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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

HMDB0031421

Secondary Accession Numbers

HMDB31421

Metabolite Identification

Common Name

Heliannone B

Description

Heliannone B 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 B.

Structure

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

HMDB0031421
     RDKit          3D
Heliannone B
 38 40  0  0  0  0  0  0  0  0999 V2000
    5.8326    0.1869   -0.7444 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5748   -0.4104   -0.7086 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3845    0.3159   -0.5683 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4593    1.6895   -0.4600 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3115    2.4350   -0.3209 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0801    1.7919   -0.2907 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9924    0.3987   -0.3997 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1593   -0.3162   -0.5375 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0861   -1.6983   -0.6466 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1263   -2.5470    0.4766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2586   -0.2140   -0.3656 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3015    0.4629    0.2817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5777   -0.2462    0.2550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3487   -0.3440    1.3931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5717   -1.0177    1.3885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0492   -1.6095    0.2387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2759   -2.2866    0.2292 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2743   -1.5088   -0.8967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0571   -0.8369   -0.8869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4341    1.8391   -0.3850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1557    2.5385   -0.1456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1522    3.7447    0.1737 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0332    0.6879   -1.7321 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5945   -0.6004   -0.5636 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9870    0.9790    0.0155 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3928    2.2374   -0.4780 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3169    3.5116   -0.2325 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8429   -3.5716    0.1585 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1183   -2.6083    0.9508 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4129   -2.2166    1.2795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9774    0.6783    1.3257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0084    0.1065    2.3125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1841   -1.1001    2.2758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0935   -1.7353    0.0059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6616   -1.9819   -1.8048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4654   -0.7680   -1.7819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3090    2.3725    0.0243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5491    1.6417   -1.4627 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
  7 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 12 20  1  0
 20 21  1  0
 21 22  2  0
  8  3  1  0
 19 13  1  0
 21  6  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  5 27  1  0
 10 28  1  0
 10 29  1  0
 10 30  1  0
 12 31  1  0
 14 32  1  0
 15 33  1  0
 17 34  1  0
 18 35  1  0
 19 36  1  0
 20 37  1  0
 20 38  1  0
M  END


  Mrv0541 05061305562D          

 22 24  0  0  0  0            999 V2000
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -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
    3.5724    1.2375    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
    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
    3.5724    2.0625    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
    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
  5  3  1  0  0  0  0
  6  4  2  0  0  0  0
  8  7  2  0  0  0  0
 10  3  2  0  0  0  0
 10  4  1  0  0  0  0
 11  5  2  0  0  0  0
 11  6  1  0  0  0  0
 12  7  1  0  0  0  0
 13  9  1  0  0  0  0
 13 12  1  0  0  0  0
 14  8  1  0  0  0  0
 15  9  1  0  0  0  0
 15 10  1  0  0  0  0
 16 12  2  0  0  0  0
 17 14  2  0  0  0  0
 17 16  1  0  0  0  0
 18 11  1  0  0  0  0
 19 13  2  0  0  0  0
 20  1  1  0  0  0  0
 20 14  1  0  0  0  0
 21  2  1  0  0  0  0
 21 17  1  0  0  0  0
 22 15  1  0  0  0  0
 22 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0031421

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(OC)C2=C(C=C1)C(=O)CC(O2)C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H16O5/c1-20-14-8-7-12-13(19)9-15(22-16(12)17(14)21-2)10-3-5-11(18)6-4-10/h3-8,15,18H,9H2,1-2H3

> <INCHI_KEY>
JICUYFPHCQPXNY-UHFFFAOYSA-N

> <FORMULA>
C17H16O5

> <MOLECULAR_WEIGHT>
300.3059

> <EXACT_MASS>
300.099773622

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
31.241586293016844

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.57

> <JCHEM_LOGP>
2.476896162333333

> <ALOGPS_LOGS>
-3.83

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.950471811827615

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.47166286771319

> <JCHEM_PKA_STRONGEST_BASIC>
-4.485562166768913

> <JCHEM_POLAR_SURFACE_AREA>
64.99000000000001

> <JCHEM_REFRACTIVITY>
80.2544

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.49e-02 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0031421
     RDKit          3D
Heliannone B
 38 40  0  0  0  0  0  0  0  0999 V2000
    5.8326    0.1869   -0.7444 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5748   -0.4104   -0.7086 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3845    0.3159   -0.5683 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4593    1.6895   -0.4600 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3115    2.4350   -0.3209 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0801    1.7919   -0.2907 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9924    0.3987   -0.3997 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1593   -0.3162   -0.5375 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0861   -1.6983   -0.6466 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1263   -2.5470    0.4766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2586   -0.2140   -0.3656 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3015    0.4629    0.2817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5777   -0.2462    0.2550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3487   -0.3440    1.3931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5717   -1.0177    1.3885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0492   -1.6095    0.2387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2759   -2.2866    0.2292 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2743   -1.5088   -0.8967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0571   -0.8369   -0.8869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4341    1.8391   -0.3850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1557    2.5385   -0.1456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1522    3.7447    0.1737 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0332    0.6879   -1.7321 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5945   -0.6004   -0.5636 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9870    0.9790    0.0155 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3928    2.2374   -0.4780 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3169    3.5116   -0.2325 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8429   -3.5716    0.1585 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1183   -2.6083    0.9508 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4129   -2.2166    1.2795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9774    0.6783    1.3257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0084    0.1065    2.3125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1841   -1.1001    2.2758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0935   -1.7353    0.0059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6616   -1.9819   -1.8048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4654   -0.7680   -1.7819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3090    2.3725    0.0243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5491    1.6417   -1.4627 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
  7 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 12 20  1  0
 20 21  1  0
 21 22  2  0
  8  3  1  0
 19 13  1  0
 21  6  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  5 27  1  0
 10 28  1  0
 10 29  1  0
 10 30  1  0
 12 31  1  0
 14 32  1  0
 15 33  1  0
 17 34  1  0
 18 35  1  0
 19 36  1  0
 20 37  1  0
 20 38  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       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335   1.540   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       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      13.337  -3.080   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       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
CONECT    1   20                                                            
CONECT    2   21                                                            
CONECT    3    5   10                                                       
CONECT    4    6   10                                                       
CONECT    5    3   11                                                       
CONECT    6    4   11                                                       
CONECT    7    8   12                                                       
CONECT    8    7   14                                                       
CONECT    9   13   15                                                       
CONECT   10    3    4   15                                                  
CONECT   11    5    6   18                                                  
CONECT   12    7   13   16                                                  
CONECT   13    9   12   19                                                  
CONECT   14    8   17   20                                                  
CONECT   15    9   10   22                                                  
CONECT   16   12   17   22                                                  
CONECT   17   14   16   21                                                  
CONECT   18   11                                                            
CONECT   19   13                                                            
CONECT   20    1   14                                                       
CONECT   21    2   17                                                       
CONECT   22   15   16                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

COMPND    HMDB0031421
HETATM    1  C1  UNL     1       5.833   0.187  -0.744  1.00  0.00           C  
HETATM    2  O1  UNL     1       4.575  -0.410  -0.709  1.00  0.00           O  
HETATM    3  C2  UNL     1       3.385   0.316  -0.568  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.459   1.690  -0.460  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.312   2.435  -0.321  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.080   1.792  -0.291  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.992   0.399  -0.400  1.00  0.00           C  
HETATM    8  C7  UNL     1       2.159  -0.316  -0.538  1.00  0.00           C  
HETATM    9  O2  UNL     1       2.086  -1.698  -0.647  1.00  0.00           O  
HETATM   10  C8  UNL     1       2.126  -2.547   0.477  1.00  0.00           C  
HETATM   11  O3  UNL     1      -0.259  -0.214  -0.366  1.00  0.00           O  
HETATM   12  C9  UNL     1      -1.301   0.463   0.282  1.00  0.00           C  
HETATM   13  C10 UNL     1      -2.578  -0.246   0.255  1.00  0.00           C  
HETATM   14  C11 UNL     1      -3.349  -0.344   1.393  1.00  0.00           C  
HETATM   15  C12 UNL     1      -4.572  -1.018   1.388  1.00  0.00           C  
HETATM   16  C13 UNL     1      -5.049  -1.610   0.239  1.00  0.00           C  
HETATM   17  O4  UNL     1      -6.276  -2.287   0.229  1.00  0.00           O  
HETATM   18  C14 UNL     1      -4.274  -1.509  -0.897  1.00  0.00           C  
HETATM   19  C15 UNL     1      -3.057  -0.837  -0.887  1.00  0.00           C  
HETATM   20  C16 UNL     1      -1.434   1.839  -0.385  1.00  0.00           C  
HETATM   21  C17 UNL     1      -0.156   2.538  -0.146  1.00  0.00           C  
HETATM   22  O5  UNL     1      -0.152   3.745   0.174  1.00  0.00           O  
HETATM   23  H1  UNL     1       6.033   0.688  -1.732  1.00  0.00           H  
HETATM   24  H2  UNL     1       6.595  -0.600  -0.564  1.00  0.00           H  
HETATM   25  H3  UNL     1       5.987   0.979   0.016  1.00  0.00           H  
HETATM   26  H4  UNL     1       4.393   2.237  -0.478  1.00  0.00           H  
HETATM   27  H5  UNL     1       2.317   3.512  -0.233  1.00  0.00           H  
HETATM   28  H6  UNL     1       1.843  -3.572   0.159  1.00  0.00           H  
HETATM   29  H7  UNL     1       3.118  -2.608   0.951  1.00  0.00           H  
HETATM   30  H8  UNL     1       1.413  -2.217   1.279  1.00  0.00           H  
HETATM   31  H9  UNL     1      -0.977   0.678   1.326  1.00  0.00           H  
HETATM   32  H10 UNL     1      -3.008   0.106   2.313  1.00  0.00           H  
HETATM   33  H11 UNL     1      -5.184  -1.100   2.276  1.00  0.00           H  
HETATM   34  H12 UNL     1      -7.094  -1.735   0.006  1.00  0.00           H  
HETATM   35  H13 UNL     1      -4.662  -1.982  -1.805  1.00  0.00           H  
HETATM   36  H14 UNL     1      -2.465  -0.768  -1.782  1.00  0.00           H  
HETATM   37  H15 UNL     1      -2.309   2.372   0.024  1.00  0.00           H  
HETATM   38  H16 UNL     1      -1.549   1.642  -1.463  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3
CONECT    3    4    4    8
CONECT    4    5   26
CONECT    5    6    6   27
CONECT    6    7   21
CONECT    7    8    8   11
CONECT    8    9
CONECT    9   10
CONECT   10   28   29   30
CONECT   11   12
CONECT   12   13   20   31
CONECT   13   14   14   19
CONECT   14   15   32
CONECT   15   16   16   33
CONECT   16   17   18
CONECT   17   34
CONECT   18   19   19   35
CONECT   19   36
CONECT   20   21   37   38
CONECT   21   22   22
END

HMDB0031421
     RDKit          3D
Heliannone B
 38 40  0  0  0  0  0  0  0  0999 V2000
    5.8326    0.1869   -0.7444 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5748   -0.4104   -0.7086 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3845    0.3159   -0.5683 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4593    1.6895   -0.4600 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3115    2.4350   -0.3209 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0801    1.7919   -0.2907 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9924    0.3987   -0.3997 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1593   -0.3162   -0.5375 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0861   -1.6983   -0.6466 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1263   -2.5470    0.4766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2586   -0.2140   -0.3656 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3015    0.4629    0.2817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5777   -0.2462    0.2550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3487   -0.3440    1.3931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5717   -1.0177    1.3885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0492   -1.6095    0.2387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2759   -2.2866    0.2292 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2743   -1.5088   -0.8967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0571   -0.8369   -0.8869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4341    1.8391   -0.3850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1557    2.5385   -0.1456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1522    3.7447    0.1737 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0332    0.6879   -1.7321 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5945   -0.6004   -0.5636 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9870    0.9790    0.0155 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3928    2.2374   -0.4780 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3169    3.5116   -0.2325 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8429   -3.5716    0.1585 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1183   -2.6083    0.9508 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4129   -2.2166    1.2795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9774    0.6783    1.3257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0084    0.1065    2.3125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1841   -1.1001    2.2758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0935   -1.7353    0.0059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6616   -1.9819   -1.8048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4654   -0.7680   -1.7819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3090    2.3725    0.0243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5491    1.6417   -1.4627 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
  7 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 12 20  1  0
 20 21  1  0
 21 22  2  0
  8  3  1  0
 19 13  1  0
 21  6  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  5 27  1  0
 10 28  1  0
 10 29  1  0
 10 30  1  0
 12 31  1  0
 14 32  1  0
 15 33  1  0
 17 34  1  0
 18 35  1  0
 19 36  1  0
 20 37  1  0
 20 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4'-Hydroxy-7,8-dimethoxyflavanone	HMDB
(R,S)-Heliannone b	HMDB
Heliannone b	MeSH

Chemical Formula

C₁₇H₁₆O₅

Average Molecular Weight

300.3059

Monoisotopic Molecular Weight

300.099773622

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

COC1=C(OC)C2=C(C=C1)C(=O)CC(O2)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C17H16O5/c1-20-14-8-7-12-13(19)9-15(22-16(12)17(14)21-2)10-3-5-11(18)6-4-10/h3-8,15,18H,9H2,1-2H3

InChI Key

JICUYFPHCQPXNY-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

7-methoxyflavonoid-skeleton
8-methoxyflavonoid-skeleton
4'-hydroxyflavonoid
Flavanone
Hydroxyflavonoid
Monohydroxyflavonoid
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

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0031421)
Cell membrane (HMDB: HMDB0031421)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0031421)

Source

Endogenous

Endogenous (HMDB: HMDB0031421)

Plant

Plant (HMDB: HMDB0031421)

Exogenous

Food

Food (HMDB: HMDB0031421)

Fat and oil

Fats and oils (FooDB: FOOD00864)

Exogenous (HMDB: HMDB0031421)

Process

Not Available

Role

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	0.045 g/L	ALOGPS
logP	2.57	ALOGPS
logP	2.48	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	9.47	ChemAxon
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	64.99 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	80.25 m³·mol⁻¹	ChemAxon
Polarizability	31.24 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]+	170.689	31661259
DarkChem	[M-H]-	169.083	31661259
DeepCCS	[M+H]+	178.436	30932474
DeepCCS	[M-H]-	176.078	30932474
DeepCCS	[M-2H]-	209.989	30932474
DeepCCS	[M+Na]+	185.215	30932474
AllCCS	[M+H]+	171.0	32859911
AllCCS	[M+H-H2O]+	167.4	32859911
AllCCS	[M+NH4]+	174.4	32859911
AllCCS	[M+Na]+	175.4	32859911
AllCCS	[M-H]-	173.3	32859911
AllCCS	[M+Na-2H]-	172.9	32859911
AllCCS	[M+HCOO]-	172.5	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.	6.72 minutes	32390414
Predicted by Siyang on May 30, 2022	13.4196 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.48 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2156.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	307.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	179.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	185.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	165.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	551.6 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	612.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	132.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1155.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	435.7 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	1373.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	405.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	381.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	366.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	276.0 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	46.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Heliannone B	COC1=C(OC)C2=C(C=C1)C(=O)CC(O2)C1=CC=C(O)C=C1	3881.4	Standard polar	33892256
Heliannone B	COC1=C(OC)C2=C(C=C1)C(=O)CC(O2)C1=CC=C(O)C=C1	2739.2	Standard non polar	33892256
Heliannone B	COC1=C(OC)C2=C(C=C1)C(=O)CC(O2)C1=CC=C(O)C=C1	2833.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Heliannone B,1TMS,isomer #1	COC1=CC=C2C(=O)CC(C3=CC=C(O[Si](C)(C)C)C=C3)OC2=C1OC	2783.5	Semi standard non polar	33892256
Heliannone B,1TBDMS,isomer #1	COC1=CC=C2C(=O)CC(C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3)OC2=C1OC	3036.4	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 - Heliannone B GC-MS (Non-derivatized) - 70eV, Positive	splash10-0kmr-1290000000-1c1345753d5a885bde13	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Heliannone B GC-MS (1 TMS) - 70eV, Positive	splash10-05fr-4619000000-313031f79fda2649006f	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Heliannone B GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Heliannone B 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 B 10V, Positive-QTOF	splash10-0udi-0229000000-aa790682ffad3c2a0c24	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heliannone B 20V, Positive-QTOF	splash10-0f89-0966000000-835d04581a9041e6ce98	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heliannone B 40V, Positive-QTOF	splash10-00di-3900000000-828b50fc2e87f91713f0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heliannone B 10V, Negative-QTOF	splash10-0002-0090000000-9affbf1ba508497284b0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heliannone B 20V, Negative-QTOF	splash10-0002-0190000000-ba68d7dda152229f6e9b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heliannone B 40V, Negative-QTOF	splash10-01bc-5950000000-99cc3b999445a3139cc6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heliannone B 10V, Positive-QTOF	splash10-0udi-0409000000-b02d4b590dbcb0c1e2d0	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heliannone B 20V, Positive-QTOF	splash10-001i-0900000000-076710b564eade839c4b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heliannone B 40V, Positive-QTOF	splash10-001i-0900000000-0ffee3bd56147e34b246	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

FDB003498

KNApSAcK ID

C00039356

Chemspider ID

9027042

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10851748

PDB ID

Not Available

ChEBI ID

174861

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 Heliannone B (HMDB0031421)

MOL for HMDB0031421 (Heliannone B)

3D MOL for HMDB0031421 (Heliannone B)

3D SDF for HMDB0031421 (Heliannone B)

3D-SDF for HMDB0031421 (Heliannone B)

PDB for HMDB0031421 (Heliannone B)

3D PDB for HMDB0031421 (Heliannone B)

SMILES for HMDB0031421 (Heliannone B)

INCHI for HMDB0031421 (Heliannone B)

Structure for HMDB0031421 (Heliannone B)

3D Structure for HMDB0031421 (Heliannone B)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra