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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:39:10 UTC

Update Date

2022-03-07 02:52:42 UTC

HMDB ID

HMDB0030807

Secondary Accession Numbers

HMDB30807

Metabolite Identification

Common Name

3,4-Dihydro-8-hydroxy-3-(3-hydroxy-4-methoxyphenyl)-1H-2-benzopyran-1-one

Description

3,4-Dihydro-8-hydroxy-3-(3-hydroxy-4-methoxyphenyl)-1H-2-benzopyran-1-one belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. Based on a literature review very few articles have been published on 3,4-Dihydro-8-hydroxy-3-(3-hydroxy-4-methoxyphenyl)-1H-2-benzopyran-1-one.

Structure

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

HMDB0030807
     RDKit          3D
3,4-Dihydro-8-hydroxy-3-(3-hydroxy-4-methoxyphenyl)-1H-2-benzopyran-1-one
 35 37  0  0  0  0  0  0  0  0999 V2000
    5.7188    1.0017    0.9258 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0952    0.2528   -0.0707 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7234    0.1707   -0.2456 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8901    0.8659    0.6082 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5207    0.8238    0.4850 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0087    0.0436   -0.5462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4787   -0.0372   -0.7252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0274   -0.8857    0.3885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4968   -0.7668    0.5153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2147   -1.8400    1.0713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5640   -1.7587    1.2171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2194   -0.6274    0.8201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5262    0.4573    0.2622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2289    1.5641   -0.1178 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1428    0.3801    0.1097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3746    1.4512   -0.4706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9182    2.5009   -0.8471 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9768    1.2979   -0.6109 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8290   -0.6538   -1.4036 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1950   -0.5922   -1.2553 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0352   -1.2963   -2.1204 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7905    0.7559    0.9648 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2501    0.8719    1.9298 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6264    2.0692    0.6790 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2921    1.4800    1.4197 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8552    1.3620    1.1450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7189   -0.4950   -1.6909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5222   -0.5559    1.3273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7316   -1.9451    0.1910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6646   -2.7110    1.3709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1624   -2.5702    1.6450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2960   -0.5134    0.9157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0293    2.4191   -0.5106 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4231   -1.2706   -2.2188 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0399   -1.2489   -2.0086 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  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
  6 19  1  0
 19 20  2  0
 20 21  1  0
 20  3  1  0
 18  7  1  0
 15  9  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  5 26  1  0
  7 27  1  0
  8 28  1  0
  8 29  1  0
 10 30  1  0
 11 31  1  0
 12 32  1  0
 14 33  1  0
 19 34  1  0
 21 35  1  0
M  END


  Mrv0541 05061305312D          

 21 23  0  0  0  0            999 V2000
    6.4302    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    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
    0.7145   -1.2375    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
    5.7158    0.0000    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
    2.8579    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
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    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
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -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
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    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
    6.4302    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    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
  6  5  2  0  0  0  0
  9  5  1  0  0  0  0
  9  7  2  0  0  0  0
 10  3  1  0  0  0  0
 10  8  1  0  0  0  0
 11  4  2  0  0  0  0
 12  7  1  0  0  0  0
 13  6  1  0  0  0  0
 13 12  2  0  0  0  0
 14  8  1  0  0  0  0
 14  9  1  0  0  0  0
 15 10  2  0  0  0  0
 15 11  1  0  0  0  0
 16 15  1  0  0  0  0
 17 11  1  0  0  0  0
 18 12  1  0  0  0  0
 19 16  2  0  0  0  0
 20  1  1  0  0  0  0
 20 13  1  0  0  0  0
 21 14  1  0  0  0  0
 21 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030807

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(O)C=C(C=C1)C1CC2=C(C(=O)O1)C(O)=CC=C2

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

> <INCHI_KEY>
PBILBHLAPJTJOT-UHFFFAOYSA-N

> <FORMULA>
C16H14O5

> <MOLECULAR_WEIGHT>
286.2794

> <EXACT_MASS>
286.084123558

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
29.187364644524706

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
8-hydroxy-3-(3-hydroxy-4-methoxyphenyl)-3,4-dihydro-1H-2-benzopyran-1-one

> <ALOGPS_LOGP>
2.63

> <JCHEM_LOGP>
3.486049564666666

> <ALOGPS_LOGS>
-3.63

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.027654687161956

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.413291405948051

> <JCHEM_PKA_STRONGEST_BASIC>
-4.295553684032247

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
76.1007

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.71e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
phyllodulcin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030807
     RDKit          3D
3,4-Dihydro-8-hydroxy-3-(3-hydroxy-4-methoxyphenyl)-1H-2-benzopyran-1-one
 35 37  0  0  0  0  0  0  0  0999 V2000
    5.7188    1.0017    0.9258 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0952    0.2528   -0.0707 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7234    0.1707   -0.2456 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8901    0.8659    0.6082 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5207    0.8238    0.4850 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0087    0.0436   -0.5462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4787   -0.0372   -0.7252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0274   -0.8857    0.3885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4968   -0.7668    0.5153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2147   -1.8400    1.0713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5640   -1.7587    1.2171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2194   -0.6274    0.8201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5262    0.4573    0.2622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2289    1.5641   -0.1178 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1428    0.3801    0.1097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3746    1.4512   -0.4706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9182    2.5009   -0.8471 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9768    1.2979   -0.6109 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8290   -0.6538   -1.4036 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1950   -0.5922   -1.2553 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0352   -1.2963   -2.1204 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7905    0.7559    0.9648 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2501    0.8719    1.9298 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6264    2.0692    0.6790 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2921    1.4800    1.4197 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8552    1.3620    1.1450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7189   -0.4950   -1.6909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5222   -0.5559    1.3273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7316   -1.9451    0.1910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6646   -2.7110    1.3709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1624   -2.5702    1.6450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2960   -0.5134    0.9157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0293    2.4191   -0.5106 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4231   -1.2706   -2.2188 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0399   -1.2489   -2.0086 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  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
  6 19  1  0
 19 20  2  0
 20 21  1  0
 20  3  1  0
 18  7  1  0
 15  9  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  5 26  1  0
  7 27  1  0
  8 28  1  0
  8 29  1  0
 10 30  1  0
 11 31  1  0
 12 32  1  0
 14 33  1  0
 19 34  1  0
 21 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      12.003   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       9.336   3.850   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      12.003   2.310   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
CONECT    1   20                                                            
CONECT    2    3    4                                                       
CONECT    3    2   10                                                       
CONECT    4    2   11                                                       
CONECT    5    6    9                                                       
CONECT    6    5   13                                                       
CONECT    7    9   12                                                       
CONECT    8   10   14                                                       
CONECT    9    5    7   14                                                  
CONECT   10    3    8   15                                                  
CONECT   11    4   15   17                                                  
CONECT   12    7   13   18                                                  
CONECT   13    6   12   20                                                  
CONECT   14    8    9   21                                                  
CONECT   15   10   11   16                                                  
CONECT   16   15   19   21                                                  
CONECT   17   11                                                            
CONECT   18   12                                                            
CONECT   19   16                                                            
CONECT   20    1   13                                                       
CONECT   21   14   16                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    HMDB0030807
HETATM    1  C1  UNL     1       5.719   1.002   0.926  1.00  0.00           C  
HETATM    2  O1  UNL     1       5.095   0.253  -0.071  1.00  0.00           O  
HETATM    3  C2  UNL     1       3.723   0.171  -0.246  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.890   0.866   0.608  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.521   0.824   0.485  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.009   0.044  -0.546  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.479  -0.037  -0.725  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.027  -0.886   0.388  1.00  0.00           C  
HETATM    9  C8  UNL     1      -2.497  -0.767   0.515  1.00  0.00           C  
HETATM   10  C9  UNL     1      -3.215  -1.840   1.071  1.00  0.00           C  
HETATM   11  C10 UNL     1      -4.564  -1.759   1.217  1.00  0.00           C  
HETATM   12  C11 UNL     1      -5.219  -0.627   0.820  1.00  0.00           C  
HETATM   13  C12 UNL     1      -4.526   0.457   0.262  1.00  0.00           C  
HETATM   14  O2  UNL     1      -5.229   1.564  -0.118  1.00  0.00           O  
HETATM   15  C13 UNL     1      -3.143   0.380   0.110  1.00  0.00           C  
HETATM   16  C14 UNL     1      -2.375   1.451  -0.471  1.00  0.00           C  
HETATM   17  O3  UNL     1      -2.918   2.501  -0.847  1.00  0.00           O  
HETATM   18  O4  UNL     1      -0.977   1.298  -0.611  1.00  0.00           O  
HETATM   19  C15 UNL     1       1.829  -0.654  -1.404  1.00  0.00           C  
HETATM   20  C16 UNL     1       3.195  -0.592  -1.255  1.00  0.00           C  
HETATM   21  O5  UNL     1       4.035  -1.296  -2.120  1.00  0.00           O  
HETATM   22  H1  UNL     1       6.790   0.756   0.965  1.00  0.00           H  
HETATM   23  H2  UNL     1       5.250   0.872   1.930  1.00  0.00           H  
HETATM   24  H3  UNL     1       5.626   2.069   0.679  1.00  0.00           H  
HETATM   25  H4  UNL     1       3.292   1.480   1.420  1.00  0.00           H  
HETATM   26  H5  UNL     1       0.855   1.362   1.145  1.00  0.00           H  
HETATM   27  H6  UNL     1      -0.719  -0.495  -1.691  1.00  0.00           H  
HETATM   28  H7  UNL     1      -0.522  -0.556   1.327  1.00  0.00           H  
HETATM   29  H8  UNL     1      -0.732  -1.945   0.191  1.00  0.00           H  
HETATM   30  H9  UNL     1      -2.665  -2.711   1.371  1.00  0.00           H  
HETATM   31  H10 UNL     1      -5.162  -2.570   1.645  1.00  0.00           H  
HETATM   32  H11 UNL     1      -6.296  -0.513   0.916  1.00  0.00           H  
HETATM   33  H12 UNL     1      -5.029   2.419  -0.511  1.00  0.00           H  
HETATM   34  H13 UNL     1       1.423  -1.271  -2.219  1.00  0.00           H  
HETATM   35  H14 UNL     1       5.040  -1.249  -2.009  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3
CONECT    3    4    4   20
CONECT    4    5   25
CONECT    5    6    6   26
CONECT    6    7   19
CONECT    7    8   18   27
CONECT    8    9   28   29
CONECT    9   10   10   15
CONECT   10   11   30
CONECT   11   12   12   31
CONECT   12   13   32
CONECT   13   14   15   15
CONECT   14   33
CONECT   15   16
CONECT   16   17   17   18
CONECT   19   20   20   34
CONECT   20   21
CONECT   21   35
END

HMDB0030807
     RDKit          3D
3,4-Dihydro-8-hydroxy-3-(3-hydroxy-4-methoxyphenyl)-1H-2-benzopyran-1-one
 35 37  0  0  0  0  0  0  0  0999 V2000
    5.7188    1.0017    0.9258 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0952    0.2528   -0.0707 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7234    0.1707   -0.2456 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8901    0.8659    0.6082 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5207    0.8238    0.4850 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0087    0.0436   -0.5462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4787   -0.0372   -0.7252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0274   -0.8857    0.3885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4968   -0.7668    0.5153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2147   -1.8400    1.0713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5640   -1.7587    1.2171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2194   -0.6274    0.8201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5262    0.4573    0.2622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2289    1.5641   -0.1178 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1428    0.3801    0.1097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3746    1.4512   -0.4706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9182    2.5009   -0.8471 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9768    1.2979   -0.6109 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8290   -0.6538   -1.4036 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1950   -0.5922   -1.2553 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0352   -1.2963   -2.1204 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7905    0.7559    0.9648 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2501    0.8719    1.9298 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6264    2.0692    0.6790 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2921    1.4800    1.4197 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8552    1.3620    1.1450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7189   -0.4950   -1.6909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5222   -0.5559    1.3273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7316   -1.9451    0.1910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6646   -2.7110    1.3709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1624   -2.5702    1.6450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2960   -0.5134    0.9157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0293    2.4191   -0.5106 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4231   -1.2706   -2.2188 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0399   -1.2489   -2.0086 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  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
  6 19  1  0
 19 20  2  0
 20 21  1  0
 20  3  1  0
 18  7  1  0
 15  9  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  5 26  1  0
  7 27  1  0
  8 28  1  0
  8 29  1  0
 10 30  1  0
 11 31  1  0
 12 32  1  0
 14 33  1  0
 19 34  1  0
 21 35  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3,4-dihydro-3-(3-Hydroxy-4-methoxyphenyl)-8-hydroxyisocoumarin	HMDB
Phyllodulcin	HMDB
Phyllodulcinol	HMDB
Phyllodulcin, (R)-isomer	MeSH

Chemical Formula

C₁₆H₁₄O₅

Average Molecular Weight

286.2794

Monoisotopic Molecular Weight

286.084123558

IUPAC Name

8-hydroxy-3-(3-hydroxy-4-methoxyphenyl)-3,4-dihydro-1H-2-benzopyran-1-one

Traditional Name

phyllodulcin

CAS Registry Number

21499-23-0

SMILES

COC1=C(O)C=C(C=C1)C1CC2=C(C(=O)O1)C(O)=CC=C2

InChI Identifier

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

InChI Key

PBILBHLAPJTJOT-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Benzopyran
Isochromane
2-benzopyran
Methoxyphenol
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Monocyclic benzene moiety
Vinylogous acid
Carboxylic acid ester
Lactone
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Ether
Monocarboxylic acid or derivatives
Organic oxide
Organooxygen compound
Hydrocarbon derivative
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: HMDB0030807)

Cellular substructure

Membrane (HMDB: HMDB0030807)

Source

Exogenous

Food

Food (HMDB: HMDB0030807)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	120 °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	0.067 g/L	ALOGPS
logP	2.63	ALOGPS
logP	3.49	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	9.41	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	76.1 m³·mol⁻¹	ChemAxon
Polarizability	29.19 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]+	166.212	31661259
DarkChem	[M-H]-	167.3	31661259
DeepCCS	[M+H]+	165.488	30932474
DeepCCS	[M-H]-	163.13	30932474
DeepCCS	[M-2H]-	196.746	30932474
DeepCCS	[M+Na]+	172.689	30932474
AllCCS	[M+H]+	167.0	32859911
AllCCS	[M+H-H2O]+	163.3	32859911
AllCCS	[M+NH4]+	170.4	32859911
AllCCS	[M+Na]+	171.4	32859911
AllCCS	[M-H]-	168.5	32859911
AllCCS	[M+Na-2H]-	167.9	32859911
AllCCS	[M+HCOO]-	167.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3,4-Dihydro-8-hydroxy-3-(3-hydroxy-4-methoxyphenyl)-1H-2-benzopyran-1-one	COC1=C(O)C=C(C=C1)C1CC2=C(C(=O)O1)C(O)=CC=C2	3911.9	Standard polar	33892256
3,4-Dihydro-8-hydroxy-3-(3-hydroxy-4-methoxyphenyl)-1H-2-benzopyran-1-one	COC1=C(O)C=C(C=C1)C1CC2=C(C(=O)O1)C(O)=CC=C2	2694.9	Standard non polar	33892256
3,4-Dihydro-8-hydroxy-3-(3-hydroxy-4-methoxyphenyl)-1H-2-benzopyran-1-one	COC1=C(O)C=C(C=C1)C1CC2=C(C(=O)O1)C(O)=CC=C2	2702.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3,4-Dihydro-8-hydroxy-3-(3-hydroxy-4-methoxyphenyl)-1H-2-benzopyran-1-one,1TMS,isomer #1	COC1=CC=C(C2CC3=CC=CC(O)=C3C(=O)O2)C=C1O[Si](C)(C)C	2734.5	Semi standard non polar	33892256
3,4-Dihydro-8-hydroxy-3-(3-hydroxy-4-methoxyphenyl)-1H-2-benzopyran-1-one,1TMS,isomer #2	COC1=CC=C(C2CC3=CC=CC(O[Si](C)(C)C)=C3C(=O)O2)C=C1O	2737.6	Semi standard non polar	33892256
3,4-Dihydro-8-hydroxy-3-(3-hydroxy-4-methoxyphenyl)-1H-2-benzopyran-1-one,2TMS,isomer #1	COC1=CC=C(C2CC3=CC=CC(O[Si](C)(C)C)=C3C(=O)O2)C=C1O[Si](C)(C)C	2725.2	Semi standard non polar	33892256
3,4-Dihydro-8-hydroxy-3-(3-hydroxy-4-methoxyphenyl)-1H-2-benzopyran-1-one,1TBDMS,isomer #1	COC1=CC=C(C2CC3=CC=CC(O)=C3C(=O)O2)C=C1O[Si](C)(C)C(C)(C)C	2980.0	Semi standard non polar	33892256
3,4-Dihydro-8-hydroxy-3-(3-hydroxy-4-methoxyphenyl)-1H-2-benzopyran-1-one,1TBDMS,isomer #2	COC1=CC=C(C2CC3=CC=CC(O[Si](C)(C)C(C)(C)C)=C3C(=O)O2)C=C1O	2985.1	Semi standard non polar	33892256
3,4-Dihydro-8-hydroxy-3-(3-hydroxy-4-methoxyphenyl)-1H-2-benzopyran-1-one,2TBDMS,isomer #1	COC1=CC=C(C2CC3=CC=CC(O[Si](C)(C)C(C)(C)C)=C3C(=O)O2)C=C1O[Si](C)(C)C(C)(C)C	3186.3	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3,4-Dihydro-8-hydroxy-3-(3-hydroxy-4-methoxyphenyl)-1H-2-benzopyran-1-one GC-MS (Non-derivatized) - 70eV, Positive	splash10-05gi-0890000000-637f38ea5657aa2322fe	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,4-Dihydro-8-hydroxy-3-(3-hydroxy-4-methoxyphenyl)-1H-2-benzopyran-1-one GC-MS (2 TMS) - 70eV, Positive	splash10-0aou-3954700000-ceb37d8c2a2200a30fd3	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,4-Dihydro-8-hydroxy-3-(3-hydroxy-4-methoxyphenyl)-1H-2-benzopyran-1-one GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dihydro-8-hydroxy-3-(3-hydroxy-4-methoxyphenyl)-1H-2-benzopyran-1-one 10V, Positive-QTOF	splash10-000i-0190000000-818541c2076a472cfc19	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dihydro-8-hydroxy-3-(3-hydroxy-4-methoxyphenyl)-1H-2-benzopyran-1-one 20V, Positive-QTOF	splash10-000i-0690000000-6d1b7f7c2df1633788f8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dihydro-8-hydroxy-3-(3-hydroxy-4-methoxyphenyl)-1H-2-benzopyran-1-one 40V, Positive-QTOF	splash10-0100-2940000000-8157eb0461c6c96c7ce9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dihydro-8-hydroxy-3-(3-hydroxy-4-methoxyphenyl)-1H-2-benzopyran-1-one 10V, Negative-QTOF	splash10-000l-0090000000-8e6dfd41375df01be56a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dihydro-8-hydroxy-3-(3-hydroxy-4-methoxyphenyl)-1H-2-benzopyran-1-one 20V, Negative-QTOF	splash10-000l-0190000000-fb78cd0807c7bd2c924e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dihydro-8-hydroxy-3-(3-hydroxy-4-methoxyphenyl)-1H-2-benzopyran-1-one 40V, Negative-QTOF	splash10-07n9-1980000000-98d86c79014aa586149e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dihydro-8-hydroxy-3-(3-hydroxy-4-methoxyphenyl)-1H-2-benzopyran-1-one 10V, Positive-QTOF	splash10-000i-0090000000-813cd29461c01013eb3b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dihydro-8-hydroxy-3-(3-hydroxy-4-methoxyphenyl)-1H-2-benzopyran-1-one 20V, Positive-QTOF	splash10-000l-0190000000-41b0d052e46af7989b77	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dihydro-8-hydroxy-3-(3-hydroxy-4-methoxyphenyl)-1H-2-benzopyran-1-one 40V, Positive-QTOF	splash10-0300-0590000000-2ac506e666798cf7f0cf	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dihydro-8-hydroxy-3-(3-hydroxy-4-methoxyphenyl)-1H-2-benzopyran-1-one 10V, Negative-QTOF	splash10-000i-0090000000-14912e1703be5edd027d	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dihydro-8-hydroxy-3-(3-hydroxy-4-methoxyphenyl)-1H-2-benzopyran-1-one 20V, Negative-QTOF	splash10-000i-0290000000-d69529081f6ad508ee6c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dihydro-8-hydroxy-3-(3-hydroxy-4-methoxyphenyl)-1H-2-benzopyran-1-one 40V, Negative-QTOF	splash10-03dr-2960000000-2b65917f6292cd70b826	2021-09-23	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

FDB002757

KNApSAcK ID

C00002894

Chemspider ID

144311

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

164615

PDB ID

Not Available

ChEBI ID

174724

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 3,4-Dihydro-8-hydroxy-3-(3-hydroxy-4-methoxyphenyl)-1H-2-benzopyran-1-one (HMDB0030807)

MOL for HMDB0030807 (3,4-Dihydro-8-hydroxy-3-(3-hydroxy-4-methoxyphenyl)-1H-2-benzopyran-1-one)

3D MOL for HMDB0030807 (3,4-Dihydro-8-hydroxy-3-(3-hydroxy-4-methoxyphenyl)-1H-2-benzopyran-1-one)

3D SDF for HMDB0030807 (3,4-Dihydro-8-hydroxy-3-(3-hydroxy-4-methoxyphenyl)-1H-2-benzopyran-1-one)

3D-SDF for HMDB0030807 (3,4-Dihydro-8-hydroxy-3-(3-hydroxy-4-methoxyphenyl)-1H-2-benzopyran-1-one)

PDB for HMDB0030807 (3,4-Dihydro-8-hydroxy-3-(3-hydroxy-4-methoxyphenyl)-1H-2-benzopyran-1-one)

3D PDB for HMDB0030807 (3,4-Dihydro-8-hydroxy-3-(3-hydroxy-4-methoxyphenyl)-1H-2-benzopyran-1-one)

SMILES for HMDB0030807 (3,4-Dihydro-8-hydroxy-3-(3-hydroxy-4-methoxyphenyl)-1H-2-benzopyran-1-one)

INCHI for HMDB0030807 (3,4-Dihydro-8-hydroxy-3-(3-hydroxy-4-methoxyphenyl)-1H-2-benzopyran-1-one)

Structure for HMDB0030807 (3,4-Dihydro-8-hydroxy-3-(3-hydroxy-4-methoxyphenyl)-1H-2-benzopyran-1-one)

3D Structure for HMDB0030807 (3,4-Dihydro-8-hydroxy-3-(3-hydroxy-4-methoxyphenyl)-1H-2-benzopyran-1-one)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra