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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:30:55 UTC

Update Date

2022-03-07 02:52:11 UTC

HMDB ID

HMDB0029522

Secondary Accession Numbers

HMDB29522

Metabolite Identification

Common Name

5,7-Dihydroxy-3-methoxyflavone

Description

5,7-Dihydroxy-3-methoxyflavone, also known as galangin 3-methyl ether or 3-methylgalangin, 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. Thus, 5,7-dihydroxy-3-methoxyflavone is considered to be a flavonoid. 5,7-Dihydroxy-3-methoxyflavone is found, on average, in the highest concentration within mexican oreganos (Lippia graveolens). 5,7-Dihydroxy-3-methoxyflavone has also been detected, but not quantified in, herbs and spices. This could make 5,7-dihydroxy-3-methoxyflavone a potential biomarker for the consumption of these foods. 5,7-Dihydroxy-3-methoxyflavone 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 very few articles have been published on 5,7-Dihydroxy-3-methoxyflavone.

Structure

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

HMDB0029522
     RDKit          3D
5,7-Dihydroxy-3-methoxyflavone
 33 35  0  0  0  0  0  0  0  0999 V2000
   -1.0103    3.1370   -1.1167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7422    2.4800    0.1231 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0041    1.3118    0.1697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5890    0.0831    0.1284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0323   -0.1641    0.0425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0095    0.7571    0.2246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3629    0.4333    0.0741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7558   -0.8434   -0.2659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7783   -1.7977   -0.4549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4708   -1.4484   -0.3011 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2059   -0.9915    0.1674 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4889   -0.9840    0.2434 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2562   -2.1413    0.2804 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6220   -2.0937    0.3619 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4201   -3.2290    0.4009 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2344   -0.8584    0.4075 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4933    0.2867    0.3720 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0906    1.5375    0.4168 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1317    0.2398    0.2907 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3971    1.4039    0.2547 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9327    2.5537    0.2950 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0419    3.5814   -1.0295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2979    3.9499   -1.3013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9548    2.3984   -1.9214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7667    1.7533    0.5175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0885    1.2046    0.2302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8025   -1.0761   -0.3779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0924   -2.8004   -0.7221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6923   -2.1948   -0.4494 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7412   -3.0804    0.2428 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0692   -4.1655    0.3731 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3215   -0.8256    0.4724 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0877    1.5828    0.4764 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
  4 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 20 21  2  0
 20  3  1  0
 10  5  1  0
 19 12  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  6 25  1  0
  7 26  1  0
  8 27  1  0
  9 28  1  0
 10 29  1  0
 13 30  1  0
 15 31  1  0
 16 32  1  0
 18 33  1  0
M  END


  Mrv0541 02241215142D          

 21 23  0  0  0  0            999 V2000
    1.7733    1.2370    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1133    0.8246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3708    1.2370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3708    2.0620    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1133    2.4745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5157    0.0004    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3708    0.0004    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3708    0.8246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1133    1.2370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1133    2.0620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7733    2.4745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5157    2.0620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5157    1.2370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7733    0.8246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7733   -1.2370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7733   -0.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1133    0.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3708   -0.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3708   -1.2370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1133   -1.6495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1133   -2.4745    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2 17  1  0  0  0  0
  3  4  1  0  0  0  0
  3  8  2  0  0  0  0
  4  5  1  0  0  0  0
  6 16  1  0  0  0  0
  7  8  1  0  0  0  0
  7 18  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 14  2  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  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
M  END
> <DATABASE_ID>
HMDB0029522

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(OC2=CC(O)=CC(O)=C2C1=O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H12O5/c1-20-16-14(19)13-11(18)7-10(17)8-12(13)21-15(16)9-5-3-2-4-6-9/h2-8,17-18H,1H3

> <INCHI_KEY>
LYISDADPVOHJBJ-UHFFFAOYSA-N

> <FORMULA>
C16H12O5

> <MOLECULAR_WEIGHT>
284.2635

> <EXACT_MASS>
284.068473494

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
28.43803415467274

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,7-dihydroxy-3-methoxy-2-phenyl-4H-chromen-4-one

> <ALOGPS_LOGP>
3.49

> <JCHEM_LOGP>
2.8762574966666667

> <ALOGPS_LOGS>
-3.63

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.113460799187116

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.442987877179501

> <JCHEM_PKA_STRONGEST_BASIC>
-4.8747114784658585

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
77.65160000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.63e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
galangin 3-methyl ether

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0029522
     RDKit          3D
5,7-Dihydroxy-3-methoxyflavone
 33 35  0  0  0  0  0  0  0  0999 V2000
   -1.0103    3.1370   -1.1167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7422    2.4800    0.1231 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0041    1.3118    0.1697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5890    0.0831    0.1284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0323   -0.1641    0.0425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0095    0.7571    0.2246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3629    0.4333    0.0741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7558   -0.8434   -0.2659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7783   -1.7977   -0.4549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4708   -1.4484   -0.3011 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2059   -0.9915    0.1674 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4889   -0.9840    0.2434 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2562   -2.1413    0.2804 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6220   -2.0937    0.3619 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4201   -3.2290    0.4009 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2344   -0.8584    0.4075 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4933    0.2867    0.3720 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0906    1.5375    0.4168 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1317    0.2398    0.2907 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3971    1.4039    0.2547 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9327    2.5537    0.2950 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0419    3.5814   -1.0295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2979    3.9499   -1.3013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9548    2.3984   -1.9214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7667    1.7533    0.5175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0885    1.2046    0.2302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8025   -1.0761   -0.3779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0924   -2.8004   -0.7221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6923   -2.1948   -0.4494 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7412   -3.0804    0.2428 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0692   -4.1655    0.3731 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3215   -0.8256    0.4724 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0877    1.5828    0.4764 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
  4 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 20 21  2  0
 20  3  1  0
 10  5  1  0
 19 12  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  6 25  1  0
  7 26  1  0
  8 27  1  0
  9 28  1  0
 10 29  1  0
 13 30  1  0
 15 31  1  0
 16 32  1  0
 18 33  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       3.310   2.309   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.078   1.539   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.692   2.309   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       0.692   3.849   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.078   4.619   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       4.696   0.001   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      -0.692   0.001   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -0.692   1.539   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.078   2.309   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.078   3.849   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.310   4.619   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.696   3.849   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.696   2.309   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.310   1.539   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.310  -2.309   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.310  -0.769   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.078   0.001   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.692  -0.769   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.692  -2.309   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.078  -3.079   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.078  -4.619   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   17                                                  
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4                                                            
CONECT    6   16                                                            
CONECT    7    8   18                                                       
CONECT    8    3    7    9                                                  
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14    9   13                                                       
CONECT   15   16   20                                                       
CONECT   16    6   15   17                                                  
CONECT   17    2   16   18                                                  
CONECT   18    7   17   19                                                  
CONECT   19   18   20                                                       
CONECT   20   15   19   21                                                  
CONECT   21   20                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    HMDB0029522
HETATM    1  C1  UNL     1      -1.010   3.137  -1.117  1.00  0.00           C  
HETATM    2  O1  UNL     1      -0.742   2.480   0.123  1.00  0.00           O  
HETATM    3  C2  UNL     1      -0.004   1.312   0.170  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.589   0.083   0.128  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.032  -0.164   0.043  1.00  0.00           C  
HETATM    6  C5  UNL     1      -3.009   0.757   0.225  1.00  0.00           C  
HETATM    7  C6  UNL     1      -4.363   0.433   0.074  1.00  0.00           C  
HETATM    8  C7  UNL     1      -4.756  -0.843  -0.266  1.00  0.00           C  
HETATM    9  C8  UNL     1      -3.778  -1.798  -0.455  1.00  0.00           C  
HETATM   10  C9  UNL     1      -2.471  -1.448  -0.301  1.00  0.00           C  
HETATM   11  O2  UNL     1       0.206  -0.991   0.167  1.00  0.00           O  
HETATM   12  C10 UNL     1       1.489  -0.984   0.243  1.00  0.00           C  
HETATM   13  C11 UNL     1       2.256  -2.141   0.280  1.00  0.00           C  
HETATM   14  C12 UNL     1       3.622  -2.094   0.362  1.00  0.00           C  
HETATM   15  O3  UNL     1       4.420  -3.229   0.401  1.00  0.00           O  
HETATM   16  C13 UNL     1       4.234  -0.858   0.408  1.00  0.00           C  
HETATM   17  C14 UNL     1       3.493   0.287   0.372  1.00  0.00           C  
HETATM   18  O4  UNL     1       4.091   1.537   0.417  1.00  0.00           O  
HETATM   19  C15 UNL     1       2.132   0.240   0.291  1.00  0.00           C  
HETATM   20  C16 UNL     1       1.397   1.404   0.255  1.00  0.00           C  
HETATM   21  O5  UNL     1       1.933   2.554   0.295  1.00  0.00           O  
HETATM   22  H1  UNL     1      -2.042   3.581  -1.030  1.00  0.00           H  
HETATM   23  H2  UNL     1      -0.298   3.950  -1.301  1.00  0.00           H  
HETATM   24  H3  UNL     1      -0.955   2.398  -1.921  1.00  0.00           H  
HETATM   25  H4  UNL     1      -2.767   1.753   0.518  1.00  0.00           H  
HETATM   26  H5  UNL     1      -5.089   1.205   0.230  1.00  0.00           H  
HETATM   27  H6  UNL     1      -5.802  -1.076  -0.378  1.00  0.00           H  
HETATM   28  H7  UNL     1      -4.092  -2.800  -0.722  1.00  0.00           H  
HETATM   29  H8  UNL     1      -1.692  -2.195  -0.449  1.00  0.00           H  
HETATM   30  H9  UNL     1       1.741  -3.080   0.243  1.00  0.00           H  
HETATM   31  H10 UNL     1       4.069  -4.165   0.373  1.00  0.00           H  
HETATM   32  H11 UNL     1       5.321  -0.826   0.472  1.00  0.00           H  
HETATM   33  H12 UNL     1       5.088   1.583   0.476  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3
CONECT    3    4    4   20
CONECT    4    5   11
CONECT    5    6    6   10
CONECT    6    7   25
CONECT    7    8    8   26
CONECT    8    9   27
CONECT    9   10   10   28
CONECT   10   29
CONECT   11   12
CONECT   12   13   13   19
CONECT   13   14   30
CONECT   14   15   16   16
CONECT   15   31
CONECT   16   17   32
CONECT   17   18   19   19
CONECT   18   33
CONECT   19   20
CONECT   20   21   21
END

HMDB0029522
     RDKit          3D
5,7-Dihydroxy-3-methoxyflavone
 33 35  0  0  0  0  0  0  0  0999 V2000
   -1.0103    3.1370   -1.1167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7422    2.4800    0.1231 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0041    1.3118    0.1697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5890    0.0831    0.1284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0323   -0.1641    0.0425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0095    0.7571    0.2246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3629    0.4333    0.0741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7558   -0.8434   -0.2659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7783   -1.7977   -0.4549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4708   -1.4484   -0.3011 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2059   -0.9915    0.1674 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4889   -0.9840    0.2434 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2562   -2.1413    0.2804 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6220   -2.0937    0.3619 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4201   -3.2290    0.4009 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2344   -0.8584    0.4075 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4933    0.2867    0.3720 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0906    1.5375    0.4168 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1317    0.2398    0.2907 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3971    1.4039    0.2547 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9327    2.5537    0.2950 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0419    3.5814   -1.0295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2979    3.9499   -1.3013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9548    2.3984   -1.9214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7667    1.7533    0.5175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0885    1.2046    0.2302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8025   -1.0761   -0.3779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0924   -2.8004   -0.7221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6923   -2.1948   -0.4494 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7412   -3.0804    0.2428 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0692   -4.1655    0.3731 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3215   -0.8256    0.4724 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0877    1.5828    0.4764 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
  4 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 20 21  2  0
 20  3  1  0
 10  5  1  0
 19 12  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  6 25  1  0
  7 26  1  0
  8 27  1  0
  9 28  1  0
 10 29  1  0
 13 30  1  0
 15 31  1  0
 16 32  1  0
 18 33  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Galangin 3-methyl ether	ChEBI
5,7-Dihydroxy-3-methoxy-2-phenyl-4H-1-benzopyran-4-one	Kegg
3-Methylgalangin	MeSH
5,7-Dihydroxy-3-methoxy-2-phenyl-4H-chromen-4-one	HMDB
5,7-Dihydroxy-3-methoxyflavone	ChEBI

Chemical Formula

C₁₆H₁₂O₅

Average Molecular Weight

284.2635

Monoisotopic Molecular Weight

284.068473494

IUPAC Name

5,7-dihydroxy-3-methoxy-2-phenyl-4H-chromen-4-one

Traditional Name

galangin 3-methyl ether

CAS Registry Number

6665-74-3

SMILES

COC1=C(OC2=CC(O)=CC(O)=C2C1=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C16H12O5/c1-20-16-14(19)13-11(18)7-10(17)8-12(13)21-15(16)9-5-3-2-4-6-9/h2-8,17-18H,1H3

InChI Key

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

dihydroxyflavone (CHEBI:1602 )
monomethoxyflavone (CHEBI:1602 )
flavonols (C11577 )
Flavones and Flavonols (LMPK12111654 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0029522)
Cell membrane (HMDB: HMDB0029522)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0029522)

Source

Endogenous

Endogenous (HMDB: HMDB0029522)

Plant

Plant (HMDB: HMDB0029522)

Exogenous

Food

Food (HMDB: HMDB0029522)

Herb and spice

Herb

Mexican oregano (FooDB: FOOD00102)

Herbs and Spices (FooDB: FOOD00866)

Exogenous (HMDB: HMDB0029522)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	299 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	336.3 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.066 g/L	ALOGPS
logP	3.49	ALOGPS
logP	2.88	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	6.44	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	77.65 m³·mol⁻¹	ChemAxon
Polarizability	28.44 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]+	164.547	30932474
DeepCCS	[M-H]-	162.189	30932474
DeepCCS	[M-2H]-	195.138	30932474
DeepCCS	[M+Na]+	170.64	30932474
AllCCS	[M+H]+	164.0	32859911
AllCCS	[M+H-H2O]+	160.1	32859911
AllCCS	[M+NH4]+	167.6	32859911
AllCCS	[M+Na]+	168.6	32859911
AllCCS	[M-H]-	164.8	32859911
AllCCS	[M+Na-2H]-	164.0	32859911
AllCCS	[M+HCOO]-	163.2	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.	7.24 minutes	32390414
Predicted by Siyang on May 30, 2022	15.0746 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.05 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2774.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	431.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	198.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	245.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	494.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	675.8 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	735.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	113.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1369.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	547.6 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	1564.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	410.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	521.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	420.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	259.1 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	88.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5,7-Dihydroxy-3-methoxyflavone	COC1=C(OC2=CC(O)=CC(O)=C2C1=O)C1=CC=CC=C1	4081.9	Standard polar	33892256
5,7-Dihydroxy-3-methoxyflavone	COC1=C(OC2=CC(O)=CC(O)=C2C1=O)C1=CC=CC=C1	2635.7	Standard non polar	33892256
5,7-Dihydroxy-3-methoxyflavone	COC1=C(OC2=CC(O)=CC(O)=C2C1=O)C1=CC=CC=C1	2739.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
5,7-Dihydroxy-3-methoxyflavone,1TMS,isomer #1	COC1=C(C2=CC=CC=C2)OC2=CC(O[Si](C)(C)C)=CC(O)=C2C1=O	2736.4	Semi standard non polar	33892256
5,7-Dihydroxy-3-methoxyflavone,1TMS,isomer #2	COC1=C(C2=CC=CC=C2)OC2=CC(O)=CC(O[Si](C)(C)C)=C2C1=O	2697.3	Semi standard non polar	33892256
5,7-Dihydroxy-3-methoxyflavone,2TMS,isomer #1	COC1=C(C2=CC=CC=C2)OC2=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C2C1=O	2738.4	Semi standard non polar	33892256
5,7-Dihydroxy-3-methoxyflavone,1TBDMS,isomer #1	COC1=C(C2=CC=CC=C2)OC2=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C2C1=O	2983.3	Semi standard non polar	33892256
5,7-Dihydroxy-3-methoxyflavone,1TBDMS,isomer #2	COC1=C(C2=CC=CC=C2)OC2=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C2C1=O	2945.9	Semi standard non polar	33892256
5,7-Dihydroxy-3-methoxyflavone,2TBDMS,isomer #1	COC1=C(C2=CC=CC=C2)OC2=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C2C1=O	3175.2	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 - 5,7-Dihydroxy-3-methoxyflavone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0019-0980000000-40965d7fa7571c58982c	2017-07-27	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5,7-Dihydroxy-3-methoxyflavone GC-MS (2 TMS) - 70eV, Positive	splash10-044i-3479600000-ac2b27802da118b5e460	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5,7-Dihydroxy-3-methoxyflavone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5,7-Dihydroxy-3-methoxyflavone 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 - 5,7-Dihydroxy-3-methoxyflavone 10V, Positive-QTOF	splash10-000i-0090000000-d1d6d620c716e8d78e49	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,7-Dihydroxy-3-methoxyflavone 20V, Positive-QTOF	splash10-000i-0090000000-1abf15fd1c5dd8e8129b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,7-Dihydroxy-3-methoxyflavone 40V, Positive-QTOF	splash10-0uxr-5790000000-3393b162a05d00da6e18	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,7-Dihydroxy-3-methoxyflavone 10V, Negative-QTOF	splash10-001i-0090000000-875cfdc42c4400b1eafa	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,7-Dihydroxy-3-methoxyflavone 20V, Negative-QTOF	splash10-001i-0090000000-70c109aa6f75af9a8692	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,7-Dihydroxy-3-methoxyflavone 40V, Negative-QTOF	splash10-0fsi-1950000000-b51e0725d704b4e9bce4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,7-Dihydroxy-3-methoxyflavone 10V, Negative-QTOF	splash10-001i-0090000000-1c01ef5aa5f04eb0a546	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,7-Dihydroxy-3-methoxyflavone 20V, Negative-QTOF	splash10-001i-0390000000-03e34ed2cb8f2fc7eb60	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,7-Dihydroxy-3-methoxyflavone 40V, Negative-QTOF	splash10-0fv0-3910000000-48ca0d2a9ce649295c0c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,7-Dihydroxy-3-methoxyflavone 10V, Positive-QTOF	splash10-000i-0090000000-51f99bf4d16155b2c7b0	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,7-Dihydroxy-3-methoxyflavone 20V, Positive-QTOF	splash10-000i-0090000000-e6b110f8170ddb7f89fd	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,7-Dihydroxy-3-methoxyflavone 40V, Positive-QTOF	splash10-0udr-1920000000-cbbb3db52b12c1967168	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5281946

PDB ID

Not Available

ChEBI ID

1602

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1810171

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 5,7-Dihydroxy-3-methoxyflavone (HMDB0029522)

MOL for HMDB0029522 (5,7-Dihydroxy-3-methoxyflavone)

3D MOL for HMDB0029522 (5,7-Dihydroxy-3-methoxyflavone)

3D SDF for HMDB0029522 (5,7-Dihydroxy-3-methoxyflavone)

3D-SDF for HMDB0029522 (5,7-Dihydroxy-3-methoxyflavone)

PDB for HMDB0029522 (5,7-Dihydroxy-3-methoxyflavone)

3D PDB for HMDB0029522 (5,7-Dihydroxy-3-methoxyflavone)

SMILES for HMDB0029522 (5,7-Dihydroxy-3-methoxyflavone)

INCHI for HMDB0029522 (5,7-Dihydroxy-3-methoxyflavone)

Structure for HMDB0029522 (5,7-Dihydroxy-3-methoxyflavone)

3D Structure for HMDB0029522 (5,7-Dihydroxy-3-methoxyflavone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra