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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 23:45:57 UTC

Update Date

2022-03-07 02:55:46 UTC

HMDB ID

HMDB0038448

Secondary Accession Numbers

HMDB38448

Metabolite Identification

Common Name

(-)-5,7-Dihydroxy-3-(4-hydroxybenzyl)-4-chromanone

Description

(-)-5,7-Dihydroxy-3-(4-hydroxybenzyl)-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 (-)-5,7-Dihydroxy-3-(4-hydroxybenzyl)-4-chromanone has been detected, but not quantified in, herbs and spices. This could make (-)-5,7-dihydroxy-3-(4-hydroxybenzyl)-4-chromanone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on (-)-5,7-Dihydroxy-3-(4-hydroxybenzyl)-4-chromanone.

Structure

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

HMDB0038448
     RDKit          3D
(-)-5,7-Dihydroxy-3-(4-hydroxybenzyl)-4-chromanone
 35 37  0  0  0  0  0  0  0  0999 V2000
   -1.3071   -2.3141    0.4146 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2706   -1.0731    0.2645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5292   -0.3467    0.1857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6665   -0.8371    0.7840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7250   -2.0153    1.4916 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8394   -0.0711    0.6566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8161    1.1058   -0.0380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0183    1.8356   -0.1362 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6595    1.5633   -0.6215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4618    0.8442   -0.5287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3031    1.3173   -1.1223 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1056    0.5866   -1.0877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0150   -0.2698    0.1576 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1033   -1.2877   -0.0088 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4297   -0.6427   -0.1301 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9749   -0.2704   -1.3300 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2231    0.3326   -1.3944 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9491    0.5748   -0.2650 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1866    1.1754   -0.3595 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3927    0.1957    0.9496 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1508   -0.4050    1.0219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0240   -2.6666    1.6964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7264   -0.4721    1.1336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1797    2.5195    0.6136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6745    2.4940   -1.1615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0511   -0.1168   -1.9697 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7852    1.2341   -1.1889 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1856    0.3366    1.0548 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9446   -1.9182   -0.9035 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1584   -1.9785    0.8535 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4124   -0.4564   -2.2219 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6534    0.6268   -2.3444 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0533    0.6756   -0.4679 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9807    0.3937    1.8445 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7891   -0.6700    2.0113 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 13  2  1  0
 21 15  1  0
 10  3  1  0
  5 22  1  0
  6 23  1  0
  8 24  1  0
  9 25  1  0
 12 26  1  0
 12 27  1  0
 13 28  1  0
 14 29  1  0
 14 30  1  0
 16 31  1  0
 17 32  1  0
 19 33  1  0
 20 34  1  0
 21 35  1  0
M  END


  Mrv0541 05061310282D          

 21 23  0  0  0  0            999 V2000
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    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
    6.4302    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    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
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    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
    6.4302    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
    1.4289    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
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.8250    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
    1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    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
  3  1  1  0  0  0  0
  4  2  2  0  0  0  0
  9  1  2  0  0  0  0
  9  2  1  0  0  0  0
  9  5  1  0  0  0  0
 10  5  1  0  0  0  0
 10  8  1  0  0  0  0
 11  3  2  0  0  0  0
 11  4  1  0  0  0  0
 12  6  2  0  0  0  0
 12  7  1  0  0  0  0
 13  6  1  0  0  0  0
 14  7  2  0  0  0  0
 15 13  2  0  0  0  0
 15 14  1  0  0  0  0
 16 10  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 13  1  0  0  0  0
 20 16  2  0  0  0  0
 21  8  1  0  0  0  0
 21 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0038448

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=CC=C(CC2COC3=CC(O)=CC(O)=C3C2=O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H14O5/c17-11-3-1-9(2-4-11)5-10-8-21-14-7-12(18)6-13(19)15(14)16(10)20/h1-4,6-7,10,17-19H,5,8H2

> <INCHI_KEY>
FIASLUPJXGTCKM-UHFFFAOYSA-N

> <FORMULA>
C16H14O5

> <MOLECULAR_WEIGHT>
286.2794

> <EXACT_MASS>
286.084123558

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
28.37544250507686

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.61

> <JCHEM_LOGP>
3.1722267789999994

> <ALOGPS_LOGS>
-3.43

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.486255759802932

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.910216475688456

> <JCHEM_PKA_STRONGEST_BASIC>
-3.862547305038265

> <JCHEM_POLAR_SURFACE_AREA>
86.99

> <JCHEM_REFRACTIVITY>
76.2775

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.07e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0038448
     RDKit          3D
(-)-5,7-Dihydroxy-3-(4-hydroxybenzyl)-4-chromanone
 35 37  0  0  0  0  0  0  0  0999 V2000
   -1.3071   -2.3141    0.4146 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2706   -1.0731    0.2645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5292   -0.3467    0.1857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6665   -0.8371    0.7840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7250   -2.0153    1.4916 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8394   -0.0711    0.6566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8161    1.1058   -0.0380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0183    1.8356   -0.1362 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6595    1.5633   -0.6215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4618    0.8442   -0.5287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3031    1.3173   -1.1223 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1056    0.5866   -1.0877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0150   -0.2698    0.1576 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1033   -1.2877   -0.0088 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4297   -0.6427   -0.1301 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9749   -0.2704   -1.3300 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2231    0.3326   -1.3944 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9491    0.5748   -0.2650 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1866    1.1754   -0.3595 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3927    0.1957    0.9496 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1508   -0.4050    1.0219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0240   -2.6666    1.6964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7264   -0.4721    1.1336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1797    2.5195    0.6136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6745    2.4940   -1.1615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0511   -0.1168   -1.9697 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7852    1.2341   -1.1889 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1856    0.3366    1.0548 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9446   -1.9182   -0.9035 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1584   -1.9785    0.8535 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4124   -0.4564   -2.2219 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6534    0.6268   -2.3444 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0533    0.6756   -0.4679 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9807    0.3937    1.8445 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7891   -0.6700    2.0113 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 13  2  1  0
 21 15  1  0
 10  3  1  0
  5 22  1  0
  6 23  1  0
  8 24  1  0
  9 25  1  0
 12 26  1  0
 12 27  1  0
 13 28  1  0
 14 29  1  0
 14 30  1  0
 16 31  1  0
 17 32  1  0
 19 33  1  0
 20 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       9.336   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.669   4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.003   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.003   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       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       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  O   UNK     0      13.337   1.540   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       0.000   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   6.160   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
CONECT    1    3    9                                                       
CONECT    2    4    9                                                       
CONECT    3    1   11                                                       
CONECT    4    2   11                                                       
CONECT    5    9   10                                                       
CONECT    6   12   13                                                       
CONECT    7   12   14                                                       
CONECT    8   10   21                                                       
CONECT    9    1    2    5                                                  
CONECT   10    5    8   16                                                  
CONECT   11    3    4   17                                                  
CONECT   12    6    7   18                                                  
CONECT   13    6   15   19                                                  
CONECT   14    7   15   21                                                  
CONECT   15   13   14   16                                                  
CONECT   16   10   15   20                                                  
CONECT   17   11                                                            
CONECT   18   12                                                            
CONECT   19   13                                                            
CONECT   20   16                                                            
CONECT   21    8   14                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    HMDB0038448
HETATM    1  O1  UNL     1      -1.307  -2.314   0.415  1.00  0.00           O  
HETATM    2  C1  UNL     1      -1.271  -1.073   0.265  1.00  0.00           C  
HETATM    3  C2  UNL     1      -2.529  -0.347   0.186  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.667  -0.837   0.784  1.00  0.00           C  
HETATM    5  O2  UNL     1      -3.725  -2.015   1.492  1.00  0.00           O  
HETATM    6  C4  UNL     1      -4.839  -0.071   0.657  1.00  0.00           C  
HETATM    7  C5  UNL     1      -4.816   1.106  -0.038  1.00  0.00           C  
HETATM    8  O3  UNL     1      -6.018   1.836  -0.136  1.00  0.00           O  
HETATM    9  C6  UNL     1      -3.660   1.563  -0.622  1.00  0.00           C  
HETATM   10  C7  UNL     1      -2.462   0.844  -0.529  1.00  0.00           C  
HETATM   11  O4  UNL     1      -1.303   1.317  -1.122  1.00  0.00           O  
HETATM   12  C8  UNL     1      -0.106   0.587  -1.088  1.00  0.00           C  
HETATM   13  C9  UNL     1      -0.015  -0.270   0.158  1.00  0.00           C  
HETATM   14  C10 UNL     1       1.103  -1.288  -0.009  1.00  0.00           C  
HETATM   15  C11 UNL     1       2.430  -0.643  -0.130  1.00  0.00           C  
HETATM   16  C12 UNL     1       2.975  -0.270  -1.330  1.00  0.00           C  
HETATM   17  C13 UNL     1       4.223   0.333  -1.394  1.00  0.00           C  
HETATM   18  C14 UNL     1       4.949   0.575  -0.265  1.00  0.00           C  
HETATM   19  O5  UNL     1       6.187   1.175  -0.360  1.00  0.00           O  
HETATM   20  C15 UNL     1       4.393   0.196   0.950  1.00  0.00           C  
HETATM   21  C16 UNL     1       3.151  -0.405   1.022  1.00  0.00           C  
HETATM   22  H1  UNL     1      -3.024  -2.667   1.696  1.00  0.00           H  
HETATM   23  H2  UNL     1      -5.726  -0.472   1.134  1.00  0.00           H  
HETATM   24  H3  UNL     1      -6.180   2.520   0.614  1.00  0.00           H  
HETATM   25  H4  UNL     1      -3.674   2.494  -1.161  1.00  0.00           H  
HETATM   26  H5  UNL     1      -0.051  -0.117  -1.970  1.00  0.00           H  
HETATM   27  H6  UNL     1       0.785   1.234  -1.189  1.00  0.00           H  
HETATM   28  H7  UNL     1       0.186   0.337   1.055  1.00  0.00           H  
HETATM   29  H8  UNL     1       0.945  -1.918  -0.903  1.00  0.00           H  
HETATM   30  H9  UNL     1       1.158  -1.978   0.853  1.00  0.00           H  
HETATM   31  H10 UNL     1       2.412  -0.456  -2.222  1.00  0.00           H  
HETATM   32  H11 UNL     1       4.653   0.627  -2.344  1.00  0.00           H  
HETATM   33  H12 UNL     1       7.053   0.676  -0.468  1.00  0.00           H  
HETATM   34  H13 UNL     1       4.981   0.394   1.845  1.00  0.00           H  
HETATM   35  H14 UNL     1       2.789  -0.670   2.011  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   13
CONECT    3    4    4   10
CONECT    4    5    6
CONECT    5   22
CONECT    6    7    7   23
CONECT    7    8    9
CONECT    8   24
CONECT    9   10   10   25
CONECT   10   11
CONECT   11   12
CONECT   12   13   26   27
CONECT   13   14   28
CONECT   14   15   29   30
CONECT   15   16   16   21
CONECT   16   17   31
CONECT   17   18   18   32
CONECT   18   19   20
CONECT   19   33
CONECT   20   21   21   34
CONECT   21   35
END

HMDB0038448
     RDKit          3D
(-)-5,7-Dihydroxy-3-(4-hydroxybenzyl)-4-chromanone
 35 37  0  0  0  0  0  0  0  0999 V2000
   -1.3071   -2.3141    0.4146 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2706   -1.0731    0.2645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5292   -0.3467    0.1857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6665   -0.8371    0.7840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7250   -2.0153    1.4916 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8394   -0.0711    0.6566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8161    1.1058   -0.0380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0183    1.8356   -0.1362 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6595    1.5633   -0.6215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4618    0.8442   -0.5287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3031    1.3173   -1.1223 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1056    0.5866   -1.0877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0150   -0.2698    0.1576 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1033   -1.2877   -0.0088 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4297   -0.6427   -0.1301 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9749   -0.2704   -1.3300 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2231    0.3326   -1.3944 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9491    0.5748   -0.2650 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1866    1.1754   -0.3595 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3927    0.1957    0.9496 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1508   -0.4050    1.0219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0240   -2.6666    1.6964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7264   -0.4721    1.1336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1797    2.5195    0.6136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6745    2.4940   -1.1615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0511   -0.1168   -1.9697 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7852    1.2341   -1.1889 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1856    0.3366    1.0548 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9446   -1.9182   -0.9035 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1584   -1.9785    0.8535 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4124   -0.4564   -2.2219 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6534    0.6268   -2.3444 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0533    0.6756   -0.4679 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9807    0.3937    1.8445 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7891   -0.6700    2.0113 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 13  2  1  0
 21 15  1  0
 10  3  1  0
  5 22  1  0
  6 23  1  0
  8 24  1  0
  9 25  1  0
 12 26  1  0
 12 27  1  0
 13 28  1  0
 14 29  1  0
 14 30  1  0
 16 31  1  0
 17 32  1  0
 19 33  1  0
 20 34  1  0
 21 35  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₆H₁₄O₅

Average Molecular Weight

286.2794

Monoisotopic Molecular Weight

286.084123558

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

OC1=CC=C(CC2COC3=CC(O)=CC(O)=C3C2=O)C=C1

InChI Identifier

InChI=1S/C16H14O5/c17-11-3-1-9(2-4-11)5-10-8-21-14-7-12(18)6-13(19)15(14)16(10)20/h1-4,6-7,10,17-19H,5,8H2

InChI Key

FIASLUPJXGTCKM-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
Aryl alkyl ketone
Aryl ketone
Phenol
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Vinylogous acid
Ketone
Oxacycle
Organoheterocyclic compound
Ether
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0038448)

Cellular substructure

Membrane (HMDB: HMDB0038448)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0038448)

Source

Exogenous

Food

Food (HMDB: HMDB0038448)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Plant

Plant (HMDB: HMDB0038448)

Not Available

Nutrient (HMDB: HMDB0038448)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	103 - 104 °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	0.11 g/L	ALOGPS
logP	2.61	ALOGPS
logP	3.17	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	7.91	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	76.28 m³·mol⁻¹	ChemAxon
Polarizability	28.38 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]+	167.32	31661259
DarkChem	[M-H]-	167.448	31661259
DeepCCS	[M+H]+	167.643	30932474
DeepCCS	[M-H]-	165.285	30932474
DeepCCS	[M-2H]-	198.171	30932474
DeepCCS	[M+Na]+	173.736	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]-	168.2	32859911
AllCCS	[M+Na-2H]-	167.6	32859911
AllCCS	[M+HCOO]-	167.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(-)-5,7-Dihydroxy-3-(4-hydroxybenzyl)-4-chromanone	OC1=CC=C(CC2COC3=CC(O)=CC(O)=C3C2=O)C=C1	4017.5	Standard polar	33892256
(-)-5,7-Dihydroxy-3-(4-hydroxybenzyl)-4-chromanone	OC1=CC=C(CC2COC3=CC(O)=CC(O)=C3C2=O)C=C1	3004.0	Standard non polar	33892256
(-)-5,7-Dihydroxy-3-(4-hydroxybenzyl)-4-chromanone	OC1=CC=C(CC2COC3=CC(O)=CC(O)=C3C2=O)C=C1	2986.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(-)-5,7-Dihydroxy-3-(4-hydroxybenzyl)-4-chromanone,1TMS,isomer #1	C[Si](C)(C)OC1=CC=C(CC2COC3=CC(O)=CC(O)=C3C2=O)C=C1	2836.9	Semi standard non polar	33892256
(-)-5,7-Dihydroxy-3-(4-hydroxybenzyl)-4-chromanone,1TMS,isomer #2	C[Si](C)(C)OC1=CC(O)=C2C(=O)C(CC3=CC=C(O)C=C3)COC2=C1	2844.6	Semi standard non polar	33892256
(-)-5,7-Dihydroxy-3-(4-hydroxybenzyl)-4-chromanone,1TMS,isomer #3	C[Si](C)(C)OC1=CC(O)=CC2=C1C(=O)C(CC1=CC=C(O)C=C1)CO2	2867.6	Semi standard non polar	33892256
(-)-5,7-Dihydroxy-3-(4-hydroxybenzyl)-4-chromanone,2TMS,isomer #1	C[Si](C)(C)OC1=CC=C(CC2COC3=CC(O[Si](C)(C)C)=CC(O)=C3C2=O)C=C1	2807.6	Semi standard non polar	33892256
(-)-5,7-Dihydroxy-3-(4-hydroxybenzyl)-4-chromanone,2TMS,isomer #2	C[Si](C)(C)OC1=CC=C(CC2COC3=CC(O)=CC(O[Si](C)(C)C)=C3C2=O)C=C1	2841.1	Semi standard non polar	33892256
(-)-5,7-Dihydroxy-3-(4-hydroxybenzyl)-4-chromanone,2TMS,isomer #3	C[Si](C)(C)OC1=CC2=C(C(=O)C(CC3=CC=C(O)C=C3)CO2)C(O[Si](C)(C)C)=C1	2825.7	Semi standard non polar	33892256
(-)-5,7-Dihydroxy-3-(4-hydroxybenzyl)-4-chromanone,3TMS,isomer #1	C[Si](C)(C)OC1=CC=C(CC2COC3=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C3C2=O)C=C1	2848.5	Semi standard non polar	33892256
(-)-5,7-Dihydroxy-3-(4-hydroxybenzyl)-4-chromanone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(CC2COC3=CC(O)=CC(O)=C3C2=O)C=C1	3122.3	Semi standard non polar	33892256
(-)-5,7-Dihydroxy-3-(4-hydroxybenzyl)-4-chromanone,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C(=O)C(CC3=CC=C(O)C=C3)COC2=C1	3103.5	Semi standard non polar	33892256
(-)-5,7-Dihydroxy-3-(4-hydroxybenzyl)-4-chromanone,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC(O)=CC2=C1C(=O)C(CC1=CC=C(O)C=C1)CO2	3119.5	Semi standard non polar	33892256
(-)-5,7-Dihydroxy-3-(4-hydroxybenzyl)-4-chromanone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(CC2COC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C3C2=O)C=C1	3352.6	Semi standard non polar	33892256
(-)-5,7-Dihydroxy-3-(4-hydroxybenzyl)-4-chromanone,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(CC2COC3=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C3C2=O)C=C1	3357.9	Semi standard non polar	33892256
(-)-5,7-Dihydroxy-3-(4-hydroxybenzyl)-4-chromanone,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC2=C(C(=O)C(CC3=CC=C(O)C=C3)CO2)C(O[Si](C)(C)C(C)(C)C)=C1	3314.9	Semi standard non polar	33892256
(-)-5,7-Dihydroxy-3-(4-hydroxybenzyl)-4-chromanone,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(CC2COC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C3C2=O)C=C1	3563.3	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 - (-)-5,7-Dihydroxy-3-(4-hydroxybenzyl)-4-chromanone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-2980000000-05d742f9058da4263970	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (-)-5,7-Dihydroxy-3-(4-hydroxybenzyl)-4-chromanone GC-MS (3 TMS) - 70eV, Positive	splash10-0209-3640900000-bbf8cef12b1c8c75335a	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (-)-5,7-Dihydroxy-3-(4-hydroxybenzyl)-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 - (-)-5,7-Dihydroxy-3-(4-hydroxybenzyl)-4-chromanone 10V, Positive-QTOF	splash10-000i-0690000000-09fd743cfe9d37e3004f	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-5,7-Dihydroxy-3-(4-hydroxybenzyl)-4-chromanone 20V, Positive-QTOF	splash10-0zg0-0930000000-0f0199c00ba0fa434f4e	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-5,7-Dihydroxy-3-(4-hydroxybenzyl)-4-chromanone 40V, Positive-QTOF	splash10-0zgr-3900000000-577b601c711097324068	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-5,7-Dihydroxy-3-(4-hydroxybenzyl)-4-chromanone 10V, Negative-QTOF	splash10-000i-0390000000-0dc90695829cc807f7c8	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-5,7-Dihydroxy-3-(4-hydroxybenzyl)-4-chromanone 20V, Negative-QTOF	splash10-002r-0970000000-c6156e53fd97fc8e18db	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-5,7-Dihydroxy-3-(4-hydroxybenzyl)-4-chromanone 40V, Negative-QTOF	splash10-0pc0-2910000000-3fd239f6588f5d02d03a	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-5,7-Dihydroxy-3-(4-hydroxybenzyl)-4-chromanone 10V, Positive-QTOF	splash10-000i-0090000000-b239d41c6032c85540b2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-5,7-Dihydroxy-3-(4-hydroxybenzyl)-4-chromanone 20V, Positive-QTOF	splash10-000i-0890000000-f55686cf5883c6081517	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-5,7-Dihydroxy-3-(4-hydroxybenzyl)-4-chromanone 40V, Positive-QTOF	splash10-0ktf-2910000000-f75f98da421878dc677b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-5,7-Dihydroxy-3-(4-hydroxybenzyl)-4-chromanone 10V, Negative-QTOF	splash10-000i-0090000000-14912e1703be5edd027d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-5,7-Dihydroxy-3-(4-hydroxybenzyl)-4-chromanone 20V, Negative-QTOF	splash10-000i-0390000000-ea50625ba9e43a4b987f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-5,7-Dihydroxy-3-(4-hydroxybenzyl)-4-chromanone 40V, Negative-QTOF	splash10-054n-2910000000-8bc1b675825936231aef	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB017806

KNApSAcK ID

Not Available

Chemspider ID

8146810

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9971218

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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

Showing metabocard for (-)-5,7-Dihydroxy-3-(4-hydroxybenzyl)-4-chromanone (HMDB0038448)

MOL for HMDB0038448 ((-)-5,7-Dihydroxy-3-(4-hydroxybenzyl)-4-chromanone)

3D MOL for HMDB0038448 ((-)-5,7-Dihydroxy-3-(4-hydroxybenzyl)-4-chromanone)

3D SDF for HMDB0038448 ((-)-5,7-Dihydroxy-3-(4-hydroxybenzyl)-4-chromanone)

3D-SDF for HMDB0038448 ((-)-5,7-Dihydroxy-3-(4-hydroxybenzyl)-4-chromanone)

PDB for HMDB0038448 ((-)-5,7-Dihydroxy-3-(4-hydroxybenzyl)-4-chromanone)

3D PDB for HMDB0038448 ((-)-5,7-Dihydroxy-3-(4-hydroxybenzyl)-4-chromanone)

SMILES for HMDB0038448 ((-)-5,7-Dihydroxy-3-(4-hydroxybenzyl)-4-chromanone)

INCHI for HMDB0038448 ((-)-5,7-Dihydroxy-3-(4-hydroxybenzyl)-4-chromanone)

Structure for HMDB0038448 ((-)-5,7-Dihydroxy-3-(4-hydroxybenzyl)-4-chromanone)

3D Structure for HMDB0038448 ((-)-5,7-Dihydroxy-3-(4-hydroxybenzyl)-4-chromanone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra