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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-08-28 17:36:10 UTC

Update Date

2021-09-26 22:47:35 UTC

HMDB ID

HMDB0242214

Secondary Accession Numbers

None

Metabolite Identification

Common Name

(-)-Kawain

Description

4-methoxy-6-(2-phenylethenyl)-5,6-dihydro-2H-pyran-2-one 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. Based on a literature review very few articles have been published on 4-methoxy-6-(2-phenylethenyl)-5,6-dihydro-2H-pyran-2-one. This compound has been identified in human blood as reported by (PMID: 31557052 ). (-)-kawain is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically (-)-Kawain is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0242214
     RDKit          3D
(-)-Kawain
 31 32  0  0  0  0  0  0  0  0999 V2000
    4.1439    1.7022    1.3240 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7961    1.3129    1.1329 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4372    0.3715    0.1604 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1937   -0.6755   -0.0942 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8154   -1.6392   -1.0981 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5476   -2.6512   -1.3430 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6513   -1.4692   -1.8031 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5928   -0.7150   -1.1338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0263   -1.5321   -0.0923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1427   -1.4696    0.5376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2644   -0.5737    0.4945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3875    0.5299   -0.3023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5124    1.3697   -0.3057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5664    1.0982    0.5247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4715   -0.0044    1.3374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3713   -0.8153    1.3323 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1815    0.5624   -0.5924 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2003    2.4513    2.1381 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5999    2.1363    0.4123 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7538    0.8166    1.5943 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1150   -0.7751    0.4898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1465   -0.4938   -1.9238 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6205   -2.4028    0.2260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2573   -2.3199    1.2987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6130    0.8023   -0.9658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5795    2.2359   -0.9484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4390    1.7489    0.5227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3333   -0.2031    1.9980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3420   -1.6718    1.9894 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3512    1.2945   -1.4073 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4528    0.9793    0.1454 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  3
 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

  Mrv1533004171505552D          

 17 18  0  0  0  0            999 V2000
    2.1434   -1.2375    0.0000 C   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
    1.4289   -2.4750    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
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 O   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
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -6.6000    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
   -2.1434   -5.3625    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
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  3  9  1  0  0  0  0
 10  8  1  4  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0242214

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC(=O)OC(C1)C=CC1=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

> <INCHI_KEY>
XEAQIWGXBXCYFX-UHFFFAOYSA-N

> <FORMULA>
C14H14O3

> <MOLECULAR_WEIGHT>
230.263

> <EXACT_MASS>
230.094294311

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
24.966599517853695

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-methoxy-6-(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>
67.35770000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.73e-02 g/l

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

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0242214
     RDKit          3D
(-)-Kawain
 31 32  0  0  0  0  0  0  0  0999 V2000
    4.1439    1.7022    1.3240 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7961    1.3129    1.1329 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4372    0.3715    0.1604 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1937   -0.6755   -0.0942 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8154   -1.6392   -1.0981 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5476   -2.6512   -1.3430 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6513   -1.4692   -1.8031 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5928   -0.7150   -1.1338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0263   -1.5321   -0.0923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1427   -1.4696    0.5376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2644   -0.5737    0.4945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3875    0.5299   -0.3023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5124    1.3697   -0.3057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5664    1.0982    0.5247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4715   -0.0044    1.3374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3713   -0.8153    1.3323 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1815    0.5624   -0.5924 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2003    2.4513    2.1381 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5999    2.1363    0.4123 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7538    0.8166    1.5943 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1150   -0.7751    0.4898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1465   -0.4938   -1.9238 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6205   -2.4028    0.2260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2573   -2.3199    1.2987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6130    0.8023   -0.9658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5795    2.2359   -0.9484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4390    1.7489    0.5227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3333   -0.2031    1.9980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3420   -1.6718    1.9894 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3512    1.2945   -1.4073 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4528    0.9793    0.1454 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  3
 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                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       5.335  -7.700   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       2.667  -7.700   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    9                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8    3                                                       
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

COMPND    HMDB0242560
HETATM    1  C1  UNL     1      -4.597   0.794   1.174  1.00  0.00           C  
HETATM    2  O1  UNL     1      -4.165  -0.538   0.994  1.00  0.00           O  
HETATM    3  C2  UNL     1      -3.138  -0.746   0.052  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.455  -1.441  -1.021  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.409  -1.671  -2.016  1.00  0.00           C  
HETATM    6  O2  UNL     1      -2.718  -2.335  -3.036  1.00  0.00           O  
HETATM    7  O3  UNL     1      -1.125  -1.156  -1.805  1.00  0.00           O  
HETATM    8  C5  UNL     1      -1.093   0.025  -1.010  1.00  0.00           C  
HETATM    9  C6  UNL     1       0.327   0.415  -0.837  1.00  0.00           C  
HETATM   10  C7  UNL     1       1.131  -0.228  -0.016  1.00  0.00           C  
HETATM   11  C8  UNL     1       2.529   0.086   0.214  1.00  0.00           C  
HETATM   12  C9  UNL     1       3.120   1.130  -0.452  1.00  0.00           C  
HETATM   13  C10 UNL     1       4.462   1.387  -0.196  1.00  0.00           C  
HETATM   14  C11 UNL     1       5.233   0.665   0.680  1.00  0.00           C  
HETATM   15  C12 UNL     1       4.607  -0.374   1.330  1.00  0.00           C  
HETATM   16  C13 UNL     1       3.280  -0.661   1.103  1.00  0.00           C  
HETATM   17  C14 UNL     1      -1.787  -0.196   0.289  1.00  0.00           C  
HETATM   18  H1  UNL     1      -4.992   1.234   0.241  1.00  0.00           H  
HETATM   19  H2  UNL     1      -3.746   1.382   1.579  1.00  0.00           H  
HETATM   20  H3  UNL     1      -5.458   0.806   1.896  1.00  0.00           H  
HETATM   21  H4  UNL     1      -4.452  -1.834  -1.173  1.00  0.00           H  
HETATM   22  H5  UNL     1      -1.657   0.831  -1.550  1.00  0.00           H  
HETATM   23  H6  UNL     1       0.702   1.244  -1.399  1.00  0.00           H  
HETATM   24  H7  UNL     1       0.741  -1.091   0.570  1.00  0.00           H  
HETATM   25  H8  UNL     1       2.592   1.767  -1.172  1.00  0.00           H  
HETATM   26  H9  UNL     1       4.913   2.221  -0.736  1.00  0.00           H  
HETATM   27  H10 UNL     1       6.278   0.895   0.855  1.00  0.00           H  
HETATM   28  H11 UNL     1       5.214  -0.960   2.034  1.00  0.00           H  
HETATM   29  H12 UNL     1       2.830  -1.505   1.652  1.00  0.00           H  
HETATM   30  H13 UNL     1      -1.910   0.783   0.813  1.00  0.00           H  
HETATM   31  H14 UNL     1      -1.257  -0.930   0.941  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

HMDB0242214
     RDKit          3D
(-)-Kawain
 31 32  0  0  0  0  0  0  0  0999 V2000
    4.1439    1.7022    1.3240 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7961    1.3129    1.1329 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4372    0.3715    0.1604 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1937   -0.6755   -0.0942 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8154   -1.6392   -1.0981 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5476   -2.6512   -1.3430 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6513   -1.4692   -1.8031 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5928   -0.7150   -1.1338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0263   -1.5321   -0.0923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1427   -1.4696    0.5376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2644   -0.5737    0.4945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3875    0.5299   -0.3023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5124    1.3697   -0.3057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5664    1.0982    0.5247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4715   -0.0044    1.3374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3713   -0.8153    1.3323 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1815    0.5624   -0.5924 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2003    2.4513    2.1381 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5999    2.1363    0.4123 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7538    0.8166    1.5943 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1150   -0.7751    0.4898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1465   -0.4938   -1.9238 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6205   -2.4028    0.2260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2573   -2.3199    1.2987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6130    0.8023   -0.9658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5795    2.2359   -0.9484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4390    1.7489    0.5227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3333   -0.2031    1.9980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3420   -1.6718    1.9894 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3512    1.2945   -1.4073 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4528    0.9793    0.1454 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  3
 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
Neuronica	MeSH, HMDB
Neuronika	MeSH, HMDB
Cavain	MeSH, HMDB
Kavain, (+-)-isomer	MeSH, HMDB
Kavain, (e)-(+-)-isomer	MeSH, HMDB
Kavain, (R)-(e)-isomer	MeSH, HMDB
Kavain, (R)-isomer	MeSH, HMDB
Kavaine	MeSH, HMDB
Kawain	MeSH, HMDB

Chemical Formula

C₁₄H₁₄O₃

Average Molecular Weight

230.263

Monoisotopic Molecular Weight

230.094294311

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

COC1=CC(=O)OC(C1)C=CC1=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

InChI Key

XEAQIWGXBXCYFX-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
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

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

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
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	24.97 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
DeepCCS	[M+H]+	151.696	30932474
DeepCCS	[M-H]-	149.338	30932474
DeepCCS	[M-2H]-	182.315	30932474
DeepCCS	[M+Na]+	157.789	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

Not Available

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (-)-Kawain GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4u-8910000000-c6a57794a007db2deaef	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (-)-Kawain GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (-)-Kawain GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (-)-Kawain GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (-)-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 - (-)-Kawain 10V, Positive-QTOF	splash10-001i-0290000000-496309742482a405757c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Kawain 20V, Positive-QTOF	splash10-014i-4910000000-605abcf9e67e91ca3248	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Kawain 40V, Positive-QTOF	splash10-016r-6900000000-61ff41e817655bed8bba	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Kawain 10V, Negative-QTOF	splash10-004i-0090000000-642613d770f5140c7cd8	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Kawain 20V, Negative-QTOF	splash10-0ufr-0920000000-d311250adf6d19207525	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Kawain 40V, Negative-QTOF	splash10-004i-9300000000-8f7dd719d7b0d858637a	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

9948

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10376

PDB ID

Not Available

ChEBI ID

91863

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for (-)-Kawain (HMDB0242214)

MOL for HMDB0242214 ((-)-Kawain)

3D MOL for HMDB0242214 ((-)-Kawain)

3D SDF for HMDB0242214 ((-)-Kawain)

3D-SDF for HMDB0242214 ((-)-Kawain)

PDB for HMDB0242214 ((-)-Kawain)

3D PDB for HMDB0242214 ((-)-Kawain)

SMILES for HMDB0242214 ((-)-Kawain)

INCHI for HMDB0242214 ((-)-Kawain)

Structure for HMDB0242214 ((-)-Kawain)

3D Structure for HMDB0242214 ((-)-Kawain)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

GC-MS Spectra

MS/MS Spectra