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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:30:48 UTC

Update Date

2022-03-07 02:52:11 UTC

HMDB ID

HMDB0029504

Secondary Accession Numbers

HMDB29504

Metabolite Identification

Common Name

Marindinin

Description

Marindinin, also known as 7,8-dihydrokavain, 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 a significant number of articles have been published on Marindinin.

Structure

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

HMDB0029504
     RDKit          3D
Marindinin
 33 34  0  0  0  0  0  0  0  0999 V2000
    4.6053    1.7658   -0.7807 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3253    1.2720   -1.0202 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6376    0.4631   -0.0999 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3108    0.0755    0.9583 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6788   -0.7533    1.9454 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3775   -1.0951    2.9438 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3719   -1.1377    1.7782 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5273   -0.6009    0.7632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2897   -1.7664    0.2817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2857   -1.4908   -0.7735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3561   -0.5345   -0.4197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3530    0.8139   -0.6687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3934    1.6474   -0.2919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4879    1.1323    0.3593 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5147   -0.2011    0.6170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4928   -1.0151    0.2463 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2501    0.0918   -0.3364 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3770    0.9796   -0.6225 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6287    2.4002    0.1500 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9390    2.3714   -1.6282 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3636    0.4097    1.0518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1834    0.0859    1.3092 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4387   -2.5151   -0.1355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7401   -2.2534    1.1746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7326   -1.1498   -1.6883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7234   -2.4888   -1.0858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5202    1.2344   -1.1814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3839    2.7086   -0.4910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3276    1.7590    0.6718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3841   -0.6065    1.1333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5225   -2.0886    0.4579 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1585   -0.5694   -1.2495 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7011    1.0561   -0.5247 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  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
  9 24  1  0
 10 25  1  0
 10 26  1  0
 12 27  1  0
 13 28  1  0
 14 29  1  0
 15 30  1  0
 16 31  1  0
 17 32  1  0
 17 33  1  0
M  END

  Mrv0541 05061304472D          

 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  1  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>
HMDB0029504

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC(=O)OC(CCC2=CC=CC=C2)C1

> <INCHI_IDENTIFIER>
InChI=1S/C14H16O3/c1-16-13-9-12(17-14(15)10-13)8-7-11-5-3-2-4-6-11/h2-6,10,12H,7-9H2,1H3

> <INCHI_KEY>
VOOYTQRREPYRIW-UHFFFAOYSA-N

> <FORMULA>
C14H16O3

> <MOLECULAR_WEIGHT>
232.275

> <EXACT_MASS>
232.109944378

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
25.348828234314254

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.91

> <JCHEM_LOGP>
2.5560258753333334

> <ALOGPS_LOGS>
-3.75

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.426439906948723

> <JCHEM_PKA_STRONGEST_BASIC>
-4.787811443531041

> <JCHEM_POLAR_SURFACE_AREA>
35.53

> <JCHEM_REFRACTIVITY>
66.39510000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.13e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
dihydrokavain

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0029504
     RDKit          3D
Marindinin
 33 34  0  0  0  0  0  0  0  0999 V2000
    4.6053    1.7658   -0.7807 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3253    1.2720   -1.0202 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6376    0.4631   -0.0999 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3108    0.0755    0.9583 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6788   -0.7533    1.9454 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3775   -1.0951    2.9438 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3719   -1.1377    1.7782 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5273   -0.6009    0.7632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2897   -1.7664    0.2817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2857   -1.4908   -0.7735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3561   -0.5345   -0.4197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3530    0.8139   -0.6687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3934    1.6474   -0.2919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4879    1.1323    0.3593 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5147   -0.2011    0.6170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4928   -1.0151    0.2463 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2501    0.0918   -0.3364 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3770    0.9796   -0.6225 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6287    2.4002    0.1500 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9390    2.3714   -1.6282 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3636    0.4097    1.0518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1834    0.0859    1.3092 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4387   -2.5151   -0.1355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7401   -2.2534    1.1746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7326   -1.1498   -1.6883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7234   -2.4888   -1.0858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5202    1.2344   -1.1814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3839    2.7086   -0.4910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3276    1.7590    0.6718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3841   -0.6065    1.1333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5225   -2.0886    0.4579 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1585   -0.5694   -1.2495 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7011    1.0561   -0.5247 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  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
  9 24  1  0
 10 25  1  0
 10 26  1  0
 12 27  1  0
 13 28  1  0
 14 29  1  0
 15 30  1  0
 16 31  1  0
 17 32  1  0
 17 33  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -1.334   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    HMDB0029504
HETATM    1  C1  UNL     1       4.605   1.766  -0.781  1.00  0.00           C  
HETATM    2  O1  UNL     1       3.325   1.272  -1.020  1.00  0.00           O  
HETATM    3  C2  UNL     1       2.638   0.463  -0.100  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.311   0.076   0.958  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.679  -0.753   1.945  1.00  0.00           C  
HETATM    6  O2  UNL     1       3.377  -1.095   2.944  1.00  0.00           O  
HETATM    7  O3  UNL     1       1.372  -1.138   1.778  1.00  0.00           O  
HETATM    8  C5  UNL     1       0.527  -0.601   0.763  1.00  0.00           C  
HETATM    9  C6  UNL     1      -0.290  -1.766   0.282  1.00  0.00           C  
HETATM   10  C7  UNL     1      -1.286  -1.491  -0.774  1.00  0.00           C  
HETATM   11  C8  UNL     1      -2.356  -0.534  -0.420  1.00  0.00           C  
HETATM   12  C9  UNL     1      -2.353   0.814  -0.669  1.00  0.00           C  
HETATM   13  C10 UNL     1      -3.393   1.647  -0.292  1.00  0.00           C  
HETATM   14  C11 UNL     1      -4.488   1.132   0.359  1.00  0.00           C  
HETATM   15  C12 UNL     1      -4.515  -0.201   0.617  1.00  0.00           C  
HETATM   16  C13 UNL     1      -3.493  -1.015   0.246  1.00  0.00           C  
HETATM   17  C14 UNL     1       1.250   0.092  -0.336  1.00  0.00           C  
HETATM   18  H1  UNL     1       5.377   0.980  -0.623  1.00  0.00           H  
HETATM   19  H2  UNL     1       4.629   2.400   0.150  1.00  0.00           H  
HETATM   20  H3  UNL     1       4.939   2.371  -1.628  1.00  0.00           H  
HETATM   21  H4  UNL     1       4.364   0.410   1.052  1.00  0.00           H  
HETATM   22  H5  UNL     1      -0.183   0.086   1.309  1.00  0.00           H  
HETATM   23  H6  UNL     1       0.439  -2.515  -0.136  1.00  0.00           H  
HETATM   24  H7  UNL     1      -0.740  -2.253   1.175  1.00  0.00           H  
HETATM   25  H8  UNL     1      -0.733  -1.150  -1.688  1.00  0.00           H  
HETATM   26  H9  UNL     1      -1.723  -2.489  -1.086  1.00  0.00           H  
HETATM   27  H10 UNL     1      -1.520   1.234  -1.181  1.00  0.00           H  
HETATM   28  H11 UNL     1      -3.384   2.709  -0.491  1.00  0.00           H  
HETATM   29  H12 UNL     1      -5.328   1.759   0.672  1.00  0.00           H  
HETATM   30  H13 UNL     1      -5.384  -0.606   1.133  1.00  0.00           H  
HETATM   31  H14 UNL     1      -3.523  -2.089   0.458  1.00  0.00           H  
HETATM   32  H15 UNL     1       1.158  -0.569  -1.250  1.00  0.00           H  
HETATM   33  H16 UNL     1       0.701   1.056  -0.525  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   23   24
CONECT   10   11   25   26
CONECT   11   12   12   16
CONECT   12   13   27
CONECT   13   14   14   28
CONECT   14   15   29
CONECT   15   16   16   30
CONECT   16   31
CONECT   17   32   33
END

HMDB0029504
     RDKit          3D
Marindinin
 33 34  0  0  0  0  0  0  0  0999 V2000
    4.6053    1.7658   -0.7807 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3253    1.2720   -1.0202 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6376    0.4631   -0.0999 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3108    0.0755    0.9583 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6788   -0.7533    1.9454 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3775   -1.0951    2.9438 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3719   -1.1377    1.7782 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5273   -0.6009    0.7632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2897   -1.7664    0.2817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2857   -1.4908   -0.7735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3561   -0.5345   -0.4197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3530    0.8139   -0.6687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3934    1.6474   -0.2919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4879    1.1323    0.3593 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5147   -0.2011    0.6170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4928   -1.0151    0.2463 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2501    0.0918   -0.3364 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3770    0.9796   -0.6225 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6287    2.4002    0.1500 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9390    2.3714   -1.6282 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3636    0.4097    1.0518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1834    0.0859    1.3092 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4387   -2.5151   -0.1355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7401   -2.2534    1.1746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7326   -1.1498   -1.6883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7234   -2.4888   -1.0858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5202    1.2344   -1.1814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3839    2.7086   -0.4910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3276    1.7590    0.6718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3841   -0.6065    1.1333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5225   -2.0886    0.4579 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1585   -0.5694   -1.2495 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7011    1.0561   -0.5247 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  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
  9 24  1  0
 10 25  1  0
 10 26  1  0
 12 27  1  0
 13 28  1  0
 14 29  1  0
 15 30  1  0
 16 31  1  0
 17 32  1  0
 17 33  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-Methoxy-6-(2-phenylethyl)-5,6-dihydro-2H-pyran-2-one	HMDB
5,6-Dihydro-4-methoxy-6-phenethyl-2H-pyran-2-one	HMDB
7,8-Dihydro-kawain	HMDB
7,8-Dihydrokavain	HMDB
7,8-Dihydrokawain	HMDB
Dihydro-kavain	HMDB
Dihydro-kawain	HMDB
Dihydrokavain	HMDB
Dihydrokawain	HMDB

Chemical Formula

C₁₄H₁₆O₃

Average Molecular Weight

232.275

Monoisotopic Molecular Weight

232.109944378

IUPAC Name

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

Traditional Name

dihydrokavain

CAS Registry Number

587-63-3

SMILES

COC1=CC(=O)OC(CCC2=CC=CC=C2)C1

InChI Identifier

InChI=1S/C14H16O3/c1-16-13-9-12(17-14(15)10-13)8-7-11-5-3-2-4-6-11/h2-6,10,12H,7-9H2,1H3

InChI Key

VOOYTQRREPYRIW-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
Vinylogous ester
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Lactone
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Carbonyl group
Organooxygen compound
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0029504)
Cell membrane (HMDB: HMDB0029504)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0029504)

Source

Endogenous

Endogenous (HMDB: HMDB0029504)

Plant

Plant (HMDB: HMDB0029504)

Exogenous

Food

Food (HMDB: HMDB0029504)

Beverage

Beverages (FooDB: FOOD00870)

Exogenous (HMDB: HMDB0029504)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	56 - 60 °C	Not Available
Boiling Point	413.60 °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	1.950 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.041 g/L	ALOGPS
logP	2.91	ALOGPS
logP	2.56	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	16.43	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	4	ChemAxon
Refractivity	66.4 m³·mol⁻¹	ChemAxon
Polarizability	25.35 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]+	155.985	31661259
DarkChem	[M-H]-	156.762	31661259
DeepCCS	[M+H]+	151.732	30932474
DeepCCS	[M-H]-	149.374	30932474
DeepCCS	[M-2H]-	182.984	30932474
DeepCCS	[M+Na]+	157.996	30932474
AllCCS	[M+H]+	154.8	32859911
AllCCS	[M+H-H2O]+	150.6	32859911
AllCCS	[M+NH4]+	158.7	32859911
AllCCS	[M+Na]+	159.8	32859911
AllCCS	[M-H]-	158.2	32859911
AllCCS	[M+Na-2H]-	158.4	32859911
AllCCS	[M+HCOO]-	158.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Marindinin	COC1=CC(=O)OC(CCC2=CC=CC=C2)C1	3000.7	Standard polar	33892256
Marindinin	COC1=CC(=O)OC(CCC2=CC=CC=C2)C1	1970.6	Standard non polar	33892256
Marindinin	COC1=CC(=O)OC(CCC2=CC=CC=C2)C1	2174.2	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 - Marindinin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9500000000-c5600c77821baced5710	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Marindinin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Marindinin 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 - Marindinin 10V, Positive-QTOF	splash10-001i-0590000000-cdb149e3549ebc48df46	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Marindinin 20V, Positive-QTOF	splash10-0159-1900000000-5f9a595ba9bd7424a337	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Marindinin 40V, Positive-QTOF	splash10-0kvo-9800000000-26a9688f8a322373262e	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Marindinin 10V, Negative-QTOF	splash10-001i-0690000000-1a1d0e9cea6a50a7b0d4	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Marindinin 20V, Negative-QTOF	splash10-000x-9440000000-113393a90e3c0732dd4d	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Marindinin 40V, Negative-QTOF	splash10-0536-9600000000-9fba2cac2d065519983c	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Marindinin 10V, Negative-QTOF	splash10-0a4i-0900000000-4e868adf7649a278b06c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Marindinin 20V, Negative-QTOF	splash10-0a4i-0900000000-da558f14842069aee8f2	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Marindinin 40V, Negative-QTOF	splash10-004i-9200000000-6e26bb77b8bdc63aebda	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Marindinin 10V, Positive-QTOF	splash10-0159-1960000000-1c868b5a6476e7791710	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Marindinin 20V, Positive-QTOF	splash10-00kf-7900000000-69a5b13079ddea7eefc6	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Marindinin 40V, Positive-QTOF	splash10-00mo-9500000000-737b2befa46a626ef81c	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

FDB000639

KNApSAcK ID

C00029583

Chemspider ID

88817

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Dihydrokavain

METLIN ID

Not Available

PubChem Compound

98356

PDB ID

Not Available

ChEBI ID

862793

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1396961

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Backhauss C, Krieglstein J: Extract of kava (Piper methysticum) and its methysticin constituents protect brain tissue against ischemic damage in rodents. Eur J Pharmacol. 1992 May 14;215(2-3):265-9. [PubMed:1396990 ]
Boonen G, Haberlein H: Influence of genuine kavapyrone enantiomers on the GABA-A binding site. Planta Med. 1998 Aug;64(6):504-6. [PubMed:9776662 ]
Hu L, Jhoo JW, Ang CY, Dinovi M, Mattia A: Determination of six kavalactones in dietary supplements and selected functional foods containing Piper methysticum by isocratic liquid chromatography with internal standard. J AOAC Int. 2005 Jan-Feb;88(1):16-25. [PubMed:15759721 ]
de Jager LS, Perfetti GA, Diachenko GW: LC-UV and LC-MS analysis of food and drink products containing kava. Food Addit Contam. 2004 Oct;21(10):921-34. [PubMed:15712517 ]
Weiss J, Sauer A, Frank A, Unger M: Extracts and kavalactones of Piper methysticum G. Forst (kava-kava) inhibit P-glycoprotein in vitro. Drug Metab Dispos. 2005 Nov;33(11):1580-3. Epub 2005 Jul 28. [PubMed:16051732 ]
Kato K, Motodate S, Mochida T, Kobayashi T, Akita H: Intermolecular methoxycarbonylation of terminal alkynes catalyzed by palladium(II) bis(oxazoline) complexes. Angew Chem Int Ed Engl. 2009;48(18):3326-8. doi: 10.1002/anie.200806080. [PubMed:19191366 ]
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 ]
Du H, Zhao D, Ding K: Enantioselective catalysis of the hetero-Diels-Alder reaction between Brassard's diene and aldehydes by hydrogen-bonding activation: a one-step synthesis of (S)-(+)-dihydrokawain. Chemistry. 2004 Nov 19;10(23):5964-70. [PubMed:15487027 ]
Herath W, Ferreira D, Mikell JR, Khan IA: Microbial metabolism. Part 5. Dihydrokawain. Chem Pharm Bull (Tokyo). 2004 Nov;52(11):1372-4. [PubMed:15516767 ]
Uebelhack R, Franke L, Schewe HJ: Inhibition of platelet MAO-B by kava pyrone-enriched extract from Piper methysticum Forster (kava-kava). Pharmacopsychiatry. 1998 Sep;31(5):187-92. [PubMed:9832350 ]
Jamieson DD, Duffield PH: The antinociceptive actions of kava components in mice. Clin Exp Pharmacol Physiol. 1990 Jul;17(7):495-507. [PubMed:2401103 ]
Bobeldijk I, Boonzaaijer G, Spies-Faber EJ, Vaes WH: Determination of kava lactones in food supplements by liquid chromatography-atmospheric pressure chemical ionisation tandem mass spectrometry. J Chromatogr A. 2005 Mar 4;1067(1-2):107-14. [PubMed:15844515 ]
Li Y, Mei H, Wu Q, Zhang S, Fang JL, Shi L, Guo L: Methysticin and 7,8-dihydromethysticin are two major kavalactones in kava extract to induce CYP1A1. Toxicol Sci. 2011 Dec;124(2):388-99. doi: 10.1093/toxsci/kfr235. Epub 2011 Sep 9. [PubMed:21908763 ]
Wu D, Yu L, Nair MG, DeWitt DL, Ramsewak RS: Cyclooxygenase enzyme inhibitory compounds with antioxidant activities from Piper methysticum (kava kava) roots. Phytomedicine. 2002 Jan;9(1):41-7. [PubMed:11924763 ]
Folmer F, Blasius R, Morceau F, Tabudravu J, Dicato M, Jaspars M, Diederich M: Inhibition of TNFalpha-induced activation of nuclear factor kappaB by kava (Piper methysticum) derivatives. Biochem Pharmacol. 2006 Apr 14;71(8):1206-18. Epub 2006 Feb 7. [PubMed:16464438 ]
Baum SS, Hill R, Rommelspacher H: Effect of kava extract and individual kavapyrones on neurotransmitter levels in the nucleus accumbens of rats. Prog Neuropsychopharmacol Biol Psychiatry. 1998 Oct;22(7):1105-20. [PubMed:9829291 ]
Otoguro K, Iwatsuki M, Ishiyama A, Namatame M, Nishihara-Tsukashima A, Kiyohara H, Hashimoto T, Asakawa Y, Omura S, Yamada H: In vitro antitrypanosomal activity of some phenolic compounds from propolis and lactones from Fijian Kawa (Piper methysticum). J Nat Med. 2012 Jul;66(3):558-61. doi: 10.1007/s11418-011-0613-z. Epub 2011 Nov 25. [PubMed:22116743 ]
Ma Y, Sachdeva K, Liu J, Ford M, Yang D, Khan IA, Chichester CO, Yan B: Desmethoxyyangonin and dihydromethysticin are two major pharmacological kavalactones with marked activity on the induction of CYP3A23. Drug Metab Dispos. 2004 Nov;32(11):1317-24. Epub 2004 Jul 28. [PubMed:15282211 ]
Hashimoto T, Suganuma M, Fujiki H, Yamada M, Kohno T, Asakawa Y: Isolation and synthesis of TNF-alpha release inhibitors from Fijian kawa (Piper methysticum). Phytomedicine. 2003 May;10(4):309-17. [PubMed:12809361 ]
Feltenstein MW, Lambdin LC, Ganzera M, Ranjith H, Dharmaratne W, Nanayakkara NP, Khan IA, Sufka KJ: Anxiolytic properties of Piper methysticum extract samples and fractions in the chick social-separation-stress procedure. Phytother Res. 2003 Mar;17(3):210-6. [PubMed:12672148 ]
Xuan TD, Elzaawely AA, Fukuta M, Tawata S: Herbicidal and Fungicidal Activities of Lactones in Kava (Piper methysticum). J Agric Food Chem. 2006 Feb 8;54(3):720-5. [PubMed:16448174 ]
Arai Y, Masuda T, Yoneda S, Masaki Y, Shiro M: Asymmetric synthesis of (+)-dihydrokawain-5-ol. J Org Chem. 2000 Jan 14;65(1):258-62. [PubMed:10813926 ]
Yuan CS, Dey L, Wang A, Mehendale S, Xie JT, Aung HH, Ang-Lee MK: Kavalactones and dihydrokavain modulate GABAergic activity in a rat gastric-brainstem preparation. Planta Med. 2002 Dec;68(12):1092-6. [PubMed:12494336 ]
Teschke R, Lebot V: Proposal for a kava quality standardization code. Food Chem Toxicol. 2011 Oct;49(10):2503-16. doi: 10.1016/j.fct.2011.06.075. Epub 2011 Jul 3. [PubMed:21756963 ]
Xuan TD, Chung IM, Khanh TD, Tawata S: Identification of phytotoxic substances from early growth of barnyard grass (Echinochloa crusgalli) root exudates. J Chem Ecol. 2006 Apr;32(4):895-906. Epub 2006 May 5. [PubMed:16718576 ]
Whittaker P, Clarke JJ, San RH, Betz JM, Seifried HE, de Jager LS, Dunkel VC: Evaluation of commercial kava extracts and kavalactone standards for mutagenicity and toxicity using the mammalian cell gene mutation assay in L5178Y mouse lymphoma cells. Food Chem Toxicol. 2008 Jan;46(1):168-74. Epub 2007 Jul 31. [PubMed:17822821 ]
Keledjian J, Duffield PH, Jamieson DD, Lidgard RO, Duffield AM: Uptake into mouse brain of four compounds present in the psychoactive beverage kava. J Pharm Sci. 1988 Dec;77(12):1003-6. [PubMed:3244102 ]
Pescitelli G, Bilia AR, Bergonzi MC, Vincieri FF, Di Bari L: Cyclodextrins as carriers for kavalactones in aqueous media: spectroscopic characterization of (S)-7,8-dihydrokavain and beta-cyclodextrin inclusion complex. J Pharm Biomed Anal. 2010 Aug 1;52(4):479-83. doi: 10.1016/j.jpba.2010.01.037. Epub 2010 Feb 1. [PubMed:20185265 ]
Rasmussen AK, Scheline RR, Solheim E, Hansel R: Metabolism of some kava pyrones in the rat. Xenobiotica. 1979 Jan;9(1):1-16. [PubMed:760318 ]
Warburton E, Bristow T: Fourier transform ion cyclotron resonance mass spectrometry for the characterisation of kavalactones in the kava plant: elemental formulae confirmation by dual spray accurate mass measurement and structural confirmation by infrared multiphoton dissociation and sustained off-resonance irradiation collision induced dissociation. Eur J Mass Spectrom (Chichester). 2006;12(4):223-33. [PubMed:17057279 ]
Tarbah F, Mahler H, Kardel B, Weinmann W, Hafner D, Daldrup T: Kinetics of kavain and its metabolites after oral application. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jun 5;789(1):115-30. [PubMed:12726850 ]
Haberlein H, Boonen G, Beck MA: Piper methysticum: enantiomeric separation of kavapyrones by high performance liquid chromatography. Planta Med. 1997 Feb;63(1):63-5. [PubMed:17252330 ]
Johnson BM, Qiu SX, Zhang S, Zhang F, Burdette JE, Yu L, Bolton JL, van Breemen RB: Identification of novel electrophilic metabolites of piper methysticum Forst (Kava). Chem Res Toxicol. 2003 Jun;16(6):733-40. [PubMed:12807356 ]
Singh RP, Singh VK: Facile one-step synthesis of beta-alkoxy lactone via sequential lactonization and 1,4-addition of alkoxide group: total synthesis of all stereoisomers of dihydrokawain-5-ol. J Org Chem. 2004 May 14;69(10):3425-30. [PubMed:15132552 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Marindinin (HMDB0029504)

MOL for HMDB0029504 (Marindinin)

3D MOL for HMDB0029504 (Marindinin)

3D SDF for HMDB0029504 (Marindinin)

3D-SDF for HMDB0029504 (Marindinin)

PDB for HMDB0029504 (Marindinin)

3D PDB for HMDB0029504 (Marindinin)

SMILES for HMDB0029504 (Marindinin)

INCHI for HMDB0029504 (Marindinin)

Structure for HMDB0029504 (Marindinin)

3D Structure for HMDB0029504 (Marindinin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra