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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:53:16 UTC

Update Date

2022-03-07 02:53:33 UTC

HMDB ID

HMDB0033017

Secondary Accession Numbers

HMDB33017

Metabolite Identification

Common Name

11-Hydroxyyangonin

Description

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

Structure

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

HMDB0033017
     RDKit          3D
11-Hydroxyyangonin
 34 35  0  0  0  0  0  0  0  0999 V2000
    5.7630   -0.9347    0.4987 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8820   -1.3585   -0.5331 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5766   -0.9371   -0.5483 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0886   -0.0999    0.4265 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7451    0.3195    0.3914 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3277    1.1891    1.4250 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1110    1.4863    1.7210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1032    1.0091    1.1121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3562   -0.1988    0.5412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5548   -0.4818   -0.1246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5580    0.4475   -0.2403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7348    0.1410   -0.9049 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9103   -1.1435   -1.4731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3274    1.6749    0.3320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3236    2.6555    0.2412 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1517    1.9530    0.9832 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0769   -0.1484   -0.6020 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4591   -0.9310   -1.5487 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6434   -1.2872   -2.4514 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7556   -1.3715   -1.5660 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7483    0.1781    0.6050 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8043   -1.2446    0.2804 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4558   -1.3732    1.4713 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7606    0.2234    1.2132 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1023    1.6768    2.0518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0489    2.2202    2.5828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6460   -1.0243    0.6599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6826   -1.4691   -0.5580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9450   -1.3110   -1.8098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1947   -1.3228   -2.3182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6610   -1.9401   -0.7119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1897    2.5040   -0.2182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9727    2.9228    1.4333 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0606   -2.0239   -2.3615 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 11 14  1  0
 14 15  1  0
 14 16  2  0
  5 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20  3  2  0
 16  8  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  6 25  1  0
  7 26  1  0
  9 27  1  0
 10 28  1  0
 13 29  1  0
 13 30  1  0
 13 31  1  0
 15 32  1  0
 16 33  1  0
 20 34  1  0
M  END


  Mrv0541 05061306512D          

 20 21  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
    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
    2.1434   -0.4125    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
    0.7145   -1.2375    0.0000 C   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
    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   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  3  2  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  2  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>
HMDB0033017

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C15H14O5/c1-18-12-8-11(20-15(17)9-12)5-3-10-4-6-14(19-2)13(16)7-10/h3-9,16H,1-2H3/b5-3-

> <INCHI_KEY>
OCZUPEYJZNWTBK-HYXAFXHYSA-N

> <FORMULA>
C15H14O5

> <MOLECULAR_WEIGHT>
274.2687

> <EXACT_MASS>
274.084123558

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
27.60201226319731

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-[(Z)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]-4-methoxy-2H-pyran-2-one

> <ALOGPS_LOGP>
2.33

> <JCHEM_LOGP>
2.1782532876666663

> <ALOGPS_LOGS>
-3.81

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.835690226246456

> <JCHEM_PKA_STRONGEST_BASIC>
-4.556035544683389

> <JCHEM_POLAR_SURFACE_AREA>
64.99000000000001

> <JCHEM_REFRACTIVITY>
77.1848

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.26e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-[(Z)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]-4-methoxypyran-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0033017
     RDKit          3D
11-Hydroxyyangonin
 34 35  0  0  0  0  0  0  0  0999 V2000
    5.7630   -0.9347    0.4987 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8820   -1.3585   -0.5331 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5766   -0.9371   -0.5483 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0886   -0.0999    0.4265 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7451    0.3195    0.3914 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3277    1.1891    1.4250 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1110    1.4863    1.7210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1032    1.0091    1.1121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3562   -0.1988    0.5412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5548   -0.4818   -0.1246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5580    0.4475   -0.2403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7348    0.1410   -0.9049 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9103   -1.1435   -1.4731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3274    1.6749    0.3320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3236    2.6555    0.2412 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1517    1.9530    0.9832 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0769   -0.1484   -0.6020 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4591   -0.9310   -1.5487 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6434   -1.2872   -2.4514 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7556   -1.3715   -1.5660 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7483    0.1781    0.6050 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8043   -1.2446    0.2804 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4558   -1.3732    1.4713 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7606    0.2234    1.2132 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1023    1.6768    2.0518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0489    2.2202    2.5828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6460   -1.0243    0.6599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6826   -1.4691   -0.5580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9450   -1.3110   -1.8098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1947   -1.3228   -2.3182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6610   -1.9401   -0.7119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1897    2.5040   -0.2182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9727    2.9228    1.4333 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0606   -2.0239   -2.3615 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 11 14  1  0
 14 15  1  0
 14 16  2  0
  5 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20  3  2  0
 16  8  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  6 25  1  0
  7 26  1  0
  9 27  1  0
 10 28  1  0
 13 29  1  0
 13 30  1  0
 13 31  1  0
 15 32  1  0
 16 33  1  0
 20 34  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       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001  -0.770   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       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+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  -3.080   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    HMDB0033017
HETATM    1  C1  UNL     1       5.763  -0.935   0.499  1.00  0.00           C  
HETATM    2  O1  UNL     1       4.882  -1.359  -0.533  1.00  0.00           O  
HETATM    3  C2  UNL     1       3.577  -0.937  -0.548  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.089  -0.100   0.427  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.745   0.319   0.391  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.328   1.189   1.425  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.111   1.486   1.721  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.103   1.009   1.112  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.356  -0.199   0.541  1.00  0.00           C  
HETATM   10  C9  UNL     1      -2.555  -0.482  -0.125  1.00  0.00           C  
HETATM   11  C10 UNL     1      -3.558   0.447  -0.240  1.00  0.00           C  
HETATM   12  O2  UNL     1      -4.735   0.141  -0.905  1.00  0.00           O  
HETATM   13  C11 UNL     1      -4.910  -1.143  -1.473  1.00  0.00           C  
HETATM   14  C12 UNL     1      -3.327   1.675   0.332  1.00  0.00           C  
HETATM   15  O3  UNL     1      -4.324   2.655   0.241  1.00  0.00           O  
HETATM   16  C13 UNL     1      -2.152   1.953   0.983  1.00  0.00           C  
HETATM   17  O4  UNL     1       1.077  -0.148  -0.602  1.00  0.00           O  
HETATM   18  C14 UNL     1       1.459  -0.931  -1.549  1.00  0.00           C  
HETATM   19  O5  UNL     1       0.643  -1.287  -2.451  1.00  0.00           O  
HETATM   20  C15 UNL     1       2.756  -1.371  -1.566  1.00  0.00           C  
HETATM   21  H1  UNL     1       5.748   0.178   0.605  1.00  0.00           H  
HETATM   22  H2  UNL     1       6.804  -1.245   0.280  1.00  0.00           H  
HETATM   23  H3  UNL     1       5.456  -1.373   1.471  1.00  0.00           H  
HETATM   24  H4  UNL     1       3.761   0.223   1.213  1.00  0.00           H  
HETATM   25  H5  UNL     1       2.102   1.677   2.052  1.00  0.00           H  
HETATM   26  H6  UNL     1      -0.049   2.220   2.583  1.00  0.00           H  
HETATM   27  H7  UNL     1      -0.646  -1.024   0.660  1.00  0.00           H  
HETATM   28  H8  UNL     1      -2.683  -1.469  -0.558  1.00  0.00           H  
HETATM   29  H9  UNL     1      -5.945  -1.311  -1.810  1.00  0.00           H  
HETATM   30  H10 UNL     1      -4.195  -1.323  -2.318  1.00  0.00           H  
HETATM   31  H11 UNL     1      -4.661  -1.940  -0.712  1.00  0.00           H  
HETATM   32  H12 UNL     1      -5.190   2.504  -0.218  1.00  0.00           H  
HETATM   33  H13 UNL     1      -1.973   2.923   1.433  1.00  0.00           H  
HETATM   34  H14 UNL     1       3.061  -2.024  -2.361  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3
CONECT    3    4   20   20
CONECT    4    5    5   24
CONECT    5    6   17
CONECT    6    7    7   25
CONECT    7    8   26
CONECT    8    9    9   16
CONECT    9   10   27
CONECT   10   11   11   28
CONECT   11   12   14
CONECT   12   13
CONECT   13   29   30   31
CONECT   14   15   16   16
CONECT   15   32
CONECT   16   33
CONECT   17   18
CONECT   18   19   19   20
CONECT   20   34
END

HMDB0033017
     RDKit          3D
11-Hydroxyyangonin
 34 35  0  0  0  0  0  0  0  0999 V2000
    5.7630   -0.9347    0.4987 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8820   -1.3585   -0.5331 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5766   -0.9371   -0.5483 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0886   -0.0999    0.4265 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7451    0.3195    0.3914 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3277    1.1891    1.4250 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1110    1.4863    1.7210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1032    1.0091    1.1121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3562   -0.1988    0.5412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5548   -0.4818   -0.1246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5580    0.4475   -0.2403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7348    0.1410   -0.9049 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9103   -1.1435   -1.4731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3274    1.6749    0.3320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3236    2.6555    0.2412 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1517    1.9530    0.9832 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0769   -0.1484   -0.6020 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4591   -0.9310   -1.5487 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6434   -1.2872   -2.4514 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7556   -1.3715   -1.5660 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7483    0.1781    0.6050 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8043   -1.2446    0.2804 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4558   -1.3732    1.4713 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7606    0.2234    1.2132 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1023    1.6768    2.0518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0489    2.2202    2.5828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6460   -1.0243    0.6599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6826   -1.4691   -0.5580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9450   -1.3110   -1.8098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1947   -1.3228   -2.3182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6610   -1.9401   -0.7119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1897    2.5040   -0.2182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9727    2.9228    1.4333 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0606   -2.0239   -2.3615 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 11 14  1  0
 14 15  1  0
 14 16  2  0
  5 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20  3  2  0
 16  8  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  6 25  1  0
  7 26  1  0
  9 27  1  0
 10 28  1  0
 13 29  1  0
 13 30  1  0
 13 31  1  0
 15 32  1  0
 16 33  1  0
 20 34  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₅H₁₄O₅

Average Molecular Weight

274.2687

Monoisotopic Molecular Weight

274.084123558

IUPAC Name

6-[(Z)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]-4-methoxy-2H-pyran-2-one

Traditional Name

6-[(Z)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]-4-methoxypyran-2-one

CAS Registry Number

77900-30-2

SMILES

COC1=CC(=O)OC(\C=C/C2=CC(O)=C(OC)C=C2)=C1

InChI Identifier

InChI=1S/C15H14O5/c1-18-12-8-11(20-15(17)9-12)5-3-10-4-6-14(19-2)13(16)7-10/h3-9,16H,1-2H3/b5-3-

InChI Key

OCZUPEYJZNWTBK-HYXAFXHYSA-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
Methoxybenzene
Phenol ether
Styrene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Pyranone
Monocyclic benzene moiety
Benzenoid
Pyran
Heteroaromatic compound
Vinylogous ester
Lactone
Oxacycle
Ether
Organoheterocyclic compound
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0033017)
Cytoplasm (HMDB: HMDB0033017)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033017)

Source

Exogenous

Food

Food (HMDB: HMDB0033017)

Beverage

Beverages (FooDB: FOOD00870)

Endogenous

Plant

Plant (HMDB: HMDB0033017)

Not Available

Nutrient (HMDB: HMDB0033017)

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	0.043 g/L	ALOGPS
logP	2.33	ALOGPS
logP	2.18	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	9.84	ChemAxon
pKa (Strongest Basic)	-4.6	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	4	ChemAxon
Refractivity	77.18 m³·mol⁻¹	ChemAxon
Polarizability	27.6 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
DeepCCS	[M+H]+	167.798	30932474
DeepCCS	[M-H]-	165.44	30932474
DeepCCS	[M-2H]-	198.326	30932474
DeepCCS	[M+Na]+	173.892	30932474
AllCCS	[M+H]+	162.7	32859911
AllCCS	[M+H-H2O]+	158.7	32859911
AllCCS	[M+NH4]+	166.3	32859911
AllCCS	[M+Na]+	167.4	32859911
AllCCS	[M-H]-	163.4	32859911
AllCCS	[M+Na-2H]-	163.1	32859911
AllCCS	[M+HCOO]-	162.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
11-Hydroxyyangonin	COC1=CC(=O)OC(\C=C/C2=CC(O)=C(OC)C=C2)=C1	4193.3	Standard polar	33892256
11-Hydroxyyangonin	COC1=CC(=O)OC(\C=C/C2=CC(O)=C(OC)C=C2)=C1	2593.6	Standard non polar	33892256
11-Hydroxyyangonin	COC1=CC(=O)OC(\C=C/C2=CC(O)=C(OC)C=C2)=C1	2839.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
11-Hydroxyyangonin,1TMS,isomer #1	COC1=CC(=O)OC(/C=C\C2=CC=C(OC)C(O[Si](C)(C)C)=C2)=C1	2743.8	Semi standard non polar	33892256
11-Hydroxyyangonin,1TBDMS,isomer #1	COC1=CC(=O)OC(/C=C\C2=CC=C(OC)C(O[Si](C)(C)C(C)(C)C)=C2)=C1	3009.4	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-Hydroxyyangonin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0597-1390000000-8df5c7231b1200cb3e15	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 11-Hydroxyyangonin GC-MS (1 TMS) - 70eV, Positive	splash10-00e9-5049000000-d4c101bd02905ef692da	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 11-Hydroxyyangonin 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-Hydroxyyangonin 10V, Positive-QTOF	splash10-004i-0090000000-0e39fd1dd5b41be4912f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11-Hydroxyyangonin 20V, Positive-QTOF	splash10-004i-1490000000-cdc2709515fdbd681996	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11-Hydroxyyangonin 40V, Positive-QTOF	splash10-0fk9-2940000000-3cfb7d3cbaf495508bc6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11-Hydroxyyangonin 10V, Negative-QTOF	splash10-00di-0090000000-edb06adfc809030ca22b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11-Hydroxyyangonin 20V, Negative-QTOF	splash10-00di-1090000000-569b7668b7c0f510a218	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11-Hydroxyyangonin 40V, Negative-QTOF	splash10-0596-7930000000-648cc0a392e378b532d8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11-Hydroxyyangonin 10V, Positive-QTOF	splash10-004i-0090000000-bcc15c1fdc40e7e6f611	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11-Hydroxyyangonin 20V, Positive-QTOF	splash10-004i-0590000000-4ab2cf707bd509ac93d4	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11-Hydroxyyangonin 40V, Positive-QTOF	splash10-00b9-3910000000-f317e44b298cc5a35263	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11-Hydroxyyangonin 10V, Negative-QTOF	splash10-00di-0090000000-7dbb1e549f6404042b70	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11-Hydroxyyangonin 20V, Negative-QTOF	splash10-00dj-0980000000-f0d034da8fcd1938d6fb	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11-Hydroxyyangonin 40V, Negative-QTOF	splash10-001i-1900000000-545cc9797f3b3eef2daf	2021-09-25	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

FDB011009

KNApSAcK ID

Not Available

Chemspider ID

30776966

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131751359

PDB ID

Not Available

ChEBI ID

174605

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 11-Hydroxyyangonin (HMDB0033017)

MOL for HMDB0033017 (11-Hydroxyyangonin)

3D MOL for HMDB0033017 (11-Hydroxyyangonin)

3D SDF for HMDB0033017 (11-Hydroxyyangonin)

3D-SDF for HMDB0033017 (11-Hydroxyyangonin)

PDB for HMDB0033017 (11-Hydroxyyangonin)

3D PDB for HMDB0033017 (11-Hydroxyyangonin)

SMILES for HMDB0033017 (11-Hydroxyyangonin)

INCHI for HMDB0033017 (11-Hydroxyyangonin)

Structure for HMDB0033017 (11-Hydroxyyangonin)

3D Structure for HMDB0033017 (11-Hydroxyyangonin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra