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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:46:54 UTC

Update Date

2022-03-07 02:53:11 UTC

HMDB ID

HMDB0031969

Secondary Accession Numbers

HMDB31969

Metabolite Identification

Common Name

3-Hydroxy-2-(4-methylbenzoyl)-4H-1-benzopyran-4-one

Description

3-Hydroxy-2-(4-methylbenzoyl)-4H-1-benzopyran-4-one, also known as 3-hydroxy-2-(4-methylbenzoyl)chromone, belongs to the class of organic compounds known as aryl-phenylketones. These are aromatic compounds containing a ketone substituted by one aryl group, and a phenyl group. Based on a literature review a significant number of articles have been published on 3-Hydroxy-2-(4-methylbenzoyl)-4H-1-benzopyran-4-one.

Structure

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

HMDB0031969
     RDKit          3D
3-Hydroxy-2-(4-methylbenzoyl)-4H-1-benzopyran-4-one
 33 35  0  0  0  0  0  0  0  0999 V2000
    5.2518    1.6674    0.8532 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0770    0.8076    0.5146 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1065   -0.5558    0.6309 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0018   -1.3095    0.3085 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8070   -0.7472   -0.1474 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6933   -1.6157   -0.4664 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9640   -2.8078   -0.8049 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7053   -1.2096   -0.4229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0710   -0.0072   -0.0794 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3197    0.4080   -0.0242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6211    1.6995    0.3499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9093    2.1883    0.4250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9248    1.3171    0.1037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6583    0.0115   -0.2767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3511   -0.4456   -0.3411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0200   -1.7251   -0.7100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9571   -2.5156   -1.0024 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7102   -2.1006   -0.7496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3308   -3.3777   -1.1151 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7974    0.6262   -0.2576 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9122    1.3943    0.0672 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9519    2.2938    1.7242 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4405    2.2991   -0.0265 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1046    1.0397    1.1189 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0170   -1.0190    0.9809 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0260   -2.3966    0.4015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8113    2.3490    0.5928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1136    3.2193    0.7257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9509    1.6460    0.1451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4401   -0.6704   -0.5272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0454   -4.0488   -1.3584 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8885    1.1102   -0.6112 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9004    2.4753   -0.0209 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
  5 20  1  0
 20 21  2  0
 21  2  1  0
 18  8  2  0
 15 10  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  4 26  1  0
 11 27  1  0
 12 28  1  0
 13 29  1  0
 14 30  1  0
 19 31  1  0
 20 32  1  0
 21 33  1  0
M  END


  Mrv0541 05061306162D          

 21 23  0  0  0  0            999 V2000
    2.8579   -4.9500    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
    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
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    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
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    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
    0.7145   -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
    2.8579   -1.6500    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
    3.5724   -1.2375    0.0000 O   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
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  8  6  1  0  0  0  0
  9  7  2  0  0  0  0
 10  1  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
 11  9  1  0  0  0  0
 12  4  2  0  0  0  0
 13  5  2  0  0  0  0
 13 12  1  0  0  0  0
 14 11  1  0  0  0  0
 15 12  1  0  0  0  0
 16 15  1  0  0  0  0
 17 14  1  0  0  0  0
 17 16  2  0  0  0  0
 18 14  2  0  0  0  0
 19 15  2  0  0  0  0
 20 16  1  0  0  0  0
 21 13  1  0  0  0  0
 21 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0031969

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=CC=C(C=C1)C(=O)C1=C(O)C(=O)C2=CC=CC=C2O1

> <INCHI_IDENTIFIER>
InChI=1S/C17H12O4/c1-10-6-8-11(9-7-10)14(18)17-16(20)15(19)12-4-2-3-5-13(12)21-17/h2-9,20H,1H3

> <INCHI_KEY>
IZGJHVUQSWAPEG-UHFFFAOYSA-N

> <FORMULA>
C17H12O4

> <MOLECULAR_WEIGHT>
280.2748

> <EXACT_MASS>
280.073558872

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
28.97487839861126

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-hydroxy-2-(4-methylbenzoyl)-4H-chromen-4-one

> <ALOGPS_LOGP>
2.60

> <JCHEM_LOGP>
3.317943148666666

> <ALOGPS_LOGS>
-3.97

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.776052512341606

> <JCHEM_PKA_STRONGEST_BASIC>
-4.327014631387436

> <JCHEM_POLAR_SURFACE_AREA>
63.60000000000001

> <JCHEM_REFRACTIVITY>
79.41909999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.02e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-hydroxy-2-(4-methylbenzoyl)chromen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0031969
     RDKit          3D
3-Hydroxy-2-(4-methylbenzoyl)-4H-1-benzopyran-4-one
 33 35  0  0  0  0  0  0  0  0999 V2000
    5.2518    1.6674    0.8532 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0770    0.8076    0.5146 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1065   -0.5558    0.6309 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0018   -1.3095    0.3085 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8070   -0.7472   -0.1474 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6933   -1.6157   -0.4664 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9640   -2.8078   -0.8049 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7053   -1.2096   -0.4229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0710   -0.0072   -0.0794 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3197    0.4080   -0.0242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6211    1.6995    0.3499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9093    2.1883    0.4250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9248    1.3171    0.1037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6583    0.0115   -0.2767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3511   -0.4456   -0.3411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0200   -1.7251   -0.7100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9571   -2.5156   -1.0024 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7102   -2.1006   -0.7496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3308   -3.3777   -1.1151 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7974    0.6262   -0.2576 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9122    1.3943    0.0672 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9519    2.2938    1.7242 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4405    2.2991   -0.0265 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1046    1.0397    1.1189 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0170   -1.0190    0.9809 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0260   -2.3966    0.4015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8113    2.3490    0.5928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1136    3.2193    0.7257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9509    1.6460    0.1451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4401   -0.6704   -0.5272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0454   -4.0488   -1.3584 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8885    1.1102   -0.6112 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9004    2.4753   -0.0209 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
  5 20  1  0
 20 21  2  0
 21  2  1  0
 18  8  2  0
 15 10  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  4 26  1  0
 11 27  1  0
 12 28  1  0
 13 29  1  0
 14 30  1  0
 19 31  1  0
 20 32  1  0
 21 33  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
CONECT    1   10                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2   12                                                       
CONECT    5    3   13                                                       
CONECT    6    8   10                                                       
CONECT    7    9   10                                                       
CONECT    8    6   11                                                       
CONECT    9    7   11                                                       
CONECT   10    1    6    7                                                  
CONECT   11    8    9   14                                                  
CONECT   12    4   13   15                                                  
CONECT   13    5   12   21                                                  
CONECT   14   11   17   18                                                  
CONECT   15   12   16   19                                                  
CONECT   16   15   17   20                                                  
CONECT   17   14   16   21                                                  
CONECT   18   14                                                            
CONECT   19   15                                                            
CONECT   20   16                                                            
CONECT   21   13   17                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    HMDB0031969
HETATM    1  C1  UNL     1       5.252   1.667   0.853  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.077   0.808   0.515  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.106  -0.556   0.631  1.00  0.00           C  
HETATM    4  C4  UNL     1       3.002  -1.310   0.309  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.807  -0.747  -0.147  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.693  -1.616  -0.466  1.00  0.00           C  
HETATM    7  O1  UNL     1       0.964  -2.808  -0.805  1.00  0.00           O  
HETATM    8  C7  UNL     1      -0.705  -1.210  -0.423  1.00  0.00           C  
HETATM    9  O2  UNL     1      -1.071  -0.007  -0.079  1.00  0.00           O  
HETATM   10  C8  UNL     1      -2.320   0.408  -0.024  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.621   1.700   0.350  1.00  0.00           C  
HETATM   12  C10 UNL     1      -3.909   2.188   0.425  1.00  0.00           C  
HETATM   13  C11 UNL     1      -4.925   1.317   0.104  1.00  0.00           C  
HETATM   14  C12 UNL     1      -4.658   0.011  -0.277  1.00  0.00           C  
HETATM   15  C13 UNL     1      -3.351  -0.446  -0.341  1.00  0.00           C  
HETATM   16  C14 UNL     1      -3.020  -1.725  -0.710  1.00  0.00           C  
HETATM   17  O3  UNL     1      -3.957  -2.516  -1.002  1.00  0.00           O  
HETATM   18  C15 UNL     1      -1.710  -2.101  -0.750  1.00  0.00           C  
HETATM   19  O4  UNL     1      -1.331  -3.378  -1.115  1.00  0.00           O  
HETATM   20  C16 UNL     1       1.797   0.626  -0.258  1.00  0.00           C  
HETATM   21  C17 UNL     1       2.912   1.394   0.067  1.00  0.00           C  
HETATM   22  H1  UNL     1       4.952   2.294   1.724  1.00  0.00           H  
HETATM   23  H2  UNL     1       5.440   2.299  -0.026  1.00  0.00           H  
HETATM   24  H3  UNL     1       6.105   1.040   1.119  1.00  0.00           H  
HETATM   25  H4  UNL     1       5.017  -1.019   0.981  1.00  0.00           H  
HETATM   26  H5  UNL     1       3.026  -2.397   0.402  1.00  0.00           H  
HETATM   27  H6  UNL     1      -1.811   2.349   0.593  1.00  0.00           H  
HETATM   28  H7  UNL     1      -4.114   3.219   0.726  1.00  0.00           H  
HETATM   29  H8  UNL     1      -5.951   1.646   0.145  1.00  0.00           H  
HETATM   30  H9  UNL     1      -5.440  -0.670  -0.527  1.00  0.00           H  
HETATM   31  H10 UNL     1      -2.045  -4.049  -1.358  1.00  0.00           H  
HETATM   32  H11 UNL     1       0.888   1.110  -0.611  1.00  0.00           H  
HETATM   33  H12 UNL     1       2.900   2.475  -0.021  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3    3   21
CONECT    3    4   25
CONECT    4    5    5   26
CONECT    5    6   20
CONECT    6    7    7    8
CONECT    8    9   18   18
CONECT    9   10
CONECT   10   11   11   15
CONECT   11   12   27
CONECT   12   13   13   28
CONECT   13   14   29
CONECT   14   15   15   30
CONECT   15   16
CONECT   16   17   17   18
CONECT   18   19
CONECT   19   31
CONECT   20   21   21   32
CONECT   21   33
END

HMDB0031969
     RDKit          3D
3-Hydroxy-2-(4-methylbenzoyl)-4H-1-benzopyran-4-one
 33 35  0  0  0  0  0  0  0  0999 V2000
    5.2518    1.6674    0.8532 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0770    0.8076    0.5146 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1065   -0.5558    0.6309 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0018   -1.3095    0.3085 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8070   -0.7472   -0.1474 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6933   -1.6157   -0.4664 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9640   -2.8078   -0.8049 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7053   -1.2096   -0.4229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0710   -0.0072   -0.0794 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3197    0.4080   -0.0242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6211    1.6995    0.3499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9093    2.1883    0.4250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9248    1.3171    0.1037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6583    0.0115   -0.2767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3511   -0.4456   -0.3411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0200   -1.7251   -0.7100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9571   -2.5156   -1.0024 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7102   -2.1006   -0.7496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3308   -3.3777   -1.1151 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7974    0.6262   -0.2576 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9122    1.3943    0.0672 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9519    2.2938    1.7242 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4405    2.2991   -0.0265 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1046    1.0397    1.1189 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0170   -1.0190    0.9809 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0260   -2.3966    0.4015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8113    2.3490    0.5928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1136    3.2193    0.7257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9509    1.6460    0.1451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4401   -0.6704   -0.5272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0454   -4.0488   -1.3584 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8885    1.1102   -0.6112 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9004    2.4753   -0.0209 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
  5 20  1  0
 20 21  2  0
 21  2  1  0
 18  8  2  0
 15 10  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  4 26  1  0
 11 27  1  0
 12 28  1  0
 13 29  1  0
 14 30  1  0
 19 31  1  0
 20 32  1  0
 21 33  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-Hydroxy-2-(4-methylbenzoyl)chromone	HMDB

Chemical Formula

C₁₇H₁₂O₄

Average Molecular Weight

280.2748

Monoisotopic Molecular Weight

280.073558872

IUPAC Name

3-hydroxy-2-(4-methylbenzoyl)-4H-chromen-4-one

Traditional Name

3-hydroxy-2-(4-methylbenzoyl)chromen-4-one

CAS Registry Number

173866-78-9

SMILES

CC1=CC=C(C=C1)C(=O)C1=C(O)C(=O)C2=CC=CC=C2O1

InChI Identifier

InChI=1S/C17H12O4/c1-10-6-8-11(9-7-10)14(18)17-16(20)15(19)12-4-2-3-5-13(12)21-17/h2-9,20H,1H3

InChI Key

IZGJHVUQSWAPEG-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aryl-phenylketones. These are aromatic compounds containing a ketone substituted by one aryl group, and a phenyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Aryl-phenylketones

Alternative Parents

Substituents

Aryl-phenylketone
Chromone
Benzopyran
1-benzopyran
Benzoyl
Toluene
Pyranone
Benzenoid
Monocyclic benzene moiety
Pyran
Vinylogous acid
Heteroaromatic compound
Oxacycle
Organoheterocyclic compound
Organic oxide
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0031969)
Cell membrane (HMDB: HMDB0031969)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0031969)

Source

Endogenous

Endogenous (HMDB: HMDB0031969)

Plant

Plant (HMDB: HMDB0031969)

Exogenous

Food

Food (HMDB: HMDB0031969)

Fruit

Fruits (FooDB: FOOD00871)

Exogenous (HMDB: HMDB0031969)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.03 g/L	ALOGPS
logP	2.6	ALOGPS
logP	3.32	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	7.78	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	79.42 m³·mol⁻¹	ChemAxon
Polarizability	28.97 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]+	166.077	31661259
DarkChem	[M-H]-	168.324	31661259
DeepCCS	[M+H]+	164.078	30932474
DeepCCS	[M-H]-	161.72	30932474
DeepCCS	[M-2H]-	194.895	30932474
DeepCCS	[M+Na]+	170.171	30932474
AllCCS	[M+H]+	164.9	32859911
AllCCS	[M+H-H2O]+	160.9	32859911
AllCCS	[M+NH4]+	168.6	32859911
AllCCS	[M+Na]+	169.6	32859911
AllCCS	[M-H]-	164.8	32859911
AllCCS	[M+Na-2H]-	164.0	32859911
AllCCS	[M+HCOO]-	163.3	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.	8.33 minutes	32390414
Predicted by Siyang on May 30, 2022	16.3153 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.02 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2776.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	504.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	211.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	286.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	434.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	717.6 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	898.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	92.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1473.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	627.0 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	1676.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	481.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	470.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	408.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	287.0 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	44.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Hydroxy-2-(4-methylbenzoyl)-4H-1-benzopyran-4-one	CC1=CC=C(C=C1)C(=O)C1=C(O)C(=O)C2=CC=CC=C2O1	3105.1	Standard polar	33892256
3-Hydroxy-2-(4-methylbenzoyl)-4H-1-benzopyran-4-one	CC1=CC=C(C=C1)C(=O)C1=C(O)C(=O)C2=CC=CC=C2O1	2433.8	Standard non polar	33892256
3-Hydroxy-2-(4-methylbenzoyl)-4H-1-benzopyran-4-one	CC1=CC=C(C=C1)C(=O)C1=C(O)C(=O)C2=CC=CC=C2O1	2614.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Hydroxy-2-(4-methylbenzoyl)-4H-1-benzopyran-4-one,1TMS,isomer #1	CC1=CC=C(C(=O)C2=C(O[Si](C)(C)C)C(=O)C3=CC=CC=C3O2)C=C1	2696.2	Semi standard non polar	33892256
3-Hydroxy-2-(4-methylbenzoyl)-4H-1-benzopyran-4-one,1TBDMS,isomer #1	CC1=CC=C(C(=O)C2=C(O[Si](C)(C)C(C)(C)C)C(=O)C3=CC=CC=C3O2)C=C1	2958.2	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 - 3-Hydroxy-2-(4-methylbenzoyl)-4H-1-benzopyran-4-one GC-MS (Non-derivatized) - 70eV, Positive	splash10-0gb9-3930000000-01ceadd069fcffd7f633	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxy-2-(4-methylbenzoyl)-4H-1-benzopyran-4-one GC-MS (1 TMS) - 70eV, Positive	splash10-0600-4924000000-c1ff2c6a5612c8c76644	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxy-2-(4-methylbenzoyl)-4H-1-benzopyran-4-one GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxy-2-(4-methylbenzoyl)-4H-1-benzopyran-4-one 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 - 3-Hydroxy-2-(4-methylbenzoyl)-4H-1-benzopyran-4-one 10V, Positive-QTOF	splash10-001i-0290000000-f0d78ac95772e595c335	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-2-(4-methylbenzoyl)-4H-1-benzopyran-4-one 20V, Positive-QTOF	splash10-0159-1970000000-0e26dc2d5f9303619b93	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-2-(4-methylbenzoyl)-4H-1-benzopyran-4-one 40V, Positive-QTOF	splash10-01bc-9800000000-5d0457d5011e794d9c1c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-2-(4-methylbenzoyl)-4H-1-benzopyran-4-one 10V, Negative-QTOF	splash10-004i-0190000000-c19c2501e3b81841cb0f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-2-(4-methylbenzoyl)-4H-1-benzopyran-4-one 20V, Negative-QTOF	splash10-01tc-4890000000-6fec9750a7b46978a161	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-2-(4-methylbenzoyl)-4H-1-benzopyran-4-one 40V, Negative-QTOF	splash10-014l-4900000000-ef6bf7b23ce6b605cec5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-2-(4-methylbenzoyl)-4H-1-benzopyran-4-one 10V, Negative-QTOF	splash10-004i-0090000000-e7bff69121635cb2fca7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-2-(4-methylbenzoyl)-4H-1-benzopyran-4-one 20V, Negative-QTOF	splash10-004i-0190000000-29d60189cf78cb4411b4	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-2-(4-methylbenzoyl)-4H-1-benzopyran-4-one 40V, Negative-QTOF	splash10-0006-8900000000-1d8f0919df37ed0cba29	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-2-(4-methylbenzoyl)-4H-1-benzopyran-4-one 10V, Positive-QTOF	splash10-001i-0390000000-31a8bf0648700de84613	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-2-(4-methylbenzoyl)-4H-1-benzopyran-4-one 20V, Positive-QTOF	splash10-001i-0390000000-ff119f019d680f9a7445	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-2-(4-methylbenzoyl)-4H-1-benzopyran-4-one 40V, Positive-QTOF	splash10-016u-9510000000-d33109ef14ae06212776	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB008661

KNApSAcK ID

Not Available

Chemspider ID

30776927

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

137185905

PDB ID

Not Available

ChEBI ID

174665

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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

Showing metabocard for 3-Hydroxy-2-(4-methylbenzoyl)-4H-1-benzopyran-4-one (HMDB0031969)

MOL for HMDB0031969 (3-Hydroxy-2-(4-methylbenzoyl)-4H-1-benzopyran-4-one)

3D MOL for HMDB0031969 (3-Hydroxy-2-(4-methylbenzoyl)-4H-1-benzopyran-4-one)

3D SDF for HMDB0031969 (3-Hydroxy-2-(4-methylbenzoyl)-4H-1-benzopyran-4-one)

3D-SDF for HMDB0031969 (3-Hydroxy-2-(4-methylbenzoyl)-4H-1-benzopyran-4-one)

PDB for HMDB0031969 (3-Hydroxy-2-(4-methylbenzoyl)-4H-1-benzopyran-4-one)

3D PDB for HMDB0031969 (3-Hydroxy-2-(4-methylbenzoyl)-4H-1-benzopyran-4-one)

SMILES for HMDB0031969 (3-Hydroxy-2-(4-methylbenzoyl)-4H-1-benzopyran-4-one)

INCHI for HMDB0031969 (3-Hydroxy-2-(4-methylbenzoyl)-4H-1-benzopyran-4-one)

Structure for HMDB0031969 (3-Hydroxy-2-(4-methylbenzoyl)-4H-1-benzopyran-4-one)

3D Structure for HMDB0031969 (3-Hydroxy-2-(4-methylbenzoyl)-4H-1-benzopyran-4-one)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra