Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 14:03:27 UTC

Update Date

2021-09-26 23:08:48 UTC

HMDB ID

HMDB0254671

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Methysticin

Description

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. Based on a literature review very few articles have been published on Methysticin. This compound has been identified in human blood as reported by (PMID: 31557052 ). Methysticin is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Methysticin is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0254671
     RDKit          3D
Methysticin
 34 36  0  0  0  0  0  0  0  0999 V2000
   -5.3339    2.1738    0.0212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7612    1.3804   -1.0268 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8464    0.3749   -0.6647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2887   -0.8203   -0.3470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3838   -1.8855    0.0340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8006   -3.0297    0.3366 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0071   -1.5958    0.0549 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7194   -0.2177    0.3371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2218   -0.1025    0.2548 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5060   -0.9941   -0.3545 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9523   -0.8546   -0.4169 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7215   -1.8275   -1.0793 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0773   -1.7001   -1.1398 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7114   -0.6163   -0.5527 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9803    0.3459    0.0994 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5874    0.2005    0.1529 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8749    1.2925    0.5777 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0979    1.1401   -0.1498 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0572   -0.2402   -0.4628 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4046    0.6657   -0.6459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5046    2.6832    0.5452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0642    2.8681   -0.4121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7987    1.4622    0.7384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3754   -0.9728   -0.3841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0349    0.0723    1.3558 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1687    0.7720    0.7403 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0124   -1.8648   -0.8277 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2034   -2.6603   -1.5273 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7030   -2.4439   -1.6500 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0972    1.0005    0.6832 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0246    1.7053   -1.1133 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9742    1.4379    0.4279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0025    0.5256   -1.6889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2017    1.7251   -0.3713 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  3
 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

  Mrv1533004191515402D          

 20 22  0  0  0  0            999 V2000
    6.2102    6.0604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957    5.6479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957    4.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102    4.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9246    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    4.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  3  9  1  0  0  0  0
 10  8  1  4  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 15 19  1  0  0  0  0
 19 20  2  0  0  0  0
 12 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0254671

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC(=O)OC(C1)C=CC1=CC=C2OCOC2=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

> <INCHI_KEY>
GTEXBOVBADJOQH-UHFFFAOYSA-N

> <FORMULA>
C15H14O5

> <MOLECULAR_WEIGHT>
274.272

> <EXACT_MASS>
274.084123551

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
28.42405922174146

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-[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>
73.12460000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.12e-02 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0254671
     RDKit          3D
Methysticin
 34 36  0  0  0  0  0  0  0  0999 V2000
   -5.3339    2.1738    0.0212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7612    1.3804   -1.0268 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8464    0.3749   -0.6647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2887   -0.8203   -0.3470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3838   -1.8855    0.0340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8006   -3.0297    0.3366 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0071   -1.5958    0.0549 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7194   -0.2177    0.3371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2218   -0.1025    0.2548 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5060   -0.9941   -0.3545 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9523   -0.8546   -0.4169 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7215   -1.8275   -1.0793 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0773   -1.7001   -1.1398 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7114   -0.6163   -0.5527 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9803    0.3459    0.0994 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5874    0.2005    0.1529 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8749    1.2925    0.5777 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0979    1.1401   -0.1498 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0572   -0.2402   -0.4628 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4046    0.6657   -0.6459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5046    2.6832    0.5452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0642    2.8681   -0.4121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7987    1.4622    0.7384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3754   -0.9728   -0.3841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0349    0.0723    1.3558 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1687    0.7720    0.7403 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0124   -1.8648   -0.8277 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2034   -2.6603   -1.5273 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7030   -2.4439   -1.6500 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0972    1.0005    0.6832 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0246    1.7053   -1.1133 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9742    1.4379    0.4279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0025    0.5256   -1.6889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2017    1.7251   -0.3713 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  3
 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                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  C   UNK     0      11.592  11.313   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      10.259  10.543   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      10.259   9.003   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.592   8.233   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.592   6.693   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      12.926   5.923   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      10.259   5.923   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       8.925   6.693   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.925   8.233   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.591   5.923   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.591   4.383   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.126   1.597   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       2.126   4.089   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    9                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8    3                                                       
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   20                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   19                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   15   20                                                  
CONECT   20   19   12                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

COMPND    HMDB0254671
HETATM    1  C1  UNL     1      -5.334   2.174   0.021  1.00  0.00           C  
HETATM    2  O1  UNL     1      -4.761   1.380  -1.027  1.00  0.00           O  
HETATM    3  C2  UNL     1      -3.846   0.375  -0.665  1.00  0.00           C  
HETATM    4  C3  UNL     1      -4.289  -0.820  -0.347  1.00  0.00           C  
HETATM    5  C4  UNL     1      -3.384  -1.886   0.034  1.00  0.00           C  
HETATM    6  O2  UNL     1      -3.801  -3.030   0.337  1.00  0.00           O  
HETATM    7  O3  UNL     1      -2.007  -1.596   0.055  1.00  0.00           O  
HETATM    8  C5  UNL     1      -1.719  -0.218   0.337  1.00  0.00           C  
HETATM    9  C6  UNL     1      -0.222  -0.103   0.255  1.00  0.00           C  
HETATM   10  C7  UNL     1       0.506  -0.994  -0.354  1.00  0.00           C  
HETATM   11  C8  UNL     1       1.952  -0.855  -0.417  1.00  0.00           C  
HETATM   12  C9  UNL     1       2.721  -1.827  -1.079  1.00  0.00           C  
HETATM   13  C10 UNL     1       4.077  -1.700  -1.140  1.00  0.00           C  
HETATM   14  C11 UNL     1       4.711  -0.616  -0.553  1.00  0.00           C  
HETATM   15  C12 UNL     1       3.980   0.346   0.099  1.00  0.00           C  
HETATM   16  C13 UNL     1       2.587   0.201   0.153  1.00  0.00           C  
HETATM   17  O4  UNL     1       4.875   1.293   0.578  1.00  0.00           O  
HETATM   18  C14 UNL     1       6.098   1.140  -0.150  1.00  0.00           C  
HETATM   19  O5  UNL     1       6.057  -0.240  -0.463  1.00  0.00           O  
HETATM   20  C15 UNL     1      -2.405   0.666  -0.646  1.00  0.00           C  
HETATM   21  H1  UNL     1      -4.505   2.683   0.545  1.00  0.00           H  
HETATM   22  H2  UNL     1      -6.064   2.868  -0.412  1.00  0.00           H  
HETATM   23  H3  UNL     1      -5.799   1.462   0.738  1.00  0.00           H  
HETATM   24  H4  UNL     1      -5.375  -0.973  -0.384  1.00  0.00           H  
HETATM   25  H5  UNL     1      -2.035   0.072   1.356  1.00  0.00           H  
HETATM   26  H6  UNL     1       0.169   0.772   0.740  1.00  0.00           H  
HETATM   27  H7  UNL     1       0.012  -1.865  -0.828  1.00  0.00           H  
HETATM   28  H8  UNL     1       2.203  -2.660  -1.527  1.00  0.00           H  
HETATM   29  H9  UNL     1       4.703  -2.444  -1.650  1.00  0.00           H  
HETATM   30  H10 UNL     1       2.097   1.001   0.683  1.00  0.00           H  
HETATM   31  H11 UNL     1       6.025   1.705  -1.113  1.00  0.00           H  
HETATM   32  H12 UNL     1       6.974   1.438   0.428  1.00  0.00           H  
HETATM   33  H13 UNL     1      -2.002   0.526  -1.689  1.00  0.00           H  
HETATM   34  H14 UNL     1      -2.202   1.725  -0.371  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

HMDB0254671
     RDKit          3D
Methysticin
 34 36  0  0  0  0  0  0  0  0999 V2000
   -5.3339    2.1738    0.0212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7612    1.3804   -1.0268 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8464    0.3749   -0.6647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2887   -0.8203   -0.3470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3838   -1.8855    0.0340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8006   -3.0297    0.3366 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0071   -1.5958    0.0549 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7194   -0.2177    0.3371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2218   -0.1025    0.2548 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5060   -0.9941   -0.3545 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9523   -0.8546   -0.4169 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7215   -1.8275   -1.0793 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0773   -1.7001   -1.1398 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7114   -0.6163   -0.5527 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9803    0.3459    0.0994 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5874    0.2005    0.1529 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8749    1.2925    0.5777 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0979    1.1401   -0.1498 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0572   -0.2402   -0.4628 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4046    0.6657   -0.6459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5046    2.6832    0.5452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0642    2.8681   -0.4121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7987    1.4622    0.7384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3754   -0.9728   -0.3841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0349    0.0723    1.3558 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1687    0.7720    0.7403 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0124   -1.8648   -0.8277 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2034   -2.6603   -1.5273 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7030   -2.4439   -1.6500 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0972    1.0005    0.6832 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0246    1.7053   -1.1133 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9742    1.4379    0.4279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0025    0.5256   -1.6889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2017    1.7251   -0.3713 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  3
 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, ((e)-(+-))-isomer	MeSH

Chemical Formula

C₁₅H₁₄O₅

Average Molecular Weight

274.272

Monoisotopic Molecular Weight

274.084123551

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

COC1=CC(=O)OC(C1)C=CC1=CC=C2OCOC2=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

InChI Key

GTEXBOVBADJOQH-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
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

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
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	28.42 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
DeepCCS	[M+H]+	160.982	30932474
DeepCCS	[M-H]-	158.624	30932474
DeepCCS	[M-2H]-	191.51	30932474
DeepCCS	[M+Na]+	167.075	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
Methysticin	COC1=CC(=O)OC(C1)C=CC1=CC=C2OCOC2=C1	3631.5	Standard polar	33892256
Methysticin	COC1=CC(=O)OC(C1)C=CC1=CC=C2OCOC2=C1	2271.8	Standard non polar	33892256
Methysticin	COC1=CC(=O)OC(C1)C=CC1=CC=C2OCOC2=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 - Methysticin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0abd-7490000000-50765d1fc16c8aa6277e	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 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 - Methysticin 10V, Negative-QTOF	splash10-00di-0090000000-830df3f870696e821a8a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methysticin 20V, Negative-QTOF	splash10-05fs-0790000000-0a19447e5650d3d4d047	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methysticin 40V, Negative-QTOF	splash10-00kb-3900000000-238faa8b0f2cee2fe135	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methysticin 10V, Positive-QTOF	splash10-004i-0090000000-a155be011b3aa126afed	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methysticin 20V, Positive-QTOF	splash10-0a4i-0930000000-7797c07a62b16a31e9a7	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methysticin 40V, Positive-QTOF	splash10-05i9-2910000000-bfd2a9463fc9cb8af8f2	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

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

Not Available

KNApSAcK ID

C00002988

Chemspider ID

200146

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Methysticin

METLIN ID

Not Available

PubChem Compound

229851

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Methysticin (HMDB0254671)

MOL for HMDB0254671 (Methysticin)

3D MOL for HMDB0254671 (Methysticin)

3D SDF for HMDB0254671 (Methysticin)

3D-SDF for HMDB0254671 (Methysticin)

PDB for HMDB0254671 (Methysticin)

3D PDB for HMDB0254671 (Methysticin)

SMILES for HMDB0254671 (Methysticin)

INCHI for HMDB0254671 (Methysticin)

Structure for HMDB0254671 (Methysticin)

3D Structure for HMDB0254671 (Methysticin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra