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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2) Show 2 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:45:42 UTC

Update Date

2022-03-07 02:53:08 UTC

HMDB ID

HMDB0031824

Secondary Accession Numbers

HMDB31824

Metabolite Identification

Common Name

4',5,8-Trihydroxyflavanone

Description

4',5,8-Trihydroxyflavanone belongs to the class of organic compounds known as flavanones. Flavanones are compounds containing a flavan-3-one moiety, with a structure characterized by a 2-phenyl-3,4-dihydro-2H-1-benzopyran bearing a ketone at the carbon C3. Thus, 4',5,8-trihydroxyflavanone is considered to be a flavonoid. 4',5,8-Trihydroxyflavanone has been detected, but not quantified in, green vegetables and spinaches (Spinacia oleracea). This could make 4',5,8-trihydroxyflavanone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 4',5,8-Trihydroxyflavanone.

Structure

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

HMDB0031824
     RDKit          3D
4',5,8-Trihydroxyflavanone
 32 34  0  0  0  0  0  0  0  0999 V2000
   -1.9696    2.6474    1.0911 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5144    1.7112    0.4097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1257    1.6351   -0.1243 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3999    0.2777    0.3531 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8347    0.1343    0.1098 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3372   -0.2337   -1.1208 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6978   -0.3619   -1.3243 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6042   -0.1283   -0.3099 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9796   -0.2640   -0.5376 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1061    0.2400    0.9226 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7445    0.3666    1.1202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3676   -0.7759   -0.1776 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7484   -0.6385   -0.1962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5255   -1.7615   -0.5107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8930   -2.9814   -0.7956 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8966   -1.6646   -0.5388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4936   -0.4607   -0.2568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7424    0.6775    0.0603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3929    1.8346    0.3269 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3900    0.5658    0.0843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1101    1.7071   -1.2215 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5372    2.3942    0.3541 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2270    0.2937    1.4678 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6768   -0.4325   -1.9629 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0908   -0.6545   -2.3039 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3454   -1.2049   -0.3563 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8329    0.4192    1.7068 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4167    0.6611    2.1190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4757   -3.7759   -1.0193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5112   -2.5443   -0.7852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5727   -0.4223   -0.2885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1013    2.7394    0.5585 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
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
  4 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 20  2  1  0
 11  5  1  0
 20 13  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  6 24  1  0
  7 25  1  0
  9 26  1  0
 10 27  1  0
 11 28  1  0
 15 29  1  0
 16 30  1  0
 17 31  1  0
 19 32  1  0
M  END


  Mrv0541 05061306092D          

 20 22  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    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    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
    5.0013   -0.4125    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
    2.1434    1.2375    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
    3.5724    1.2375    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
    2.8579    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
    7.1447   -1.6500    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
    2.1434   -1.2375    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
    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
  6  5  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  1  0  0  0  0
 11  6  1  0  0  0  0
 12  7  1  0  0  0  0
 13  7  1  0  0  0  0
 13  8  1  0  0  0  0
 14 10  2  0  0  0  0
 14 12  1  0  0  0  0
 15 11  2  0  0  0  0
 15 14  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 13  1  0  0  0  0
 20 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0031824

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=CC=C(C=C1)C1CC(=O)C2=C(O)C=CC(O)=C2O1

> <INCHI_IDENTIFIER>
InChI=1S/C15H12O5/c16-9-3-1-8(2-4-9)13-7-12(19)14-10(17)5-6-11(18)15(14)20-13/h1-6,13,16-18H,7H2

> <INCHI_KEY>
SMRHIFAZRRVAQZ-UHFFFAOYSA-N

> <FORMULA>
C15H12O5

> <MOLECULAR_WEIGHT>
272.2528

> <EXACT_MASS>
272.068473494

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
27.16110562996326

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,8-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one

> <ALOGPS_LOGP>
2.47

> <JCHEM_LOGP>
2.835108050333333

> <ALOGPS_LOGS>
-3.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.985223598907567

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.31357769798091

> <JCHEM_PKA_STRONGEST_BASIC>
-4.074339405056507

> <JCHEM_POLAR_SURFACE_AREA>
86.99

> <JCHEM_REFRACTIVITY>
71.28980000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.43e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,8-dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzopyran-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0031824
     RDKit          3D
4',5,8-Trihydroxyflavanone
 32 34  0  0  0  0  0  0  0  0999 V2000
   -1.9696    2.6474    1.0911 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5144    1.7112    0.4097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1257    1.6351   -0.1243 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3999    0.2777    0.3531 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8347    0.1343    0.1098 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3372   -0.2337   -1.1208 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6978   -0.3619   -1.3243 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6042   -0.1283   -0.3099 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9796   -0.2640   -0.5376 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1061    0.2400    0.9226 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7445    0.3666    1.1202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3676   -0.7759   -0.1776 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7484   -0.6385   -0.1962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5255   -1.7615   -0.5107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8930   -2.9814   -0.7956 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8966   -1.6646   -0.5388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4936   -0.4607   -0.2568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7424    0.6775    0.0603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3929    1.8346    0.3269 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3900    0.5658    0.0843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1101    1.7071   -1.2215 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5372    2.3942    0.3541 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2270    0.2937    1.4678 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6768   -0.4325   -1.9629 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0908   -0.6545   -2.3039 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3454   -1.2049   -0.3563 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8329    0.4192    1.7068 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4167    0.6611    2.1190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4757   -3.7759   -1.0193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5112   -2.5443   -0.7852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5727   -0.4223   -0.2885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1013    2.7394    0.5585 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
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
  4 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 20  2  1  0
 11  5  1  0
 20 13  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  6 24  1  0
  7 25  1  0
  9 26  1  0
 10 27  1  0
 11 28  1  0
 15 29  1  0
 16 30  1  0
 17 31  1  0
 19 32  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   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.003  -0.770   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       2.667   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       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001  -0.770   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       8.002   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       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      13.337  -3.080   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       4.001  -2.310   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       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    6   10                                                       
CONECT    6    5   11                                                       
CONECT    7   12   13                                                       
CONECT    8    1    2   13                                                  
CONECT    9    3    4   16                                                  
CONECT   10    5   14   17                                                  
CONECT   11    6   15   18                                                  
CONECT   12    7   14   19                                                  
CONECT   13    7    8   20                                                  
CONECT   14   10   12   15                                                  
CONECT   15   11   14   20                                                  
CONECT   16    9                                                            
CONECT   17   10                                                            
CONECT   18   11                                                            
CONECT   19   12                                                            
CONECT   20   13   15                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

COMPND    HMDB0031824
HETATM    1  O1  UNL     1      -1.970   2.647   1.091  1.00  0.00           O  
HETATM    2  C1  UNL     1      -1.514   1.711   0.410  1.00  0.00           C  
HETATM    3  C2  UNL     1      -0.126   1.635  -0.124  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.400   0.278   0.353  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.835   0.134   0.110  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.337  -0.234  -1.121  1.00  0.00           C  
HETATM    7  C6  UNL     1       3.698  -0.362  -1.324  1.00  0.00           C  
HETATM    8  C7  UNL     1       4.604  -0.128  -0.310  1.00  0.00           C  
HETATM    9  O2  UNL     1       5.980  -0.264  -0.538  1.00  0.00           O  
HETATM   10  C8  UNL     1       4.106   0.240   0.923  1.00  0.00           C  
HETATM   11  C9  UNL     1       2.744   0.367   1.120  1.00  0.00           C  
HETATM   12  O3  UNL     1      -0.368  -0.776  -0.178  1.00  0.00           O  
HETATM   13  C10 UNL     1      -1.748  -0.639  -0.196  1.00  0.00           C  
HETATM   14  C11 UNL     1      -2.526  -1.762  -0.511  1.00  0.00           C  
HETATM   15  O4  UNL     1      -1.893  -2.981  -0.796  1.00  0.00           O  
HETATM   16  C12 UNL     1      -3.897  -1.665  -0.539  1.00  0.00           C  
HETATM   17  C13 UNL     1      -4.494  -0.461  -0.257  1.00  0.00           C  
HETATM   18  C14 UNL     1      -3.742   0.677   0.060  1.00  0.00           C  
HETATM   19  O5  UNL     1      -4.393   1.835   0.327  1.00  0.00           O  
HETATM   20  C15 UNL     1      -2.390   0.566   0.084  1.00  0.00           C  
HETATM   21  H1  UNL     1      -0.110   1.707  -1.222  1.00  0.00           H  
HETATM   22  H2  UNL     1       0.537   2.394   0.354  1.00  0.00           H  
HETATM   23  H3  UNL     1       0.227   0.294   1.468  1.00  0.00           H  
HETATM   24  H4  UNL     1       1.677  -0.432  -1.963  1.00  0.00           H  
HETATM   25  H5  UNL     1       4.091  -0.654  -2.304  1.00  0.00           H  
HETATM   26  H6  UNL     1       6.345  -1.205  -0.356  1.00  0.00           H  
HETATM   27  H7  UNL     1       4.833   0.419   1.707  1.00  0.00           H  
HETATM   28  H8  UNL     1       2.417   0.661   2.119  1.00  0.00           H  
HETATM   29  H9  UNL     1      -2.476  -3.776  -1.019  1.00  0.00           H  
HETATM   30  H10 UNL     1      -4.511  -2.544  -0.785  1.00  0.00           H  
HETATM   31  H11 UNL     1      -5.573  -0.422  -0.288  1.00  0.00           H  
HETATM   32  H12 UNL     1      -4.101   2.739   0.559  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   20
CONECT    3    4   21   22
CONECT    4    5   12   23
CONECT    5    6    6   11
CONECT    6    7   24
CONECT    7    8    8   25
CONECT    8    9   10
CONECT    9   26
CONECT   10   11   11   27
CONECT   11   28
CONECT   12   13
CONECT   13   14   14   20
CONECT   14   15   16
CONECT   15   29
CONECT   16   17   17   30
CONECT   17   18   31
CONECT   18   19   20   20
CONECT   19   32
END

HMDB0031824
     RDKit          3D
4',5,8-Trihydroxyflavanone
 32 34  0  0  0  0  0  0  0  0999 V2000
   -1.9696    2.6474    1.0911 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5144    1.7112    0.4097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1257    1.6351   -0.1243 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3999    0.2777    0.3531 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8347    0.1343    0.1098 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3372   -0.2337   -1.1208 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6978   -0.3619   -1.3243 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6042   -0.1283   -0.3099 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9796   -0.2640   -0.5376 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1061    0.2400    0.9226 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7445    0.3666    1.1202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3676   -0.7759   -0.1776 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7484   -0.6385   -0.1962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5255   -1.7615   -0.5107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8930   -2.9814   -0.7956 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8966   -1.6646   -0.5388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4936   -0.4607   -0.2568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7424    0.6775    0.0603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3929    1.8346    0.3269 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3900    0.5658    0.0843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1101    1.7071   -1.2215 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5372    2.3942    0.3541 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2270    0.2937    1.4678 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6768   -0.4325   -1.9629 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0908   -0.6545   -2.3039 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3454   -1.2049   -0.3563 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8329    0.4192    1.7068 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4167    0.6611    2.1190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4757   -3.7759   -1.0193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5112   -2.5443   -0.7852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5727   -0.4223   -0.2885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1013    2.7394    0.5585 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
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
  4 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 20  2  1  0
 11  5  1  0
 20 13  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  6 24  1  0
  7 25  1  0
  9 26  1  0
 10 27  1  0
 11 28  1  0
 15 29  1  0
 16 30  1  0
 17 31  1  0
 19 32  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-Ethyl-7-(trifluoromethyl)-2-quinoxalinol	HMDB
5,8,4'-Trihydroxyflavanone	HMDB
7-Trifluoromethyl-3-ethyl-2(1H)-quinoxalinone	HMDB

Chemical Formula

C₁₅H₁₂O₅

Average Molecular Weight

272.2528

Monoisotopic Molecular Weight

272.068473494

IUPAC Name

5,8-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one

Traditional Name

5,8-dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzopyran-4-one

CAS Registry Number

123067-25-4

SMILES

OC1=CC=C(C=C1)C1CC(=O)C2=C(O)C=CC(O)=C2O1

InChI Identifier

InChI=1S/C15H12O5/c16-9-3-1-8(2-4-9)13-7-12(19)14-10(17)5-6-11(18)15(14)20-13/h1-6,13,16-18H,7H2

InChI Key

SMRHIFAZRRVAQZ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavanones. Flavanones are compounds containing a flavan-3-one moiety, with a structure characterized by a 2-phenyl-3,4-dihydro-2H-1-benzopyran bearing a ketone at the carbon C3.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavans

Direct Parent

Flavanones

Alternative Parents

Substituents

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Flavanones (LMPK12140104 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0031824)
Cytoplasm (HMDB: HMDB0031824)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0031824)

Source

Endogenous

Endogenous (HMDB: HMDB0031824)

Plant

Plant (HMDB: HMDB0031824)

Exogenous

Food

Food (HMDB: HMDB0031824)

Vegetable

Leaf vegetable

Spinach (FooDB: FOOD00178)
Green vegetables (FooDB: FOOD00872)

Exogenous (HMDB: HMDB0031824)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	262 - 264 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	395.9 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	0.24 g/L	ALOGPS
logP	2.47	ALOGPS
logP	2.84	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	9.31	ChemAxon
pKa (Strongest Basic)	-4.1	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	1	ChemAxon
Refractivity	71.29 m³·mol⁻¹	ChemAxon
Polarizability	27.16 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]+	163.025	31661259
DarkChem	[M-H]-	162.316	31661259
DeepCCS	[M+H]+	163.199	30932474
DeepCCS	[M-H]-	160.841	30932474
DeepCCS	[M-2H]-	193.727	30932474
DeepCCS	[M+Na]+	169.292	30932474
AllCCS	[M+H]+	163.1	32859911
AllCCS	[M+H-H2O]+	159.2	32859911
AllCCS	[M+NH4]+	166.7	32859911
AllCCS	[M+Na]+	167.7	32859911
AllCCS	[M-H]-	162.9	32859911
AllCCS	[M+Na-2H]-	162.3	32859911
AllCCS	[M+HCOO]-	161.7	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022.	5.98 minutes	32390414
Predicted by Siyang on May 30, 2022	11.9943 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.65 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2031.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	287.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	146.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	170.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	248.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	587.1 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	548.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	96.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1000.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	414.0 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1305.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	369.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	365.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	498.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	244.5 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	152.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4',5,8-Trihydroxyflavanone	OC1=CC=C(C=C1)C1CC(=O)C2=C(O)C=CC(O)=C2O1	3874.4	Standard polar	33892256
4',5,8-Trihydroxyflavanone	OC1=CC=C(C=C1)C1CC(=O)C2=C(O)C=CC(O)=C2O1	2818.3	Standard non polar	33892256
4',5,8-Trihydroxyflavanone	OC1=CC=C(C=C1)C1CC(=O)C2=C(O)C=CC(O)=C2O1	2729.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4',5,8-Trihydroxyflavanone,1TMS,isomer #1	C[Si](C)(C)OC1=CC=C(C2CC(=O)C3=C(O)C=CC(O)=C3O2)C=C1	2784.5	Semi standard non polar	33892256
4',5,8-Trihydroxyflavanone,1TMS,isomer #2	C[Si](C)(C)OC1=CC=C(O)C2=C1C(=O)CC(C1=CC=C(O)C=C1)O2	2794.4	Semi standard non polar	33892256
4',5,8-Trihydroxyflavanone,1TMS,isomer #3	C[Si](C)(C)OC1=CC=C(O)C2=C1OC(C1=CC=C(O)C=C1)CC2=O	2779.7	Semi standard non polar	33892256
4',5,8-Trihydroxyflavanone,2TMS,isomer #1	C[Si](C)(C)OC1=CC=C(C2CC(=O)C3=C(O[Si](C)(C)C)C=CC(O)=C3O2)C=C1	2803.2	Semi standard non polar	33892256
4',5,8-Trihydroxyflavanone,2TMS,isomer #2	C[Si](C)(C)OC1=CC=C(C2CC(=O)C3=C(O)C=CC(O[Si](C)(C)C)=C3O2)C=C1	2801.0	Semi standard non polar	33892256
4',5,8-Trihydroxyflavanone,2TMS,isomer #3	C[Si](C)(C)OC1=CC=C(O[Si](C)(C)C)C2=C1OC(C1=CC=C(O)C=C1)CC2=O	2791.7	Semi standard non polar	33892256
4',5,8-Trihydroxyflavanone,3TMS,isomer #1	C[Si](C)(C)OC1=CC=C(C2CC(=O)C3=C(O[Si](C)(C)C)C=CC(O[Si](C)(C)C)=C3O2)C=C1	2807.6	Semi standard non polar	33892256
4',5,8-Trihydroxyflavanone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(C2CC(=O)C3=C(O)C=CC(O)=C3O2)C=C1	3048.4	Semi standard non polar	33892256
4',5,8-Trihydroxyflavanone,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(O)C2=C1C(=O)CC(C1=CC=C(O)C=C1)O2	3060.2	Semi standard non polar	33892256
4',5,8-Trihydroxyflavanone,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=C(O)C2=C1OC(C1=CC=C(O)C=C1)CC2=O	3049.8	Semi standard non polar	33892256
4',5,8-Trihydroxyflavanone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(C2CC(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=CC(O)=C3O2)C=C1	3305.0	Semi standard non polar	33892256
4',5,8-Trihydroxyflavanone,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(C2CC(=O)C3=C(O)C=CC(O[Si](C)(C)C(C)(C)C)=C3O2)C=C1	3287.1	Semi standard non polar	33892256
4',5,8-Trihydroxyflavanone,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=C(O[Si](C)(C)C(C)(C)C)C2=C1OC(C1=CC=C(O)C=C1)CC2=O	3295.3	Semi standard non polar	33892256
4',5,8-Trihydroxyflavanone,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(C2CC(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=CC(O[Si](C)(C)C(C)(C)C)=C3O2)C=C1	3488.5	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 - 4',5,8-Trihydroxyflavanone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-1490000000-aab471b5b64975003a77	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4',5,8-Trihydroxyflavanone GC-MS (3 TMS) - 70eV, Positive	splash10-00b9-4922800000-e9d3f8c5da94bb79f83d	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4',5,8-Trihydroxyflavanone 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 - 4',5,8-Trihydroxyflavanone 10V, Positive-QTOF	splash10-00di-0490000000-8a4c8b1f1cd45bd9d4df	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4',5,8-Trihydroxyflavanone 20V, Positive-QTOF	splash10-0kmi-0940000000-9146002fb44ad2244f02	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4',5,8-Trihydroxyflavanone 40V, Positive-QTOF	splash10-00xr-5900000000-45605c8fb550165fb120	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4',5,8-Trihydroxyflavanone 10V, Negative-QTOF	splash10-00di-0190000000-b84e11e4da85266bccd2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4',5,8-Trihydroxyflavanone 20V, Negative-QTOF	splash10-00di-0890000000-e304ea692b0c5c88d10f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4',5,8-Trihydroxyflavanone 40V, Negative-QTOF	splash10-0ap3-4900000000-ea6204221e8823753012	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4',5,8-Trihydroxyflavanone 10V, Negative-QTOF	splash10-00di-0090000000-ef3c85d68f246f25c912	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4',5,8-Trihydroxyflavanone 20V, Negative-QTOF	splash10-0fk9-0790000000-a386e8bbaa9ae30462a0	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4',5,8-Trihydroxyflavanone 40V, Negative-QTOF	splash10-014i-0900000000-09d69c292a81834ed9bb	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4',5,8-Trihydroxyflavanone 10V, Positive-QTOF	splash10-00di-0090000000-105ebbdeec4c9fc3ae6f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4',5,8-Trihydroxyflavanone 20V, Positive-QTOF	splash10-0uka-0940000000-c743726bc2bdef6b6f00	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4',5,8-Trihydroxyflavanone 40V, Positive-QTOF	splash10-0udi-0900000000-c4390b819362ba19dc35	2021-09-24	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

FDB008502

KNApSAcK ID

C00008392

Chemspider ID

24846274

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14353343

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1828131

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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

Enzymes

Enzyme Details

1. UDP-glucuronosyltransferase 1-1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:: UGT1A1
Uniprot ID:: P22309
Molecular weight:: 59590.91

Reactions

4',5,8-Trihydroxyflavanone → 3,4,5-trihydroxy-6-{[8-hydroxy-2-(4-hydroxyphenyl)-4-oxo-3,4-dihydro-2H-1-benzopyran-5-yl]oxy}oxane-2-carboxylic acid	details
4',5,8-Trihydroxyflavanone → 6-[4-(5,8-dihydroxy-4-oxo-3,4-dihydro-2H-1-benzopyran-2-yl)phenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid	details

Enzyme Details

2. Sulfotransferase 1A3

General function:: sulfotransferase activity
Specific function:: Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:: SULT1A3
Uniprot ID:: P0DMM9
Molecular weight:: 34195.96

Reactions

4',5,8-Trihydroxyflavanone → [4-(5,8-dihydroxy-4-oxo-3,4-dihydro-2H-1-benzopyran-2-yl)phenyl]oxidanesulfonic acid	details

Showing metabocard for 4',5,8-Trihydroxyflavanone (HMDB0031824)

MOL for HMDB0031824 (4',5,8-Trihydroxyflavanone)

3D MOL for HMDB0031824 (4',5,8-Trihydroxyflavanone)

3D SDF for HMDB0031824 (4',5,8-Trihydroxyflavanone)

3D-SDF for HMDB0031824 (4',5,8-Trihydroxyflavanone)

PDB for HMDB0031824 (4',5,8-Trihydroxyflavanone)

3D PDB for HMDB0031824 (4',5,8-Trihydroxyflavanone)

SMILES for HMDB0031824 (4',5,8-Trihydroxyflavanone)

INCHI for HMDB0031824 (4',5,8-Trihydroxyflavanone)

Structure for HMDB0031824 (4',5,8-Trihydroxyflavanone)

3D Structure for HMDB0031824 (4',5,8-Trihydroxyflavanone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions

Reactions