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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 22:42:31 UTC

Update Date

2022-03-07 02:55:20 UTC

HMDB ID

HMDB0037458

Secondary Accession Numbers

HMDB37458

Metabolite Identification

Common Name

5-Hydroxy-4',7,8-trimethoxyflavone

Description

5-Hydroxy-4',7,8-trimethoxyflavone belongs to the class of organic compounds known as 8-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C8 atom of the flavonoid backbone. Thus, 5-hydroxy-4',7,8-trimethoxyflavone is considered to be a flavonoid. 5-Hydroxy-4',7,8-trimethoxyflavone has been detected, but not quantified in, citrus and mandarin orange (clementine, tangerine). This could make 5-hydroxy-4',7,8-trimethoxyflavone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 5-Hydroxy-4',7,8-trimethoxyflavone.

Structure

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

HMDB0037458
     RDKit          3D
5-Hydroxy-4',7,8-trimethoxyflavone
 40 42  0  0  0  0  0  0  0  0999 V2000
    7.1180   -0.6734    0.7744 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8743   -1.0105    1.2949 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6557   -0.6201    0.8222 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5523    0.1935   -0.2820 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2715    0.5542   -0.7109 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1272    0.1317   -0.0790 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7769    0.5068   -0.5242 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5350    1.3113   -1.6093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7366    1.6758   -2.0439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9035    2.4089   -3.0354 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8090    1.1944   -1.3351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1172    1.4826   -1.6639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4732    2.2649   -2.7131 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1833    0.9607   -0.9001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8655    0.1650    0.1692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8576   -0.3965    0.9834 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2201   -0.1296    0.6863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5675   -0.1182    0.4918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2542   -0.9324    1.5866 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1484   -2.3092    1.3438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5044    0.3831   -0.2438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2865    0.0731    0.1192 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2473   -0.6972    1.0452 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5134   -1.0521    1.4672 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2247    0.4170    0.5699 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9150   -0.9260    1.5066 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3286   -1.1919   -0.1825 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4409    0.5382   -0.7953 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2120    1.1890   -1.5734 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3793    1.7037   -2.1857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9428    2.7231   -3.3639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2023    1.1789   -1.1477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8388   -0.6861    1.4460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5153   -0.4674   -0.3139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4005    0.9453    0.8751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8776   -2.5410    0.2831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0974   -2.7996    1.6003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3537   -2.7026    2.0372 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3529   -1.0477    1.5670 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6305   -1.6995    2.3439 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
 16 17  1  0
 15 18  1  0
 18 19  1  0
 19 20  1  0
 18 21  2  0
 21 22  1  0
  6 23  1  0
 23 24  2  0
 24  3  1  0
 22  7  1  0
 21 11  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  5 29  1  0
  8 30  1  0
 13 31  1  0
 14 32  1  0
 17 33  1  0
 17 34  1  0
 17 35  1  0
 20 36  1  0
 20 37  1  0
 20 38  1  0
 23 39  1  0
 24 40  1  0
M  END


  Mrv0541 02241219312D          

 24 26  0  0  0  0            999 V2000
   -0.3568   -0.6187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717    0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7853    1.0311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7853    1.8561    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -1.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7867   -1.8561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5003   -1.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5003   -0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7867   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3568   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3568    0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3568    1.0311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3568    1.8561    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2152   -1.8561    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7853   -1.4437    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7853   -0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5003   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5003    0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2152   -0.6187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9288   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9288   -1.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5003   -1.8561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 12  1  0  0  0  0
  2  3  2  0  0  0  0
  2 18  1  0  0  0  0
  3  4  1  0  0  0  0
  3 14  1  0  0  0  0
  4  5  1  0  0  0  0
  4 20  2  0  0  0  0
  6  7  1  0  0  0  0
  6 11  2  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 16  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  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
 14 15  2  0  0  0  0
 16 23  1  0  0  0  0
 17 18  1  0  0  0  0
 17 24  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0037458

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C18H16O6/c1-21-11-6-4-10(5-7-11)14-8-12(19)16-13(20)9-15(22-2)17(23-3)18(16)24-14/h4-9,20H,1-3H3

> <INCHI_KEY>
RRZRJBICWWNHRB-UHFFFAOYSA-N

> <FORMULA>
C18H16O6

> <MOLECULAR_WEIGHT>
328.316

> <EXACT_MASS>
328.094688244

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
33.746972429048654

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-hydroxy-7,8-dimethoxy-2-(4-methoxyphenyl)-4H-chromen-4-one

> <ALOGPS_LOGP>
3.31

> <JCHEM_LOGP>
2.84080598

> <ALOGPS_LOGS>
-4.16

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.18772604889555

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.080451106285

> <JCHEM_PKA_STRONGEST_BASIC>
-4.385599865757411

> <JCHEM_POLAR_SURFACE_AREA>
74.22000000000001

> <JCHEM_REFRACTIVITY>
88.3417

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.27e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-hydroxy-7,8-dimethoxy-2-(4-methoxyphenyl)chromen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0037458
     RDKit          3D
5-Hydroxy-4',7,8-trimethoxyflavone
 40 42  0  0  0  0  0  0  0  0999 V2000
    7.1180   -0.6734    0.7744 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8743   -1.0105    1.2949 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6557   -0.6201    0.8222 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5523    0.1935   -0.2820 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2715    0.5542   -0.7109 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1272    0.1317   -0.0790 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7769    0.5068   -0.5242 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5350    1.3113   -1.6093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7366    1.6758   -2.0439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9035    2.4089   -3.0354 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8090    1.1944   -1.3351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1172    1.4826   -1.6639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4732    2.2649   -2.7131 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1833    0.9607   -0.9001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8655    0.1650    0.1692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8576   -0.3965    0.9834 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2201   -0.1296    0.6863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5675   -0.1182    0.4918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2542   -0.9324    1.5866 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1484   -2.3092    1.3438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5044    0.3831   -0.2438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2865    0.0731    0.1192 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2473   -0.6972    1.0452 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5134   -1.0521    1.4672 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2247    0.4170    0.5699 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9150   -0.9260    1.5066 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3286   -1.1919   -0.1825 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4409    0.5382   -0.7953 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2120    1.1890   -1.5734 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3793    1.7037   -2.1857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9428    2.7231   -3.3639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2023    1.1789   -1.1477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8388   -0.6861    1.4460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5153   -0.4674   -0.3139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4005    0.9453    0.8751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8776   -2.5410    0.2831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0974   -2.7996    1.6003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3537   -2.7026    2.0372 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3529   -1.0477    1.5670 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6305   -1.6995    2.3439 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
 16 17  1  0
 15 18  1  0
 18 19  1  0
 19 20  1  0
 18 21  2  0
 21 22  1  0
  6 23  1  0
 23 24  2  0
 24  3  1  0
 22  7  1  0
 21 11  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  5 29  1  0
  8 30  1  0
 13 31  1  0
 14 32  1  0
 17 33  1  0
 17 34  1  0
 17 35  1  0
 20 36  1  0
 20 37  1  0
 20 38  1  0
 23 39  1  0
 24 40  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      -0.666  -1.155   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -2.001  -0.385   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.001   1.155   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.333   1.925   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -3.333   3.465   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       2.001  -2.695   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.335  -3.465   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.667  -2.695   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.667  -1.155   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.335  -0.385   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.001  -1.155   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.666  -0.385   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.666   1.155   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.666   1.925   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -0.666   3.465   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       6.002  -3.465   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -3.333  -2.695   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -3.333  -1.155   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.667  -0.385   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -4.667   1.155   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -6.002  -1.155   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -7.334  -0.385   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.334  -2.695   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -4.667  -3.465   0.000  0.00  0.00           C+0
CONECT    1    2   12                                                       
CONECT    2    1    3   18                                                  
CONECT    3    2    4   14                                                  
CONECT    4    3    5   20                                                  
CONECT    5    4                                                            
CONECT    6    7   11                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   16                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11    6   10   12                                                  
CONECT   12    1   11   13                                                  
CONECT   13   12   14                                                       
CONECT   14    3   13   15                                                  
CONECT   15   14                                                            
CONECT   16    8   23                                                       
CONECT   17   18   24                                                       
CONECT   18    2   17   19                                                  
CONECT   19   18   20   21                                                  
CONECT   20    4   19                                                       
CONECT   21   19   22                                                       
CONECT   22   21                                                            
CONECT   23   16                                                            
CONECT   24   17                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

COMPND    HMDB0037458
HETATM    1  C1  UNL     1       7.118  -0.673   0.774  1.00  0.00           C  
HETATM    2  O1  UNL     1       5.874  -1.011   1.295  1.00  0.00           O  
HETATM    3  C2  UNL     1       4.656  -0.620   0.822  1.00  0.00           C  
HETATM    4  C3  UNL     1       4.552   0.194  -0.282  1.00  0.00           C  
HETATM    5  C4  UNL     1       3.272   0.554  -0.711  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.127   0.132  -0.079  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.777   0.507  -0.524  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.535   1.311  -1.609  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.737   1.676  -2.044  1.00  0.00           C  
HETATM   10  O2  UNL     1      -0.904   2.409  -3.035  1.00  0.00           O  
HETATM   11  C9  UNL     1      -1.809   1.194  -1.335  1.00  0.00           C  
HETATM   12  C10 UNL     1      -3.117   1.483  -1.664  1.00  0.00           C  
HETATM   13  O3  UNL     1      -3.473   2.265  -2.713  1.00  0.00           O  
HETATM   14  C11 UNL     1      -4.183   0.961  -0.900  1.00  0.00           C  
HETATM   15  C12 UNL     1      -3.865   0.165   0.169  1.00  0.00           C  
HETATM   16  O4  UNL     1      -4.858  -0.396   0.983  1.00  0.00           O  
HETATM   17  C13 UNL     1      -6.220  -0.130   0.686  1.00  0.00           C  
HETATM   18  C14 UNL     1      -2.567  -0.118   0.492  1.00  0.00           C  
HETATM   19  O5  UNL     1      -2.254  -0.932   1.587  1.00  0.00           O  
HETATM   20  C15 UNL     1      -2.148  -2.309   1.344  1.00  0.00           C  
HETATM   21  C16 UNL     1      -1.504   0.383  -0.244  1.00  0.00           C  
HETATM   22  O6  UNL     1      -0.287   0.073   0.119  1.00  0.00           O  
HETATM   23  C17 UNL     1       2.247  -0.697   1.045  1.00  0.00           C  
HETATM   24  C18 UNL     1       3.513  -1.052   1.467  1.00  0.00           C  
HETATM   25  H1  UNL     1       7.225   0.417   0.570  1.00  0.00           H  
HETATM   26  H2  UNL     1       7.915  -0.926   1.507  1.00  0.00           H  
HETATM   27  H3  UNL     1       7.329  -1.192  -0.182  1.00  0.00           H  
HETATM   28  H4  UNL     1       5.441   0.538  -0.795  1.00  0.00           H  
HETATM   29  H5  UNL     1       3.212   1.189  -1.573  1.00  0.00           H  
HETATM   30  H6  UNL     1       1.379   1.704  -2.186  1.00  0.00           H  
HETATM   31  H7  UNL     1      -2.943   2.723  -3.364  1.00  0.00           H  
HETATM   32  H8  UNL     1      -5.202   1.179  -1.148  1.00  0.00           H  
HETATM   33  H9  UNL     1      -6.839  -0.686   1.446  1.00  0.00           H  
HETATM   34  H10 UNL     1      -6.515  -0.467  -0.314  1.00  0.00           H  
HETATM   35  H11 UNL     1      -6.401   0.945   0.875  1.00  0.00           H  
HETATM   36  H12 UNL     1      -1.878  -2.541   0.283  1.00  0.00           H  
HETATM   37  H13 UNL     1      -3.097  -2.800   1.600  1.00  0.00           H  
HETATM   38  H14 UNL     1      -1.354  -2.703   2.037  1.00  0.00           H  
HETATM   39  H15 UNL     1       1.353  -1.048   1.567  1.00  0.00           H  
HETATM   40  H16 UNL     1       3.630  -1.699   2.344  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3
CONECT    3    4    4   24
CONECT    4    5   28
CONECT    5    6    6   29
CONECT    6    7   23
CONECT    7    8    8   22
CONECT    8    9   30
CONECT    9   10   10   11
CONECT   11   12   12   21
CONECT   12   13   14
CONECT   13   31
CONECT   14   15   15   32
CONECT   15   16   18
CONECT   16   17
CONECT   17   33   34   35
CONECT   18   19   21   21
CONECT   19   20
CONECT   20   36   37   38
CONECT   21   22
CONECT   23   24   24   39
CONECT   24   40
END

HMDB0037458
     RDKit          3D
5-Hydroxy-4',7,8-trimethoxyflavone
 40 42  0  0  0  0  0  0  0  0999 V2000
    7.1180   -0.6734    0.7744 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8743   -1.0105    1.2949 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6557   -0.6201    0.8222 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5523    0.1935   -0.2820 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2715    0.5542   -0.7109 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1272    0.1317   -0.0790 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7769    0.5068   -0.5242 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5350    1.3113   -1.6093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7366    1.6758   -2.0439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9035    2.4089   -3.0354 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8090    1.1944   -1.3351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1172    1.4826   -1.6639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4732    2.2649   -2.7131 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1833    0.9607   -0.9001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8655    0.1650    0.1692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8576   -0.3965    0.9834 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2201   -0.1296    0.6863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5675   -0.1182    0.4918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2542   -0.9324    1.5866 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1484   -2.3092    1.3438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5044    0.3831   -0.2438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2865    0.0731    0.1192 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2473   -0.6972    1.0452 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5134   -1.0521    1.4672 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2247    0.4170    0.5699 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9150   -0.9260    1.5066 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3286   -1.1919   -0.1825 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4409    0.5382   -0.7953 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2120    1.1890   -1.5734 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3793    1.7037   -2.1857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9428    2.7231   -3.3639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2023    1.1789   -1.1477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8388   -0.6861    1.4460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5153   -0.4674   -0.3139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4005    0.9453    0.8751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8776   -2.5410    0.2831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0974   -2.7996    1.6003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3537   -2.7026    2.0372 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3529   -1.0477    1.5670 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6305   -1.6995    2.3439 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
 16 17  1  0
 15 18  1  0
 18 19  1  0
 19 20  1  0
 18 21  2  0
 21 22  1  0
  6 23  1  0
 23 24  2  0
 24  3  1  0
 22  7  1  0
 21 11  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  5 29  1  0
  8 30  1  0
 13 31  1  0
 14 32  1  0
 17 33  1  0
 17 34  1  0
 17 35  1  0
 20 36  1  0
 20 37  1  0
 20 38  1  0
 23 39  1  0
 24 40  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
5-Hydroxy-7,8,4'-trimethoxyflavone	HMDB
5-Hydroxy-7,8-dimethoxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one	HMDB
Isoscutellarein 7,8,4'-trimethyl ether	HMDB

Chemical Formula

C₁₈H₁₆O₆

Average Molecular Weight

328.316

Monoisotopic Molecular Weight

328.094688244

IUPAC Name

5-hydroxy-7,8-dimethoxy-2-(4-methoxyphenyl)-4H-chromen-4-one

Traditional Name

5-hydroxy-7,8-dimethoxy-2-(4-methoxyphenyl)chromen-4-one

CAS Registry Number

57096-03-4

SMILES

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

InChI Identifier

InChI=1S/C18H16O6/c1-21-11-6-4-10(5-7-11)14-8-12(19)16-13(20)9-15(22-2)17(23-3)18(16)24-14/h4-9,20H,1-3H3

InChI Key

RRZRJBICWWNHRB-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 8-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C8 atom of the flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

O-methylated flavonoids

Direct Parent

8-O-methylated flavonoids

Alternative Parents

Substituents

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Flavones and Flavonols (LMPK12111367 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0037458)

Cellular substructure

Membrane (HMDB: HMDB0037458)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0037458)

Source

Exogenous

Food

Food (HMDB: HMDB0037458)

Fruit

Citrus

Mandarin orange (Clementine, Tangerine) (FooDB: FOOD00056)
Citrus (FooDB: FOOD00859)

Endogenous

Plant

Plant (HMDB: HMDB0037458)

Not Available

Nutrient (HMDB: HMDB0037458)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	220 - 221 °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	0.023 g/L	ALOGPS
logP	3.31	ALOGPS
logP	2.84	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	9.08	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	74.22 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	88.34 m³·mol⁻¹	ChemAxon
Polarizability	33.75 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]+	177.106	31661259
DarkChem	[M-H]-	179.818	31661259
DeepCCS	[M+H]+	175.954	30932474
DeepCCS	[M-H]-	173.596	30932474
DeepCCS	[M-2H]-	207.611	30932474
DeepCCS	[M+Na]+	182.838	30932474
AllCCS	[M+H]+	176.4	32859911
AllCCS	[M+H-H2O]+	172.9	32859911
AllCCS	[M+NH4]+	179.6	32859911
AllCCS	[M+Na]+	180.5	32859911
AllCCS	[M-H]-	178.7	32859911
AllCCS	[M+Na-2H]-	178.1	32859911
AllCCS	[M+HCOO]-	177.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5-Hydroxy-4',7,8-trimethoxyflavone	COC1=CC=C(C=C1)C1=CC(=O)C2=C(O1)C(OC)=C(OC)C=C2O	4564.4	Standard polar	33892256
5-Hydroxy-4',7,8-trimethoxyflavone	COC1=CC=C(C=C1)C1=CC(=O)C2=C(O1)C(OC)=C(OC)C=C2O	3095.2	Standard non polar	33892256
5-Hydroxy-4',7,8-trimethoxyflavone	COC1=CC=C(C=C1)C1=CC(=O)C2=C(O1)C(OC)=C(OC)C=C2O	3127.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
5-Hydroxy-4',7,8-trimethoxyflavone,1TMS,isomer #1	COC1=CC=C(C2=CC(=O)C3=C(O[Si](C)(C)C)C=C(OC)C(OC)=C3O2)C=C1	3214.0	Semi standard non polar	33892256
5-Hydroxy-4',7,8-trimethoxyflavone,1TBDMS,isomer #1	COC1=CC=C(C2=CC(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(OC)C(OC)=C3O2)C=C1	3414.7	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-Hydroxy-4',7,8-trimethoxyflavone GC-MS (Non-derivatized) - 70eV, Positive	splash10-01r2-0698000000-ef340fd4205882b7e5e1	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Hydroxy-4',7,8-trimethoxyflavone GC-MS (1 TMS) - 70eV, Positive	splash10-00dr-1219000000-f9395b1dba7f19d17e93	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Hydroxy-4',7,8-trimethoxyflavone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Hydroxy-4',7,8-trimethoxyflavone 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-Hydroxy-4',7,8-trimethoxyflavone 10V, Positive-QTOF	splash10-004i-0009000000-d103da5b57e2db6e2750	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxy-4',7,8-trimethoxyflavone 20V, Positive-QTOF	splash10-004i-0019000000-f0e547f4471daf47eae0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxy-4',7,8-trimethoxyflavone 40V, Positive-QTOF	splash10-00ed-0390000000-799dbdcda5c01402b9c2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxy-4',7,8-trimethoxyflavone 10V, Negative-QTOF	splash10-004i-0009000000-d4f0725d5fc8c0fe2caf	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxy-4',7,8-trimethoxyflavone 20V, Negative-QTOF	splash10-004i-0029000000-c3afb0f8204a7ba59fb2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxy-4',7,8-trimethoxyflavone 40V, Negative-QTOF	splash10-001i-0291000000-406210cc7f96d7f34a25	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxy-4',7,8-trimethoxyflavone 10V, Positive-QTOF	splash10-004i-0009000000-469c8ff76acf89a49db2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxy-4',7,8-trimethoxyflavone 20V, Positive-QTOF	splash10-004i-0009000000-b1d1da4246ee5f0dbb74	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxy-4',7,8-trimethoxyflavone 40V, Positive-QTOF	splash10-06ri-0293000000-981487bae9509af70bdf	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxy-4',7,8-trimethoxyflavone 10V, Negative-QTOF	splash10-004i-0009000000-955868728229e2829941	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxy-4',7,8-trimethoxyflavone 20V, Negative-QTOF	splash10-01u0-0049000000-88d12f5f34bfc8bf9fbc	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB016520

KNApSAcK ID

C00003854

Chemspider ID

10405466

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14353376

PDB ID

Not Available

ChEBI ID

Not Available

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 5-Hydroxy-4',7,8-trimethoxyflavone (HMDB0037458)

MOL for HMDB0037458 (5-Hydroxy-4',7,8-trimethoxyflavone)

3D MOL for HMDB0037458 (5-Hydroxy-4',7,8-trimethoxyflavone)

3D SDF for HMDB0037458 (5-Hydroxy-4',7,8-trimethoxyflavone)

3D-SDF for HMDB0037458 (5-Hydroxy-4',7,8-trimethoxyflavone)

PDB for HMDB0037458 (5-Hydroxy-4',7,8-trimethoxyflavone)

3D PDB for HMDB0037458 (5-Hydroxy-4',7,8-trimethoxyflavone)

SMILES for HMDB0037458 (5-Hydroxy-4',7,8-trimethoxyflavone)

INCHI for HMDB0037458 (5-Hydroxy-4',7,8-trimethoxyflavone)

Structure for HMDB0037458 (5-Hydroxy-4',7,8-trimethoxyflavone)

3D Structure for HMDB0037458 (5-Hydroxy-4',7,8-trimethoxyflavone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra