Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 06:50:30 UTC

Update Date

2021-09-23 06:50:30 UTC

HMDB ID

HMDB0302127

Secondary Accession Numbers

None

Metabolite Identification

Common Name

[4]-Shogaol

Description

[4]-shogaol is a member of the class of compounds known as shogaols. Shogaols are ginger derivatives containing a shogaol moiety, which consists of a benzene ring bearing a dec-4-en-3-one moiety, a methoxyphenyl group, a hydroxyl group and at positions 1, 3, and 4, respectively. [4]-shogaol is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). [4]-shogaol can be found in ginger, which makes [4]-shogaol a potential biomarker for the consumption of this food product.

Structure

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

HMDB0302127
     RDKit          3D
[4]-Shogaol
 38 38  0  0  0  0  0  0  0  0999 V2000
    4.5209   -0.6402    1.8690 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3708   -1.0268    0.6949 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5333   -1.4573   -0.4961 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6337   -0.3877   -0.9509 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3281   -0.5392   -0.9691 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5038    0.5577   -1.4294 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0114    1.6408   -1.8077 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0332    0.3946   -1.4521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5855    1.3146   -0.4120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0432    1.2093   -0.3749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8542    2.0085   -1.1276 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2451    1.8996   -1.0884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8370    0.9655   -0.2741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2199    0.8097   -0.1927 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0066    0.1498    0.4939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6360   -0.7839    1.3047 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9061   -1.6687    2.1265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6307    0.2708    0.4436 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8579    0.3355    2.3294 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4583   -0.4626    1.5897 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6489   -1.3982    2.6629 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0916   -1.8392    0.9239 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9784   -0.1369    0.4083 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2148   -1.8444   -1.2806 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9076   -2.3396   -0.1900 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0504    0.5486   -1.2793 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8753   -1.4617   -0.6488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2454   -0.6503   -1.2478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3041    0.6339   -2.4820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1132    1.0450    0.5620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2086    2.3363   -0.6488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3975    2.7456   -1.7716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8822    2.5412   -1.6915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7785    1.4238   -0.7698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5316   -2.5707    2.3420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5843   -1.1932    3.0792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0139   -2.0515    1.5968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9947   -0.3783    1.0547 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
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 15 18  2  0
 18 10  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  5 27  1  0
  8 28  1  0
  8 29  1  0
  9 30  1  0
  9 31  1  0
 11 32  1  0
 12 33  1  0
 14 34  1  0
 17 35  1  0
 17 36  1  0
 17 37  1  0
 18 38  1  0
M  END


  Mrv0541 02241212282D          

 18 18  0  0  0  0            999 V2000
   -4.4786    1.8268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1930    1.4143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1930    0.5893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4786    0.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7641    0.5893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7641    1.4143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9075    0.1768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4786   -0.6482    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7641   -1.0607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0496    1.8268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3352    1.4143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6207    1.8268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9062    1.4143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1918    1.8268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5227    1.4143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2372    1.8268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9517    1.4143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6207    2.6518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  3  7  1  0  0  0  0
  4  8  1  0  0  0  0
  8  9  1  0  0  0  0
  6 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 12 18  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0302127

> <DATABASE_NAME>
hmdb

> <SMILES>
CCC\C=C\C(=O)CCC1=CC(OC)=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O3/c1-3-4-5-6-13(16)9-7-12-8-10-14(17)15(11-12)18-2/h5-6,8,10-11,17H,3-4,7,9H2,1-2H3/b6-5+

> <INCHI_KEY>
PHHDVGGCTAPBHF-AATRIKPKSA-N

> <FORMULA>
C15H20O3

> <MOLECULAR_WEIGHT>
248.3175

> <EXACT_MASS>
248.141244506

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
28.71611292427577

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4E)-1-(4-hydroxy-3-methoxyphenyl)oct-4-en-3-one

> <ALOGPS_LOGP>
3.85

> <JCHEM_LOGP>
3.9560170373333334

> <ALOGPS_LOGS>
-3.78

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.945866637773328

> <JCHEM_PKA_STRONGEST_BASIC>
-4.453301819738214

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
73.485

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.10e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4E)-1-(4-hydroxy-3-methoxyphenyl)oct-4-en-3-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0302127
     RDKit          3D
[4]-Shogaol
 38 38  0  0  0  0  0  0  0  0999 V2000
    4.5209   -0.6402    1.8690 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3708   -1.0268    0.6949 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5333   -1.4573   -0.4961 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6337   -0.3877   -0.9509 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3281   -0.5392   -0.9691 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5038    0.5577   -1.4294 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0114    1.6408   -1.8077 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0332    0.3946   -1.4521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5855    1.3146   -0.4120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0432    1.2093   -0.3749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8542    2.0085   -1.1276 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2451    1.8996   -1.0884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8370    0.9655   -0.2741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2199    0.8097   -0.1927 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0066    0.1498    0.4939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6360   -0.7839    1.3047 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9061   -1.6687    2.1265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6307    0.2708    0.4436 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8579    0.3355    2.3294 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4583   -0.4626    1.5897 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6489   -1.3982    2.6629 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0916   -1.8392    0.9239 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9784   -0.1369    0.4083 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2148   -1.8444   -1.2806 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9076   -2.3396   -0.1900 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0504    0.5486   -1.2793 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8753   -1.4617   -0.6488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2454   -0.6503   -1.2478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3041    0.6339   -2.4820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1132    1.0450    0.5620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2086    2.3363   -0.6488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3975    2.7456   -1.7716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8822    2.5412   -1.6915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7785    1.4238   -0.7698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5316   -2.5707    2.3420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5843   -1.1932    3.0792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0139   -2.0515    1.5968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9947   -0.3783    1.0547 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
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 15 18  2  0
 18 10  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  5 27  1  0
  8 28  1  0
  8 29  1  0
  9 30  1  0
  9 31  1  0
 11 32  1  0
 12 33  1  0
 14 34  1  0
 17 35  1  0
 17 36  1  0
 17 37  1  0
 18 38  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -8.360   3.410   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -9.694   2.640   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -9.694   1.100   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -8.360   0.330   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -7.026   1.100   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -7.026   2.640   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0     -11.027   0.330   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      -8.360  -1.210   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -7.026  -1.980   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.693   3.410   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.359   2.640   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.025   3.410   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.692   2.640   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.358   3.410   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.976   2.640   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.309   3.410   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.643   2.640   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -3.025   4.950   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    7                                                  
CONECT    4    3    5    8                                                  
CONECT    5    4    6                                                       
CONECT    6    1    5   10                                                  
CONECT    7    3                                                            
CONECT    8    4    9                                                       
CONECT    9    8                                                            
CONECT   10    6   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   18                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16                                                            
CONECT   18   12                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   36    0
END

COMPND    HMDB0302127
HETATM    1  C1  UNL     1       4.521  -0.640   1.869  1.00  0.00           C  
HETATM    2  C2  UNL     1       5.371  -1.027   0.695  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.533  -1.457  -0.496  1.00  0.00           C  
HETATM    4  C4  UNL     1       3.634  -0.388  -0.951  1.00  0.00           C  
HETATM    5  C5  UNL     1       2.328  -0.539  -0.969  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.504   0.558  -1.429  1.00  0.00           C  
HETATM    7  O1  UNL     1       2.011   1.641  -1.808  1.00  0.00           O  
HETATM    8  C7  UNL     1       0.033   0.395  -1.452  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.585   1.315  -0.412  1.00  0.00           C  
HETATM   10  C9  UNL     1      -2.043   1.209  -0.375  1.00  0.00           C  
HETATM   11  C10 UNL     1      -2.854   2.008  -1.128  1.00  0.00           C  
HETATM   12  C11 UNL     1      -4.245   1.900  -1.088  1.00  0.00           C  
HETATM   13  C12 UNL     1      -4.837   0.965  -0.274  1.00  0.00           C  
HETATM   14  O2  UNL     1      -6.220   0.810  -0.193  1.00  0.00           O  
HETATM   15  C13 UNL     1      -4.007   0.150   0.494  1.00  0.00           C  
HETATM   16  O3  UNL     1      -4.636  -0.784   1.305  1.00  0.00           O  
HETATM   17  C14 UNL     1      -3.906  -1.669   2.127  1.00  0.00           C  
HETATM   18  C15 UNL     1      -2.631   0.271   0.444  1.00  0.00           C  
HETATM   19  H1  UNL     1       4.858   0.336   2.329  1.00  0.00           H  
HETATM   20  H2  UNL     1       3.458  -0.463   1.590  1.00  0.00           H  
HETATM   21  H3  UNL     1       4.649  -1.398   2.663  1.00  0.00           H  
HETATM   22  H4  UNL     1       6.092  -1.839   0.924  1.00  0.00           H  
HETATM   23  H5  UNL     1       5.978  -0.137   0.408  1.00  0.00           H  
HETATM   24  H6  UNL     1       5.215  -1.844  -1.281  1.00  0.00           H  
HETATM   25  H7  UNL     1       3.908  -2.340  -0.190  1.00  0.00           H  
HETATM   26  H8  UNL     1       4.050   0.549  -1.279  1.00  0.00           H  
HETATM   27  H9  UNL     1       1.875  -1.462  -0.649  1.00  0.00           H  
HETATM   28  H10 UNL     1      -0.245  -0.650  -1.248  1.00  0.00           H  
HETATM   29  H11 UNL     1      -0.304   0.634  -2.482  1.00  0.00           H  
HETATM   30  H12 UNL     1      -0.113   1.045   0.562  1.00  0.00           H  
HETATM   31  H13 UNL     1      -0.209   2.336  -0.649  1.00  0.00           H  
HETATM   32  H14 UNL     1      -2.397   2.746  -1.772  1.00  0.00           H  
HETATM   33  H15 UNL     1      -4.882   2.541  -1.691  1.00  0.00           H  
HETATM   34  H16 UNL     1      -6.778   1.424  -0.770  1.00  0.00           H  
HETATM   35  H17 UNL     1      -4.532  -2.571   2.342  1.00  0.00           H  
HETATM   36  H18 UNL     1      -3.584  -1.193   3.079  1.00  0.00           H  
HETATM   37  H19 UNL     1      -3.014  -2.051   1.597  1.00  0.00           H  
HETATM   38  H20 UNL     1      -1.995  -0.378   1.055  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3   22   23
CONECT    3    4   24   25
CONECT    4    5    5   26
CONECT    5    6   27
CONECT    6    7    7    8
CONECT    8    9   28   29
CONECT    9   10   30   31
CONECT   10   11   11   18
CONECT   11   12   32
CONECT   12   13   13   33
CONECT   13   14   15
CONECT   14   34
CONECT   15   16   18   18
CONECT   16   17
CONECT   17   35   36   37
CONECT   18   38
END

HMDB0302127
     RDKit          3D
[4]-Shogaol
 38 38  0  0  0  0  0  0  0  0999 V2000
    4.5209   -0.6402    1.8690 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3708   -1.0268    0.6949 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5333   -1.4573   -0.4961 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6337   -0.3877   -0.9509 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3281   -0.5392   -0.9691 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5038    0.5577   -1.4294 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0114    1.6408   -1.8077 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0332    0.3946   -1.4521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5855    1.3146   -0.4120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0432    1.2093   -0.3749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8542    2.0085   -1.1276 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2451    1.8996   -1.0884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8370    0.9655   -0.2741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2199    0.8097   -0.1927 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0066    0.1498    0.4939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6360   -0.7839    1.3047 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9061   -1.6687    2.1265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6307    0.2708    0.4436 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8579    0.3355    2.3294 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4583   -0.4626    1.5897 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6489   -1.3982    2.6629 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0916   -1.8392    0.9239 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9784   -0.1369    0.4083 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2148   -1.8444   -1.2806 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9076   -2.3396   -0.1900 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0504    0.5486   -1.2793 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8753   -1.4617   -0.6488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2454   -0.6503   -1.2478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3041    0.6339   -2.4820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1132    1.0450    0.5620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2086    2.3363   -0.6488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3975    2.7456   -1.7716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8822    2.5412   -1.6915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7785    1.4238   -0.7698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5316   -2.5707    2.3420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5843   -1.1932    3.0792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0139   -2.0515    1.5968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9947   -0.3783    1.0547 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
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 15 18  2  0
 18 10  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  5 27  1  0
  8 28  1  0
  8 29  1  0
  9 30  1  0
  9 31  1  0
 11 32  1  0
 12 33  1  0
 14 34  1  0
 17 35  1  0
 17 36  1  0
 17 37  1  0
 18 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₅H₂₀O₃

Average Molecular Weight

248.3175

Monoisotopic Molecular Weight

248.141244506

IUPAC Name

(4E)-1-(4-hydroxy-3-methoxyphenyl)oct-4-en-3-one

Traditional Name

(4E)-1-(4-hydroxy-3-methoxyphenyl)oct-4-en-3-one

CAS Registry Number

Not Available

SMILES

CCC\C=C\C(=O)CCC1=CC(OC)=C(O)C=C1

InChI Identifier

InChI=1S/C15H20O3/c1-3-4-5-6-13(16)9-7-12-8-10-14(17)15(11-12)18-2/h5-6,8,10-11,17H,3-4,7,9H2,1-2H3/b6-5+

InChI Key

PHHDVGGCTAPBHF-AATRIKPKSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as shogaols. These are ginger derivatives containing a shogaol moiety, which consists of a benzene ring bearing a dec-4-en-3-one moiety, a methoxyphenyl group, a hydroxyl group and at positions 1, 3, and 4, respectively.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Shogaol
Phenoxy compound
Anisole
Phenol ether
Methoxybenzene
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Monocyclic benzene moiety
Enone
Acryloyl-group
Alpha,beta-unsaturated ketone
Ketone
Ether
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Organic oxide
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Ginger (FooDB: FOOD00206)

Process

Not Available

Role

Not Available

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
logP	3.85	ALOGPS
logP	3.96	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	9.95	ChemAxon
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	73.48 m³·mol⁻¹	ChemAxon
Polarizability	28.72 Å³	ChemAxon
Number of Rings	1	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
AllCCS	[M+H]+	161.008	32859911
AllCCS	[M+H-H2O]+	157.301	32859911
AllCCS	[M+Na]+	165.444	32859911
AllCCS	[M+NH4]+	164.453	32859911
AllCCS	[M-H]-	163.429	32859911
AllCCS	[M+Na-2H]-	163.946	32859911
AllCCS	[M+HCOO]-	164.638	32859911
DeepCCS	[M+H]+	164.182	30932474
DeepCCS	[M-H]-	161.824	30932474
DeepCCS	[M-2H]-	194.71	30932474
DeepCCS	[M+Na]+	170.275	30932474

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
[4]-Shogaol,2TMS,isomer #1	CCC/C=C/C(=CCC1=CC=C(O[Si](C)(C)C)C(OC)=C1)O[Si](C)(C)C	2346.6	Semi standard non polar	33892256
[4]-Shogaol,2TMS,isomer #1	CCC/C=C/C(=CCC1=CC=C(O[Si](C)(C)C)C(OC)=C1)O[Si](C)(C)C	2188.4	Standard non polar	33892256
[4]-Shogaol,2TMS,isomer #1	CCC/C=C/C(=CCC1=CC=C(O[Si](C)(C)C)C(OC)=C1)O[Si](C)(C)C	2454.9	Standard polar	33892256
[4]-Shogaol,2TBDMS,isomer #1	CCC/C=C/C(=CCC1=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C1)O[Si](C)(C)C(C)(C)C	2835.4	Semi standard non polar	33892256
[4]-Shogaol,2TBDMS,isomer #1	CCC/C=C/C(=CCC1=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C1)O[Si](C)(C)C(C)(C)C	2654.9	Standard non polar	33892256
[4]-Shogaol,2TBDMS,isomer #1	CCC/C=C/C(=CCC1=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C1)O[Si](C)(C)C(C)(C)C	2658.4	Standard polar	33892256

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - [4]-Shogaol 10V, Positive-QTOF	splash10-0002-1190000000-1ebf2892ad5e034a154d	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - [4]-Shogaol 20V, Positive-QTOF	splash10-0k9b-9740000000-ccb4fb33ba60e13c4847	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - [4]-Shogaol 40V, Positive-QTOF	splash10-0aou-9400000000-58408fcf6a33d3d549c9	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - [4]-Shogaol 10V, Negative-QTOF	splash10-0002-0190000000-39e9b2d7b3bc5551043c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - [4]-Shogaol 20V, Negative-QTOF	splash10-0002-3790000000-a8055cdbc1b5241cda85	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - [4]-Shogaol 40V, Negative-QTOF	splash10-0a4i-6910000000-41570832d367b7b46a94	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - [4]-Shogaol 10V, Positive-QTOF	splash10-000b-1980000000-bdbe1c41341f9218ea1e	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - [4]-Shogaol 20V, Positive-QTOF	splash10-000i-6910000000-42aff9cfa22bb5fe9bed	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - [4]-Shogaol 40V, Positive-QTOF	splash10-0abi-6900000000-0e5973779cc6165e6065	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - [4]-Shogaol 10V, Negative-QTOF	splash10-0002-0090000000-f2ed941b7971f4de1739	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - [4]-Shogaol 20V, Negative-QTOF	splash10-0006-9810000000-ce453190361060917bca	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - [4]-Shogaol 40V, Negative-QTOF	splash10-000f-9300000000-4521ffef446cd90f5d7b	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

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

FDB001888

KNApSAcK ID

C00035446

Chemspider ID

7970664

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9794897

PDB ID

Not Available

ChEBI ID

Not Available

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

Not Available

Showing metabocard for [4]-Shogaol (HMDB0302127)

MOL for HMDB0302127 ([4]-Shogaol)

3D MOL for HMDB0302127 ([4]-Shogaol)

3D SDF for HMDB0302127 ([4]-Shogaol)

3D-SDF for HMDB0302127 ([4]-Shogaol)

PDB for HMDB0302127 ([4]-Shogaol)

3D PDB for HMDB0302127 ([4]-Shogaol)

SMILES for HMDB0302127 ([4]-Shogaol)

INCHI for HMDB0302127 ([4]-Shogaol)

Structure for HMDB0302127 ([4]-Shogaol)

3D Structure for HMDB0302127 ([4]-Shogaol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

MS/MS Spectra