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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:43:29 UTC

Update Date

2022-03-07 02:52:59 UTC

HMDB ID

HMDB0031463

Secondary Accession Numbers

HMDB31463

Metabolite Identification

Common Name

[8]-Shogaol

Description

[8]-Shogaol 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. [8]-Shogaol is found, on average, in the highest concentration within gingers (Zingiber officinale). [8]-Shogaol has also been detected, but not quantified in, alcoholic beverages and herbs and spices. This could make [8]-shogaol a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on [8]-Shogaol.

Structure

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

HMDB0031463
     RDKit          3D
[8]-Shogaol
 44 44  0  0  0  0  0  0  0  0999 V2000
    5.1399    2.2688   -1.2807 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3762    0.9086   -1.9025 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1407   -0.1910   -0.8746 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7030   -0.0661   -0.4142 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3399   -1.0979    0.6062 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9136   -0.8997    0.9913 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1482    0.0360    0.4863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2344    0.1530    0.9244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9112    1.0675    0.4031 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7223   -0.7994    1.9316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1364   -0.6086    2.2966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0703   -0.7554    1.1816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3883   -2.0596    0.7845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2896   -2.2483   -0.2322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8777   -1.1631   -0.8582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7881   -1.3480   -1.8859 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5630    0.1266   -0.4643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1833    1.1713   -1.1276 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8698    2.4904   -0.7342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6466    0.3355    0.5708 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1538    2.1802   -0.1726 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2207    2.7533   -1.6616 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9995    2.9350   -1.5389 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4141    0.8356   -2.2804 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6124    0.7685   -2.6917 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2417   -1.1440   -1.4091 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8637   -0.1415   -0.0458 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0588   -0.2005   -1.3025 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5190    0.9360    0.0270 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9382   -1.0501    1.5224 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4903   -2.1368    0.1967 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4809   -1.5669    1.7321 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5246    0.7194   -0.2484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5724   -1.8508    1.5222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0752   -0.8041    2.8479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3980   -1.3395    3.1237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3432    0.3903    2.7556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9165   -2.8938    1.2877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5214   -3.2728   -0.5240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0028   -2.2969   -2.1567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7831    2.6883   -0.8972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4993    3.2279   -1.2765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0350    2.5664    0.3653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4512    1.3760    0.8619 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  1  0
  5  6  1  0
  6  7  2  3
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 17 20  2  0
 20 12  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  7 33  1  0
 10 34  1  0
 10 35  1  0
 11 36  1  0
 11 37  1  0
 13 38  1  0
 14 39  1  0
 16 40  1  0
 19 41  1  0
 19 42  1  0
 19 43  1  0
 20 44  1  0
M  END

  Mrv0541 02241220472D          

 20 20  0  0  0  0            999 V2000
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -7.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  4  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
 15 18  1  0  0  0  0
 14 19  1  0  0  0  0
 19 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0031463

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C17H24O3/c1-3-4-5-6-7-8-15(18)11-9-14-10-12-16(19)17(13-14)20-2/h7-8,10,12-13,19H,3-6,9,11H2,1-2H3

> <INCHI_KEY>
OQWKEEOHDMUXEO-UHFFFAOYSA-N

> <FORMULA>
C17H24O3

> <MOLECULAR_WEIGHT>
276.3707

> <EXACT_MASS>
276.172544634

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
32.2602735902716

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
4.95

> <JCHEM_LOGP>
4.845154367333334

> <ALOGPS_LOGS>
-4.49

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.945866637773328

> <JCHEM_PKA_STRONGEST_BASIC>
-4.4545534329251115

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
82.68700000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.88e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
shogaol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0031463
     RDKit          3D
[8]-Shogaol
 44 44  0  0  0  0  0  0  0  0999 V2000
    5.1399    2.2688   -1.2807 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3762    0.9086   -1.9025 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1407   -0.1910   -0.8746 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7030   -0.0661   -0.4142 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3399   -1.0979    0.6062 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9136   -0.8997    0.9913 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1482    0.0360    0.4863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2344    0.1530    0.9244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9112    1.0675    0.4031 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7223   -0.7994    1.9316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1364   -0.6086    2.2966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0703   -0.7554    1.1816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3883   -2.0596    0.7845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2896   -2.2483   -0.2322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8777   -1.1631   -0.8582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7881   -1.3480   -1.8859 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5630    0.1266   -0.4643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1833    1.1713   -1.1276 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8698    2.4904   -0.7342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6466    0.3355    0.5708 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1538    2.1802   -0.1726 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2207    2.7533   -1.6616 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9995    2.9350   -1.5389 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4141    0.8356   -2.2804 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6124    0.7685   -2.6917 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2417   -1.1440   -1.4091 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8637   -0.1415   -0.0458 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0588   -0.2005   -1.3025 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5190    0.9360    0.0270 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9382   -1.0501    1.5224 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4903   -2.1368    0.1967 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4809   -1.5669    1.7321 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5246    0.7194   -0.2484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5724   -1.8508    1.5222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0752   -0.8041    2.8479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3980   -1.3395    3.1237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3432    0.3903    2.7556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9165   -2.8938    1.2877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5214   -3.2728   -0.5240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0028   -2.2969   -2.1567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7831    2.6883   -0.8972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4993    3.2279   -1.2765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0350    2.5664    0.3653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4512    1.3760    0.8619 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  1  0
  5  6  1  0
  6  7  2  3
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 17 20  2  0
 20 12  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  7 33  1  0
 10 34  1  0
 10 35  1  0
 11 36  1  0
 11 37  1  0
 13 38  1  0
 14 39  1  0
 16 40  1  0
 19 41  1  0
 19 42  1  0
 19 43  1  0
 20 44  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       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.002  -6.160   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.669  -6.160   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.003  -5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      13.337  -6.160   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      14.671  -5.390   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      16.004  -6.160   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      17.338  -5.390   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      16.004  -7.700   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      17.338  -8.470   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      17.338 -10.010   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      18.672 -10.780   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      18.672 -12.320   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      17.338 -13.090   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      16.004 -12.320   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      16.004 -10.780   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      17.338 -14.630   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      20.005 -13.090   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      20.005 -14.630   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16   12                                                       
CONECT   18   15                                                            
CONECT   19   14   20                                                       
CONECT   20   19                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   40    0
END

COMPND    HMDB0031463
HETATM    1  C1  UNL     1       5.140   2.269  -1.281  1.00  0.00           C  
HETATM    2  C2  UNL     1       5.376   0.909  -1.902  1.00  0.00           C  
HETATM    3  C3  UNL     1       5.141  -0.191  -0.875  1.00  0.00           C  
HETATM    4  C4  UNL     1       3.703  -0.066  -0.414  1.00  0.00           C  
HETATM    5  C5  UNL     1       3.340  -1.098   0.606  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.914  -0.900   0.991  1.00  0.00           C  
HETATM    7  C7  UNL     1       1.148   0.036   0.486  1.00  0.00           C  
HETATM    8  C8  UNL     1      -0.234   0.153   0.924  1.00  0.00           C  
HETATM    9  O1  UNL     1      -0.911   1.068   0.403  1.00  0.00           O  
HETATM   10  C9  UNL     1      -0.722  -0.799   1.932  1.00  0.00           C  
HETATM   11  C10 UNL     1      -2.136  -0.609   2.297  1.00  0.00           C  
HETATM   12  C11 UNL     1      -3.070  -0.755   1.182  1.00  0.00           C  
HETATM   13  C12 UNL     1      -3.388  -2.060   0.785  1.00  0.00           C  
HETATM   14  C13 UNL     1      -4.290  -2.248  -0.232  1.00  0.00           C  
HETATM   15  C14 UNL     1      -4.878  -1.163  -0.858  1.00  0.00           C  
HETATM   16  O2  UNL     1      -5.788  -1.348  -1.886  1.00  0.00           O  
HETATM   17  C15 UNL     1      -4.563   0.127  -0.464  1.00  0.00           C  
HETATM   18  O3  UNL     1      -5.183   1.171  -1.128  1.00  0.00           O  
HETATM   19  C16 UNL     1      -4.870   2.490  -0.734  1.00  0.00           C  
HETATM   20  C17 UNL     1      -3.647   0.335   0.571  1.00  0.00           C  
HETATM   21  H1  UNL     1       5.154   2.180  -0.173  1.00  0.00           H  
HETATM   22  H2  UNL     1       4.221   2.753  -1.662  1.00  0.00           H  
HETATM   23  H3  UNL     1       6.000   2.935  -1.539  1.00  0.00           H  
HETATM   24  H4  UNL     1       6.414   0.836  -2.280  1.00  0.00           H  
HETATM   25  H5  UNL     1       4.612   0.769  -2.692  1.00  0.00           H  
HETATM   26  H6  UNL     1       5.242  -1.144  -1.409  1.00  0.00           H  
HETATM   27  H7  UNL     1       5.864  -0.141  -0.046  1.00  0.00           H  
HETATM   28  H8  UNL     1       3.059  -0.201  -1.303  1.00  0.00           H  
HETATM   29  H9  UNL     1       3.519   0.936   0.027  1.00  0.00           H  
HETATM   30  H10 UNL     1       3.938  -1.050   1.522  1.00  0.00           H  
HETATM   31  H11 UNL     1       3.490  -2.137   0.197  1.00  0.00           H  
HETATM   32  H12 UNL     1       1.481  -1.567   1.732  1.00  0.00           H  
HETATM   33  H13 UNL     1       1.525   0.719  -0.248  1.00  0.00           H  
HETATM   34  H14 UNL     1      -0.572  -1.851   1.522  1.00  0.00           H  
HETATM   35  H15 UNL     1      -0.075  -0.804   2.848  1.00  0.00           H  
HETATM   36  H16 UNL     1      -2.398  -1.339   3.124  1.00  0.00           H  
HETATM   37  H17 UNL     1      -2.343   0.390   2.756  1.00  0.00           H  
HETATM   38  H18 UNL     1      -2.917  -2.894   1.288  1.00  0.00           H  
HETATM   39  H19 UNL     1      -4.521  -3.273  -0.524  1.00  0.00           H  
HETATM   40  H20 UNL     1      -6.003  -2.297  -2.157  1.00  0.00           H  
HETATM   41  H21 UNL     1      -3.783   2.688  -0.897  1.00  0.00           H  
HETATM   42  H22 UNL     1      -5.499   3.228  -1.276  1.00  0.00           H  
HETATM   43  H23 UNL     1      -5.035   2.566   0.365  1.00  0.00           H  
HETATM   44  H24 UNL     1      -3.451   1.376   0.862  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3   24   25
CONECT    3    4   26   27
CONECT    4    5   28   29
CONECT    5    6   30   31
CONECT    6    7    7   32
CONECT    7    8   33
CONECT    8    9    9   10
CONECT   10   11   34   35
CONECT   11   12   36   37
CONECT   12   13   13   20
CONECT   13   14   38
CONECT   14   15   15   39
CONECT   15   16   17
CONECT   16   40
CONECT   17   18   20   20
CONECT   18   19
CONECT   19   41   42   43
CONECT   20   44
END

HMDB0031463
     RDKit          3D
[8]-Shogaol
 44 44  0  0  0  0  0  0  0  0999 V2000
    5.1399    2.2688   -1.2807 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3762    0.9086   -1.9025 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1407   -0.1910   -0.8746 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7030   -0.0661   -0.4142 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3399   -1.0979    0.6062 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9136   -0.8997    0.9913 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1482    0.0360    0.4863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2344    0.1530    0.9244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9112    1.0675    0.4031 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7223   -0.7994    1.9316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1364   -0.6086    2.2966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0703   -0.7554    1.1816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3883   -2.0596    0.7845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2896   -2.2483   -0.2322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8777   -1.1631   -0.8582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7881   -1.3480   -1.8859 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5630    0.1266   -0.4643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1833    1.1713   -1.1276 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8698    2.4904   -0.7342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6466    0.3355    0.5708 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1538    2.1802   -0.1726 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2207    2.7533   -1.6616 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9995    2.9350   -1.5389 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4141    0.8356   -2.2804 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6124    0.7685   -2.6917 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2417   -1.1440   -1.4091 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8637   -0.1415   -0.0458 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0588   -0.2005   -1.3025 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5190    0.9360    0.0270 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9382   -1.0501    1.5224 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4903   -2.1368    0.1967 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4809   -1.5669    1.7321 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5246    0.7194   -0.2484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5724   -1.8508    1.5222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0752   -0.8041    2.8479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3980   -1.3395    3.1237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3432    0.3903    2.7556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9165   -2.8938    1.2877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5214   -3.2728   -0.5240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0028   -2.2969   -2.1567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7831    2.6883   -0.8972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4993    3.2279   -1.2765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0350    2.5664    0.3653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4512    1.3760    0.8619 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  1  0
  5  6  1  0
  6  7  2  3
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 17 20  2  0
 20 12  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  7 33  1  0
 10 34  1  0
 10 35  1  0
 11 36  1  0
 11 37  1  0
 13 38  1  0
 14 39  1  0
 16 40  1  0
 19 41  1  0
 19 42  1  0
 19 43  1  0
 20 44  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-(4-Hydroxy-3-methoxyphenyl)-4-dodecen-3-one, 9ci	HMDB

Chemical Formula

C₁₇H₂₄O₃

Average Molecular Weight

276.3707

Monoisotopic Molecular Weight

276.172544634

IUPAC Name

1-(4-hydroxy-3-methoxyphenyl)dec-4-en-3-one

Traditional Name

shogaol

CAS Registry Number

36700-45-5

SMILES

CCCCCC=CC(=O)CCC1=CC(OC)=C(O)C=C1

InChI Identifier

InChI=1S/C17H24O3/c1-3-4-5-6-7-8-15(18)11-9-14-10-12-16(19)17(13-14)20-2/h7-8,10,12-13,19H,3-6,9,11H2,1-2H3

InChI Key

OQWKEEOHDMUXEO-UHFFFAOYSA-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

a small molecule (CPD-13646 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0031463)
Cell membrane (HMDB: HMDB0031463)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0031463)

Source

Exogenous

Exogenous (HMDB: HMDB0031463)

Food

Food (HMDB: HMDB0031463)

Herb and spice

Spice

Ginger (FooDB: FOOD00206)

Endogenous

Plant

Plant (HMDB: HMDB0031463)

Process

Not Available

Role

Biological role

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	0.34 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0089 g/L	ALOGPS
logP	4.95	ALOGPS
logP	4.85	ChemAxon
logS	-4.5	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	9	ChemAxon
Refractivity	82.69 m³·mol⁻¹	ChemAxon
Polarizability	32.26 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
DarkChem	[M+H]+	170.563	31661259
DarkChem	[M-H]-	173.307	31661259
DeepCCS	[M+H]+	173.293	30932474
DeepCCS	[M-H]-	170.935	30932474
DeepCCS	[M-2H]-	203.821	30932474
DeepCCS	[M+Na]+	179.387	30932474
AllCCS	[M+H]+	170.7	32859911
AllCCS	[M+H-H2O]+	167.3	32859911
AllCCS	[M+NH4]+	173.9	32859911
AllCCS	[M+Na]+	174.8	32859911
AllCCS	[M-H]-	172.9	32859911
AllCCS	[M+Na-2H]-	173.7	32859911
AllCCS	[M+HCOO]-	174.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
[8]-Shogaol	CCCCCC=CC(=O)CCC1=CC(OC)=C(O)C=C1	3883.3	Standard polar	33892256
[8]-Shogaol	CCCCCC=CC(=O)CCC1=CC(OC)=C(O)C=C1	2246.3	Standard non polar	33892256
[8]-Shogaol	CCCCCC=CC(=O)CCC1=CC(OC)=C(O)C=C1	2273.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
[8]-Shogaol,1TMS,isomer #1	CCCCCC=CC(=O)CCC1=CC=C(O[Si](C)(C)C)C(OC)=C1	2358.3	Semi standard non polar	33892256
[8]-Shogaol,1TMS,isomer #2	CCCCCC=CC(=CCC1=CC=C(O)C(OC)=C1)O[Si](C)(C)C	2523.2	Semi standard non polar	33892256
[8]-Shogaol,2TMS,isomer #1	CCCCCC=CC(=CCC1=CC=C(O[Si](C)(C)C)C(OC)=C1)O[Si](C)(C)C	2537.9	Semi standard non polar	33892256
[8]-Shogaol,2TMS,isomer #1	CCCCCC=CC(=CCC1=CC=C(O[Si](C)(C)C)C(OC)=C1)O[Si](C)(C)C	2375.2	Standard non polar	33892256
[8]-Shogaol,1TBDMS,isomer #1	CCCCCC=CC(=O)CCC1=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C1	2612.4	Semi standard non polar	33892256
[8]-Shogaol,1TBDMS,isomer #2	CCCCCC=CC(=CCC1=CC=C(O)C(OC)=C1)O[Si](C)(C)C(C)(C)C	2772.7	Semi standard non polar	33892256
[8]-Shogaol,2TBDMS,isomer #1	CCCCCC=CC(=CCC1=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C1)O[Si](C)(C)C(C)(C)C	3030.0	Semi standard non polar	33892256
[8]-Shogaol,2TBDMS,isomer #1	CCCCCC=CC(=CCC1=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C1)O[Si](C)(C)C(C)(C)C	2820.7	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - [8]-Shogaol GC-MS (Non-derivatized) - 70eV, Positive	splash10-004i-9620000000-f02bcd9c6283a8cf88fc	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - [8]-Shogaol GC-MS (1 TMS) - 70eV, Positive	splash10-05iu-9154000000-46bfcab1accb3045874c	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - [8]-Shogaol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - [8]-Shogaol 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 - [8]-Shogaol 10V, Positive-QTOF	splash10-004i-1190000000-06bc9c8afe1085ba2632	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - [8]-Shogaol 20V, Positive-QTOF	splash10-005i-8950000000-03ec6db458ca2af67e59	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - [8]-Shogaol 40V, Positive-QTOF	splash10-0k96-9510000000-caea94c9bbdf4f66b2e6	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - [8]-Shogaol 10V, Negative-QTOF	splash10-004i-0190000000-6ef295bdbca7cf3546e1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - [8]-Shogaol 20V, Negative-QTOF	splash10-004i-2890000000-eebd2ec4aab29e15a6d3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - [8]-Shogaol 40V, Negative-QTOF	splash10-000i-4910000000-cd83ea72d889effd1847	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - [8]-Shogaol 10V, Negative-QTOF	splash10-004i-0190000000-04e9fac4b2d89f8de33c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - [8]-Shogaol 20V, Negative-QTOF	splash10-0079-0910000000-d969ff7bbc61fa67e090	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - [8]-Shogaol 40V, Negative-QTOF	splash10-01c9-7900000000-f0e945b67230d4f40916	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - [8]-Shogaol 10V, Positive-QTOF	splash10-002r-0940000000-7539d94259bc6d6ea4eb	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - [8]-Shogaol 20V, Positive-QTOF	splash10-052r-5910000000-95c63f7cd49c9953b9a8	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - [8]-Shogaol 40V, Positive-QTOF	splash10-0fy9-4900000000-79cdde4da585ea08da9b	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5281794

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1826871

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 [8]-Shogaol (HMDB0031463)

MOL for HMDB0031463 ([8]-Shogaol)

3D MOL for HMDB0031463 ([8]-Shogaol)

3D SDF for HMDB0031463 ([8]-Shogaol)

3D-SDF for HMDB0031463 ([8]-Shogaol)

PDB for HMDB0031463 ([8]-Shogaol)

3D PDB for HMDB0031463 ([8]-Shogaol)

SMILES for HMDB0031463 ([8]-Shogaol)

INCHI for HMDB0031463 ([8]-Shogaol)

Structure for HMDB0031463 ([8]-Shogaol)

3D Structure for HMDB0031463 ([8]-Shogaol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra