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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 19:00:53 UTC

Update Date

2022-03-07 02:54:01 UTC

HMDB ID

HMDB0034212

Secondary Accession Numbers

HMDB34212

Metabolite Identification

Common Name

(R)-Kawain

Description

(R)-Kawain 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 (R)-Kawain has been detected, but not quantified in, beverages. This could make (R)-kawain a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on (R)-Kawain.

Structure

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

HMDB0034212
     RDKit          3D
(R)-Kawain
 31 32  0  0  0  0  0  0  0  0999 V2000
   -5.1010    0.1763   -0.4265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9734    0.7698   -1.0423 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7183    0.7792   -0.4493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0317    1.8948   -0.4665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6914    1.9554    0.1459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0204    2.9975    0.1512 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2671    0.7528    0.7057 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6475   -0.4173   -0.0010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0753   -1.6283    0.5096 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1615   -1.8639    0.7238 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2442   -0.9585    0.4857 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4523   -1.1908    1.1800 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5847   -0.4479    1.0021 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6153    0.6013    0.1090 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4720    0.8619   -0.5855 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3106    0.0840   -0.3906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1927   -0.4328    0.1784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2479    0.7172    0.5457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9945   -0.9155   -0.2905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9988    0.3567   -1.0306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4668    2.7648   -0.9366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5378   -0.3026   -1.0718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7848   -2.4539    0.7437 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4599   -2.8881    1.1333 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4662   -1.9911    1.8798 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5056   -0.6467    1.5542 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5285    1.1726   -0.0093 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4465    1.6699   -1.2937 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4769    0.3233   -1.0135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3652   -0.3654    1.2837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6097   -1.3748   -0.2053 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  2  0
  8 17  1  0
 17  3  1  0
 16 11  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  4 21  1  0
  8 22  1  0
  9 23  1  0
 10 24  1  0
 12 25  1  0
 13 26  1  0
 14 27  1  0
 15 28  1  0
 16 29  1  0
 17 30  1  0
 17 31  1  0
M  END


  Mrv0541 05061307392D          

 17 18  0  0  0  0            999 V2000
    7.1447    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    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    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  2  0  0  0  0
  8  7  2  0  0  0  0
 11  5  2  0  0  0  0
 11  6  1  0  0  0  0
 11  7  1  0  0  0  0
 12  8  1  0  0  0  0
 12  9  1  0  0  0  0
 13  9  1  0  0  0  0
 13 10  2  0  0  0  0
 14 10  1  0  0  0  0
 15 14  2  0  0  0  0
 16  1  1  0  0  0  0
 16 13  1  0  0  0  0
 17 12  1  0  0  0  0
 17 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0034212

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C14H14O3/c1-16-13-9-12(17-14(15)10-13)8-7-11-5-3-2-4-6-11/h2-8,10,12H,9H2,1H3/b8-7-

> <INCHI_KEY>
XEAQIWGXBXCYFX-FPLPWBNLSA-N

> <FORMULA>
C14H14O3

> <MOLECULAR_WEIGHT>
230.2592

> <EXACT_MASS>
230.094294314

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
24.6086889773122

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-methoxy-6-[(Z)-2-phenylethenyl]-5,6-dihydro-2H-pyran-2-one

> <ALOGPS_LOGP>
2.96

> <JCHEM_LOGP>
2.4327116786666663

> <ALOGPS_LOGS>
-3.60

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.541493371180767

> <JCHEM_PKA_STRONGEST_BASIC>
-4.788416686866828

> <JCHEM_POLAR_SURFACE_AREA>
35.53

> <JCHEM_REFRACTIVITY>
67.35770000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.73e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-methoxy-6-[(Z)-2-phenylethenyl]-5,6-dihydropyran-2-one

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0034212
     RDKit          3D
(R)-Kawain
 31 32  0  0  0  0  0  0  0  0999 V2000
   -5.1010    0.1763   -0.4265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9734    0.7698   -1.0423 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7183    0.7792   -0.4493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0317    1.8948   -0.4665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6914    1.9554    0.1459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0204    2.9975    0.1512 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2671    0.7528    0.7057 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6475   -0.4173   -0.0010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0753   -1.6283    0.5096 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1615   -1.8639    0.7238 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2442   -0.9585    0.4857 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4523   -1.1908    1.1800 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5847   -0.4479    1.0021 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6153    0.6013    0.1090 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4720    0.8619   -0.5855 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3106    0.0840   -0.3906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1927   -0.4328    0.1784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2479    0.7172    0.5457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9945   -0.9155   -0.2905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9988    0.3567   -1.0306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4668    2.7648   -0.9366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5378   -0.3026   -1.0718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7848   -2.4539    0.7437 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4599   -2.8881    1.1333 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4662   -1.9911    1.8798 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5056   -0.6467    1.5542 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5285    1.1726   -0.0093 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4465    1.6699   -1.2937 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4769    0.3233   -1.0135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3652   -0.3654    1.2837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6097   -1.3748   -0.2053 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  2  0
  8 17  1  0
 17  3  1  0
 16 11  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  4 21  1  0
  8 22  1  0
  9 23  1  0
 10 24  1  0
 12 25  1  0
 13 26  1  0
 14 27  1  0
 15 28  1  0
 16 29  1  0
 17 30  1  0
 17 31  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   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       9.336  -2.310   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      12.003   2.310   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       8.002   0.000   0.000  0.00  0.00           O+0
CONECT    1   16                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3   11                                                       
CONECT    6    4   11                                                       
CONECT    7    8   11                                                       
CONECT    8    7   12                                                       
CONECT    9   12   13                                                       
CONECT   10   13   14                                                       
CONECT   11    5    6    7                                                  
CONECT   12    8    9   17                                                  
CONECT   13    9   10   16                                                  
CONECT   14   10   15   17                                                  
CONECT   15   14                                                            
CONECT   16    1   13                                                       
CONECT   17   12   14                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

COMPND    HMDB0034212
HETATM    1  C1  UNL     1      -5.101   0.176  -0.427  1.00  0.00           C  
HETATM    2  O1  UNL     1      -3.973   0.770  -1.042  1.00  0.00           O  
HETATM    3  C2  UNL     1      -2.718   0.779  -0.449  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.032   1.895  -0.466  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.691   1.955   0.146  1.00  0.00           C  
HETATM    6  O2  UNL     1      -0.020   2.997   0.151  1.00  0.00           O  
HETATM    7  O3  UNL     1      -0.267   0.753   0.706  1.00  0.00           O  
HETATM    8  C5  UNL     1      -0.648  -0.417  -0.001  1.00  0.00           C  
HETATM    9  C6  UNL     1      -0.075  -1.628   0.510  1.00  0.00           C  
HETATM   10  C7  UNL     1       1.162  -1.864   0.724  1.00  0.00           C  
HETATM   11  C8  UNL     1       2.244  -0.959   0.486  1.00  0.00           C  
HETATM   12  C9  UNL     1       3.452  -1.191   1.180  1.00  0.00           C  
HETATM   13  C10 UNL     1       4.585  -0.448   1.002  1.00  0.00           C  
HETATM   14  C11 UNL     1       4.615   0.601   0.109  1.00  0.00           C  
HETATM   15  C12 UNL     1       3.472   0.862  -0.585  1.00  0.00           C  
HETATM   16  C13 UNL     1       2.311   0.084  -0.391  1.00  0.00           C  
HETATM   17  C14 UNL     1      -2.193  -0.433   0.178  1.00  0.00           C  
HETATM   18  H1  UNL     1      -5.248   0.717   0.546  1.00  0.00           H  
HETATM   19  H2  UNL     1      -4.994  -0.915  -0.291  1.00  0.00           H  
HETATM   20  H3  UNL     1      -5.999   0.357  -1.031  1.00  0.00           H  
HETATM   21  H4  UNL     1      -2.467   2.765  -0.937  1.00  0.00           H  
HETATM   22  H5  UNL     1      -0.538  -0.303  -1.072  1.00  0.00           H  
HETATM   23  H6  UNL     1      -0.785  -2.454   0.744  1.00  0.00           H  
HETATM   24  H7  UNL     1       1.460  -2.888   1.133  1.00  0.00           H  
HETATM   25  H8  UNL     1       3.466  -1.991   1.880  1.00  0.00           H  
HETATM   26  H9  UNL     1       5.506  -0.647   1.554  1.00  0.00           H  
HETATM   27  H10 UNL     1       5.528   1.173  -0.009  1.00  0.00           H  
HETATM   28  H11 UNL     1       3.446   1.670  -1.294  1.00  0.00           H  
HETATM   29  H12 UNL     1       1.477   0.323  -1.014  1.00  0.00           H  
HETATM   30  H13 UNL     1      -2.365  -0.365   1.284  1.00  0.00           H  
HETATM   31  H14 UNL     1      -2.610  -1.375  -0.205  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3
CONECT    3    4    4   17
CONECT    4    5   21
CONECT    5    6    6    7
CONECT    7    8
CONECT    8    9   17   22
CONECT    9   10   10   23
CONECT   10   11   24
CONECT   11   12   12   16
CONECT   12   13   25
CONECT   13   14   14   26
CONECT   14   15   27
CONECT   15   16   16   28
CONECT   16   29
CONECT   17   30   31
END

HMDB0034212
     RDKit          3D
(R)-Kawain
 31 32  0  0  0  0  0  0  0  0999 V2000
   -5.1010    0.1763   -0.4265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9734    0.7698   -1.0423 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7183    0.7792   -0.4493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0317    1.8948   -0.4665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6914    1.9554    0.1459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0204    2.9975    0.1512 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2671    0.7528    0.7057 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6475   -0.4173   -0.0010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0753   -1.6283    0.5096 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1615   -1.8639    0.7238 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2442   -0.9585    0.4857 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4523   -1.1908    1.1800 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5847   -0.4479    1.0021 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6153    0.6013    0.1090 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4720    0.8619   -0.5855 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3106    0.0840   -0.3906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1927   -0.4328    0.1784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2479    0.7172    0.5457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9945   -0.9155   -0.2905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9988    0.3567   -1.0306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4668    2.7648   -0.9366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5378   -0.3026   -1.0718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7848   -2.4539    0.7437 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4599   -2.8881    1.1333 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4662   -1.9911    1.8798 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5056   -0.6467    1.5542 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5285    1.1726   -0.0093 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4465    1.6699   -1.2937 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4769    0.3233   -1.0135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3652   -0.3654    1.2837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6097   -1.3748   -0.2053 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  2  0
  8 17  1  0
 17  3  1  0
 16 11  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  4 21  1  0
  8 22  1  0
  9 23  1  0
 10 24  1  0
 12 25  1  0
 13 26  1  0
 14 27  1  0
 15 28  1  0
 16 29  1  0
 17 30  1  0
 17 31  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(+)-Kavain	HMDB
5,6-dihydro-4-Methoxy-6-styryl-(+)-2H-pyran-2-one	HMDB
DL-Kavain	HMDB
Gonosan	HMDB
Kavain	HMDB
Kawain	HMDB
Cavain	MeSH
Kavain, (R)-(e)-isomer	MeSH
Kavain, (R)-isomer	MeSH
Neuronica	MeSH
Kavain, (+-)-isomer	MeSH
Neuronika	MeSH
Kavain, (e)-(+-)-isomer	MeSH
Kavaine	MeSH

Chemical Formula

C₁₄H₁₄O₃

Average Molecular Weight

230.2592

Monoisotopic Molecular Weight

230.094294314

IUPAC Name

4-methoxy-6-[(Z)-2-phenylethenyl]-5,6-dihydro-2H-pyran-2-one

Traditional Name

4-methoxy-6-[(Z)-2-phenylethenyl]-5,6-dihydropyran-2-one

CAS Registry Number

500-64-1

SMILES

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

InChI Identifier

InChI=1S/C14H14O3/c1-16-13-9-12(17-14(15)10-13)8-7-11-5-3-2-4-6-11/h2-8,10,12H,9H2,1H3/b8-7-

InChI Key

XEAQIWGXBXCYFX-FPLPWBNLSA-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
Styrene
Dihydropyranone
Monocyclic benzene moiety
Pyran
Benzenoid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Vinylogous ester
Lactone
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Carbonyl group
Hydrocarbon derivative
Organooxygen compound
Organic oxide
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: HMDB0034212)

Cellular substructure

Membrane (HMDB: HMDB0034212)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0034212)

Source

Exogenous

Food

Food (HMDB: HMDB0034212)

Beverage

Beverages (FooDB: FOOD00870)

Not Available

Nutrient (HMDB: HMDB0034212)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	106 °C	Not Available
Boiling Point	432.64 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	1154 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	0.784 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.057 g/L	ALOGPS
logP	2.96	ALOGPS
logP	2.43	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	16.54	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	35.53 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	67.36 m³·mol⁻¹	ChemAxon
Polarizability	24.61 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	156.736	31661259
DarkChem	[M-H]-	155.89	31661259
DeepCCS	[M+H]+	153.734	30932474
DeepCCS	[M-H]-	151.339	30932474
DeepCCS	[M-2H]-	184.225	30932474
DeepCCS	[M+Na]+	159.79	30932474
AllCCS	[M+H]+	153.4	32859911
AllCCS	[M+H-H2O]+	149.2	32859911
AllCCS	[M+NH4]+	157.4	32859911
AllCCS	[M+Na]+	158.5	32859911
AllCCS	[M-H]-	155.6	32859911
AllCCS	[M+Na-2H]-	155.6	32859911
AllCCS	[M+HCOO]-	155.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(R)-Kawain	COC1=CC(=O)OC(C1)\C=C/C1=CC=CC=C1	3089.6	Standard polar	33892256
(R)-Kawain	COC1=CC(=O)OC(C1)\C=C/C1=CC=CC=C1	2099.5	Standard non polar	33892256
(R)-Kawain	COC1=CC(=O)OC(C1)\C=C/C1=CC=CC=C1	2269.6	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 - (R)-Kawain GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4u-8910000000-c6a57794a007db2deaef	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (R)-Kawain GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (R)-Kawain 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 - (R)-Kawain 10V, Positive-QTOF	splash10-001i-0390000000-60e9142259a68a089244	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Kawain 20V, Positive-QTOF	splash10-016r-1900000000-f519150517889a0a1a5a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Kawain 40V, Positive-QTOF	splash10-0v04-9800000000-775f9c525deb8bc70bdf	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Kawain 10V, Negative-QTOF	splash10-004i-0590000000-9eede89b2aa02e815511	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Kawain 20V, Negative-QTOF	splash10-002f-9350000000-04f5a56c63d80334cda3	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Kawain 40V, Negative-QTOF	splash10-054o-7900000000-e1030ac4fa32fd14fb8b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Kawain 10V, Negative-QTOF	splash10-004i-0090000000-642613d770f5140c7cd8	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Kawain 20V, Negative-QTOF	splash10-0ufr-0920000000-d311250adf6d19207525	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Kawain 40V, Negative-QTOF	splash10-004i-9300000000-8f7dd719d7b0d858637a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Kawain 10V, Positive-QTOF	splash10-001i-0290000000-496309742482a405757c	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Kawain 20V, Positive-QTOF	splash10-014i-4910000000-605abcf9e67e91ca3248	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Kawain 40V, Positive-QTOF	splash10-016r-6900000000-61ff41e817655bed8bba	2021-09-25	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

Not Available

METLIN ID

Not Available

PubChem Compound

45934481

PDB ID

Not Available

ChEBI ID

174183

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1396971

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Lin L, Chen Z, Yang X, Liu X, Feng X: Efficient enantioselective hetero-Diels-Alder reaction of Brassard's diene with aliphatic aldehydes: a one-step synthesis of (R)-(+)-kavain and (S)-(+)-dihydrokavain. Org Lett. 2008 Mar 20;10(6):1311-4. doi: 10.1021/ol8002282. Epub 2008 Feb 28. [PubMed:18303910 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for (R)-Kawain (HMDB0034212)

MOL for HMDB0034212 ((R)-Kawain)

3D MOL for HMDB0034212 ((R)-Kawain)

3D SDF for HMDB0034212 ((R)-Kawain)

3D-SDF for HMDB0034212 ((R)-Kawain)

PDB for HMDB0034212 ((R)-Kawain)

3D PDB for HMDB0034212 ((R)-Kawain)

SMILES for HMDB0034212 ((R)-Kawain)

INCHI for HMDB0034212 ((R)-Kawain)

Structure for HMDB0034212 ((R)-Kawain)

3D Structure for HMDB0034212 ((R)-Kawain)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra