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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:53:16 UTC

Update Date

2022-03-07 02:53:33 UTC

HMDB ID

HMDB0033016

Secondary Accession Numbers

HMDB33016

Metabolite Identification

Common Name

7,8-Dihydroyangonin

Description

7,8-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. 7,8-Dihydroyangonin has been detected, but not quantified in, beverages. This could make 7,8-dihydroyangonin a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on 7,8-Dihydroyangonin.

Structure

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

HMDB0033016
     RDKit          3D
7,8-Dihydroyangonin
 35 36  0  0  0  0  0  0  0  0999 V2000
    6.5188    0.5638    0.7797 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8362   -0.0302   -0.3034 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4578    0.0007   -0.3541 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7610   -0.5698   -1.3976 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3867   -0.5024   -1.3847 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6556    0.1030   -0.3889 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1998    0.1844   -0.3576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4729   -0.9556    0.3331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9452   -0.8447    0.3483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6197    0.2134   -0.2231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9939    0.1938   -0.1382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6786    1.2522   -0.7092 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0770    1.3166   -0.6712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6553   -0.8431    0.4927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9008   -1.8640    1.0384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4986   -2.8221    1.6206 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5988   -1.8321    0.9503 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3705    0.6728    0.6546 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7659    0.6171    0.6636 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0818    0.0985    1.7119 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6026    0.3699    0.7286 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2536    1.6273    0.8248 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3256   -1.0484   -2.1856 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8580   -0.9457   -2.1944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0886    1.1235    0.1597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1509    0.3162   -1.4155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1421   -0.9384    1.3972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2211   -1.9442   -0.0587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0543    0.9963   -0.7029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4862    1.0191    0.2971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3783    2.3821   -0.8772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4940    0.7088   -1.5202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7429   -0.8625    0.5621 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8409    1.1635    1.4664 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2844    1.0802    1.5069 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  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 11 14  2  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
  6 18  1  0
 18 19  2  0
 19  3  1  0
 17  9  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  5 24  1  0
  7 25  1  0
  7 26  1  0
  8 27  1  0
  8 28  1  0
 10 29  1  0
 13 30  1  0
 13 31  1  0
 13 32  1  0
 14 33  1  0
 18 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  1  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  2  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>
HMDB0033016

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC=C(CCC2=CC(OC)=CC(=O)O2)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/h3-4,6-7,9-10H,5,8H2,1-2H3

> <INCHI_KEY>
CZCOHVXNUPVUBC-UHFFFAOYSA-N

> <FORMULA>
C15H16O4

> <MOLECULAR_WEIGHT>
260.2851

> <EXACT_MASS>
260.104859

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
27.85656829806559

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-methoxy-6-[2-(4-methoxyphenyl)ethyl]-2H-pyran-2-one

> <ALOGPS_LOGP>
3.28

> <JCHEM_LOGP>
2.6051328059999994

> <ALOGPS_LOGS>
-4.03

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.520418071418643

> <JCHEM_POLAR_SURFACE_AREA>
44.760000000000005

> <JCHEM_REFRACTIVITY>
74.24130000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.45e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-methoxy-6-[2-(4-methoxyphenyl)ethyl]pyran-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0033016
     RDKit          3D
7,8-Dihydroyangonin
 35 36  0  0  0  0  0  0  0  0999 V2000
    6.5188    0.5638    0.7797 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8362   -0.0302   -0.3034 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4578    0.0007   -0.3541 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7610   -0.5698   -1.3976 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3867   -0.5024   -1.3847 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6556    0.1030   -0.3889 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1998    0.1844   -0.3576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4729   -0.9556    0.3331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9452   -0.8447    0.3483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6197    0.2134   -0.2231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9939    0.1938   -0.1382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6786    1.2522   -0.7092 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0770    1.3166   -0.6712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6553   -0.8431    0.4927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9008   -1.8640    1.0384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4986   -2.8221    1.6206 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5988   -1.8321    0.9503 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3705    0.6728    0.6546 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7659    0.6171    0.6636 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0818    0.0985    1.7119 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6026    0.3699    0.7286 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2536    1.6273    0.8248 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3256   -1.0484   -2.1856 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8580   -0.9457   -2.1944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0886    1.1235    0.1597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1509    0.3162   -1.4155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1421   -0.9384    1.3972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2211   -1.9442   -0.0587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0543    0.9963   -0.7029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4862    1.0191    0.2971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3783    2.3821   -0.8772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4940    0.7088   -1.5202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7429   -0.8625    0.5621 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8409    1.1635    1.4664 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2844    1.0802    1.5069 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  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 11 14  2  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
  6 18  1  0
 18 19  2  0
 19  3  1  0
 17  9  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  5 24  1  0
  7 25  1  0
  7 26  1  0
  8 27  1  0
  8 28  1  0
 10 29  1  0
 13 30  1  0
 13 31  1  0
 13 32  1  0
 14 33  1  0
 18 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    HMDB0033016
HETATM    1  C1  UNL     1       6.519   0.564   0.780  1.00  0.00           C  
HETATM    2  O1  UNL     1       5.836  -0.030  -0.303  1.00  0.00           O  
HETATM    3  C2  UNL     1       4.458   0.001  -0.354  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.761  -0.570  -1.398  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.387  -0.502  -1.385  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.656   0.103  -0.389  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.200   0.184  -0.358  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.473  -0.956   0.333  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.945  -0.845   0.348  1.00  0.00           C  
HETATM   10  C9  UNL     1      -2.620   0.213  -0.223  1.00  0.00           C  
HETATM   11  C10 UNL     1      -3.994   0.194  -0.138  1.00  0.00           C  
HETATM   12  O2  UNL     1      -4.679   1.252  -0.709  1.00  0.00           O  
HETATM   13  C11 UNL     1      -6.077   1.317  -0.671  1.00  0.00           C  
HETATM   14  C12 UNL     1      -4.655  -0.843   0.493  1.00  0.00           C  
HETATM   15  C13 UNL     1      -3.901  -1.864   1.038  1.00  0.00           C  
HETATM   16  O3  UNL     1      -4.499  -2.822   1.621  1.00  0.00           O  
HETATM   17  O4  UNL     1      -2.599  -1.832   0.950  1.00  0.00           O  
HETATM   18  C14 UNL     1       2.370   0.673   0.655  1.00  0.00           C  
HETATM   19  C15 UNL     1       3.766   0.617   0.664  1.00  0.00           C  
HETATM   20  H1  UNL     1       6.082   0.098   1.712  1.00  0.00           H  
HETATM   21  H2  UNL     1       7.603   0.370   0.729  1.00  0.00           H  
HETATM   22  H3  UNL     1       6.254   1.627   0.825  1.00  0.00           H  
HETATM   23  H4  UNL     1       4.326  -1.048  -2.186  1.00  0.00           H  
HETATM   24  H5  UNL     1       1.858  -0.946  -2.194  1.00  0.00           H  
HETATM   25  H6  UNL     1      -0.089   1.124   0.160  1.00  0.00           H  
HETATM   26  H7  UNL     1      -0.151   0.316  -1.415  1.00  0.00           H  
HETATM   27  H8  UNL     1      -0.142  -0.938   1.397  1.00  0.00           H  
HETATM   28  H9  UNL     1      -0.221  -1.944  -0.059  1.00  0.00           H  
HETATM   29  H10 UNL     1      -2.054   0.996  -0.703  1.00  0.00           H  
HETATM   30  H11 UNL     1      -6.486   1.019   0.297  1.00  0.00           H  
HETATM   31  H12 UNL     1      -6.378   2.382  -0.877  1.00  0.00           H  
HETATM   32  H13 UNL     1      -6.494   0.709  -1.520  1.00  0.00           H  
HETATM   33  H14 UNL     1      -5.743  -0.862   0.562  1.00  0.00           H  
HETATM   34  H15 UNL     1       1.841   1.163   1.466  1.00  0.00           H  
HETATM   35  H16 UNL     1       4.284   1.080   1.507  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   24
CONECT    6    7   18
CONECT    7    8   25   26
CONECT    8    9   27   28
CONECT    9   10   10   17
CONECT   10   11   29
CONECT   11   12   14   14
CONECT   12   13
CONECT   13   30   31   32
CONECT   14   15   33
CONECT   15   16   16   17
CONECT   18   19   19   34
CONECT   19   35
END

HMDB0033016
     RDKit          3D
7,8-Dihydroyangonin
 35 36  0  0  0  0  0  0  0  0999 V2000
    6.5188    0.5638    0.7797 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8362   -0.0302   -0.3034 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4578    0.0007   -0.3541 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7610   -0.5698   -1.3976 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3867   -0.5024   -1.3847 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6556    0.1030   -0.3889 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1998    0.1844   -0.3576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4729   -0.9556    0.3331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9452   -0.8447    0.3483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6197    0.2134   -0.2231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9939    0.1938   -0.1382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6786    1.2522   -0.7092 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0770    1.3166   -0.6712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6553   -0.8431    0.4927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9008   -1.8640    1.0384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4986   -2.8221    1.6206 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5988   -1.8321    0.9503 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3705    0.6728    0.6546 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7659    0.6171    0.6636 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0818    0.0985    1.7119 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6026    0.3699    0.7286 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2536    1.6273    0.8248 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3256   -1.0484   -2.1856 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8580   -0.9457   -2.1944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0886    1.1235    0.1597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1509    0.3162   -1.4155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1421   -0.9384    1.3972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2211   -1.9442   -0.0587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0543    0.9963   -0.7029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4862    1.0191    0.2971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3783    2.3821   -0.8772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4940    0.7088   -1.5202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7429   -0.8625    0.5621 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8409    1.1635    1.4664 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2844    1.0802    1.5069 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  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 11 14  2  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
  6 18  1  0
 18 19  2  0
 19  3  1  0
 17  9  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  5 24  1  0
  7 25  1  0
  7 26  1  0
  8 27  1  0
  8 28  1  0
 10 29  1  0
 13 30  1  0
 13 31  1  0
 13 32  1  0
 14 33  1  0
 18 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-[2-(4-methoxyphenyl)ethyl]-2H-pyran-2-one

Traditional Name

4-methoxy-6-[2-(4-methoxyphenyl)ethyl]pyran-2-one

CAS Registry Number

3155-52-0

SMILES

COC1=CC=C(CCC2=CC(OC)=CC(=O)O2)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/h3-4,6-7,9-10H,5,8H2,1-2H3

InChI Key

CZCOHVXNUPVUBC-UHFFFAOYSA-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
Phenol ether
Methoxybenzene
Alkyl aryl ether
Pyranone
Monocyclic benzene moiety
Pyran
Benzenoid
Heteroaromatic compound
Vinylogous ester
Lactone
Oxacycle
Ether
Organoheterocyclic compound
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0033016)

Cellular substructure

Membrane (HMDB: HMDB0033016)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033016)

Source

Exogenous

Food

Food (HMDB: HMDB0033016)

Beverage

Beverages (FooDB: FOOD00870)

Endogenous

Plant

Plant (HMDB: HMDB0033016)

Not Available

Nutrient (HMDB: HMDB0033016)

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	3.28	ALOGPS
logP	2.61	ChemAxon
logS	-4	ALOGPS
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	5	ChemAxon
Refractivity	74.24 m³·mol⁻¹	ChemAxon
Polarizability	27.86 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]+	162.915	31661259
DarkChem	[M-H]-	162.479	31661259
DeepCCS	[M+H]+	163.118	30932474
DeepCCS	[M-H]-	160.76	30932474
DeepCCS	[M-2H]-	193.656	30932474
DeepCCS	[M+Na]+	169.211	30932474
AllCCS	[M+H]+	160.2	32859911
AllCCS	[M+H-H2O]+	156.2	32859911
AllCCS	[M+NH4]+	163.9	32859911
AllCCS	[M+Na]+	165.0	32859911
AllCCS	[M-H]-	163.2	32859911
AllCCS	[M+Na-2H]-	163.0	32859911
AllCCS	[M+HCOO]-	162.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
7,8-Dihydroyangonin	COC1=CC=C(CCC2=CC(OC)=CC(=O)O2)C=C1	3291.8	Standard polar	33892256
7,8-Dihydroyangonin	COC1=CC=C(CCC2=CC(OC)=CC(=O)O2)C=C1	2334.1	Standard non polar	33892256
7,8-Dihydroyangonin	COC1=CC=C(CCC2=CC(OC)=CC(=O)O2)C=C1	2406.0	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 - 7,8-Dihydroyangonin GC-MS (Non-derivatized) - 70eV, Positive	splash10-00dm-4890000000-79129d823c5d3e69b3a4	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 7,8-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
Experimental LC-MS/MS	LC-MS/MS Spectrum - 7,8-Dihydroyangonin , positive-QTOF	splash10-00di-0900100000-71515f5c9fd356cfd984	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 7,8-Dihydroyangonin , positive-QTOF	splash10-00di-1900000000-d27f34780b80038ba2b3	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 7,8-Dihydroyangonin , positive-QTOF	splash10-00di-0910000000-01ba71ec94eae24549ac	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7,8-Dihydroyangonin 10V, Positive-QTOF	splash10-03di-0090000000-b04a23b366f187b2a2a1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7,8-Dihydroyangonin 20V, Positive-QTOF	splash10-03di-0390000000-0d2f36b67a35b7d92201	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7,8-Dihydroyangonin 40V, Positive-QTOF	splash10-0pb9-2940000000-d56a527e305249b19e83	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7,8-Dihydroyangonin 10V, Negative-QTOF	splash10-0a4i-0090000000-9e36f0b91482ae9302ee	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7,8-Dihydroyangonin 20V, Negative-QTOF	splash10-052f-9070000000-de906ad3faf227c04029	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7,8-Dihydroyangonin 40V, Negative-QTOF	splash10-052f-9810000000-666551ea654b933f2086	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7,8-Dihydroyangonin 10V, Positive-QTOF	splash10-03di-0190000000-8987b5811228c590fd21	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7,8-Dihydroyangonin 20V, Positive-QTOF	splash10-03kd-3970000000-345a4847e680a3f96de8	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7,8-Dihydroyangonin 40V, Positive-QTOF	splash10-004l-9310000000-c50a36e3944d1362ab43	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7,8-Dihydroyangonin 10V, Negative-QTOF	splash10-0a4i-0190000000-5ea7e350b6c321587b9c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7,8-Dihydroyangonin 20V, Negative-QTOF	splash10-000i-2910000000-3cba9b310d639cd4bff0	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7,8-Dihydroyangonin 40V, Negative-QTOF	splash10-0aou-3930000000-3007596737f44301b48c	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

FDB011008

KNApSAcK ID

Not Available

Chemspider ID

8168337

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9992755

PDB ID

Not Available

ChEBI ID

Not Available

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 7,8-Dihydroyangonin (HMDB0033016)

MOL for HMDB0033016 (7,8-Dihydroyangonin)

3D MOL for HMDB0033016 (7,8-Dihydroyangonin)

3D SDF for HMDB0033016 (7,8-Dihydroyangonin)

3D-SDF for HMDB0033016 (7,8-Dihydroyangonin)

PDB for HMDB0033016 (7,8-Dihydroyangonin)

3D PDB for HMDB0033016 (7,8-Dihydroyangonin)

SMILES for HMDB0033016 (7,8-Dihydroyangonin)

INCHI for HMDB0033016 (7,8-Dihydroyangonin)

Structure for HMDB0033016 (7,8-Dihydroyangonin)

3D Structure for HMDB0033016 (7,8-Dihydroyangonin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra