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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 01:50:09 UTC

Update Date

2022-03-07 02:56:33 UTC

HMDB ID

HMDB0040303

Secondary Accession Numbers

HMDB40303

Metabolite Identification

Common Name

5-Hydroxy-4,4',6-trimethoxyaurone

Description

5-Hydroxy-4,4',6-trimethoxyaurone belongs to the class of organic compounds known as aurone flavonoids. These are flavonoids containing a 2-Benzylidene-1-benzofuran-3-one based core. Aurone flavonoids provide the bright yellow color of some important ornamental flowers, such as snapdragon (Antirrhinum majus). 5-Hydroxy-4,4',6-trimethoxyaurone has been detected, but not quantified in, fats and oils and sunflowers (Helianthus annuus). This could make 5-hydroxy-4,4',6-trimethoxyaurone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 5-Hydroxy-4,4',6-trimethoxyaurone.

Structure

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

HMDB0040303
     RDKit          3D
5-Hydroxy-4,4',6-trimethoxyaurone
 40 42  0  0  0  0  0  0  0  0999 V2000
    6.9900   -0.5019    0.8815 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0247   -1.1174    0.0504 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8437   -0.3950   -0.1924 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8720   -0.9724   -1.0069 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6990   -0.2767   -1.2593 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4432    0.9677   -0.7397 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2559    1.7469   -0.9153 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0654    1.3091   -0.6179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1569    1.9792   -0.7549 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1917    1.1689   -0.3210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5775    1.3612   -0.2503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4253    0.3913    0.2271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8147    0.6231    0.2823 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3036    1.8790   -0.1679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9097   -0.8118    0.6527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7858   -1.7710    1.1289 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5517   -1.0349    0.5974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9834   -2.2277    1.0134 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8151   -3.2772    0.1023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7116   -0.0446    0.1125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2600    0.0123   -0.0644 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5080   -0.9339    0.2356 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4441    1.5126    0.0724 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6219    0.8537    0.3460 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5872   -0.3189    1.8893 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9479   -1.0612    0.8794 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2473    0.5080    0.4506 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0552   -1.9558   -1.4264 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9776   -0.7459   -1.9185 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3312    2.7708   -1.3209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9653    2.3222   -0.5931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3926    1.9415   -0.1408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9877    1.9918   -1.2370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7899    2.6823    0.4090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7710   -1.6629    1.1907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6361   -2.8467   -0.9102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6792   -3.9502    0.0044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9194   -3.8891    0.3462 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3159    2.5038    0.5250 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3983    1.2698    0.9726 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  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 12 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 17 20  2  0
 20 21  1  0
 21 22  2  0
  6 23  1  0
 23 24  2  0
 24  3  1  0
 21  8  1  0
 20 10  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  5 29  1  0
  7 30  1  0
 11 31  1  0
 14 32  1  0
 14 33  1  0
 14 34  1  0
 16 35  1  0
 19 36  1  0
 19 37  1  0
 19 38  1  0
 23 39  1  0
 24 40  1  0
M  END


  Mrv0541 05061311442D          

 24 26  0  0  0  0            999 V2000
   -1.4087   -4.2703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    0.9521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4087   -1.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712   -2.1269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8212   -2.1269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5837   -2.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5837   -1.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4087   -2.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838   -2.1500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -1.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8212   -3.5558    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  4  1  0  0  0  0
  7  5  2  0  0  0  0
 10  4  2  0  0  0  0
 10  5  1  0  0  0  0
 10  8  1  0  0  0  0
 11  6  2  0  0  0  0
 11  7  1  0  0  0  0
 12  9  2  0  0  0  0
 13  9  1  0  0  0  0
 14  8  2  0  0  0  0
 15 12  1  0  0  0  0
 16 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17 13  2  0  0  0  0
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 20 17  1  0  0  0  0
 21  1  1  0  0  0  0
 21 11  1  0  0  0  0
 22  2  1  0  0  0  0
 22 13  1  0  0  0  0
 23  3  1  0  0  0  0
 23 18  1  0  0  0  0
 24 12  1  0  0  0  0
 24 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0040303

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC=C(\C=C2\OC3=CC(OC)=C(O)C(OC)=C3C2=O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C18H16O6/c1-21-11-6-4-10(5-7-11)8-14-16(19)15-12(24-14)9-13(22-2)17(20)18(15)23-3/h4-9,20H,1-3H3/b14-8+

> <INCHI_KEY>
SDBGODOJRLLNSU-RIYZIHGNSA-N

> <FORMULA>
C18H16O6

> <MOLECULAR_WEIGHT>
328.316

> <EXACT_MASS>
328.094688244

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
34.06686967579992

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-5-hydroxy-4,6-dimethoxy-2-[(4-methoxyphenyl)methylidene]-2,3-dihydro-1-benzofuran-3-one

> <ALOGPS_LOGP>
3.36

> <JCHEM_LOGP>
2.4256951976666663

> <ALOGPS_LOGS>
-4.26

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.005249491935999

> <JCHEM_PKA_STRONGEST_BASIC>
-4.389222842522423

> <JCHEM_POLAR_SURFACE_AREA>
74.22000000000001

> <JCHEM_REFRACTIVITY>
88.4168

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.79e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-5-hydroxy-4,6-dimethoxy-2-[(4-methoxyphenyl)methylidene]-1-benzofuran-3-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0040303
     RDKit          3D
5-Hydroxy-4,4',6-trimethoxyaurone
 40 42  0  0  0  0  0  0  0  0999 V2000
    6.9900   -0.5019    0.8815 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0247   -1.1174    0.0504 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8437   -0.3950   -0.1924 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8720   -0.9724   -1.0069 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6990   -0.2767   -1.2593 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4432    0.9677   -0.7397 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2559    1.7469   -0.9153 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0654    1.3091   -0.6179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1569    1.9792   -0.7549 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1917    1.1689   -0.3210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5775    1.3612   -0.2503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4253    0.3913    0.2271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8147    0.6231    0.2823 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3036    1.8790   -0.1679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9097   -0.8118    0.6527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7858   -1.7710    1.1289 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5517   -1.0349    0.5974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9834   -2.2277    1.0134 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8151   -3.2772    0.1023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7116   -0.0446    0.1125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2600    0.0123   -0.0644 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5080   -0.9339    0.2356 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4441    1.5126    0.0724 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6219    0.8537    0.3460 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5872   -0.3189    1.8893 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9479   -1.0612    0.8794 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2473    0.5080    0.4506 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0552   -1.9558   -1.4264 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9776   -0.7459   -1.9185 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3312    2.7708   -1.3209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9653    2.3222   -0.5931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3926    1.9415   -0.1408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9877    1.9918   -1.2370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7899    2.6823    0.4090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7710   -1.6629    1.1907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6361   -2.8467   -0.9102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6792   -3.9502    0.0044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9194   -3.8891    0.3462 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3159    2.5038    0.5250 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3983    1.2698    0.9726 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  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 12 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 17 20  2  0
 20 21  1  0
 21 22  2  0
  6 23  1  0
 23 24  2  0
 24  3  1  0
 21  8  1  0
 20 10  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  5 29  1  0
  7 30  1  0
 11 31  1  0
 14 32  1  0
 14 33  1  0
 14 34  1  0
 16 35  1  0
 19 36  1  0
 19 37  1  0
 19 38  1  0
 23 39  1  0
 24 40  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -2.630  -7.971   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.591   1.777   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.258  -5.153   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.630  -2.636   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.320  -3.970   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.400  -3.970   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.090  -5.304   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.320  -1.303   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.090  -2.636   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.630  -5.304   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       1.650  -4.013   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       7.591  -2.843   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -3.400  -6.637   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       7.591   0.237   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       4.924  -4.383   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       2.126  -0.057   0.000  0.00  0.00           O+0
CONECT    1   21                                                            
CONECT    2   22                                                            
CONECT    3   23                                                            
CONECT    4    6   10                                                       
CONECT    5    7   10                                                       
CONECT    6    4   11                                                       
CONECT    7    5   11                                                       
CONECT    8   10   14                                                       
CONECT    9   12   13                                                       
CONECT   10    4    5    8                                                  
CONECT   11    6    7   21                                                  
CONECT   12    9   15   24                                                  
CONECT   13    9   17   22                                                  
CONECT   14    8   16   24                                                  
CONECT   15   12   16   18                                                  
CONECT   16   14   15   19                                                  
CONECT   17   13   18   20                                                  
CONECT   18   15   17   23                                                  
CONECT   19   16                                                            
CONECT   20   17                                                            
CONECT   21    1   11                                                       
CONECT   22    2   13                                                       
CONECT   23    3   18                                                       
CONECT   24   12   14                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

COMPND    HMDB0040303
HETATM    1  C1  UNL     1       6.990  -0.502   0.882  1.00  0.00           C  
HETATM    2  O1  UNL     1       6.025  -1.117   0.050  1.00  0.00           O  
HETATM    3  C2  UNL     1       4.844  -0.395  -0.192  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.872  -0.972  -1.007  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.699  -0.277  -1.259  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.443   0.968  -0.740  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.256   1.747  -0.915  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.065   1.309  -0.618  1.00  0.00           C  
HETATM    9  O2  UNL     1      -1.157   1.979  -0.755  1.00  0.00           O  
HETATM   10  C8  UNL     1      -2.192   1.169  -0.321  1.00  0.00           C  
HETATM   11  C9  UNL     1      -3.578   1.361  -0.250  1.00  0.00           C  
HETATM   12  C10 UNL     1      -4.425   0.391   0.227  1.00  0.00           C  
HETATM   13  O3  UNL     1      -5.815   0.623   0.282  1.00  0.00           O  
HETATM   14  C11 UNL     1      -6.304   1.879  -0.168  1.00  0.00           C  
HETATM   15  C12 UNL     1      -3.910  -0.812   0.653  1.00  0.00           C  
HETATM   16  O4  UNL     1      -4.786  -1.771   1.129  1.00  0.00           O  
HETATM   17  C13 UNL     1      -2.552  -1.035   0.597  1.00  0.00           C  
HETATM   18  O5  UNL     1      -1.983  -2.228   1.013  1.00  0.00           O  
HETATM   19  C14 UNL     1      -1.815  -3.277   0.102  1.00  0.00           C  
HETATM   20  C15 UNL     1      -1.712  -0.045   0.112  1.00  0.00           C  
HETATM   21  C16 UNL     1      -0.260   0.012  -0.064  1.00  0.00           C  
HETATM   22  O6  UNL     1       0.508  -0.934   0.236  1.00  0.00           O  
HETATM   23  C17 UNL     1       3.444   1.513   0.072  1.00  0.00           C  
HETATM   24  C18 UNL     1       4.622   0.854   0.346  1.00  0.00           C  
HETATM   25  H1  UNL     1       6.587  -0.319   1.889  1.00  0.00           H  
HETATM   26  H2  UNL     1       7.948  -1.061   0.879  1.00  0.00           H  
HETATM   27  H3  UNL     1       7.247   0.508   0.451  1.00  0.00           H  
HETATM   28  H4  UNL     1       4.055  -1.956  -1.426  1.00  0.00           H  
HETATM   29  H5  UNL     1       1.978  -0.746  -1.919  1.00  0.00           H  
HETATM   30  H6  UNL     1       1.331   2.771  -1.321  1.00  0.00           H  
HETATM   31  H7  UNL     1      -3.965   2.322  -0.593  1.00  0.00           H  
HETATM   32  H8  UNL     1      -7.393   1.942  -0.141  1.00  0.00           H  
HETATM   33  H9  UNL     1      -5.988   1.992  -1.237  1.00  0.00           H  
HETATM   34  H10 UNL     1      -5.790   2.682   0.409  1.00  0.00           H  
HETATM   35  H11 UNL     1      -5.771  -1.663   1.191  1.00  0.00           H  
HETATM   36  H12 UNL     1      -1.636  -2.847  -0.910  1.00  0.00           H  
HETATM   37  H13 UNL     1      -2.679  -3.950   0.004  1.00  0.00           H  
HETATM   38  H14 UNL     1      -0.919  -3.889   0.346  1.00  0.00           H  
HETATM   39  H15 UNL     1       3.316   2.504   0.525  1.00  0.00           H  
HETATM   40  H16 UNL     1       5.398   1.270   0.973  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   30
CONECT    8    9   21
CONECT    9   10
CONECT   10   11   11   20
CONECT   11   12   31
CONECT   12   13   15   15
CONECT   13   14
CONECT   14   32   33   34
CONECT   15   16   17
CONECT   16   35
CONECT   17   18   20   20
CONECT   18   19
CONECT   19   36   37   38
CONECT   20   21
CONECT   21   22   22
CONECT   23   24   24   39
CONECT   24   40
END

HMDB0040303
     RDKit          3D
5-Hydroxy-4,4',6-trimethoxyaurone
 40 42  0  0  0  0  0  0  0  0999 V2000
    6.9900   -0.5019    0.8815 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0247   -1.1174    0.0504 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8437   -0.3950   -0.1924 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8720   -0.9724   -1.0069 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6990   -0.2767   -1.2593 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4432    0.9677   -0.7397 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2559    1.7469   -0.9153 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0654    1.3091   -0.6179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1569    1.9792   -0.7549 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1917    1.1689   -0.3210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5775    1.3612   -0.2503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4253    0.3913    0.2271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8147    0.6231    0.2823 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3036    1.8790   -0.1679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9097   -0.8118    0.6527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7858   -1.7710    1.1289 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5517   -1.0349    0.5974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9834   -2.2277    1.0134 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8151   -3.2772    0.1023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7116   -0.0446    0.1125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2600    0.0123   -0.0644 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5080   -0.9339    0.2356 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4441    1.5126    0.0724 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6219    0.8537    0.3460 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5872   -0.3189    1.8893 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9479   -1.0612    0.8794 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2473    0.5080    0.4506 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0552   -1.9558   -1.4264 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9776   -0.7459   -1.9185 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3312    2.7708   -1.3209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9653    2.3222   -0.5931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3926    1.9415   -0.1408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9877    1.9918   -1.2370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7899    2.6823    0.4090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7710   -1.6629    1.1907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6361   -2.8467   -0.9102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6792   -3.9502    0.0044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9194   -3.8891    0.3462 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3159    2.5038    0.5250 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3983    1.2698    0.9726 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  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 12 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 17 20  2  0
 20 21  1  0
 21 22  2  0
  6 23  1  0
 23 24  2  0
 24  3  1  0
 21  8  1  0
 20 10  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  5 29  1  0
  7 30  1  0
 11 31  1  0
 14 32  1  0
 14 33  1  0
 14 34  1  0
 16 35  1  0
 19 36  1  0
 19 37  1  0
 19 38  1  0
 23 39  1  0
 24 40  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
5-Hydroxy-4,6,4'-trimethoxyaurone	HMDB

Chemical Formula

C₁₈H₁₆O₆

Average Molecular Weight

328.316

Monoisotopic Molecular Weight

328.094688244

IUPAC Name

(2E)-5-hydroxy-4,6-dimethoxy-2-[(4-methoxyphenyl)methylidene]-2,3-dihydro-1-benzofuran-3-one

Traditional Name

(2E)-5-hydroxy-4,6-dimethoxy-2-[(4-methoxyphenyl)methylidene]-1-benzofuran-3-one

CAS Registry Number

137648-02-3

SMILES

COC1=CC=C(\C=C2\OC3=CC(OC)=C(O)C(OC)=C3C2=O)C=C1

InChI Identifier

InChI=1S/C18H16O6/c1-21-11-6-4-10(5-7-11)8-14-16(19)15-12(24-14)9-13(22-2)17(20)18(15)23-3/h4-9,20H,1-3H3/b14-8+

InChI Key

SDBGODOJRLLNSU-RIYZIHGNSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aurone flavonoids. These are flavonoids containing a 2-Benzylidene-1-benzofuran-3-one based core. Aurone flavonoids provide the bright yellow color of some important ornamental flowers, such as snapdragon (Antirrhinum majus).

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Aurone flavonoids

Sub Class

Not Available

Direct Parent

Aurone flavonoids

Alternative Parents

Substituents

Aurone
Coumaran
Benzofuran
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Aryl ketone
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Ketone
Ether
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0040303)

Cellular substructure

Membrane (HMDB: HMDB0040303)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0040303)

Source

Exogenous

Food

Food (HMDB: HMDB0040303)

Herb and spice

Oilseed crop

Sunflower (FooDB: FOOD00086)

Fat and oil

Fats and oils (FooDB: FOOD00864)

Endogenous

Plant

Plant (HMDB: HMDB0040303)

Not Available

Nutrient (HMDB: HMDB0040303)

Physical Properties

State

Not Available

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.018 g/L	ALOGPS
logP	3.36	ALOGPS
logP	2.43	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	9.01	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	88.42 m³·mol⁻¹	ChemAxon
Polarizability	34.07 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]+	183.597	30932474
DeepCCS	[M-H]-	181.172	30932474
DeepCCS	[M-2H]-	215.618	30932474
DeepCCS	[M+Na]+	191.452	30932474
AllCCS	[M+H]+	177.7	32859911
AllCCS	[M+H-H2O]+	174.2	32859911
AllCCS	[M+NH4]+	180.9	32859911
AllCCS	[M+Na]+	181.8	32859911
AllCCS	[M-H]-	179.3	32859911
AllCCS	[M+Na-2H]-	178.9	32859911
AllCCS	[M+HCOO]-	178.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5-Hydroxy-4,4',6-trimethoxyaurone	COC1=CC=C(\C=C2\OC3=CC(OC)=C(O)C(OC)=C3C2=O)C=C1	4690.6	Standard polar	33892256
5-Hydroxy-4,4',6-trimethoxyaurone	COC1=CC=C(\C=C2\OC3=CC(OC)=C(O)C(OC)=C3C2=O)C=C1	2907.5	Standard non polar	33892256
5-Hydroxy-4,4',6-trimethoxyaurone	COC1=CC=C(\C=C2\OC3=CC(OC)=C(O)C(OC)=C3C2=O)C=C1	3087.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
5-Hydroxy-4,4',6-trimethoxyaurone,1TMS,isomer #1	COC1=CC=C(/C=C2/OC3=CC(OC)=C(O[Si](C)(C)C)C(OC)=C3C2=O)C=C1	3037.5	Semi standard non polar	33892256
5-Hydroxy-4,4',6-trimethoxyaurone,1TBDMS,isomer #1	COC1=CC=C(/C=C2/OC3=CC(OC)=C(O[Si](C)(C)C(C)(C)C)C(OC)=C3C2=O)C=C1	3271.4	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-4,4',6-trimethoxyaurone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0w2a-0956000000-e6093164eedf421be871	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Hydroxy-4,4',6-trimethoxyaurone GC-MS (1 TMS) - 70eV, Positive	splash10-00dr-2159000000-5ca50444f2a9dae8bacc	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Hydroxy-4,4',6-trimethoxyaurone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Hydroxy-4,4',6-trimethoxyaurone 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-4,4',6-trimethoxyaurone 10V, Positive-QTOF	splash10-004i-0309000000-ad731a39f29cb36b0edd	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxy-4,4',6-trimethoxyaurone 20V, Positive-QTOF	splash10-0002-0923000000-770535787e6424ea4c74	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxy-4,4',6-trimethoxyaurone 40V, Positive-QTOF	splash10-067i-1900000000-5da52b9df4e9fba79cd1	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxy-4,4',6-trimethoxyaurone 10V, Negative-QTOF	splash10-004i-0009000000-0a81a922e8055b99fdec	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxy-4,4',6-trimethoxyaurone 20V, Negative-QTOF	splash10-004i-0029000000-a3c4dc74eb16f7cd5753	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxy-4,4',6-trimethoxyaurone 40V, Negative-QTOF	splash10-001l-1190000000-f80f2c0f463ddc1b314b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxy-4,4',6-trimethoxyaurone 10V, Negative-QTOF	splash10-004i-0009000000-0447e52768356e443881	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxy-4,4',6-trimethoxyaurone 20V, Negative-QTOF	splash10-004i-0097000000-0d3ef54c3c5cdfd9f82c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxy-4,4',6-trimethoxyaurone 40V, Negative-QTOF	splash10-0pc3-1090000000-608275a8fadb0245609b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxy-4,4',6-trimethoxyaurone 10V, Positive-QTOF	splash10-004i-0009000000-469c8ff76acf89a49db2	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxy-4,4',6-trimethoxyaurone 20V, Positive-QTOF	splash10-004i-0019000000-63aff870387abffc849f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxy-4,4',6-trimethoxyaurone 40V, Positive-QTOF	splash10-0aba-0190000000-88bed1f780ada18d78ef	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

Not Available

FooDB ID

FDB020026

KNApSAcK ID

C00014651

Chemspider ID

30777483

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131752787

PDB ID

Not Available

ChEBI ID

174403

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-4,4',6-trimethoxyaurone (HMDB0040303)

MOL for HMDB0040303 (5-Hydroxy-4,4',6-trimethoxyaurone)

3D MOL for HMDB0040303 (5-Hydroxy-4,4',6-trimethoxyaurone)

3D SDF for HMDB0040303 (5-Hydroxy-4,4',6-trimethoxyaurone)

3D-SDF for HMDB0040303 (5-Hydroxy-4,4',6-trimethoxyaurone)

PDB for HMDB0040303 (5-Hydroxy-4,4',6-trimethoxyaurone)

3D PDB for HMDB0040303 (5-Hydroxy-4,4',6-trimethoxyaurone)

SMILES for HMDB0040303 (5-Hydroxy-4,4',6-trimethoxyaurone)

INCHI for HMDB0040303 (5-Hydroxy-4,4',6-trimethoxyaurone)

Structure for HMDB0040303 (5-Hydroxy-4,4',6-trimethoxyaurone)

3D Structure for HMDB0040303 (5-Hydroxy-4,4',6-trimethoxyaurone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra