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Showing metabocard for Marindinin (HMDB0029504)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:30:48 UTC
Update Date2022-03-07 02:52:11 UTC
HMDB IDHMDB0029504
Secondary Accession Numbers
  • HMDB29504
Metabolite Identification
Common NameMarindinin
DescriptionMarindinin, 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
Data?1582753428
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0029504 (Marindinin)


  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
Download

3D MOL for HMDB0029504 (Marindinin)

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
Download

3D SDF for HMDB0029504 (Marindinin)


  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

$$$$
Download

3D-SDF for HMDB0029504 (Marindinin)

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
Download

PDB for HMDB0029504 (Marindinin)

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
Download

3D PDB for HMDB0029504 (Marindinin)

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
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SMILES for HMDB0029504 (Marindinin)

COC1=CC(=O)OC(CCC2=CC=CC=C2)C1
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INCHI for HMDB0029504 (Marindinin)

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
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View in JSmolView Stereo Labels
Synonyms
ValueSource
4-Methoxy-6-(2-phenylethyl)-5,6-dihydro-2H-pyran-2-oneHMDB
5,6-Dihydro-4-methoxy-6-phenethyl-2H-pyran-2-oneHMDB
7,8-Dihydro-kawainHMDB
7,8-DihydrokavainHMDB
7,8-DihydrokawainHMDB
Dihydro-kavainHMDB
Dihydro-kawainHMDB
DihydrokavainHMDB
DihydrokawainHMDB
Chemical FormulaC14H16O3
Average Molecular Weight232.275
Monoisotopic Molecular Weight232.109944378
IUPAC Name4-methoxy-6-(2-phenylethyl)-5,6-dihydro-2H-pyran-2-one
Traditional Namedihydrokavain
CAS Registry Number587-63-3
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 KeyVOOYTQRREPYRIW-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.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassKavalactones
Sub ClassNot Available
Direct ParentKavalactones
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 FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point56 - 60 °CNot Available
Boiling Point413.60 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility1154 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP1.950 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.041 g/LALOGPS
logP2.91ALOGPS
logP2.56ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)16.43ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area35.53 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity66.4 m³·mol⁻¹ChemAxon
Polarizability25.35 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+155.98531661259
DarkChem[M-H]-156.76231661259
DeepCCS[M+H]+151.73230932474
DeepCCS[M-H]-149.37430932474
DeepCCS[M-2H]-182.98430932474
DeepCCS[M+Na]+157.99630932474
AllCCS[M+H]+154.832859911
AllCCS[M+H-H2O]+150.632859911
AllCCS[M+NH4]+158.732859911
AllCCS[M+Na]+159.832859911
AllCCS[M-H]-158.232859911
AllCCS[M+Na-2H]-158.432859911
AllCCS[M+HCOO]-158.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
MarindininCOC1=CC(=O)OC(CCC2=CC=CC=C2)C13000.7Standard polar33892256
MarindininCOC1=CC(=O)OC(CCC2=CC=CC=C2)C11970.6Standard non polar33892256
MarindininCOC1=CC(=O)OC(CCC2=CC=CC=C2)C12174.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Marindinin GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9500000000-c5600c77821baced57102017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Marindinin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Marindinin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Marindinin 10V, Positive-QTOFsplash10-001i-0590000000-cdb149e3549ebc48df462015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Marindinin 20V, Positive-QTOFsplash10-0159-1900000000-5f9a595ba9bd7424a3372015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Marindinin 40V, Positive-QTOFsplash10-0kvo-9800000000-26a9688f8a322373262e2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Marindinin 10V, Negative-QTOFsplash10-001i-0690000000-1a1d0e9cea6a50a7b0d42015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Marindinin 20V, Negative-QTOFsplash10-000x-9440000000-113393a90e3c0732dd4d2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Marindinin 40V, Negative-QTOFsplash10-0536-9600000000-9fba2cac2d065519983c2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Marindinin 10V, Negative-QTOFsplash10-0a4i-0900000000-4e868adf7649a278b06c2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Marindinin 20V, Negative-QTOFsplash10-0a4i-0900000000-da558f14842069aee8f22021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Marindinin 40V, Negative-QTOFsplash10-004i-9200000000-6e26bb77b8bdc63aebda2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Marindinin 10V, Positive-QTOFsplash10-0159-1960000000-1c868b5a6476e77917102021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Marindinin 20V, Positive-QTOFsplash10-00kf-7900000000-69a5b13079ddea7eefc62021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Marindinin 40V, Positive-QTOFsplash10-00mo-9500000000-737b2befa46a626ef81c2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB000639
KNApSAcK IDC00029583
Chemspider ID88817
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDihydrokavain
METLIN IDNot Available
PubChem Compound98356
PDB IDNot Available
ChEBI ID862793
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1396961
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. 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 ]
  7. 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 ]
  8. 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 ]
  9. 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 ]
  10. 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 ]
  11. Jamieson DD, Duffield PH: The antinociceptive actions of kava components in mice. Clin Exp Pharmacol Physiol. 1990 Jul;17(7):495-507. [PubMed:2401103 ]
  12. 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 ]
  13. 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 ]
  14. 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 ]
  15. 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 ]
  16. 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 ]
  17. 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 ]
  18. 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 ]
  19. 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 ]
  20. 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 ]
  21. 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 ]
  22. 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 ]
  23. 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 ]
  24. 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 ]
  25. 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 ]
  26. 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 ]
  27. 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 ]
  28. 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 ]
  29. 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 ]
  30. 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 ]
  31. 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 ]
  32. 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 ]
  33. 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 ]
  34. 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 ]
  35. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .