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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:20:06 UTC

Update Date

2022-03-07 02:53:47 UTC

HMDB ID

HMDB0033590

Secondary Accession Numbers

HMDB33590

Metabolite Identification

Common Name

(R)-Methysticin

Description

(R)-Methysticin 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 (R)-Methysticin has been detected, but not quantified in, beverages. This could make (R)-methysticin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on (R)-Methysticin.

Structure

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

HMDB0033590
     RDKit          3D
(R)-Methysticin
 34 36  0  0  0  0  0  0  0  0999 V2000
   -5.4387    1.2853   -0.2317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4482    1.1465    0.7682 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4393    0.1771    0.6209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4932   -0.6463   -0.4066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4531   -1.6468   -0.5613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5077   -2.4411   -1.5529 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4436   -1.6925    0.3815 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0741   -0.4627    0.9652 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1070   -0.7016    2.0303 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1641   -0.6956    1.8476 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9336   -0.4798    0.6490 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5216   -0.5030   -0.6388 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3537   -0.1893   -1.7341 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6616    0.1626   -1.5294 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1125    0.1937   -0.2314 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2925   -0.1125    0.8187 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4414    0.5720   -0.3154 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7123    1.1023   -1.6082 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7031    0.5180   -2.3893 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3672    0.1350    1.6350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9690    0.3044   -0.3016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9514    1.4067   -1.2426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1016    2.1356   -0.0535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3162   -0.5634   -1.1229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8167    0.2679    0.2002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4630   -0.9034    3.0751 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7428   -0.9077    2.8017 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5471   -0.8012   -0.9536 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9961   -0.2150   -2.7491 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6859   -0.0748    1.8128 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5654    2.2169   -1.5046 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7222    0.8524   -1.9662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6209   -0.5867    2.4286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1448    1.1469    2.0032 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  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
 15 17  1  0
 17 18  1  0
 18 19  1  0
  8 20  1  0
 20  3  1  0
 16 11  1  0
 19 14  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  8 25  1  0
  9 26  1  0
 10 27  1  0
 12 28  1  0
 13 29  1  0
 16 30  1  0
 18 31  1  0
 18 32  1  0
 20 33  1  0
 20 34  1  0
M  END

  Mrv0541 05061307132D          

 20 22  0  0  0  0            999 V2000
    2.5645   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8500   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  2  2  0  0  0  0
  5  3  2  0  0  0  0
 10  2  1  0  0  0  0
 10  3  1  0  0  0  0
 10  6  2  0  0  0  0
 11  4  1  0  0  0  0
 11  7  1  0  0  0  0
 12  7  1  0  0  0  0
 12  8  2  0  0  0  0
 13  5  1  0  0  0  0
 14  6  1  0  0  0  0
 14 13  2  0  0  0  0
 15  8  1  0  0  0  0
 16 15  2  0  0  0  0
 17  1  1  0  0  0  0
 17 12  1  0  0  0  0
 18  9  1  0  0  0  0
 18 13  1  0  0  0  0
 19  9  1  0  0  0  0
 19 14  1  0  0  0  0
 20 11  1  0  0  0  0
 20 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033590

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC(=O)OC(C1)\C=C/C1=CC2=C(OCO2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H14O5/c1-17-12-7-11(20-15(16)8-12)4-2-10-3-5-13-14(6-10)19-9-18-13/h2-6,8,11H,7,9H2,1H3/b4-2-

> <INCHI_KEY>
GTEXBOVBADJOQH-RQOWECAXSA-N

> <FORMULA>
C15H14O5

> <MOLECULAR_WEIGHT>
274.2687

> <EXACT_MASS>
274.084123558

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
27.874113596531647

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-[(Z)-2-(2H-1,3-benzodioxol-5-yl)ethenyl]-4-methoxy-5,6-dihydro-2H-pyran-2-one

> <ALOGPS_LOGP>
2.06

> <JCHEM_LOGP>
2.0559451463333334

> <ALOGPS_LOGS>
-3.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.5401858771106

> <JCHEM_PKA_STRONGEST_BASIC>
-4.463083822069652

> <JCHEM_POLAR_SURFACE_AREA>
53.99000000000001

> <JCHEM_REFRACTIVITY>
73.1246

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.12e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-[(Z)-2-(2H-1,3-benzodioxol-5-yl)ethenyl]-4-methoxy-5,6-dihydropyran-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0033590
     RDKit          3D
(R)-Methysticin
 34 36  0  0  0  0  0  0  0  0999 V2000
   -5.4387    1.2853   -0.2317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4482    1.1465    0.7682 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4393    0.1771    0.6209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4932   -0.6463   -0.4066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4531   -1.6468   -0.5613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5077   -2.4411   -1.5529 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4436   -1.6925    0.3815 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0741   -0.4627    0.9652 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1070   -0.7016    2.0303 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1641   -0.6956    1.8476 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9336   -0.4798    0.6490 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5216   -0.5030   -0.6388 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3537   -0.1893   -1.7341 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6616    0.1626   -1.5294 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1125    0.1937   -0.2314 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2925   -0.1125    0.8187 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4414    0.5720   -0.3154 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7123    1.1023   -1.6082 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7031    0.5180   -2.3893 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3672    0.1350    1.6350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9690    0.3044   -0.3016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9514    1.4067   -1.2426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1016    2.1356   -0.0535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3162   -0.5634   -1.1229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8167    0.2679    0.2002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4630   -0.9034    3.0751 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7428   -0.9077    2.8017 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5471   -0.8012   -0.9536 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9961   -0.2150   -2.7491 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6859   -0.0748    1.8128 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5654    2.2169   -1.5046 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7222    0.8524   -1.9662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6209   -0.5867    2.4286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1448    1.1469    2.0032 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  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
 15 17  1  0
 17 18  1  0
 18 19  1  0
  8 20  1  0
 20  3  1  0
 16 11  1  0
 19 14  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  8 25  1  0
  9 26  1  0
 10 27  1  0
 12 28  1  0
 13 29  1  0
 16 30  1  0
 18 31  1  0
 18 32  1  0
 20 33  1  0
 20 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       4.787  -7.700   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.788  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.788  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.454  -4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.787  -4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.454   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.454  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.121  -5.390   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.787  -3.080   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       3.453  -2.310   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       6.121  -6.930   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       3.322   2.016   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       3.322  -0.476   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       6.121  -2.310   0.000  0.00  0.00           O+0
CONECT    1   17                                                            
CONECT    2    4   10                                                       
CONECT    3    5   10                                                       
CONECT    4    2   11                                                       
CONECT    5    3   13                                                       
CONECT    6   10   14                                                       
CONECT    7   11   12                                                       
CONECT    8   12   15                                                       
CONECT    9   18   19                                                       
CONECT   10    2    3    6                                                  
CONECT   11    4    7   20                                                  
CONECT   12    7    8   17                                                  
CONECT   13    5   14   18                                                  
CONECT   14    6   13   19                                                  
CONECT   15    8   16   20                                                  
CONECT   16   15                                                            
CONECT   17    1   12                                                       
CONECT   18    9   13                                                       
CONECT   19    9   14                                                       
CONECT   20   11   15                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

COMPND    HMDB0033590
HETATM    1  C1  UNL     1      -5.439   1.285  -0.232  1.00  0.00           C  
HETATM    2  O1  UNL     1      -4.448   1.147   0.768  1.00  0.00           O  
HETATM    3  C2  UNL     1      -3.439   0.177   0.621  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.493  -0.646  -0.407  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.453  -1.647  -0.561  1.00  0.00           C  
HETATM    6  O2  UNL     1      -2.508  -2.441  -1.553  1.00  0.00           O  
HETATM    7  O3  UNL     1      -1.444  -1.693   0.381  1.00  0.00           O  
HETATM    8  C5  UNL     1      -1.074  -0.463   0.965  1.00  0.00           C  
HETATM    9  C6  UNL     1      -0.107  -0.702   2.030  1.00  0.00           C  
HETATM   10  C7  UNL     1       1.164  -0.696   1.848  1.00  0.00           C  
HETATM   11  C8  UNL     1       1.934  -0.480   0.649  1.00  0.00           C  
HETATM   12  C9  UNL     1       1.522  -0.503  -0.639  1.00  0.00           C  
HETATM   13  C10 UNL     1       2.354  -0.189  -1.734  1.00  0.00           C  
HETATM   14  C11 UNL     1       3.662   0.163  -1.529  1.00  0.00           C  
HETATM   15  C12 UNL     1       4.113   0.194  -0.231  1.00  0.00           C  
HETATM   16  C13 UNL     1       3.293  -0.112   0.819  1.00  0.00           C  
HETATM   17  O4  UNL     1       5.441   0.572  -0.315  1.00  0.00           O  
HETATM   18  C14 UNL     1       5.712   1.102  -1.608  1.00  0.00           C  
HETATM   19  O5  UNL     1       4.703   0.518  -2.389  1.00  0.00           O  
HETATM   20  C15 UNL     1      -2.367   0.135   1.635  1.00  0.00           C  
HETATM   21  H1  UNL     1      -5.969   0.304  -0.302  1.00  0.00           H  
HETATM   22  H2  UNL     1      -4.951   1.407  -1.243  1.00  0.00           H  
HETATM   23  H3  UNL     1      -6.102   2.136  -0.054  1.00  0.00           H  
HETATM   24  H4  UNL     1      -4.316  -0.563  -1.123  1.00  0.00           H  
HETATM   25  H5  UNL     1      -0.817   0.268   0.200  1.00  0.00           H  
HETATM   26  H6  UNL     1      -0.463  -0.903   3.075  1.00  0.00           H  
HETATM   27  H7  UNL     1       1.743  -0.908   2.802  1.00  0.00           H  
HETATM   28  H8  UNL     1       0.547  -0.801  -0.954  1.00  0.00           H  
HETATM   29  H9  UNL     1       1.996  -0.215  -2.749  1.00  0.00           H  
HETATM   30  H10 UNL     1       3.686  -0.075   1.813  1.00  0.00           H  
HETATM   31  H11 UNL     1       5.565   2.217  -1.505  1.00  0.00           H  
HETATM   32  H12 UNL     1       6.722   0.852  -1.966  1.00  0.00           H  
HETATM   33  H13 UNL     1      -2.621  -0.587   2.429  1.00  0.00           H  
HETATM   34  H14 UNL     1      -2.145   1.147   2.003  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3
CONECT    3    4    4   20
CONECT    4    5   24
CONECT    5    6    6    7
CONECT    7    8
CONECT    8    9   20   25
CONECT    9   10   10   26
CONECT   10   11   27
CONECT   11   12   12   16
CONECT   12   13   28
CONECT   13   14   14   29
CONECT   14   15   19
CONECT   15   16   16   17
CONECT   16   30
CONECT   17   18
CONECT   18   19   31   32
CONECT   20   33   34
END

HMDB0033590
     RDKit          3D
(R)-Methysticin
 34 36  0  0  0  0  0  0  0  0999 V2000
   -5.4387    1.2853   -0.2317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4482    1.1465    0.7682 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4393    0.1771    0.6209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4932   -0.6463   -0.4066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4531   -1.6468   -0.5613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5077   -2.4411   -1.5529 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4436   -1.6925    0.3815 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0741   -0.4627    0.9652 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1070   -0.7016    2.0303 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1641   -0.6956    1.8476 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9336   -0.4798    0.6490 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5216   -0.5030   -0.6388 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3537   -0.1893   -1.7341 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6616    0.1626   -1.5294 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1125    0.1937   -0.2314 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2925   -0.1125    0.8187 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4414    0.5720   -0.3154 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7123    1.1023   -1.6082 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7031    0.5180   -2.3893 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3672    0.1350    1.6350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9690    0.3044   -0.3016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9514    1.4067   -1.2426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1016    2.1356   -0.0535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3162   -0.5634   -1.1229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8167    0.2679    0.2002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4630   -0.9034    3.0751 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7428   -0.9077    2.8017 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5471   -0.8012   -0.9536 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9961   -0.2150   -2.7491 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6859   -0.0748    1.8128 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5654    2.2169   -1.5046 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7222    0.8524   -1.9662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6209   -0.5867    2.4286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1448    1.1469    2.0032 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  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
 15 17  1  0
 17 18  1  0
 18 19  1  0
  8 20  1  0
 20  3  1  0
 16 11  1  0
 19 14  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  8 25  1  0
  9 26  1  0
 10 27  1  0
 12 28  1  0
 13 29  1  0
 16 30  1  0
 18 31  1  0
 18 32  1  0
 20 33  1  0
 20 34  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(+)-Methysticin	HMDB
Kavahin	HMDB
Kavatin	HMDB
Methysticin	HMDB
Methysticin, ((e)-(+-))-isomer	MeSH

Chemical Formula

C₁₅H₁₄O₅

Average Molecular Weight

274.2687

Monoisotopic Molecular Weight

274.084123558

IUPAC Name

6-[(Z)-2-(2H-1,3-benzodioxol-5-yl)ethenyl]-4-methoxy-5,6-dihydro-2H-pyran-2-one

Traditional Name

6-[(Z)-2-(2H-1,3-benzodioxol-5-yl)ethenyl]-4-methoxy-5,6-dihydropyran-2-one

CAS Registry Number

495-85-2

SMILES

COC1=CC(=O)OC(C1)\C=C/C1=CC2=C(OCO2)C=C1

InChI Identifier

InChI=1S/C15H14O5/c1-17-12-7-11(20-15(16)8-12)4-2-10-3-5-13-14(6-10)19-9-18-13/h2-6,8,11H,7,9H2,1H3/b4-2-

InChI Key

GTEXBOVBADJOQH-RQOWECAXSA-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
Benzodioxole
Styrene
Dihydropyranone
Pyran
Benzenoid
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Vinylogous ester
Lactone
Carboxylic acid ester
Organoheterocyclic compound
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Acetal
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0033590)
Cytoplasm (HMDB: HMDB0033590)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033590)

Source

Exogenous

Exogenous (HMDB: HMDB0033590)

Food

Food (HMDB: HMDB0033590)

Beverage

Beverages (FooDB: FOOD00870)

Endogenous

Plant

Plant (HMDB: HMDB0033590)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0033590)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	139 - 140.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	582 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	0.091 g/L	ALOGPS
logP	2.06	ALOGPS
logP	2.06	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	16.54	ChemAxon
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	53.99 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	73.12 m³·mol⁻¹	ChemAxon
Polarizability	27.87 Å³	ChemAxon
Number of Rings	3	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]+	167.188	31661259
DarkChem	[M-H]-	167.849	31661259
DeepCCS	[M+H]+	163.115	30932474
DeepCCS	[M-H]-	160.757	30932474
DeepCCS	[M-2H]-	193.643	30932474
DeepCCS	[M+Na]+	169.208	30932474
AllCCS	[M+H]+	164.3	32859911
AllCCS	[M+H-H2O]+	160.4	32859911
AllCCS	[M+NH4]+	168.0	32859911
AllCCS	[M+Na]+	169.0	32859911
AllCCS	[M-H]-	166.4	32859911
AllCCS	[M+Na-2H]-	166.1	32859911
AllCCS	[M+HCOO]-	165.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(R)-Methysticin	COC1=CC(=O)OC(C1)\C=C/C1=CC2=C(OCO2)C=C1	3631.6	Standard polar	33892256
(R)-Methysticin	COC1=CC(=O)OC(C1)\C=C/C1=CC2=C(OCO2)C=C1	2272.0	Standard non polar	33892256
(R)-Methysticin	COC1=CC(=O)OC(C1)\C=C/C1=CC2=C(OCO2)C=C1	2677.6	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 - (R)-Methysticin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0abd-7490000000-72892e7864dc2a72999b	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (R)-Methysticin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (R)-Methysticin 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 - (R)-Methysticin 10V, Positive-QTOF	splash10-004i-0290000000-13ebecd9a1f55b4739a0	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Methysticin 20V, Positive-QTOF	splash10-0ab9-1920000000-c672d5d970f5295e76e1	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Methysticin 40V, Positive-QTOF	splash10-05bk-4900000000-8b1043ebac3cf227dbdb	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Methysticin 10V, Negative-QTOF	splash10-00di-0090000000-efe53ec92151590e2a9c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Methysticin 20V, Negative-QTOF	splash10-0596-9080000000-265e5bf28a5cffd97044	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Methysticin 40V, Negative-QTOF	splash10-052f-9720000000-87a807978972f7d8c4f7	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Methysticin 10V, Positive-QTOF	splash10-004i-0090000000-04aa467c9fe1c92abd24	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Methysticin 20V, Positive-QTOF	splash10-0a4i-0930000000-dde9cb897d50e2b4a650	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Methysticin 40V, Positive-QTOF	splash10-05fr-1910000000-50654eb11f4f3ec08adc	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Methysticin 10V, Negative-QTOF	splash10-00di-0090000000-def54e58643176e2f5a2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Methysticin 20V, Negative-QTOF	splash10-006t-0890000000-6b857fddde7856c1895f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Methysticin 40V, Negative-QTOF	splash10-00kb-5900000000-43e7200c25846ca880a7	2021-09-22	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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

90125683

PDB ID

Not Available

ChEBI ID

174607

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1533241

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Matsuda H, Hirata N, Kawaguchi Y, Naruto S, Takata T, Oyama M, Iinuma M, Kubo M: Melanogenesis stimulation in murine B16 melanoma cells by Kava (Piper methysticum) rhizome extract and kavalactones. Biol Pharm Bull. 2006 Apr;29(4):834-7. [PubMed:16595931 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for (R)-Methysticin (HMDB0033590)

MOL for HMDB0033590 ((R)-Methysticin)

3D MOL for HMDB0033590 ((R)-Methysticin)

3D SDF for HMDB0033590 ((R)-Methysticin)

3D-SDF for HMDB0033590 ((R)-Methysticin)

PDB for HMDB0033590 ((R)-Methysticin)

3D PDB for HMDB0033590 ((R)-Methysticin)

SMILES for HMDB0033590 ((R)-Methysticin)

INCHI for HMDB0033590 ((R)-Methysticin)

Structure for HMDB0033590 ((R)-Methysticin)

3D Structure for HMDB0033590 ((R)-Methysticin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra