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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:38:54 UTC

Update Date

2022-03-07 02:52:41 UTC

HMDB ID

HMDB0030767

Secondary Accession Numbers

HMDB30767

Metabolite Identification

Common Name

11,12-Dimethoxydihydrokawain

Description

11,12-Dimethoxydihydrokawain, also known as 7,8-dihydro-11,12-dimethoxykawain, 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 11,12-Dimethoxydihydrokawain.

Structure

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

HMDB0030767
     RDKit          3D
11,12-Dimethoxydihydrokawain
 41 42  0  0  0  0  0  0  0  0999 V2000
    5.7006   -2.3487    0.3569 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7404   -1.0196   -0.1363 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6682   -0.1311    0.1081 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9411    1.1287    0.3632 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8940    2.1002    0.6233 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1674    3.2875    0.8635 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5812    1.6628    0.5954 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2849    0.5072   -0.1894 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8804    0.1077    0.1317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0548    1.2464   -0.2153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4574    0.8435    0.1071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9719    1.1041    1.3700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2581    0.7233    1.6345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0072    0.0963    0.6528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3176   -0.3021    0.8931 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8794   -0.0562    2.1635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5063   -0.1695   -0.6106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2474   -0.7924   -1.5887 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6899   -1.0377   -2.8536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2146    0.2196   -0.8574 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2710   -0.5950    0.0808 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7912   -2.8131   -0.1137 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5592   -2.9056   -0.0706 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7089   -2.4156    1.4458 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9994    1.4060    0.3691 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3341    0.7384   -1.2759 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5502   -0.8094   -0.3967 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7485   -0.0823    1.2282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0150    1.4740   -1.3078 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1678    2.1335    0.3996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3546    1.5975    2.1138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6622    0.9233    2.6131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9282   -0.4350    2.1403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8180    1.0031    2.4725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2587   -0.6505    2.8955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9687   -1.8809   -2.8467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2233   -0.1406   -3.2671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5278   -1.3580   -3.5219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7702    0.0310   -1.8458 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1144   -1.3748   -0.6924 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0285   -1.0161    1.0860 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  1  0
 14 17  1  0
 17 18  1  0
 18 19  1  0
 17 20  2  0
  8 21  1  0
 21  3  1  0
 20 11  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 12 31  1  0
 13 32  1  0
 16 33  1  0
 16 34  1  0
 16 35  1  0
 19 36  1  0
 19 37  1  0
 19 38  1  0
 20 39  1  0
 21 40  1  0
 21 41  1  0
M  END


  Mrv0541 05061305292D          

 21 22  0  0  0  0            999 V2000
    0.7145   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  4  1  0  0  0  0
  7  5  2  0  0  0  0
 11  4  1  0  0  0  0
 11  5  1  0  0  0  0
 11  8  2  0  0  0  0
 12  6  1  0  0  0  0
 12  9  1  0  0  0  0
 13  9  1  0  0  0  0
 13 10  2  0  0  0  0
 14  7  1  0  0  0  0
 15  8  1  0  0  0  0
 15 14  2  0  0  0  0
 16 10  1  0  0  0  0
 17 16  2  0  0  0  0
 18  1  1  0  0  0  0
 18 13  1  0  0  0  0
 19  2  1  0  0  0  0
 19 14  1  0  0  0  0
 20  3  1  0  0  0  0
 20 15  1  0  0  0  0
 21 12  1  0  0  0  0
 21 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030767

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C16H20O5/c1-18-13-9-12(21-16(17)10-13)6-4-11-5-7-14(19-2)15(8-11)20-3/h5,7-8,10,12H,4,6,9H2,1-3H3

> <INCHI_KEY>
HEURTYMJWQPWNN-UHFFFAOYSA-N

> <FORMULA>
C16H20O5

> <MOLECULAR_WEIGHT>
292.327

> <EXACT_MASS>
292.13107375

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
31.23678761751944

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-[2-(3,4-dimethoxyphenyl)ethyl]-4-methoxy-5,6-dihydro-2H-pyran-2-one

> <ALOGPS_LOGP>
2.60

> <JCHEM_LOGP>
2.240683344

> <ALOGPS_LOGS>
-3.97

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.426420456014693

> <JCHEM_PKA_STRONGEST_BASIC>
-4.3781330053970215

> <JCHEM_POLAR_SURFACE_AREA>
53.99000000000001

> <JCHEM_REFRACTIVITY>
79.3215

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.12e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-[2-(3,4-dimethoxyphenyl)ethyl]-4-methoxy-5,6-dihydropyran-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030767
     RDKit          3D
11,12-Dimethoxydihydrokawain
 41 42  0  0  0  0  0  0  0  0999 V2000
    5.7006   -2.3487    0.3569 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7404   -1.0196   -0.1363 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6682   -0.1311    0.1081 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9411    1.1287    0.3632 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8940    2.1002    0.6233 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1674    3.2875    0.8635 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5812    1.6628    0.5954 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2849    0.5072   -0.1894 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8804    0.1077    0.1317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0548    1.2464   -0.2153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4574    0.8435    0.1071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9719    1.1041    1.3700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2581    0.7233    1.6345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0072    0.0963    0.6528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3176   -0.3021    0.8931 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8794   -0.0562    2.1635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5063   -0.1695   -0.6106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2474   -0.7924   -1.5887 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6899   -1.0377   -2.8536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2146    0.2196   -0.8574 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2710   -0.5950    0.0808 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7912   -2.8131   -0.1137 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5592   -2.9056   -0.0706 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7089   -2.4156    1.4458 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9994    1.4060    0.3691 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3341    0.7384   -1.2759 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5502   -0.8094   -0.3967 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7485   -0.0823    1.2282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0150    1.4740   -1.3078 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1678    2.1335    0.3996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3546    1.5975    2.1138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6622    0.9233    2.6131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9282   -0.4350    2.1403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8180    1.0031    2.4725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2587   -0.6505    2.8955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9687   -1.8809   -2.8467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2233   -0.1406   -3.2671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5278   -1.3580   -3.5219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7702    0.0310   -1.8458 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1144   -1.3748   -0.6924 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0285   -1.0161    1.0860 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  1  0
 14 17  1  0
 17 18  1  0
 18 19  1  0
 17 20  2  0
  8 21  1  0
 21  3  1  0
 20 11  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 12 31  1  0
 13 32  1  0
 16 33  1  0
 16 34  1  0
 16 35  1  0
 19 36  1  0
 19 37  1  0
 19 38  1  0
 20 39  1  0
 21 40  1  0
 21 41  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       1.334 -16.170   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334 -10.010   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000 -12.320   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334 -14.630   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000 -13.860   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.667 -13.860   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -4.001 -14.630   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       1.334 -14.630   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -2.667 -12.320   0.000  0.00  0.00           O+0
CONECT    1   18                                                            
CONECT    2   19                                                            
CONECT    3   20                                                            
CONECT    4    6   11                                                       
CONECT    5    7   11                                                       
CONECT    6    4   12                                                       
CONECT    7    5   14                                                       
CONECT    8   11   15                                                       
CONECT    9   12   13                                                       
CONECT   10   13   16                                                       
CONECT   11    4    5    8                                                  
CONECT   12    6    9   21                                                  
CONECT   13    9   10   18                                                  
CONECT   14    7   15   19                                                  
CONECT   15    8   14   20                                                  
CONECT   16   10   17   21                                                  
CONECT   17   16                                                            
CONECT   18    1   13                                                       
CONECT   19    2   14                                                       
CONECT   20    3   15                                                       
CONECT   21   12   16                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

COMPND    HMDB0030767
HETATM    1  C1  UNL     1       5.701  -2.349   0.357  1.00  0.00           C  
HETATM    2  O1  UNL     1       5.740  -1.020  -0.136  1.00  0.00           O  
HETATM    3  C2  UNL     1       4.668  -0.131   0.108  1.00  0.00           C  
HETATM    4  C3  UNL     1       4.941   1.129   0.363  1.00  0.00           C  
HETATM    5  C4  UNL     1       3.894   2.100   0.623  1.00  0.00           C  
HETATM    6  O2  UNL     1       4.167   3.288   0.863  1.00  0.00           O  
HETATM    7  O3  UNL     1       2.581   1.663   0.595  1.00  0.00           O  
HETATM    8  C5  UNL     1       2.285   0.507  -0.189  1.00  0.00           C  
HETATM    9  C6  UNL     1       0.880   0.108   0.132  1.00  0.00           C  
HETATM   10  C7  UNL     1      -0.055   1.246  -0.215  1.00  0.00           C  
HETATM   11  C8  UNL     1      -1.457   0.843   0.107  1.00  0.00           C  
HETATM   12  C9  UNL     1      -1.972   1.104   1.370  1.00  0.00           C  
HETATM   13  C10 UNL     1      -3.258   0.723   1.635  1.00  0.00           C  
HETATM   14  C11 UNL     1      -4.007   0.096   0.653  1.00  0.00           C  
HETATM   15  O4  UNL     1      -5.318  -0.302   0.893  1.00  0.00           O  
HETATM   16  C12 UNL     1      -5.879  -0.056   2.163  1.00  0.00           C  
HETATM   17  C13 UNL     1      -3.506  -0.170  -0.611  1.00  0.00           C  
HETATM   18  O5  UNL     1      -4.247  -0.792  -1.589  1.00  0.00           O  
HETATM   19  C14 UNL     1      -3.690  -1.038  -2.854  1.00  0.00           C  
HETATM   20  C15 UNL     1      -2.215   0.220  -0.857  1.00  0.00           C  
HETATM   21  C16 UNL     1       3.271  -0.595   0.081  1.00  0.00           C  
HETATM   22  H1  UNL     1       4.791  -2.813  -0.114  1.00  0.00           H  
HETATM   23  H2  UNL     1       6.559  -2.906  -0.071  1.00  0.00           H  
HETATM   24  H3  UNL     1       5.709  -2.416   1.446  1.00  0.00           H  
HETATM   25  H4  UNL     1       5.999   1.406   0.369  1.00  0.00           H  
HETATM   26  H5  UNL     1       2.334   0.738  -1.276  1.00  0.00           H  
HETATM   27  H6  UNL     1       0.550  -0.809  -0.397  1.00  0.00           H  
HETATM   28  H7  UNL     1       0.749  -0.082   1.228  1.00  0.00           H  
HETATM   29  H8  UNL     1      -0.015   1.474  -1.308  1.00  0.00           H  
HETATM   30  H9  UNL     1       0.168   2.133   0.400  1.00  0.00           H  
HETATM   31  H10 UNL     1      -1.355   1.597   2.114  1.00  0.00           H  
HETATM   32  H11 UNL     1      -3.662   0.923   2.613  1.00  0.00           H  
HETATM   33  H12 UNL     1      -6.928  -0.435   2.140  1.00  0.00           H  
HETATM   34  H13 UNL     1      -5.818   1.003   2.473  1.00  0.00           H  
HETATM   35  H14 UNL     1      -5.259  -0.650   2.895  1.00  0.00           H  
HETATM   36  H15 UNL     1      -2.969  -1.881  -2.847  1.00  0.00           H  
HETATM   37  H16 UNL     1      -3.223  -0.141  -3.267  1.00  0.00           H  
HETATM   38  H17 UNL     1      -4.528  -1.358  -3.522  1.00  0.00           H  
HETATM   39  H18 UNL     1      -1.770   0.031  -1.846  1.00  0.00           H  
HETATM   40  H19 UNL     1       3.114  -1.375  -0.692  1.00  0.00           H  
HETATM   41  H20 UNL     1       3.028  -1.016   1.086  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3
CONECT    3    4    4   21
CONECT    4    5   25
CONECT    5    6    6    7
CONECT    7    8
CONECT    8    9   21   26
CONECT    9   10   27   28
CONECT   10   11   29   30
CONECT   11   12   12   20
CONECT   12   13   31
CONECT   13   14   14   32
CONECT   14   15   17
CONECT   15   16
CONECT   16   33   34   35
CONECT   17   18   20   20
CONECT   18   19
CONECT   19   36   37   38
CONECT   20   39
CONECT   21   40   41
END

HMDB0030767
     RDKit          3D
11,12-Dimethoxydihydrokawain
 41 42  0  0  0  0  0  0  0  0999 V2000
    5.7006   -2.3487    0.3569 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7404   -1.0196   -0.1363 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6682   -0.1311    0.1081 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9411    1.1287    0.3632 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8940    2.1002    0.6233 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1674    3.2875    0.8635 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5812    1.6628    0.5954 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2849    0.5072   -0.1894 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8804    0.1077    0.1317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0548    1.2464   -0.2153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4574    0.8435    0.1071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9719    1.1041    1.3700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2581    0.7233    1.6345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0072    0.0963    0.6528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3176   -0.3021    0.8931 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8794   -0.0562    2.1635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5063   -0.1695   -0.6106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2474   -0.7924   -1.5887 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6899   -1.0377   -2.8536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2146    0.2196   -0.8574 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2710   -0.5950    0.0808 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7912   -2.8131   -0.1137 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5592   -2.9056   -0.0706 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7089   -2.4156    1.4458 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9994    1.4060    0.3691 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3341    0.7384   -1.2759 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5502   -0.8094   -0.3967 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7485   -0.0823    1.2282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0150    1.4740   -1.3078 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1678    2.1335    0.3996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3546    1.5975    2.1138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6622    0.9233    2.6131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9282   -0.4350    2.1403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8180    1.0031    2.4725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2587   -0.6505    2.8955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9687   -1.8809   -2.8467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2233   -0.1406   -3.2671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5278   -1.3580   -3.5219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7702    0.0310   -1.8458 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1144   -1.3748   -0.6924 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0285   -1.0161    1.0860 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  1  0
 14 17  1  0
 17 18  1  0
 18 19  1  0
 17 20  2  0
  8 21  1  0
 21  3  1  0
 20 11  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 12 31  1  0
 13 32  1  0
 16 33  1  0
 16 34  1  0
 16 35  1  0
 19 36  1  0
 19 37  1  0
 19 38  1  0
 20 39  1  0
 21 40  1  0
 21 41  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
5,6,7,8-Tetrahydro-11-methoxyyangonin	HMDB
6-[(3,4-Dimethoxyphenyl)ethyl]-5,6-dihydro-4-methoxy-2H-pyran-2-one	HMDB
7,8-Dihydro-11,12-dimethoxykawain	HMDB

Chemical Formula

C₁₆H₂₀O₅

Average Molecular Weight

292.327

Monoisotopic Molecular Weight

292.13107375

IUPAC Name

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

Traditional Name

6-[2-(3,4-dimethoxyphenyl)ethyl]-4-methoxy-5,6-dihydropyran-2-one

CAS Registry Number

38146-60-0

SMILES

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

InChI Identifier

InChI=1S/C16H20O5/c1-18-13-9-12(21-16(17)10-13)6-4-11-5-7-14(19-2)15(8-11)20-3/h5,7-8,10,12H,4,6,9H2,1-3H3

InChI Key

HEURTYMJWQPWNN-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
Dimethoxybenzene
O-dimethoxybenzene
Phenoxy compound
Anisole
Phenol ether
Methoxybenzene
Alkyl aryl ether
Dihydropyranone
Benzenoid
Pyran
Monocyclic benzene moiety
Vinylogous ester
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Ether
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Organic oxide
Organooxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0030767)
Cell membrane (HMDB: HMDB0030767)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030767)

Source

Endogenous

Endogenous (HMDB: HMDB0030767)

Plant

Plant (HMDB: HMDB0030767)

Exogenous

Food

Food (HMDB: HMDB0030767)

Beverage

Beverages (FooDB: FOOD00870)

Exogenous (HMDB: HMDB0030767)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	124 - 125 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	681.6 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	0.031 g/L	ALOGPS
logP	2.6	ALOGPS
logP	2.24	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	16.43	ChemAxon
pKa (Strongest Basic)	-4.4	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	6	ChemAxon
Refractivity	79.32 m³·mol⁻¹	ChemAxon
Polarizability	31.24 Å³	ChemAxon
Number of Rings	2	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]+	170.782	31661259
DarkChem	[M-H]-	172.594	31661259
DeepCCS	[M+H]+	164.609	30932474
DeepCCS	[M-H]-	162.251	30932474
DeepCCS	[M-2H]-	195.503	30932474
DeepCCS	[M+Na]+	170.731	30932474
AllCCS	[M+H]+	170.7	32859911
AllCCS	[M+H-H2O]+	167.1	32859911
AllCCS	[M+NH4]+	174.1	32859911
AllCCS	[M+Na]+	175.0	32859911
AllCCS	[M-H]-	173.3	32859911
AllCCS	[M+Na-2H]-	173.6	32859911
AllCCS	[M+HCOO]-	174.0	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022.	7.73 minutes	32390414
Predicted by Siyang on May 30, 2022	14.3461 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.94 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	24.2 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2276.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	347.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	184.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	197.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	105.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	571.5 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	614.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	120.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1266.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	500.4 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1480.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	339.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	416.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	352.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	347.5 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	15.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
11,12-Dimethoxydihydrokawain	COC1=CC(=O)OC(CCC2=CC(OC)=C(OC)C=C2)C1	3552.5	Standard polar	33892256
11,12-Dimethoxydihydrokawain	COC1=CC(=O)OC(CCC2=CC(OC)=C(OC)C=C2)C1	2382.2	Standard non polar	33892256
11,12-Dimethoxydihydrokawain	COC1=CC(=O)OC(CCC2=CC(OC)=C(OC)C=C2)C1	2600.0	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 - 11,12-Dimethoxydihydrokawain GC-MS (Non-derivatized) - 70eV, Positive	splash10-0zfr-5960000000-93df114c5e293c85121a	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 11,12-Dimethoxydihydrokawain GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 11,12-Dimethoxydihydrokawain 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 - 11,12-Dimethoxydihydrokawain , positive-QTOF	splash10-0udi-0900000000-a208c49bac50d131843e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 11,12-Dimethoxydihydrokawain , positive-QTOF	splash10-0ufr-0910000000-86994de4c762d8537e8f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 11,12-Dimethoxydihydrokawain 10V, Positive-QTOF	splash10-004i-0930000000-6640b315a89d83e6b7e8	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 11,12-Dimethoxydihydrokawain 20V, Positive-QTOF	splash10-0ufr-0900000000-1b032017edc7beb8a28b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 11,12-Dimethoxydihydrokawain 40V, Positive-QTOF	splash10-0zfr-0900000000-9e4dcfc059c5888c6a0c	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11,12-Dimethoxydihydrokawain 10V, Positive-QTOF	splash10-0006-0290000000-ea796836310a35ab1e74	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11,12-Dimethoxydihydrokawain 20V, Positive-QTOF	splash10-004l-1930000000-df2965731a0bcad9106b	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11,12-Dimethoxydihydrokawain 40V, Positive-QTOF	splash10-0kdu-5900000000-4013e7bf5e8c6f553da8	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11,12-Dimethoxydihydrokawain 10V, Negative-QTOF	splash10-0006-0090000000-71d1dd33481c323fcf8b	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11,12-Dimethoxydihydrokawain 20V, Negative-QTOF	splash10-0006-8190000000-5ee280669450d611b1b8	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11,12-Dimethoxydihydrokawain 40V, Negative-QTOF	splash10-0006-9340000000-fb7f2ba382d1ef8cc390	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11,12-Dimethoxydihydrokawain 10V, Negative-QTOF	splash10-014i-0090000000-9b822eb019dcecf0bb12	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11,12-Dimethoxydihydrokawain 20V, Negative-QTOF	splash10-014i-0190000000-9df1463bfadfd91e36a9	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11,12-Dimethoxydihydrokawain 40V, Negative-QTOF	splash10-05ce-4910000000-d592ac9032add3b7061e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11,12-Dimethoxydihydrokawain 10V, Positive-QTOF	splash10-002g-0490000000-69edbea33083602370f7	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11,12-Dimethoxydihydrokawain 20V, Positive-QTOF	splash10-004u-0910000000-2f0e268dca39fcf8c481	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11,12-Dimethoxydihydrokawain 40V, Positive-QTOF	splash10-004r-1910000000-fe8ea0667d27154d7bfd	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

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

FDB002702

KNApSAcK ID

C00054408

Chemspider ID

514824

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

592220

PDB ID

Not Available

ChEBI ID

110179

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1822591

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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

Showing metabocard for 11,12-Dimethoxydihydrokawain (HMDB0030767)

MOL for HMDB0030767 (11,12-Dimethoxydihydrokawain)

3D MOL for HMDB0030767 (11,12-Dimethoxydihydrokawain)

3D SDF for HMDB0030767 (11,12-Dimethoxydihydrokawain)

3D-SDF for HMDB0030767 (11,12-Dimethoxydihydrokawain)

PDB for HMDB0030767 (11,12-Dimethoxydihydrokawain)

3D PDB for HMDB0030767 (11,12-Dimethoxydihydrokawain)

SMILES for HMDB0030767 (11,12-Dimethoxydihydrokawain)

INCHI for HMDB0030767 (11,12-Dimethoxydihydrokawain)

Structure for HMDB0030767 (11,12-Dimethoxydihydrokawain)

3D Structure for HMDB0030767 (11,12-Dimethoxydihydrokawain)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra