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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:31:14 UTC

Update Date

2022-03-07 02:52:12 UTC

HMDB ID

HMDB0029575

Secondary Accession Numbers

HMDB29575

Metabolite Identification

Common Name

(+)-cis-5,6-Dihydro-5-hydroxy-4-methoxy-6-(2-phenylethyl)-2H-pyran-2-one

Description

(+)-cis-5,6-Dihydro-5-hydroxy-4-methoxy-6-(2-phenylethyl)-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 (+)-cis-5,6-Dihydro-5-hydroxy-4-methoxy-6-(2-phenylethyl)-2H-pyran-2-one.

Structure

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

HMDB0029575
     RDKit          3D
(+)-cis-5,6-Dihydro-5-hydroxy-4-methoxy-6-(2-phenylethyl)-2H-pyran-2-one
 34 35  0  0  0  0  0  0  0  0999 V2000
   -4.8983   -0.4779   -1.3976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5055   -0.7222   -1.4105 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7187   -0.2470   -0.3300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5559    1.0457   -0.1486 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7553    1.5348    0.9507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6107    2.7918    1.1080 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1644    0.6295    1.8065 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8742   -0.6570    1.2769 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2901   -0.4838    0.3237 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4423    0.0749    1.1622 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6505    0.2880    0.3271 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8866    1.4798   -0.3182 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0252    1.6592   -1.0963 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9608    0.6578   -1.2541 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7213   -0.5360   -0.6059 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5819   -0.7183    0.1739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0909   -1.2268    0.5802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9970   -1.5739    1.6054 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3093   -0.9354   -2.3334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4122   -0.8946   -0.5270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1305    0.6056   -1.4610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0437    1.7304   -0.8530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5244   -1.3329    2.0835 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5959   -1.4170   -0.1492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0159    0.2497   -0.4336 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1119    1.0176    1.6532 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6116   -0.6558    1.9768 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1526    2.2574   -0.1910 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2083    2.5847   -1.5972 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8501    0.7956   -1.8608 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4447   -1.3391   -0.7158 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3774   -1.6485    0.6900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8072   -2.1369    0.0143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4972   -2.3994    1.3840 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  1  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 18  1  0
 17  3  1  0
 16 11  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  0
  8 23  1  0
  9 24  1  0
  9 25  1  0
 10 26  1  0
 10 27  1  0
 12 28  1  0
 13 29  1  0
 14 30  1  0
 15 31  1  0
 16 32  1  0
 17 33  1  0
 18 34  1  0
M  END


  Mrv0541 05061304492D          

 18 19  0  0  0  0            999 V2000
    1.4289    8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.9500    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
    3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    7.0125    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
    4.2868    7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    6.1875    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  1  0  0  0  0
 10  5  2  0  0  0  0
 10  6  1  0  0  0  0
 10  7  1  0  0  0  0
 11  8  1  0  0  0  0
 12  9  2  0  0  0  0
 13  9  1  0  0  0  0
 14 11  1  0  0  0  0
 14 12  1  0  0  0  0
 15 13  2  0  0  0  0
 16 14  1  0  0  0  0
 17  1  1  0  0  0  0
 17 12  1  0  0  0  0
 18 11  1  0  0  0  0
 18 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0029575

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC(=O)OC(CCC2=CC=CC=C2)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C14H16O4/c1-17-12-9-13(15)18-11(14(12)16)8-7-10-5-3-2-4-6-10/h2-6,9,11,14,16H,7-8H2,1H3

> <INCHI_KEY>
VJCNEDVMYQCMBK-UHFFFAOYSA-N

> <FORMULA>
C14H16O4

> <MOLECULAR_WEIGHT>
248.2744

> <EXACT_MASS>
248.104859

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
26.17032942332742

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-hydroxy-4-methoxy-6-(2-phenylethyl)-5,6-dihydro-2H-pyran-2-one

> <ALOGPS_LOGP>
1.93

> <JCHEM_LOGP>
1.8657311943333335

> <ALOGPS_LOGS>
-2.27

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.865919778239032

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7322264747673133

> <JCHEM_POLAR_SURFACE_AREA>
55.760000000000005

> <JCHEM_REFRACTIVITY>
67.49220000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.33e+00 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0029575
     RDKit          3D
(+)-cis-5,6-Dihydro-5-hydroxy-4-methoxy-6-(2-phenylethyl)-2H-pyran-2-one
 34 35  0  0  0  0  0  0  0  0999 V2000
   -4.8983   -0.4779   -1.3976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5055   -0.7222   -1.4105 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7187   -0.2470   -0.3300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5559    1.0457   -0.1486 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7553    1.5348    0.9507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6107    2.7918    1.1080 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1644    0.6295    1.8065 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8742   -0.6570    1.2769 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2901   -0.4838    0.3237 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4423    0.0749    1.1622 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6505    0.2880    0.3271 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8866    1.4798   -0.3182 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0252    1.6592   -1.0963 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9608    0.6578   -1.2541 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7213   -0.5360   -0.6059 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5819   -0.7183    0.1739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0909   -1.2268    0.5802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9970   -1.5739    1.6054 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3093   -0.9354   -2.3334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4122   -0.8946   -0.5270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1305    0.6056   -1.4610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0437    1.7304   -0.8530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5244   -1.3329    2.0835 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5959   -1.4170   -0.1492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0159    0.2497   -0.4336 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1119    1.0176    1.6532 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6116   -0.6558    1.9768 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1526    2.2574   -0.1910 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2083    2.5847   -1.5972 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8501    0.7956   -1.8608 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4447   -1.3391   -0.7158 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3774   -1.6485    0.6900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8072   -2.1369    0.0143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4972   -2.3994    1.3840 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  1  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 18  1  0
 17  3  1  0
 16 11  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  0
  8 23  1  0
  9 24  1  0
  9 25  1  0
 10 26  1  0
 10 27  1  0
 12 28  1  0
 13 29  1  0
 14 30  1  0
 15 31  1  0
 16 32  1  0
 17 33  1  0
 18 34  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       2.667  15.400   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668   8.470   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335   9.240   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335  13.860   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335  10.780   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001  13.090   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668  13.090   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001  11.550   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       8.002  13.860   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       2.667  10.780   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       2.667  13.860   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       6.668  11.550   0.000  0.00  0.00           O+0
CONECT    1   17                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3   10                                                       
CONECT    6    4   10                                                       
CONECT    7    8   10                                                       
CONECT    8    7   11                                                       
CONECT    9   12   13                                                       
CONECT   10    5    6    7                                                  
CONECT   11    8   14   18                                                  
CONECT   12    9   14   17                                                  
CONECT   13    9   15   18                                                  
CONECT   14   11   12   16                                                  
CONECT   15   13                                                            
CONECT   16   14                                                            
CONECT   17    1   12                                                       
CONECT   18   11   13                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

COMPND    HMDB0029575
HETATM    1  C1  UNL     1      -4.898  -0.478  -1.398  1.00  0.00           C  
HETATM    2  O1  UNL     1      -3.506  -0.722  -1.411  1.00  0.00           O  
HETATM    3  C2  UNL     1      -2.719  -0.247  -0.330  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.556   1.046  -0.149  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.755   1.535   0.951  1.00  0.00           C  
HETATM    6  O2  UNL     1      -1.611   2.792   1.108  1.00  0.00           O  
HETATM    7  O3  UNL     1      -1.164   0.629   1.807  1.00  0.00           O  
HETATM    8  C5  UNL     1      -0.874  -0.657   1.277  1.00  0.00           C  
HETATM    9  C6  UNL     1       0.290  -0.484   0.324  1.00  0.00           C  
HETATM   10  C7  UNL     1       1.442   0.075   1.162  1.00  0.00           C  
HETATM   11  C8  UNL     1       2.650   0.288   0.327  1.00  0.00           C  
HETATM   12  C9  UNL     1       2.887   1.480  -0.318  1.00  0.00           C  
HETATM   13  C10 UNL     1       4.025   1.659  -1.096  1.00  0.00           C  
HETATM   14  C11 UNL     1       4.961   0.658  -1.254  1.00  0.00           C  
HETATM   15  C12 UNL     1       4.721  -0.536  -0.606  1.00  0.00           C  
HETATM   16  C13 UNL     1       3.582  -0.718   0.174  1.00  0.00           C  
HETATM   17  C14 UNL     1      -2.091  -1.227   0.580  1.00  0.00           C  
HETATM   18  O4  UNL     1      -2.997  -1.574   1.605  1.00  0.00           O  
HETATM   19  H1  UNL     1      -5.309  -0.935  -2.333  1.00  0.00           H  
HETATM   20  H2  UNL     1      -5.412  -0.895  -0.527  1.00  0.00           H  
HETATM   21  H3  UNL     1      -5.131   0.606  -1.461  1.00  0.00           H  
HETATM   22  H4  UNL     1      -3.044   1.730  -0.853  1.00  0.00           H  
HETATM   23  H5  UNL     1      -0.524  -1.333   2.083  1.00  0.00           H  
HETATM   24  H6  UNL     1       0.596  -1.417  -0.149  1.00  0.00           H  
HETATM   25  H7  UNL     1      -0.016   0.250  -0.434  1.00  0.00           H  
HETATM   26  H8  UNL     1       1.112   1.018   1.653  1.00  0.00           H  
HETATM   27  H9  UNL     1       1.612  -0.656   1.977  1.00  0.00           H  
HETATM   28  H10 UNL     1       2.153   2.257  -0.191  1.00  0.00           H  
HETATM   29  H11 UNL     1       4.208   2.585  -1.597  1.00  0.00           H  
HETATM   30  H12 UNL     1       5.850   0.796  -1.861  1.00  0.00           H  
HETATM   31  H13 UNL     1       5.445  -1.339  -0.716  1.00  0.00           H  
HETATM   32  H14 UNL     1       3.377  -1.648   0.690  1.00  0.00           H  
HETATM   33  H15 UNL     1      -1.807  -2.137   0.014  1.00  0.00           H  
HETATM   34  H16 UNL     1      -3.497  -2.399   1.384  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3
CONECT    3    4    4   17
CONECT    4    5   22
CONECT    5    6    6    7
CONECT    7    8
CONECT    8    9   17   23
CONECT    9   10   24   25
CONECT   10   11   26   27
CONECT   11   12   12   16
CONECT   12   13   28
CONECT   13   14   14   29
CONECT   14   15   30
CONECT   15   16   16   31
CONECT   16   32
CONECT   17   18   33
CONECT   18   34
END

HMDB0029575
     RDKit          3D
(+)-cis-5,6-Dihydro-5-hydroxy-4-methoxy-6-(2-phenylethyl)-2H-pyran-2-one
 34 35  0  0  0  0  0  0  0  0999 V2000
   -4.8983   -0.4779   -1.3976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5055   -0.7222   -1.4105 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7187   -0.2470   -0.3300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5559    1.0457   -0.1486 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7553    1.5348    0.9507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6107    2.7918    1.1080 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1644    0.6295    1.8065 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8742   -0.6570    1.2769 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2901   -0.4838    0.3237 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4423    0.0749    1.1622 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6505    0.2880    0.3271 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8866    1.4798   -0.3182 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0252    1.6592   -1.0963 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9608    0.6578   -1.2541 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7213   -0.5360   -0.6059 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5819   -0.7183    0.1739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0909   -1.2268    0.5802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9970   -1.5739    1.6054 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3093   -0.9354   -2.3334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4122   -0.8946   -0.5270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1305    0.6056   -1.4610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0437    1.7304   -0.8530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5244   -1.3329    2.0835 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5959   -1.4170   -0.1492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0159    0.2497   -0.4336 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1119    1.0176    1.6532 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6116   -0.6558    1.9768 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1526    2.2574   -0.1910 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2083    2.5847   -1.5972 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8501    0.7956   -1.8608 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4447   -1.3391   -0.7158 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3774   -1.6485    0.6900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8072   -2.1369    0.0143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4972   -2.3994    1.3840 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  1  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 18  1  0
 17  3  1  0
 16 11  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  0
  8 23  1  0
  9 24  1  0
  9 25  1  0
 10 26  1  0
 10 27  1  0
 12 28  1  0
 13 29  1  0
 14 30  1  0
 15 31  1  0
 16 32  1  0
 17 33  1  0
 18 34  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₄H₁₆O₄

Average Molecular Weight

248.2744

Monoisotopic Molecular Weight

248.104859

IUPAC Name

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

Traditional Name

5-hydroxy-4-methoxy-6-(2-phenylethyl)-5,6-dihydropyran-2-one

CAS Registry Number

52247-81-1

SMILES

COC1=CC(=O)OC(CCC2=CC=CC=C2)C1O

InChI Identifier

InChI=1S/C14H16O4/c1-17-12-9-13(15)18-11(14(12)16)8-7-10-5-3-2-4-6-10/h2-6,9,11,14,16H,7-8H2,1H3

InChI Key

VJCNEDVMYQCMBK-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
Dihydropyranone
Monocyclic benzene moiety
Pyran
Benzenoid
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Vinylogous ester
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organoheterocyclic compound
Alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0029575)
Cytoplasm (HMDB: HMDB0029575)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0029575)

Source

Endogenous

Endogenous (HMDB: HMDB0029575)

Plant

Plant (HMDB: HMDB0029575)

Exogenous

Food

Food (HMDB: HMDB0029575)

Beverage

Beverages (FooDB: FOOD00870)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	92 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	40170 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.33 g/L	ALOGPS
logP	1.93	ALOGPS
logP	1.87	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	12.87	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.76 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	67.49 m³·mol⁻¹	ChemAxon
Polarizability	26.17 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]+	159.966	31661259
DarkChem	[M-H]-	159.345	31661259
DeepCCS	[M+H]+	154.186	30932474
DeepCCS	[M-H]-	151.828	30932474
DeepCCS	[M-2H]-	184.965	30932474
DeepCCS	[M+Na]+	160.279	30932474
AllCCS	[M+H]+	159.4	32859911
AllCCS	[M+H-H2O]+	155.3	32859911
AllCCS	[M+NH4]+	163.1	32859911
AllCCS	[M+Na]+	164.2	32859911
AllCCS	[M-H]-	160.8	32859911
AllCCS	[M+Na-2H]-	160.9	32859911
AllCCS	[M+HCOO]-	161.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(+)-cis-5,6-Dihydro-5-hydroxy-4-methoxy-6-(2-phenylethyl)-2H-pyran-2-one	COC1=CC(=O)OC(CCC2=CC=CC=C2)C1O	3611.6	Standard polar	33892256
(+)-cis-5,6-Dihydro-5-hydroxy-4-methoxy-6-(2-phenylethyl)-2H-pyran-2-one	COC1=CC(=O)OC(CCC2=CC=CC=C2)C1O	2107.3	Standard non polar	33892256
(+)-cis-5,6-Dihydro-5-hydroxy-4-methoxy-6-(2-phenylethyl)-2H-pyran-2-one	COC1=CC(=O)OC(CCC2=CC=CC=C2)C1O	2346.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(+)-cis-5,6-Dihydro-5-hydroxy-4-methoxy-6-(2-phenylethyl)-2H-pyran-2-one,1TMS,isomer #1	COC1=CC(=O)OC(CCC2=CC=CC=C2)C1O[Si](C)(C)C	2181.3	Semi standard non polar	33892256
(+)-cis-5,6-Dihydro-5-hydroxy-4-methoxy-6-(2-phenylethyl)-2H-pyran-2-one,1TBDMS,isomer #1	COC1=CC(=O)OC(CCC2=CC=CC=C2)C1O[Si](C)(C)C(C)(C)C	2411.3	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 - (+)-cis-5,6-Dihydro-5-hydroxy-4-methoxy-6-(2-phenylethyl)-2H-pyran-2-one GC-MS (Non-derivatized) - 70eV, Positive	splash10-0536-9530000000-a488163ec5c48c7a46fb	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (+)-cis-5,6-Dihydro-5-hydroxy-4-methoxy-6-(2-phenylethyl)-2H-pyran-2-one GC-MS (1 TMS) - 70eV, Positive	splash10-0006-9220000000-1adf6da0e5c6894e8b73	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (+)-cis-5,6-Dihydro-5-hydroxy-4-methoxy-6-(2-phenylethyl)-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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-cis-5,6-Dihydro-5-hydroxy-4-methoxy-6-(2-phenylethyl)-2H-pyran-2-one 10V, Positive-QTOF	splash10-0002-1390000000-f753eb289d81bcfea4ba	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-cis-5,6-Dihydro-5-hydroxy-4-methoxy-6-(2-phenylethyl)-2H-pyran-2-one 20V, Positive-QTOF	splash10-014l-3920000000-88c1c9875b067e37030b	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-cis-5,6-Dihydro-5-hydroxy-4-methoxy-6-(2-phenylethyl)-2H-pyran-2-one 40V, Positive-QTOF	splash10-014i-7900000000-625c9170ea4ef190dbff	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-cis-5,6-Dihydro-5-hydroxy-4-methoxy-6-(2-phenylethyl)-2H-pyran-2-one 10V, Negative-QTOF	splash10-0002-0290000000-55c35b6e7f90b7f0acc7	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-cis-5,6-Dihydro-5-hydroxy-4-methoxy-6-(2-phenylethyl)-2H-pyran-2-one 20V, Negative-QTOF	splash10-0006-9340000000-f4f90fef482ea541be38	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-cis-5,6-Dihydro-5-hydroxy-4-methoxy-6-(2-phenylethyl)-2H-pyran-2-one 40V, Negative-QTOF	splash10-0006-9400000000-a0ae12a774ae15948b98	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-cis-5,6-Dihydro-5-hydroxy-4-methoxy-6-(2-phenylethyl)-2H-pyran-2-one 10V, Positive-QTOF	splash10-0002-0390000000-93e8b27c7be16db2503f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-cis-5,6-Dihydro-5-hydroxy-4-methoxy-6-(2-phenylethyl)-2H-pyran-2-one 20V, Positive-QTOF	splash10-0a4l-5900000000-51d4299d087afdbd604c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-cis-5,6-Dihydro-5-hydroxy-4-methoxy-6-(2-phenylethyl)-2H-pyran-2-one 40V, Positive-QTOF	splash10-00kf-9400000000-761308f567c06adedf3a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-cis-5,6-Dihydro-5-hydroxy-4-methoxy-6-(2-phenylethyl)-2H-pyran-2-one 10V, Negative-QTOF	splash10-0002-0790000000-e7ab5232365d04d117f9	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-cis-5,6-Dihydro-5-hydroxy-4-methoxy-6-(2-phenylethyl)-2H-pyran-2-one 20V, Negative-QTOF	splash10-00kb-4930000000-76868864f1222774db0e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-cis-5,6-Dihydro-5-hydroxy-4-methoxy-6-(2-phenylethyl)-2H-pyran-2-one 40V, Negative-QTOF	splash10-056u-9410000000-ef2bfe7941278461f64a	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

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

FDB000731

KNApSAcK ID

Not Available

Chemspider ID

499979

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

575067

PDB ID

Not Available

ChEBI ID

174280

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1810541

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 (+)-cis-5,6-Dihydro-5-hydroxy-4-methoxy-6-(2-phenylethyl)-2H-pyran-2-one (HMDB0029575)

MOL for HMDB0029575 ((+)-cis-5,6-Dihydro-5-hydroxy-4-methoxy-6-(2-phenylethyl)-2H-pyran-2-one)

3D MOL for HMDB0029575 ((+)-cis-5,6-Dihydro-5-hydroxy-4-methoxy-6-(2-phenylethyl)-2H-pyran-2-one)

3D SDF for HMDB0029575 ((+)-cis-5,6-Dihydro-5-hydroxy-4-methoxy-6-(2-phenylethyl)-2H-pyran-2-one)

3D-SDF for HMDB0029575 ((+)-cis-5,6-Dihydro-5-hydroxy-4-methoxy-6-(2-phenylethyl)-2H-pyran-2-one)

PDB for HMDB0029575 ((+)-cis-5,6-Dihydro-5-hydroxy-4-methoxy-6-(2-phenylethyl)-2H-pyran-2-one)

3D PDB for HMDB0029575 ((+)-cis-5,6-Dihydro-5-hydroxy-4-methoxy-6-(2-phenylethyl)-2H-pyran-2-one)

SMILES for HMDB0029575 ((+)-cis-5,6-Dihydro-5-hydroxy-4-methoxy-6-(2-phenylethyl)-2H-pyran-2-one)

INCHI for HMDB0029575 ((+)-cis-5,6-Dihydro-5-hydroxy-4-methoxy-6-(2-phenylethyl)-2H-pyran-2-one)

Structure for HMDB0029575 ((+)-cis-5,6-Dihydro-5-hydroxy-4-methoxy-6-(2-phenylethyl)-2H-pyran-2-one)

3D Structure for HMDB0029575 ((+)-cis-5,6-Dihydro-5-hydroxy-4-methoxy-6-(2-phenylethyl)-2H-pyran-2-one)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra