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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 19:04:29 UTC

Update Date

2022-03-07 02:54:02 UTC

HMDB ID

HMDB0034270

Secondary Accession Numbers

HMDB34270

Metabolite Identification

Common Name

5,6-Dihydro-5-hydroxy-6-methyl-2H-pyran-2-one

Description

5,6-Dihydro-5-hydroxy-6-methyl-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. 5,6-Dihydro-5-hydroxy-6-methyl-2H-pyran-2-one has been detected, but not quantified in, beverages. This could make 5,6-dihydro-5-hydroxy-6-methyl-2H-pyran-2-one a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 5,6-Dihydro-5-hydroxy-6-methyl-2H-pyran-2-one.

Structure

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

HMDB0034270
     RDKit          3D
5,6-Dihydro-5-hydroxy-6-methyl-2H-pyran-2-one
 29 30  0  0  0  0  0  0  0  0999 V2000
    5.3570    0.5202    0.6416 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9731    0.7210    0.6964 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1449   -0.2058    0.0398 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7634   -0.0010    0.0973 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9190   -0.8716   -0.5232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5351   -0.7071   -0.4963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1030    0.2898    0.1282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5607    0.4868    0.1762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1015    1.5631    0.8546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4727    1.7859    0.9245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3606    0.9309    0.3118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8357   -0.1437   -0.3663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4511   -0.3643   -0.4340 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4466   -1.9048   -1.1738 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7298   -2.1155   -1.2407 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1942   -3.1226   -1.8778 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6364   -1.2754   -0.6369 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6217   -0.3932    1.2422 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8910    1.4106    1.0645 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6383    0.3542   -0.4214 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3962    0.8738    0.6526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1582   -1.4225   -1.0021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5200    1.0555    0.6649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4042    2.2517    1.3470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8641    2.6381    1.4636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4214    1.1220    0.3782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5298   -0.8165   -0.8482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0968   -1.2160   -0.9749 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7032   -1.4434   -0.6878 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
  5 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17  3  2  0
 13  8  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  4 21  1  0
  6 22  1  0
  7 23  1  0
  9 24  1  0
 10 25  1  0
 11 26  1  0
 12 27  1  0
 13 28  1  0
 17 29  1  0
M  END


  Mrv0541 05061307412D          

 17 18  0  0  0  0            999 V2000
   -0.7145    2.0625    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
    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
    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
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    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
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    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  2  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>
HMDB0034270

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C14H12O3/c1-16-13-9-12(17-14(15)10-13)8-7-11-5-3-2-4-6-11/h2-10H,1H3/b8-7+

> <INCHI_KEY>
DKKJNZYHGRUXBS-BQYQJAHWSA-N

> <FORMULA>
C14H12O3

> <MOLECULAR_WEIGHT>
228.2433

> <EXACT_MASS>
228.07864425

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
24.417347840506867

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-methoxy-6-[(E)-2-phenylethenyl]-2H-pyran-2-one

> <ALOGPS_LOGP>
3.20

> <JCHEM_LOGP>
2.639489875

> <ALOGPS_LOGS>
-3.76

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.827159191016256

> <JCHEM_POLAR_SURFACE_AREA>
35.53

> <JCHEM_REFRACTIVITY>
68.7407

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.98e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
desmethoxyyangonin

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0034270
     RDKit          3D
5,6-Dihydro-5-hydroxy-6-methyl-2H-pyran-2-one
 29 30  0  0  0  0  0  0  0  0999 V2000
    5.3570    0.5202    0.6416 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9731    0.7210    0.6964 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1449   -0.2058    0.0398 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7634   -0.0010    0.0973 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9190   -0.8716   -0.5232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5351   -0.7071   -0.4963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1030    0.2898    0.1282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5607    0.4868    0.1762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1015    1.5631    0.8546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4727    1.7859    0.9245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3606    0.9309    0.3118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8357   -0.1437   -0.3663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4511   -0.3643   -0.4340 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4466   -1.9048   -1.1738 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7298   -2.1155   -1.2407 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1942   -3.1226   -1.8778 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6364   -1.2754   -0.6369 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6217   -0.3932    1.2422 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8910    1.4106    1.0645 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6383    0.3542   -0.4214 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3962    0.8738    0.6526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1582   -1.4225   -1.0021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5200    1.0555    0.6649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4042    2.2517    1.3470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8641    2.6381    1.4636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4214    1.1220    0.3782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5298   -0.8165   -0.8482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0968   -1.2160   -0.9749 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7032   -1.4434   -0.6878 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
  5 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17  3  2  0
 13  8  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  4 21  1  0
  6 22  1  0
  7 23  1  0
  9 24  1  0
 10 25  1  0
 11 26  1  0
 12 27  1  0
 13 28  1  0
 17 29  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   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -7.700   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       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       2.667   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    HMDB0034270
HETATM    1  C1  UNL     1       5.357   0.520   0.642  1.00  0.00           C  
HETATM    2  O1  UNL     1       3.973   0.721   0.696  1.00  0.00           O  
HETATM    3  C2  UNL     1       3.145  -0.206   0.040  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.763  -0.001   0.097  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.919  -0.872  -0.523  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.535  -0.707  -0.496  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.103   0.290   0.128  1.00  0.00           C  
HETATM    8  C7  UNL     1      -2.561   0.487   0.176  1.00  0.00           C  
HETATM    9  C8  UNL     1      -3.102   1.563   0.855  1.00  0.00           C  
HETATM   10  C9  UNL     1      -4.473   1.786   0.924  1.00  0.00           C  
HETATM   11  C10 UNL     1      -5.361   0.931   0.312  1.00  0.00           C  
HETATM   12  C11 UNL     1      -4.836  -0.144  -0.366  1.00  0.00           C  
HETATM   13  C12 UNL     1      -3.451  -0.364  -0.434  1.00  0.00           C  
HETATM   14  O2  UNL     1       1.447  -1.905  -1.174  1.00  0.00           O  
HETATM   15  C13 UNL     1       2.730  -2.116  -1.241  1.00  0.00           C  
HETATM   16  O3  UNL     1       3.194  -3.123  -1.878  1.00  0.00           O  
HETATM   17  C14 UNL     1       3.636  -1.275  -0.637  1.00  0.00           C  
HETATM   18  H1  UNL     1       5.622  -0.393   1.242  1.00  0.00           H  
HETATM   19  H2  UNL     1       5.891   1.411   1.064  1.00  0.00           H  
HETATM   20  H3  UNL     1       5.638   0.354  -0.421  1.00  0.00           H  
HETATM   21  H4  UNL     1       1.396   0.874   0.653  1.00  0.00           H  
HETATM   22  H5  UNL     1      -1.158  -1.423  -1.002  1.00  0.00           H  
HETATM   23  H6  UNL     1      -0.520   1.055   0.665  1.00  0.00           H  
HETATM   24  H7  UNL     1      -2.404   2.252   1.347  1.00  0.00           H  
HETATM   25  H8  UNL     1      -4.864   2.638   1.464  1.00  0.00           H  
HETATM   26  H9  UNL     1      -6.421   1.122   0.378  1.00  0.00           H  
HETATM   27  H10 UNL     1      -5.530  -0.817  -0.848  1.00  0.00           H  
HETATM   28  H11 UNL     1      -3.097  -1.216  -0.975  1.00  0.00           H  
HETATM   29  H12 UNL     1       4.703  -1.443  -0.688  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3
CONECT    3    4   17   17
CONECT    4    5    5   21
CONECT    5    6   14
CONECT    6    7    7   22
CONECT    7    8   23
CONECT    8    9    9   13
CONECT    9   10   24
CONECT   10   11   11   25
CONECT   11   12   26
CONECT   12   13   13   27
CONECT   13   28
CONECT   14   15
CONECT   15   16   16   17
CONECT   17   29
END

HMDB0034270
     RDKit          3D
5,6-Dihydro-5-hydroxy-6-methyl-2H-pyran-2-one
 29 30  0  0  0  0  0  0  0  0999 V2000
    5.3570    0.5202    0.6416 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9731    0.7210    0.6964 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1449   -0.2058    0.0398 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7634   -0.0010    0.0973 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9190   -0.8716   -0.5232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5351   -0.7071   -0.4963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1030    0.2898    0.1282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5607    0.4868    0.1762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1015    1.5631    0.8546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4727    1.7859    0.9245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3606    0.9309    0.3118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8357   -0.1437   -0.3663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4511   -0.3643   -0.4340 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4466   -1.9048   -1.1738 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7298   -2.1155   -1.2407 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1942   -3.1226   -1.8778 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6364   -1.2754   -0.6369 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6217   -0.3932    1.2422 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8910    1.4106    1.0645 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6383    0.3542   -0.4214 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3962    0.8738    0.6526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1582   -1.4225   -1.0021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5200    1.0555    0.6649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4042    2.2517    1.3470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8641    2.6381    1.4636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4214    1.1220    0.3782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5298   -0.8165   -0.8482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0968   -1.2160   -0.9749 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7032   -1.4434   -0.6878 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
  5 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17  3  2  0
 13  8  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  4 21  1  0
  6 22  1  0
  7 23  1  0
  9 24  1  0
 10 25  1  0
 11 26  1  0
 12 27  1  0
 13 28  1  0
 17 29  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
56-Dehydrokawain	ChEMBL, HMDB
56-Dehydrokawin	ChEMBL, HMDB
(e)-4-Methoxy-6-(2-phenylethenyl)-2H-pyran-2-one	HMDB
2H-Pyran-2-one, 4-methoxy-6-(2-phenylethenyl)-, (e)- (9ci)	HMDB
4-Methoxy-6-(2-phenylethenyl)-(e)-2H-pyran-2-one	HMDB
4-Methoxy-6-(2-phenylethenyl)-2H-pyran-2-one	HMDB
4-Methoxy-6-styryl-(e)-2H-pyran-2-one	HMDB
4-Methoxy-6-styryl-2H-pyran-2-one	HMDB
4-Methoxy-6-[(e)-2-phenylethenyl]-2H-pyran-2-one	HMDB
4-Methoxy-6-[(e)-2-phenylvinyl]-2H-pyran-2-one	HMDB
5,6-Dehydrokawain	HMDB
Demethoxyyangonin	HMDB
Desmethoxyyangonin	HMDB
DMY	HMDB
5,6-Dehydrokawain, (e)-isomer	MeSH, HMDB

Chemical Formula

C₁₄H₁₂O₃

Average Molecular Weight

228.2433

Monoisotopic Molecular Weight

228.07864425

IUPAC Name

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

Traditional Name

desmethoxyyangonin

CAS Registry Number

15345-89-8

SMILES

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

InChI Identifier

InChI=1S/C14H12O3/c1-16-13-9-12(17-14(15)10-13)8-7-11-5-3-2-4-6-11/h2-10H,1H3/b8-7+

InChI Key

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

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

aromatic ether (CHEBI:1995 )
2-pyranones (CHEBI:1995 )
alpha-Pyrones (C09925 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0034270)
Cell membrane (HMDB: HMDB0034270)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0034270)

Source

Exogenous

Exogenous (HMDB: HMDB0034270)

Food

Food (HMDB: HMDB0034270)

Beverage

Beverages (FooDB: FOOD00870)

Endogenous

Plant

Plant (HMDB: HMDB0034270)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0034270)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	138 - 140 °C	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	0.04 g/L	ALOGPS
logP	3.2	ALOGPS
logP	2.64	ChemAxon
logS	-3.8	ALOGPS
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	68.74 m³·mol⁻¹	ChemAxon
Polarizability	24.42 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]+	156.089	31661259
DarkChem	[M-H]-	156.516	31661259
DeepCCS	[M+H]+	156.029	30932474
DeepCCS	[M-H]-	153.646	30932474
DeepCCS	[M-2H]-	186.575	30932474
DeepCCS	[M+Na]+	162.097	30932474
AllCCS	[M+H]+	149.9	32859911
AllCCS	[M+H-H2O]+	145.5	32859911
AllCCS	[M+NH4]+	154.0	32859911
AllCCS	[M+Na]+	155.1	32859911
AllCCS	[M-H]-	151.2	32859911
AllCCS	[M+Na-2H]-	150.9	32859911
AllCCS	[M+HCOO]-	150.7	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022.	8.89 minutes	32390414
Predicted by Siyang on May 30, 2022	13.9598 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.05 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2137.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	453.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	180.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	247.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	185.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	566.5 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	604.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	130.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1326.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	432.3 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1337.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	374.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	363.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	373.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	362.8 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	10.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5,6-Dihydro-5-hydroxy-6-methyl-2H-pyran-2-one	COC1=CC(=O)OC(\C=C\C2=CC=CC=C2)=C1	3324.9	Standard polar	33892256
5,6-Dihydro-5-hydroxy-6-methyl-2H-pyran-2-one	COC1=CC(=O)OC(\C=C\C2=CC=CC=C2)=C1	2141.8	Standard non polar	33892256
5,6-Dihydro-5-hydroxy-6-methyl-2H-pyran-2-one	COC1=CC(=O)OC(\C=C\C2=CC=CC=C2)=C1	2370.9	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 5,6-Dihydro-5-hydroxy-6-methyl-2H-pyran-2-one GC-MS (Non-derivatized) - 70eV, Positive	splash10-01tc-4970000000-5313253d81990e8f899d	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5,6-Dihydro-5-hydroxy-6-methyl-2H-pyran-2-one 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 - 5,6-Dihydro-5-hydroxy-6-methyl-2H-pyran-2-one , positive-QTOF	splash10-0ufu-0930000000-c45b0f14494494198c6c	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-Dihydro-5-hydroxy-6-methyl-2H-pyran-2-one 10V, Positive-QTOF	splash10-004i-0190000000-69ef56e66ed3e2d76e85	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-Dihydro-5-hydroxy-6-methyl-2H-pyran-2-one 20V, Positive-QTOF	splash10-004i-1790000000-646967bbc7e9bc2ac6fd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-Dihydro-5-hydroxy-6-methyl-2H-pyran-2-one 40V, Positive-QTOF	splash10-0fb9-3910000000-b624986462c7f4bc3a12	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-Dihydro-5-hydroxy-6-methyl-2H-pyran-2-one 10V, Negative-QTOF	splash10-004i-0490000000-c2f830d977ce499b03bc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-Dihydro-5-hydroxy-6-methyl-2H-pyran-2-one 20V, Negative-QTOF	splash10-002f-9340000000-ee86bc62eed6a5fd4577	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-Dihydro-5-hydroxy-6-methyl-2H-pyran-2-one 40V, Negative-QTOF	splash10-002f-8900000000-92e15b6d1ede62fa6571	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-Dihydro-5-hydroxy-6-methyl-2H-pyran-2-one 10V, Negative-QTOF	splash10-004i-0090000000-f0e0fc28215258fdeb31	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-Dihydro-5-hydroxy-6-methyl-2H-pyran-2-one 20V, Negative-QTOF	splash10-004i-0690000000-317865019d785558fd79	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-Dihydro-5-hydroxy-6-methyl-2H-pyran-2-one 40V, Negative-QTOF	splash10-004i-9100000000-818ce39c4616027934e5	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-Dihydro-5-hydroxy-6-methyl-2H-pyran-2-one 10V, Positive-QTOF	splash10-004i-0290000000-c05a8d84225eb8226a2f	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-Dihydro-5-hydroxy-6-methyl-2H-pyran-2-one 20V, Positive-QTOF	splash10-004i-3970000000-057a25d403e514d8d120	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-Dihydro-5-hydroxy-6-methyl-2H-pyran-2-one 40V, Positive-QTOF	splash10-004i-6900000000-8178f04b27a5dbcbba65	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

5273621

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 5,6-Dihydro-5-hydroxy-6-methyl-2H-pyran-2-one (HMDB0034270)

MOL for HMDB0034270 (5,6-Dihydro-5-hydroxy-6-methyl-2H-pyran-2-one)

3D MOL for HMDB0034270 (5,6-Dihydro-5-hydroxy-6-methyl-2H-pyran-2-one)

3D SDF for HMDB0034270 (5,6-Dihydro-5-hydroxy-6-methyl-2H-pyran-2-one)

3D-SDF for HMDB0034270 (5,6-Dihydro-5-hydroxy-6-methyl-2H-pyran-2-one)

PDB for HMDB0034270 (5,6-Dihydro-5-hydroxy-6-methyl-2H-pyran-2-one)

3D PDB for HMDB0034270 (5,6-Dihydro-5-hydroxy-6-methyl-2H-pyran-2-one)

SMILES for HMDB0034270 (5,6-Dihydro-5-hydroxy-6-methyl-2H-pyran-2-one)

INCHI for HMDB0034270 (5,6-Dihydro-5-hydroxy-6-methyl-2H-pyran-2-one)

Structure for HMDB0034270 (5,6-Dihydro-5-hydroxy-6-methyl-2H-pyran-2-one)

3D Structure for HMDB0034270 (5,6-Dihydro-5-hydroxy-6-methyl-2H-pyran-2-one)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra