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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:46:49 UTC

Update Date

2022-03-07 02:54:59 UTC

HMDB ID

HMDB0036619

Secondary Accession Numbers

HMDB36619

Metabolite Identification

Common Name

5,7-Dihydroxyflavone

Description

5,7-Dihydroxyflavone belongs to the class of organic compounds known as flavones. These are flavonoids with a structure based on the backbone of 2-phenylchromen-4-one (2-phenyl-1-benzopyran-4-one). Thus, 5,7-dihydroxyflavone is considered to be a flavonoid. 5,7-Dihydroxyflavone is a bitter tasting compound. 5,7-Dihydroxyflavone has been detected, but not quantified in, several different foods, such as carrots (Daucus carota ssp. sativus), sour cherries (Prunus cerasus), sweet oranges (Citrus sinensis), and wild carrots (Daucus carota). This could make 5,7-dihydroxyflavone a potential biomarker for the consumption of these foods. 5,7-Dihydroxyflavone is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on 5,7-Dihydroxyflavone.

Structure

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

HMDB0036619
     RDKit          3D
5,7-Dihydroxyflavone
 29 31  0  0  0  0  0  0  0  0999 V2000
   -1.3485   -3.1107   -0.1892 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9938   -1.8999   -0.1379 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3457   -1.5705   -0.0521 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7584   -0.2791    0.0046 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1879    0.0990    0.0969 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5008    1.4442    0.1491 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8292    1.7908    0.2348 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8536    0.8731    0.2707 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5270   -0.4618    0.2179 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1732   -0.8196    0.1305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1394    0.6689   -0.0233 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4162    0.4031   -0.1039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3497    1.4371   -0.1316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7039    1.2386   -0.2150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5767    2.3437   -0.2374 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1772   -0.0420   -0.2749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2845   -1.1406   -0.2511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8057   -2.3887   -0.3130 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9306   -0.8974   -0.1667 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0566   -2.3993   -0.0320 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7185    2.1840    0.1227 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1183    2.8473    0.2783 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9059    1.1862    0.3395 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2931   -1.2132    0.2431 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9592   -1.8863    0.0910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9442    2.4378   -0.0827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8908    2.6496    0.6861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2445   -0.2329   -0.3415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4216   -3.2615   -0.3129 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
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  4 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 19  2  1  0
 10  5  1  0
 19 12  1  0
  3 20  1  0
  6 21  1  0
  7 22  1  0
  8 23  1  0
  9 24  1  0
 10 25  1  0
 13 26  1  0
 15 27  1  0
 16 28  1  0
 18 29  1  0
M  END

  Mrv0541 05061309142D          

 19 21  0  0  0  0            999 V2000
    6.4302   -1.2375    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
    5.7158   -1.6500    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
    5.0013   -1.2375    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
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    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
    4.2868    0.0000    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
    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
    3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  2  0  0  0  0
  9  4  2  0  0  0  0
  9  5  1  0  0  0  0
 10  6  2  0  0  0  0
 10  7  1  0  0  0  0
 11  6  1  0  0  0  0
 12  8  1  0  0  0  0
 13  8  2  0  0  0  0
 13  9  1  0  0  0  0
 14  7  2  0  0  0  0
 15 11  2  0  0  0  0
 15 12  1  0  0  0  0
 15 14  1  0  0  0  0
 16 10  1  0  0  0  0
 17 11  1  0  0  0  0
 18 12  2  0  0  0  0
 19 13  1  0  0  0  0
 19 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036619

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=CC(O)=C2C(=O)C=C(OC2=C1)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H10O4/c16-10-6-11(17)15-12(18)8-13(19-14(15)7-10)9-4-2-1-3-5-9/h1-8,16-17H

> <INCHI_KEY>
RTIXKCRFFJGDFG-UHFFFAOYSA-N

> <FORMULA>
C15H10O4

> <MOLECULAR_WEIGHT>
254.2375

> <EXACT_MASS>
254.057908808

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
25.72774514973364

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,7-dihydroxy-2-phenyl-4H-chromen-4-one

> <ALOGPS_LOGP>
3.44

> <JCHEM_LOGP>
3.010254455333333

> <ALOGPS_LOGS>
-3.38

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.320353557909437

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.637868205362397

> <JCHEM_PKA_STRONGEST_BASIC>
-5.174527093098605

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
70.933

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.05e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
chrysin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0036619
     RDKit          3D
5,7-Dihydroxyflavone
 29 31  0  0  0  0  0  0  0  0999 V2000
   -1.3485   -3.1107   -0.1892 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9938   -1.8999   -0.1379 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3457   -1.5705   -0.0521 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7584   -0.2791    0.0046 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1879    0.0990    0.0969 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5008    1.4442    0.1491 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8292    1.7908    0.2348 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8536    0.8731    0.2707 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5270   -0.4618    0.2179 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1732   -0.8196    0.1305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1394    0.6689   -0.0233 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4162    0.4031   -0.1039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3497    1.4371   -0.1316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7039    1.2386   -0.2150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5767    2.3437   -0.2374 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1772   -0.0420   -0.2749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2845   -1.1406   -0.2511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8057   -2.3887   -0.3130 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9306   -0.8974   -0.1667 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0566   -2.3993   -0.0320 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7185    2.1840    0.1227 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1183    2.8473    0.2783 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9059    1.1862    0.3395 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2931   -1.2132    0.2431 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9592   -1.8863    0.0910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9442    2.4378   -0.0827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8908    2.6496    0.6861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2445   -0.2329   -0.3415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4216   -3.2615   -0.3129 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
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  4 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 19  2  1  0
 10  5  1  0
 19 12  1  0
  3 20  1  0
  6 21  1  0
  7 22  1  0
  8 23  1  0
  9 24  1  0
 10 25  1  0
 13 26  1  0
 15 27  1  0
 16 28  1  0
 18 29  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.003  -0.770   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      10.669   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.336  -0.770   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       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       1.334  -0.770   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       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2    9                                                       
CONECT    5    3    9                                                       
CONECT    6   10   11                                                       
CONECT    7   10   14                                                       
CONECT    8   12   13                                                       
CONECT    9    4    5   13                                                  
CONECT   10    6    7   16                                                  
CONECT   11    6   15   17                                                  
CONECT   12    8   15   18                                                  
CONECT   13    8    9   19                                                  
CONECT   14    7   15   19                                                  
CONECT   15   11   12   14                                                  
CONECT   16   10                                                            
CONECT   17   11                                                            
CONECT   18   12                                                            
CONECT   19   13   14                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

COMPND    HMDB0036619
HETATM    1  O1  UNL     1      -1.349  -3.111  -0.189  1.00  0.00           O  
HETATM    2  C1  UNL     1      -0.994  -1.900  -0.138  1.00  0.00           C  
HETATM    3  C2  UNL     1       0.346  -1.570  -0.052  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.758  -0.279   0.005  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.188   0.099   0.097  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.501   1.444   0.149  1.00  0.00           C  
HETATM    7  C6  UNL     1       3.829   1.791   0.235  1.00  0.00           C  
HETATM    8  C7  UNL     1       4.854   0.873   0.271  1.00  0.00           C  
HETATM    9  C8  UNL     1       4.527  -0.462   0.218  1.00  0.00           C  
HETATM   10  C9  UNL     1       3.173  -0.820   0.130  1.00  0.00           C  
HETATM   11  O2  UNL     1      -0.139   0.669  -0.023  1.00  0.00           O  
HETATM   12  C10 UNL     1      -1.416   0.403  -0.104  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.350   1.437  -0.132  1.00  0.00           C  
HETATM   14  C12 UNL     1      -3.704   1.239  -0.215  1.00  0.00           C  
HETATM   15  O3  UNL     1      -4.577   2.344  -0.237  1.00  0.00           O  
HETATM   16  C13 UNL     1      -4.177  -0.042  -0.275  1.00  0.00           C  
HETATM   17  C14 UNL     1      -3.285  -1.141  -0.251  1.00  0.00           C  
HETATM   18  O4  UNL     1      -3.806  -2.389  -0.313  1.00  0.00           O  
HETATM   19  C15 UNL     1      -1.931  -0.897  -0.167  1.00  0.00           C  
HETATM   20  H1  UNL     1       1.057  -2.399  -0.032  1.00  0.00           H  
HETATM   21  H2  UNL     1       1.719   2.184   0.123  1.00  0.00           H  
HETATM   22  H3  UNL     1       4.118   2.847   0.278  1.00  0.00           H  
HETATM   23  H4  UNL     1       5.906   1.186   0.339  1.00  0.00           H  
HETATM   24  H5  UNL     1       5.293  -1.213   0.243  1.00  0.00           H  
HETATM   25  H6  UNL     1       2.959  -1.886   0.091  1.00  0.00           H  
HETATM   26  H7  UNL     1      -1.944   2.438  -0.083  1.00  0.00           H  
HETATM   27  H8  UNL     1      -4.891   2.650   0.686  1.00  0.00           H  
HETATM   28  H9  UNL     1      -5.245  -0.233  -0.341  1.00  0.00           H  
HETATM   29  H10 UNL     1      -3.422  -3.262  -0.313  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   19
CONECT    3    4    4   20
CONECT    4    5   11
CONECT    5    6    6   10
CONECT    6    7   21
CONECT    7    8    8   22
CONECT    8    9   23
CONECT    9   10   10   24
CONECT   10   25
CONECT   11   12
CONECT   12   13   13   19
CONECT   13   14   26
CONECT   14   15   16   16
CONECT   15   27
CONECT   16   17   28
CONECT   17   18   19   19
CONECT   18   29
END

HMDB0036619
     RDKit          3D
5,7-Dihydroxyflavone
 29 31  0  0  0  0  0  0  0  0999 V2000
   -1.3485   -3.1107   -0.1892 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9938   -1.8999   -0.1379 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3457   -1.5705   -0.0521 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7584   -0.2791    0.0046 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1879    0.0990    0.0969 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5008    1.4442    0.1491 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8292    1.7908    0.2348 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8536    0.8731    0.2707 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5270   -0.4618    0.2179 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1732   -0.8196    0.1305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1394    0.6689   -0.0233 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4162    0.4031   -0.1039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3497    1.4371   -0.1316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7039    1.2386   -0.2150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5767    2.3437   -0.2374 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1772   -0.0420   -0.2749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2845   -1.1406   -0.2511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8057   -2.3887   -0.3130 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9306   -0.8974   -0.1667 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0566   -2.3993   -0.0320 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7185    2.1840    0.1227 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1183    2.8473    0.2783 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9059    1.1862    0.3395 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2931   -1.2132    0.2431 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9592   -1.8863    0.0910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9442    2.4378   -0.0827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8908    2.6496    0.6861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2445   -0.2329   -0.3415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4216   -3.2615   -0.3129 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
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  4 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 19  2  1  0
 10  5  1  0
 19 12  1  0
  3 20  1  0
  6 21  1  0
  7 22  1  0
  8 23  1  0
  9 24  1  0
 10 25  1  0
 13 26  1  0
 15 27  1  0
 16 28  1  0
 18 29  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
5,7-Dihydroxy-2-phenyl-4H-1-benzopyran-4-one	ChEBI
5,7-Dihydroxy-2-phenyl-4H-benzo(b)pyran-4-one	ChEBI
5,7-Dihydroxy-2-phenylchromen-4-one	ChEBI
5,7-Dihydroxyflavone	ChEBI
5,7-Dihydroxy-2-phenyl-4H-1-benzopyran-4-one, 9ci	HMDB
Chrysin	HMDB
Chrysinic acid	HMDB
Ois 3	HMDB
Chrysine	MeSH
5,7-Dihydroxy-flavone	MeSH

Chemical Formula

C₁₅H₁₀O₄

Average Molecular Weight

254.2375

Monoisotopic Molecular Weight

254.057908808

IUPAC Name

5,7-dihydroxy-2-phenyl-4H-chromen-4-one

Traditional Name

chrysin

CAS Registry Number

480-40-0

SMILES

OC1=CC(O)=C2C(=O)C=C(OC2=C1)C1=CC=CC=C1

InChI Identifier

InChI=1S/C15H10O4/c16-10-6-11(17)15-12(18)8-13(19-14(15)7-10)9-4-2-1-3-5-9/h1-8,16-17H

InChI Key

RTIXKCRFFJGDFG-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavones. These are flavonoids with a structure based on the backbone of 2-phenylchromen-4-one (2-phenyl-1-benzopyran-4-one).

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavones

Direct Parent

Flavones

Alternative Parents

Substituents

5-hydroxyflavonoid
7-hydroxyflavonoid
Flavone
Hydroxyflavonoid
Chromone
Benzopyran
1-benzopyran
1-hydroxy-2-unsubstituted benzenoid
Pyranone
1-hydroxy-4-unsubstituted benzenoid
Benzenoid
Pyran
Monocyclic benzene moiety
Vinylogous acid
Heteroaromatic compound
Organoheterocyclic compound
Oxacycle
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

dihydroxyflavone (CHEBI:75095 )
7-hydroxyflavonol (CHEBI:75095 )
flavones (C10028 )
Flavones and Flavonols (C10028 )
Flavones and Flavonols (LMPK12110189 )

Ontology

Physiological effect

Organoleptic effect

Taste

Bitter

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0036619)
Cell membrane (HMDB: HMDB0036619)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036619)

Source

Exogenous

Exogenous (HMDB: HMDB0036619)

Food

Food (HMDB: HMDB0036619)

Vegetable

Root vegetable

Carrot (FooDB: FOOD00245)
Wild carrot (FooDB: FOOD00072)

Fruit

Citrus

Sweet orange (FooDB: FOOD00057)

Drupe

Sour cherry (FooDB: FOOD00146)

Endogenous

Plant

Plant (HMDB: HMDB0036619)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0036619)
Antiangiogenic (HMDB: HMDB0036619)
Antiangiogenic (HMDB: HMDB0036619)
VEGF inhibitor (HMDB: HMDB0036619)
Anti aflatoxin (HMDB: HMDB0036619)
Anti aggregant (HMDB: HMDB0036619)
Anti bacillary (HMDB: HMDB0036619)
Anti bacterial (HMDB: HMDB0036619)
Anti convulsant (HMDB: HMDB0036619)
Anti-estrogenic (HMDB: HMDB0036619)
Anti gout (HMDB: HMDB0036619)
Anti herpetic (HMDB: HMDB0036619)
Anti HIV (HMDB: HMDB0036619)
Anti hypertensive (HMDB: HMDB0036619)
Anti leukemic (HMDB: HMDB0036619)
Anti multidrug resistance (HMDB: HMDB0036619)
Anti mutagenic (HMDB: HMDB0036619)
Anti proliferant (HMDB: HMDB0036619)
Anti salmonella (HMDB: HMDB0036619)
Anti shigellic (HMDB: HMDB0036619)
Anti spasmodic (HMDB: HMDB0036619)
Anti staphylococcic (HMDB: HMDB0036619)
Anti stress (HMDB: HMDB0036619)
Anti thrombic (HMDB: HMDB0036619)
Anxiolytic (HMDB: HMDB0036619)
Cytotoxic (HMDB: HMDB0036619)
DNA-protective (HMDB: HMDB0036619)
Estrogenic (HMDB: HMDB0036619)
Hypotensive (HMDB: HMDB0036619)
Hypouricemic (HMDB: HMDB0036619)
Mutagenic (HMDB: HMDB0036619)
Myorelaxant (HMDB: HMDB0036619)
Nitric-oxide-genic (HMDB: HMDB0036619)
Testosterogenic (HMDB: HMDB0036619)
Vasorelaxant (HMDB: HMDB0036619)

Modulator

Inhibitor

EC 1.14.14.14 (aromatase) inhibitor (HMDB: HMDB0036619)
EC 5.99.1.2 (DNA topoisomerase) inhibitor (HMDB: HMDB0036619)
EC 1.17.3.2 (xanthine oxidase) inhibitor (HMDB: HMDB0036619)
Caspase-3 inhibitor (HMDB: HMDB0036619)
Caspase-9 inhibitor (HMDB: HMDB0036619)

Enzyme inhibitor

Cytochrome-CYP1A1 inhibitor (HMDB: HMDB0036619)
ICAM-1 inhibitor (HMDB: HMDB0036619)
JNK inhibitor (HMDB: HMDB0036619)
Monoamine-oxidase inhibitor (HMDB: HMDB0036619)

Apoptotic (HMDB: HMDB0036619)

Industrial application

Manufacturing industry

Material processing agent

Solid material processing agent

Protective agent

Antioxidant (HMDB: HMDB0036619)
Antioxidant (HMDB: HMDB0036619)

Antiviral agent (HMDB: HMDB0036619)
Anti-allergic agent (HMDB: HMDB0036619)
Central nervous system depressant (HMDB: HMDB0036619)
Radiopharmaceutical (HMDB: HMDB0036619)
Vasodilator agent (HMDB: HMDB0036619)

Agriculture

Pesticide

Fungicide (HMDB: HMDB0036619)
Termitifuge (HMDB: HMDB0036619)

Pesticide (HMDB: HMDB0036619)

Pharmaceutical industry

Antineoplastic agent

Antitumor (HMDB: HMDB0036619)
Cancer preventive (HMDB: HMDB0036619)

Hepatoprotective (HMDB: HMDB0036619)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	285.50 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Boiling Point	491.91 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	84 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	3.520	The Good Scents Company Information System

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	151.684	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001433

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.1 g/L	ALOGPS
logP	3.44	ALOGPS
logP	3.01	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	6.64	ChemAxon
pKa (Strongest Basic)	-5.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	70.93 m³·mol⁻¹	ChemAxon
Polarizability	25.73 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
DeepCCS	[M+H]+	155.718	30932474
DeepCCS	[M-H]-	153.323	30932474
DeepCCS	[M-2H]-	186.207	30932474
DeepCCS	[M+Na]+	161.714	30932474
AllCCS	[M+H]+	156.8	32859911
AllCCS	[M+H-H2O]+	152.7	32859911
AllCCS	[M+NH4]+	160.7	32859911
AllCCS	[M+Na]+	161.8	32859911
AllCCS	[M-H]-	157.2	32859911
AllCCS	[M+Na-2H]-	156.4	32859911
AllCCS	[M+HCOO]-	155.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5,7-Dihydroxyflavone	OC1=CC(O)=C2C(=O)C=C(OC2=C1)C1=CC=CC=C1	3917.0	Standard polar	33892256
5,7-Dihydroxyflavone	OC1=CC(O)=C2C(=O)C=C(OC2=C1)C1=CC=CC=C1	2657.4	Standard non polar	33892256
5,7-Dihydroxyflavone	OC1=CC(O)=C2C(=O)C=C(OC2=C1)C1=CC=CC=C1	2707.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
5,7-Dihydroxyflavone,1TMS,isomer #1	C[Si](C)(C)OC1=CC(O)=C2C(=O)C=C(C3=CC=CC=C3)OC2=C1	2786.9	Semi standard non polar	33892256
5,7-Dihydroxyflavone,1TMS,isomer #2	C[Si](C)(C)OC1=CC(O)=CC2=C1C(=O)C=C(C1=CC=CC=C1)O2	2736.5	Semi standard non polar	33892256
5,7-Dihydroxyflavone,2TMS,isomer #1	C[Si](C)(C)OC1=CC(O[Si](C)(C)C)=C2C(=O)C=C(C3=CC=CC=C3)OC2=C1	2803.8	Semi standard non polar	33892256
5,7-Dihydroxyflavone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C(=O)C=C(C3=CC=CC=C3)OC2=C1	3046.4	Semi standard non polar	33892256
5,7-Dihydroxyflavone,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC(O)=CC2=C1C(=O)C=C(C1=CC=CC=C1)O2	3002.3	Semi standard non polar	33892256
5,7-Dihydroxyflavone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C=C(C3=CC=CC=C3)OC2=C1	3261.0	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 5,7-Dihydroxyflavone GC-MS (2 TMS)	splash10-001i-2839000000-d0964f24f611d1c14e95	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 5,7-Dihydroxyflavone GC-MS (Non-derivatized)	splash10-001i-2839000000-d0964f24f611d1c14e95	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 5,7-Dihydroxyflavone GC-EI-TOF (Non-derivatized)	splash10-001i-0619000000-53f48b2cf9bad74e8f65	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5,7-Dihydroxyflavone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udi-0690000000-b07283fbd904f2901dd6	2017-07-27	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5,7-Dihydroxyflavone GC-MS (2 TMS) - 70eV, Positive	splash10-00gi-4439000000-26a54787c8758b70201f	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5,7-Dihydroxyflavone 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5,7-Dihydroxyflavone ESI-TOF , Negative-QTOF	splash10-0002-0020900000-2dbcc5b06309066d63b5	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5,7-Dihydroxyflavone ESI-TOF 26V, Negative-QTOF	splash10-0udi-0290000000-bdd70471bc805c9009b2	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5,7-Dihydroxyflavone ESI-TOF 40V, Negative-QTOF	splash10-0fr6-0900000000-eee4ea35750adc10ef1b	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5,7-Dihydroxyflavone ESI-TOF , Negative-QTOF	splash10-0udi-0090000000-2f6b543a5679e285552a	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5,7-Dihydroxyflavone ESI-TOF 26V, Negative-QTOF	splash10-0udi-0290000000-bdd70471bc805c9009b2	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5,7-Dihydroxyflavone ESI-TOF 40V, Negative-QTOF	splash10-0fr6-0900000000-eee4ea35750adc10ef1b	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5,7-Dihydroxyflavone DI-ESI-qTof , Negative-QTOF	splash10-0udi-0490000000-554518d0a352f29f8093	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5,7-Dihydroxyflavone DI-ESI-qTof , Positive-QTOF	splash10-0zfr-0950000000-51b2794dec3e6f6eea6a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5,7-Dihydroxyflavone LC-ESI-QTOF , negative-QTOF	splash10-0udi-0090000000-9cc0f49937b1a8fa0b34	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5,7-Dihydroxyflavone LC-ESI-QTOF , negative-QTOF	splash10-0udi-0090000000-66cd77f4bd910deb0103	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5,7-Dihydroxyflavone LC-ESI-QTOF , negative-QTOF	splash10-0udi-0290000000-10a8a1236031b97efe7a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5,7-Dihydroxyflavone LC-ESI-QTOF , negative-QTOF	splash10-0fr6-0920000000-19bbcaf4a2423b2cb49d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5,7-Dihydroxyflavone LC-ESI-QTOF , negative-QTOF	splash10-014m-0900000000-200355de722ac7f96ef7	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5,7-Dihydroxyflavone LC-ESI-QTOF , negative-QTOF	splash10-0udi-0090000000-ac2af4316665e2509d89	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5,7-Dihydroxyflavone LC-ESI-QTOF , negative-QTOF	splash10-0udi-0190000000-8f5ac4706417c39a2d62	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5,7-Dihydroxyflavone LC-ESI-QTOF , negative-QTOF	splash10-0gbc-0900000000-d619653decf40895a511	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5,7-Dihydroxyflavone Linear Ion Trap , negative-QTOF	splash10-0a4i-0390000000-eb3159b6ffe6b7c816b2	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5,7-Dihydroxyflavone Linear Ion Trap , negative-QTOF	splash10-006t-3930000000-3775c8b9ef4bbb0cb352	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5,7-Dihydroxyflavone Linear Ion Trap , negative-QTOF	splash10-0udi-0090000000-c8b5dd372a2667398b01	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,7-Dihydroxyflavone 10V, Positive-QTOF	splash10-0a4i-0090000000-c8a1f1ae722a2b79308a	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,7-Dihydroxyflavone 20V, Positive-QTOF	splash10-0a4i-0090000000-191437b0a57325aec07a	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,7-Dihydroxyflavone 40V, Positive-QTOF	splash10-0udr-4950000000-f1f4abaafec11c500890	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,7-Dihydroxyflavone 10V, Negative-QTOF	splash10-0udi-0090000000-4c48fd26f99d65b20cd9	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,7-Dihydroxyflavone 20V, Negative-QTOF	splash10-0udi-0090000000-acfd169c302ecc539f58	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,7-Dihydroxyflavone 40V, Negative-QTOF	splash10-0udi-1940000000-98ef8f11854760675c83	2015-04-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Chrysin

METLIN ID

Not Available

PubChem Compound

5281607

PDB ID

Not Available

ChEBI ID

75095

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1229801

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

5,7-Dihydroxyflavone → 3,4,5-trihydroxy-6-[(5-hydroxy-4-oxo-2-phenyl-4H-chromen-7-yl)oxy]oxane-2-carboxylic acid	details
5,7-Dihydroxyflavone → 3,4,5-trihydroxy-6-[(7-hydroxy-4-oxo-2-phenyl-4H-chromen-5-yl)oxy]oxane-2-carboxylic acid	details

Showing metabocard for 5,7-Dihydroxyflavone (HMDB0036619)

MOL for HMDB0036619 (5,7-Dihydroxyflavone)

3D MOL for HMDB0036619 (5,7-Dihydroxyflavone)

3D SDF for HMDB0036619 (5,7-Dihydroxyflavone)

3D-SDF for HMDB0036619 (5,7-Dihydroxyflavone)

PDB for HMDB0036619 (5,7-Dihydroxyflavone)

3D PDB for HMDB0036619 (5,7-Dihydroxyflavone)

SMILES for HMDB0036619 (5,7-Dihydroxyflavone)

INCHI for HMDB0036619 (5,7-Dihydroxyflavone)

Structure for HMDB0036619 (5,7-Dihydroxyflavone)

3D Structure for HMDB0036619 (5,7-Dihydroxyflavone)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

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