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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:56:22 UTC

Update Date

2022-03-07 02:54:00 UTC

HMDB ID

HMDB0034144

Secondary Accession Numbers

HMDB34144

Metabolite Identification

Common Name

Yangonin

Description

Yangonin 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. Yangonin has been detected, but not quantified in, beverages. This could make yangonin a potential biomarker for the consumption of these foods. Yangonin is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on Yangonin.

Structure

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

HMDB0034144
     RDKit          3D
Yangonin
 33 34  0  0  0  0  0  0  0  0999 V2000
    6.5042    0.7795   -0.7820 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9777    0.0478    0.2940 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6056   -0.0859    0.4129 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0161   -0.7916    1.4457 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6560   -0.9179    1.5539 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7968   -0.3424    0.6300 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3701   -0.4717    0.7389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4754    0.0553   -0.1107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9278   -0.1475    0.1079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8557    0.3941   -0.7688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2017    0.2038   -0.5626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1463    0.7328   -1.4213 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5359    0.5490   -1.2273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5762   -0.5369    0.5362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6210   -1.0713    1.4036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9224   -1.7515    2.4152 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3609   -0.8402    1.1304 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3582    0.3606   -0.4004 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7497    0.4798   -0.4960 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5857    0.9577   -0.6964 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9840    1.7816   -0.7767 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2582    0.3261   -1.7670 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6457   -1.2581    2.1906 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1937   -1.4767    2.3722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0373   -1.0374    1.5707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1861    0.6323   -0.9668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4846    0.9730   -1.6228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7778    0.6536   -0.1428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1449    1.1912   -1.8647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7382   -0.5293   -1.4925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6101   -0.7394    0.7797 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7421    0.8354   -1.1570 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1584    1.0444   -1.3263 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  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
  8 26  1  0
 10 27  1  0
 13 28  1  0
 13 29  1  0
 13 30  1  0
 14 31  1  0
 18 32  1  0
 19 33  1  0
M  END

  Mrv0541 05061307362D          

 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  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>
HMDB0034144

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C15H14O4/c1-17-12-6-3-11(4-7-12)5-8-13-9-14(18-2)10-15(16)19-13/h3-10H,1-2H3/b8-5+

> <INCHI_KEY>
XLHIYUYCSMZCCC-VMPITWQZSA-N

> <FORMULA>
C15H14O4

> <MOLECULAR_WEIGHT>
258.2693

> <EXACT_MASS>
258.089208936

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
27.58398527920847

> <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]-2H-pyran-2-one

> <ALOGPS_LOGP>
3.00

> <JCHEM_LOGP>
2.4818186093333336

> <ALOGPS_LOGS>
-4.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.5242215546000075

> <JCHEM_POLAR_SURFACE_AREA>
44.760000000000005

> <JCHEM_REFRACTIVITY>
75.2039

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.30e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
yangonin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0034144
     RDKit          3D
Yangonin
 33 34  0  0  0  0  0  0  0  0999 V2000
    6.5042    0.7795   -0.7820 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9777    0.0478    0.2940 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6056   -0.0859    0.4129 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0161   -0.7916    1.4457 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6560   -0.9179    1.5539 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7968   -0.3424    0.6300 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3701   -0.4717    0.7389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4754    0.0553   -0.1107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9278   -0.1475    0.1079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8557    0.3941   -0.7688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2017    0.2038   -0.5626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1463    0.7328   -1.4213 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5359    0.5490   -1.2273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5762   -0.5369    0.5362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6210   -1.0713    1.4036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9224   -1.7515    2.4152 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3609   -0.8402    1.1304 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3582    0.3606   -0.4004 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7497    0.4798   -0.4960 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5857    0.9577   -0.6964 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9840    1.7816   -0.7767 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2582    0.3261   -1.7670 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6457   -1.2581    2.1906 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1937   -1.4767    2.3722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0373   -1.0374    1.5707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1861    0.6323   -0.9668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4846    0.9730   -1.6228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7778    0.6536   -0.1428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1449    1.1912   -1.8647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7382   -0.5293   -1.4925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6101   -0.7394    0.7797 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7421    0.8354   -1.1570 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1584    1.0444   -1.3263 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  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
  8 26  1  0
 10 27  1  0
 13 28  1  0
 13 29  1  0
 13 30  1  0
 14 31  1  0
 18 32  1  0
 19 33  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    HMDB0034144
HETATM    1  C1  UNL     1       6.504   0.779  -0.782  1.00  0.00           C  
HETATM    2  O1  UNL     1       5.978   0.048   0.294  1.00  0.00           O  
HETATM    3  C2  UNL     1       4.606  -0.086   0.413  1.00  0.00           C  
HETATM    4  C3  UNL     1       4.016  -0.792   1.446  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.656  -0.918   1.554  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.797  -0.342   0.630  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.370  -0.472   0.739  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.475   0.055  -0.111  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.928  -0.148   0.108  1.00  0.00           C  
HETATM   10  C9  UNL     1      -2.856   0.394  -0.769  1.00  0.00           C  
HETATM   11  C10 UNL     1      -4.202   0.204  -0.563  1.00  0.00           C  
HETATM   12  O2  UNL     1      -5.146   0.733  -1.421  1.00  0.00           O  
HETATM   13  C11 UNL     1      -6.536   0.549  -1.227  1.00  0.00           C  
HETATM   14  C12 UNL     1      -4.576  -0.537   0.536  1.00  0.00           C  
HETATM   15  C13 UNL     1      -3.621  -1.071   1.404  1.00  0.00           C  
HETATM   16  O3  UNL     1      -3.922  -1.751   2.415  1.00  0.00           O  
HETATM   17  O4  UNL     1      -2.361  -0.840   1.130  1.00  0.00           O  
HETATM   18  C14 UNL     1       2.358   0.361  -0.400  1.00  0.00           C  
HETATM   19  C15 UNL     1       3.750   0.480  -0.496  1.00  0.00           C  
HETATM   20  H1  UNL     1       7.586   0.958  -0.696  1.00  0.00           H  
HETATM   21  H2  UNL     1       5.984   1.782  -0.777  1.00  0.00           H  
HETATM   22  H3  UNL     1       6.258   0.326  -1.767  1.00  0.00           H  
HETATM   23  H4  UNL     1       4.646  -1.258   2.191  1.00  0.00           H  
HETATM   24  H5  UNL     1       2.194  -1.477   2.372  1.00  0.00           H  
HETATM   25  H6  UNL     1      -0.037  -1.037   1.571  1.00  0.00           H  
HETATM   26  H7  UNL     1      -0.186   0.632  -0.967  1.00  0.00           H  
HETATM   27  H8  UNL     1      -2.485   0.973  -1.623  1.00  0.00           H  
HETATM   28  H9  UNL     1      -6.778   0.654  -0.143  1.00  0.00           H  
HETATM   29  H10 UNL     1      -7.145   1.191  -1.865  1.00  0.00           H  
HETATM   30  H11 UNL     1      -6.738  -0.529  -1.492  1.00  0.00           H  
HETATM   31  H12 UNL     1      -5.610  -0.739   0.780  1.00  0.00           H  
HETATM   32  H13 UNL     1       1.742   0.835  -1.157  1.00  0.00           H  
HETATM   33  H14 UNL     1       4.158   1.044  -1.326  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    8   25
CONECT    8    9   26
CONECT    9   10   10   17
CONECT   10   11   27
CONECT   11   12   14   14
CONECT   12   13
CONECT   13   28   29   30
CONECT   14   15   31
CONECT   15   16   16   17
CONECT   18   19   19   32
CONECT   19   33
END

HMDB0034144
     RDKit          3D
Yangonin
 33 34  0  0  0  0  0  0  0  0999 V2000
    6.5042    0.7795   -0.7820 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9777    0.0478    0.2940 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6056   -0.0859    0.4129 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0161   -0.7916    1.4457 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6560   -0.9179    1.5539 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7968   -0.3424    0.6300 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3701   -0.4717    0.7389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4754    0.0553   -0.1107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9278   -0.1475    0.1079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8557    0.3941   -0.7688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2017    0.2038   -0.5626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1463    0.7328   -1.4213 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5359    0.5490   -1.2273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5762   -0.5369    0.5362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6210   -1.0713    1.4036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9224   -1.7515    2.4152 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3609   -0.8402    1.1304 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3582    0.3606   -0.4004 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7497    0.4798   -0.4960 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5857    0.9577   -0.6964 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9840    1.7816   -0.7767 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2582    0.3261   -1.7670 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6457   -1.2581    2.1906 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1937   -1.4767    2.3722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0373   -1.0374    1.5707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1861    0.6323   -0.9668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4846    0.9730   -1.6228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7778    0.6536   -0.1428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1449    1.1912   -1.8647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7382   -0.5293   -1.4925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6101   -0.7394    0.7797 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7421    0.8354   -1.1570 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1584    1.0444   -1.3263 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  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
  8 26  1  0
 10 27  1  0
 13 28  1  0
 13 29  1  0
 13 30  1  0
 14 31  1  0
 18 32  1  0
 19 33  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-Methoxy-6-[2-(4-methoxyphenyl)ethenyl]-2H-pyran-2-one	Kegg
4-Methoxy-6-(p-methoxystyryl)-2H-pyran-2-one	MeSH
4-Methoxy-6-(4-methoxystyryl)-a-pyrone	HMDB
4-Methoxy-6-(beta-(P-anisyl)vinyl)-alpha-pyrone	HMDB
4-Methoxy-6-[(e)-2-(4-methoxyphenyl)vinyl]-2H-pyran-2-one	HMDB
4-Methoxy-6-[2-(4-methoxyphenyl)ethenyl]-2H-pyran-2-one, 9ci	HMDB

Chemical Formula

C₁₅H₁₄O₄

Average Molecular Weight

258.2693

Monoisotopic Molecular Weight

258.089208936

IUPAC Name

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

Traditional Name

yangonin

CAS Registry Number

500-62-9

SMILES

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

InChI Identifier

InChI=1S/C15H14O4/c1-17-12-6-3-11(4-7-12)5-8-13-9-14(18-2)10-15(16)19-13/h3-10H,1-2H3/b8-5+

InChI Key

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

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

aromatic ether (CHEBI:10089 )
2-pyranones (CHEBI:10089 )
alpha-Pyrones (C09980 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0034144)
Cell membrane (HMDB: HMDB0034144)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0034144)

Source

Exogenous

Exogenous (HMDB: HMDB0034144)

Food

Food (HMDB: HMDB0034144)

Beverage

Beverages (FooDB: FOOD00870)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0034144)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	153 - 154 °C	Not Available
Boiling Point	487.60 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	816.4 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.750 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.013 g/L	ALOGPS
logP	3	ALOGPS
logP	2.48	ChemAxon
logS	-4.3	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	4	ChemAxon
Refractivity	75.2 m³·mol⁻¹	ChemAxon
Polarizability	27.58 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]+	163.167	31661259
DarkChem	[M-H]-	167.132	31661259
DeepCCS	[M+H]+	164.332	30932474
DeepCCS	[M-H]-	161.975	30932474
DeepCCS	[M-2H]-	194.861	30932474
DeepCCS	[M+Na]+	170.426	30932474
AllCCS	[M+H]+	158.8	32859911
AllCCS	[M+H-H2O]+	154.7	32859911
AllCCS	[M+NH4]+	162.6	32859911
AllCCS	[M+Na]+	163.7	32859911
AllCCS	[M-H]-	161.0	32859911
AllCCS	[M+Na-2H]-	160.7	32859911
AllCCS	[M+HCOO]-	160.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Yangonin	COC1=CC=C(\C=C\C2=CC(OC)=CC(=O)O2)C=C1	3714.4	Standard polar	33892256
Yangonin	COC1=CC=C(\C=C\C2=CC(OC)=CC(=O)O2)C=C1	2419.7	Standard non polar	33892256
Yangonin	COC1=CC=C(\C=C\C2=CC(OC)=CC(=O)O2)C=C1	2672.0	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 - Yangonin GC-MS (Non-derivatized) - 70eV, Positive	splash10-052f-1390000000-b5bbf1f136609500165b	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Yangonin 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 - Yangonin 10V, Positive-QTOF	splash10-0a4i-0090000000-0064fe61f04f340cfc41	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Yangonin 20V, Positive-QTOF	splash10-0a4i-0390000000-02f5c4ac24041bff5138	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Yangonin 40V, Positive-QTOF	splash10-0a4i-2950000000-c356024333a2fa73d48f	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Yangonin 10V, Negative-QTOF	splash10-0a4i-0090000000-c80037a5499d4ee96e80	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Yangonin 20V, Negative-QTOF	splash10-0006-8190000000-25a283ee23eb1eaea784	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Yangonin 40V, Negative-QTOF	splash10-052f-9810000000-a91c0a22e3459308740c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Yangonin 10V, Negative-QTOF	splash10-0a4i-0090000000-3565cef92b3fab56cc27	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Yangonin 20V, Negative-QTOF	splash10-053r-0950000000-41905c71b0906a928933	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Yangonin 40V, Negative-QTOF	splash10-066u-5920000000-2a14c40b8398bc1421b2	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Yangonin 10V, Positive-QTOF	splash10-0a4i-0090000000-1b6066ae6cfd0e8e6c60	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Yangonin 20V, Positive-QTOF	splash10-0a4i-0590000000-b66b397b084847302e29	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Yangonin 40V, Positive-QTOF	splash10-004r-8920000000-b4d4c5a43694ac95910a	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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Yangonin

METLIN ID

Not Available

PubChem Compound

5281575

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1416591

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 Yangonin (HMDB0034144)

MOL for HMDB0034144 (Yangonin)

3D MOL for HMDB0034144 (Yangonin)

3D SDF for HMDB0034144 (Yangonin)

3D-SDF for HMDB0034144 (Yangonin)

PDB for HMDB0034144 (Yangonin)

3D PDB for HMDB0034144 (Yangonin)

SMILES for HMDB0034144 (Yangonin)

INCHI for HMDB0034144 (Yangonin)

Structure for HMDB0034144 (Yangonin)

3D Structure for HMDB0034144 (Yangonin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra