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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:44:56 UTC

Update Date

2022-03-07 02:53:05 UTC

HMDB ID

HMDB0031705

Secondary Accession Numbers

HMDB31705

Metabolite Identification

Common Name

Heliannone A

Description

Heliannone A belongs to the class of organic compounds known as 2'-hydroxychalcones. These are organic compounds containing chalcone skeleton that carries a hydroxyl group at the 2'-position. Thus, heliannone a is considered to be a flavonoid. Heliannone A has been detected, but not quantified in, fats and oils and sunflowers (Helianthus annuus). This could make heliannone a a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Heliannone A.

Structure

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

HMDB0031705
     RDKit          3D
Heliannone A
 38 39  0  0  0  0  0  0  0  0999 V2000
   -4.5748   -0.4589    3.2638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6800   -0.4465    1.8315 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5276   -0.3623    1.0515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2790   -0.2897    1.6012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1380   -0.2058    0.7868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1930   -0.1909   -0.5830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0347   -0.1050   -1.4548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3407   -0.1069   -2.7498 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3550   -0.0191   -1.2379 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1131    0.0149   -0.1951 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5906    0.1100   -0.2422 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3297    0.1731   -1.3861 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7135    0.2613   -1.3758 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3602    0.2857   -0.1638 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7591    0.3746   -0.1290 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6727    0.2254    1.0219 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2829    0.1377    0.9459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4801   -0.2657   -1.1471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6873   -0.2612   -2.4727 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6166   -0.3498   -0.3005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8608   -0.4214   -0.9012 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6578    0.6736   -1.2355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0723    0.5125    3.5404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5678   -0.4227    3.7315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9212   -1.2592    3.6063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1983   -0.2991    2.6827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2126   -0.1534    1.2977 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9609    0.0330   -2.1943 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6510   -0.0281    0.7664 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8720    0.1573   -2.3521 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2626    0.3089   -2.2834 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1937    1.2672   -0.1048 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1960    0.2455    1.9713 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7283    0.0896    1.8596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2843   -0.2244   -3.2938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7929    0.6642   -2.3513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6762    0.4935   -0.8232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2453    1.6488   -0.9815 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
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
  6 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
 21 22  1  0
 20  3  1  0
 17 11  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  5 27  1  0
  9 28  1  0
 10 29  1  0
 12 30  1  0
 13 31  1  0
 15 32  1  0
 16 33  1  0
 17 34  1  0
 19 35  1  0
 22 36  1  0
 22 37  1  0
 22 38  1  0
M  END


  Mrv0541 05061306052D          

 22 23  0  0  0  0            999 V2000
   -7.1447   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -5.3625    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
   -4.2868    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
   -2.8579    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
   -5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -0.4125    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
   -5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -4.1250    0.0000 C   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
   -3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  3  1  0  0  0  0
  7  4  2  0  0  0  0
  9  5  2  0  0  0  0
 10  8  2  0  0  0  0
 11  3  2  0  0  0  0
 11  4  1  0  0  0  0
 11  5  1  0  0  0  0
 12  6  2  0  0  0  0
 12  7  1  0  0  0  0
 13  8  1  0  0  0  0
 14  9  1  0  0  0  0
 14 13  1  0  0  0  0
 15 10  1  0  0  0  0
 16 13  2  0  0  0  0
 17 15  2  0  0  0  0
 17 16  1  0  0  0  0
 18 12  1  0  0  0  0
 19 14  2  0  0  0  0
 20 16  1  0  0  0  0
 21  1  1  0  0  0  0
 21 15  1  0  0  0  0
 22  2  1  0  0  0  0
 22 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0031705

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C17H16O5/c1-21-15-10-8-13(16(20)17(15)22-2)14(19)9-5-11-3-6-12(18)7-4-11/h3-10,18,20H,1-2H3/b9-5+

> <INCHI_KEY>
RURQJVCNVGERHF-WEVVVXLNSA-N

> <FORMULA>
C17H16O5

> <MOLECULAR_WEIGHT>
300.3059

> <EXACT_MASS>
300.099773622

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
31.72207592217618

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-1-(2-hydroxy-3,4-dimethoxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one

> <ALOGPS_LOGP>
3.44

> <JCHEM_LOGP>
3.617852134333333

> <ALOGPS_LOGS>
-4.11

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.206586625488459

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.547697822742984

> <JCHEM_PKA_STRONGEST_BASIC>
-4.638663589877825

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
83.7652

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.35e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
heliannone A

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0031705
     RDKit          3D
Heliannone A
 38 39  0  0  0  0  0  0  0  0999 V2000
   -4.5748   -0.4589    3.2638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6800   -0.4465    1.8315 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5276   -0.3623    1.0515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2790   -0.2897    1.6012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1380   -0.2058    0.7868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1930   -0.1909   -0.5830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0347   -0.1050   -1.4548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3407   -0.1069   -2.7498 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3550   -0.0191   -1.2379 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1131    0.0149   -0.1951 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5906    0.1100   -0.2422 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3297    0.1731   -1.3861 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7135    0.2613   -1.3758 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3602    0.2857   -0.1638 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7591    0.3746   -0.1290 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6727    0.2254    1.0219 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2829    0.1377    0.9459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4801   -0.2657   -1.1471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6873   -0.2612   -2.4727 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6166   -0.3498   -0.3005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8608   -0.4214   -0.9012 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6578    0.6736   -1.2355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0723    0.5125    3.5404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5678   -0.4227    3.7315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9212   -1.2592    3.6063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1983   -0.2991    2.6827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2126   -0.1534    1.2977 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9609    0.0330   -2.1943 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6510   -0.0281    0.7664 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8720    0.1573   -2.3521 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2626    0.3089   -2.2834 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1937    1.2672   -0.1048 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1960    0.2455    1.9713 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7283    0.0896    1.8596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2843   -0.2244   -3.2938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7929    0.6642   -2.3513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6762    0.4935   -0.8232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2453    1.6488   -0.9815 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
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
  6 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
 21 22  1  0
 20  3  1  0
 17 11  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  5 27  1  0
  9 28  1  0
 10 29  1  0
 12 30  1  0
 13 31  1  0
 15 32  1  0
 16 33  1  0
 17 34  1  0
 19 35  1  0
 22 36  1  0
 22 37  1  0
 22 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     -13.337  -9.240   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -9.336 -10.010   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.335   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -8.002   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -8.002   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0     -10.669  -4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0     -12.003  -5.390   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -6.668   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0     -12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0     -10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -6.668   3.850   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -8.002  -7.700   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0     -13.337  -7.700   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0     -10.669  -9.240   0.000  0.00  0.00           O+0
CONECT    1   21                                                            
CONECT    2   22                                                            
CONECT    3    6   11                                                       
CONECT    4    7   11                                                       
CONECT    5    9   11                                                       
CONECT    6    3   12                                                       
CONECT    7    4   12                                                       
CONECT    8   10   13                                                       
CONECT    9    5   14                                                       
CONECT   10    8   15                                                       
CONECT   11    3    4    5                                                  
CONECT   12    6    7   18                                                  
CONECT   13    8   14   16                                                  
CONECT   14    9   13   19                                                  
CONECT   15   10   17   21                                                  
CONECT   16   13   17   20                                                  
CONECT   17   15   16   22                                                  
CONECT   18   12                                                            
CONECT   19   14                                                            
CONECT   20   16                                                            
CONECT   21    1   15                                                       
CONECT   22    2   17                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

COMPND    HMDB0031705
HETATM    1  C1  UNL     1      -4.575  -0.459   3.264  1.00  0.00           C  
HETATM    2  O1  UNL     1      -4.680  -0.446   1.831  1.00  0.00           O  
HETATM    3  C2  UNL     1      -3.528  -0.362   1.051  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.279  -0.290   1.601  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.138  -0.206   0.787  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.193  -0.191  -0.583  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.035  -0.105  -1.455  1.00  0.00           C  
HETATM    8  O2  UNL     1      -0.341  -0.107  -2.750  1.00  0.00           O  
HETATM    9  C7  UNL     1       1.355  -0.019  -1.238  1.00  0.00           C  
HETATM   10  C8  UNL     1       2.113   0.015  -0.195  1.00  0.00           C  
HETATM   11  C9  UNL     1       3.591   0.110  -0.242  1.00  0.00           C  
HETATM   12  C10 UNL     1       4.330   0.173  -1.386  1.00  0.00           C  
HETATM   13  C11 UNL     1       5.714   0.261  -1.376  1.00  0.00           C  
HETATM   14  C12 UNL     1       6.360   0.286  -0.164  1.00  0.00           C  
HETATM   15  O3  UNL     1       7.759   0.375  -0.129  1.00  0.00           O  
HETATM   16  C13 UNL     1       5.673   0.225   1.022  1.00  0.00           C  
HETATM   17  C14 UNL     1       4.283   0.138   0.946  1.00  0.00           C  
HETATM   18  C15 UNL     1      -2.480  -0.266  -1.147  1.00  0.00           C  
HETATM   19  O4  UNL     1      -2.687  -0.261  -2.473  1.00  0.00           O  
HETATM   20  C16 UNL     1      -3.617  -0.350  -0.300  1.00  0.00           C  
HETATM   21  O5  UNL     1      -4.861  -0.421  -0.901  1.00  0.00           O  
HETATM   22  C17 UNL     1      -5.658   0.674  -1.235  1.00  0.00           C  
HETATM   23  H1  UNL     1      -4.072   0.512   3.540  1.00  0.00           H  
HETATM   24  H2  UNL     1      -5.568  -0.423   3.732  1.00  0.00           H  
HETATM   25  H3  UNL     1      -3.921  -1.259   3.606  1.00  0.00           H  
HETATM   26  H4  UNL     1      -2.198  -0.299   2.683  1.00  0.00           H  
HETATM   27  H5  UNL     1      -0.213  -0.153   1.298  1.00  0.00           H  
HETATM   28  H6  UNL     1       1.961   0.033  -2.194  1.00  0.00           H  
HETATM   29  H7  UNL     1       1.651  -0.028   0.766  1.00  0.00           H  
HETATM   30  H8  UNL     1       3.872   0.157  -2.352  1.00  0.00           H  
HETATM   31  H9  UNL     1       6.263   0.309  -2.283  1.00  0.00           H  
HETATM   32  H10 UNL     1       8.194   1.267  -0.105  1.00  0.00           H  
HETATM   33  H11 UNL     1       6.196   0.246   1.971  1.00  0.00           H  
HETATM   34  H12 UNL     1       3.728   0.090   1.860  1.00  0.00           H  
HETATM   35  H13 UNL     1      -2.284  -0.224  -3.294  1.00  0.00           H  
HETATM   36  H14 UNL     1      -5.793   0.664  -2.351  1.00  0.00           H  
HETATM   37  H15 UNL     1      -6.676   0.493  -0.823  1.00  0.00           H  
HETATM   38  H16 UNL     1      -5.245   1.649  -0.981  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3
CONECT    3    4    4   20
CONECT    4    5   26
CONECT    5    6    6   27
CONECT    6    7   18
CONECT    7    8    8    9
CONECT    9   10   10   28
CONECT   10   11   29
CONECT   11   12   12   17
CONECT   12   13   30
CONECT   13   14   14   31
CONECT   14   15   16
CONECT   15   32
CONECT   16   17   17   33
CONECT   17   34
CONECT   18   19   20   20
CONECT   19   35
CONECT   20   21
CONECT   21   22
CONECT   22   36   37   38
END

HMDB0031705
     RDKit          3D
Heliannone A
 38 39  0  0  0  0  0  0  0  0999 V2000
   -4.5748   -0.4589    3.2638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6800   -0.4465    1.8315 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5276   -0.3623    1.0515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2790   -0.2897    1.6012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1380   -0.2058    0.7868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1930   -0.1909   -0.5830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0347   -0.1050   -1.4548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3407   -0.1069   -2.7498 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3550   -0.0191   -1.2379 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1131    0.0149   -0.1951 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5906    0.1100   -0.2422 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3297    0.1731   -1.3861 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7135    0.2613   -1.3758 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3602    0.2857   -0.1638 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7591    0.3746   -0.1290 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6727    0.2254    1.0219 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2829    0.1377    0.9459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4801   -0.2657   -1.1471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6873   -0.2612   -2.4727 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6166   -0.3498   -0.3005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8608   -0.4214   -0.9012 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6578    0.6736   -1.2355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0723    0.5125    3.5404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5678   -0.4227    3.7315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9212   -1.2592    3.6063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1983   -0.2991    2.6827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2126   -0.1534    1.2977 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9609    0.0330   -2.1943 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6510   -0.0281    0.7664 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8720    0.1573   -2.3521 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2626    0.3089   -2.2834 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1937    1.2672   -0.1048 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1960    0.2455    1.9713 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7283    0.0896    1.8596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2843   -0.2244   -3.2938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7929    0.6642   -2.3513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6762    0.4935   -0.8232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2453    1.6488   -0.9815 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
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
  6 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
 21 22  1  0
 20  3  1  0
 17 11  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  5 27  1  0
  9 28  1  0
 10 29  1  0
 12 30  1  0
 13 31  1  0
 15 32  1  0
 16 33  1  0
 17 34  1  0
 19 35  1  0
 22 36  1  0
 22 37  1  0
 22 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2',4-Dihydroxy-3',4'-dimethoxychalcone	HMDB

Chemical Formula

C₁₇H₁₆O₅

Average Molecular Weight

300.3059

Monoisotopic Molecular Weight

300.099773622

IUPAC Name

(2E)-1-(2-hydroxy-3,4-dimethoxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one

Traditional Name

heliannone A

CAS Registry Number

193411-10-8

SMILES

COC1=C(OC)C(O)=C(C=C1)C(=O)\C=C\C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C17H16O5/c1-21-15-10-8-13(16(20)17(15)22-2)14(19)9-5-11-3-6-12(18)7-4-11/h3-10,18,20H,1-2H3/b9-5+

InChI Key

RURQJVCNVGERHF-WEVVVXLNSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2'-hydroxychalcones. These are organic compounds containing chalcone skeleton that carries a hydroxyl group at the 2'-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Linear 1,3-diarylpropanoids

Sub Class

Chalcones and dihydrochalcones

Direct Parent

2'-Hydroxychalcones

Alternative Parents

Substituents

2'-hydroxychalcone
Cinnamylphenol
Hydroxycinnamic acid or derivatives
Methoxyphenol
Dimethoxybenzene
O-dimethoxybenzene
Benzoyl
Phenoxy compound
Phenol ether
Styrene
Aryl ketone
Anisole
Methoxybenzene
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Phenol
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
Enone
Vinylogous acid
Acryloyl-group
Alpha,beta-unsaturated ketone
Ketone
Ether
Organic oxygen compound
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Chalcones and dihydrochalcones (LMPK12120154 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0031705)
Cell membrane (HMDB: HMDB0031705)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0031705)

Source

Endogenous

Endogenous (HMDB: HMDB0031705)

Plant

Plant (HMDB: HMDB0031705)

Exogenous

Food

Food (HMDB: HMDB0031705)

Herb and spice

Oilseed crop

Sunflower (FooDB: FOOD00086)

Fat and oil

Fats and oils (FooDB: FOOD00864)

Exogenous (HMDB: HMDB0031705)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	144 - 146 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	166.8 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.024 g/L	ALOGPS
logP	3.44	ALOGPS
logP	3.62	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	8.55	ChemAxon
pKa (Strongest Basic)	-4.6	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	5	ChemAxon
Refractivity	83.77 m³·mol⁻¹	ChemAxon
Polarizability	31.72 Å³	ChemAxon
Number of Rings	2	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]+	174.618	30932474
DeepCCS	[M-H]-	172.26	30932474
DeepCCS	[M-2H]-	206.311	30932474
DeepCCS	[M+Na]+	181.538	30932474
AllCCS	[M+H]+	171.1	32859911
AllCCS	[M+H-H2O]+	167.5	32859911
AllCCS	[M+NH4]+	174.5	32859911
AllCCS	[M+Na]+	175.5	32859911
AllCCS	[M-H]-	171.4	32859911
AllCCS	[M+Na-2H]-	171.1	32859911
AllCCS	[M+HCOO]-	170.9	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.	7.42 minutes	32390414
Predicted by Siyang on May 30, 2022	13.0953 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.09 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2354.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	296.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	171.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	176.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	247.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	639.5 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	627.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	116.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1298.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	474.2 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	1329.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	412.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	445.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	364.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	235.9 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	27.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Heliannone A	COC1=C(OC)C(O)=C(C=C1)C(=O)\C=C\C1=CC=C(O)C=C1	4588.0	Standard polar	33892256
Heliannone A	COC1=C(OC)C(O)=C(C=C1)C(=O)\C=C\C1=CC=C(O)C=C1	2850.5	Standard non polar	33892256
Heliannone A	COC1=C(OC)C(O)=C(C=C1)C(=O)\C=C\C1=CC=C(O)C=C1	3052.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Heliannone A,1TMS,isomer #1	COC1=CC=C(C(=O)/C=C/C2=CC=C(O)C=C2)C(O[Si](C)(C)C)=C1OC	2854.2	Semi standard non polar	33892256
Heliannone A,1TMS,isomer #2	COC1=CC=C(C(=O)/C=C/C2=CC=C(O[Si](C)(C)C)C=C2)C(O)=C1OC	2895.9	Semi standard non polar	33892256
Heliannone A,2TMS,isomer #1	COC1=CC=C(C(=O)/C=C/C2=CC=C(O[Si](C)(C)C)C=C2)C(O[Si](C)(C)C)=C1OC	2870.8	Semi standard non polar	33892256
Heliannone A,1TBDMS,isomer #1	COC1=CC=C(C(=O)/C=C/C2=CC=C(O)C=C2)C(O[Si](C)(C)C(C)(C)C)=C1OC	3129.6	Semi standard non polar	33892256
Heliannone A,1TBDMS,isomer #2	COC1=CC=C(C(=O)/C=C/C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)C(O)=C1OC	3202.1	Semi standard non polar	33892256
Heliannone A,2TBDMS,isomer #1	COC1=CC=C(C(=O)/C=C/C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)C(O[Si](C)(C)C(C)(C)C)=C1OC	3407.0	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 A GC-MS (Non-derivatized) - 70eV, Positive	splash10-00yr-1971000000-bb359f4a8d4ba3534d58	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Heliannone A GC-MS (2 TMS) - 70eV, Positive	splash10-00fr-4135900000-bd0c240c770e4e2690e3	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Heliannone A 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 A 10V, Positive-QTOF	splash10-0udi-0229000000-cf7228c27e293b082543	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heliannone A 20V, Positive-QTOF	splash10-0f8a-0943000000-c38fe12f054fc55d50da	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heliannone A 40V, Positive-QTOF	splash10-015a-3910000000-f32366dd919faa6a0bf2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heliannone A 10V, Negative-QTOF	splash10-0002-0290000000-3958d364ea7ac5f3934f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heliannone A 20V, Negative-QTOF	splash10-0002-0490000000-02cb8c08d9f54d6bfc2e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heliannone A 40V, Negative-QTOF	splash10-0pvr-4940000000-1004ceb4c8ef4310d18b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heliannone A 10V, Positive-QTOF	splash10-0udi-0109000000-04b79e4e7cad4564861f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heliannone A 20V, Positive-QTOF	splash10-0002-0901000000-1a1b4ef41c021b54bf03	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heliannone A 40V, Positive-QTOF	splash10-0api-1920000000-a5d2c89a1563c6d7216e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heliannone A 10V, Negative-QTOF	splash10-0002-0190000000-4eeae988ca0210d5db47	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heliannone A 20V, Negative-QTOF	splash10-014j-0790000000-b68b18eb0c583d0584ba	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heliannone A 40V, Negative-QTOF	splash10-014i-2970000000-69835a21cdf6487bb3f7	2021-09-22	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

FDB008368

KNApSAcK ID

C00014421

Chemspider ID

4512710

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5357345

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1827531

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 A (HMDB0031705)

MOL for HMDB0031705 (Heliannone A)

3D MOL for HMDB0031705 (Heliannone A)

3D SDF for HMDB0031705 (Heliannone A)

3D-SDF for HMDB0031705 (Heliannone A)

PDB for HMDB0031705 (Heliannone A)

3D PDB for HMDB0031705 (Heliannone A)

SMILES for HMDB0031705 (Heliannone A)

INCHI for HMDB0031705 (Heliannone A)

Structure for HMDB0031705 (Heliannone A)

3D Structure for HMDB0031705 (Heliannone A)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra