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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:53:15 UTC

Update Date

2022-03-07 02:53:33 UTC

HMDB ID

HMDB0033015

Secondary Accession Numbers

HMDB33015

Metabolite Identification

Common Name

5,6-Dihydroyangonin

Description

5,6-Dihydroyangonin belongs to the class of organic compounds known as kavalactones. These are lactones, which is structurally characterized by a benzene ring and a pyranone moiety, linked to each other to form a 4-methoxy-6-(2-phenylethyl)-2H-pyran-2-one skeleton. 5,6-Dihydroyangonin has been detected, but not quantified in, beverages. This could make 5,6-dihydroyangonin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 5,6-Dihydroyangonin.

Structure

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

HMDB0033015
     RDKit          3D
5,6-Dihydroyangonin
 35 36  0  0  0  0  0  0  0  0999 V2000
   -5.2192    1.9041    0.7095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2665    0.4988    1.0044 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3198   -0.3313    0.3252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7450   -1.1872   -0.5710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8335   -2.0466   -1.2864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2186   -2.8731   -2.1460 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4667   -1.9331   -0.9896 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0335   -0.6470   -0.4904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6093   -0.8222   -0.1130 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3285    0.0627   -0.3708 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7336   -0.0699   -0.0188 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5970    0.9449   -0.3574 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9363    0.8828   -0.0544 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4877   -0.2006    0.6056 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8382   -0.2570    0.9079 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6814    0.8037    0.5420 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6147   -1.2124    0.9407 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2523   -1.1583    0.6372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8895   -0.2092    0.6470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3996    2.0884   -0.3662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1701    2.2641    0.9077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8778    2.4724    1.3645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8348   -1.2211   -0.7544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1810    0.0537   -1.3340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3158   -1.7240    0.4029 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0083    0.9596   -0.8895 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2113    1.8277   -0.8824 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5916    1.6974   -0.3339 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5414    1.1036   -0.5200 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7506    0.5445    0.6488 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4857    1.6878    1.1945 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0348   -2.0766    1.4633 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6115   -1.9755    0.9209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6799    0.8730    0.8313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6442   -0.7243    1.6036 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
  5  7  1  0
  7  8  1  0
  8  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
 15 16  1  0
 14 17  1  0
 17 18  2  0
  8 19  1  0
 19  3  1  0
 18 11  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  8 24  1  0
  9 25  1  0
 10 26  1  0
 12 27  1  0
 13 28  1  0
 16 29  1  0
 16 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 05061306512D          

 19 20  0  0  0  0            999 V2000
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -6.6000    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
  8  5  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
 13  9  1  0  0  0  0
 14  9  1  0  0  0  0
 14 10  2  0  0  0  0
 15 10  1  0  0  0  0
 16 15  2  0  0  0  0
 17  1  1  0  0  0  0
 17 12  1  0  0  0  0
 18  2  1  0  0  0  0
 18 14  1  0  0  0  0
 19 13  1  0  0  0  0
 19 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033015

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C15H16O4/c1-17-12-6-3-11(4-7-12)5-8-13-9-14(18-2)10-15(16)19-13/h3-8,10,13H,9H2,1-2H3/b8-5+

> <INCHI_KEY>
AYXCIWVJOBQVFH-VMPITWQZSA-N

> <FORMULA>
C15H16O4

> <MOLECULAR_WEIGHT>
260.2851

> <EXACT_MASS>
260.104859

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
27.993255308902356

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-methoxy-6-[(E)-2-(4-methoxyphenyl)ethenyl]-5,6-dihydro-2H-pyran-2-one

> <ALOGPS_LOGP>
2.80

> <JCHEM_LOGP>
2.2750404129999997

> <ALOGPS_LOGS>
-4.04

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.544395708313335

> <JCHEM_PKA_STRONGEST_BASIC>
-4.504263183806999

> <JCHEM_POLAR_SURFACE_AREA>
44.760000000000005

> <JCHEM_REFRACTIVITY>
73.82090000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.38e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-methoxy-6-[(E)-2-(4-methoxyphenyl)ethenyl]-5,6-dihydropyran-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0033015
     RDKit          3D
5,6-Dihydroyangonin
 35 36  0  0  0  0  0  0  0  0999 V2000
   -5.2192    1.9041    0.7095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2665    0.4988    1.0044 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3198   -0.3313    0.3252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7450   -1.1872   -0.5710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8335   -2.0466   -1.2864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2186   -2.8731   -2.1460 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4667   -1.9331   -0.9896 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0335   -0.6470   -0.4904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6093   -0.8222   -0.1130 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3285    0.0627   -0.3708 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7336   -0.0699   -0.0188 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5970    0.9449   -0.3574 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9363    0.8828   -0.0544 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4877   -0.2006    0.6056 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8382   -0.2570    0.9079 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6814    0.8037    0.5420 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6147   -1.2124    0.9407 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2523   -1.1583    0.6372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8895   -0.2092    0.6470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3996    2.0884   -0.3662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1701    2.2641    0.9077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8778    2.4724    1.3645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8348   -1.2211   -0.7544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1810    0.0537   -1.3340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3158   -1.7240    0.4029 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0083    0.9596   -0.8895 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2113    1.8277   -0.8824 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5916    1.6974   -0.3339 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5414    1.1036   -0.5200 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7506    0.5445    0.6488 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4857    1.6878    1.1945 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0348   -2.0766    1.4633 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6115   -1.9755    0.9209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6799    0.8730    0.8313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6442   -0.7243    1.6036 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
  5  7  1  0
  7  8  1  0
  8  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
 15 16  1  0
 14 17  1  0
 17 18  2  0
  8 19  1  0
 19  3  1  0
 18 11  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  8 24  1  0
  9 25  1  0
 10 26  1  0
 12 27  1  0
 13 28  1  0
 16 29  1  0
 16 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       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.002 -13.860   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335 -12.320   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001 -14.630   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335 -13.860   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667 -13.860   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       1.334 -14.630   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       6.668 -14.630   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       2.667 -12.320   0.000  0.00  0.00           O+0
CONECT    1   17                                                            
CONECT    2   18                                                            
CONECT    3    6   11                                                       
CONECT    4    7   11                                                       
CONECT    5    8   11                                                       
CONECT    6    3   12                                                       
CONECT    7    4   12                                                       
CONECT    8    5   13                                                       
CONECT    9   13   14                                                       
CONECT   10   14   15                                                       
CONECT   11    3    4    5                                                  
CONECT   12    6    7   17                                                  
CONECT   13    8    9   19                                                  
CONECT   14    9   10   18                                                  
CONECT   15   10   16   19                                                  
CONECT   16   15                                                            
CONECT   17    1   12                                                       
CONECT   18    2   14                                                       
CONECT   19   13   15                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

COMPND    HMDB0033015
HETATM    1  C1  UNL     1      -5.219   1.904   0.710  1.00  0.00           C  
HETATM    2  O1  UNL     1      -5.267   0.499   1.004  1.00  0.00           O  
HETATM    3  C2  UNL     1      -4.320  -0.331   0.325  1.00  0.00           C  
HETATM    4  C3  UNL     1      -4.745  -1.187  -0.571  1.00  0.00           C  
HETATM    5  C4  UNL     1      -3.833  -2.047  -1.286  1.00  0.00           C  
HETATM    6  O2  UNL     1      -4.219  -2.873  -2.146  1.00  0.00           O  
HETATM    7  O3  UNL     1      -2.467  -1.933  -0.990  1.00  0.00           O  
HETATM    8  C5  UNL     1      -2.034  -0.647  -0.490  1.00  0.00           C  
HETATM    9  C6  UNL     1      -0.609  -0.822  -0.113  1.00  0.00           C  
HETATM   10  C7  UNL     1       0.328   0.063  -0.371  1.00  0.00           C  
HETATM   11  C8  UNL     1       1.734  -0.070  -0.019  1.00  0.00           C  
HETATM   12  C9  UNL     1       2.597   0.945  -0.357  1.00  0.00           C  
HETATM   13  C10 UNL     1       3.936   0.883  -0.054  1.00  0.00           C  
HETATM   14  C11 UNL     1       4.488  -0.201   0.606  1.00  0.00           C  
HETATM   15  O4  UNL     1       5.838  -0.257   0.908  1.00  0.00           O  
HETATM   16  C12 UNL     1       6.681   0.804   0.542  1.00  0.00           C  
HETATM   17  C13 UNL     1       3.615  -1.212   0.941  1.00  0.00           C  
HETATM   18  C14 UNL     1       2.252  -1.158   0.637  1.00  0.00           C  
HETATM   19  C15 UNL     1      -2.889  -0.209   0.647  1.00  0.00           C  
HETATM   20  H1  UNL     1      -5.400   2.088  -0.366  1.00  0.00           H  
HETATM   21  H2  UNL     1      -4.170   2.264   0.908  1.00  0.00           H  
HETATM   22  H3  UNL     1      -5.878   2.472   1.365  1.00  0.00           H  
HETATM   23  H4  UNL     1      -5.835  -1.221  -0.754  1.00  0.00           H  
HETATM   24  H5  UNL     1      -2.181   0.054  -1.334  1.00  0.00           H  
HETATM   25  H6  UNL     1      -0.316  -1.724   0.403  1.00  0.00           H  
HETATM   26  H7  UNL     1       0.008   0.960  -0.890  1.00  0.00           H  
HETATM   27  H8  UNL     1       2.211   1.828  -0.882  1.00  0.00           H  
HETATM   28  H9  UNL     1       4.592   1.697  -0.334  1.00  0.00           H  
HETATM   29  H10 UNL     1       6.541   1.104  -0.520  1.00  0.00           H  
HETATM   30  H11 UNL     1       7.751   0.545   0.649  1.00  0.00           H  
HETATM   31  H12 UNL     1       6.486   1.688   1.195  1.00  0.00           H  
HETATM   32  H13 UNL     1       4.035  -2.077   1.463  1.00  0.00           H  
HETATM   33  H14 UNL     1       1.611  -1.976   0.921  1.00  0.00           H  
HETATM   34  H15 UNL     1      -2.680   0.873   0.831  1.00  0.00           H  
HETATM   35  H16 UNL     1      -2.644  -0.724   1.604  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3
CONECT    3    4    4   19
CONECT    4    5   23
CONECT    5    6    6    7
CONECT    7    8
CONECT    8    9   19   24
CONECT    9   10   10   25
CONECT   10   11   26
CONECT   11   12   12   18
CONECT   12   13   27
CONECT   13   14   14   28
CONECT   14   15   17
CONECT   15   16
CONECT   16   29   30   31
CONECT   17   18   18   32
CONECT   18   33
CONECT   19   34   35
END

HMDB0033015
     RDKit          3D
5,6-Dihydroyangonin
 35 36  0  0  0  0  0  0  0  0999 V2000
   -5.2192    1.9041    0.7095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2665    0.4988    1.0044 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3198   -0.3313    0.3252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7450   -1.1872   -0.5710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8335   -2.0466   -1.2864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2186   -2.8731   -2.1460 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4667   -1.9331   -0.9896 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0335   -0.6470   -0.4904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6093   -0.8222   -0.1130 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3285    0.0627   -0.3708 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7336   -0.0699   -0.0188 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5970    0.9449   -0.3574 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9363    0.8828   -0.0544 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4877   -0.2006    0.6056 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8382   -0.2570    0.9079 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6814    0.8037    0.5420 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6147   -1.2124    0.9407 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2523   -1.1583    0.6372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8895   -0.2092    0.6470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3996    2.0884   -0.3662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1701    2.2641    0.9077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8778    2.4724    1.3645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8348   -1.2211   -0.7544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1810    0.0537   -1.3340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3158   -1.7240    0.4029 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0083    0.9596   -0.8895 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2113    1.8277   -0.8824 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5916    1.6974   -0.3339 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5414    1.1036   -0.5200 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7506    0.5445    0.6488 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4857    1.6878    1.1945 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0348   -2.0766    1.4633 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6115   -1.9755    0.9209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6799    0.8730    0.8313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6442   -0.7243    1.6036 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
  5  7  1  0
  7  8  1  0
  8  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
 15 16  1  0
 14 17  1  0
 17 18  2  0
  8 19  1  0
 19  3  1  0
 18 11  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  8 24  1  0
  9 25  1  0
 10 26  1  0
 12 27  1  0
 13 28  1  0
 16 29  1  0
 16 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

Not Available

Chemical Formula

C₁₅H₁₆O₄

Average Molecular Weight

260.2851

Monoisotopic Molecular Weight

260.104859

IUPAC Name

4-methoxy-6-[(E)-2-(4-methoxyphenyl)ethenyl]-5,6-dihydro-2H-pyran-2-one

Traditional Name

4-methoxy-6-[(E)-2-(4-methoxyphenyl)ethenyl]-5,6-dihydropyran-2-one

CAS Registry Number

3328-60-7

SMILES

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

InChI Identifier

InChI=1S/C15H16O4/c1-17-12-6-3-11(4-7-12)5-8-13-9-14(18-2)10-15(16)19-13/h3-8,10,13H,9H2,1-2H3/b8-5+

InChI Key

AYXCIWVJOBQVFH-VMPITWQZSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as kavalactones. These are lactones, which is structurally characterized by a benzene ring and a pyranone moiety, linked to each other to form a 4-methoxy-6-(2-phenylethyl)-2H-pyran-2-one skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Kavalactones

Sub Class

Not Available

Direct Parent

Kavalactones

Alternative Parents

Substituents

Kavalactone
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Styrene
Alkyl aryl ether
Dihydropyranone
Monocyclic benzene moiety
Benzenoid
Pyran
Vinylogous ester
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Lactone
Carboxylic acid ester
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Ether
Oxacycle
Carboxylic acid derivative
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0033015)
Cell membrane (HMDB: HMDB0033015)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033015)

Source

Exogenous

Exogenous (HMDB: HMDB0033015)

Food

Food (HMDB: HMDB0033015)

Beverage

Beverages (FooDB: FOOD00870)

Endogenous

Plant

Plant (HMDB: HMDB0033015)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0033015)

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	0.024 g/L	ALOGPS
logP	2.8	ALOGPS
logP	2.28	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	16.54	ChemAxon
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	44.76 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	73.82 m³·mol⁻¹	ChemAxon
Polarizability	27.99 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
DarkChem	[M+H]+	166.991	31661259
DarkChem	[M-H]-	165.539	31661259
DeepCCS	[M+H]+	162.731	30932474
DeepCCS	[M-H]-	160.362	30932474
DeepCCS	[M-2H]-	193.248	30932474
DeepCCS	[M+Na]+	168.813	30932474
AllCCS	[M+H]+	162.0	32859911
AllCCS	[M+H-H2O]+	158.0	32859911
AllCCS	[M+NH4]+	165.6	32859911
AllCCS	[M+Na]+	166.7	32859911
AllCCS	[M-H]-	164.0	32859911
AllCCS	[M+Na-2H]-	164.0	32859911
AllCCS	[M+HCOO]-	164.1	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.	8.21 minutes	32390414
Predicted by Siyang on May 30, 2022	14.0236 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.89 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2384.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	360.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	176.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	212.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	100.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	556.8 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	537.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	129.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1332.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	477.8 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	1274.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	316.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	414.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	420.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	351.8 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	11.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5,6-Dihydroyangonin	COC1=CC(=O)OC(C1)\C=C\C1=CC=C(OC)C=C1	3440.7	Standard polar	33892256
5,6-Dihydroyangonin	COC1=CC(=O)OC(C1)\C=C\C1=CC=C(OC)C=C1	2296.2	Standard non polar	33892256
5,6-Dihydroyangonin	COC1=CC(=O)OC(C1)\C=C\C1=CC=C(OC)C=C1	2543.8	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 - 5,6-Dihydroyangonin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0avj-7690000000-4f31aed096680f17f0f9	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5,6-Dihydroyangonin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-Dihydroyangonin 10V, Positive-QTOF	splash10-03di-0290000000-e9b6faf18e44f7a7ba19	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-Dihydroyangonin 20V, Positive-QTOF	splash10-0bt9-2950000000-992a744a02842e1443db	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-Dihydroyangonin 40V, Positive-QTOF	splash10-0pb9-3900000000-62061a7d6632180af60c	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-Dihydroyangonin 10V, Negative-QTOF	splash10-0a4i-0190000000-dce7120862c5af83c145	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-Dihydroyangonin 20V, Negative-QTOF	splash10-052f-8290000000-c7feee5b7fd13c95eac7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-Dihydroyangonin 40V, Negative-QTOF	splash10-052f-9710000000-a8180c57fc4e720e1bfa	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-Dihydroyangonin 10V, Negative-QTOF	splash10-0a4i-0090000000-3cd3c62664dcb4e206a6	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-Dihydroyangonin 20V, Negative-QTOF	splash10-05o0-2950000000-dc14ca5ba3dc0cbd7fd2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-Dihydroyangonin 40V, Negative-QTOF	splash10-014i-2900000000-b4e43abe1873fe0b9d4c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-Dihydroyangonin 10V, Positive-QTOF	splash10-03di-0090000000-a50a62b73165b6963454	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-Dihydroyangonin 20V, Positive-QTOF	splash10-0002-1920000000-509469f7e6cba3967a39	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-Dihydroyangonin 40V, Positive-QTOF	splash10-004l-8900000000-266c6fd207f31b7513d4	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

FDB011007

KNApSAcK ID

Not Available

Chemspider ID

9797803

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11623055

PDB ID

Not Available

ChEBI ID

174416

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for 5,6-Dihydroyangonin (HMDB0033015)

MOL for HMDB0033015 (5,6-Dihydroyangonin)

3D MOL for HMDB0033015 (5,6-Dihydroyangonin)

3D SDF for HMDB0033015 (5,6-Dihydroyangonin)

3D-SDF for HMDB0033015 (5,6-Dihydroyangonin)

PDB for HMDB0033015 (5,6-Dihydroyangonin)

3D PDB for HMDB0033015 (5,6-Dihydroyangonin)

SMILES for HMDB0033015 (5,6-Dihydroyangonin)

INCHI for HMDB0033015 (5,6-Dihydroyangonin)

Structure for HMDB0033015 (5,6-Dihydroyangonin)

3D Structure for HMDB0033015 (5,6-Dihydroyangonin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra