Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2) Show 2 proteins XML

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

HMDB0030766

Secondary Accession Numbers

HMDB30766

Metabolite Identification

Common Name

11-Hydroxy-12-methoxydihydrokawain

Description

11-Hydroxy-12-methoxydihydrokawain 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-Hydroxy-12-methoxydihydrokawain.

Structure

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

HMDB0030766
     RDKit          3D
11-Hydroxy-12-methoxydihydrokawain
 38 39  0  0  0  0  0  0  0  0999 V2000
    5.9050    1.8433   -0.5638 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5083    0.4838   -0.7129 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3939   -0.0322   -0.0342 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5165   -0.9277    0.9240 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3798   -1.4820    1.6448 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4583   -2.3279    2.5553 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1288   -0.9818    1.2320 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0222   -0.5422   -0.1199 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6178   -0.0086   -0.3094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3340   -1.1441   -0.0167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7414   -0.7255   -0.1739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4494   -0.2043    0.8889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7706    0.2006    0.7854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4268    0.0858   -0.4268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7564    0.4906   -0.5408 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4255    1.0159    0.5835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7168   -0.4334   -1.4800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3978   -0.5423   -2.7008 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3964   -0.8372   -1.3734 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0709    0.4666   -0.4316 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0656    2.4928   -0.8965 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7976    1.9790   -1.2081 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1734    2.0225    0.4812 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5225   -1.2526    1.1704 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1415   -1.3977   -0.8312 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4181    0.7895    0.4512 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5478    0.3723   -1.3344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1581   -1.4273    1.0576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0623   -1.9936   -0.6722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9745   -0.0924    1.8725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2839    0.6071    1.6615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8191    1.8174    1.0817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5378    0.2093    1.3441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3879    1.4782    0.3347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9817   -0.9038   -3.5280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9095   -1.2360   -2.2528 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8134    1.4021    0.1120 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0486    0.7356   -1.5084 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
 17 19  2  0
  8 20  1  0
 20  3  1  0
 19 11  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
 16 33  1  0
 16 34  1  0
 18 35  1  0
 19 36  1  0
 20 37  1  0
 20 38  1  0
M  END


  Mrv0541 05061305292D          

 20 21  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
    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
   -0.7145   -2.8875    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
   -1.4289   -7.4250    0.0000 C   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
   -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   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  3  1  0  0  0  0
  6  4  2  0  0  0  0
 10  3  1  0  0  0  0
 10  4  1  0  0  0  0
 10  7  2  0  0  0  0
 11  5  1  0  0  0  0
 11  8  1  0  0  0  0
 12  8  1  0  0  0  0
 12  9  2  0  0  0  0
 13  7  1  0  0  0  0
 14  6  1  0  0  0  0
 14 13  2  0  0  0  0
 15  9  1  0  0  0  0
 16 13  1  0  0  0  0
 17 15  2  0  0  0  0
 18  1  1  0  0  0  0
 18 12  1  0  0  0  0
 19  2  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>
HMDB0030766

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C15H18O5/c1-18-12-8-11(20-15(17)9-12)5-3-10-4-6-14(19-2)13(16)7-10/h4,6-7,9,11,16H,3,5,8H2,1-2H3

> <INCHI_KEY>
QQLVNWDQIUZGJM-UHFFFAOYSA-N

> <FORMULA>
C15H18O5

> <MOLECULAR_WEIGHT>
278.3004

> <EXACT_MASS>
278.115423686

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
29.24931290039882

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.17

> <JCHEM_LOGP>
2.0947892880000003

> <ALOGPS_LOGS>
-3.39

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.42644774915038

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.904489916983517

> <JCHEM_PKA_STRONGEST_BASIC>
-4.535259747510902

> <JCHEM_POLAR_SURFACE_AREA>
64.99000000000001

> <JCHEM_REFRACTIVITY>
74.8392

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.14e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030766
     RDKit          3D
11-Hydroxy-12-methoxydihydrokawain
 38 39  0  0  0  0  0  0  0  0999 V2000
    5.9050    1.8433   -0.5638 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5083    0.4838   -0.7129 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3939   -0.0322   -0.0342 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5165   -0.9277    0.9240 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3798   -1.4820    1.6448 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4583   -2.3279    2.5553 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1288   -0.9818    1.2320 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0222   -0.5422   -0.1199 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6178   -0.0086   -0.3094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3340   -1.1441   -0.0167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7414   -0.7255   -0.1739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4494   -0.2043    0.8889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7706    0.2006    0.7854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4268    0.0858   -0.4268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7564    0.4906   -0.5408 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4255    1.0159    0.5835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7168   -0.4334   -1.4800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3978   -0.5423   -2.7008 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3964   -0.8372   -1.3734 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0709    0.4666   -0.4316 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0656    2.4928   -0.8965 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7976    1.9790   -1.2081 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1734    2.0225    0.4812 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5225   -1.2526    1.1704 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1415   -1.3977   -0.8312 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4181    0.7895    0.4512 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5478    0.3723   -1.3344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1581   -1.4273    1.0576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0623   -1.9936   -0.6722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9745   -0.0924    1.8725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2839    0.6071    1.6615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8191    1.8174    1.0817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5378    0.2093    1.3441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3879    1.4782    0.3347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9817   -0.9038   -3.5280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9095   -1.2360   -2.2528 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8134    1.4021    0.1120 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0486    0.7356   -1.5084 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
 17 19  2  0
  8 20  1  0
 20  3  1  0
 19 11  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
 16 33  1  0
 16 34  1  0
 18 35  1  0
 19 36  1  0
 20 37  1  0
 20 38  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       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334 -10.010   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000 -12.320   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334 -14.630   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000 -13.860   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.334  -5.390   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      -2.667 -13.860   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -2.667  -4.620   0.000  0.00  0.00           O+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 -12.320   0.000  0.00  0.00           O+0
CONECT    1   18                                                            
CONECT    2   19                                                            
CONECT    3    5   10                                                       
CONECT    4    6   10                                                       
CONECT    5    3   11                                                       
CONECT    6    4   14                                                       
CONECT    7   10   13                                                       
CONECT    8   11   12                                                       
CONECT    9   12   15                                                       
CONECT   10    3    4    7                                                  
CONECT   11    5    8   20                                                  
CONECT   12    8    9   18                                                  
CONECT   13    7   14   16                                                  
CONECT   14    6   13   19                                                  
CONECT   15    9   17   20                                                  
CONECT   16   13                                                            
CONECT   17   15                                                            
CONECT   18    1   12                                                       
CONECT   19    2   14                                                       
CONECT   20   11   15                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

COMPND    HMDB0030766
HETATM    1  C1  UNL     1       5.905   1.843  -0.564  1.00  0.00           C  
HETATM    2  O1  UNL     1       5.508   0.484  -0.713  1.00  0.00           O  
HETATM    3  C2  UNL     1       4.394  -0.032  -0.034  1.00  0.00           C  
HETATM    4  C3  UNL     1       4.517  -0.928   0.924  1.00  0.00           C  
HETATM    5  C4  UNL     1       3.380  -1.482   1.645  1.00  0.00           C  
HETATM    6  O2  UNL     1       3.458  -2.328   2.555  1.00  0.00           O  
HETATM    7  O3  UNL     1       2.129  -0.982   1.232  1.00  0.00           O  
HETATM    8  C5  UNL     1       2.022  -0.542  -0.120  1.00  0.00           C  
HETATM    9  C6  UNL     1       0.618  -0.009  -0.309  1.00  0.00           C  
HETATM   10  C7  UNL     1      -0.334  -1.144  -0.017  1.00  0.00           C  
HETATM   11  C8  UNL     1      -1.741  -0.726  -0.174  1.00  0.00           C  
HETATM   12  C9  UNL     1      -2.449  -0.204   0.889  1.00  0.00           C  
HETATM   13  C10 UNL     1      -3.771   0.201   0.785  1.00  0.00           C  
HETATM   14  C11 UNL     1      -4.427   0.086  -0.427  1.00  0.00           C  
HETATM   15  O4  UNL     1      -5.756   0.491  -0.541  1.00  0.00           O  
HETATM   16  C12 UNL     1      -6.425   1.016   0.583  1.00  0.00           C  
HETATM   17  C13 UNL     1      -3.717  -0.433  -1.480  1.00  0.00           C  
HETATM   18  O5  UNL     1      -4.398  -0.542  -2.701  1.00  0.00           O  
HETATM   19  C14 UNL     1      -2.396  -0.837  -1.373  1.00  0.00           C  
HETATM   20  C15 UNL     1       3.071   0.467  -0.432  1.00  0.00           C  
HETATM   21  H1  UNL     1       5.066   2.493  -0.897  1.00  0.00           H  
HETATM   22  H2  UNL     1       6.798   1.979  -1.208  1.00  0.00           H  
HETATM   23  H3  UNL     1       6.173   2.023   0.481  1.00  0.00           H  
HETATM   24  H4  UNL     1       5.522  -1.253   1.170  1.00  0.00           H  
HETATM   25  H5  UNL     1       2.142  -1.398  -0.831  1.00  0.00           H  
HETATM   26  H6  UNL     1       0.418   0.790   0.451  1.00  0.00           H  
HETATM   27  H7  UNL     1       0.548   0.372  -1.334  1.00  0.00           H  
HETATM   28  H8  UNL     1      -0.158  -1.427   1.058  1.00  0.00           H  
HETATM   29  H9  UNL     1      -0.062  -1.994  -0.672  1.00  0.00           H  
HETATM   30  H10 UNL     1      -1.975  -0.092   1.873  1.00  0.00           H  
HETATM   31  H11 UNL     1      -4.284   0.607   1.662  1.00  0.00           H  
HETATM   32  H12 UNL     1      -5.819   1.817   1.082  1.00  0.00           H  
HETATM   33  H13 UNL     1      -6.538   0.209   1.344  1.00  0.00           H  
HETATM   34  H14 UNL     1      -7.388   1.478   0.335  1.00  0.00           H  
HETATM   35  H15 UNL     1      -3.982  -0.904  -3.528  1.00  0.00           H  
HETATM   36  H16 UNL     1      -1.909  -1.236  -2.253  1.00  0.00           H  
HETATM   37  H17 UNL     1       2.813   1.402   0.112  1.00  0.00           H  
HETATM   38  H18 UNL     1       3.049   0.736  -1.508  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   19
CONECT   12   13   30
CONECT   13   14   14   31
CONECT   14   15   17
CONECT   15   16
CONECT   16   32   33   34
CONECT   17   18   19   19
CONECT   18   35
CONECT   19   36
CONECT   20   37   38
END

HMDB0030766
     RDKit          3D
11-Hydroxy-12-methoxydihydrokawain
 38 39  0  0  0  0  0  0  0  0999 V2000
    5.9050    1.8433   -0.5638 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5083    0.4838   -0.7129 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3939   -0.0322   -0.0342 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5165   -0.9277    0.9240 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3798   -1.4820    1.6448 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4583   -2.3279    2.5553 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1288   -0.9818    1.2320 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0222   -0.5422   -0.1199 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6178   -0.0086   -0.3094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3340   -1.1441   -0.0167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7414   -0.7255   -0.1739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4494   -0.2043    0.8889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7706    0.2006    0.7854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4268    0.0858   -0.4268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7564    0.4906   -0.5408 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4255    1.0159    0.5835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7168   -0.4334   -1.4800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3978   -0.5423   -2.7008 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3964   -0.8372   -1.3734 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0709    0.4666   -0.4316 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0656    2.4928   -0.8965 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7976    1.9790   -1.2081 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1734    2.0225    0.4812 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5225   -1.2526    1.1704 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1415   -1.3977   -0.8312 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4181    0.7895    0.4512 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5478    0.3723   -1.3344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1581   -1.4273    1.0576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0623   -1.9936   -0.6722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9745   -0.0924    1.8725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2839    0.6071    1.6615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8191    1.8174    1.0817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5378    0.2093    1.3441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3879    1.4782    0.3347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9817   -0.9038   -3.5280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9095   -1.2360   -2.2528 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8134    1.4021    0.1120 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0486    0.7356   -1.5084 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
 17 19  2  0
  8 20  1  0
 20  3  1  0
 19 11  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
 16 33  1  0
 16 34  1  0
 18 35  1  0
 19 36  1  0
 20 37  1  0
 20 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
11-Hydroxy-12-methoxydihydrokavain	HMDB
4-Methoxy-6-[2-(3-hydroxy-4-methoxyphenyl)ethyl]-5,6-dihydro-2H-pyran-2-one	HMDB

Chemical Formula

C₁₅H₁₈O₅

Average Molecular Weight

278.3004

Monoisotopic Molecular Weight

278.115423686

IUPAC Name

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

Traditional Name

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

CAS Registry Number

38146-59-7

SMILES

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

InChI Identifier

InChI=1S/C15H18O5/c1-18-12-8-11(20-15(17)9-12)5-3-10-4-6-14(19-2)13(16)7-10/h4,6-7,9,11,16H,3,5,8H2,1-2H3

InChI Key

QQLVNWDQIUZGJM-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
Methoxyphenol
Phenoxy compound
Anisole
Phenol ether
Methoxybenzene
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
Dihydropyranone
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Monocyclic benzene moiety
Pyran
Vinylogous ester
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Lactone
Carboxylic acid ester
Monocarboxylic acid or derivatives
Ether
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Carbonyl group
Organic oxide
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0030766)
Cytoplasm (HMDB: HMDB0030766)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030766)

Source

Endogenous

Endogenous (HMDB: HMDB0030766)

Plant

Plant (HMDB: HMDB0030766)

Exogenous

Food

Food (HMDB: HMDB0030766)

Beverage

Beverages (FooDB: FOOD00870)

Exogenous (HMDB: HMDB0030766)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	165 - 167 °C	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	0.11 g/L	ALOGPS
logP	2.17	ALOGPS
logP	2.09	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	9.9	ChemAxon
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	64.99 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	74.84 m³·mol⁻¹	ChemAxon
Polarizability	29.25 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]+	167.534	31661259
DarkChem	[M-H]-	168.154	31661259
DeepCCS	[M+H]+	162.519	30932474
DeepCCS	[M-H]-	160.161	30932474
DeepCCS	[M-2H]-	193.298	30932474
DeepCCS	[M+Na]+	168.612	30932474
AllCCS	[M+H]+	166.8	32859911
AllCCS	[M+H-H2O]+	163.1	32859911
AllCCS	[M+NH4]+	170.3	32859911
AllCCS	[M+Na]+	171.3	32859911
AllCCS	[M-H]-	168.6	32859911
AllCCS	[M+Na-2H]-	168.7	32859911
AllCCS	[M+HCOO]-	169.0	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. Predicted by Afia on May 17, 2022.	7.07 minutes	32390414
Predicted by Siyang on May 30, 2022	13.149 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.26 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	23.1 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2074.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	296.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	163.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	173.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	95.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	567.8 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	502.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	115.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1159.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	459.4 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	1377.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	302.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	384.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	377.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	220.6 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	65.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
11-Hydroxy-12-methoxydihydrokawain	COC1=CC(=O)OC(CCC2=CC(O)=C(OC)C=C2)C1	3755.9	Standard polar	33892256
11-Hydroxy-12-methoxydihydrokawain	COC1=CC(=O)OC(CCC2=CC(O)=C(OC)C=C2)C1	2393.3	Standard non polar	33892256
11-Hydroxy-12-methoxydihydrokawain	COC1=CC(=O)OC(CCC2=CC(O)=C(OC)C=C2)C1	2593.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
11-Hydroxy-12-methoxydihydrokawain,1TMS,isomer #1	COC1=CC(=O)OC(CCC2=CC=C(OC)C(O[Si](C)(C)C)=C2)C1	2465.6	Semi standard non polar	33892256
11-Hydroxy-12-methoxydihydrokawain,1TBDMS,isomer #1	COC1=CC(=O)OC(CCC2=CC=C(OC)C(O[Si](C)(C)C(C)(C)C)=C2)C1	2708.2	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-Hydroxy-12-methoxydihydrokawain GC-MS (Non-derivatized) - 70eV, Positive	splash10-052r-4950000000-6e36607046ee12d070d0	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 11-Hydroxy-12-methoxydihydrokawain GC-MS (1 TMS) - 70eV, Positive	splash10-0abl-9486000000-5c6c8da93d149916b48b	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 11-Hydroxy-12-methoxydihydrokawain GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 11-Hydroxy-12-methoxydihydrokawain 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 - 11-Hydroxy-12-methoxydihydrokawain 10V, Positive-QTOF	splash10-004i-0390000000-670c9eb8b6aa4fde42b0	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11-Hydroxy-12-methoxydihydrokawain 20V, Positive-QTOF	splash10-01t9-1930000000-4e3f0a6852806702f386	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11-Hydroxy-12-methoxydihydrokawain 40V, Positive-QTOF	splash10-0fi0-6900000000-3c1115a3db24bb00c2b4	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11-Hydroxy-12-methoxydihydrokawain 10V, Negative-QTOF	splash10-004i-0090000000-94c59b567aeb4e06ced5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11-Hydroxy-12-methoxydihydrokawain 20V, Negative-QTOF	splash10-0059-2190000000-361abb061c78195881f4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11-Hydroxy-12-methoxydihydrokawain 40V, Negative-QTOF	splash10-0536-9560000000-becf68791ede74160560	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11-Hydroxy-12-methoxydihydrokawain 10V, Negative-QTOF	splash10-0udi-0090000000-843bba1c44190e4fb795	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11-Hydroxy-12-methoxydihydrokawain 20V, Negative-QTOF	splash10-0udi-0390000000-445b18005208646e2413	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11-Hydroxy-12-methoxydihydrokawain 40V, Negative-QTOF	splash10-0079-2900000000-cbf35b287290d0c3461a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11-Hydroxy-12-methoxydihydrokawain 10V, Positive-QTOF	splash10-01ti-0490000000-f8a8aa1f471556052e14	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11-Hydroxy-12-methoxydihydrokawain 20V, Positive-QTOF	splash10-03di-0910000000-f30f7c7526e826f4e3ad	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11-Hydroxy-12-methoxydihydrokawain 40V, Positive-QTOF	splash10-01u3-2900000000-78e3503f50761bd9b91b	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

FDB002701

KNApSAcK ID

C00029378

Chemspider ID

509813

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

586508

PDB ID

Not Available

ChEBI ID

157724

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.. .

Enzymes

Enzyme Details

1. UDP-glucuronosyltransferase 1-1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:: UGT1A1
Uniprot ID:: P22309
Molecular weight:: 59590.91

Reactions

11-Hydroxy-12-methoxydihydrokawain → 3,4,5-trihydroxy-6-{2-methoxy-5-[2-(4-methoxy-6-oxo-3,6-dihydro-2H-pyran-2-yl)ethyl]phenoxy}oxane-2-carboxylic acid	details

Enzyme Details

2. Sulfotransferase 1A3

General function:: sulfotransferase activity
Specific function:: Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:: SULT1A3
Uniprot ID:: P0DMM9
Molecular weight:: 34195.96

Reactions

11-Hydroxy-12-methoxydihydrokawain → {2-methoxy-5-[2-(4-methoxy-6-oxo-3,6-dihydro-2H-pyran-2-yl)ethyl]phenyl}oxidanesulfonic acid	details

Showing metabocard for 11-Hydroxy-12-methoxydihydrokawain (HMDB0030766)

MOL for HMDB0030766 (11-Hydroxy-12-methoxydihydrokawain)

3D MOL for HMDB0030766 (11-Hydroxy-12-methoxydihydrokawain)

3D SDF for HMDB0030766 (11-Hydroxy-12-methoxydihydrokawain)

3D-SDF for HMDB0030766 (11-Hydroxy-12-methoxydihydrokawain)

PDB for HMDB0030766 (11-Hydroxy-12-methoxydihydrokawain)

3D PDB for HMDB0030766 (11-Hydroxy-12-methoxydihydrokawain)

SMILES for HMDB0030766 (11-Hydroxy-12-methoxydihydrokawain)

INCHI for HMDB0030766 (11-Hydroxy-12-methoxydihydrokawain)

Structure for HMDB0030766 (11-Hydroxy-12-methoxydihydrokawain)

3D Structure for HMDB0030766 (11-Hydroxy-12-methoxydihydrokawain)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions

Reactions