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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 22:44:27 UTC

Update Date

2022-03-07 02:55:21 UTC

HMDB ID

HMDB0037489

Secondary Accession Numbers

HMDB37489

Metabolite Identification

Common Name

Dihydrowogonin

Description

Dihydrowogonin belongs to the class of organic compounds known as 8-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C8 atom of the flavonoid backbone. Thus, dihydrowogonin is considered to be a flavonoid. Dihydrowogonin has been detected, but not quantified in, a few different foods, such as fruits, sour cherries (Prunus cerasus), and sweet cherries (Prunus avium). This could make dihydrowogonin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Dihydrowogonin.

Structure

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

HMDB0037489
     RDKit          3D
Dihydrowogonin
 35 37  0  0  0  0  0  0  0  0999 V2000
   -2.1264    2.8139    0.3540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1716    1.9186   -0.7292 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3583    0.5531   -0.6085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6422   -0.0016   -0.6244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7511    0.8024   -0.7614 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8099   -1.3545   -0.5036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6903   -2.1969   -0.3626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9049   -3.5473   -0.2418 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4348   -1.6498   -0.3483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2620   -0.2673   -0.4709 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0500    0.1751   -0.4413 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0187   -0.3955    0.4410 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3023    0.2767    0.1252 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3091    1.6525   -0.0988 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4608    2.3510   -0.3922 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6642    1.6834   -0.4725 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6779    0.3173   -0.2532 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5002   -0.3641    0.0417 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0651   -1.8822    0.3354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2141   -2.4242   -0.2299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2243   -3.6037   -0.6187 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0019    3.4678    0.3094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9707    2.3301    1.3291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2262    3.4733    0.1979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6691    0.4108   -0.7733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7796   -1.8251   -0.5105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2135   -4.2261   -0.1212 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6978   -0.0939    1.4739 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3790    2.2056   -0.0428 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4702    3.4245   -0.5676 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5777    2.2177   -0.7021 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6314   -0.1954   -0.3193 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5897   -1.4135    0.2014 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1923   -2.3510    1.3324 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8646   -2.2820   -0.3255 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 12 19  1  0
 19 20  1  0
 20 21  2  0
 10  3  1  0
 18 13  1  0
 20  9  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  5 25  1  0
  6 26  1  0
  8 27  1  0
 12 28  1  0
 14 29  1  0
 15 30  1  0
 16 31  1  0
 17 32  1  0
 18 33  1  0
 19 34  1  0
 19 35  1  0
M  END


  Mrv0541 05061309482D          

 21 23  0  0  0  0            999 V2000
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    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
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    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    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    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   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  2  0  0  0  0
  9  5  2  0  0  0  0
  9  6  1  0  0  0  0
 10  7  2  0  0  0  0
 11  8  1  0  0  0  0
 12  7  1  0  0  0  0
 13  8  1  0  0  0  0
 13  9  1  0  0  0  0
 14 10  1  0  0  0  0
 14 11  1  0  0  0  0
 15 12  2  0  0  0  0
 16 14  2  0  0  0  0
 16 15  1  0  0  0  0
 17 10  1  0  0  0  0
 18 11  2  0  0  0  0
 19 12  1  0  0  0  0
 20  1  1  0  0  0  0
 20 15  1  0  0  0  0
 21 13  1  0  0  0  0
 21 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0037489

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(O)C=C(O)C2=C1OC(CC2=O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H14O5/c1-20-15-12(19)7-10(17)14-11(18)8-13(21-16(14)15)9-5-3-2-4-6-9/h2-7,13,17,19H,8H2,1H3

> <INCHI_KEY>
FKAOWOSRYSMEBS-UHFFFAOYSA-N

> <FORMULA>
C16H14O5

> <MOLECULAR_WEIGHT>
286.2794

> <EXACT_MASS>
286.084123558

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
29.053199656202132

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.97

> <JCHEM_LOGP>
2.9810021063333334

> <ALOGPS_LOGS>
-3.36

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.15839470384994

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.440254656679542

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7865066842901447

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
75.77210000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.24e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
dihydrowogonin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0037489
     RDKit          3D
Dihydrowogonin
 35 37  0  0  0  0  0  0  0  0999 V2000
   -2.1264    2.8139    0.3540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1716    1.9186   -0.7292 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3583    0.5531   -0.6085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6422   -0.0016   -0.6244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7511    0.8024   -0.7614 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8099   -1.3545   -0.5036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6903   -2.1969   -0.3626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9049   -3.5473   -0.2418 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4348   -1.6498   -0.3483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2620   -0.2673   -0.4709 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0500    0.1751   -0.4413 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0187   -0.3955    0.4410 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3023    0.2767    0.1252 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3091    1.6525   -0.0988 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4608    2.3510   -0.3922 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6642    1.6834   -0.4725 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6779    0.3173   -0.2532 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5002   -0.3641    0.0417 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0651   -1.8822    0.3354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2141   -2.4242   -0.2299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2243   -3.6037   -0.6187 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0019    3.4678    0.3094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9707    2.3301    1.3291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2262    3.4733    0.1979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6691    0.4108   -0.7733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7796   -1.8251   -0.5105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2135   -4.2261   -0.1212 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6978   -0.0939    1.4739 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3790    2.2056   -0.0428 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4702    3.4245   -0.5676 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5777    2.2177   -0.7021 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6314   -0.1954   -0.3193 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5897   -1.4135    0.2014 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1923   -2.3510    1.3324 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8646   -2.2820   -0.3255 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 12 19  1  0
 19 20  1  0
 20 21  2  0
 10  3  1  0
 18 13  1  0
 20  9  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  5 25  1  0
  6 26  1  0
  8 27  1  0
 12 28  1  0
 14 29  1  0
 15 30  1  0
 16 31  1  0
 17 32  1  0
 18 33  1  0
 19 34  1  0
 19 35  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       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
CONECT    1   20                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3    9                                                       
CONECT    6    4    9                                                       
CONECT    7   10   12                                                       
CONECT    8   11   13                                                       
CONECT    9    5    6   13                                                  
CONECT   10    7   14   17                                                  
CONECT   11    8   14   18                                                  
CONECT   12    7   15   19                                                  
CONECT   13    8    9   21                                                  
CONECT   14   10   11   16                                                  
CONECT   15   12   16   20                                                  
CONECT   16   14   15   21                                                  
CONECT   17   10                                                            
CONECT   18   11                                                            
CONECT   19   12                                                            
CONECT   20    1   15                                                       
CONECT   21   13   16                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    HMDB0037489
HETATM    1  C1  UNL     1      -2.126   2.814   0.354  1.00  0.00           C  
HETATM    2  O1  UNL     1      -2.172   1.919  -0.729  1.00  0.00           O  
HETATM    3  C2  UNL     1      -2.358   0.553  -0.608  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.642  -0.002  -0.624  1.00  0.00           C  
HETATM    5  O2  UNL     1      -4.751   0.802  -0.761  1.00  0.00           O  
HETATM    6  C4  UNL     1      -3.810  -1.355  -0.504  1.00  0.00           C  
HETATM    7  C5  UNL     1      -2.690  -2.197  -0.363  1.00  0.00           C  
HETATM    8  O3  UNL     1      -2.905  -3.547  -0.242  1.00  0.00           O  
HETATM    9  C6  UNL     1      -1.435  -1.650  -0.348  1.00  0.00           C  
HETATM   10  C7  UNL     1      -1.262  -0.267  -0.471  1.00  0.00           C  
HETATM   11  O4  UNL     1       0.050   0.175  -0.441  1.00  0.00           O  
HETATM   12  C8  UNL     1       1.019  -0.395   0.441  1.00  0.00           C  
HETATM   13  C9  UNL     1       2.302   0.277   0.125  1.00  0.00           C  
HETATM   14  C10 UNL     1       2.309   1.652  -0.099  1.00  0.00           C  
HETATM   15  C11 UNL     1       3.461   2.351  -0.392  1.00  0.00           C  
HETATM   16  C12 UNL     1       4.664   1.683  -0.472  1.00  0.00           C  
HETATM   17  C13 UNL     1       4.678   0.317  -0.253  1.00  0.00           C  
HETATM   18  C14 UNL     1       3.500  -0.364   0.042  1.00  0.00           C  
HETATM   19  C15 UNL     1       1.065  -1.882   0.335  1.00  0.00           C  
HETATM   20  C16 UNL     1      -0.214  -2.424  -0.230  1.00  0.00           C  
HETATM   21  O5  UNL     1      -0.224  -3.604  -0.619  1.00  0.00           O  
HETATM   22  H1  UNL     1      -3.002   3.468   0.309  1.00  0.00           H  
HETATM   23  H2  UNL     1      -1.971   2.330   1.329  1.00  0.00           H  
HETATM   24  H3  UNL     1      -1.226   3.473   0.198  1.00  0.00           H  
HETATM   25  H4  UNL     1      -5.669   0.411  -0.773  1.00  0.00           H  
HETATM   26  H5  UNL     1      -4.780  -1.825  -0.510  1.00  0.00           H  
HETATM   27  H6  UNL     1      -2.214  -4.226  -0.121  1.00  0.00           H  
HETATM   28  H7  UNL     1       0.698  -0.094   1.474  1.00  0.00           H  
HETATM   29  H8  UNL     1       1.379   2.206  -0.043  1.00  0.00           H  
HETATM   30  H9  UNL     1       3.470   3.424  -0.568  1.00  0.00           H  
HETATM   31  H10 UNL     1       5.578   2.218  -0.702  1.00  0.00           H  
HETATM   32  H11 UNL     1       5.631  -0.195  -0.319  1.00  0.00           H  
HETATM   33  H12 UNL     1       3.590  -1.413   0.201  1.00  0.00           H  
HETATM   34  H13 UNL     1       1.192  -2.351   1.332  1.00  0.00           H  
HETATM   35  H14 UNL     1       1.865  -2.282  -0.325  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3
CONECT    3    4    4   10
CONECT    4    5    6
CONECT    5   25
CONECT    6    7    7   26
CONECT    7    8    9
CONECT    8   27
CONECT    9   10   10   20
CONECT   10   11
CONECT   11   12
CONECT   12   13   19   28
CONECT   13   14   14   18
CONECT   14   15   29
CONECT   15   16   16   30
CONECT   16   17   31
CONECT   17   18   18   32
CONECT   18   33
CONECT   19   20   34   35
CONECT   20   21   21
END

HMDB0037489
     RDKit          3D
Dihydrowogonin
 35 37  0  0  0  0  0  0  0  0999 V2000
   -2.1264    2.8139    0.3540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1716    1.9186   -0.7292 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3583    0.5531   -0.6085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6422   -0.0016   -0.6244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7511    0.8024   -0.7614 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8099   -1.3545   -0.5036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6903   -2.1969   -0.3626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9049   -3.5473   -0.2418 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4348   -1.6498   -0.3483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2620   -0.2673   -0.4709 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0500    0.1751   -0.4413 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0187   -0.3955    0.4410 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3023    0.2767    0.1252 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3091    1.6525   -0.0988 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4608    2.3510   -0.3922 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6642    1.6834   -0.4725 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6779    0.3173   -0.2532 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5002   -0.3641    0.0417 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0651   -1.8822    0.3354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2141   -2.4242   -0.2299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2243   -3.6037   -0.6187 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0019    3.4678    0.3094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9707    2.3301    1.3291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2262    3.4733    0.1979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6691    0.4108   -0.7733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7796   -1.8251   -0.5105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2135   -4.2261   -0.1212 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6978   -0.0939    1.4739 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3790    2.2056   -0.0428 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4702    3.4245   -0.5676 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5777    2.2177   -0.7021 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6314   -0.1954   -0.3193 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5897   -1.4135    0.2014 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1923   -2.3510    1.3324 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8646   -2.2820   -0.3255 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 12 19  1  0
 19 20  1  0
 20 21  2  0
 10  3  1  0
 18 13  1  0
 20  9  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  5 25  1  0
  6 26  1  0
  8 27  1  0
 12 28  1  0
 14 29  1  0
 15 30  1  0
 16 31  1  0
 17 32  1  0
 18 33  1  0
 19 34  1  0
 19 35  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
5,7-Dihydroxy-8-methoxyflavanone	HMDB

Chemical Formula

C₁₆H₁₄O₅

Average Molecular Weight

286.2794

Monoisotopic Molecular Weight

286.084123558

IUPAC Name

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

Traditional Name

dihydrowogonin

CAS Registry Number

4431-41-8

SMILES

COC1=C(O)C=C(O)C2=C1OC(CC2=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C16H14O5/c1-20-15-12(19)7-10(17)14-11(18)8-13(21-16(14)15)9-5-3-2-4-6-9/h2-7,13,17,19H,8H2,1H3

InChI Key

FKAOWOSRYSMEBS-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 8-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C8 atom of the flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

O-methylated flavonoids

Direct Parent

8-O-methylated flavonoids

Alternative Parents

Substituents

8-methoxyflavonoid-skeleton
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavanone
Hydroxyflavonoid
Flavan
Chromone
Chromane
Benzopyran
1-benzopyran
Anisole
Aryl alkyl ketone
Aryl ketone
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Vinylogous acid
Ketone
Ether
Organoheterocyclic compound
Oxacycle
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Flavanones (LMPK12140661 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0037489)

Cellular substructure

Membrane (HMDB: HMDB0037489)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0037489)

Source

Exogenous

Food

Food (HMDB: HMDB0037489)

Fruit

Drupe

Sour cherry (FooDB: FOOD00146)
Sweet cherry (FooDB: FOOD00145)

Fruits (FooDB: FOOD00871)

Endogenous

Plant

Plant (HMDB: HMDB0037489)

Not Available

Nutrient (HMDB: HMDB0037489)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	150 °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	0.12 g/L	ALOGPS
logP	2.97	ALOGPS
logP	2.98	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	8.44	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	75.77 m³·mol⁻¹	ChemAxon
Polarizability	29.05 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]+	166.351	31661259
DarkChem	[M-H]-	165.332	31661259
DeepCCS	[M+H]+	166.268	30932474
DeepCCS	[M-H]-	163.91	30932474
DeepCCS	[M-2H]-	196.796	30932474
DeepCCS	[M+Na]+	172.362	30932474
AllCCS	[M+H]+	166.4	32859911
AllCCS	[M+H-H2O]+	162.6	32859911
AllCCS	[M+NH4]+	169.9	32859911
AllCCS	[M+Na]+	170.9	32859911
AllCCS	[M-H]-	167.7	32859911
AllCCS	[M+Na-2H]-	167.1	32859911
AllCCS	[M+HCOO]-	166.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dihydrowogonin	COC1=C(O)C=C(O)C2=C1OC(CC2=O)C1=CC=CC=C1	3652.6	Standard polar	33892256
Dihydrowogonin	COC1=C(O)C=C(O)C2=C1OC(CC2=O)C1=CC=CC=C1	2647.5	Standard non polar	33892256
Dihydrowogonin	COC1=C(O)C=C(O)C2=C1OC(CC2=O)C1=CC=CC=C1	2492.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Dihydrowogonin,1TMS,isomer #1	COC1=C(O[Si](C)(C)C)C=C(O)C2=C1OC(C1=CC=CC=C1)CC2=O	2612.5	Semi standard non polar	33892256
Dihydrowogonin,1TMS,isomer #2	COC1=C(O)C=C(O[Si](C)(C)C)C2=C1OC(C1=CC=CC=C1)CC2=O	2634.6	Semi standard non polar	33892256
Dihydrowogonin,2TMS,isomer #1	COC1=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C2=C1OC(C1=CC=CC=C1)CC2=O	2621.1	Semi standard non polar	33892256
Dihydrowogonin,1TBDMS,isomer #1	COC1=C(O[Si](C)(C)C(C)(C)C)C=C(O)C2=C1OC(C1=CC=CC=C1)CC2=O	2858.2	Semi standard non polar	33892256
Dihydrowogonin,1TBDMS,isomer #2	COC1=C(O)C=C(O[Si](C)(C)C(C)(C)C)C2=C1OC(C1=CC=CC=C1)CC2=O	2864.3	Semi standard non polar	33892256
Dihydrowogonin,2TBDMS,isomer #1	COC1=C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)C2=C1OC(C1=CC=CC=C1)CC2=O	3027.4	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 - Dihydrowogonin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0avu-2590000000-3196a48173cc3f04f72d	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydrowogonin GC-MS (2 TMS) - 70eV, Positive	splash10-066r-7719600000-262a1777837ffec50f53	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydrowogonin 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 - Dihydrowogonin 10V, Positive-QTOF	splash10-000i-0290000000-97a632c2bfd7aaa3f9f4	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrowogonin 20V, Positive-QTOF	splash10-00li-0980000000-dc3e52c7c1a7b32b0a07	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrowogonin 40V, Positive-QTOF	splash10-0pb9-2900000000-f641c18c3d2f62a6a7c9	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrowogonin 10V, Negative-QTOF	splash10-000i-0090000000-34d2aa7f5ca2ad6e885d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrowogonin 20V, Negative-QTOF	splash10-000i-0390000000-50bdabf2a71e1702bf36	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrowogonin 40V, Negative-QTOF	splash10-0g29-4920000000-c3d58830e7d687f94b00	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrowogonin 10V, Positive-QTOF	splash10-000i-0090000000-b239d41c6032c85540b2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrowogonin 20V, Positive-QTOF	splash10-001s-0940000000-7563f3723518f1ad8ed8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrowogonin 40V, Positive-QTOF	splash10-001i-0900000000-2a0036a60b62e0e12382	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrowogonin 10V, Negative-QTOF	splash10-000i-0090000000-72ed1dce05f182779977	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrowogonin 20V, Negative-QTOF	splash10-0019-0980000000-4752126b11a7fac030d8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrowogonin 40V, Negative-QTOF	splash10-0udi-0900000000-0cf97750243d88d2ddc9	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

FDB016560

KNApSAcK ID

C00008156

Chemspider ID

9666238

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11491431

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

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Dihydrowogonin (HMDB0037489)

MOL for HMDB0037489 (Dihydrowogonin)

3D MOL for HMDB0037489 (Dihydrowogonin)

3D SDF for HMDB0037489 (Dihydrowogonin)

3D-SDF for HMDB0037489 (Dihydrowogonin)

PDB for HMDB0037489 (Dihydrowogonin)

3D PDB for HMDB0037489 (Dihydrowogonin)

SMILES for HMDB0037489 (Dihydrowogonin)

INCHI for HMDB0037489 (Dihydrowogonin)

Structure for HMDB0037489 (Dihydrowogonin)

3D Structure for HMDB0037489 (Dihydrowogonin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra