MiMeDB: Showing metabocard for Dihydromethysticin (MMDBc0053087)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-05-16 21:13:56 UTC

Update Date

2024-04-30 20:45:58 UTC

Metabolite ID

MMDBc0053087

Metabolite Identification

Common Name

Dihydromethysticin

Description

Dihydromethysticin is found in beverages. Dihydromethysticin is isolated from Piper methysticum (kava). FDA advises against use of kava in food due to potential risk of severe liver damage (2002) Dihydromethysticin is one of the six major kavalactones found in the kava plant

Structure

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

HMDB0030791
     RDKit          3D
Dihydromethysticin
 36 38  0  0  0  0  0  0  0  0999 V2000
    5.3192    2.1596   -0.1698 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5049    1.5611    0.8038 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7375    0.4491    0.5142 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2877   -0.7287    0.3306 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4907   -1.9205    0.0244 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0089   -3.0459   -0.1541 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1097   -1.7166   -0.0559 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6213   -0.6891    0.8162 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1324   -0.6972    0.7215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3887   -0.4341   -0.6646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8655   -0.4769   -0.5970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5685   -1.6345   -0.7881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9565   -1.6781   -0.7253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6131   -0.4983   -0.4599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9323    0.7072   -0.2582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5500    0.6852   -0.3337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8990    1.6742   -0.0187 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0969    1.1871   -0.5489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9831   -0.2093   -0.3327 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2755    0.5969    0.4094 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6719    2.4878   -1.0047 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7958    3.0493    0.3012 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0697    1.4147   -0.5236 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3839   -0.7934    0.4153 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9041   -0.8842    1.8723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3353    0.0545    1.3919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2224   -1.6940    1.0246 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0087   -1.1563   -1.4117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0235    0.5639   -0.9933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0566   -2.5768   -0.9995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5015   -2.5923   -0.8767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0380    1.6338   -0.1738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1567    1.3945   -1.6393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9985    1.5339    0.0013 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9023    1.4667    0.9897 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9619    0.8068   -0.6510 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
 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
  9 27  1  0
 10 28  1  0
 10 29  1  0
 12 30  1  0
 13 31  1  0
 16 32  1  0
 18 33  1  0
 18 34  1  0
 20 35  1  0
 20 36  1  0
M  END


  Mrv0541 05061305302D          

 20 22  0  0  0  0            999 V2000
    8.9947   -0.4125    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
    5.4223    0.0000    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
    6.8513    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5658   -1.2375    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
    6.1368   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5658   -0.4125    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
    6.8513   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8513   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2802    0.0000    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
    6.1368   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  2  1  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>
MMDBc0053087

> <DATABASE_NAME>
MIME

> <SMILES>
COC1=CC(=O)OC(CCC2=CC3=C(OCO3)C=C2)C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H16O5/c1-17-12-7-11(20-15(16)8-12)4-2-10-3-5-13-14(6-10)19-9-18-13/h3,5-6,8,11H,2,4,7,9H2,1H3

> <INCHI_KEY>
RSIWXFIBHXYNFM-UHFFFAOYSA-N

> <FORMULA>
C15H16O5

> <MOLECULAR_WEIGHT>
276.2845

> <EXACT_MASS>
276.099773622

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
28.787933189717478

> <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)ethyl]-4-methoxy-5,6-dihydro-2H-pyran-2-one

> <ALOGPS_LOGP>
2.13

> <JCHEM_LOGP>
2.1792593430000005

> <ALOGPS_LOGS>
-3.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.42642045532562

> <JCHEM_PKA_STRONGEST_BASIC>
-4.46295375864894

> <JCHEM_POLAR_SURFACE_AREA>
53.99000000000001

> <JCHEM_REFRACTIVITY>
72.162

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.11e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
dihydromethysticin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030791
     RDKit          3D
Dihydromethysticin
 36 38  0  0  0  0  0  0  0  0999 V2000
    5.3192    2.1596   -0.1698 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5049    1.5611    0.8038 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7375    0.4491    0.5142 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2877   -0.7287    0.3306 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4907   -1.9205    0.0244 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0089   -3.0459   -0.1541 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1097   -1.7166   -0.0559 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6213   -0.6891    0.8162 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1324   -0.6972    0.7215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3887   -0.4341   -0.6646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8655   -0.4769   -0.5970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5685   -1.6345   -0.7881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9565   -1.6781   -0.7253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6131   -0.4983   -0.4599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9323    0.7072   -0.2582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5500    0.6852   -0.3337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8990    1.6742   -0.0187 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0969    1.1871   -0.5489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9831   -0.2093   -0.3327 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2755    0.5969    0.4094 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6719    2.4878   -1.0047 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7958    3.0493    0.3012 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0697    1.4147   -0.5236 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3839   -0.7934    0.4153 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9041   -0.8842    1.8723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3353    0.0545    1.3919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2224   -1.6940    1.0246 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0087   -1.1563   -1.4117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0235    0.5639   -0.9933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0566   -2.5768   -0.9995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5015   -2.5923   -0.8767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0380    1.6338   -0.1738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1567    1.3945   -1.6393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9985    1.5339    0.0013 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9023    1.4667    0.9897 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9619    0.8068   -0.6510 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
 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
  9 27  1  0
 10 28  1  0
 10 29  1  0
 12 30  1  0
 13 31  1  0
 16 32  1  0
 18 33  1  0
 18 34  1  0
 20 35  1  0
 20 36  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      16.790  -0.770   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      10.122   0.000   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      12.789   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      14.123  -2.310   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      11.455  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      14.123  -0.770   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      12.789  -3.080   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      12.789  -4.620   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      15.456   0.000   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      11.455  -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    HMDB0030791
HETATM    1  C1  UNL     1       5.319   2.160  -0.170  1.00  0.00           C  
HETATM    2  O1  UNL     1       4.505   1.561   0.804  1.00  0.00           O  
HETATM    3  C2  UNL     1       3.738   0.449   0.514  1.00  0.00           C  
HETATM    4  C3  UNL     1       4.288  -0.729   0.331  1.00  0.00           C  
HETATM    5  C4  UNL     1       3.491  -1.921   0.024  1.00  0.00           C  
HETATM    6  O2  UNL     1       4.009  -3.046  -0.154  1.00  0.00           O  
HETATM    7  O3  UNL     1       2.110  -1.717  -0.056  1.00  0.00           O  
HETATM    8  C5  UNL     1       1.621  -0.689   0.816  1.00  0.00           C  
HETATM    9  C6  UNL     1       0.132  -0.697   0.722  1.00  0.00           C  
HETATM   10  C7  UNL     1      -0.389  -0.434  -0.665  1.00  0.00           C  
HETATM   11  C8  UNL     1      -1.866  -0.477  -0.597  1.00  0.00           C  
HETATM   12  C9  UNL     1      -2.569  -1.634  -0.788  1.00  0.00           C  
HETATM   13  C10 UNL     1      -3.957  -1.678  -0.725  1.00  0.00           C  
HETATM   14  C11 UNL     1      -4.613  -0.498  -0.460  1.00  0.00           C  
HETATM   15  C12 UNL     1      -3.932   0.707  -0.258  1.00  0.00           C  
HETATM   16  C13 UNL     1      -2.550   0.685  -0.334  1.00  0.00           C  
HETATM   17  O4  UNL     1      -4.899   1.674  -0.019  1.00  0.00           O  
HETATM   18  C14 UNL     1      -6.097   1.187  -0.549  1.00  0.00           C  
HETATM   19  O5  UNL     1      -5.983  -0.209  -0.333  1.00  0.00           O  
HETATM   20  C15 UNL     1       2.275   0.597   0.409  1.00  0.00           C  
HETATM   21  H1  UNL     1       4.672   2.488  -1.005  1.00  0.00           H  
HETATM   22  H2  UNL     1       5.796   3.049   0.301  1.00  0.00           H  
HETATM   23  H3  UNL     1       6.070   1.415  -0.524  1.00  0.00           H  
HETATM   24  H4  UNL     1       5.384  -0.793   0.415  1.00  0.00           H  
HETATM   25  H5  UNL     1       1.904  -0.884   1.872  1.00  0.00           H  
HETATM   26  H6  UNL     1      -0.335   0.054   1.392  1.00  0.00           H  
HETATM   27  H7  UNL     1      -0.222  -1.694   1.025  1.00  0.00           H  
HETATM   28  H8  UNL     1       0.009  -1.156  -1.412  1.00  0.00           H  
HETATM   29  H9  UNL     1      -0.023   0.564  -0.993  1.00  0.00           H  
HETATM   30  H10 UNL     1      -2.057  -2.577  -0.999  1.00  0.00           H  
HETATM   31  H11 UNL     1      -4.502  -2.592  -0.877  1.00  0.00           H  
HETATM   32  H12 UNL     1      -2.038   1.634  -0.174  1.00  0.00           H  
HETATM   33  H13 UNL     1      -6.157   1.395  -1.639  1.00  0.00           H  
HETATM   34  H14 UNL     1      -6.998   1.534   0.001  1.00  0.00           H  
HETATM   35  H15 UNL     1       1.902   1.467   0.990  1.00  0.00           H  
HETATM   36  H16 UNL     1       1.962   0.807  -0.651  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   26   27
CONECT   10   11   28   29
CONECT   11   12   12   16
CONECT   12   13   30
CONECT   13   14   14   31
CONECT   14   15   19
CONECT   15   16   16   17
CONECT   16   32
CONECT   17   18
CONECT   18   19   33   34
CONECT   20   35   36
END

HMDB0030791
     RDKit          3D
Dihydromethysticin
 36 38  0  0  0  0  0  0  0  0999 V2000
    5.3192    2.1596   -0.1698 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5049    1.5611    0.8038 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7375    0.4491    0.5142 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2877   -0.7287    0.3306 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4907   -1.9205    0.0244 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0089   -3.0459   -0.1541 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1097   -1.7166   -0.0559 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6213   -0.6891    0.8162 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1324   -0.6972    0.7215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3887   -0.4341   -0.6646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8655   -0.4769   -0.5970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5685   -1.6345   -0.7881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9565   -1.6781   -0.7253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6131   -0.4983   -0.4599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9323    0.7072   -0.2582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5500    0.6852   -0.3337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8990    1.6742   -0.0187 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0969    1.1871   -0.5489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9831   -0.2093   -0.3327 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2755    0.5969    0.4094 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6719    2.4878   -1.0047 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7958    3.0493    0.3012 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0697    1.4147   -0.5236 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3839   -0.7934    0.4153 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9041   -0.8842    1.8723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3353    0.0545    1.3919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2224   -1.6940    1.0246 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0087   -1.1563   -1.4117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0235    0.5639   -0.9933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0566   -2.5768   -0.9995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5015   -2.5923   -0.8767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0380    1.6338   -0.1738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1567    1.3945   -1.6393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9985    1.5339    0.0013 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9023    1.4667    0.9897 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9619    0.8068   -0.6510 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
 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
  9 27  1  0
 10 28  1  0
 10 29  1  0
 12 30  1  0
 13 31  1  0
 16 32  1  0
 18 33  1  0
 18 34  1  0
 20 35  1  0
 20 36  1  0
M  END

Synonyms

Value	Source
(+)-Dihydromethysticin	HMDB
7,8-Dihydro-methysticin	HMDB
7,8-Dihydromethysticin	HMDB
DHM	HMDB
Pseudomethysticin	HMDB
Y-methysticin	HMDB

Molecular Formula

C₁₅H₁₆O₅

Average Mass

276.2845

Monoisotopic Mass

276.099773622

IUPAC Name

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

Traditional Name

dihydromethysticin

CAS Registry Number

Not Available

SMILES

COC1=CC(=O)OC(CCC2=CC3=C(OCO3)C=C2)C1

InChI Identifier

InChI=1S/C15H16O5/c1-17-12-7-11(20-15(16)8-12)4-2-10-3-5-13-14(6-10)19-9-18-13/h3,5-6,8,11H,2,4,7,9H2,1H3

InChI Key

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.091 g/L	ALOGPS
logP	2.13	ALOGPS
logP	2.18	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	16.43	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	4	ChemAxon
Refractivity	72.16 m³·mol⁻¹	ChemAxon
Polarizability	28.79 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

Spectra

Not Available

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

HMDB0030791

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

Dihydromethysticin

METLIN ID

Not Available

PubChem Compound

229852

PDB ID

Not Available

ChEBI ID

1034670

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

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 ]
Yannai, Shmuel (2004). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. Boca Raton: Chapman & Hall/CRC..

Showing metabocard for Dihydromethysticin (MMDBc0053087)

MOL for #<Metabolite:0x00007fecb73a13e8>

3D MOL for #<Metabolite:0x00007fecb73a13e8>

3D SDF for #<Metabolite:0x00007fecb73a13e8>

3D-SDF for #<Metabolite:0x00007fecb73a13e8>

PDB for #<Metabolite:0x00007fecb73a13e8>

3D PDB for #<Metabolite:0x00007fecb73a13e8>

SMILES for #<Metabolite:0x00007fecb73a13e8>

INCHI for #<Metabolite:0x00007fecb73a13e8>

Structure for #<Metabolite:0x00007fecb73a13e8>

3D Structure for #<Metabolite:0x00007fecb73a13e8>