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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:45:39 UTC

Update Date

2022-03-07 02:53:08 UTC

HMDB ID

HMDB0031816

Secondary Accession Numbers

HMDB31816

Metabolite Identification

Common Name

3-Hydroxyflavone

Description

3-Hydroxyflavone, also known as flavon-3-ol, belongs to the class of organic compounds known as flavonols. Flavonols are compounds that contain a flavone (2-phenyl-1-benzopyran-4-one) backbone carrying a hydroxyl group at the 3-position. 3-Hydroxyflavone is found, on average, in the highest concentration within papayas (Carica papaya). 3-Hydroxyflavone has also been detected, but not quantified in, several different foods, such as red raspberries (Rubus idaeus), teas (Camellia sinensis), black tea, pomegranates (Punica granatum), and brassicas. This could make 3-hydroxyflavone a potential biomarker for the consumption of these foods. 3-Hydroxyflavone 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 3-Hydroxyflavone.

Structure

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

HMDB0031816
     RDKit          3D
3-Hydroxyflavone
 28 30  0  0  0  0  0  0  0  0999 V2000
   -2.4671   -0.1767   -2.4903 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7670   -0.1202   -1.4456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3681   -0.2211   -1.4980 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1958   -0.3841   -2.7440 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3815   -0.1597   -0.3702 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8350   -0.2534   -0.3140 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4300   -0.1673    0.9563 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7695   -0.2402    1.1432 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5875   -0.4070    0.0329 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0108   -0.4919   -1.2118 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6290   -0.4165   -1.4027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2810   -0.0015    0.7603 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5762    0.0981    0.8714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1859    0.2640    2.1150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5421    0.3704    2.2522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3426    0.3114    1.1135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7722    0.1501   -0.1111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4028    0.0440   -0.2367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3542   -0.4296   -3.5765 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8209   -0.0352    1.8620 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1975   -0.1716    2.1225 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6482   -0.4608    0.2205 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6857   -0.6228   -2.0605 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2533   -0.4901   -2.3975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5674    0.3088    2.9872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0306    0.4983    3.1993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4072    0.3962    1.2342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3802    0.1018   -1.0116 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
  3  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
  5 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18  2  1  0
 11  6  1  0
 18 13  1  0
  4 19  1  0
  7 20  1  0
  8 21  1  0
  9 22  1  0
 10 23  1  0
 11 24  1  0
 14 25  1  0
 15 26  1  0
 16 27  1  0
 17 28  1  0
M  END


  Mrv0541 05061306082D          

 18 20  0  0  0  0            999 V2000
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -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   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    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
  5  4  2  0  0  0  0
  6  2  1  0  0  0  0
  7  3  2  0  0  0  0
  8  4  1  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  8  2  0  0  0  0
 12  9  2  0  0  0  0
 12 11  1  0  0  0  0
 13 11  1  0  0  0  0
 14 13  1  0  0  0  0
 15 10  1  0  0  0  0
 15 14  2  0  0  0  0
 16 13  2  0  0  0  0
 17 14  1  0  0  0  0
 18 12  1  0  0  0  0
 18 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0031816

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=C(OC2=CC=CC=C2C1=O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H10O3/c16-13-11-8-4-5-9-12(11)18-15(14(13)17)10-6-2-1-3-7-10/h1-9,17H

> <INCHI_KEY>
HVQAJTFOCKOKIN-UHFFFAOYSA-N

> <FORMULA>
C15H10O3

> <MOLECULAR_WEIGHT>
238.2381

> <EXACT_MASS>
238.062994186

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
24.613674260388922

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-hydroxy-2-phenyl-4H-chromen-4-one

> <ALOGPS_LOGP>
2.55

> <JCHEM_LOGP>
2.7205607506666665

> <ALOGPS_LOGS>
-3.23

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.292000412173541

> <JCHEM_PKA_STRONGEST_BASIC>
-3.663939019728976

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
68.93860000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.39e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
flavonol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0031816
     RDKit          3D
3-Hydroxyflavone
 28 30  0  0  0  0  0  0  0  0999 V2000
   -2.4671   -0.1767   -2.4903 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7670   -0.1202   -1.4456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3681   -0.2211   -1.4980 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1958   -0.3841   -2.7440 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3815   -0.1597   -0.3702 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8350   -0.2534   -0.3140 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4300   -0.1673    0.9563 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7695   -0.2402    1.1432 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5875   -0.4070    0.0329 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0108   -0.4919   -1.2118 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6290   -0.4165   -1.4027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2810   -0.0015    0.7603 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5762    0.0981    0.8714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1859    0.2640    2.1150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5421    0.3704    2.2522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3426    0.3114    1.1135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7722    0.1501   -0.1111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4028    0.0440   -0.2367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3542   -0.4296   -3.5765 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8209   -0.0352    1.8620 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1975   -0.1716    2.1225 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6482   -0.4608    0.2205 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6857   -0.6228   -2.0605 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2533   -0.4901   -2.3975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5674    0.3088    2.9872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0306    0.4983    3.1993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4072    0.3962    1.2342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3802    0.1018   -1.0116 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
  3  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
  5 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18  2  1  0
 11  6  1  0
 18 13  1  0
  4 19  1  0
  7 20  1  0
  8 21  1  0
  9 22  1  0
 10 23  1  0
 11 24  1  0
 14 25  1  0
 15 26  1  0
 16 27  1  0
 17 28  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       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    6                                                       
CONECT    3    1    7                                                       
CONECT    4    5    8                                                       
CONECT    5    4    9                                                       
CONECT    6    2   10                                                       
CONECT    7    3   10                                                       
CONECT    8    4   11                                                       
CONECT    9    5   12                                                       
CONECT   10    6    7   15                                                  
CONECT   11    8   12   13                                                  
CONECT   12    9   11   18                                                  
CONECT   13   11   14   16                                                  
CONECT   14   13   15   17                                                  
CONECT   15   10   14   18                                                  
CONECT   16   13                                                            
CONECT   17   14                                                            
CONECT   18   12   15                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   40    0
END

COMPND    HMDB0031816
HETATM    1  O1  UNL     1      -2.467  -0.177  -2.490  1.00  0.00           O  
HETATM    2  C1  UNL     1      -1.767  -0.120  -1.446  1.00  0.00           C  
HETATM    3  C2  UNL     1      -0.368  -0.221  -1.498  1.00  0.00           C  
HETATM    4  O2  UNL     1       0.196  -0.384  -2.744  1.00  0.00           O  
HETATM    5  C3  UNL     1       0.382  -0.160  -0.370  1.00  0.00           C  
HETATM    6  C4  UNL     1       1.835  -0.253  -0.314  1.00  0.00           C  
HETATM    7  C5  UNL     1       2.430  -0.167   0.956  1.00  0.00           C  
HETATM    8  C6  UNL     1       3.769  -0.240   1.143  1.00  0.00           C  
HETATM    9  C7  UNL     1       4.587  -0.407   0.033  1.00  0.00           C  
HETATM   10  C8  UNL     1       4.011  -0.492  -1.212  1.00  0.00           C  
HETATM   11  C9  UNL     1       2.629  -0.416  -1.403  1.00  0.00           C  
HETATM   12  O3  UNL     1      -0.281  -0.002   0.760  1.00  0.00           O  
HETATM   13  C10 UNL     1      -1.576   0.098   0.871  1.00  0.00           C  
HETATM   14  C11 UNL     1      -2.186   0.264   2.115  1.00  0.00           C  
HETATM   15  C12 UNL     1      -3.542   0.370   2.252  1.00  0.00           C  
HETATM   16  C13 UNL     1      -4.343   0.311   1.113  1.00  0.00           C  
HETATM   17  C14 UNL     1      -3.772   0.150  -0.111  1.00  0.00           C  
HETATM   18  C15 UNL     1      -2.403   0.044  -0.237  1.00  0.00           C  
HETATM   19  H1  UNL     1      -0.354  -0.430  -3.576  1.00  0.00           H  
HETATM   20  H2  UNL     1       1.821  -0.035   1.862  1.00  0.00           H  
HETATM   21  H3  UNL     1       4.197  -0.172   2.123  1.00  0.00           H  
HETATM   22  H4  UNL     1       5.648  -0.461   0.220  1.00  0.00           H  
HETATM   23  H5  UNL     1       4.686  -0.623  -2.060  1.00  0.00           H  
HETATM   24  H6  UNL     1       2.253  -0.490  -2.398  1.00  0.00           H  
HETATM   25  H7  UNL     1      -1.567   0.309   2.987  1.00  0.00           H  
HETATM   26  H8  UNL     1      -4.031   0.498   3.199  1.00  0.00           H  
HETATM   27  H9  UNL     1      -5.407   0.396   1.234  1.00  0.00           H  
HETATM   28  H10 UNL     1      -4.380   0.102  -1.012  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   18
CONECT    3    4    5    5
CONECT    4   19
CONECT    5    6   12
CONECT    6    7    7   11
CONECT    7    8   20
CONECT    8    9    9   21
CONECT    9   10   22
CONECT   10   11   11   23
CONECT   11   24
CONECT   12   13
CONECT   13   14   14   18
CONECT   14   15   25
CONECT   15   16   16   26
CONECT   16   17   27
CONECT   17   18   18   28
END

HMDB0031816
     RDKit          3D
3-Hydroxyflavone
 28 30  0  0  0  0  0  0  0  0999 V2000
   -2.4671   -0.1767   -2.4903 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7670   -0.1202   -1.4456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3681   -0.2211   -1.4980 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1958   -0.3841   -2.7440 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3815   -0.1597   -0.3702 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8350   -0.2534   -0.3140 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4300   -0.1673    0.9563 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7695   -0.2402    1.1432 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5875   -0.4070    0.0329 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0108   -0.4919   -1.2118 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6290   -0.4165   -1.4027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2810   -0.0015    0.7603 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5762    0.0981    0.8714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1859    0.2640    2.1150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5421    0.3704    2.2522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3426    0.3114    1.1135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7722    0.1501   -0.1111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4028    0.0440   -0.2367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3542   -0.4296   -3.5765 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8209   -0.0352    1.8620 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1975   -0.1716    2.1225 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6482   -0.4608    0.2205 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6857   -0.6228   -2.0605 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2533   -0.4901   -2.3975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5674    0.3088    2.9872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0306    0.4983    3.1993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4072    0.3962    1.2342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3802    0.1018   -1.0116 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
  3  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
  5 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18  2  1  0
 11  6  1  0
 18 13  1  0
  4 19  1  0
  7 20  1  0
  8 21  1  0
  9 22  1  0
 10 23  1  0
 11 24  1  0
 14 25  1  0
 15 26  1  0
 16 27  1  0
 17 28  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-Hydroxy-2-phenyl-4H-1-benzopyran-4-one	ChEBI
3-Hydroxy-2-phenylchromone	ChEBI
Flavon-3-ol	ChEBI
Flavonol	MeSH
3-Hydroxyflavone	ChEBI
3,4-Flavandione	HMDB
3-Hydroxy-2-phenyl-4H-1-benzopyran-4-one, 9ci	HMDB
Flavonols	HMDB

Chemical Formula

C₁₅H₁₀O₃

Average Molecular Weight

238.2381

Monoisotopic Molecular Weight

238.062994186

IUPAC Name

3-hydroxy-2-phenyl-4H-chromen-4-one

Traditional Name

flavonol

CAS Registry Number

577-85-5

SMILES

OC1=C(OC2=CC=CC=C2C1=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C15H10O3/c16-13-11-8-4-5-9-12(11)18-15(14(13)17)10-6-2-1-3-7-10/h1-9,17H

InChI Key

HVQAJTFOCKOKIN-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonols. Flavonols are compounds that contain a flavone (2-phenyl-1-benzopyran-4-one) backbone carrying a hydroxyl group at the 3-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavones

Direct Parent

Flavonols

Alternative Parents

Substituents

3-hydroxyflavone
3-hydroxyflavonoid
Hydroxyflavonoid
Chromone
Benzopyran
1-benzopyran
Pyranone
Monocyclic benzene moiety
Pyran
Benzenoid
Heteroaromatic compound
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

flavonols (CHEBI:5078 )
monohydroxyflavone (CHEBI:5078 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0031816)
Cell membrane (HMDB: HMDB0031816)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0031816)

Source

Endogenous

Endogenous (HMDB: HMDB0031816)

Plant

Plant (HMDB: HMDB0031816)

Exogenous

Food

Food (HMDB: HMDB0031816)

Fruit

Tropical fruit

Papaya (FooDB: FOOD00041)
Pomegranate (FooDB: FOOD00151)

Berry

Red raspberry (FooDB: FOOD00162)

Tea

Herb and spice

Herb

Fenugreek (FooDB: FOOD00186)

Vegetable

Brassica

Brassicas (FooDB: FOOD00857)

Exogenous (HMDB: HMDB0031816)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	170 °C	Not Available
Boiling Point	393.72 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	158.1 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	3.477 (est)	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	146.287	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001460

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.14 g/L	ALOGPS
logP	2.55	ALOGPS
logP	2.72	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	9.29	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	68.94 m³·mol⁻¹	ChemAxon
Polarizability	24.61 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]+	153.323	31661259
DarkChem	[M-H]-	153.68	31661259
DeepCCS	[M+H]+	153.325	30932474
DeepCCS	[M-H]-	150.93	30932474
DeepCCS	[M-2H]-	183.976	30932474
DeepCCS	[M+Na]+	159.274	30932474
AllCCS	[M+H]+	153.1	32859911
AllCCS	[M+H-H2O]+	148.8	32859911
AllCCS	[M+NH4]+	157.0	32859911
AllCCS	[M+Na]+	158.2	32859911
AllCCS	[M-H]-	154.1	32859911
AllCCS	[M+Na-2H]-	153.3	32859911
AllCCS	[M+HCOO]-	152.5	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. Predicted by Afia on May 17, 2022.	7.79 minutes	32390414
Predicted by Siyang on May 30, 2022	15.8798 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.21 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2818.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	533.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	226.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	322.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	464.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	615.0 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	745.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	152.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1481.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	589.1 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	1462.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	447.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	497.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	458.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	332.6 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	50.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Hydroxyflavone	OC1=C(OC2=CC=CC=C2C1=O)C1=CC=CC=C1	3115.2	Standard polar	33892256
3-Hydroxyflavone	OC1=C(OC2=CC=CC=C2C1=O)C1=CC=CC=C1	2109.9	Standard non polar	33892256
3-Hydroxyflavone	OC1=C(OC2=CC=CC=C2C1=O)C1=CC=CC=C1	2210.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Hydroxyflavone,1TMS,isomer #1	C[Si](C)(C)OC1=C(C2=CC=CC=C2)OC2=CC=CC=C2C1=O	2458.7	Semi standard non polar	33892256
3-Hydroxyflavone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=C(C2=CC=CC=C2)OC2=CC=CC=C2C1=O	2702.4	Semi standard non polar	33892256

Spectra

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

3-hydroxyflavone

METLIN ID

Not Available

PubChem Compound

11349

PDB ID

Not Available

ChEBI ID

5078

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1190681

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

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

Showing metabocard for 3-Hydroxyflavone (HMDB0031816)

MOL for HMDB0031816 (3-Hydroxyflavone)

3D MOL for HMDB0031816 (3-Hydroxyflavone)

3D SDF for HMDB0031816 (3-Hydroxyflavone)

3D-SDF for HMDB0031816 (3-Hydroxyflavone)

PDB for HMDB0031816 (3-Hydroxyflavone)

3D PDB for HMDB0031816 (3-Hydroxyflavone)

SMILES for HMDB0031816 (3-Hydroxyflavone)

INCHI for HMDB0031816 (3-Hydroxyflavone)

Structure for HMDB0031816 (3-Hydroxyflavone)

3D Structure for HMDB0031816 (3-Hydroxyflavone)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

Enzymes

Reactions