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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:43:01 UTC

Update Date

2022-03-07 02:52:58 UTC

HMDB ID

HMDB0031420

Secondary Accession Numbers

HMDB31420

Metabolite Identification

Common Name

Heliannone C

Description

Heliannone C 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. Based on a literature review very few articles have been published on Heliannone C.

Structure

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

HMDB0031420
     RDKit          3D
Heliannone C
 35 37  0  0  0  0  0  0  0  0999 V2000
   -1.8283    2.6217    0.6727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5225    1.4513    1.0621 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4056    0.3279    0.2856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3358    0.1704   -0.7416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3296    1.1065   -0.9643 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2754   -0.9347   -1.5584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2778   -1.8885   -1.3459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3595   -1.7437   -0.3402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4220   -0.6316    0.4801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4992   -0.4759    1.4988 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7632   -1.1122    1.5104 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6930   -0.3007    0.7377 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5793   -0.7866   -0.1942 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4388    0.0684   -0.8920 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4163    1.4201   -0.6603 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2848    2.2596   -1.3692 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5410    1.9197    0.2631 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6975    1.0661    0.9456 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6128   -2.5279    1.0641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3013   -2.7033   -0.0727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1576   -3.7003   -0.8180 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3750    3.1287   -0.1438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8227    2.3399    0.2879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7413    3.3287    1.5480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4384    1.9350   -0.4133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9704   -1.0950   -2.3598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2066   -2.7597   -1.9668 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1006   -1.1226    2.5688 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5985   -1.8331   -0.3755 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1269   -0.3203   -1.6174 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1950    2.4165   -0.9251 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5148    2.9991    0.4561 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0245    1.5123    1.6652 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5445   -3.0538    0.8651 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1374   -3.0818    1.9302 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
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 11 19  1  0
 19 20  1  0
 20 21  2  0
  9  3  1  0
 18 12  1  0
 20  8  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  5 25  1  0
  6 26  1  0
  7 27  1  0
 11 28  1  0
 13 29  1  0
 14 30  1  0
 16 31  1  0
 17 32  1  0
 18 33  1  0
 19 34  1  0
 19 35  1  0
M  END


  Mrv0541 05061305562D          

 21 23  0  0  0  0            999 V2000
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  2  1  0  0  0  0
  5  3  2  0  0  0  0
  7  6  2  0  0  0  0
  9  2  2  0  0  0  0
  9  3  1  0  0  0  0
 10  4  2  0  0  0  0
 10  5  1  0  0  0  0
 11  6  1  0  0  0  0
 12  7  1  0  0  0  0
 13  8  1  0  0  0  0
 13 11  1  0  0  0  0
 14  8  1  0  0  0  0
 14  9  1  0  0  0  0
 15 11  2  0  0  0  0
 16 12  2  0  0  0  0
 16 15  1  0  0  0  0
 17 10  1  0  0  0  0
 18 12  1  0  0  0  0
 19 13  2  0  0  0  0
 20  1  1  0  0  0  0
 20 16  1  0  0  0  0
 21 14  1  0  0  0  0
 21 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0031420

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(O)C=CC2=C1OC(CC2=O)C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H14O5/c1-20-16-12(18)7-6-11-13(19)8-14(21-15(11)16)9-2-4-10(17)5-3-9/h2-7,14,17-18H,8H2,1H3

> <INCHI_KEY>
BMGKZGNJRBKRFC-UHFFFAOYSA-N

> <FORMULA>
C16H14O5

> <MOLECULAR_WEIGHT>
286.2794

> <EXACT_MASS>
286.084123558

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
29.16286810326708

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-hydroxy-2-(4-hydroxyphenyl)-8-methoxy-3,4-dihydro-2H-1-benzopyran-4-one

> <ALOGPS_LOGP>
2.83

> <JCHEM_LOGP>
2.3310021063333335

> <ALOGPS_LOGS>
-3.50

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.504029266029583

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.32786558144115

> <JCHEM_PKA_STRONGEST_BASIC>
-4.685392193045796

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
75.77210000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.12e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7-hydroxy-2-(4-hydroxyphenyl)-8-methoxy-2,3-dihydro-1-benzopyran-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0031420
     RDKit          3D
Heliannone C
 35 37  0  0  0  0  0  0  0  0999 V2000
   -1.8283    2.6217    0.6727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5225    1.4513    1.0621 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4056    0.3279    0.2856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3358    0.1704   -0.7416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3296    1.1065   -0.9643 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2754   -0.9347   -1.5584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2778   -1.8885   -1.3459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3595   -1.7437   -0.3402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4220   -0.6316    0.4801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4992   -0.4759    1.4988 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7632   -1.1122    1.5104 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6930   -0.3007    0.7377 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5793   -0.7866   -0.1942 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4388    0.0684   -0.8920 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4163    1.4201   -0.6603 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2848    2.2596   -1.3692 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5410    1.9197    0.2631 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6975    1.0661    0.9456 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6128   -2.5279    1.0641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3013   -2.7033   -0.0727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1576   -3.7003   -0.8180 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3750    3.1287   -0.1438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8227    2.3399    0.2879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7413    3.3287    1.5480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4384    1.9350   -0.4133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9704   -1.0950   -2.3598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2066   -2.7597   -1.9668 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1006   -1.1226    2.5688 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5985   -1.8331   -0.3755 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1269   -0.3203   -1.6174 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1950    2.4165   -0.9251 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5148    2.9991    0.4561 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0245    1.5123    1.6652 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5445   -3.0538    0.8651 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1374   -3.0818    1.9302 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
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 11 19  1  0
 19 20  1  0
 20 21  2  0
  9  3  1  0
 18 12  1  0
 20  8  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  5 25  1  0
  6 26  1  0
  7 27  1  0
 11 28  1  0
 13 29  1  0
 14 30  1  0
 16 31  1  0
 17 32  1  0
 18 33  1  0
 19 34  1  0
 19 35  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       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      13.337  -3.080   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
CONECT    1   20                                                            
CONECT    2    4    9                                                       
CONECT    3    5    9                                                       
CONECT    4    2   10                                                       
CONECT    5    3   10                                                       
CONECT    6    7   11                                                       
CONECT    7    6   12                                                       
CONECT    8   13   14                                                       
CONECT    9    2    3   14                                                  
CONECT   10    4    5   17                                                  
CONECT   11    6   13   15                                                  
CONECT   12    7   16   18                                                  
CONECT   13    8   11   19                                                  
CONECT   14    8    9   21                                                  
CONECT   15   11   16   21                                                  
CONECT   16   12   15   20                                                  
CONECT   17   10                                                            
CONECT   18   12                                                            
CONECT   19   13                                                            
CONECT   20    1   16                                                       
CONECT   21   14   15                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    HMDB0031420
HETATM    1  C1  UNL     1      -1.828   2.622   0.673  1.00  0.00           C  
HETATM    2  O1  UNL     1      -2.522   1.451   1.062  1.00  0.00           O  
HETATM    3  C2  UNL     1      -2.406   0.328   0.286  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.336   0.170  -0.742  1.00  0.00           C  
HETATM    5  O2  UNL     1      -4.330   1.107  -0.964  1.00  0.00           O  
HETATM    6  C4  UNL     1      -3.275  -0.935  -1.558  1.00  0.00           C  
HETATM    7  C5  UNL     1      -2.278  -1.889  -1.346  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.360  -1.744  -0.340  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.422  -0.632   0.480  1.00  0.00           C  
HETATM   10  O3  UNL     1      -0.499  -0.476   1.499  1.00  0.00           O  
HETATM   11  C8  UNL     1       0.763  -1.112   1.510  1.00  0.00           C  
HETATM   12  C9  UNL     1       1.693  -0.301   0.738  1.00  0.00           C  
HETATM   13  C10 UNL     1       2.579  -0.787  -0.194  1.00  0.00           C  
HETATM   14  C11 UNL     1       3.439   0.068  -0.892  1.00  0.00           C  
HETATM   15  C12 UNL     1       3.416   1.420  -0.660  1.00  0.00           C  
HETATM   16  O4  UNL     1       4.285   2.260  -1.369  1.00  0.00           O  
HETATM   17  C13 UNL     1       2.541   1.920   0.263  1.00  0.00           C  
HETATM   18  C14 UNL     1       1.697   1.066   0.946  1.00  0.00           C  
HETATM   19  C15 UNL     1       0.613  -2.528   1.064  1.00  0.00           C  
HETATM   20  C16 UNL     1      -0.301  -2.703  -0.073  1.00  0.00           C  
HETATM   21  O5  UNL     1      -0.158  -3.700  -0.818  1.00  0.00           O  
HETATM   22  H1  UNL     1      -2.375   3.129  -0.144  1.00  0.00           H  
HETATM   23  H2  UNL     1      -0.823   2.340   0.288  1.00  0.00           H  
HETATM   24  H3  UNL     1      -1.741   3.329   1.548  1.00  0.00           H  
HETATM   25  H4  UNL     1      -4.438   1.935  -0.413  1.00  0.00           H  
HETATM   26  H5  UNL     1      -3.970  -1.095  -2.360  1.00  0.00           H  
HETATM   27  H6  UNL     1      -2.207  -2.760  -1.967  1.00  0.00           H  
HETATM   28  H7  UNL     1       1.101  -1.123   2.569  1.00  0.00           H  
HETATM   29  H8  UNL     1       2.598  -1.833  -0.376  1.00  0.00           H  
HETATM   30  H9  UNL     1       4.127  -0.320  -1.617  1.00  0.00           H  
HETATM   31  H10 UNL     1       5.195   2.416  -0.925  1.00  0.00           H  
HETATM   32  H11 UNL     1       2.515   2.999   0.456  1.00  0.00           H  
HETATM   33  H12 UNL     1       1.025   1.512   1.665  1.00  0.00           H  
HETATM   34  H13 UNL     1       1.545  -3.054   0.865  1.00  0.00           H  
HETATM   35  H14 UNL     1       0.137  -3.082   1.930  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3
CONECT    3    4    4    9
CONECT    4    5    6
CONECT    5   25
CONECT    6    7    7   26
CONECT    7    8   27
CONECT    8    9    9   20
CONECT    9   10
CONECT   10   11
CONECT   11   12   19   28
CONECT   12   13   13   18
CONECT   13   14   29
CONECT   14   15   15   30
CONECT   15   16   17
CONECT   16   31
CONECT   17   18   18   32
CONECT   18   33
CONECT   19   20   34   35
CONECT   20   21   21
END

HMDB0031420
     RDKit          3D
Heliannone C
 35 37  0  0  0  0  0  0  0  0999 V2000
   -1.8283    2.6217    0.6727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5225    1.4513    1.0621 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4056    0.3279    0.2856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3358    0.1704   -0.7416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3296    1.1065   -0.9643 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2754   -0.9347   -1.5584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2778   -1.8885   -1.3459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3595   -1.7437   -0.3402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4220   -0.6316    0.4801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4992   -0.4759    1.4988 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7632   -1.1122    1.5104 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6930   -0.3007    0.7377 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5793   -0.7866   -0.1942 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4388    0.0684   -0.8920 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4163    1.4201   -0.6603 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2848    2.2596   -1.3692 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5410    1.9197    0.2631 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6975    1.0661    0.9456 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6128   -2.5279    1.0641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3013   -2.7033   -0.0727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1576   -3.7003   -0.8180 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3750    3.1287   -0.1438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8227    2.3399    0.2879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7413    3.3287    1.5480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4384    1.9350   -0.4133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9704   -1.0950   -2.3598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2066   -2.7597   -1.9668 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1006   -1.1226    2.5688 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5985   -1.8331   -0.3755 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1269   -0.3203   -1.6174 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1950    2.4165   -0.9251 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5148    2.9991    0.4561 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0245    1.5123    1.6652 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5445   -3.0538    0.8651 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1374   -3.0818    1.9302 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
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 11 19  1  0
 19 20  1  0
 20 21  2  0
  9  3  1  0
 18 12  1  0
 20  8  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  5 25  1  0
  6 26  1  0
  7 27  1  0
 11 28  1  0
 13 29  1  0
 14 30  1  0
 16 31  1  0
 17 32  1  0
 18 33  1  0
 19 34  1  0
 19 35  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4',7-Dihydroxy-8-methoxyflavanone	HMDB

Chemical Formula

C₁₆H₁₄O₅

Average Molecular Weight

286.2794

Monoisotopic Molecular Weight

286.084123558

IUPAC Name

7-hydroxy-2-(4-hydroxyphenyl)-8-methoxy-3,4-dihydro-2H-1-benzopyran-4-one

Traditional Name

7-hydroxy-2-(4-hydroxyphenyl)-8-methoxy-2,3-dihydro-1-benzopyran-4-one

CAS Registry Number

Not Available

SMILES

COC1=C(O)C=CC2=C1OC(CC2=O)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C16H14O5/c1-20-16-12(18)7-6-11-13(19)8-14(21-15(11)16)9-2-4-10(17)5-3-9/h2-7,14,17-18H,8H2,1H3

InChI Key

BMGKZGNJRBKRFC-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

8-methoxyflavonoid-skeleton
4'-hydroxyflavonoid
7-hydroxyflavonoid
Flavanone
Hydroxyflavonoid
Flavan
Chromone
Chromane
Benzopyran
1-benzopyran
Anisole
Aryl alkyl ketone
Aryl ketone
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Benzenoid
Monocyclic benzene moiety
Ketone
Ether
Organoheterocyclic compound
Oxacycle
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

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	0.091 g/L	ALOGPS
logP	2.83	ALOGPS
logP	2.33	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	8.33	ChemAxon
pKa (Strongest Basic)	-4.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	75.77 m³·mol⁻¹	ChemAxon
Polarizability	29.16 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]+	166.041	31661259
DarkChem	[M-H]-	167.344	31661259
DeepCCS	[M+H]+	168.923	30932474
DeepCCS	[M-H]-	166.565	30932474
DeepCCS	[M-2H]-	199.451	30932474
DeepCCS	[M+Na]+	175.016	30932474
AllCCS	[M+H]+	166.8	32859911
AllCCS	[M+H-H2O]+	163.0	32859911
AllCCS	[M+NH4]+	170.3	32859911
AllCCS	[M+Na]+	171.3	32859911
AllCCS	[M-H]-	168.0	32859911
AllCCS	[M+Na-2H]-	167.4	32859911
AllCCS	[M+HCOO]-	167.0	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. Predicted by Afia on May 17, 2022.	6.01 minutes	32390414
Predicted by Siyang on May 30, 2022	11.9209 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.47 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1979.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	274.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	161.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	171.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	179.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	548.3 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	520.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	122.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1041.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	406.0 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	1251.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	359.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	372.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	398.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	236.6 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	96.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Heliannone C	COC1=C(O)C=CC2=C1OC(CC2=O)C1=CC=C(O)C=C1	3872.7	Standard polar	33892256
Heliannone C	COC1=C(O)C=CC2=C1OC(CC2=O)C1=CC=C(O)C=C1	2808.3	Standard non polar	33892256
Heliannone C	COC1=C(O)C=CC2=C1OC(CC2=O)C1=CC=C(O)C=C1	2810.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Heliannone C,1TMS,isomer #1	COC1=C(O[Si](C)(C)C)C=CC2=C1OC(C1=CC=C(O)C=C1)CC2=O	2756.4	Semi standard non polar	33892256
Heliannone C,1TMS,isomer #2	COC1=C(O)C=CC2=C1OC(C1=CC=C(O[Si](C)(C)C)C=C1)CC2=O	2801.8	Semi standard non polar	33892256
Heliannone C,2TMS,isomer #1	COC1=C(O[Si](C)(C)C)C=CC2=C1OC(C1=CC=C(O[Si](C)(C)C)C=C1)CC2=O	2817.7	Semi standard non polar	33892256
Heliannone C,1TBDMS,isomer #1	COC1=C(O[Si](C)(C)C(C)(C)C)C=CC2=C1OC(C1=CC=C(O)C=C1)CC2=O	3014.4	Semi standard non polar	33892256
Heliannone C,1TBDMS,isomer #2	COC1=C(O)C=CC2=C1OC(C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)CC2=O	3064.7	Semi standard non polar	33892256
Heliannone C,2TBDMS,isomer #1	COC1=C(O[Si](C)(C)C(C)(C)C)C=CC2=C1OC(C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)CC2=O	3279.8	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 - Heliannone C GC-MS (Non-derivatized) - 70eV, Positive	splash10-0abc-1390000000-988787b0e6de9c74c6e8	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Heliannone C GC-MS (2 TMS) - 70eV, Positive	splash10-06fr-2915400000-9b56272305042f759f88	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Heliannone C 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 - Heliannone C 10V, Positive-QTOF	splash10-000i-0290000000-7f6d33c4cb672f68c75c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heliannone C 20V, Positive-QTOF	splash10-014r-0980000000-a479737e1e651f69a69d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heliannone C 40V, Positive-QTOF	splash10-00xr-4900000000-d2dd59bb0a37aade06bb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heliannone C 10V, Negative-QTOF	splash10-000i-0090000000-a8ed99d5c5cf02f0e1ed	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heliannone C 20V, Negative-QTOF	splash10-000i-0290000000-60b6fea9d26c4c4ed991	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heliannone C 40V, Negative-QTOF	splash10-014m-4910000000-0759c87982c88a8f25bc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heliannone C 10V, Positive-QTOF	splash10-000i-0090000000-b239d41c6032c85540b2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heliannone C 20V, Positive-QTOF	splash10-014s-0940000000-5497bdee82f04a6f6265	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heliannone C 40V, Positive-QTOF	splash10-014i-0900000000-7bafa2bc433d383f79cf	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heliannone C 10V, Negative-QTOF	splash10-000i-0090000000-72ed1dce05f182779977	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heliannone C 20V, Negative-QTOF	splash10-00kr-0790000000-c36817d561a29186602d	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heliannone C 40V, Negative-QTOF	splash10-014i-0900000000-54857504b83711069fc9	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

FDB003497

KNApSAcK ID

Not Available

Chemspider ID

8812291

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10636929

PDB ID

Not Available

ChEBI ID

174725

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.. .

Enzymes

Enzyme Details

1. UDP-glucuronosyltransferase 1-1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:: UGT1A1
Uniprot ID:: P22309
Molecular weight:: 59590.91

Reactions

Heliannone C → 3,4,5-trihydroxy-6-[4-(7-hydroxy-8-methoxy-4-oxo-3,4-dihydro-2H-1-benzopyran-2-yl)phenoxy]oxane-2-carboxylic acid	details
Heliannone C → 3,4,5-trihydroxy-6-{[2-(4-hydroxyphenyl)-8-methoxy-4-oxo-3,4-dihydro-2H-1-benzopyran-7-yl]oxy}oxane-2-carboxylic acid	details

Enzyme Details

2. Sulfotransferase 1A3

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

Reactions

Heliannone C → [4-(7-hydroxy-8-methoxy-4-oxo-3,4-dihydro-2H-1-benzopyran-2-yl)phenyl]oxidanesulfonic acid	details

Showing metabocard for Heliannone C (HMDB0031420)

MOL for HMDB0031420 (Heliannone C)

3D MOL for HMDB0031420 (Heliannone C)

3D SDF for HMDB0031420 (Heliannone C)

3D-SDF for HMDB0031420 (Heliannone C)

PDB for HMDB0031420 (Heliannone C)

3D PDB for HMDB0031420 (Heliannone C)

SMILES for HMDB0031420 (Heliannone C)

INCHI for HMDB0031420 (Heliannone C)

Structure for HMDB0031420 (Heliannone C)

3D Structure for HMDB0031420 (Heliannone C)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions

Reactions