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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 01:50:49 UTC

Update Date

2022-03-07 02:56:33 UTC

HMDB ID

HMDB0040314

Secondary Accession Numbers

HMDB40314

Metabolite Identification

Common Name

2,4',5,7-Tetrahydroxyflavanone

Description

2,4',5,7-Tetrahydroxyflavanone, also known as 2-hydroxynaringenin, belongs to the class of organic compounds known as 7-hydroxyflavonoids. These are flavonoids that bear one hydroxyl group at the C-7 position of the flavonoid skeleton. 2,4',5,7-Tetrahydroxyflavanone has been detected, but not quantified in, fruits. This could make 2,4',5,7-tetrahydroxyflavanone a potential biomarker for the consumption of these foods. 2,4',5,7-Tetrahydroxyflavanone is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on 2,4',5,7-Tetrahydroxyflavanone.

Structure

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

HMDB0040314
     RDKit          3D
2,4',5,7-Tetrahydroxyflavanone
 33 35  0  0  0  0  0  0  0  0999 V2000
   -1.7499   -2.8313   -1.1201 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3298   -1.8539   -0.4800 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1272   -1.7122   -0.1137 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5050   -0.3177   -0.5316 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2652   -0.2398   -1.9256 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8998    0.0524   -0.2003 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7998   -0.7835    0.4244 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0961   -0.3833    0.7087 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5463    0.8770    0.3769 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8461    1.3075    0.6502 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6460    1.7167   -0.2492 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3542    1.3223   -0.5341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3518    0.6533    0.0516 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7163    0.4368    0.1883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5446    1.4475    0.5751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9097    1.2752    0.7222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7045    2.3607    1.1241 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4287    0.0440    0.4670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6166   -1.0237    0.0675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1551   -2.2383   -0.1794 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2624   -0.8082   -0.0666 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6934   -2.4172   -0.7306 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1843   -1.9010    0.9635 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9932    0.3696   -2.2692 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4697   -1.7811    0.6969 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7988   -1.0639    1.2061 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4876    0.6916    1.1013 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9436    2.7151   -0.5322 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6425    1.9860   -1.0295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1293    2.4279    0.7783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0685    2.9250    0.3478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4975   -0.1430    0.5685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8340   -3.1107   -0.4506 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
  4 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 21  2  1  0
 12  6  1  0
 21 14  1  0
  3 22  1  0
  3 23  1  0
  5 24  1  0
  7 25  1  0
  8 26  1  0
 10 27  1  0
 11 28  1  0
 12 29  1  0
 15 30  1  0
 17 31  1  0
 18 32  1  0
 20 33  1  0
M  END

  Mrv0541 05061311452D          

 21 23  0  0  0  0            999 V2000
    5.6296   -0.4887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3815    0.9185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4421   -0.3455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1939    1.0618    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
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0993    0.1433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7242    0.4298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    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
    7.5367    0.5730    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5690   -0.7752    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  2  0  0  0  0
  8  1  2  0  0  0  0
  8  2  1  0  0  0  0
  9  3  2  0  0  0  0
  9  4  1  0  0  0  0
 10  5  2  0  0  0  0
 10  6  1  0  0  0  0
 11  5  1  0  0  0  0
 12  7  1  0  0  0  0
 13  6  2  0  0  0  0
 14 11  2  0  0  0  0
 14 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15  7  1  0  0  0  0
 15  8  1  0  0  0  0
 16  9  1  0  0  0  0
 17 10  1  0  0  0  0
 18 11  1  0  0  0  0
 19 12  2  0  0  0  0
 20 15  1  0  0  0  0
 21 13  1  0  0  0  0
 21 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0040314

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=CC=C(C=C1)C1(O)CC(=O)C2=C(O)C=C(O)C=C2O1

> <INCHI_IDENTIFIER>
InChI=1S/C15H12O6/c16-9-3-1-8(2-4-9)15(20)7-12(19)14-11(18)5-10(17)6-13(14)21-15/h1-6,16-18,20H,7H2

> <INCHI_KEY>
NFENYLPEYDNIMO-UHFFFAOYSA-N

> <FORMULA>
C15H12O6

> <MOLECULAR_WEIGHT>
288.2522

> <EXACT_MASS>
288.063388116

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
27.394085820175277

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,5,7-trihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one

> <ALOGPS_LOGP>
1.18

> <JCHEM_LOGP>
2.6454240086666667

> <ALOGPS_LOGS>
-2.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.407311840715987

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.862767849788797

> <JCHEM_PKA_STRONGEST_BASIC>
-3.8642673430553094

> <JCHEM_POLAR_SURFACE_AREA>
107.22

> <JCHEM_REFRACTIVITY>
72.75710000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.94e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,5,7-trihydroxy-2-(4-hydroxyphenyl)-3H-1-benzopyran-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0040314
     RDKit          3D
2,4',5,7-Tetrahydroxyflavanone
 33 35  0  0  0  0  0  0  0  0999 V2000
   -1.7499   -2.8313   -1.1201 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3298   -1.8539   -0.4800 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1272   -1.7122   -0.1137 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5050   -0.3177   -0.5316 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2652   -0.2398   -1.9256 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8998    0.0524   -0.2003 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7998   -0.7835    0.4244 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0961   -0.3833    0.7087 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5463    0.8770    0.3769 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8461    1.3075    0.6502 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6460    1.7167   -0.2492 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3542    1.3223   -0.5341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3518    0.6533    0.0516 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7163    0.4368    0.1883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5446    1.4475    0.5751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9097    1.2752    0.7222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7045    2.3607    1.1241 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4287    0.0440    0.4670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6166   -1.0237    0.0675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1551   -2.2383   -0.1794 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2624   -0.8082   -0.0666 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6934   -2.4172   -0.7306 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1843   -1.9010    0.9635 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9932    0.3696   -2.2692 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4697   -1.7811    0.6969 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7988   -1.0639    1.2061 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4876    0.6916    1.1013 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9436    2.7151   -0.5322 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6425    1.9860   -1.0295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1293    2.4279    0.7783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0685    2.9250    0.3478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4975   -0.1430    0.5685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8340   -3.1107   -0.4506 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
  4 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 21  2  1  0
 12  6  1  0
 21 14  1  0
  3 22  1  0
  3 23  1  0
  5 24  1  0
  7 25  1  0
  8 26  1  0
 10 27  1  0
 11 28  1  0
 12 29  1  0
 15 30  1  0
 17 31  1  0
 18 32  1  0
 20 33  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      10.509  -0.912   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.045   1.715   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.025  -0.645   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.562   1.982   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -0.770   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       9.519   0.267   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.552   0.802   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      14.069   1.070   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       8.529  -1.447   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
CONECT    1    3    8                                                       
CONECT    2    4    8                                                       
CONECT    3    1    9                                                       
CONECT    4    2    9                                                       
CONECT    5   10   11                                                       
CONECT    6   10   13                                                       
CONECT    7   12   15                                                       
CONECT    8    1    2   15                                                  
CONECT    9    3    4   16                                                  
CONECT   10    5    6   17                                                  
CONECT   11    5   14   18                                                  
CONECT   12    7   14   19                                                  
CONECT   13    6   14   21                                                  
CONECT   14   11   12   13                                                  
CONECT   15    7    8   20   21                                             
CONECT   16    9                                                            
CONECT   17   10                                                            
CONECT   18   11                                                            
CONECT   19   12                                                            
CONECT   20   15                                                            
CONECT   21   13   15                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    HMDB0040314
HETATM    1  O1  UNL     1      -1.750  -2.831  -1.120  1.00  0.00           O  
HETATM    2  C1  UNL     1      -1.330  -1.854  -0.480  1.00  0.00           C  
HETATM    3  C2  UNL     1       0.127  -1.712  -0.114  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.505  -0.318  -0.532  1.00  0.00           C  
HETATM    5  O2  UNL     1       0.265  -0.240  -1.926  1.00  0.00           O  
HETATM    6  C4  UNL     1       1.900   0.052  -0.200  1.00  0.00           C  
HETATM    7  C5  UNL     1       2.800  -0.783   0.424  1.00  0.00           C  
HETATM    8  C6  UNL     1       4.096  -0.383   0.709  1.00  0.00           C  
HETATM    9  C7  UNL     1       4.546   0.877   0.377  1.00  0.00           C  
HETATM   10  O3  UNL     1       5.846   1.308   0.650  1.00  0.00           O  
HETATM   11  C8  UNL     1       3.646   1.717  -0.249  1.00  0.00           C  
HETATM   12  C9  UNL     1       2.354   1.322  -0.534  1.00  0.00           C  
HETATM   13  O4  UNL     1      -0.352   0.653   0.052  1.00  0.00           O  
HETATM   14  C10 UNL     1      -1.716   0.437   0.188  1.00  0.00           C  
HETATM   15  C11 UNL     1      -2.545   1.448   0.575  1.00  0.00           C  
HETATM   16  C12 UNL     1      -3.910   1.275   0.722  1.00  0.00           C  
HETATM   17  O5  UNL     1      -4.704   2.361   1.124  1.00  0.00           O  
HETATM   18  C13 UNL     1      -4.429   0.044   0.467  1.00  0.00           C  
HETATM   19  C14 UNL     1      -3.617  -1.024   0.067  1.00  0.00           C  
HETATM   20  O6  UNL     1      -4.155  -2.238  -0.179  1.00  0.00           O  
HETATM   21  C15 UNL     1      -2.262  -0.808  -0.067  1.00  0.00           C  
HETATM   22  H1  UNL     1       0.693  -2.417  -0.731  1.00  0.00           H  
HETATM   23  H2  UNL     1       0.184  -1.901   0.964  1.00  0.00           H  
HETATM   24  H3  UNL     1       0.993   0.370  -2.269  1.00  0.00           H  
HETATM   25  H4  UNL     1       2.470  -1.781   0.697  1.00  0.00           H  
HETATM   26  H5  UNL     1       4.799  -1.064   1.206  1.00  0.00           H  
HETATM   27  H6  UNL     1       6.488   0.692   1.101  1.00  0.00           H  
HETATM   28  H7  UNL     1       3.944   2.715  -0.532  1.00  0.00           H  
HETATM   29  H8  UNL     1       1.642   1.986  -1.030  1.00  0.00           H  
HETATM   30  H9  UNL     1      -2.129   2.428   0.778  1.00  0.00           H  
HETATM   31  H10 UNL     1      -5.069   2.925   0.348  1.00  0.00           H  
HETATM   32  H11 UNL     1      -5.497  -0.143   0.568  1.00  0.00           H  
HETATM   33  H12 UNL     1      -3.834  -3.111  -0.451  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   21
CONECT    3    4   22   23
CONECT    4    5    6   13
CONECT    5   24
CONECT    6    7    7   12
CONECT    7    8   25
CONECT    8    9    9   26
CONECT    9   10   11
CONECT   10   27
CONECT   11   12   12   28
CONECT   12   29
CONECT   13   14
CONECT   14   15   15   21
CONECT   15   16   30
CONECT   16   17   18   18
CONECT   17   31
CONECT   18   19   32
CONECT   19   20   21   21
CONECT   20   33
END

HMDB0040314
     RDKit          3D
2,4',5,7-Tetrahydroxyflavanone
 33 35  0  0  0  0  0  0  0  0999 V2000
   -1.7499   -2.8313   -1.1201 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3298   -1.8539   -0.4800 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1272   -1.7122   -0.1137 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5050   -0.3177   -0.5316 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2652   -0.2398   -1.9256 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8998    0.0524   -0.2003 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7998   -0.7835    0.4244 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0961   -0.3833    0.7087 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5463    0.8770    0.3769 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8461    1.3075    0.6502 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6460    1.7167   -0.2492 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3542    1.3223   -0.5341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3518    0.6533    0.0516 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7163    0.4368    0.1883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5446    1.4475    0.5751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9097    1.2752    0.7222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7045    2.3607    1.1241 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4287    0.0440    0.4670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6166   -1.0237    0.0675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1551   -2.2383   -0.1794 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2624   -0.8082   -0.0666 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6934   -2.4172   -0.7306 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1843   -1.9010    0.9635 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9932    0.3696   -2.2692 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4697   -1.7811    0.6969 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7988   -1.0639    1.2061 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4876    0.6916    1.1013 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9436    2.7151   -0.5322 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6425    1.9860   -1.0295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1293    2.4279    0.7783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0685    2.9250    0.3478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4975   -0.1430    0.5685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8340   -3.1107   -0.4506 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
  4 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 21  2  1  0
 12  6  1  0
 21 14  1  0
  3 22  1  0
  3 23  1  0
  5 24  1  0
  7 25  1  0
  8 26  1  0
 10 27  1  0
 11 28  1  0
 12 29  1  0
 15 30  1  0
 17 31  1  0
 18 32  1  0
 20 33  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2,3-Dihydro-2,5,7-trihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one	ChEBI
2,5,7-Trihydroxy-2-(4-hydroxyphenyl)-3H-1-benzopyran-4-one	ChEBI
2,5,7-Trihydroxy-2-(4-hydroxyphenyl)-3H-chromen-4-one	ChEBI
2-Hydroxynaringenin	ChEBI
2,3-dihydro-2,5,7-Trihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one, 9ci	HMDB
2,4',5,7-Tetrahydroxyflavanone	ChEBI

Chemical Formula

C₁₅H₁₂O₆

Average Molecular Weight

288.2522

Monoisotopic Molecular Weight

288.063388116

IUPAC Name

2,5,7-trihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one

Traditional Name

2,5,7-trihydroxy-2-(4-hydroxyphenyl)-3H-1-benzopyran-4-one

CAS Registry Number

58124-18-8

SMILES

OC1=CC=C(C=C1)C1(O)CC(=O)C2=C(O)C=C(O)C=C2O1

InChI Identifier

InChI=1S/C15H12O6/c16-9-3-1-8(2-4-9)15(20)7-12(19)14-11(18)5-10(17)6-13(14)21-15/h1-6,16-18,20H,7H2

InChI Key

NFENYLPEYDNIMO-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 7-hydroxyflavonoids. These are flavonoids that bear one hydroxyl group at the C-7 position of the flavonoid skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Hydroxyflavonoids

Direct Parent

7-hydroxyflavonoids

Alternative Parents

Substituents

4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavan
Chromone
Benzopyran
Chromane
1-benzopyran
Aryl ketone
Aryl alkyl ketone
Phenol
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Vinylogous acid
Ketone
Hemiacetal
Oxacycle
Organoheterocyclic compound
Polyol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0040314)
Cytoplasm (HMDB: HMDB0040314)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0040314)

Source

Exogenous

Exogenous (HMDB: HMDB0040314)

Food

Food (HMDB: HMDB0040314)

Fruit

Fruits (FooDB: FOOD00871)

Endogenous

Plant

Plant (HMDB: HMDB0040314)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0040314)

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	4979 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	0.49 g/L	ALOGPS
logP	1.18	ALOGPS
logP	2.65	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	7.86	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	107.22 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	72.76 m³·mol⁻¹	ChemAxon
Polarizability	27.39 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]+	167.5	31661259
DarkChem	[M-H]-	164.155	31661259
DeepCCS	[M+H]+	167.193	30932474
DeepCCS	[M-H]-	164.835	30932474
DeepCCS	[M-2H]-	197.721	30932474
DeepCCS	[M+Na]+	173.287	30932474
AllCCS	[M+H]+	166.4	32859911
AllCCS	[M+H-H2O]+	162.7	32859911
AllCCS	[M+NH4]+	169.9	32859911
AllCCS	[M+Na]+	170.9	32859911
AllCCS	[M-H]-	165.6	32859911
AllCCS	[M+Na-2H]-	165.0	32859911
AllCCS	[M+HCOO]-	164.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2,4',5,7-Tetrahydroxyflavanone	OC1=CC=C(C=C1)C1(O)CC(=O)C2=C(O)C=C(O)C=C2O1	4310.3	Standard polar	33892256
2,4',5,7-Tetrahydroxyflavanone	OC1=CC=C(C=C1)C1(O)CC(=O)C2=C(O)C=C(O)C=C2O1	2936.9	Standard non polar	33892256
2,4',5,7-Tetrahydroxyflavanone	OC1=CC=C(C=C1)C1(O)CC(=O)C2=C(O)C=C(O)C=C2O1	2948.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2,4',5,7-Tetrahydroxyflavanone,1TMS,isomer #1	C[Si](C)(C)OC1=CC=C(C2(O)CC(=O)C3=C(O)C=C(O)C=C3O2)C=C1	2936.2	Semi standard non polar	33892256
2,4',5,7-Tetrahydroxyflavanone,1TMS,isomer #2	C[Si](C)(C)OC1(C2=CC=C(O)C=C2)CC(=O)C2=C(O)C=C(O)C=C2O1	2876.2	Semi standard non polar	33892256
2,4',5,7-Tetrahydroxyflavanone,1TMS,isomer #3	C[Si](C)(C)OC1=CC(O)=CC2=C1C(=O)CC(O)(C1=CC=C(O)C=C1)O2	2912.1	Semi standard non polar	33892256
2,4',5,7-Tetrahydroxyflavanone,1TMS,isomer #4	C[Si](C)(C)OC1=CC(O)=C2C(=O)CC(O)(C3=CC=C(O)C=C3)OC2=C1	2897.1	Semi standard non polar	33892256
2,4',5,7-Tetrahydroxyflavanone,2TMS,isomer #1	C[Si](C)(C)OC1=CC=C(C2(O[Si](C)(C)C)CC(=O)C3=C(O)C=C(O)C=C3O2)C=C1	2876.0	Semi standard non polar	33892256
2,4',5,7-Tetrahydroxyflavanone,2TMS,isomer #2	C[Si](C)(C)OC1=CC=C(C2(O)CC(=O)C3=C(C=C(O)C=C3O[Si](C)(C)C)O2)C=C1	2877.1	Semi standard non polar	33892256
2,4',5,7-Tetrahydroxyflavanone,2TMS,isomer #3	C[Si](C)(C)OC1=CC=C(C2(O)CC(=O)C3=C(O)C=C(O[Si](C)(C)C)C=C3O2)C=C1	2897.0	Semi standard non polar	33892256
2,4',5,7-Tetrahydroxyflavanone,2TMS,isomer #4	C[Si](C)(C)OC1=CC(O)=CC2=C1C(=O)CC(O[Si](C)(C)C)(C1=CC=C(O)C=C1)O2	2894.0	Semi standard non polar	33892256
2,4',5,7-Tetrahydroxyflavanone,2TMS,isomer #5	C[Si](C)(C)OC1=CC(O)=C2C(=O)CC(O[Si](C)(C)C)(C3=CC=C(O)C=C3)OC2=C1	2828.7	Semi standard non polar	33892256
2,4',5,7-Tetrahydroxyflavanone,2TMS,isomer #6	C[Si](C)(C)OC1=CC2=C(C(=O)CC(O)(C3=CC=C(O)C=C3)O2)C(O[Si](C)(C)C)=C1	2838.8	Semi standard non polar	33892256
2,4',5,7-Tetrahydroxyflavanone,3TMS,isomer #1	C[Si](C)(C)OC1=CC=C(C2(O[Si](C)(C)C)CC(=O)C3=C(C=C(O)C=C3O[Si](C)(C)C)O2)C=C1	2851.6	Semi standard non polar	33892256
2,4',5,7-Tetrahydroxyflavanone,3TMS,isomer #2	C[Si](C)(C)OC1=CC=C(C2(O[Si](C)(C)C)CC(=O)C3=C(O)C=C(O[Si](C)(C)C)C=C3O2)C=C1	2798.0	Semi standard non polar	33892256
2,4',5,7-Tetrahydroxyflavanone,3TMS,isomer #3	C[Si](C)(C)OC1=CC=C(C2(O)CC(=O)C3=C(C=C(O[Si](C)(C)C)C=C3O[Si](C)(C)C)O2)C=C1	2845.7	Semi standard non polar	33892256
2,4',5,7-Tetrahydroxyflavanone,3TMS,isomer #4	C[Si](C)(C)OC1=CC2=C(C(=O)CC(O[Si](C)(C)C)(C3=CC=C(O)C=C3)O2)C(O[Si](C)(C)C)=C1	2803.3	Semi standard non polar	33892256
2,4',5,7-Tetrahydroxyflavanone,4TMS,isomer #1	C[Si](C)(C)OC1=CC=C(C2(O[Si](C)(C)C)CC(=O)C3=C(C=C(O[Si](C)(C)C)C=C3O[Si](C)(C)C)O2)C=C1	2864.1	Semi standard non polar	33892256
2,4',5,7-Tetrahydroxyflavanone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(C2(O)CC(=O)C3=C(O)C=C(O)C=C3O2)C=C1	3234.3	Semi standard non polar	33892256
2,4',5,7-Tetrahydroxyflavanone,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1(C2=CC=C(O)C=C2)CC(=O)C2=C(O)C=C(O)C=C2O1	3142.6	Semi standard non polar	33892256
2,4',5,7-Tetrahydroxyflavanone,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC(O)=CC2=C1C(=O)CC(O)(C1=CC=C(O)C=C1)O2	3166.3	Semi standard non polar	33892256
2,4',5,7-Tetrahydroxyflavanone,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C(=O)CC(O)(C3=CC=C(O)C=C3)OC2=C1	3165.2	Semi standard non polar	33892256
2,4',5,7-Tetrahydroxyflavanone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(C2(O[Si](C)(C)C(C)(C)C)CC(=O)C3=C(O)C=C(O)C=C3O2)C=C1	3429.7	Semi standard non polar	33892256
2,4',5,7-Tetrahydroxyflavanone,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(C2(O)CC(=O)C3=C(C=C(O)C=C3O[Si](C)(C)C(C)(C)C)O2)C=C1	3412.1	Semi standard non polar	33892256
2,4',5,7-Tetrahydroxyflavanone,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=C(C2(O)CC(=O)C3=C(O)C=C(O[Si](C)(C)C(C)(C)C)C=C3O2)C=C1	3445.1	Semi standard non polar	33892256
2,4',5,7-Tetrahydroxyflavanone,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC(O)=CC2=C1C(=O)CC(O[Si](C)(C)C(C)(C)C)(C1=CC=C(O)C=C1)O2	3437.1	Semi standard non polar	33892256
2,4',5,7-Tetrahydroxyflavanone,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C(=O)CC(O[Si](C)(C)C(C)(C)C)(C3=CC=C(O)C=C3)OC2=C1	3356.1	Semi standard non polar	33892256
2,4',5,7-Tetrahydroxyflavanone,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC1=CC2=C(C(=O)CC(O)(C3=CC=C(O)C=C3)O2)C(O[Si](C)(C)C(C)(C)C)=C1	3369.5	Semi standard non polar	33892256
2,4',5,7-Tetrahydroxyflavanone,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(C2(O[Si](C)(C)C(C)(C)C)CC(=O)C3=C(C=C(O)C=C3O[Si](C)(C)C(C)(C)C)O2)C=C1	3606.9	Semi standard non polar	33892256
2,4',5,7-Tetrahydroxyflavanone,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(C2(O[Si](C)(C)C(C)(C)C)CC(=O)C3=C(O)C=C(O[Si](C)(C)C(C)(C)C)C=C3O2)C=C1	3598.3	Semi standard non polar	33892256
2,4',5,7-Tetrahydroxyflavanone,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=C(C2(O)CC(=O)C3=C(C=C(O[Si](C)(C)C(C)(C)C)C=C3O[Si](C)(C)C(C)(C)C)O2)C=C1	3574.4	Semi standard non polar	33892256
2,4',5,7-Tetrahydroxyflavanone,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC2=C(C(=O)CC(O[Si](C)(C)C(C)(C)C)(C3=CC=C(O)C=C3)O2)C(O[Si](C)(C)C(C)(C)C)=C1	3511.0	Semi standard non polar	33892256
2,4',5,7-Tetrahydroxyflavanone,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(C2(O[Si](C)(C)C(C)(C)C)CC(=O)C3=C(C=C(O[Si](C)(C)C(C)(C)C)C=C3O[Si](C)(C)C(C)(C)C)O2)C=C1	3734.5	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 - 2,4',5,7-Tetrahydroxyflavanone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fe3-4950000000-88836b86ebf787ff0002	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,4',5,7-Tetrahydroxyflavanone GC-MS (4 TMS) - 70eV, Positive	splash10-0jb9-5570190000-34397f547b6ebb61f276	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,4',5,7-Tetrahydroxyflavanone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,4',5,7-Tetrahydroxyflavanone 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 - 2,4',5,7-Tetrahydroxyflavanone 10V, Positive-QTOF	splash10-000i-0190000000-ae92d62d1526905bb962	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4',5,7-Tetrahydroxyflavanone 20V, Positive-QTOF	splash10-000i-0490000000-3b3bfa31061f70647494	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4',5,7-Tetrahydroxyflavanone 40V, Positive-QTOF	splash10-0udi-9700000000-2da5164126c4652f3494	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4',5,7-Tetrahydroxyflavanone 10V, Negative-QTOF	splash10-000i-0090000000-a27730caec7dfe2a595b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4',5,7-Tetrahydroxyflavanone 20V, Negative-QTOF	splash10-000i-1590000000-1e35b29f9497386c700b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4',5,7-Tetrahydroxyflavanone 40V, Negative-QTOF	splash10-0f76-6910000000-a89ad9617414b47b135a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4',5,7-Tetrahydroxyflavanone 10V, Positive-QTOF	splash10-000i-0090000000-6ba2690e52ef797ececb	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4',5,7-Tetrahydroxyflavanone 20V, Positive-QTOF	splash10-0w2i-0940000000-1c597880cc933f28961b	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4',5,7-Tetrahydroxyflavanone 40V, Positive-QTOF	splash10-0udi-0900000000-f654b2d40f1345d75b29	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4',5,7-Tetrahydroxyflavanone 10V, Negative-QTOF	splash10-000i-0090000000-fd96bbe1d8ed2e3ede5b	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4',5,7-Tetrahydroxyflavanone 20V, Negative-QTOF	splash10-0f79-0980000000-c6bfd4913da1e44ef31d	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4',5,7-Tetrahydroxyflavanone 40V, Negative-QTOF	splash10-000i-0900000000-8d4818271eab4b80a22f	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

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

FDB020037

KNApSAcK ID

C00054563

Chemspider ID

10686367

KEGG Compound ID

Not Available

BioCyc ID

CPD-15074

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21932272

PDB ID

Not Available

ChEBI ID

142230

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1882601

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 2,4',5,7-Tetrahydroxyflavanone (HMDB0040314)

MOL for HMDB0040314 (2,4',5,7-Tetrahydroxyflavanone)

3D MOL for HMDB0040314 (2,4',5,7-Tetrahydroxyflavanone)

3D SDF for HMDB0040314 (2,4',5,7-Tetrahydroxyflavanone)

3D-SDF for HMDB0040314 (2,4',5,7-Tetrahydroxyflavanone)

PDB for HMDB0040314 (2,4',5,7-Tetrahydroxyflavanone)

3D PDB for HMDB0040314 (2,4',5,7-Tetrahydroxyflavanone)

SMILES for HMDB0040314 (2,4',5,7-Tetrahydroxyflavanone)

INCHI for HMDB0040314 (2,4',5,7-Tetrahydroxyflavanone)

Structure for HMDB0040314 (2,4',5,7-Tetrahydroxyflavanone)

3D Structure for HMDB0040314 (2,4',5,7-Tetrahydroxyflavanone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra