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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:31:59 UTC

Update Date

2022-03-07 02:52:15 UTC

HMDB ID

HMDB0029676

Secondary Accession Numbers

HMDB29676

Metabolite Identification

Common Name

Diosmetin

Description

Diosmetin belongs to the class of organic compounds known as 4'-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C4' atom of the flavonoid backbone. Thus, diosmetin is considered to be a flavonoid. Diosmetin has been detected, but not quantified in, several different foods, such as sweet marjorams (Origanum majorana), rosemaries (Rosmarinus officinalis), common thymes (Thymus vulgaris), lemons (Citrus limon), and common oreganos (Origanum vulgare). This could make diosmetin a potential biomarker for the consumption of these foods. Diosmetin is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on Diosmetin.

Structure

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

HMDB0029676
     RDKit          3D
Diosmetin
 34 36  0  0  0  0  0  0  0  0999 V2000
    6.1811   -0.1435    0.7492 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2786    0.7624    0.1793 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9139    0.4870    0.1658 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4324   -0.6812    0.7133 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0692   -0.9841    0.7141 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1500   -0.1250    0.1665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2970   -0.3822    0.1343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8482   -1.5130    0.6545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2033   -1.7190    0.6063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6918   -2.7975    1.1066 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0162   -0.7656    0.0222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3953   -0.9588   -0.0353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0217   -2.0542    0.4580 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1559    0.0615   -0.6480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5253    1.1592   -1.1420 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3259    2.1494   -1.7437 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1638    1.3347   -1.0774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3915    0.3577   -0.4857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0979    0.5227   -0.4234 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6505    1.0504   -0.3824 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9955    1.3544   -0.3860 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4602    2.5331   -0.9407 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9802   -1.1563    0.3452 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1974    0.1305    0.3906 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1157   -0.1798    1.8529 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1225   -1.3872    1.1559 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7235   -1.9144    1.1544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2457   -2.2627    1.1096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8102   -2.8754    0.9055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2269   -0.1010   -0.6862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8848    2.9775   -2.1204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6939    2.2166   -1.4785 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9241    1.7255   -0.8132 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8004    3.1781   -1.3484 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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
  9 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
  6 20  1  0
 20 21  2  0
 21 22  1  0
 21  3  1  0
 19  7  1  0
 18 11  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  5 27  1  0
  8 28  1  0
 13 29  1  0
 14 30  1  0
 16 31  1  0
 17 32  1  0
 20 33  1  0
 22 34  1  0
M  END

  Mrv0541 02241218032D          

 22 24  0  0  0  0            999 V2000
   -0.3544   -0.2013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3620    0.2079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3657    1.0329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3468    1.4486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3431    2.2736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7720    2.2802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7758    1.4552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4921    1.0460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0632    1.0394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0670    0.2144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7833   -0.1948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4959    0.2210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2123   -0.1883    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7796   -2.2736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7833   -1.4486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0708   -1.0329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0745   -0.2079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7909    0.2013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5035   -0.2144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4997   -1.0394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2123   -1.4552    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2085   -2.2802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 10  1  0  0  0  0
  2  3  2  0  0  0  0
  2 17  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  9  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  8 12  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 20  2  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0029676

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(O)C=C(C=C1)C1=CC(=O)C2=C(O1)C=C(O)C=C2O

> <INCHI_IDENTIFIER>
InChI=1S/C16H12O6/c1-21-13-3-2-8(4-10(13)18)14-7-12(20)16-11(19)5-9(17)6-15(16)22-14/h2-7,17-19H,1H3

> <INCHI_KEY>
MBNGWHIJMBWFHU-UHFFFAOYSA-N

> <FORMULA>
C16H12O6

> <MOLECULAR_WEIGHT>
300.2629

> <EXACT_MASS>
300.063388116

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
29.83669989946849

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4H-chromen-4-one

> <ALOGPS_LOGP>
3.06

> <JCHEM_LOGP>
2.5490178679999995

> <ALOGPS_LOGS>
-3.60

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.1188900746853

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.637302029241538

> <JCHEM_PKA_STRONGEST_BASIC>
-4.774841182860492

> <JCHEM_POLAR_SURFACE_AREA>
96.22000000000001

> <JCHEM_REFRACTIVITY>
79.37710000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.54e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
diosmetin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0029676
     RDKit          3D
Diosmetin
 34 36  0  0  0  0  0  0  0  0999 V2000
    6.1811   -0.1435    0.7492 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2786    0.7624    0.1793 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9139    0.4870    0.1658 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4324   -0.6812    0.7133 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0692   -0.9841    0.7141 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1500   -0.1250    0.1665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2970   -0.3822    0.1343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8482   -1.5130    0.6545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2033   -1.7190    0.6063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6918   -2.7975    1.1066 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0162   -0.7656    0.0222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3953   -0.9588   -0.0353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0217   -2.0542    0.4580 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1559    0.0615   -0.6480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5253    1.1592   -1.1420 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3259    2.1494   -1.7437 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1638    1.3347   -1.0774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3915    0.3577   -0.4857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0979    0.5227   -0.4234 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6505    1.0504   -0.3824 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9955    1.3544   -0.3860 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4602    2.5331   -0.9407 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9802   -1.1563    0.3452 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1974    0.1305    0.3906 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1157   -0.1798    1.8529 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1225   -1.3872    1.1559 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7235   -1.9144    1.1544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2457   -2.2627    1.1096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8102   -2.8754    0.9055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2269   -0.1010   -0.6862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8848    2.9775   -2.1204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6939    2.2166   -1.4785 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9241    1.7255   -0.8132 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8004    3.1781   -1.3484 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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
  9 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
  6 20  1  0
 20 21  2  0
 21 22  1  0
 21  3  1  0
 19  7  1  0
 18 11  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  5 27  1  0
  8 28  1  0
 13 29  1  0
 14 30  1  0
 16 31  1  0
 17 32  1  0
 20 33  1  0
 22 34  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0      -0.662  -0.376   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.676   0.388   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.683   1.928   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.647   2.704   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -0.640   4.244   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      -3.308   4.256   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -3.315   2.716   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.652   1.953   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.985   1.940   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.992   0.400   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.329  -0.364   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.659   0.413   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -5.996  -0.351   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       3.322  -4.244   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       3.329  -2.704   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.999  -1.928   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.006  -0.388   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.343   0.376   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.673  -0.400   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.666  -1.940   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       5.996  -2.716   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       5.989  -4.256   0.000  0.00  0.00           C+0
CONECT    1    2   10                                                       
CONECT    2    1    3   17                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4                                                            
CONECT    6    7                                                            
CONECT    7    6    8    9                                                  
CONECT    8    7   12                                                       
CONECT    9    4    7   10                                                  
CONECT   10    1    9   11                                                  
CONECT   11   10   12                                                       
CONECT   12    8   11   13                                                  
CONECT   13   12                                                            
CONECT   14   15                                                            
CONECT   15   14   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17    2   16   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   15   19   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

COMPND    HMDB0029676
HETATM    1  C1  UNL     1       6.181  -0.144   0.749  1.00  0.00           C  
HETATM    2  O1  UNL     1       5.279   0.762   0.179  1.00  0.00           O  
HETATM    3  C2  UNL     1       3.914   0.487   0.166  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.432  -0.681   0.713  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.069  -0.984   0.714  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.150  -0.125   0.167  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.297  -0.382   0.134  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.848  -1.513   0.654  1.00  0.00           C  
HETATM    9  C8  UNL     1      -2.203  -1.719   0.606  1.00  0.00           C  
HETATM   10  O2  UNL     1      -2.692  -2.798   1.107  1.00  0.00           O  
HETATM   11  C9  UNL     1      -3.016  -0.766   0.022  1.00  0.00           C  
HETATM   12  C10 UNL     1      -4.395  -0.959  -0.035  1.00  0.00           C  
HETATM   13  O3  UNL     1      -5.022  -2.054   0.458  1.00  0.00           O  
HETATM   14  C11 UNL     1      -5.156   0.061  -0.648  1.00  0.00           C  
HETATM   15  C12 UNL     1      -4.525   1.159  -1.142  1.00  0.00           C  
HETATM   16  O4  UNL     1      -5.326   2.149  -1.744  1.00  0.00           O  
HETATM   17  C13 UNL     1      -3.164   1.335  -1.077  1.00  0.00           C  
HETATM   18  C14 UNL     1      -2.391   0.358  -0.486  1.00  0.00           C  
HETATM   19  O5  UNL     1      -1.098   0.523  -0.423  1.00  0.00           O  
HETATM   20  C15 UNL     1       1.650   1.050  -0.382  1.00  0.00           C  
HETATM   21  C16 UNL     1       2.996   1.354  -0.386  1.00  0.00           C  
HETATM   22  O6  UNL     1       3.460   2.533  -0.941  1.00  0.00           O  
HETATM   23  H1  UNL     1       5.980  -1.156   0.345  1.00  0.00           H  
HETATM   24  H2  UNL     1       7.197   0.131   0.391  1.00  0.00           H  
HETATM   25  H3  UNL     1       6.116  -0.180   1.853  1.00  0.00           H  
HETATM   26  H4  UNL     1       4.122  -1.387   1.156  1.00  0.00           H  
HETATM   27  H5  UNL     1       1.723  -1.914   1.154  1.00  0.00           H  
HETATM   28  H6  UNL     1      -0.246  -2.263   1.110  1.00  0.00           H  
HETATM   29  H7  UNL     1      -4.810  -2.875   0.905  1.00  0.00           H  
HETATM   30  H8  UNL     1      -6.227  -0.101  -0.686  1.00  0.00           H  
HETATM   31  H9  UNL     1      -4.885   2.978  -2.120  1.00  0.00           H  
HETATM   32  H10 UNL     1      -2.694   2.217  -1.479  1.00  0.00           H  
HETATM   33  H11 UNL     1       0.924   1.725  -0.813  1.00  0.00           H  
HETATM   34  H12 UNL     1       2.800   3.178  -1.348  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3
CONECT    3    4    4   21
CONECT    4    5   26
CONECT    5    6    6   27
CONECT    6    7   20
CONECT    7    8    8   19
CONECT    8    9   28
CONECT    9   10   10   11
CONECT   11   12   12   18
CONECT   12   13   14
CONECT   13   29
CONECT   14   15   15   30
CONECT   15   16   17
CONECT   16   31
CONECT   17   18   18   32
CONECT   18   19
CONECT   20   21   21   33
CONECT   21   22
CONECT   22   34
END

HMDB0029676
     RDKit          3D
Diosmetin
 34 36  0  0  0  0  0  0  0  0999 V2000
    6.1811   -0.1435    0.7492 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2786    0.7624    0.1793 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9139    0.4870    0.1658 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4324   -0.6812    0.7133 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0692   -0.9841    0.7141 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1500   -0.1250    0.1665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2970   -0.3822    0.1343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8482   -1.5130    0.6545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2033   -1.7190    0.6063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6918   -2.7975    1.1066 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0162   -0.7656    0.0222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3953   -0.9588   -0.0353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0217   -2.0542    0.4580 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1559    0.0615   -0.6480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5253    1.1592   -1.1420 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3259    2.1494   -1.7437 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1638    1.3347   -1.0774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3915    0.3577   -0.4857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0979    0.5227   -0.4234 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6505    1.0504   -0.3824 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9955    1.3544   -0.3860 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4602    2.5331   -0.9407 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9802   -1.1563    0.3452 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1974    0.1305    0.3906 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1157   -0.1798    1.8529 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1225   -1.3872    1.1559 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7235   -1.9144    1.1544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2457   -2.2627    1.1096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8102   -2.8754    0.9055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2269   -0.1010   -0.6862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8848    2.9775   -2.1204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6939    2.2166   -1.4785 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9241    1.7255   -0.8132 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8004    3.1781   -1.3484 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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
  9 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
  6 20  1  0
 20 21  2  0
 21 22  1  0
 21  3  1  0
 19  7  1  0
 18 11  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  5 27  1  0
  8 28  1  0
 13 29  1  0
 14 30  1  0
 16 31  1  0
 17 32  1  0
 20 33  1  0
 22 34  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3',5,7-Trihydroxy-4'-methoxyflavone	ChEBI
5,7-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-benzopyrone	ChEBI
5,7-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4H-1-benzopyran-4-one	ChEBI
Luteolin 4'-methyl ether	ChEBI
Salinigricoflavonol	ChEBI
4'-Methylluteolin	HMDB
5,7,3'-Trihydroxy-4'-methoxyflavone	HMDB
Vitamin P	HMDB

Chemical Formula

C₁₆H₁₂O₆

Average Molecular Weight

300.2629

Monoisotopic Molecular Weight

300.063388116

IUPAC Name

5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4H-chromen-4-one

Traditional Name

diosmetin

CAS Registry Number

520-34-3

SMILES

COC1=C(O)C=C(C=C1)C1=CC(=O)C2=C(O1)C=C(O)C=C2O

InChI Identifier

InChI=1S/C16H12O6/c1-21-13-3-2-8(4-10(13)18)14-7-12(20)16-11(19)5-9(17)6-15(16)22-14/h2-7,17-19H,1H3

InChI Key

MBNGWHIJMBWFHU-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 4'-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C4' atom of the flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

O-methylated flavonoids

Direct Parent

4'-O-methylated flavonoids

Alternative Parents

Substituents

4p-methoxyflavonoid-skeleton
3'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavone
Hydroxyflavonoid
Chromone
Benzopyran
Methoxyphenol
1-benzopyran
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Pyranone
Monocyclic benzene moiety
Benzenoid
Pyran
Vinylogous acid
Heteroaromatic compound
Organoheterocyclic compound
Ether
Oxacycle
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

monomethoxyflavone (CHEBI:4630 )
trihydroxyflavone (CHEBI:4630 )
3'-hydroxyflavonoid (CHEBI:4630 )
flavones (C10038 )
Flavones and Flavonols (C10038 )
Flavones and Flavonols (LMPK12110824 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0029676)
Cell membrane (HMDB: HMDB0029676)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0029676)

Source

Exogenous

Exogenous (HMDB: HMDB0029676)

Food

Food (HMDB: HMDB0029676)

Lemon (FooDB: FOOD00054)
Citrus (FooDB: FOOD00859)

Endogenous

Endogenous (HMDB: HMDB0029676)

Plant

Plant (HMDB: HMDB0029676)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0029676)

Antineoplastic agent

Cancer preventive (HMDB: HMDB0029676)

Manufacturing industry

Material processing agent

Solid material processing agent

Protective agent

Antioxidant (HMDB: HMDB0029676)
Antioxidant (HMDB: HMDB0029676)

Antiviral agent (HMDB: HMDB0029676)

Biological role

Modulator

Inhibitor

EC 1.1.1.21 (aldehyde reductase) inhibitor (HMDB: HMDB0029676)

Enzyme inhibitor

Peroxisome proliferator activated receptor gamma antagonist (HMDB: HMDB0029676)
TNF-alpha inhibitor (HMDB: HMDB0029676)

Nitric-oxide inhibitor (HMDB: HMDB0029676)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	228 - 230 °C	Not Available
Boiling Point	576.70 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	104.7 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	3.10	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	164.785	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001489

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.075 g/L	ALOGPS
logP	3.06	ALOGPS
logP	2.55	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	6.64	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	96.22 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	79.38 m³·mol⁻¹	ChemAxon
Polarizability	29.84 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]+	172.348	30932474
DeepCCS	[M-H]-	169.99	30932474
DeepCCS	[M-2H]-	203.632	30932474
DeepCCS	[M+Na]+	178.859	30932474
AllCCS	[M+H]+	168.5	32859911
AllCCS	[M+H-H2O]+	164.8	32859911
AllCCS	[M+NH4]+	172.0	32859911
AllCCS	[M+Na]+	172.9	32859911
AllCCS	[M-H]-	168.8	32859911
AllCCS	[M+Na-2H]-	168.1	32859911
AllCCS	[M+HCOO]-	167.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Diosmetin	COC1=C(O)C=C(C=C1)C1=CC(=O)C2=C(O1)C=C(O)C=C2O	4937.0	Standard polar	33892256
Diosmetin	COC1=C(O)C=C(C=C1)C1=CC(=O)C2=C(O1)C=C(O)C=C2O	3146.9	Standard non polar	33892256
Diosmetin	COC1=C(O)C=C(C=C1)C1=CC(=O)C2=C(O1)C=C(O)C=C2O	3283.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Diosmetin,1TMS,isomer #1	COC1=CC=C(C2=CC(=O)C3=C(O)C=C(O)C=C3O2)C=C1O[Si](C)(C)C	3262.0	Semi standard non polar	33892256
Diosmetin,1TMS,isomer #2	COC1=CC=C(C2=CC(=O)C3=C(O)C=C(O[Si](C)(C)C)C=C3O2)C=C1O	3333.5	Semi standard non polar	33892256
Diosmetin,1TMS,isomer #3	COC1=CC=C(C2=CC(=O)C3=C(O[Si](C)(C)C)C=C(O)C=C3O2)C=C1O	3283.8	Semi standard non polar	33892256
Diosmetin,2TMS,isomer #1	COC1=CC=C(C2=CC(=O)C3=C(O[Si](C)(C)C)C=C(O)C=C3O2)C=C1O[Si](C)(C)C	3140.9	Semi standard non polar	33892256
Diosmetin,2TMS,isomer #2	COC1=CC=C(C2=CC(=O)C3=C(O)C=C(O[Si](C)(C)C)C=C3O2)C=C1O[Si](C)(C)C	3212.0	Semi standard non polar	33892256
Diosmetin,2TMS,isomer #3	COC1=CC=C(C2=CC(=O)C3=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C=C3O2)C=C1O	3269.3	Semi standard non polar	33892256
Diosmetin,3TMS,isomer #1	COC1=CC=C(C2=CC(=O)C3=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C=C3O2)C=C1O[Si](C)(C)C	3153.8	Semi standard non polar	33892256
Diosmetin,1TBDMS,isomer #1	COC1=CC=C(C2=CC(=O)C3=C(O)C=C(O)C=C3O2)C=C1O[Si](C)(C)C(C)(C)C	3518.5	Semi standard non polar	33892256
Diosmetin,1TBDMS,isomer #2	COC1=CC=C(C2=CC(=O)C3=C(O)C=C(O[Si](C)(C)C(C)(C)C)C=C3O2)C=C1O	3599.4	Semi standard non polar	33892256
Diosmetin,1TBDMS,isomer #3	COC1=CC=C(C2=CC(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(O)C=C3O2)C=C1O	3556.7	Semi standard non polar	33892256
Diosmetin,2TBDMS,isomer #1	COC1=CC=C(C2=CC(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(O)C=C3O2)C=C1O[Si](C)(C)C(C)(C)C	3656.5	Semi standard non polar	33892256
Diosmetin,2TBDMS,isomer #2	COC1=CC=C(C2=CC(=O)C3=C(O)C=C(O[Si](C)(C)C(C)(C)C)C=C3O2)C=C1O[Si](C)(C)C(C)(C)C	3744.4	Semi standard non polar	33892256
Diosmetin,2TBDMS,isomer #3	COC1=CC=C(C2=CC(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)C=C3O2)C=C1O	3767.6	Semi standard non polar	33892256
Diosmetin,3TBDMS,isomer #1	COC1=CC=C(C2=CC(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)C=C3O2)C=C1O[Si](C)(C)C(C)(C)C	3897.9	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 - Diosmetin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0kh9-0492000000-c9cb489c6e399645f54f	2017-07-27	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Diosmetin GC-MS (3 TMS) - 70eV, Positive	splash10-0ukc-2190860000-1029bf37ad921c9a81e8	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Diosmetin 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 - Diosmetin ESI-TOF 20V, Negative-QTOF	splash10-014u-0000700009-50048523dd30a3c69126	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diosmetin ESI-TOF 10V, Negative-QTOF	splash10-014u-0000700009-50048523dd30a3c69126	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diosmetin ESI-TOF 50V, Negative-QTOF	splash10-057i-0490000000-9c04ed66f8f3ed9e2ed8	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diosmetin ESI-TOF 40V, Negative-QTOF	splash10-001i-0190000000-77edda567cd76512c52d	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diosmetin ESI-TOF 20V, Negative-QTOF	splash10-001i-0090000000-675379707ad9e98244a9	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diosmetin ESI-TOF 10V, Negative-QTOF	splash10-0002-0091000000-188fb9f96e76251ce539	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diosmetin ESI-TOF 50V, Negative-QTOF	splash10-057i-0490000000-9c04ed66f8f3ed9e2ed8	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diosmetin ESI-TOF 40V, Negative-QTOF	splash10-001i-0190000000-77edda567cd76512c52d	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diosmetin LC-ESI-ITTOF , negative-QTOF	splash10-001i-0090000000-ae5188debe4910fab9c6	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diosmetin Linear Ion Trap , negative-QTOF	splash10-001i-0090000000-6e1198f4157cda4df0ac	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diosmetin Linear Ion Trap , negative-QTOF	splash10-001i-0090000000-b23157e3c53d703e88d1	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diosmetin LC-ESI-TOF , negative-QTOF	splash10-001i-0090000000-675379707ad9e98244a9	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diosmetin LC-ESI-TOF , negative-QTOF	splash10-057i-0490000000-9c04ed66f8f3ed9e2ed8	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diosmetin LC-ESI-TOF , negative-QTOF	splash10-001i-0190000000-77edda567cd76512c52d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diosmetin Linear Ion Trap , positive-QTOF	splash10-000i-0094000000-0b3f48256d5c0ee7fb1b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diosmetin LC-ESI-QFT 21V, positive-QTOF	splash10-000i-0092000000-0448ee3b6390176e376a	2020-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diosmetin LC-ESI-IT 21V, positive-QTOF	splash10-000i-0090000000-8bb45858bd3dc65a5c07	2020-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diosmetin 6V, Negative-QTOF	splash10-0002-0190000000-15ab8c66562248b310ee	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diosmetin 40V, Positive-QTOF	splash10-0a4i-0290000000-2ce24609e65e5b7d0d11	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diosmetin 10V, Positive-QTOF	splash10-0udi-0009000000-a4a0986393c64d566f91	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diosmetin 20V, Positive-QTOF	splash10-0udi-0019000000-9488c8767caac5f6b9b5	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diosmetin 40V, Positive-QTOF	splash10-0ufr-2590000000-e4455d0da36912d7b96a	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diosmetin 10V, Negative-QTOF	splash10-0002-0090000000-91f51b4b036d4731f305	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diosmetin 20V, Negative-QTOF	splash10-0002-0090000000-b6f4a2a03e7355f95b1c	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diosmetin 40V, Negative-QTOF	splash10-0ue9-0390000000-e296a45296f81b0f1454	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

DB11259

Phenol Explorer Compound ID

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Diosmetin

METLIN ID

Not Available

PubChem Compound

5281612

PDB ID

Not Available

ChEBI ID

4630

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1700891

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

Diosmetin → 3,4,5-trihydroxy-6-{[7-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-oxo-4H-chromen-5-yl]oxy}oxane-2-carboxylic acid	details
Diosmetin → Diosmetin 7-O-beta-D-glucuronopyranoside	details
Diosmetin → 6-[5-(5,7-dihydroxy-4-oxo-4H-chromen-2-yl)-2-methoxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid	details

Enzyme Details

2. Sulfotransferase 1A3

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

Reactions

Diosmetin → [5-(5,7-dihydroxy-4-oxo-4H-chromen-2-yl)-2-methoxyphenyl]oxidanesulfonic acid	details

Showing metabocard for Diosmetin (HMDB0029676)

MOL for HMDB0029676 (Diosmetin)

3D MOL for HMDB0029676 (Diosmetin)

3D SDF for HMDB0029676 (Diosmetin)

3D-SDF for HMDB0029676 (Diosmetin)

PDB for HMDB0029676 (Diosmetin)

3D PDB for HMDB0029676 (Diosmetin)

SMILES for HMDB0029676 (Diosmetin)

INCHI for HMDB0029676 (Diosmetin)

Structure for HMDB0029676 (Diosmetin)

3D Structure for HMDB0029676 (Diosmetin)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions

Reactions