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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:38:50 UTC

Update Date

2022-03-07 02:52:41 UTC

HMDB ID

HMDB0030754

Secondary Accession Numbers

HMDB30754

Metabolite Identification

Common Name

11-Methoxynoryangonin

Description

11-Methoxynoryangonin 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-Methoxynoryangonin.

Structure

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

HMDB0030754
     RDKit          3D
11-Methoxynoryangonin
 34 35  0  0  0  0  0  0  0  0999 V2000
    3.9142    2.7757   -0.6777 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8209    1.9968   -0.2978 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8872    0.6600    0.0253 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7343   -0.0207    0.3907 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6634   -1.3354    0.7289 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5560   -2.1491    1.1031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6462   -2.0612    0.7092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2325   -1.1745   -0.2150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6588   -0.6108   -1.2879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2728    0.3321   -2.1181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5523    0.7212   -1.8363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2129    1.6677   -2.6426 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1901    0.1690   -0.7433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4890    0.5888   -0.4912 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1701    0.0468    0.6151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5498   -0.7555    0.0492 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8471   -1.9728    0.6896 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9589   -1.3844    0.3552 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0414   -2.0468    0.3384 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0625   -0.0552    0.0051 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1662    2.5548   -1.7335 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7922    2.6656   -0.0161 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6251    3.8470   -0.6476 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8530    0.5699    0.4531 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7419   -2.9945    1.8557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3643   -2.8228    1.1745 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3262   -0.9023   -1.6155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7353    0.7352   -2.9596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7025    2.0419   -3.4308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0902   -1.0715    0.5104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2424    0.3645    0.5930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7639    0.3563    1.5814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0880   -1.1672    0.9019 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9707    0.4316   -0.2705 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
 11 13  1  0
 13 14  1  0
 14 15  1  0
 13 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
 12 29  1  0
 15 30  1  0
 15 31  1  0
 15 32  1  0
 16 33  1  0
 20 34  1  0
M  END


  Mrv0541 05061305292D          

 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
    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
    2.8579    0.8250    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
    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
  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  6  1  0  0  0  0
 14  7  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>
HMDB0030754

> <DATABASE_NAME>
hmdb

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

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

> <INCHI_KEY>
YHVDGZPFCGLBOW-HYXAFXHYSA-N

> <FORMULA>
C15H14O5

> <MOLECULAR_WEIGHT>
274.2687

> <EXACT_MASS>
274.084123558

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
27.41376102512965

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.30

> <JCHEM_LOGP>
2.1782532876666663

> <ALOGPS_LOGS>
-3.86

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.929827691182952

> <JCHEM_PKA_STRONGEST_BASIC>
-4.558218149073936

> <JCHEM_POLAR_SURFACE_AREA>
64.99000000000001

> <JCHEM_REFRACTIVITY>
77.1848

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.78e-02 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030754
     RDKit          3D
11-Methoxynoryangonin
 34 35  0  0  0  0  0  0  0  0999 V2000
    3.9142    2.7757   -0.6777 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8209    1.9968   -0.2978 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8872    0.6600    0.0253 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7343   -0.0207    0.3907 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6634   -1.3354    0.7289 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5560   -2.1491    1.1031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6462   -2.0612    0.7092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2325   -1.1745   -0.2150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6588   -0.6108   -1.2879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2728    0.3321   -2.1181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5523    0.7212   -1.8363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2129    1.6677   -2.6426 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1901    0.1690   -0.7433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4890    0.5888   -0.4912 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1701    0.0468    0.6151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5498   -0.7555    0.0492 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8471   -1.9728    0.6896 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9589   -1.3844    0.3552 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0414   -2.0468    0.3384 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0625   -0.0552    0.0051 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1662    2.5548   -1.7335 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7922    2.6656   -0.0161 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6251    3.8470   -0.6476 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8530    0.5699    0.4531 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7419   -2.9945    1.8557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3643   -2.8228    1.1745 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3262   -0.9023   -1.6155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7353    0.7352   -2.9596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7025    2.0419   -3.4308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0902   -1.0715    0.5104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2424    0.3645    0.5930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7639    0.3563    1.5814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0880   -1.1672    0.9019 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9707    0.4316   -0.2705 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
 11 13  1  0
 13 14  1  0
 14 15  1  0
 13 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
 12 29  1  0
 15 30  1  0
 15 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       2.667   1.540   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       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001  -0.770   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       5.335   1.540   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       2.667   0.000   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   13                                                       
CONECT    7   10   14                                                       
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    6   14   16                                                  
CONECT   14    7   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    HMDB0030754
HETATM    1  C1  UNL     1       3.914   2.776  -0.678  1.00  0.00           C  
HETATM    2  O1  UNL     1       2.821   1.997  -0.298  1.00  0.00           O  
HETATM    3  C2  UNL     1       2.887   0.660   0.025  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.734  -0.021   0.391  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.663  -1.335   0.729  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.556  -2.149   1.103  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.646  -2.061   0.709  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.233  -1.174  -0.215  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.659  -0.611  -1.288  1.00  0.00           C  
HETATM   10  C9  UNL     1      -1.273   0.332  -2.118  1.00  0.00           C  
HETATM   11  C10 UNL     1      -2.552   0.721  -1.836  1.00  0.00           C  
HETATM   12  O2  UNL     1      -3.213   1.668  -2.643  1.00  0.00           O  
HETATM   13  C11 UNL     1      -3.190   0.169  -0.743  1.00  0.00           C  
HETATM   14  O3  UNL     1      -4.489   0.589  -0.491  1.00  0.00           O  
HETATM   15  C12 UNL     1      -5.170   0.047   0.615  1.00  0.00           C  
HETATM   16  C13 UNL     1      -2.550  -0.755   0.049  1.00  0.00           C  
HETATM   17  O4  UNL     1       2.847  -1.973   0.690  1.00  0.00           O  
HETATM   18  C14 UNL     1       3.959  -1.384   0.355  1.00  0.00           C  
HETATM   19  O5  UNL     1       5.041  -2.047   0.338  1.00  0.00           O  
HETATM   20  C15 UNL     1       4.063  -0.055   0.005  1.00  0.00           C  
HETATM   21  H1  UNL     1       4.166   2.555  -1.733  1.00  0.00           H  
HETATM   22  H2  UNL     1       4.792   2.666  -0.016  1.00  0.00           H  
HETATM   23  H3  UNL     1       3.625   3.847  -0.648  1.00  0.00           H  
HETATM   24  H4  UNL     1       0.853   0.570   0.453  1.00  0.00           H  
HETATM   25  H5  UNL     1       0.742  -2.995   1.856  1.00  0.00           H  
HETATM   26  H6  UNL     1      -1.364  -2.823   1.174  1.00  0.00           H  
HETATM   27  H7  UNL     1       0.326  -0.902  -1.616  1.00  0.00           H  
HETATM   28  H8  UNL     1      -0.735   0.735  -2.960  1.00  0.00           H  
HETATM   29  H9  UNL     1      -2.702   2.042  -3.431  1.00  0.00           H  
HETATM   30  H10 UNL     1      -5.090  -1.071   0.510  1.00  0.00           H  
HETATM   31  H11 UNL     1      -6.242   0.364   0.593  1.00  0.00           H  
HETATM   32  H12 UNL     1      -4.764   0.356   1.581  1.00  0.00           H  
HETATM   33  H13 UNL     1      -3.088  -1.167   0.902  1.00  0.00           H  
HETATM   34  H14 UNL     1       4.971   0.432  -0.271  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   13
CONECT   12   29
CONECT   13   14   16   16
CONECT   14   15
CONECT   15   30   31   32
CONECT   16   33
CONECT   17   18
CONECT   18   19   19   20
CONECT   20   34
END

HMDB0030754
     RDKit          3D
11-Methoxynoryangonin
 34 35  0  0  0  0  0  0  0  0999 V2000
    3.9142    2.7757   -0.6777 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8209    1.9968   -0.2978 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8872    0.6600    0.0253 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7343   -0.0207    0.3907 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6634   -1.3354    0.7289 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5560   -2.1491    1.1031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6462   -2.0612    0.7092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2325   -1.1745   -0.2150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6588   -0.6108   -1.2879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2728    0.3321   -2.1181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5523    0.7212   -1.8363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2129    1.6677   -2.6426 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1901    0.1690   -0.7433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4890    0.5888   -0.4912 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1701    0.0468    0.6151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5498   -0.7555    0.0492 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8471   -1.9728    0.6896 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9589   -1.3844    0.3552 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0414   -2.0468    0.3384 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0625   -0.0552    0.0051 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1662    2.5548   -1.7335 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7922    2.6656   -0.0161 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6251    3.8470   -0.6476 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8530    0.5699    0.4531 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7419   -2.9945    1.8557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3643   -2.8228    1.1745 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3262   -0.9023   -1.6155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7353    0.7352   -2.9596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7025    2.0419   -3.4308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0902   -1.0715    0.5104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2424    0.3645    0.5930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7639    0.3563    1.5814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0880   -1.1672    0.9019 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9707    0.4316   -0.2705 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
 11 13  1  0
 13 14  1  0
 14 15  1  0
 13 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
 12 29  1  0
 15 30  1  0
 15 31  1  0
 15 32  1  0
 16 33  1  0
 20 34  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
6-(4-Hydroxy-3-methoxystyryl)-4-methoxy-2-pyrone	HMDB
6-[2-(4-Hydroxy-3-methoxyphenyl)ethenyl]-4-methoxy-2H-pyran-2-one	HMDB

Chemical Formula

C₁₅H₁₄O₅

Average Molecular Weight

274.2687

Monoisotopic Molecular Weight

274.084123558

IUPAC Name

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

Traditional Name

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

CAS Registry Number

77900-31-3

SMILES

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

InChI Identifier

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

InChI Key

YHVDGZPFCGLBOW-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
Styrene
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Pyranone
Phenol
Monocyclic benzene moiety
Benzenoid
Pyran
Heteroaromatic compound
Vinylogous ester
Lactone
Organoheterocyclic compound
Oxacycle
Ether
Organic oxygen compound
Hydrocarbon derivative
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

Extracellular (HMDB: HMDB0030754)
Cytoplasm (HMDB: HMDB0030754)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030754)

Source

Endogenous

Endogenous (HMDB: HMDB0030754)

Plant

Plant (HMDB: HMDB0030754)

Exogenous

Food

Food (HMDB: HMDB0030754)

Fruit

Fruits (FooDB: FOOD00871)

Exogenous (HMDB: HMDB0030754)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	218 - 219 °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	0.038 g/L	ALOGPS
logP	2.3	ALOGPS
logP	2.18	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	9.93	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	27.41 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]+	166.073	31661259
DarkChem	[M-H]-	167.284	31661259
DeepCCS	[M+H]+	168.126	30932474
DeepCCS	[M-H]-	165.768	30932474
DeepCCS	[M-2H]-	198.654	30932474
DeepCCS	[M+Na]+	174.22	30932474
AllCCS	[M+H]+	162.2	32859911
AllCCS	[M+H-H2O]+	158.2	32859911
AllCCS	[M+NH4]+	165.9	32859911
AllCCS	[M+Na]+	166.9	32859911
AllCCS	[M-H]-	163.0	32859911
AllCCS	[M+Na-2H]-	162.6	32859911
AllCCS	[M+HCOO]-	162.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
11-Methoxynoryangonin	COC1=CC(=O)OC(\C=C/C2=CC(OC)=C(O)C=C2)=C1	4169.2	Standard polar	33892256
11-Methoxynoryangonin	COC1=CC(=O)OC(\C=C/C2=CC(OC)=C(O)C=C2)=C1	2580.7	Standard non polar	33892256
11-Methoxynoryangonin	COC1=CC(=O)OC(\C=C/C2=CC(OC)=C(O)C=C2)=C1	2823.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
11-Methoxynoryangonin,1TMS,isomer #1	COC1=CC(=O)OC(/C=C\C2=CC=C(O[Si](C)(C)C)C(OC)=C2)=C1	2757.7	Semi standard non polar	33892256
11-Methoxynoryangonin,1TBDMS,isomer #1	COC1=CC(=O)OC(/C=C\C2=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C2)=C1	3022.2	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-Methoxynoryangonin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0597-0390000000-0bba325b7ce3f9f519e5	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 11-Methoxynoryangonin GC-MS (1 TMS) - 70eV, Positive	splash10-00e9-5049000000-13a69761c4f5abcc1b14	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 11-Methoxynoryangonin 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-Methoxynoryangonin 10V, Positive-QTOF	splash10-004i-0090000000-1734edb38ae234f76470	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11-Methoxynoryangonin 20V, Positive-QTOF	splash10-004i-0290000000-54b43e43e252fcb86531	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11-Methoxynoryangonin 40V, Positive-QTOF	splash10-0fb9-2970000000-f9eba4df481664246fe8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11-Methoxynoryangonin 10V, Negative-QTOF	splash10-00di-0090000000-1ba3bb829e0583c162ea	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11-Methoxynoryangonin 20V, Negative-QTOF	splash10-00di-1090000000-6cfad98334cb8a67dc5c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11-Methoxynoryangonin 40V, Negative-QTOF	splash10-0597-8940000000-f496e33e9e31734ed036	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11-Methoxynoryangonin 10V, Negative-QTOF	splash10-006t-0970000000-0fefc7e7b2742fdd741c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11-Methoxynoryangonin 20V, Negative-QTOF	splash10-0002-0930000000-1f0971f9fd11132e7c7e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11-Methoxynoryangonin 40V, Negative-QTOF	splash10-053u-2910000000-fbd4d8397fa07f7b4c30	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11-Methoxynoryangonin 10V, Positive-QTOF	splash10-004i-0090000000-b9fdc733d37929ef1045	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11-Methoxynoryangonin 20V, Positive-QTOF	splash10-01tc-0590000000-9430285ce27e7c1ac0ea	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11-Methoxynoryangonin 40V, Positive-QTOF	splash10-00b9-1910000000-36ec63899e0d5610b685	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

FDB002686

KNApSAcK ID

Not Available

Chemspider ID

30776851

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131751080

PDB ID

Not Available

ChEBI ID

174603

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-Methoxynoryangonin (HMDB0030754)

MOL for HMDB0030754 (11-Methoxynoryangonin)

3D MOL for HMDB0030754 (11-Methoxynoryangonin)

3D SDF for HMDB0030754 (11-Methoxynoryangonin)

3D-SDF for HMDB0030754 (11-Methoxynoryangonin)

PDB for HMDB0030754 (11-Methoxynoryangonin)

3D PDB for HMDB0030754 (11-Methoxynoryangonin)

SMILES for HMDB0030754 (11-Methoxynoryangonin)

INCHI for HMDB0030754 (11-Methoxynoryangonin)

Structure for HMDB0030754 (11-Methoxynoryangonin)

3D Structure for HMDB0030754 (11-Methoxynoryangonin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra