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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 02:07:22 UTC

Update Date

2022-03-07 02:56:38 UTC

HMDB ID

HMDB0040560

Secondary Accession Numbers

HMDB40560

Metabolite Identification

Common Name

4',5,7-Trihydroxy-3-methoxyflavanone

Description

4',5,7-Trihydroxy-3-methoxyflavanone belongs to the class of organic compounds known as 3-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C3 atom of the flavonoid backbone. 4',5,7-Trihydroxy-3-methoxyflavanone has been detected, but not quantified in, european plums (Prunus domestica) and fruits. This could make 4',5,7-trihydroxy-3-methoxyflavanone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 4',5,7-Trihydroxy-3-methoxyflavanone.

Structure

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

HMDB0040560
     RDKit          3D
4',5,7-Trihydroxy-3-methoxyflavanone
 36 38  0  0  0  0  0  0  0  0999 V2000
    0.3521   -3.4642   -0.3626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4553   -2.3704   -0.6623 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0782   -1.2412    0.0802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2149   -0.8808    0.9281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3280   -1.3873    2.0597 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2055    0.0607    0.4580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5129   -0.0149    0.8046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9803   -1.0006    1.6248 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3822    0.9645    0.2843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9511    1.9683   -0.5445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8311    2.9375   -1.0552 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6140    2.0121   -0.8754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7325    1.0714   -0.3854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3825    1.0503   -0.6696 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3803   -0.1226   -0.8142 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7948    0.2285   -0.5603 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0835    1.0238    0.5215 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4108    1.3690    0.7823 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4391    0.9376   -0.0104 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7455    1.3158    0.3011 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1519    0.1410   -1.0942 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8302   -0.2014   -1.3520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0089   -4.3078   -0.9863 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2792   -3.7606    0.6902 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3833   -3.2482   -0.7049 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7811   -1.5419    0.7166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4402   -1.7210    2.0030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4260    0.8995    0.5653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9972    3.8109   -0.5358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2292    2.7928   -1.5315 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2758   -0.4610   -1.8658 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3121    1.4002    1.1911 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5979    1.9951    1.6408 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3422    0.7736    0.9085 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9673   -0.1975   -1.7176 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6430   -0.8313   -2.2159 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 15  3  1  0
 22 16  1  0
 13  6  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  8 27  1  0
  9 28  1  0
 11 29  1  0
 12 30  1  0
 15 31  1  0
 17 32  1  0
 18 33  1  0
 20 34  1  0
 21 35  1  0
 22 36  1  0
M  END


  Mrv0541 05061311562D          

 22 24  0  0  0  0            999 V2000
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    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
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    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
    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   -1.6500    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
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  2  1  0  0  0  0
  5  3  2  0  0  0  0
  8  2  2  0  0  0  0
  8  3  1  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  7  2  0  0  0  0
 13 11  2  0  0  0  0
 13 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15  8  1  0  0  0  0
 16 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17  9  1  0  0  0  0
 18 10  1  0  0  0  0
 19 11  1  0  0  0  0
 20 14  2  0  0  0  0
 21  1  1  0  0  0  0
 21 16  1  0  0  0  0
 22 12  1  0  0  0  0
 22 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0040560

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1C(OC2=CC(O)=CC(O)=C2C1=O)C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H14O6/c1-21-16-14(20)13-11(19)6-10(18)7-12(13)22-15(16)8-2-4-9(17)5-3-8/h2-7,15-19H,1H3

> <INCHI_KEY>
JRLDUAGSJUMVDP-UHFFFAOYSA-N

> <FORMULA>
C16H14O6

> <MOLECULAR_WEIGHT>
302.2788

> <EXACT_MASS>
302.07903818

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
30.13156705365974

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.51

> <JCHEM_LOGP>
2.763076093333333

> <ALOGPS_LOGS>
-3.11

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.442633274383763

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.804778281598569

> <JCHEM_PKA_STRONGEST_BASIC>
-3.878219730089982

> <JCHEM_POLAR_SURFACE_AREA>
96.22

> <JCHEM_REFRACTIVITY>
77.37920000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.36e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,7-dihydroxy-2-(4-hydroxyphenyl)-3-methoxy-2,3-dihydro-1-benzopyran-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0040560
     RDKit          3D
4',5,7-Trihydroxy-3-methoxyflavanone
 36 38  0  0  0  0  0  0  0  0999 V2000
    0.3521   -3.4642   -0.3626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4553   -2.3704   -0.6623 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0782   -1.2412    0.0802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2149   -0.8808    0.9281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3280   -1.3873    2.0597 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2055    0.0607    0.4580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5129   -0.0149    0.8046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9803   -1.0006    1.6248 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3822    0.9645    0.2843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9511    1.9683   -0.5445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8311    2.9375   -1.0552 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6140    2.0121   -0.8754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7325    1.0714   -0.3854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3825    1.0503   -0.6696 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3803   -0.1226   -0.8142 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7948    0.2285   -0.5603 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0835    1.0238    0.5215 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4108    1.3690    0.7823 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4391    0.9376   -0.0104 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7455    1.3158    0.3011 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1519    0.1410   -1.0942 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8302   -0.2014   -1.3520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0089   -4.3078   -0.9863 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2792   -3.7606    0.6902 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3833   -3.2482   -0.7049 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7811   -1.5419    0.7166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4402   -1.7210    2.0030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4260    0.8995    0.5653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9972    3.8109   -0.5358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2292    2.7928   -1.5315 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2758   -0.4610   -1.8658 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3121    1.4002    1.1911 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5979    1.9951    1.6408 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3422    0.7736    0.9085 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9673   -0.1975   -1.7176 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6430   -0.8313   -2.2159 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 15  3  1  0
 22 16  1  0
 13  6  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  8 27  1  0
  9 28  1  0
 11 29  1  0
 12 30  1  0
 15 31  1  0
 17 32  1  0
 18 33  1  0
 20 34  1  0
 21 35  1  0
 22 36  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       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000  -3.080   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       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
CONECT    1   21                                                            
CONECT    2    4    8                                                       
CONECT    3    5    8                                                       
CONECT    4    2    9                                                       
CONECT    5    3    9                                                       
CONECT    6   10   11                                                       
CONECT    7   10   12                                                       
CONECT    8    2    3   15                                                  
CONECT    9    4    5   17                                                  
CONECT   10    6    7   18                                                  
CONECT   11    6   13   19                                                  
CONECT   12    7   13   22                                                  
CONECT   13   11   12   14                                                  
CONECT   14   13   16   20                                                  
CONECT   15    8   16   22                                                  
CONECT   16   14   15   21                                                  
CONECT   17    9                                                            
CONECT   18   10                                                            
CONECT   19   11                                                            
CONECT   20   14                                                            
CONECT   21    1   16                                                       
CONECT   22   12   15                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

COMPND    HMDB0040560
HETATM    1  C1  UNL     1       0.352  -3.464  -0.363  1.00  0.00           C  
HETATM    2  O1  UNL     1      -0.455  -2.370  -0.662  1.00  0.00           O  
HETATM    3  C2  UNL     1      -0.078  -1.241   0.080  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.215  -0.881   0.928  1.00  0.00           C  
HETATM    5  O2  UNL     1      -1.328  -1.387   2.060  1.00  0.00           O  
HETATM    6  C4  UNL     1      -2.206   0.061   0.458  1.00  0.00           C  
HETATM    7  C5  UNL     1      -3.513  -0.015   0.805  1.00  0.00           C  
HETATM    8  O3  UNL     1      -3.980  -1.001   1.625  1.00  0.00           O  
HETATM    9  C6  UNL     1      -4.382   0.965   0.284  1.00  0.00           C  
HETATM   10  C7  UNL     1      -3.951   1.968  -0.545  1.00  0.00           C  
HETATM   11  O4  UNL     1      -4.831   2.938  -1.055  1.00  0.00           O  
HETATM   12  C8  UNL     1      -2.614   2.012  -0.875  1.00  0.00           C  
HETATM   13  C9  UNL     1      -1.733   1.071  -0.385  1.00  0.00           C  
HETATM   14  O5  UNL     1      -0.383   1.050  -0.670  1.00  0.00           O  
HETATM   15  C10 UNL     1       0.380  -0.123  -0.814  1.00  0.00           C  
HETATM   16  C11 UNL     1       1.795   0.228  -0.560  1.00  0.00           C  
HETATM   17  C12 UNL     1       2.084   1.024   0.522  1.00  0.00           C  
HETATM   18  C13 UNL     1       3.411   1.369   0.782  1.00  0.00           C  
HETATM   19  C14 UNL     1       4.439   0.938  -0.010  1.00  0.00           C  
HETATM   20  O6  UNL     1       5.746   1.316   0.301  1.00  0.00           O  
HETATM   21  C15 UNL     1       4.152   0.141  -1.094  1.00  0.00           C  
HETATM   22  C16 UNL     1       2.830  -0.201  -1.352  1.00  0.00           C  
HETATM   23  H1  UNL     1      -0.009  -4.308  -0.986  1.00  0.00           H  
HETATM   24  H2  UNL     1       0.279  -3.761   0.690  1.00  0.00           H  
HETATM   25  H3  UNL     1       1.383  -3.248  -0.705  1.00  0.00           H  
HETATM   26  H4  UNL     1       0.781  -1.542   0.717  1.00  0.00           H  
HETATM   27  H5  UNL     1      -3.440  -1.721   2.003  1.00  0.00           H  
HETATM   28  H6  UNL     1      -5.426   0.899   0.565  1.00  0.00           H  
HETATM   29  H7  UNL     1      -4.997   3.811  -0.536  1.00  0.00           H  
HETATM   30  H8  UNL     1      -2.229   2.793  -1.531  1.00  0.00           H  
HETATM   31  H9  UNL     1       0.276  -0.461  -1.866  1.00  0.00           H  
HETATM   32  H10 UNL     1       1.312   1.400   1.191  1.00  0.00           H  
HETATM   33  H11 UNL     1       3.598   1.995   1.641  1.00  0.00           H  
HETATM   34  H12 UNL     1       6.342   0.774   0.908  1.00  0.00           H  
HETATM   35  H13 UNL     1       4.967  -0.198  -1.718  1.00  0.00           H  
HETATM   36  H14 UNL     1       2.643  -0.831  -2.216  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3
CONECT    3    4   15   26
CONECT    4    5    5    6
CONECT    6    7    7   13
CONECT    7    8    9
CONECT    8   27
CONECT    9   10   10   28
CONECT   10   11   12
CONECT   11   29
CONECT   12   13   13   30
CONECT   13   14
CONECT   14   15
CONECT   15   16   31
CONECT   16   17   17   22
CONECT   17   18   32
CONECT   18   19   19   33
CONECT   19   20   21
CONECT   20   34
CONECT   21   22   22   35
CONECT   22   36
END

HMDB0040560
     RDKit          3D
4',5,7-Trihydroxy-3-methoxyflavanone
 36 38  0  0  0  0  0  0  0  0999 V2000
    0.3521   -3.4642   -0.3626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4553   -2.3704   -0.6623 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0782   -1.2412    0.0802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2149   -0.8808    0.9281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3280   -1.3873    2.0597 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2055    0.0607    0.4580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5129   -0.0149    0.8046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9803   -1.0006    1.6248 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3822    0.9645    0.2843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9511    1.9683   -0.5445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8311    2.9375   -1.0552 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6140    2.0121   -0.8754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7325    1.0714   -0.3854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3825    1.0503   -0.6696 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3803   -0.1226   -0.8142 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7948    0.2285   -0.5603 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0835    1.0238    0.5215 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4108    1.3690    0.7823 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4391    0.9376   -0.0104 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7455    1.3158    0.3011 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1519    0.1410   -1.0942 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8302   -0.2014   -1.3520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0089   -4.3078   -0.9863 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2792   -3.7606    0.6902 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3833   -3.2482   -0.7049 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7811   -1.5419    0.7166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4402   -1.7210    2.0030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4260    0.8995    0.5653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9972    3.8109   -0.5358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2292    2.7928   -1.5315 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2758   -0.4610   -1.8658 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3121    1.4002    1.1911 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5979    1.9951    1.6408 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3422    0.7736    0.9085 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9673   -0.1975   -1.7176 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6430   -0.8313   -2.2159 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 15  3  1  0
 22 16  1  0
 13  6  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  8 27  1  0
  9 28  1  0
 11 29  1  0
 12 30  1  0
 15 31  1  0
 17 32  1  0
 18 33  1  0
 20 34  1  0
 21 35  1  0
 22 36  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Aromadendrin 3-methyl ether	HMDB

Chemical Formula

C₁₆H₁₄O₆

Average Molecular Weight

302.2788

Monoisotopic Molecular Weight

302.07903818

IUPAC Name

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

Traditional Name

5,7-dihydroxy-2-(4-hydroxyphenyl)-3-methoxy-2,3-dihydro-1-benzopyran-4-one

CAS Registry Number

97231-20-4

SMILES

COC1C(OC2=CC(O)=CC(O)=C2C1=O)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C16H14O6/c1-21-16-14(20)13-11(19)6-10(18)7-12(13)22-15(16)8-2-4-9(17)5-3-8/h2-7,15-19H,1H3

InChI Key

JRLDUAGSJUMVDP-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C3 atom of the flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

O-methylated flavonoids

Direct Parent

3-O-methylated flavonoids

Alternative Parents

Substituents

3-methoxyflavonoid-skeleton
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavanone
Flavanonol
Hydroxyflavonoid
Flavan
Chromone
Chromane
Benzopyran
1-benzopyran
Aryl ketone
Aryl alkyl ketone
Phenol
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Vinylogous acid
Ketone
Organoheterocyclic compound
Oxacycle
Ether
Dialkyl ether
Organooxygen compound
Organic oxygen 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

Cell membrane (HMDB: HMDB0040560)

Cellular substructure

Membrane (HMDB: HMDB0040560)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0040560)

Source

Exogenous

Food

Food (HMDB: HMDB0040560)

Fruit

Drupe

European plum (FooDB: FOOD00147)

Fruits (FooDB: FOOD00871)

Endogenous

Plant

Plant (HMDB: HMDB0040560)

Not Available

Nutrient (HMDB: HMDB0040560)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	182 - 184 °C	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	0.24 g/L	ALOGPS
logP	2.51	ALOGPS
logP	2.76	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	7.8	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	96.22 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	77.38 m³·mol⁻¹	ChemAxon
Polarizability	30.13 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]+	171.134	31661259
DarkChem	[M-H]-	172.183	31661259
DeepCCS	[M+H]+	173.799	30932474
DeepCCS	[M-H]-	171.441	30932474
DeepCCS	[M-2H]-	204.551	30932474
DeepCCS	[M+Na]+	179.893	30932474
AllCCS	[M+H]+	170.7	32859911
AllCCS	[M+H-H2O]+	167.1	32859911
AllCCS	[M+NH4]+	174.1	32859911
AllCCS	[M+Na]+	175.1	32859911
AllCCS	[M-H]-	170.6	32859911
AllCCS	[M+Na-2H]-	170.0	32859911
AllCCS	[M+HCOO]-	169.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4',5,7-Trihydroxy-3-methoxyflavanone	COC1C(OC2=CC(O)=CC(O)=C2C1=O)C1=CC=C(O)C=C1	4131.2	Standard polar	33892256
4',5,7-Trihydroxy-3-methoxyflavanone	COC1C(OC2=CC(O)=CC(O)=C2C1=O)C1=CC=C(O)C=C1	2862.7	Standard non polar	33892256
4',5,7-Trihydroxy-3-methoxyflavanone	COC1C(OC2=CC(O)=CC(O)=C2C1=O)C1=CC=C(O)C=C1	2914.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4',5,7-Trihydroxy-3-methoxyflavanone,1TMS,isomer #1	COC1C(=O)C2=C(O)C=C(O[Si](C)(C)C)C=C2OC1C1=CC=C(O)C=C1	2787.2	Semi standard non polar	33892256
4',5,7-Trihydroxy-3-methoxyflavanone,1TMS,isomer #2	COC1C(=O)C2=C(C=C(O)C=C2O[Si](C)(C)C)OC1C1=CC=C(O)C=C1	2841.8	Semi standard non polar	33892256
4',5,7-Trihydroxy-3-methoxyflavanone,1TMS,isomer #3	COC1C(=O)C2=C(O)C=C(O)C=C2OC1C1=CC=C(O[Si](C)(C)C)C=C1	2817.9	Semi standard non polar	33892256
4',5,7-Trihydroxy-3-methoxyflavanone,2TMS,isomer #1	COC1C(=O)C2=C(C=C(O[Si](C)(C)C)C=C2O[Si](C)(C)C)OC1C1=CC=C(O)C=C1	2808.8	Semi standard non polar	33892256
4',5,7-Trihydroxy-3-methoxyflavanone,2TMS,isomer #2	COC1C(=O)C2=C(O)C=C(O[Si](C)(C)C)C=C2OC1C1=CC=C(O[Si](C)(C)C)C=C1	2787.3	Semi standard non polar	33892256
4',5,7-Trihydroxy-3-methoxyflavanone,2TMS,isomer #3	COC1C(=O)C2=C(C=C(O)C=C2O[Si](C)(C)C)OC1C1=CC=C(O[Si](C)(C)C)C=C1	2822.6	Semi standard non polar	33892256
4',5,7-Trihydroxy-3-methoxyflavanone,3TMS,isomer #1	COC1C(=O)C2=C(C=C(O[Si](C)(C)C)C=C2O[Si](C)(C)C)OC1C1=CC=C(O[Si](C)(C)C)C=C1	2851.6	Semi standard non polar	33892256
4',5,7-Trihydroxy-3-methoxyflavanone,1TBDMS,isomer #1	COC1C(=O)C2=C(O)C=C(O[Si](C)(C)C(C)(C)C)C=C2OC1C1=CC=C(O)C=C1	3063.9	Semi standard non polar	33892256
4',5,7-Trihydroxy-3-methoxyflavanone,1TBDMS,isomer #2	COC1C(=O)C2=C(C=C(O)C=C2O[Si](C)(C)C(C)(C)C)OC1C1=CC=C(O)C=C1	3108.8	Semi standard non polar	33892256
4',5,7-Trihydroxy-3-methoxyflavanone,1TBDMS,isomer #3	COC1C(=O)C2=C(O)C=C(O)C=C2OC1C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1	3093.6	Semi standard non polar	33892256
4',5,7-Trihydroxy-3-methoxyflavanone,2TBDMS,isomer #1	COC1C(=O)C2=C(C=C(O[Si](C)(C)C(C)(C)C)C=C2O[Si](C)(C)C(C)(C)C)OC1C1=CC=C(O)C=C1	3331.6	Semi standard non polar	33892256
4',5,7-Trihydroxy-3-methoxyflavanone,2TBDMS,isomer #2	COC1C(=O)C2=C(O)C=C(O[Si](C)(C)C(C)(C)C)C=C2OC1C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1	3298.7	Semi standard non polar	33892256
4',5,7-Trihydroxy-3-methoxyflavanone,2TBDMS,isomer #3	COC1C(=O)C2=C(C=C(O)C=C2O[Si](C)(C)C(C)(C)C)OC1C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1	3346.9	Semi standard non polar	33892256
4',5,7-Trihydroxy-3-methoxyflavanone,3TBDMS,isomer #1	COC1C(=O)C2=C(C=C(O[Si](C)(C)C(C)(C)C)C=C2O[Si](C)(C)C(C)(C)C)OC1C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1	3505.0	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4',5,7-Trihydroxy-3-methoxyflavanone GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-2291000000-67bbfaae5eacca7eb48e	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4',5,7-Trihydroxy-3-methoxyflavanone GC-MS (3 TMS) - 70eV, Positive	splash10-0w2a-3660960000-c80c5e192ab6921ccbfc	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4',5,7-Trihydroxy-3-methoxyflavanone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4',5,7-Trihydroxy-3-methoxyflavanone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4',5,7-Trihydroxy-3-methoxyflavanone 10V, Positive-QTOF	splash10-0udi-0119000000-48a22238f710ab9b4953	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4',5,7-Trihydroxy-3-methoxyflavanone 20V, Positive-QTOF	splash10-0udi-0943000000-a6da096fdfa945aa7ce3	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4',5,7-Trihydroxy-3-methoxyflavanone 40V, Positive-QTOF	splash10-0pk9-6900000000-7af939d82d115f41339b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4',5,7-Trihydroxy-3-methoxyflavanone 10V, Negative-QTOF	splash10-0udi-0009000000-158f06dd39141607ae6c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4',5,7-Trihydroxy-3-methoxyflavanone 20V, Negative-QTOF	splash10-0udi-1659000000-0e86c8d039c2aedd61d0	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4',5,7-Trihydroxy-3-methoxyflavanone 40V, Negative-QTOF	splash10-054x-3910000000-d81ad711ffd90d073969	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4',5,7-Trihydroxy-3-methoxyflavanone 10V, Negative-QTOF	splash10-0udi-0009000000-b74362932d87e15c9ce2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4',5,7-Trihydroxy-3-methoxyflavanone 20V, Negative-QTOF	splash10-0udi-0908000000-a33c540e1e4f32c0752f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4',5,7-Trihydroxy-3-methoxyflavanone 40V, Negative-QTOF	splash10-0002-0900000000-1f1d5f28d6abefdbdb67	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4',5,7-Trihydroxy-3-methoxyflavanone 10V, Positive-QTOF	splash10-0udi-0009000000-768be1604df899549999	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4',5,7-Trihydroxy-3-methoxyflavanone 20V, Positive-QTOF	splash10-0udi-0904000000-1c4752a08f2208a555cd	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4',5,7-Trihydroxy-3-methoxyflavanone 40V, Positive-QTOF	splash10-0udi-0900000000-28482acef80ed3292a4b	2021-09-22	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

FDB020336

KNApSAcK ID

C00008554

Chemspider ID

35014960

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14164881

PDB ID

Not Available

ChEBI ID

174888

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 4',5,7-Trihydroxy-3-methoxyflavanone (HMDB0040560)

MOL for HMDB0040560 (4',5,7-Trihydroxy-3-methoxyflavanone)

3D MOL for HMDB0040560 (4',5,7-Trihydroxy-3-methoxyflavanone)

3D SDF for HMDB0040560 (4',5,7-Trihydroxy-3-methoxyflavanone)

3D-SDF for HMDB0040560 (4',5,7-Trihydroxy-3-methoxyflavanone)

PDB for HMDB0040560 (4',5,7-Trihydroxy-3-methoxyflavanone)

3D PDB for HMDB0040560 (4',5,7-Trihydroxy-3-methoxyflavanone)

SMILES for HMDB0040560 (4',5,7-Trihydroxy-3-methoxyflavanone)

INCHI for HMDB0040560 (4',5,7-Trihydroxy-3-methoxyflavanone)

Structure for HMDB0040560 (4',5,7-Trihydroxy-3-methoxyflavanone)

3D Structure for HMDB0040560 (4',5,7-Trihydroxy-3-methoxyflavanone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra