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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 22:29:34 UTC

Update Date

2022-03-07 02:55:15 UTC

HMDB ID

HMDB0037253

Secondary Accession Numbers

HMDB37253

Metabolite Identification

Common Name

5-Hydroxy-3-(4-hydroxybenzyl)-7,8-dimethoxy-4-chromanone

Description

5-Hydroxy-3-(4-hydroxybenzyl)-7,8-dimethoxy-4-chromanone belongs to the class of organic compounds known as homoisoflavanones. These are homoisoflavonoids with a structure based on the chromanone system. Chromanone is a bicyclic compound consisting of a 3,4-dihydro-1-benzopyran, which bears a ketone group at the 4-position. 5-Hydroxy-3-(4-hydroxybenzyl)-7,8-dimethoxy-4-chromanone has been detected, but not quantified in, herbs and spices. This could make 5-hydroxy-3-(4-hydroxybenzyl)-7,8-dimethoxy-4-chromanone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 5-Hydroxy-3-(4-hydroxybenzyl)-7,8-dimethoxy-4-chromanone.

Structure

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

HMDB0037253
     RDKit          3D
5-Hydroxy-3-(4-hydroxybenzyl)-7,8-dimethoxy-4-chromanone
 42 44  0  0  0  0  0  0  0  0999 V2000
   -5.0819   -1.1427   -2.0652 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6853   -0.3062   -0.9897 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3361   -0.0320   -0.8713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3823   -0.5245   -1.7324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0200   -0.2336   -1.5935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0900   -0.7345   -2.4594 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6743    0.5768   -0.5449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6180    1.0953    0.3506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9441    0.7800    0.1713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8798    1.2728    1.0295 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3286    0.6780    2.2078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1778    1.9062    1.3828 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0601    1.7103    2.0397 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1396    1.2974    1.0997 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7791    0.0314    1.6916 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8499   -0.3859    0.7689 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1237    0.1287    0.9717 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.7173   -1.5819   -1.0754 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.8847    1.4738    2.7832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0543    1.0169    2.9114 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3026    2.6992    2.5152 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.2345    0.2760    2.6637 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9920   -0.7521    1.7899 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2819    0.8184    1.7991 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1862    0.2227    0.3523 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1606   -0.8581   -2.5484 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5466   -2.2792   -1.9081 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6462   -1.6424   -0.4101 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
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M  END


  Mrv0541 05061309402D          

 24 26  0  0  0  0            999 V2000
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    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
    4.2868    4.9500    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    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 23 17  1  0  0  0  0
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 24 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0037253

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(OC)C2=C(C(O)=C1)C(=O)C(CC1=CC=C(O)C=C1)CO2

> <INCHI_IDENTIFIER>
InChI=1S/C18H18O6/c1-22-14-8-13(20)15-16(21)11(9-24-18(15)17(14)23-2)7-10-3-5-12(19)6-4-10/h3-6,8,11,19-20H,7,9H2,1-2H3

> <INCHI_KEY>
GMCVGMAGOGOINY-UHFFFAOYSA-N

> <FORMULA>
C18H18O6

> <MOLECULAR_WEIGHT>
330.3319

> <EXACT_MASS>
330.110338308

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
33.383963195101934

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-hydroxy-3-[(4-hydroxyphenyl)methyl]-7,8-dimethoxy-3,4-dihydro-2H-1-benzopyran-4-one

> <ALOGPS_LOGP>
2.77

> <JCHEM_LOGP>
3.1604495693333323

> <ALOGPS_LOGS>
-3.87

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.440287599950937

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.45141836369876

> <JCHEM_PKA_STRONGEST_BASIC>
-3.8388979820678246

> <JCHEM_POLAR_SURFACE_AREA>
85.22000000000001

> <JCHEM_REFRACTIVITY>
87.223

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.51e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-hydroxy-3-[(4-hydroxyphenyl)methyl]-7,8-dimethoxy-2,3-dihydro-1-benzopyran-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0037253
     RDKit          3D
5-Hydroxy-3-(4-hydroxybenzyl)-7,8-dimethoxy-4-chromanone
 42 44  0  0  0  0  0  0  0  0999 V2000
   -5.0819   -1.1427   -2.0652 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6853   -0.3062   -0.9897 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3361   -0.0320   -0.8713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3823   -0.5245   -1.7324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0200   -0.2336   -1.5935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0900   -0.7345   -2.4594 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6743    0.5768   -0.5449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6180    1.0953    0.3506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9441    0.7800    0.1713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8798    1.2728    1.0295 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3286    0.6780    2.2078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1778    1.9062    1.3828 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0601    1.7103    2.0397 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1396    1.2974    1.0997 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7791    0.0314    1.6916 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8499   -0.3859    0.7689 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1237    0.1287    0.9717 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1950   -0.1892    0.1799 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9804   -1.0654   -0.8663 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0220   -1.4417   -1.7224 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7173   -1.5819   -1.0754 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6500   -1.2645   -0.2856 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7036    0.9836   -0.2657 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4929    1.0546   -1.2274 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6779   -2.1873   -1.9296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6312   -0.7748   -3.0149 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.6780   -1.1619   -2.5531 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.4686    0.3784    2.8330 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.3026    2.6992    2.5152 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.9920   -0.7521    1.7899 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2819    0.8184    1.7991 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1862    0.2227    0.3523 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1606   -0.8581   -2.5484 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5466   -2.2792   -1.9081 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6462   -1.6424   -0.4101 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
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
  8 12  1  0
 12 13  1  0
 13 14  1  0
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 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
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 23 24  2  0
  9  3  1  0
 22 16  1  0
 23  7  1  0
  1 25  1  0
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 17 38  1  0
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 20 40  1  0
 21 41  1  0
 22 42  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       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.336   6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.336   8.470   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668   8.470   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   3.850   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       8.002   6.160   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.002   9.240   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       8.002  10.780   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       5.335   6.160   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
CONECT    1   22                                                            
CONECT    2   23                                                            
CONECT    3    5   10                                                       
CONECT    4    6   10                                                       
CONECT    5    3   12                                                       
CONECT    6    4   12                                                       
CONECT    7   10   11                                                       
CONECT    8   13   14                                                       
CONECT    9   11   24                                                       
CONECT   10    3    4    7                                                  
CONECT   11    7    9   16                                                  
CONECT   12    5    6   19                                                  
CONECT   13    8   15   20                                                  
CONECT   14    8   17   22                                                  
CONECT   15   13   16   18                                                  
CONECT   16   11   15   21                                                  
CONECT   17   14   18   23                                                  
CONECT   18   15   17   24                                                  
CONECT   19   12                                                            
CONECT   20   13                                                            
CONECT   21   16                                                            
CONECT   22    1   14                                                       
CONECT   23    2   17                                                       
CONECT   24    9   18                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

COMPND    HMDB0037253
HETATM    1  C1  UNL     1      -5.082  -1.143  -2.065  1.00  0.00           C  
HETATM    2  O1  UNL     1      -4.685  -0.306  -0.990  1.00  0.00           O  
HETATM    3  C2  UNL     1      -3.336  -0.032  -0.871  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.382  -0.524  -1.732  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.020  -0.234  -1.594  1.00  0.00           C  
HETATM    6  O2  UNL     1      -0.090  -0.735  -2.459  1.00  0.00           O  
HETATM    7  C5  UNL     1      -0.674   0.577  -0.545  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.618   1.095   0.351  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.944   0.780   0.171  1.00  0.00           C  
HETATM   10  O3  UNL     1      -3.880   1.273   1.030  1.00  0.00           O  
HETATM   11  C8  UNL     1      -4.329   0.678   2.208  1.00  0.00           C  
HETATM   12  O4  UNL     1      -1.178   1.906   1.383  1.00  0.00           O  
HETATM   13  C9  UNL     1       0.060   1.710   2.040  1.00  0.00           C  
HETATM   14  C10 UNL     1       1.140   1.297   1.100  1.00  0.00           C  
HETATM   15  C11 UNL     1       1.779   0.031   1.692  1.00  0.00           C  
HETATM   16  C12 UNL     1       2.850  -0.386   0.769  1.00  0.00           C  
HETATM   17  C13 UNL     1       4.124   0.129   0.972  1.00  0.00           C  
HETATM   18  C14 UNL     1       5.195  -0.189   0.180  1.00  0.00           C  
HETATM   19  C15 UNL     1       4.980  -1.065  -0.866  1.00  0.00           C  
HETATM   20  O5  UNL     1       6.022  -1.442  -1.722  1.00  0.00           O  
HETATM   21  C16 UNL     1       3.717  -1.582  -1.075  1.00  0.00           C  
HETATM   22  C17 UNL     1       2.650  -1.264  -0.286  1.00  0.00           C  
HETATM   23  C18 UNL     1       0.704   0.984  -0.266  1.00  0.00           C  
HETATM   24  O6  UNL     1       1.493   1.055  -1.227  1.00  0.00           O  
HETATM   25  H1  UNL     1      -4.678  -2.187  -1.930  1.00  0.00           H  
HETATM   26  H2  UNL     1      -4.631  -0.775  -3.015  1.00  0.00           H  
HETATM   27  H3  UNL     1      -6.183  -1.182  -2.105  1.00  0.00           H  
HETATM   28  H4  UNL     1      -2.678  -1.162  -2.553  1.00  0.00           H  
HETATM   29  H5  UNL     1       0.877  -0.634  -2.489  1.00  0.00           H  
HETATM   30  H6  UNL     1      -3.469   0.378   2.833  1.00  0.00           H  
HETATM   31  H7  UNL     1      -5.045  -0.140   2.062  1.00  0.00           H  
HETATM   32  H8  UNL     1      -4.885   1.474   2.783  1.00  0.00           H  
HETATM   33  H9  UNL     1      -0.054   1.017   2.911  1.00  0.00           H  
HETATM   34  H10 UNL     1       0.303   2.699   2.515  1.00  0.00           H  
HETATM   35  H11 UNL     1       1.900   2.114   1.054  1.00  0.00           H  
HETATM   36  H12 UNL     1       2.235   0.276   2.664  1.00  0.00           H  
HETATM   37  H13 UNL     1       0.992  -0.752   1.790  1.00  0.00           H  
HETATM   38  H14 UNL     1       4.282   0.818   1.799  1.00  0.00           H  
HETATM   39  H15 UNL     1       6.186   0.223   0.352  1.00  0.00           H  
HETATM   40  H16 UNL     1       6.161  -0.858  -2.548  1.00  0.00           H  
HETATM   41  H17 UNL     1       3.547  -2.279  -1.908  1.00  0.00           H  
HETATM   42  H18 UNL     1       1.646  -1.642  -0.410  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3
CONECT    3    4    4    9
CONECT    4    5   28
CONECT    5    6    7    7
CONECT    6   29
CONECT    7    8   23
CONECT    8    9    9   12
CONECT    9   10
CONECT   10   11
CONECT   11   30   31   32
CONECT   12   13
CONECT   13   14   33   34
CONECT   14   15   23   35
CONECT   15   16   36   37
CONECT   16   17   17   22
CONECT   17   18   38
CONECT   18   19   19   39
CONECT   19   20   21
CONECT   20   40
CONECT   21   22   22   41
CONECT   22   42
CONECT   23   24   24
END

HMDB0037253
     RDKit          3D
5-Hydroxy-3-(4-hydroxybenzyl)-7,8-dimethoxy-4-chromanone
 42 44  0  0  0  0  0  0  0  0999 V2000
   -5.0819   -1.1427   -2.0652 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6853   -0.3062   -0.9897 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3361   -0.0320   -0.8713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3823   -0.5245   -1.7324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0200   -0.2336   -1.5935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0900   -0.7345   -2.4594 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6743    0.5768   -0.5449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6180    1.0953    0.3506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9441    0.7800    0.1713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8798    1.2728    1.0295 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3286    0.6780    2.2078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1778    1.9062    1.3828 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0601    1.7103    2.0397 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1396    1.2974    1.0997 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7791    0.0314    1.6916 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8499   -0.3859    0.7689 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1237    0.1287    0.9717 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1950   -0.1892    0.1799 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9804   -1.0654   -0.8663 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0220   -1.4417   -1.7224 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7173   -1.5819   -1.0754 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6500   -1.2645   -0.2856 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7036    0.9836   -0.2657 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4929    1.0546   -1.2274 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6779   -2.1873   -1.9296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6312   -0.7748   -3.0149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1831   -1.1823   -2.1050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6780   -1.1619   -2.5531 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8769   -0.6342   -2.4890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4686    0.3784    2.8330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0452   -0.1396    2.0621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8847    1.4738    2.7832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0543    1.0169    2.9114 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3026    2.6992    2.5152 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8999    2.1135    1.0539 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2345    0.2760    2.6637 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9920   -0.7521    1.7899 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2819    0.8184    1.7991 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1862    0.2227    0.3523 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1606   -0.8581   -2.5484 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5466   -2.2792   -1.9081 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6462   -1.6424   -0.4101 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
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
  8 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 14 23  1  0
 23 24  2  0
  9  3  1  0
 22 16  1  0
 23  7  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  6 29  1  0
 11 30  1  0
 11 31  1  0
 11 32  1  0
 13 33  1  0
 13 34  1  0
 14 35  1  0
 15 36  1  0
 15 37  1  0
 17 38  1  0
 18 39  1  0
 20 40  1  0
 21 41  1  0
 22 42  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
7-O-Methyl-3,9-dihydropunctatin	HMDB

Chemical Formula

C₁₈H₁₈O₆

Average Molecular Weight

330.3319

Monoisotopic Molecular Weight

330.110338308

IUPAC Name

5-hydroxy-3-[(4-hydroxyphenyl)methyl]-7,8-dimethoxy-3,4-dihydro-2H-1-benzopyran-4-one

Traditional Name

5-hydroxy-3-[(4-hydroxyphenyl)methyl]-7,8-dimethoxy-2,3-dihydro-1-benzopyran-4-one

CAS Registry Number

93078-82-1

SMILES

COC1=C(OC)C2=C(C(O)=C1)C(=O)C(CC1=CC=C(O)C=C1)CO2

InChI Identifier

InChI=1S/C18H18O6/c1-22-14-8-13(20)15-16(21)11(9-24-18(15)17(14)23-2)7-10-3-5-12(19)6-4-10/h3-6,8,11,19-20H,7,9H2,1-2H3

InChI Key

GMCVGMAGOGOINY-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as homoisoflavanones. These are homoisoflavonoids with a structure based on the chromanone system. Chromanone is a bicyclic compound consisting of a 3,4-dihydro-1-benzopyran, which bears a ketone group at the 4-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Homoisoflavonoids

Sub Class

Homoisoflavans

Direct Parent

Homoisoflavanones

Alternative Parents

Substituents

Homoisoflavanone
Chromone
Chromane
Benzopyran
1-benzopyran
Anisole
Aryl ketone
Aryl alkyl ketone
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Vinylogous acid
Ketone
Oxacycle
Ether
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0037253)

Cellular substructure

Membrane (HMDB: HMDB0037253)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0037253)

Source

Exogenous

Food

Food (HMDB: HMDB0037253)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Plant

Plant (HMDB: HMDB0037253)

Not Available

Nutrient (HMDB: HMDB0037253)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	19.55 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.045 g/L	ALOGPS
logP	2.77	ALOGPS
logP	3.16	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	9.45	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	85.22 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	87.22 m³·mol⁻¹	ChemAxon
Polarizability	33.38 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]+	177.651	31661259
DarkChem	[M-H]-	179.178	31661259
DeepCCS	[M+H]+	174.762	30932474
DeepCCS	[M-H]-	172.404	30932474
DeepCCS	[M-2H]-	206.459	30932474
DeepCCS	[M+Na]+	181.686	30932474
AllCCS	[M+H]+	178.3	32859911
AllCCS	[M+H-H2O]+	175.0	32859911
AllCCS	[M+NH4]+	181.4	32859911
AllCCS	[M+Na]+	182.3	32859911
AllCCS	[M-H]-	180.5	32859911
AllCCS	[M+Na-2H]-	180.3	32859911
AllCCS	[M+HCOO]-	180.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5-Hydroxy-3-(4-hydroxybenzyl)-7,8-dimethoxy-4-chromanone	COC1=C(OC)C2=C(C(O)=C1)C(=O)C(CC1=CC=C(O)C=C1)CO2	4102.7	Standard polar	33892256
5-Hydroxy-3-(4-hydroxybenzyl)-7,8-dimethoxy-4-chromanone	COC1=C(OC)C2=C(C(O)=C1)C(=O)C(CC1=CC=C(O)C=C1)CO2	3035.3	Standard non polar	33892256
5-Hydroxy-3-(4-hydroxybenzyl)-7,8-dimethoxy-4-chromanone	COC1=C(OC)C2=C(C(O)=C1)C(=O)C(CC1=CC=C(O)C=C1)CO2	3046.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
5-Hydroxy-3-(4-hydroxybenzyl)-7,8-dimethoxy-4-chromanone,1TMS,isomer #1	COC1=CC(O[Si](C)(C)C)=C2C(=O)C(CC3=CC=C(O)C=C3)COC2=C1OC	2893.2	Semi standard non polar	33892256
5-Hydroxy-3-(4-hydroxybenzyl)-7,8-dimethoxy-4-chromanone,1TMS,isomer #2	COC1=CC(O)=C2C(=O)C(CC3=CC=C(O[Si](C)(C)C)C=C3)COC2=C1OC	2857.0	Semi standard non polar	33892256
5-Hydroxy-3-(4-hydroxybenzyl)-7,8-dimethoxy-4-chromanone,2TMS,isomer #1	COC1=CC(O[Si](C)(C)C)=C2C(=O)C(CC3=CC=C(O[Si](C)(C)C)C=C3)COC2=C1OC	2877.7	Semi standard non polar	33892256
5-Hydroxy-3-(4-hydroxybenzyl)-7,8-dimethoxy-4-chromanone,1TBDMS,isomer #1	COC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C(CC3=CC=C(O)C=C3)COC2=C1OC	3139.9	Semi standard non polar	33892256
5-Hydroxy-3-(4-hydroxybenzyl)-7,8-dimethoxy-4-chromanone,1TBDMS,isomer #2	COC1=CC(O)=C2C(=O)C(CC3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3)COC2=C1OC	3093.1	Semi standard non polar	33892256
5-Hydroxy-3-(4-hydroxybenzyl)-7,8-dimethoxy-4-chromanone,2TBDMS,isomer #1	COC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C(CC3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3)COC2=C1OC	3346.0	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 - 5-Hydroxy-3-(4-hydroxybenzyl)-7,8-dimethoxy-4-chromanone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0zfs-1948000000-24baf91917b9afb7988a	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Hydroxy-3-(4-hydroxybenzyl)-7,8-dimethoxy-4-chromanone GC-MS (2 TMS) - 70eV, Positive	splash10-0pdi-3700900000-58ba9f43202e54a1dedd	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Hydroxy-3-(4-hydroxybenzyl)-7,8-dimethoxy-4-chromanone 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 - 5-Hydroxy-3-(4-hydroxybenzyl)-7,8-dimethoxy-4-chromanone 10V, Negative-QTOF	splash10-004i-0309000000-caf099ed1c62152ef2cb	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxy-3-(4-hydroxybenzyl)-7,8-dimethoxy-4-chromanone 20V, Negative-QTOF	splash10-056s-0596000000-74980b5f888fd470efd0	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxy-3-(4-hydroxybenzyl)-7,8-dimethoxy-4-chromanone 40V, Negative-QTOF	splash10-0006-3970000000-636667d24b0206d24125	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxy-3-(4-hydroxybenzyl)-7,8-dimethoxy-4-chromanone 10V, Negative-QTOF	splash10-004i-0009000000-de11969ae6615b28f3d7	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxy-3-(4-hydroxybenzyl)-7,8-dimethoxy-4-chromanone 20V, Negative-QTOF	splash10-004i-0249000000-1e860f842d17d4288627	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxy-3-(4-hydroxybenzyl)-7,8-dimethoxy-4-chromanone 40V, Negative-QTOF	splash10-052b-9861000000-284859a99410ef1ea993	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxy-3-(4-hydroxybenzyl)-7,8-dimethoxy-4-chromanone 10V, Positive-QTOF	splash10-001i-0519000000-22658a714ae60f5b597e	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxy-3-(4-hydroxybenzyl)-7,8-dimethoxy-4-chromanone 20V, Positive-QTOF	splash10-0532-0923000000-8214373b6ff1b152d163	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxy-3-(4-hydroxybenzyl)-7,8-dimethoxy-4-chromanone 40V, Positive-QTOF	splash10-0a7i-1900000000-75a3f3191df8e128e2e2	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxy-3-(4-hydroxybenzyl)-7,8-dimethoxy-4-chromanone 10V, Positive-QTOF	splash10-001i-0009000000-2160799bc7c624fd0646	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxy-3-(4-hydroxybenzyl)-7,8-dimethoxy-4-chromanone 20V, Positive-QTOF	splash10-001i-0119000000-9f7fc50013b2b03e015e	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxy-3-(4-hydroxybenzyl)-7,8-dimethoxy-4-chromanone 40V, Positive-QTOF	splash10-0a4s-0940000000-21dfeddd4b8889afe040	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

FDB016264

KNApSAcK ID

Not Available

Chemspider ID

10254760

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21627906

PDB ID

Not Available

ChEBI ID

175209

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1859571

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 5-Hydroxy-3-(4-hydroxybenzyl)-7,8-dimethoxy-4-chromanone (HMDB0037253)

MOL for HMDB0037253 (5-Hydroxy-3-(4-hydroxybenzyl)-7,8-dimethoxy-4-chromanone)

3D MOL for HMDB0037253 (5-Hydroxy-3-(4-hydroxybenzyl)-7,8-dimethoxy-4-chromanone)

3D SDF for HMDB0037253 (5-Hydroxy-3-(4-hydroxybenzyl)-7,8-dimethoxy-4-chromanone)

3D-SDF for HMDB0037253 (5-Hydroxy-3-(4-hydroxybenzyl)-7,8-dimethoxy-4-chromanone)

PDB for HMDB0037253 (5-Hydroxy-3-(4-hydroxybenzyl)-7,8-dimethoxy-4-chromanone)

3D PDB for HMDB0037253 (5-Hydroxy-3-(4-hydroxybenzyl)-7,8-dimethoxy-4-chromanone)

SMILES for HMDB0037253 (5-Hydroxy-3-(4-hydroxybenzyl)-7,8-dimethoxy-4-chromanone)

INCHI for HMDB0037253 (5-Hydroxy-3-(4-hydroxybenzyl)-7,8-dimethoxy-4-chromanone)

Structure for HMDB0037253 (5-Hydroxy-3-(4-hydroxybenzyl)-7,8-dimethoxy-4-chromanone)

3D Structure for HMDB0037253 (5-Hydroxy-3-(4-hydroxybenzyl)-7,8-dimethoxy-4-chromanone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra