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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:39:03 UTC

Update Date

2022-03-07 02:52:42 UTC

HMDB ID

HMDB0030791

Secondary Accession Numbers

HMDB30791

Metabolite Identification

Common Name

Dihydromethysticin

Description

Dihydromethysticin, also known as DHM or pseudomethysticin, 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. Dihydromethysticin is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review very few articles have been published on Dihydromethysticin.

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>
HMDB0030791

> <DATABASE_NAME>
hmdb

> <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

View in JSmol View Stereo Labels

Synonyms

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

Chemical Formula

C₁₅H₁₆O₅

Average Molecular Weight

276.2845

Monoisotopic Molecular Weight

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

19902-91-1

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

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0030791)
Cytoplasm (HMDB: HMDB0030791)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030791)

Source

Endogenous

Endogenous (HMDB: HMDB0030791)

Plant

Plant (HMDB: HMDB0030791)

Exogenous

Food

Food (HMDB: HMDB0030791)

Beverage

Beverages (FooDB: FOOD00870)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Tetrahydromonapterin Biosynthesis (PathBank: SMP0002057)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	117 - 118 °C	Not Available
Boiling Point	476.10 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	582 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.810 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	166.285	31661259
DarkChem	[M-H]-	167.011	31661259
DeepCCS	[M+H]+	159.702	30932474
DeepCCS	[M-H]-	157.344	30932474
DeepCCS	[M-2H]-	190.461	30932474
DeepCCS	[M+Na]+	165.796	30932474
AllCCS	[M+H]+	165.4	32859911
AllCCS	[M+H-H2O]+	161.6	32859911
AllCCS	[M+NH4]+	168.9	32859911
AllCCS	[M+Na]+	169.9	32859911
AllCCS	[M-H]-	168.6	32859911
AllCCS	[M+Na-2H]-	168.4	32859911
AllCCS	[M+HCOO]-	168.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dihydromethysticin	COC1=CC(=O)OC(CCC2=CC3=C(OCO3)C=C2)C1	3465.1	Standard polar	33892256
Dihydromethysticin	COC1=CC(=O)OC(CCC2=CC3=C(OCO3)C=C2)C1	2208.5	Standard non polar	33892256
Dihydromethysticin	COC1=CC(=O)OC(CCC2=CC3=C(OCO3)C=C2)C1	2539.8	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 - Dihydromethysticin GC-MS (Non-derivatized) - 70eV, Positive	splash10-000i-3940000000-c6f60a0812c997c26524	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydromethysticin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydromethysticin 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dihydromethysticin LC-ESI-qTof , Positive-QTOF	splash10-0007-0901000000-4fa10fe72dc24b85ac9c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dihydromethysticin , positive-QTOF	splash10-000i-0910000000-58a79c1f813a6b5fb309	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydromethysticin 10V, Positive-QTOF	splash10-004i-0290000000-cf76d86e9d1c1b367c52	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydromethysticin 20V, Positive-QTOF	splash10-03fr-1930000000-427b71dd445f94591686	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydromethysticin 40V, Positive-QTOF	splash10-0kdi-6900000000-b81fa00677b631b316f5	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydromethysticin 10V, Negative-QTOF	splash10-004i-0090000000-2234da833302b4c46920	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydromethysticin 20V, Negative-QTOF	splash10-054o-9180000000-99b41a6b340693b87f72	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydromethysticin 40V, Negative-QTOF	splash10-0006-9420000000-c18538f8c4275cd9f2c4	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydromethysticin 10V, Negative-QTOF	splash10-0002-0900000000-85db899e345a8672fcfe	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydromethysticin 20V, Negative-QTOF	splash10-0002-0920000000-fdfef8aa81e70df5e984	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydromethysticin 40V, Negative-QTOF	splash10-05nn-3910000000-3104abd7baaf201be146	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydromethysticin 10V, Positive-QTOF	splash10-004i-0390000000-00dc0c15ad9ec124b354	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydromethysticin 20V, Positive-QTOF	splash10-03fr-0920000000-01061a38dd546692e276	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydromethysticin 40V, Positive-QTOF	splash10-08or-2910000000-049831c5eb951d3ddca5	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

Dihydromethysticin

METLIN ID

Not Available

PubChem Compound

229852

PDB ID

Not Available

ChEBI ID

1034670

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1479191

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

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

Showing metabocard for Dihydromethysticin (HMDB0030791)

MOL for HMDB0030791 (Dihydromethysticin)

3D MOL for HMDB0030791 (Dihydromethysticin)

3D SDF for HMDB0030791 (Dihydromethysticin)

3D-SDF for HMDB0030791 (Dihydromethysticin)

PDB for HMDB0030791 (Dihydromethysticin)

3D PDB for HMDB0030791 (Dihydromethysticin)

SMILES for HMDB0030791 (Dihydromethysticin)

INCHI for HMDB0030791 (Dihydromethysticin)

Structure for HMDB0030791 (Dihydromethysticin)

3D Structure for HMDB0030791 (Dihydromethysticin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra