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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 22:33:37 UTC

Update Date

2022-03-07 02:55:16 UTC

HMDB ID

HMDB0037322

Secondary Accession Numbers

HMDB37322

Metabolite Identification

Common Name

Dihydrooroxylin

Description

Dihydrooroxylin belongs to the class of organic compounds known as 6-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C6 atom of the flavonoid backbone. Thus, dihydrooroxylin is considered to be a flavonoid. Dihydrooroxylin has been detected, but not quantified in, fruits. This could make dihydrooroxylin a potential biomarker for the consumption of these foods. Dihydrooroxylin is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a small amount of articles have been published on Dihydrooroxylin.

Structure

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

HMDB0037322
     RDKit          3D
Dihydrooroxylin
 35 37  0  0  0  0  0  0  0  0999 V2000
    5.6376    0.7819    0.1049 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7391   -0.1372    0.6976 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4471   -0.3157    0.3230 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0833   -1.2213   -0.6327 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0339   -2.0286   -1.2902 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7574   -1.3926   -1.0054 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7687   -0.6433   -0.4109 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1216    0.2886    0.5698 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4328    0.4454    0.9249 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7792    1.3576    1.8825 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0269    1.0432    1.1707 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1214    1.3273    2.3758 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1283    1.4261    0.3182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4739    0.3606   -0.6666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8736   -0.0840   -0.4372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9140    0.4309   -1.1841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2210    0.0217   -0.9762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5336   -0.9185   -0.0125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5040   -1.4429    0.7426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2006   -1.0239    0.5236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5754   -0.7282   -0.7006 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2125    1.2786    0.9022 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1236    1.4991   -0.5651 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3161    0.1885   -0.5451 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0166   -1.9575   -1.0696 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4625   -2.1111   -1.7650 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1898    1.9650    2.3721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9235    2.4069   -0.1907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9980    1.6374    0.9839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4450    0.8110   -1.6940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7065    1.1756   -1.9546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0593    0.4096   -1.5486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5609   -1.2306    0.1405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7633   -2.1789    1.4943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3895   -1.4407    1.1224 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
  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  3  1  0
 20 15  1  0
 21  7  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  5 25  1  0
  6 26  1  0
 10 27  1  0
 13 28  1  0
 13 29  1  0
 14 30  1  0
 16 31  1  0
 17 32  1  0
 18 33  1  0
 19 34  1  0
 20 35  1  0
M  END


  Mrv0541 05061309422D          

 21 23  0  0  0  0            999 V2000
    3.5724    2.0625    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   -0.4125    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
   -1.4289    0.0000    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
   -0.7145    2.0625    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
   -1.4289    0.8250    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
    2.1434    1.2375    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
    0.7145    1.2375    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
    1.4289    2.4750    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
    0.0000    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    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  1  0  0  0  0
 11  8  2  0  0  0  0
 12  7  1  0  0  0  0
 12  9  1  0  0  0  0
 13  8  1  0  0  0  0
 14 10  1  0  0  0  0
 14 13  2  0  0  0  0
 15 14  1  0  0  0  0
 16 11  1  0  0  0  0
 16 15  2  0  0  0  0
 17 10  2  0  0  0  0
 18 11  1  0  0  0  0
 19 15  1  0  0  0  0
 20  1  1  0  0  0  0
 20 16  1  0  0  0  0
 21 12  1  0  0  0  0
 21 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0037322

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(O)C2=C(OC(CC2=O)C2=CC=CC=C2)C=C1O

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

> <INCHI_KEY>
QUAPPCXFYKSDSV-UHFFFAOYSA-N

> <FORMULA>
C16H14O5

> <MOLECULAR_WEIGHT>
286.2794

> <EXACT_MASS>
286.084123558

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
29.332426064960266

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.01

> <JCHEM_LOGP>
2.9810021063333334

> <ALOGPS_LOGS>
-3.34

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.158229122649372

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.438706483284868

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0040492825048526

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
75.77210000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.31e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
dihydrooroxylin A

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0037322
     RDKit          3D
Dihydrooroxylin
 35 37  0  0  0  0  0  0  0  0999 V2000
    5.6376    0.7819    0.1049 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7391   -0.1372    0.6976 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4471   -0.3157    0.3230 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0833   -1.2213   -0.6327 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0339   -2.0286   -1.2902 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7574   -1.3926   -1.0054 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7687   -0.6433   -0.4109 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1216    0.2886    0.5698 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4328    0.4454    0.9249 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7792    1.3576    1.8825 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0269    1.0432    1.1707 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1214    1.3273    2.3758 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1283    1.4261    0.3182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4739    0.3606   -0.6666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8736   -0.0840   -0.4372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9140    0.4309   -1.1841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2210    0.0217   -0.9762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5336   -0.9185   -0.0125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5040   -1.4429    0.7426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2006   -1.0239    0.5236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5754   -0.7282   -0.7006 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2125    1.2786    0.9022 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1236    1.4991   -0.5651 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3161    0.1885   -0.5451 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0166   -1.9575   -1.0696 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4625   -2.1111   -1.7650 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1898    1.9650    2.3721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9235    2.4069   -0.1907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9980    1.6374    0.9839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4450    0.8110   -1.6940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7065    1.1756   -1.9546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0593    0.4096   -1.5486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5609   -1.2306    0.1405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7633   -2.1789    1.4943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3895   -1.4407    1.1224 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
  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  3  1  0
 20 15  1  0
 21  7  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  5 25  1  0
  6 26  1  0
 10 27  1  0
 13 28  1  0
 13 29  1  0
 14 30  1  0
 16 31  1  0
 17 32  1  0
 18 33  1  0
 19 34  1  0
 20 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       6.668   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.335   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.000   6.160   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       5.335   4.620   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       0.000   1.540   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   12                                                  
CONECT   10    7   14   17                                                  
CONECT   11    8   16   18                                                  
CONECT   12    7    9   21                                                  
CONECT   13    8   14   21                                                  
CONECT   14   10   13   15                                                  
CONECT   15   14   16   19                                                  
CONECT   16   11   15   20                                                  
CONECT   17   10                                                            
CONECT   18   11                                                            
CONECT   19   15                                                            
CONECT   20    1   16                                                       
CONECT   21   12   13                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    HMDB0037322
HETATM    1  C1  UNL     1       5.638   0.782   0.105  1.00  0.00           C  
HETATM    2  O1  UNL     1       4.739  -0.137   0.698  1.00  0.00           O  
HETATM    3  C2  UNL     1       3.447  -0.316   0.323  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.083  -1.221  -0.633  1.00  0.00           C  
HETATM    5  O2  UNL     1       4.034  -2.029  -1.290  1.00  0.00           O  
HETATM    6  C4  UNL     1       1.757  -1.393  -1.005  1.00  0.00           C  
HETATM    7  C5  UNL     1       0.769  -0.643  -0.411  1.00  0.00           C  
HETATM    8  C6  UNL     1       1.122   0.289   0.570  1.00  0.00           C  
HETATM    9  C7  UNL     1       2.433   0.445   0.925  1.00  0.00           C  
HETATM   10  O3  UNL     1       2.779   1.358   1.883  1.00  0.00           O  
HETATM   11  C8  UNL     1       0.027   1.043   1.171  1.00  0.00           C  
HETATM   12  O4  UNL     1       0.121   1.327   2.376  1.00  0.00           O  
HETATM   13  C9  UNL     1      -1.128   1.426   0.318  1.00  0.00           C  
HETATM   14  C10 UNL     1      -1.474   0.361  -0.667  1.00  0.00           C  
HETATM   15  C11 UNL     1      -2.874  -0.084  -0.437  1.00  0.00           C  
HETATM   16  C12 UNL     1      -3.914   0.431  -1.184  1.00  0.00           C  
HETATM   17  C13 UNL     1      -5.221   0.022  -0.976  1.00  0.00           C  
HETATM   18  C14 UNL     1      -5.534  -0.919  -0.013  1.00  0.00           C  
HETATM   19  C15 UNL     1      -4.504  -1.443   0.743  1.00  0.00           C  
HETATM   20  C16 UNL     1      -3.201  -1.024   0.524  1.00  0.00           C  
HETATM   21  O5  UNL     1      -0.575  -0.728  -0.701  1.00  0.00           O  
HETATM   22  H1  UNL     1       6.212   1.279   0.902  1.00  0.00           H  
HETATM   23  H2  UNL     1       5.124   1.499  -0.565  1.00  0.00           H  
HETATM   24  H3  UNL     1       6.316   0.189  -0.545  1.00  0.00           H  
HETATM   25  H4  UNL     1       5.017  -1.957  -1.070  1.00  0.00           H  
HETATM   26  H5  UNL     1       1.463  -2.111  -1.765  1.00  0.00           H  
HETATM   27  H6  UNL     1       2.190   1.965   2.372  1.00  0.00           H  
HETATM   28  H7  UNL     1      -0.924   2.407  -0.191  1.00  0.00           H  
HETATM   29  H8  UNL     1      -1.998   1.637   0.984  1.00  0.00           H  
HETATM   30  H9  UNL     1      -1.445   0.811  -1.694  1.00  0.00           H  
HETATM   31  H10 UNL     1      -3.707   1.176  -1.955  1.00  0.00           H  
HETATM   32  H11 UNL     1      -6.059   0.410  -1.549  1.00  0.00           H  
HETATM   33  H12 UNL     1      -6.561  -1.231   0.140  1.00  0.00           H  
HETATM   34  H13 UNL     1      -4.763  -2.179   1.494  1.00  0.00           H  
HETATM   35  H14 UNL     1      -2.390  -1.441   1.122  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3
CONECT    3    4    4    9
CONECT    4    5    6
CONECT    5   25
CONECT    6    7    7   26
CONECT    7    8   21
CONECT    8    9    9   11
CONECT    9   10
CONECT   10   27
CONECT   11   12   12   13
CONECT   13   14   28   29
CONECT   14   15   21   30
CONECT   15   16   16   20
CONECT   16   17   31
CONECT   17   18   18   32
CONECT   18   19   33
CONECT   19   20   20   34
CONECT   20   35
END

HMDB0037322
     RDKit          3D
Dihydrooroxylin
 35 37  0  0  0  0  0  0  0  0999 V2000
    5.6376    0.7819    0.1049 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7391   -0.1372    0.6976 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4471   -0.3157    0.3230 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0833   -1.2213   -0.6327 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0339   -2.0286   -1.2902 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7574   -1.3926   -1.0054 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7687   -0.6433   -0.4109 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1216    0.2886    0.5698 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4328    0.4454    0.9249 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7792    1.3576    1.8825 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0269    1.0432    1.1707 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1214    1.3273    2.3758 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1283    1.4261    0.3182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4739    0.3606   -0.6666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8736   -0.0840   -0.4372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9140    0.4309   -1.1841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2210    0.0217   -0.9762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5336   -0.9185   -0.0125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5040   -1.4429    0.7426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2006   -1.0239    0.5236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5754   -0.7282   -0.7006 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2125    1.2786    0.9022 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1236    1.4991   -0.5651 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3161    0.1885   -0.5451 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0166   -1.9575   -1.0696 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4625   -2.1111   -1.7650 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1898    1.9650    2.3721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9235    2.4069   -0.1907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9980    1.6374    0.9839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4450    0.8110   -1.6940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7065    1.1756   -1.9546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0593    0.4096   -1.5486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5609   -1.2306    0.1405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7633   -2.1789    1.4943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3895   -1.4407    1.1224 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
  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  3  1  0
 20 15  1  0
 21  7  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  5 25  1  0
  6 26  1  0
 10 27  1  0
 13 28  1  0
 13 29  1  0
 14 30  1  0
 16 31  1  0
 17 32  1  0
 18 33  1  0
 19 34  1  0
 20 35  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
5,7-Dihydroxy-6-methoxyflavanone	ChEBI
Dihydrooroxylin a	HMDB
Dihydrooroxylin	MeSH

Chemical Formula

C₁₆H₁₄O₅

Average Molecular Weight

286.2794

Monoisotopic Molecular Weight

286.084123558

IUPAC Name

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

Traditional Name

dihydrooroxylin A

CAS Registry Number

18956-18-8

SMILES

COC1=C(O)C2=C(OC(CC2=O)C2=CC=CC=C2)C=C1O

InChI Identifier

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

InChI Key

QUAPPCXFYKSDSV-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 6-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C6 atom of the flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

O-methylated flavonoids

Direct Parent

6-O-methylated flavonoids

Alternative Parents

Substituents

6-methoxyflavonoid-skeleton
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavanone
Hydroxyflavonoid
Flavan
Chromone
Benzopyran
Chromane
1-benzopyran
Anisole
Aryl alkyl ketone
Aryl ketone
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Vinylogous acid
Ketone
Organoheterocyclic compound
Oxacycle
Ether
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

monomethoxyflavanone (CHEBI:67376 )
dihydroxyflavanone (CHEBI:67376 )
Flavanones (LMPK12140611 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	177 °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	0.13 g/L	ALOGPS
logP	3.01	ALOGPS
logP	2.98	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	8.44	ChemAxon
pKa (Strongest Basic)	-3	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	29.33 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]+	164.904	31661259
DarkChem	[M-H]-	164.824	31661259
DeepCCS	[M+H]+	162.384	30932474
DeepCCS	[M-H]-	160.026	30932474
DeepCCS	[M-2H]-	193.217	30932474
DeepCCS	[M+Na]+	168.477	30932474
AllCCS	[M+H]+	167.2	32859911
AllCCS	[M+H-H2O]+	163.5	32859911
AllCCS	[M+NH4]+	170.7	32859911
AllCCS	[M+Na]+	171.7	32859911
AllCCS	[M-H]-	168.4	32859911
AllCCS	[M+Na-2H]-	167.8	32859911
AllCCS	[M+HCOO]-	167.3	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. Predicted by Afia on May 17, 2022.	7.48 minutes	32390414
Predicted by Siyang on May 30, 2022	13.1813 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.38 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2345.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	321.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	169.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	184.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	202.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	630.5 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	675.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	81.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1223.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	463.8 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	1345.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	361.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	462.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	414.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	223.7 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	73.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dihydrooroxylin	COC1=C(O)C2=C(OC(CC2=O)C2=CC=CC=C2)C=C1O	3759.8	Standard polar	33892256
Dihydrooroxylin	COC1=C(O)C2=C(OC(CC2=O)C2=CC=CC=C2)C=C1O	2546.2	Standard non polar	33892256
Dihydrooroxylin	COC1=C(O)C2=C(OC(CC2=O)C2=CC=CC=C2)C=C1O	2515.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Dihydrooroxylin,1TMS,isomer #1	COC1=C(O)C=C2OC(C3=CC=CC=C3)CC(=O)C2=C1O[Si](C)(C)C	2660.0	Semi standard non polar	33892256
Dihydrooroxylin,1TMS,isomer #2	COC1=C(O[Si](C)(C)C)C=C2OC(C3=CC=CC=C3)CC(=O)C2=C1O	2682.0	Semi standard non polar	33892256
Dihydrooroxylin,2TMS,isomer #1	COC1=C(O[Si](C)(C)C)C=C2OC(C3=CC=CC=C3)CC(=O)C2=C1O[Si](C)(C)C	2676.4	Semi standard non polar	33892256
Dihydrooroxylin,1TBDMS,isomer #1	COC1=C(O)C=C2OC(C3=CC=CC=C3)CC(=O)C2=C1O[Si](C)(C)C(C)(C)C	2891.4	Semi standard non polar	33892256
Dihydrooroxylin,1TBDMS,isomer #2	COC1=C(O[Si](C)(C)C(C)(C)C)C=C2OC(C3=CC=CC=C3)CC(=O)C2=C1O	2919.0	Semi standard non polar	33892256
Dihydrooroxylin,2TBDMS,isomer #1	COC1=C(O[Si](C)(C)C(C)(C)C)C=C2OC(C3=CC=CC=C3)CC(=O)C2=C1O[Si](C)(C)C(C)(C)C	3079.1	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydrooroxylin GC-MS (Non-derivatized) - 70eV, Positive	splash10-05g3-3490000000-9ae7565d0700b3592b11	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydrooroxylin GC-MS (2 TMS) - 70eV, Positive	splash10-06dl-5719500000-560d4e9c3212dbf4b3a6	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydrooroxylin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydrooroxylin 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dihydrooroxylin , positive-QTOF	splash10-00m0-0910000000-27c707ca1f3734432a8a	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrooroxylin 10V, Positive-QTOF	splash10-000i-0290000000-9124d61c9b4c9168b54f	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrooroxylin 20V, Positive-QTOF	splash10-00li-0980000000-841336381aecd17caafb	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrooroxylin 40V, Positive-QTOF	splash10-0ldi-2900000000-3b1d097c03b13a1b692e	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrooroxylin 10V, Negative-QTOF	splash10-000i-0090000000-512568fdac86ba822b17	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrooroxylin 20V, Negative-QTOF	splash10-000i-1390000000-7d54008aa89f5de59199	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrooroxylin 40V, Negative-QTOF	splash10-0g6r-5920000000-c8a34f8d8b40c7afaf4e	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrooroxylin 10V, Positive-QTOF	splash10-000i-0090000000-b239d41c6032c85540b2	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrooroxylin 20V, Positive-QTOF	splash10-001s-0940000000-7563f3723518f1ad8ed8	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrooroxylin 40V, Positive-QTOF	splash10-001i-0900000000-2a0036a60b62e0e12382	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrooroxylin 10V, Negative-QTOF	splash10-000i-0090000000-72ed1dce05f182779977	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrooroxylin 20V, Negative-QTOF	splash10-0019-0980000000-4752126b11a7fac030d8	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrooroxylin 40V, Negative-QTOF	splash10-0udi-0900000000-0cf97750243d88d2ddc9	2021-09-25	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

FDB016342

KNApSAcK ID

C00008148

Chemspider ID

4475720

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5316733

PDB ID

Not Available

ChEBI ID

67376

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. 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

Dihydrooroxylin → 3,4,5-trihydroxy-6-[(5-hydroxy-6-methoxy-4-oxo-2-phenyl-3,4-dihydro-2H-1-benzopyran-7-yl)oxy]oxane-2-carboxylic acid	details
Dihydrooroxylin → 3,4,5-trihydroxy-6-[(7-hydroxy-6-methoxy-4-oxo-2-phenyl-3,4-dihydro-2H-1-benzopyran-5-yl)oxy]oxane-2-carboxylic acid	details

Showing metabocard for Dihydrooroxylin (HMDB0037322)

MOL for HMDB0037322 (Dihydrooroxylin)

3D MOL for HMDB0037322 (Dihydrooroxylin)

3D SDF for HMDB0037322 (Dihydrooroxylin)

3D-SDF for HMDB0037322 (Dihydrooroxylin)

PDB for HMDB0037322 (Dihydrooroxylin)

3D PDB for HMDB0037322 (Dihydrooroxylin)

SMILES for HMDB0037322 (Dihydrooroxylin)

INCHI for HMDB0037322 (Dihydrooroxylin)

Structure for HMDB0037322 (Dihydrooroxylin)

3D Structure for HMDB0037322 (Dihydrooroxylin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions