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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 00:03:40 UTC

Update Date

2022-03-07 02:55:53 UTC

HMDB ID

HMDB0038722

Secondary Accession Numbers

HMDB38722

Metabolite Identification

Common Name

5,6-Dihydro-11-methoxyyangonin

Description

5,6-Dihydro-11-methoxyyangonin 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. 5,6-Dihydro-11-methoxyyangonin has been detected, but not quantified in, beverages. This could make 5,6-dihydro-11-methoxyyangonin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 5,6-Dihydro-11-methoxyyangonin.

Structure

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

HMDB0038722
     RDKit          3D
5,6-Dihydro-11-methoxyyangonin
 39 40  0  0  0  0  0  0  0  0999 V2000
    5.5945    1.1124   -0.6533 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4613   -0.2195   -0.1982 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2188   -0.8014    0.0544 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1139   -1.4442    1.2015 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8638   -2.0883    1.5694 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7097   -2.7215    2.6627 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8040   -1.9985    0.6776 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7258   -0.8903   -0.1645 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4513    0.3164    0.6186 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2943    0.7876    0.8557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9918    0.3025    0.4602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3447   -0.9588    0.0510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6405   -1.2503   -0.4195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5912   -0.2709   -0.4782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8573   -0.5366   -0.9335 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2120   -1.8400   -1.3563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2859    1.0212   -0.0733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2795    1.9902   -0.1471 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9353    3.2984    0.2730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0315    1.2687    0.3728 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0989   -0.7137   -0.8804 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1766    1.8521    0.0293 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6715    1.3005   -0.8307 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0574    1.1700   -1.6306 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9539   -1.5106    1.9009 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9730   -1.0256   -0.9426 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3567    0.8538    1.0346 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2889    1.7160    1.4809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6514   -1.7797    0.1273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8265   -2.2707   -0.7221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5570   -2.4757   -0.4940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1062   -1.7049   -2.0290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4436   -2.3257   -1.9653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7960    3.9871    0.2544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5246    3.1846    1.3106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0757    3.6617   -0.3402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8055    2.2810    0.6848 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0239    0.2483   -1.4129 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1182   -1.5260   -1.6369 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  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
 10 28  1  0
 12 29  1  0
 13 30  1  0
 16 31  1  0
 16 32  1  0
 16 33  1  0
 19 34  1  0
 19 35  1  0
 19 36  1  0
 20 37  1  0
 21 38  1  0
 21 39  1  0
M  END

  Mrv0541 05061310362D          

 21 22  0  0  0  0            999 V2000
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    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
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    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
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    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
    0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  4  2  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>
HMDB0038722

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C16H18O5/c1-18-13-9-12(21-16(17)10-13)6-4-11-5-7-14(19-2)15(8-11)20-3/h4-8,10,12H,9H2,1-3H3/b6-4-

> <INCHI_KEY>
FISBBPCLKKQWQA-XQRVVYSFSA-N

> <FORMULA>
C16H18O5

> <MOLECULAR_WEIGHT>
290.3111

> <EXACT_MASS>
290.115423686

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
30.27173201821322

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.75

> <JCHEM_LOGP>
2.117369147333333

> <ALOGPS_LOGS>
-3.99

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.54058020082843

> <JCHEM_PKA_STRONGEST_BASIC>
-4.378215245614213

> <JCHEM_POLAR_SURFACE_AREA>
53.99000000000001

> <JCHEM_REFRACTIVITY>
80.28410000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.96e-02 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0038722
     RDKit          3D
5,6-Dihydro-11-methoxyyangonin
 39 40  0  0  0  0  0  0  0  0999 V2000
    5.5945    1.1124   -0.6533 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4613   -0.2195   -0.1982 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2188   -0.8014    0.0544 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1139   -1.4442    1.2015 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8638   -2.0883    1.5694 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7097   -2.7215    2.6627 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8040   -1.9985    0.6776 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7258   -0.8903   -0.1645 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4513    0.3164    0.6186 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2943    0.7876    0.8557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9918    0.3025    0.4602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3447   -0.9588    0.0510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6405   -1.2503   -0.4195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5912   -0.2709   -0.4782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8573   -0.5366   -0.9335 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2120   -1.8400   -1.3563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2859    1.0212   -0.0733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2795    1.9902   -0.1471 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9353    3.2984    0.2730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0315    1.2687    0.3728 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0989   -0.7137   -0.8804 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1766    1.8521    0.0293 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6715    1.3005   -0.8307 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0574    1.1700   -1.6306 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9539   -1.5106    1.9009 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9730   -1.0256   -0.9426 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3567    0.8538    1.0346 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2889    1.7160    1.4809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6514   -1.7797    0.1273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8265   -2.2707   -0.7221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5570   -2.4757   -0.4940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1062   -1.7049   -2.0290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4436   -2.3257   -1.9653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7960    3.9871    0.2544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5246    3.1846    1.3106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0757    3.6617   -0.3402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8055    2.2810    0.6848 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0239    0.2483   -1.4129 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1182   -1.5260   -1.6369 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  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
 10 28  1  0
 12 29  1  0
 13 30  1  0
 16 31  1  0
 16 32  1  0
 16 33  1  0
 19 34  1  0
 19 35  1  0
 19 36  1  0
 20 37  1  0
 21 38  1  0
 21 39  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      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       2.667  -3.080   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    HMDB0038722
HETATM    1  C1  UNL     1       5.594   1.112  -0.653  1.00  0.00           C  
HETATM    2  O1  UNL     1       5.461  -0.219  -0.198  1.00  0.00           O  
HETATM    3  C2  UNL     1       4.219  -0.801   0.054  1.00  0.00           C  
HETATM    4  C3  UNL     1       4.114  -1.444   1.202  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.864  -2.088   1.569  1.00  0.00           C  
HETATM    6  O2  UNL     1       2.710  -2.722   2.663  1.00  0.00           O  
HETATM    7  O3  UNL     1       1.804  -1.998   0.678  1.00  0.00           O  
HETATM    8  C5  UNL     1       1.726  -0.890  -0.165  1.00  0.00           C  
HETATM    9  C6  UNL     1       1.451   0.316   0.619  1.00  0.00           C  
HETATM   10  C7  UNL     1       0.294   0.788   0.856  1.00  0.00           C  
HETATM   11  C8  UNL     1      -0.992   0.303   0.460  1.00  0.00           C  
HETATM   12  C9  UNL     1      -1.345  -0.959   0.051  1.00  0.00           C  
HETATM   13  C10 UNL     1      -2.640  -1.250  -0.419  1.00  0.00           C  
HETATM   14  C11 UNL     1      -3.591  -0.271  -0.478  1.00  0.00           C  
HETATM   15  O4  UNL     1      -4.857  -0.537  -0.933  1.00  0.00           O  
HETATM   16  C12 UNL     1      -5.212  -1.840  -1.356  1.00  0.00           C  
HETATM   17  C13 UNL     1      -3.286   1.021  -0.073  1.00  0.00           C  
HETATM   18  O5  UNL     1      -4.280   1.990  -0.147  1.00  0.00           O  
HETATM   19  C14 UNL     1      -3.935   3.298   0.273  1.00  0.00           C  
HETATM   20  C15 UNL     1      -2.032   1.269   0.373  1.00  0.00           C  
HETATM   21  C16 UNL     1       3.099  -0.714  -0.880  1.00  0.00           C  
HETATM   22  H1  UNL     1       5.177   1.852   0.029  1.00  0.00           H  
HETATM   23  H2  UNL     1       6.672   1.301  -0.831  1.00  0.00           H  
HETATM   24  H3  UNL     1       5.057   1.170  -1.631  1.00  0.00           H  
HETATM   25  H4  UNL     1       4.954  -1.511   1.901  1.00  0.00           H  
HETATM   26  H5  UNL     1       0.973  -1.026  -0.943  1.00  0.00           H  
HETATM   27  H6  UNL     1       2.357   0.854   1.035  1.00  0.00           H  
HETATM   28  H7  UNL     1       0.289   1.716   1.481  1.00  0.00           H  
HETATM   29  H8  UNL     1      -0.651  -1.780   0.127  1.00  0.00           H  
HETATM   30  H9  UNL     1      -2.827  -2.271  -0.722  1.00  0.00           H  
HETATM   31  H10 UNL     1      -5.557  -2.476  -0.494  1.00  0.00           H  
HETATM   32  H11 UNL     1      -6.106  -1.705  -2.029  1.00  0.00           H  
HETATM   33  H12 UNL     1      -4.444  -2.326  -1.965  1.00  0.00           H  
HETATM   34  H13 UNL     1      -4.796   3.987   0.254  1.00  0.00           H  
HETATM   35  H14 UNL     1      -3.525   3.185   1.311  1.00  0.00           H  
HETATM   36  H15 UNL     1      -3.076   3.662  -0.340  1.00  0.00           H  
HETATM   37  H16 UNL     1      -1.805   2.281   0.685  1.00  0.00           H  
HETATM   38  H17 UNL     1       3.024   0.248  -1.413  1.00  0.00           H  
HETATM   39  H18 UNL     1       3.118  -1.526  -1.637  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   10   27
CONECT   10   11   28
CONECT   11   12   12   20
CONECT   12   13   29
CONECT   13   14   14   30
CONECT   14   15   17
CONECT   15   16
CONECT   16   31   32   33
CONECT   17   18   20   20
CONECT   18   19
CONECT   19   34   35   36
CONECT   20   37
CONECT   21   38   39
END

HMDB0038722
     RDKit          3D
5,6-Dihydro-11-methoxyyangonin
 39 40  0  0  0  0  0  0  0  0999 V2000
    5.5945    1.1124   -0.6533 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4613   -0.2195   -0.1982 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2188   -0.8014    0.0544 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1139   -1.4442    1.2015 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8638   -2.0883    1.5694 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7097   -2.7215    2.6627 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8040   -1.9985    0.6776 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7258   -0.8903   -0.1645 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4513    0.3164    0.6186 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2943    0.7876    0.8557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9918    0.3025    0.4602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3447   -0.9588    0.0510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6405   -1.2503   -0.4195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5912   -0.2709   -0.4782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8573   -0.5366   -0.9335 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2120   -1.8400   -1.3563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2859    1.0212   -0.0733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2795    1.9902   -0.1471 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9353    3.2984    0.2730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0315    1.2687    0.3728 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0989   -0.7137   -0.8804 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1766    1.8521    0.0293 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6715    1.3005   -0.8307 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0574    1.1700   -1.6306 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9539   -1.5106    1.9009 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9730   -1.0256   -0.9426 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3567    0.8538    1.0346 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2889    1.7160    1.4809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6514   -1.7797    0.1273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8265   -2.2707   -0.7221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5570   -2.4757   -0.4940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1062   -1.7049   -2.0290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4436   -2.3257   -1.9653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7960    3.9871    0.2544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5246    3.1846    1.3106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0757    3.6617   -0.3402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8055    2.2810    0.6848 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0239    0.2483   -1.4129 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1182   -1.5260   -1.6369 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  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
 10 28  1  0
 12 29  1  0
 13 30  1  0
 16 31  1  0
 16 32  1  0
 16 33  1  0
 19 34  1  0
 19 35  1  0
 19 36  1  0
 20 37  1  0
 21 38  1  0
 21 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₆H₁₈O₅

Average Molecular Weight

290.3111

Monoisotopic Molecular Weight

290.115423686

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C16H18O5/c1-18-13-9-12(21-16(17)10-13)6-4-11-5-7-14(19-2)15(8-11)20-3/h4-8,10,12H,9H2,1-3H3/b6-4-

InChI Key

FISBBPCLKKQWQA-XQRVVYSFSA-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
O-dimethoxybenzene
Dimethoxybenzene
Phenoxy compound
Anisole
Phenol ether
Styrene
Methoxybenzene
Alkyl aryl ether
Dihydropyranone
Benzenoid
Pyran
Monocyclic benzene moiety
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Vinylogous 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: HMDB0038722)
Cell membrane (HMDB: HMDB0038722)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0038722)

Source

Exogenous

Exogenous (HMDB: HMDB0038722)

Food

Food (HMDB: HMDB0038722)

Beverage

Beverages (FooDB: FOOD00870)

Endogenous

Plant

Plant (HMDB: HMDB0038722)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0038722)

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
Water Solubility	0.03 g/L	ALOGPS
logP	2.75	ALOGPS
logP	2.12	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	16.54	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	5	ChemAxon
Refractivity	80.28 m³·mol⁻¹	ChemAxon
Polarizability	30.27 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]+	172.269	31661259
DarkChem	[M-H]-	172.788	31661259
DeepCCS	[M+H]+	169.522	30932474
DeepCCS	[M-H]-	167.164	30932474
DeepCCS	[M-2H]-	200.05	30932474
DeepCCS	[M+Na]+	175.615	30932474
AllCCS	[M+H]+	169.6	32859911
AllCCS	[M+H-H2O]+	165.8	32859911
AllCCS	[M+NH4]+	173.0	32859911
AllCCS	[M+Na]+	174.0	32859911
AllCCS	[M-H]-	171.5	32859911
AllCCS	[M+Na-2H]-	171.6	32859911
AllCCS	[M+HCOO]-	171.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5,6-Dihydro-11-methoxyyangonin	COC1=CC(=O)OC(C1)\C=C/C1=CC(OC)=C(OC)C=C1	3711.8	Standard polar	33892256
5,6-Dihydro-11-methoxyyangonin	COC1=CC(=O)OC(C1)\C=C/C1=CC(OC)=C(OC)C=C1	2456.8	Standard non polar	33892256
5,6-Dihydro-11-methoxyyangonin	COC1=CC(=O)OC(C1)\C=C/C1=CC(OC)=C(OC)C=C1	2706.8	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 - 5,6-Dihydro-11-methoxyyangonin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4m-5490000000-0d03fb3a33279072d888	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5,6-Dihydro-11-methoxyyangonin 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 - 5,6-Dihydro-11-methoxyyangonin 10V, Positive-QTOF	splash10-0006-0290000000-3b6b15895b66ff442e35	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-Dihydro-11-methoxyyangonin 20V, Positive-QTOF	splash10-000l-2960000000-9b660a98f605d5742f9a	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-Dihydro-11-methoxyyangonin 40V, Positive-QTOF	splash10-0kbr-4910000000-48d7abc999558122352e	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-Dihydro-11-methoxyyangonin 10V, Negative-QTOF	splash10-000i-0090000000-35c05a37b4b4e8b56507	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-Dihydro-11-methoxyyangonin 20V, Negative-QTOF	splash10-000f-6190000000-f33085ad8e549668855f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-Dihydro-11-methoxyyangonin 40V, Negative-QTOF	splash10-0006-9440000000-7fb796ab8f3849354bba	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-Dihydro-11-methoxyyangonin 10V, Negative-QTOF	splash10-000i-0090000000-580354e3fc377d71b791	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-Dihydro-11-methoxyyangonin 20V, Negative-QTOF	splash10-0bu1-0590000000-f3c4d125b68e6f93ab23	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-Dihydro-11-methoxyyangonin 40V, Negative-QTOF	splash10-00ke-3920000000-f371c588fa4083dc6230	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-Dihydro-11-methoxyyangonin 10V, Positive-QTOF	splash10-0006-0090000000-9e5b948e89ac494b711e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-Dihydro-11-methoxyyangonin 20V, Positive-QTOF	splash10-004i-0920000000-fae5d02097af739523f0	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-Dihydro-11-methoxyyangonin 40V, Positive-QTOF	splash10-004r-0910000000-ff33eaa98e604b722be1	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

FDB018130

KNApSAcK ID

Not Available

Chemspider ID

35014646

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131752440

PDB ID

Not Available

ChEBI ID

172521

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

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

Showing metabocard for 5,6-Dihydro-11-methoxyyangonin (HMDB0038722)

MOL for HMDB0038722 (5,6-Dihydro-11-methoxyyangonin)

3D MOL for HMDB0038722 (5,6-Dihydro-11-methoxyyangonin)

3D SDF for HMDB0038722 (5,6-Dihydro-11-methoxyyangonin)

3D-SDF for HMDB0038722 (5,6-Dihydro-11-methoxyyangonin)

PDB for HMDB0038722 (5,6-Dihydro-11-methoxyyangonin)

3D PDB for HMDB0038722 (5,6-Dihydro-11-methoxyyangonin)

SMILES for HMDB0038722 (5,6-Dihydro-11-methoxyyangonin)

INCHI for HMDB0038722 (5,6-Dihydro-11-methoxyyangonin)

Structure for HMDB0038722 (5,6-Dihydro-11-methoxyyangonin)

3D Structure for HMDB0038722 (5,6-Dihydro-11-methoxyyangonin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra