    0.5328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5990    2.0640   -0.3110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7013    1.9210    2.4083 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
  8  9  1  0
  7 10  1  0
 10 11  1  0
 11 12  1  0
  4 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 14 21  1  0
 21 22  1  0
 21  2  1  0
  8  3  1  0
 20 15  1  0
 12  6  1  0
  5 23  1  0
  9 24  1  0
 11 25  1  0
 11 26  1  0
 14 27  1  0
 16 28  1  0
 17 29  1  0
 18 30  1  0
 19 31  1  0
 20 32  1  0
 21 33  1  0
 22 34  1  0
M  END


  Mrv0541 05061307032D          

 22 25  0  0  0  0            999 V2000
    4.9279   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9279   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3429   -1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0734   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0734   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -3.5854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -3.5854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990   -2.7604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8580   -1.2680    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8580   -2.6029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -1.1104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  2  0  0  0  0
  8  4  2  0  0  0  0
  8  5  1  0  0  0  0
  9  6  2  0  0  0  0
 10  6  1  0  0  0  0
 11  9  1  0  0  0  0
 12 11  1  0  0  0  0
 13 11  2  0  0  0  0
 14 12  1  0  0  0  0
 15  8  1  0  0  0  0
 15 14  1  0  0  0  0
 16 10  2  0  0  0  0
 16 13  1  0  0  0  0
 17 12  2  0  0  0  0
 18 13  1  0  0  0  0
 19 14  1  0  0  0  0
 20  7  1  0  0  0  0
 20 10  1  0  0  0  0
 21  7  1  0  0  0  0
 21 16  1  0  0  0  0
 22  9  1  0  0  0  0
 22 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033321

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1C(OC2=CC3=C(OCO3)C(O)=C2C1=O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H12O6/c17-12-11-9(6-10-16(13(11)18)21-7-20-10)22-15(14(12)19)8-4-2-1-3-5-8/h1-6,14-15,18-19H,7H2

> <INCHI_KEY>
WVADKXWSLHLDCL-UHFFFAOYSA-N

> <FORMULA>
C16H12O6

> <MOLECULAR_WEIGHT>
300.2629

> <EXACT_MASS>
300.063388116

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
29.551803771666442

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,12-dihydroxy-11-phenyl-4,6,10-trioxatricyclo[7.4.0.0³,⁷]trideca-1,3(7),8-trien-13-one

> <ALOGPS_LOGP>
1.51

> <JCHEM_LOGP>
2.350313700666667

> <ALOGPS_LOGS>
-2.33

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.222867136939515

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.172122826291885

> <JCHEM_PKA_STRONGEST_BASIC>
-3.088497201808936

> <JCHEM_POLAR_SURFACE_AREA>
85.22000000000001

> <JCHEM_REFRACTIVITY>
74.43310000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.41e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,12-dihydroxy-11-phenyl-4,6,10-trioxatricyclo[7.4.0.0³,⁷]trideca-1,3(7),8-trien-13-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0033321
     RDKit          3D
3,5-Dihydroxy-6,7-methylenedioxyflavanone
 34 37  0  0  0  0  0  0  0  0999 V2000
    0.7070    3.0605   -0.3127 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4380    1.9020    0.0362 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4962    0.9011    0.0068 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0892   -0.4225   -0.0828 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0267   -1.4266   -0.1183 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3554   -1.0773   -0.0626 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7586    0.2354    0.0266 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8203    1.2699    0.0640 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2434    2.5517    0.1531 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1470    0.3051    0.0673 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6565   -1.0108   -0.0813 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5239   -1.8432   -0.0779 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2753   -0.6512   -0.1329 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1812    0.1291    0.6424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5499   -0.3528    0.4350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6093    0.4991    0.2699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8928   -0.0254    0.0707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1380   -1.3804    0.0334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0560   -2.2158    0.2021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7746   -1.7325    0.4010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9687    1.5896    0.4713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1865    2.3161    1.6419 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7286   -2.4417   -0.1868 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8371    3.4250    0.2007 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2222   -1.0902   -1.0431 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2842   -1.2378    0.7965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9302   -0.1042    1.7196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4419    1.5647    0.2985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6995    0.6859   -0.0551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1546   -1.7044   -0.1245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2460   -3.2951    0.1733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9294   -2.4083    0.5328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5990    2.0640   -0.3110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7013    1.9210    2.4083 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
  8  9  1  0
  7 10  1  0
 10 11  1  0
 11 12  1  0
  4 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 14 21  1  0
 21 22  1  0
 21  2  1  0
  8  3  1  0
 20 15  1  0
 12  6  1  0
  5 23  1  0
  9 24  1  0
 11 25  1  0
 11 26  1  0
 14 27  1  0
 16 28  1  0
 17 29  1  0
 18 30  1  0
 19 31  1  0
 20 32  1  0
 21 33  1  0
 22 34  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       9.199  -0.533   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.865   0.237   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.199  -2.073   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.531  -0.533   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.865  -2.843   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.197  -2.073   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.507  -3.613   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.531  -2.073   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.530  -2.843   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.137  -2.843   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.530  -4.383   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.864  -5.153   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.197  -5.153   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.198  -4.383   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.198  -2.843   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.137  -4.383   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       3.864  -6.693   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       1.197  -6.693   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       6.531  -5.153   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -1.602  -2.367   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -1.602  -4.859   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       3.864  -2.073   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2    8                                                       
CONECT    5    3    8                                                       
CONECT    6    9   10                                                       
CONECT    7   20   21                                                       
CONECT    8    4    5   15                                                  
CONECT    9    6   11   22                                                  
CONECT   10    6   16   20                                                  
CONECT   11    9   12   13                                                  
CONECT   12   11   14   17                                                  
CONECT   13   11   16   18                                                  
CONECT   14   12   15   19                                                  
CONECT   15    8   14   22                                                  
CONECT   16   10   13   21                                                  
CONECT   17   12                                                            
CONECT   18   13                                                            
CONECT   19   14                                                            
CONECT   20    7   10                                                       
CONECT   21    7   16                                                       
CONECT   22    9   15                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

COMPND    HMDB0033321
HETATM    1  O1  UNL     1       0.707   3.061  -0.313  1.00  0.00           O  
HETATM    2  C1  UNL     1       0.438   1.902   0.036  1.00  0.00           C  
HETATM    3  C2  UNL     1       1.496   0.901   0.007  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.089  -0.422  -0.083  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.027  -1.427  -0.118  1.00  0.00           C  
HETATM    6  C5  UNL     1       3.355  -1.077  -0.063  1.00  0.00           C  
HETATM    7  C6  UNL     1       3.759   0.235   0.027  1.00  0.00           C  
HETATM    8  C7  UNL     1       2.820   1.270   0.064  1.00  0.00           C  
HETATM    9  O2  UNL     1       3.243   2.552   0.153  1.00  0.00           O  
HETATM   10  O3  UNL     1       5.147   0.305   0.067  1.00  0.00           O  
HETATM   11  C8  UNL     1       5.656  -1.011  -0.081  1.00  0.00           C  
HETATM   12  O4  UNL     1       4.524  -1.843  -0.078  1.00  0.00           O  
HETATM   13  O5  UNL     1      -0.275  -0.651  -0.133  1.00  0.00           O  
HETATM   14  C9  UNL     1      -1.181   0.129   0.642  1.00  0.00           C  
HETATM   15  C10 UNL     1      -2.550  -0.353   0.435  1.00  0.00           C  
HETATM   16  C11 UNL     1      -3.609   0.499   0.270  1.00  0.00           C  
HETATM   17  C12 UNL     1      -4.893  -0.025   0.071  1.00  0.00           C  
HETATM   18  C13 UNL     1      -5.138  -1.380   0.033  1.00  0.00           C  
HETATM   19  C14 UNL     1      -4.056  -2.216   0.202  1.00  0.00           C  
HETATM   20  C15 UNL     1      -2.775  -1.733   0.401  1.00  0.00           C  
HETATM   21  C16 UNL     1      -0.969   1.590   0.471  1.00  0.00           C  
HETATM   22  O6  UNL     1      -1.187   2.316   1.642  1.00  0.00           O  
HETATM   23  H1  UNL     1       1.729  -2.442  -0.187  1.00  0.00           H  
HETATM   24  H2  UNL     1       2.837   3.425   0.201  1.00  0.00           H  
HETATM   25  H3  UNL     1       6.222  -1.090  -1.043  1.00  0.00           H  
HETATM   26  H4  UNL     1       6.284  -1.238   0.797  1.00  0.00           H  
HETATM   27  H5  UNL     1      -0.930  -0.104   1.720  1.00  0.00           H  
HETATM   28  H6  UNL     1      -3.442   1.565   0.298  1.00  0.00           H  
HETATM   29  H7  UNL     1      -5.699   0.686  -0.055  1.00  0.00           H  
HETATM   30  H8  UNL     1      -6.155  -1.704  -0.125  1.00  0.00           H  
HETATM   31  H9  UNL     1      -4.246  -3.295   0.173  1.00  0.00           H  
HETATM   32  H10 UNL     1      -1.929  -2.408   0.533  1.00  0.00           H  
HETATM   33  H11 UNL     1      -1.599   2.064  -0.311  1.00  0.00           H  
HETATM   34  H12 UNL     1      -0.701   1.921   2.408  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   21
CONECT    3    4    4    8
CONECT    4    5   13
CONECT    5    6    6   23
CONECT    6    7   12
CONECT    7    8    8   10
CONECT    8    9
CONECT    9   24
CONECT   10   11
CONECT   11   12   25   26
CONECT   13   14
CONECT   14   15   21   27
CONECT   15   16   16   20
CONECT   16   17   28
CONECT   17   18   18   29
CONECT   18   19   30
CONECT   19   20   20   31
CONECT   20   32
CONECT   21   22   33
CONECT   22   34
END

HMDB0033321
     RDKit          3D
3,5-Dihydroxy-6,7-methylenedioxyflavanone
 34 37  0  0  0  0  0  0  0  0999 V2000
    0.7070    3.0605   -0.3127 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4380    1.9020    0.0362 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4962    0.9011    0.0068 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0892   -0.4225   -0.0828 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0267   -1.4266   -0.1183 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3554   -1.0773   -0.0626 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7586    0.2354    0.0266 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8203    1.2699    0.0640 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2434    2.5517    0.1531 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1470    0.3051    0.0673 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6565   -1.0108   -0.0813 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5239   -1.8432   -0.0779 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2753   -0.6512   -0.1329 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1812    0.1291    0.6424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5499   -0.3528    0.4350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6093    0.4991    0.2699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8928   -0.0254    0.0707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1380   -1.3804    0.0334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0560   -2.2158    0.2021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7746   -1.7325    0.4010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9687    1.5896    0.4713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1865    2.3161    1.6419 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7286   -2.4417   -0.1868 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8371    3.4250    0.2007 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2222   -1.0902   -1.0431 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2842   -1.2378    0.7965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9302   -0.1042    1.7196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4419    1.5647    0.2985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6995    0.6859   -0.0551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1546   -1.7044   -0.1245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2460   -3.2951    0.1733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9294   -2.4083    0.5328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5990    2.0640   -0.3110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7013    1.9210    2.4083 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
  8  9  1  0
  7 10  1  0
 10 11  1  0
 11 12  1  0
  4 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 14 21  1  0
 21 22  1  0
 21  2  1  0
  8  3  1  0
 20 15  1  0
 12  6  1  0
  5 23  1  0
  9 24  1  0
 11 25  1  0
 11 26  1  0
 14 27  1  0
 16 28  1  0
 17 29  1  0
 18 30  1  0
 19 31  1  0
 20 32  1  0
 21 33  1  0
 22 34  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₆H₁₂O₆

Average Molecular Weight

300.2629

Monoisotopic Molecular Weight

300.063388116

IUPAC Name

2,12-dihydroxy-11-phenyl-4,6,10-trioxatricyclo[7.4.0.0³,⁷]trideca-1,3(7),8-trien-13-one

Traditional Name

2,12-dihydroxy-11-phenyl-4,6,10-trioxatricyclo[7.4.0.0³,⁷]trideca-1,3(7),8-trien-13-one

CAS Registry Number

110204-44-9

SMILES

OC1C(OC2=CC3=C(OCO3)C(O)=C2C1=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C16H12O6/c17-12-11-9(6-10-16(13(11)18)21-7-20-10)22-15(14(12)19)8-4-2-1-3-5-8/h1-6,14-15,18-19H,7H2

InChI Key

WVADKXWSLHLDCL-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavanonols. Flavanonols are compounds containing a flavan-3-one moiety, with a structure characterized by a 2-phenyl-3,4-dihydro-2H-1-benzopyran bearing a hydroxyl group and a ketone at the carbon C2 and C3, respectively.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavans

Direct Parent

Flavanonols

Alternative Parents

Substituents

3-hydroxyflavonoid
5-hydroxyflavonoid
Flavanonol
Hydroxyflavonoid
Chromone
Chromane
1-benzopyran
Benzopyran
Benzodioxole
Aryl alkyl ketone
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Vinylogous acid
Secondary alcohol
Ketone
Ether
Organoheterocyclic compound
Oxacycle
Acetal
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Alcohol
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0033321)
Cytoplasm (HMDB: HMDB0033321)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033321)

Source

Exogenous

Exogenous (HMDB: HMDB0033321)

Food

Food (HMDB: HMDB0033321)

Vegetable

Leaf vegetable

Common beet (FooDB: FOOD00025)

Endogenous

Plant

Plant (HMDB: HMDB0033321)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0033321)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	179 - 180 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.41 g/L	ALOGPS
logP	1.51	ALOGPS
logP	2.35	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	10.17	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	85.22 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	74.43 m³·mol⁻¹	ChemAxon
Polarizability	29.55 Å³	ChemAxon
Number of Rings	4	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]+	167.078	31661259
DarkChem	[M-H]-	166.319	31661259
DeepCCS	[M+H]+	164.767	30932474
DeepCCS	[M-H]-	162.409	30932474
DeepCCS	[M-2H]-	195.682	30932474
DeepCCS	[M+Na]+	170.909	30932474
AllCCS	[M+H]+	170.0	32859911
AllCCS	[M+H-H2O]+	166.3	32859911
AllCCS	[M+NH4]+	173.4	32859911
AllCCS	[M+Na]+	174.4	32859911
AllCCS	[M-H]-	170.6	32859911
AllCCS	[M+Na-2H]-	169.8	32859911
AllCCS	[M+HCOO]-	169.1	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.	6.99 minutes	32390414
Predicted by Siyang on May 30, 2022	13.9599 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.78 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2452.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	372.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	160.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	202.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	129.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	572.0 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	762.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	104.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1170.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	481.5 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	1603.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	392.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	431.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	461.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	210.4 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	97.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3,5-Dihydroxy-6,7-methylenedioxyflavanone	OC1C(OC2=CC3=C(OCO3)C(O)=C2C1=O)C1=CC=CC=C1	3841.7	Standard polar	33892256
3,5-Dihydroxy-6,7-methylenedioxyflavanone	OC1C(OC2=CC3=C(OCO3)C(O)=C2C1=O)C1=CC=CC=C1	2611.7	Standard non polar	33892256
3,5-Dihydroxy-6,7-methylenedioxyflavanone	OC1C(OC2=CC3=C(OCO3)C(O)=C2C1=O)C1=CC=CC=C1	2712.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3,5-Dihydroxy-6,7-methylenedioxyflavanone,1TMS,isomer #1	C[Si](C)(C)OC1C(=O)C2=C(C=C3OCOC3=C2O)OC1C1=CC=CC=C1	2718.5	Semi standard non polar	33892256
3,5-Dihydroxy-6,7-methylenedioxyflavanone,1TMS,isomer #2	C[Si](C)(C)OC1=C2OCOC2=CC2=C1C(=O)C(O)C(C1=CC=CC=C1)O2	2828.8	Semi standard non polar	33892256
3,5-Dihydroxy-6,7-methylenedioxyflavanone,2TMS,isomer #1	C[Si](C)(C)OC1=C2OCOC2=CC2=C1C(=O)C(O[Si](C)(C)C)C(C1=CC=CC=C1)O2	2774.6	Semi standard non polar	33892256
3,5-Dihydroxy-6,7-methylenedioxyflavanone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1C(=O)C2=C(C=C3OCOC3=C2O)OC1C1=CC=CC=C1	2945.1	Semi standard non polar	33892256
3,5-Dihydroxy-6,7-methylenedioxyflavanone,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=C2OCOC2=CC2=C1C(=O)C(O)C(C1=CC=CC=C1)O2	3038.4	Semi standard non polar	33892256
3,5-Dihydroxy-6,7-methylenedioxyflavanone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=C2OCOC2=CC2=C1C(=O)C(O[Si](C)(C)C(C)(C)C)C(C1=CC=CC=C1)O2	3158.3	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 - 3,5-Dihydroxy-6,7-methylenedioxyflavanone GC-MS (Non-derivatized) - 70eV, Positive	splash10-008c-6690000000-e264729ef491d7e3c54b	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,5-Dihydroxy-6,7-methylenedioxyflavanone GC-MS (2 TMS) - 70eV, Positive	splash10-05i3-9313400000-5178a7b0eb136fff4fe0	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,5-Dihydroxy-6,7-methylenedioxyflavanone 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 - 3,5-Dihydroxy-6,7-methylenedioxyflavanone 10V, Positive-QTOF	splash10-0udi-0129000000-45cd759ac045816f55c6	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Dihydroxy-6,7-methylenedioxyflavanone 20V, Positive-QTOF	splash10-0kai-2944000000-9521f1d929f64b214fe3	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Dihydroxy-6,7-methylenedioxyflavanone 40V, Positive-QTOF	splash10-0a4l-3910000000-d33c5c3e59b5afadb7e2	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Dihydroxy-6,7-methylenedioxyflavanone 10V, Negative-QTOF	splash10-0002-0290000000-339c9ce19ef8f36cdce5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Dihydroxy-6,7-methylenedioxyflavanone 20V, Negative-QTOF	splash10-002b-1890000000-1d16cc6df7b973658ded	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Dihydroxy-6,7-methylenedioxyflavanone 40V, Negative-QTOF	splash10-00p0-7910000000-c3970fe1d987a2a7dcd3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Dihydroxy-6,7-methylenedioxyflavanone 10V, Negative-QTOF	splash10-0002-0090000000-4c1c90905db4158d597c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Dihydroxy-6,7-methylenedioxyflavanone 20V, Negative-QTOF	splash10-002b-0980000000-5644b9a9e2f1d817957c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Dihydroxy-6,7-methylenedioxyflavanone 40V, Negative-QTOF	splash10-014i-0900000000-227b45a1ef3493fd0d31	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Dihydroxy-6,7-methylenedioxyflavanone 10V, Positive-QTOF	splash10-0udi-0009000000-545fc7c692e0abcd7966	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Dihydroxy-6,7-methylenedioxyflavanone 20V, Positive-QTOF	splash10-0f8a-0904000000-bbb46d174b4a7a4c264d	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Dihydroxy-6,7-methylenedioxyflavanone 40V, Positive-QTOF	splash10-001i-0900000000-4b7035ca859aa2c74a7a	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

FDB011348

KNApSAcK ID

C00008598

Chemspider ID

35013587

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

76390859

PDB ID

Not Available

ChEBI ID

174858

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

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.. .

Enzymes

Enzyme Details

1. Sulfotransferase family cytosolic 2B member 1

General function:: Involved in sulfotransferase activity
Specific function:: Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of many hormones, neurotransmitters, drugs and xenobiotic compounds. Sulfonation increases the water solubility of most compounds, and therefore their renal excretion, but it can also result in bioactivation to form active metabolites. Sulfates hydroxysteroids like DHEA. Isoform 1 preferentially sulfonates cholesterol, and isoform 2 avidly sulfonates pregnenolone but not cholesterol.
Gene Name:: SULT2B1
Uniprot ID:: O00204
Molecular weight:: 39598.595

Reactions

3,5-Dihydroxy-6,7-methylenedioxyflavanone → {2-hydroxy-13-oxo-11-phenyl-4,6,10-trioxatricyclo[7.4.0.0³,⁷]trideca-1,3(7),8-trien-12-yl}oxidanesulfonic acid	details

Enzyme Details

2. UDP-glucuronosyltransferase 1-1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:: UGT1A1
Uniprot ID:: P22309
Molecular weight:: 59590.91

Reactions

3,5-Dihydroxy-6,7-methylenedioxyflavanone → 3,4,5-trihydroxy-6-({12-hydroxy-13-oxo-11-phenyl-4,6,10-trioxatricyclo[7.4.0.0³,⁷]trideca-1,3(7),8-trien-2-yl}oxy)oxane-2-carboxylic acid	details

Showing metabocard for 3,5-Dihydroxy-6,7-methylenedioxyflavanone (HMDB0033321)

MOL for HMDB0033321 (3,5-Dihydroxy-6,7-methylenedioxyflavanone)

3D MOL for HMDB0033321 (3,5-Dihydroxy-6,7-methylenedioxyflavanone)

3D SDF for HMDB0033321 (3,5-Dihydroxy-6,7-methylenedioxyflavanone)

3D-SDF for HMDB0033321 (3,5-Dihydroxy-6,7-methylenedioxyflavanone)

PDB for HMDB0033321 (3,5-Dihydroxy-6,7-methylenedioxyflavanone)

3D PDB for HMDB0033321 (3,5-Dihydroxy-6,7-methylenedioxyflavanone)

SMILES for HMDB0033321 (3,5-Dihydroxy-6,7-methylenedioxyflavanone)

INCHI for HMDB0033321 (3,5-Dihydroxy-6,7-methylenedioxyflavanone)

Structure for HMDB0033321 (3,5-Dihydroxy-6,7-methylenedioxyflavanone)

3D Structure for HMDB0033321 (3,5-Dihydroxy-6,7-methylenedioxyflavanone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

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