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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:38:28 UTC

Update Date

2022-03-07 02:52:39 UTC

HMDB ID

HMDB0030694

Secondary Accession Numbers

HMDB30694

Metabolite Identification

Common Name

(S)-5,7-Dihydroxy-6,8-dimethylflavanone

Description

(S)-5,7-Dihydroxy-6,8-dimethylflavanone, also known as demethoxymatteucinol, belongs to the class of organic compounds known as flavanones. Flavanones are compounds containing a flavan-3-one moiety, with a structure characterized by a 2-phenyl-3,4-dihydro-2H-1-benzopyran bearing a ketone at the carbon C3. Thus, (S)-5,7-dihydroxy-6,8-dimethylflavanone is considered to be a flavonoid. Based on a literature review a significant number of articles have been published on (S)-5,7-Dihydroxy-6,8-dimethylflavanone.

Structure

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

HMDB0030694
     RDKit          3D
(S)-5,7-Dihydroxy-6,8-dimethylflavanone
 37 39  0  0  0  0  0  0  0  0999 V2000
   -5.0471    0.4595    0.3669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5997    0.1394    0.2349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1283   -1.1451    0.3757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0417   -2.1489    0.6467 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7706   -1.3307    0.2341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2608   -2.7098    0.3841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8938   -0.3169   -0.0339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3895    0.9634   -0.1713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7329    1.2155   -0.0415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2421    2.4728   -0.1726 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4152    2.0112   -0.4656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7986    3.0284   -1.0697 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0114    1.8982   -0.0675 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3714    0.4865    0.3338 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7727    0.1546   -0.0297 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7968    0.2284    0.8915 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1057   -0.0771    0.5690 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4360   -0.4716   -0.7034 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4229   -0.5509   -1.6384 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1043   -0.2417   -1.3078 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4700   -0.4804   -0.1794 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1979    1.4871    0.7606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5428    0.3232   -0.6092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5287   -0.2208    1.1285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8072   -3.1125    0.7672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8080   -3.2521    1.1714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3800   -3.3128   -0.5469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1862   -2.7414    0.6407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8678    3.3480   -0.3488 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6925    2.2276   -0.8920 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1807    2.5866    0.7846 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3184    0.4533    1.4593 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5447    0.5387    1.8973 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9121   -0.0182    1.2971 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4679   -0.7069   -0.9372 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6941   -0.8640   -2.6425 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3371   -0.3204   -2.0858 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  8 11  1  0
 11 12  2  0
 11 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
  9  2  1  0
 20 15  1  0
 21  7  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  6 26  1  0
  6 27  1  0
  6 28  1  0
 10 29  1  0
 13 30  1  0
 13 31  1  0
 14 32  1  0
 16 33  1  0
 17 34  1  0
 18 35  1  0
 19 36  1  0
 20 37  1  0
M  END


  Mrv0541 05061305262D          

 21 23  0  0  0  0            999 V2000
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  2  0  0  0  0
  9  1  1  0  0  0  0
 10  2  1  0  0  0  0
 11  6  2  0  0  0  0
 11  7  1  0  0  0  0
 12  8  1  0  0  0  0
 13  8  1  0  0  0  0
 13 11  1  0  0  0  0
 14 12  1  0  0  0  0
 15  9  2  0  0  0  0
 15 10  1  0  0  0  0
 16  9  1  0  0  0  0
 16 14  2  0  0  0  0
 17 10  2  0  0  0  0
 17 14  1  0  0  0  0
 18 12  2  0  0  0  0
 19 15  1  0  0  0  0
 20 16  1  0  0  0  0
 21 13  1  0  0  0  0
 21 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030694

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=C(O)C(C)=C2OC(CC(=O)C2=C1O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H16O4/c1-9-15(19)10(2)17-14(16(9)20)12(18)8-13(21-17)11-6-4-3-5-7-11/h3-7,13,19-20H,8H2,1-2H3

> <INCHI_KEY>
HAIHGFWQOPJMPV-UHFFFAOYSA-N

> <FORMULA>
C17H16O4

> <MOLECULAR_WEIGHT>
284.3065

> <EXACT_MASS>
284.104859

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
30.396030136513566

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,7-dihydroxy-6,8-dimethyl-2-phenyl-3,4-dihydro-2H-1-benzopyran-4-one

> <ALOGPS_LOGP>
2.96

> <JCHEM_LOGP>
4.165516150666666

> <ALOGPS_LOGS>
-3.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.369630712736651

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.668473234320915

> <JCHEM_PKA_STRONGEST_BASIC>
-3.787688206079326

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
79.3913

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.59e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
desmethoxymatteucinol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030694
     RDKit          3D
(S)-5,7-Dihydroxy-6,8-dimethylflavanone
 37 39  0  0  0  0  0  0  0  0999 V2000
   -5.0471    0.4595    0.3669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5997    0.1394    0.2349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1283   -1.1451    0.3757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0417   -2.1489    0.6467 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7706   -1.3307    0.2341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2608   -2.7098    0.3841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8938   -0.3169   -0.0339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3895    0.9634   -0.1713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7329    1.2155   -0.0415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2421    2.4728   -0.1726 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4152    2.0112   -0.4656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7986    3.0284   -1.0697 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0114    1.8982   -0.0675 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3714    0.4865    0.3338 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7727    0.1546   -0.0297 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7968    0.2284    0.8915 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1057   -0.0771    0.5690 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4360   -0.4716   -0.7034 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4229   -0.5509   -1.6384 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1043   -0.2417   -1.3078 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4700   -0.4804   -0.1794 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1979    1.4871    0.7606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5428    0.3232   -0.6092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5287   -0.2208    1.1285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8072   -3.1125    0.7672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8080   -3.2521    1.1714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3800   -3.3128   -0.5469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1862   -2.7414    0.6407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8678    3.3480   -0.3488 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6925    2.2276   -0.8920 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1807    2.5866    0.7846 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3184    0.4533    1.4593 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5447    0.5387    1.8973 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9121   -0.0182    1.2971 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4679   -0.7069   -0.9372 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6941   -0.8640   -2.6425 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3371   -0.3204   -2.0858 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  8 11  1  0
 11 12  2  0
 11 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
  9  2  1  0
 20 15  1  0
 21  7  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  6 26  1  0
  6 27  1  0
  6 28  1  0
 10 29  1  0
 13 30  1  0
 13 31  1  0
 14 32  1  0
 16 33  1  0
 17 34  1  0
 18 35  1  0
 19 36  1  0
 20 37  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       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       8.002   4.620   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
CONECT    1    9                                                            
CONECT    2   10                                                            
CONECT    3    4    5                                                       
CONECT    4    3    6                                                       
CONECT    5    3    7                                                       
CONECT    6    4   11                                                       
CONECT    7    5   11                                                       
CONECT    8   12   13                                                       
CONECT    9    1   15   16                                                  
CONECT   10    2   15   17                                                  
CONECT   11    6    7   13                                                  
CONECT   12    8   14   18                                                  
CONECT   13    8   11   21                                                  
CONECT   14   12   16   17                                                  
CONECT   15    9   10   19                                                  
CONECT   16    9   14   20                                                  
CONECT   17   10   14   21                                                  
CONECT   18   12                                                            
CONECT   19   15                                                            
CONECT   20   16                                                            
CONECT   21   13   17                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    HMDB0030694
HETATM    1  C1  UNL     1      -5.047   0.460   0.367  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.600   0.139   0.235  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.128  -1.145   0.376  1.00  0.00           C  
HETATM    4  O1  UNL     1      -4.042  -2.149   0.647  1.00  0.00           O  
HETATM    5  C4  UNL     1      -1.771  -1.331   0.234  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.261  -2.710   0.384  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.894  -0.317  -0.034  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.389   0.963  -0.171  1.00  0.00           C  
HETATM    9  C8  UNL     1      -2.733   1.216  -0.042  1.00  0.00           C  
HETATM   10  O2  UNL     1      -3.242   2.473  -0.173  1.00  0.00           O  
HETATM   11  C9  UNL     1      -0.415   2.011  -0.466  1.00  0.00           C  
HETATM   12  O3  UNL     1      -0.799   3.028  -1.070  1.00  0.00           O  
HETATM   13  C10 UNL     1       1.011   1.898  -0.067  1.00  0.00           C  
HETATM   14  C11 UNL     1       1.371   0.486   0.334  1.00  0.00           C  
HETATM   15  C12 UNL     1       2.773   0.155  -0.030  1.00  0.00           C  
HETATM   16  C13 UNL     1       3.797   0.228   0.891  1.00  0.00           C  
HETATM   17  C14 UNL     1       5.106  -0.077   0.569  1.00  0.00           C  
HETATM   18  C15 UNL     1       5.436  -0.472  -0.703  1.00  0.00           C  
HETATM   19  C16 UNL     1       4.423  -0.551  -1.638  1.00  0.00           C  
HETATM   20  C17 UNL     1       3.104  -0.242  -1.308  1.00  0.00           C  
HETATM   21  O4  UNL     1       0.470  -0.480  -0.179  1.00  0.00           O  
HETATM   22  H1  UNL     1      -5.198   1.487   0.761  1.00  0.00           H  
HETATM   23  H2  UNL     1      -5.543   0.323  -0.609  1.00  0.00           H  
HETATM   24  H3  UNL     1      -5.529  -0.221   1.128  1.00  0.00           H  
HETATM   25  H4  UNL     1      -3.807  -3.112   0.767  1.00  0.00           H  
HETATM   26  H5  UNL     1      -1.808  -3.252   1.171  1.00  0.00           H  
HETATM   27  H6  UNL     1      -1.380  -3.313  -0.547  1.00  0.00           H  
HETATM   28  H7  UNL     1      -0.186  -2.741   0.641  1.00  0.00           H  
HETATM   29  H8  UNL     1      -2.868   3.348  -0.349  1.00  0.00           H  
HETATM   30  H9  UNL     1       1.692   2.228  -0.892  1.00  0.00           H  
HETATM   31  H10 UNL     1       1.181   2.587   0.785  1.00  0.00           H  
HETATM   32  H11 UNL     1       1.318   0.453   1.459  1.00  0.00           H  
HETATM   33  H12 UNL     1       3.545   0.539   1.897  1.00  0.00           H  
HETATM   34  H13 UNL     1       5.912  -0.018   1.297  1.00  0.00           H  
HETATM   35  H14 UNL     1       6.468  -0.707  -0.937  1.00  0.00           H  
HETATM   36  H15 UNL     1       4.694  -0.864  -2.643  1.00  0.00           H  
HETATM   37  H16 UNL     1       2.337  -0.320  -2.086  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3    3    9
CONECT    3    4    5
CONECT    4   25
CONECT    5    6    7    7
CONECT    6   26   27   28
CONECT    7    8   21
CONECT    8    9    9   11
CONECT    9   10
CONECT   10   29
CONECT   11   12   12   13
CONECT   13   14   30   31
CONECT   14   15   21   32
CONECT   15   16   16   20
CONECT   16   17   33
CONECT   17   18   18   34
CONECT   18   19   35
CONECT   19   20   20   36
CONECT   20   37
END

HMDB0030694
     RDKit          3D
(S)-5,7-Dihydroxy-6,8-dimethylflavanone
 37 39  0  0  0  0  0  0  0  0999 V2000
   -5.0471    0.4595    0.3669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5997    0.1394    0.2349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1283   -1.1451    0.3757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0417   -2.1489    0.6467 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7706   -1.3307    0.2341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2608   -2.7098    0.3841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8938   -0.3169   -0.0339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3895    0.9634   -0.1713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7329    1.2155   -0.0415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2421    2.4728   -0.1726 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4152    2.0112   -0.4656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7986    3.0284   -1.0697 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0114    1.8982   -0.0675 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3714    0.4865    0.3338 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7727    0.1546   -0.0297 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7968    0.2284    0.8915 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1057   -0.0771    0.5690 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4360   -0.4716   -0.7034 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4229   -0.5509   -1.6384 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1043   -0.2417   -1.3078 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4700   -0.4804   -0.1794 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1979    1.4871    0.7606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5428    0.3232   -0.6092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5287   -0.2208    1.1285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8072   -3.1125    0.7672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8080   -3.2521    1.1714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3800   -3.3128   -0.5469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1862   -2.7414    0.6407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8678    3.3480   -0.3488 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6925    2.2276   -0.8920 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1807    2.5866    0.7846 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3184    0.4533    1.4593 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5447    0.5387    1.8973 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9121   -0.0182    1.2971 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4679   -0.7069   -0.9372 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6941   -0.8640   -2.6425 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3371   -0.3204   -2.0858 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  8 11  1  0
 11 12  2  0
 11 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
  9  2  1  0
 20 15  1  0
 21  7  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  6 26  1  0
  6 27  1  0
  6 28  1  0
 10 29  1  0
 13 30  1  0
 13 31  1  0
 14 32  1  0
 16 33  1  0
 17 34  1  0
 18 35  1  0
 19 36  1  0
 20 37  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(-)-Demethoxymatteucinol	HMDB
Demethoxymatteucinol	HMDB
Desmethoxy-matteucinol	HMDB
Desmethoxymatteucinol	HMDB

Chemical Formula

C₁₇H₁₆O₄

Average Molecular Weight

284.3065

Monoisotopic Molecular Weight

284.104859

IUPAC Name

5,7-dihydroxy-6,8-dimethyl-2-phenyl-3,4-dihydro-2H-1-benzopyran-4-one

Traditional Name

desmethoxymatteucinol

CAS Registry Number

56297-79-1

SMILES

CC1=C(O)C(C)=C2OC(CC(=O)C2=C1O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C17H16O4/c1-9-15(19)10(2)17-14(16(9)20)12(18)8-13(21-17)11-6-4-3-5-7-11/h3-7,13,19-20H,8H2,1-2H3

InChI Key

HAIHGFWQOPJMPV-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavanones. Flavanones are compounds containing a flavan-3-one moiety, with a structure characterized by a 2-phenyl-3,4-dihydro-2H-1-benzopyran bearing a ketone at the carbon C3.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavans

Direct Parent

Flavanones

Alternative Parents

Substituents

5-hydroxyflavonoid
7-hydroxyflavonoid
Flavanone
Hydroxyflavonoid
Chromone
Chromane
Benzopyran
1-benzopyran
Aryl alkyl ketone
Aryl ketone
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Vinylogous acid
Ketone
Ether
Organoheterocyclic compound
Oxacycle
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Flavanones (LMPK12140192 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0030694)
Cell membrane (HMDB: HMDB0030694)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030694)

Source

Endogenous

Endogenous (HMDB: HMDB0030694)

Plant

Plant (HMDB: HMDB0030694)

Exogenous

Food

Food (HMDB: HMDB0030694)

Fruit

Fruits (FooDB: FOOD00871)

Exogenous (HMDB: HMDB0030694)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	202 - 204 °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	0.046 g/L	ALOGPS
logP	2.96	ALOGPS
logP	4.17	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	8.67	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	79.39 m³·mol⁻¹	ChemAxon
Polarizability	30.4 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]+	165.788	31661259
DarkChem	[M-H]-	164.572	31661259
DeepCCS	[M+H]+	166.792	30932474
DeepCCS	[M-H]-	164.434	30932474
DeepCCS	[M-2H]-	197.786	30932474
DeepCCS	[M+Na]+	173.013	30932474
AllCCS	[M+H]+	166.8	32859911
AllCCS	[M+H-H2O]+	163.1	32859911
AllCCS	[M+NH4]+	170.2	32859911
AllCCS	[M+Na]+	171.2	32859911
AllCCS	[M-H]-	169.7	32859911
AllCCS	[M+Na-2H]-	169.1	32859911
AllCCS	[M+HCOO]-	168.5	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.	8.54 minutes	32390414
Predicted by Siyang on May 30, 2022	16.4563 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.61 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2555.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	461.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	208.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	250.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	370.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	806.2 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	955.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	74.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1487.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	555.6 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	1644.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	484.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	523.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	433.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	221.4 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	35.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(S)-5,7-Dihydroxy-6,8-dimethylflavanone	CC1=C(O)C(C)=C2OC(CC(=O)C2=C1O)C1=CC=CC=C1	3836.9	Standard polar	33892256
(S)-5,7-Dihydroxy-6,8-dimethylflavanone	CC1=C(O)C(C)=C2OC(CC(=O)C2=C1O)C1=CC=CC=C1	2622.3	Standard non polar	33892256
(S)-5,7-Dihydroxy-6,8-dimethylflavanone	CC1=C(O)C(C)=C2OC(CC(=O)C2=C1O)C1=CC=CC=C1	2548.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(S)-5,7-Dihydroxy-6,8-dimethylflavanone,1TMS,isomer #1	CC1=C(O)C2=C(OC(C3=CC=CC=C3)CC2=O)C(C)=C1O[Si](C)(C)C	2668.0	Semi standard non polar	33892256
(S)-5,7-Dihydroxy-6,8-dimethylflavanone,1TMS,isomer #2	CC1=C(O)C(C)=C(O[Si](C)(C)C)C2=C1OC(C1=CC=CC=C1)CC2=O	2669.8	Semi standard non polar	33892256
(S)-5,7-Dihydroxy-6,8-dimethylflavanone,2TMS,isomer #1	CC1=C(O[Si](C)(C)C)C(C)=C(O[Si](C)(C)C)C2=C1OC(C1=CC=CC=C1)CC2=O	2691.3	Semi standard non polar	33892256
(S)-5,7-Dihydroxy-6,8-dimethylflavanone,1TBDMS,isomer #1	CC1=C(O)C2=C(OC(C3=CC=CC=C3)CC2=O)C(C)=C1O[Si](C)(C)C(C)(C)C	2891.1	Semi standard non polar	33892256
(S)-5,7-Dihydroxy-6,8-dimethylflavanone,1TBDMS,isomer #2	CC1=C(O)C(C)=C(O[Si](C)(C)C(C)(C)C)C2=C1OC(C1=CC=CC=C1)CC2=O	2888.0	Semi standard non polar	33892256
(S)-5,7-Dihydroxy-6,8-dimethylflavanone,2TBDMS,isomer #1	CC1=C(O[Si](C)(C)C(C)(C)C)C(C)=C(O[Si](C)(C)C(C)(C)C)C2=C1OC(C1=CC=CC=C1)CC2=O	3103.4	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 - (S)-5,7-Dihydroxy-6,8-dimethylflavanone GC-MS (Non-derivatized) - 70eV, Positive	splash10-00lr-2590000000-785e0fbfff2f98942aa3	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (S)-5,7-Dihydroxy-6,8-dimethylflavanone GC-MS (2 TMS) - 70eV, Positive	splash10-0c2c-7928500000-689b4f38ea41c285fdf3	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (S)-5,7-Dihydroxy-6,8-dimethylflavanone 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 - (S)-5,7-Dihydroxy-6,8-dimethylflavanone 10V, Positive-QTOF	splash10-000i-0490000000-99936654c83854287bba	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-5,7-Dihydroxy-6,8-dimethylflavanone 20V, Positive-QTOF	splash10-07wl-2940000000-9d545b0c06effa6d3ddd	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-5,7-Dihydroxy-6,8-dimethylflavanone 40V, Positive-QTOF	splash10-0bt9-2900000000-01951ed411e8fba53c37	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-5,7-Dihydroxy-6,8-dimethylflavanone 10V, Negative-QTOF	splash10-001i-0190000000-aae499b09d9f06d8e104	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-5,7-Dihydroxy-6,8-dimethylflavanone 20V, Negative-QTOF	splash10-001i-1790000000-c3de3e95865363c9d3f5	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-5,7-Dihydroxy-6,8-dimethylflavanone 40V, Negative-QTOF	splash10-004r-6900000000-6aa05df22d78a14450fe	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-5,7-Dihydroxy-6,8-dimethylflavanone 10V, Negative-QTOF	splash10-001i-0090000000-3ffcbf9f9605ea2feb0d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-5,7-Dihydroxy-6,8-dimethylflavanone 20V, Negative-QTOF	splash10-003r-0980000000-3dceb36665bdc42168cc	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-5,7-Dihydroxy-6,8-dimethylflavanone 40V, Negative-QTOF	splash10-0udi-0900000000-4e2d7aeec72c540f9813	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-5,7-Dihydroxy-6,8-dimethylflavanone 10V, Positive-QTOF	splash10-000i-0090000000-73f3d88b664986140f8c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-5,7-Dihydroxy-6,8-dimethylflavanone 20V, Positive-QTOF	splash10-001s-0940000000-fe40b781b7c352a532bd	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-5,7-Dihydroxy-6,8-dimethylflavanone 40V, Positive-QTOF	splash10-001i-0900000000-9c3186ac53707ab6c4e6	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

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

FDB002615

KNApSAcK ID

C00008168

Chemspider ID

542961

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

625031

PDB ID

Not Available

ChEBI ID

Not Available

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

Resurreccion-Magno MH, Villasenor IM, Harada N, Monde K: Antihyperglycaemic flavonoids from Syzygium samarangense (Blume) Merr. and Perry. Phytother Res. 2005 Mar;19(3):246-51. [PubMed:15934025 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Enzymes

Enzyme Details

1. 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

(S)-5,7-Dihydroxy-6,8-dimethylflavanone → 3,4,5-trihydroxy-6-[(7-hydroxy-6,8-dimethyl-4-oxo-2-phenyl-3,4-dihydro-2H-1-benzopyran-5-yl)oxy]oxane-2-carboxylic acid	details
(S)-5,7-Dihydroxy-6,8-dimethylflavanone → 3,4,5-trihydroxy-6-[(5-hydroxy-6,8-dimethyl-4-oxo-2-phenyl-3,4-dihydro-2H-1-benzopyran-7-yl)oxy]oxane-2-carboxylic acid	details

Showing metabocard for (S)-5,7-Dihydroxy-6,8-dimethylflavanone (HMDB0030694)

MOL for HMDB0030694 ((S)-5,7-Dihydroxy-6,8-dimethylflavanone)

3D MOL for HMDB0030694 ((S)-5,7-Dihydroxy-6,8-dimethylflavanone)

3D SDF for HMDB0030694 ((S)-5,7-Dihydroxy-6,8-dimethylflavanone)

3D-SDF for HMDB0030694 ((S)-5,7-Dihydroxy-6,8-dimethylflavanone)

PDB for HMDB0030694 ((S)-5,7-Dihydroxy-6,8-dimethylflavanone)

3D PDB for HMDB0030694 ((S)-5,7-Dihydroxy-6,8-dimethylflavanone)

SMILES for HMDB0030694 ((S)-5,7-Dihydroxy-6,8-dimethylflavanone)

INCHI for HMDB0030694 ((S)-5,7-Dihydroxy-6,8-dimethylflavanone)

Structure for HMDB0030694 ((S)-5,7-Dihydroxy-6,8-dimethylflavanone)

3D Structure for HMDB0030694 ((S)-5,7-Dihydroxy-6,8-dimethylflavanone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions