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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

HMDB0031464

Secondary Accession Numbers

HMDB31464

Metabolite Identification

Common Name

cis-[8]-Shogaol

Description

cis-[8]-Shogaol, also known as (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. cis-[8]-Shogaol has been detected, but not quantified in, gingers (Zingiber officinale). This could make cis-[8]-shogaol a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on cis-[8]-Shogaol.

Structure

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

HMDB0031464
     RDKit          3D
cis-[8]-Shogaol
 50 50  0  0  0  0  0  0  0  0999 V2000
   -8.2926    0.3724    0.0052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0253   -0.1177   -0.6677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0573   -0.7204    0.3447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8428   -1.1683   -0.4461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7987   -1.7838    0.4177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2677   -0.8745    1.4797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6286    0.3772    0.8934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4929    0.0284    0.0019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2665    0.4591    0.2474 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8629    0.1308   -0.6112 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7181   -0.5806   -1.6285 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2069    0.6416   -0.2843 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1811    0.1690   -1.3086 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5266    0.7123   -0.9332 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8975    1.9376   -1.4301 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1339    2.4347   -1.0839 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9653    1.6841   -0.2455 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2092    2.1961    0.0962 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5820    0.4486    0.2509 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4460   -0.2716    1.0887 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9896   -1.5259    1.5586 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3462   -0.0283   -0.1063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0081    0.7502    1.0017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8009    1.1155   -0.6172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9312   -0.5330    0.1805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2426   -0.8902   -1.4321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5129    0.7206   -1.2212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5860   -1.5920    0.7814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8210   -0.0300    1.1562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2007   -1.9399   -1.1579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4200   -0.3526   -1.0499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9547   -2.0929   -0.2287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2236   -2.6767    0.9186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4163   -1.4261    1.9775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9737   -0.6366    2.2778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3593    0.9969    0.3401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2235    0.9587    1.7434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6337   -0.5972   -0.8880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1507    1.0750    1.1311 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4817    0.3019    0.7560 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2318    1.7569   -0.2195 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2454   -0.9132   -1.4129 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9129    0.5885   -2.2902 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2376    2.4948   -2.0740 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4954    3.4029   -1.4420 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8026    1.6547    0.6978 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8618   -2.0693    1.9831 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6066   -2.1730    0.7368 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1789   -1.4217    2.3213 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0113   -0.9930    0.2633 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  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 19 22  2  0
 22 14  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  6 34  1  0
  6 35  1  0
  7 36  1  0
  7 37  1  0
  8 38  1  0
  9 39  1  0
 12 40  1  0
 12 41  1  0
 13 42  1  0
 13 43  1  0
 15 44  1  0
 16 45  1  0
 18 46  1  0
 21 47  1  0
 21 48  1  0
 21 49  1  0
 22 50  1  0
M  END

  Mrv1652307301919592D          

 22 22  0  0  0  0            999 V2000
   -8.5737    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8592    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    0.8250    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
   -2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    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
    0.7145   -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
    0.0000    0.8250    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
    1.4289    0.0000    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
   -2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  2  0  0  0  0
 13 11  1  0  0  0  0
 14 12  2  0  0  0  0
 16 11  1  0  0  0  0
 16 12  1  0  0  0  0
 16 15  2  0  0  0  0
 17 10  1  0  0  0  0
 17 13  1  0  0  0  0
 18 14  1  0  0  0  0
 19 15  1  0  0  0  0
 19 18  2  0  0  0  0
 20 17  2  0  0  0  0
 21 18  1  0  0  0  0
 22  2  1  0  0  0  0
 22 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0031464

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C19H28O3/c1-3-4-5-6-7-8-9-10-17(20)13-11-16-12-14-18(21)19(15-16)22-2/h9-10,12,14-15,21H,3-8,11,13H2,1-2H3/b10-9+

> <INCHI_KEY>
LGZSMXJRMTYABD-MDZDMXLPSA-N

> <FORMULA>
C19H28O3

> <MOLECULAR_WEIGHT>
304.4238

> <EXACT_MASS>
304.203844762

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
36.35578240931276

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
5.734291697333335

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.945866637773328

> <JCHEM_PKA_STRONGEST_BASIC>
-4.454554198390189

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
91.88899999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0031464
     RDKit          3D
cis-[8]-Shogaol
 50 50  0  0  0  0  0  0  0  0999 V2000
   -8.2926    0.3724    0.0052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0253   -0.1177   -0.6677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0573   -0.7204    0.3447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8428   -1.1683   -0.4461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7987   -1.7838    0.4177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2677   -0.8745    1.4797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6286    0.3772    0.8934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4929    0.0284    0.0019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2665    0.4591    0.2474 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8629    0.1308   -0.6112 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7181   -0.5806   -1.6285 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2069    0.6416   -0.2843 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1811    0.1690   -1.3086 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5266    0.7123   -0.9332 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8975    1.9376   -1.4301 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1339    2.4347   -1.0839 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9653    1.6841   -0.2455 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2092    2.1961    0.0962 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5820    0.4486    0.2509 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4460   -0.2716    1.0887 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9896   -1.5259    1.5586 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3462   -0.0283   -0.1063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0081    0.7502    1.0017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8009    1.1155   -0.6172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9312   -0.5330    0.1805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2426   -0.8902   -1.4321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5129    0.7206   -1.2212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5860   -1.5920    0.7814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8210   -0.0300    1.1562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2007   -1.9399   -1.1579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4200   -0.3526   -1.0499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9547   -2.0929   -0.2287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2236   -2.6767    0.9186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4163   -1.4261    1.9775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9737   -0.6366    2.2778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3593    0.9969    0.3401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2235    0.9587    1.7434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6337   -0.5972   -0.8880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1507    1.0750    1.1311 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4817    0.3019    0.7560 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2318    1.7569   -0.2195 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2454   -0.9132   -1.4129 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9129    0.5885   -2.2902 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2376    2.4948   -2.0740 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4954    3.4029   -1.4420 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8026    1.6547    0.6978 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8618   -2.0693    1.9831 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6066   -2.1730    0.7368 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1789   -1.4217    2.3213 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0113   -0.9930    0.2633 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  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 19 22  2  0
 22 14  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  6 34  1  0
  6 35  1  0
  7 36  1  0
  7 37  1  0
  8 38  1  0
  9 39  1  0
 12 40  1  0
 12 41  1  0
 13 42  1  0
 13 43  1  0
 15 44  1  0
 16 45  1  0
 18 46  1  0
 21 47  1  0
 21 48  1  0
 21 49  1  0
 22 50  1  0
M  END

HEADER    PROTEIN                                 30-JUL-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-JUL-19         0                                  
HETATM    1  C   UNK     0     -16.004   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -14.671   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -13.337   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -12.003   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -10.669   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -9.336   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -8.002   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -6.668   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334  -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  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -4.001   3.850   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2   22                                                            
CONECT    3    1    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   17                                                       
CONECT   11   13   16                                                       
CONECT   12   14   16                                                       
CONECT   13   11   17                                                       
CONECT   14   12   18                                                       
CONECT   15   16   19                                                       
CONECT   16   11   12   15                                                  
CONECT   17   10   13   20                                                  
CONECT   18   14   19   21                                                  
CONECT   19   15   18   22                                                  
CONECT   20   17                                                            
CONECT   21   18                                                            
CONECT   22    2   19                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   44    0
END

COMPND    HMDB0031464
HETATM    1  C1  UNL     1      -8.293   0.372   0.005  1.00  0.00           C  
HETATM    2  C2  UNL     1      -7.025  -0.118  -0.668  1.00  0.00           C  
HETATM    3  C3  UNL     1      -6.057  -0.720   0.345  1.00  0.00           C  
HETATM    4  C4  UNL     1      -4.843  -1.168  -0.446  1.00  0.00           C  
HETATM    5  C5  UNL     1      -3.799  -1.784   0.418  1.00  0.00           C  
HETATM    6  C6  UNL     1      -3.268  -0.875   1.480  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.629   0.377   0.893  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.493   0.028   0.002  1.00  0.00           C  
HETATM    9  C9  UNL     1      -0.266   0.459   0.247  1.00  0.00           C  
HETATM   10  C10 UNL     1       0.863   0.131  -0.611  1.00  0.00           C  
HETATM   11  O1  UNL     1       0.718  -0.581  -1.629  1.00  0.00           O  
HETATM   12  C11 UNL     1       2.207   0.642  -0.284  1.00  0.00           C  
HETATM   13  C12 UNL     1       3.181   0.169  -1.309  1.00  0.00           C  
HETATM   14  C13 UNL     1       4.527   0.712  -0.933  1.00  0.00           C  
HETATM   15  C14 UNL     1       4.897   1.938  -1.430  1.00  0.00           C  
HETATM   16  C15 UNL     1       6.134   2.435  -1.084  1.00  0.00           C  
HETATM   17  C16 UNL     1       6.965   1.684  -0.245  1.00  0.00           C  
HETATM   18  O2  UNL     1       8.209   2.196   0.096  1.00  0.00           O  
HETATM   19  C17 UNL     1       6.582   0.449   0.251  1.00  0.00           C  
HETATM   20  O3  UNL     1       7.446  -0.272   1.089  1.00  0.00           O  
HETATM   21  C18 UNL     1       6.990  -1.526   1.559  1.00  0.00           C  
HETATM   22  C19 UNL     1       5.346  -0.028  -0.106  1.00  0.00           C  
HETATM   23  H1  UNL     1      -8.008   0.750   1.002  1.00  0.00           H  
HETATM   24  H2  UNL     1      -8.801   1.115  -0.617  1.00  0.00           H  
HETATM   25  H3  UNL     1      -8.931  -0.533   0.181  1.00  0.00           H  
HETATM   26  H4  UNL     1      -7.243  -0.890  -1.432  1.00  0.00           H  
HETATM   27  H5  UNL     1      -6.513   0.721  -1.221  1.00  0.00           H  
HETATM   28  H6  UNL     1      -6.586  -1.592   0.781  1.00  0.00           H  
HETATM   29  H7  UNL     1      -5.821  -0.030   1.156  1.00  0.00           H  
HETATM   30  H8  UNL     1      -5.201  -1.940  -1.158  1.00  0.00           H  
HETATM   31  H9  UNL     1      -4.420  -0.353  -1.050  1.00  0.00           H  
HETATM   32  H10 UNL     1      -2.955  -2.093  -0.229  1.00  0.00           H  
HETATM   33  H11 UNL     1      -4.224  -2.677   0.919  1.00  0.00           H  
HETATM   34  H12 UNL     1      -2.416  -1.426   1.977  1.00  0.00           H  
HETATM   35  H13 UNL     1      -3.974  -0.637   2.278  1.00  0.00           H  
HETATM   36  H14 UNL     1      -3.359   0.997   0.340  1.00  0.00           H  
HETATM   37  H15 UNL     1      -2.223   0.959   1.743  1.00  0.00           H  
HETATM   38  H16 UNL     1      -1.634  -0.597  -0.888  1.00  0.00           H  
HETATM   39  H17 UNL     1      -0.151   1.075   1.131  1.00  0.00           H  
HETATM   40  H18 UNL     1       2.482   0.302   0.756  1.00  0.00           H  
HETATM   41  H19 UNL     1       2.232   1.757  -0.220  1.00  0.00           H  
HETATM   42  H20 UNL     1       3.245  -0.913  -1.413  1.00  0.00           H  
HETATM   43  H21 UNL     1       2.913   0.588  -2.290  1.00  0.00           H  
HETATM   44  H22 UNL     1       4.238   2.495  -2.074  1.00  0.00           H  
HETATM   45  H23 UNL     1       6.495   3.403  -1.442  1.00  0.00           H  
HETATM   46  H24 UNL     1       8.803   1.655   0.698  1.00  0.00           H  
HETATM   47  H25 UNL     1       7.862  -2.069   1.983  1.00  0.00           H  
HETATM   48  H26 UNL     1       6.607  -2.173   0.737  1.00  0.00           H  
HETATM   49  H27 UNL     1       6.179  -1.422   2.321  1.00  0.00           H  
HETATM   50  H28 UNL     1       5.011  -0.993   0.263  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3   26   27
CONECT    3    4   28   29
CONECT    4    5   30   31
CONECT    5    6   32   33
CONECT    6    7   34   35
CONECT    7    8   36   37
CONECT    8    9    9   38
CONECT    9   10   39
CONECT   10   11   11   12
CONECT   12   13   40   41
CONECT   13   14   42   43
CONECT   14   15   15   22
CONECT   15   16   44
CONECT   16   17   17   45
CONECT   17   18   19
CONECT   18   46
CONECT   19   20   22   22
CONECT   20   21
CONECT   21   47   48   49
CONECT   22   50
END

HMDB0031464
     RDKit          3D
cis-[8]-Shogaol
 50 50  0  0  0  0  0  0  0  0999 V2000
   -8.2926    0.3724    0.0052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0253   -0.1177   -0.6677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0573   -0.7204    0.3447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8428   -1.1683   -0.4461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7987   -1.7838    0.4177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2677   -0.8745    1.4797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6286    0.3772    0.8934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4929    0.0284    0.0019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2665    0.4591    0.2474 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8629    0.1308   -0.6112 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7181   -0.5806   -1.6285 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2069    0.6416   -0.2843 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1811    0.1690   -1.3086 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5266    0.7123   -0.9332 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8975    1.9376   -1.4301 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1339    2.4347   -1.0839 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9653    1.6841   -0.2455 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2092    2.1961    0.0962 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5820    0.4486    0.2509 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4460   -0.2716    1.0887 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9896   -1.5259    1.5586 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3462   -0.0283   -0.1063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0081    0.7502    1.0017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8009    1.1155   -0.6172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9312   -0.5330    0.1805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2426   -0.8902   -1.4321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5129    0.7206   -1.2212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5860   -1.5920    0.7814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8210   -0.0300    1.1562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2007   -1.9399   -1.1579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4200   -0.3526   -1.0499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9547   -2.0929   -0.2287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2236   -2.6767    0.9186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4163   -1.4261    1.9775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9737   -0.6366    2.2778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3593    0.9969    0.3401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2235    0.9587    1.7434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6337   -0.5972   -0.8880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1507    1.0750    1.1311 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4817    0.3019    0.7560 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2318    1.7569   -0.2195 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2454   -0.9132   -1.4129 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9129    0.5885   -2.2902 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2376    2.4948   -2.0740 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4954    3.4029   -1.4420 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8026    1.6547    0.6978 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8618   -2.0693    1.9831 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6066   -2.1730    0.7368 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1789   -1.4217    2.3213 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0113   -0.9930    0.2633 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  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 19 22  2  0
 22 14  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  6 34  1  0
  6 35  1  0
  7 36  1  0
  7 37  1  0
  8 38  1  0
  9 39  1  0
 12 40  1  0
 12 41  1  0
 13 42  1  0
 13 43  1  0
 15 44  1  0
 16 45  1  0
 18 46  1  0
 21 47  1  0
 21 48  1  0
 21 49  1  0
 22 50  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(8)-Shogaol	MeSH
8-Shogaol	ChEMBL, HMDB
cis-8-SHOGAOL	HMDB

Chemical Formula

C₁₉H₂₈O₃

Average Molecular Weight

304.4238

Monoisotopic Molecular Weight

304.203844762

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C19H28O3/c1-3-4-5-6-7-8-9-10-17(20)13-11-16-12-14-18(21)19(15-16)22-2/h9-10,12,14-15,21H,3-8,11,13H2,1-2H3/b10-9+

InChI Key

LGZSMXJRMTYABD-MDZDMXLPSA-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

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0031464)
Cell membrane (HMDB: HMDB0031464)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0031464)

Source

Endogenous

Endogenous (HMDB: HMDB0031464)

Plant

Plant (HMDB: HMDB0031464)

Exogenous

Food

Food (HMDB: HMDB0031464)

Herb and spice

Spice

Ginger (FooDB: FOOD00206)

Exogenous (HMDB: HMDB0031464)

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
Water Solubility	0.0018 g/L	ALOGPS
logP	5.73	ChemAxon
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	11	ChemAxon
Refractivity	91.89 m³·mol⁻¹	ChemAxon
Polarizability	36.36 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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]+	186.18	30932474
DeepCCS	[M-H]-	183.822	30932474
DeepCCS	[M-2H]-	216.708	30932474
DeepCCS	[M+Na]+	192.274	30932474
AllCCS	[M+H]+	180.1	32859911
AllCCS	[M+H-H2O]+	177.0	32859911
AllCCS	[M+NH4]+	183.1	32859911
AllCCS	[M+Na]+	183.9	32859911
AllCCS	[M-H]-	181.6	32859911
AllCCS	[M+Na-2H]-	182.7	32859911
AllCCS	[M+HCOO]-	184.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
cis-[8]-Shogaol	CCCCCCC\C=C\C(=O)CCC1=CC(OC)=C(O)C=C1	4129.4	Standard polar	33892256
cis-[8]-Shogaol	CCCCCCC\C=C\C(=O)CCC1=CC(OC)=C(O)C=C1	2435.1	Standard non polar	33892256
cis-[8]-Shogaol	CCCCCCC\C=C\C(=O)CCC1=CC(OC)=C(O)C=C1	2485.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
cis-[8]-Shogaol,1TMS,isomer #1	CCCCCCC/C=C/C(=O)CCC1=CC=C(O[Si](C)(C)C)C(OC)=C1	2551.6	Semi standard non polar	33892256
cis-[8]-Shogaol,1TMS,isomer #2	CCCCCCC/C=C/C(=CCC1=CC=C(O)C(OC)=C1)O[Si](C)(C)C	2718.8	Semi standard non polar	33892256
cis-[8]-Shogaol,2TMS,isomer #1	CCCCCCC/C=C/C(=CCC1=CC=C(O[Si](C)(C)C)C(OC)=C1)O[Si](C)(C)C	2738.8	Semi standard non polar	33892256
cis-[8]-Shogaol,2TMS,isomer #1	CCCCCCC/C=C/C(=CCC1=CC=C(O[Si](C)(C)C)C(OC)=C1)O[Si](C)(C)C	2553.9	Standard non polar	33892256
cis-[8]-Shogaol,1TBDMS,isomer #1	CCCCCCC/C=C/C(=O)CCC1=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C1	2804.9	Semi standard non polar	33892256
cis-[8]-Shogaol,1TBDMS,isomer #2	CCCCCCC/C=C/C(=CCC1=CC=C(O)C(OC)=C1)O[Si](C)(C)C(C)(C)C	2964.1	Semi standard non polar	33892256
cis-[8]-Shogaol,2TBDMS,isomer #1	CCCCCCC/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	3225.1	Semi standard non polar	33892256
cis-[8]-Shogaol,2TBDMS,isomer #1	CCCCCCC/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	2974.1	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - cis-[8]-Shogaol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ug0-9530000000-e20ef27b5280ff5ee251	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - cis-[8]-Shogaol GC-MS (1 TMS) - 70eV, Positive	splash10-0ir0-9126000000-11c9f220f1f8a0af38fe	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - cis-[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
Experimental LC-MS/MS	LC-MS/MS Spectrum - cis-[8]-Shogaol , positive-QTOF	splash10-000i-0900000000-8af586f12af17cb2ff25	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - cis-[8]-Shogaol , positive-QTOF	splash10-000i-0900000000-7e3aa5a3100bfee96dc7	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-[8]-Shogaol 10V, Negative-QTOF	splash10-0udi-0209000000-35ae835d6a02f9ab17b1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-[8]-Shogaol 20V, Negative-QTOF	splash10-0ufr-0924000000-c4abe8cdbf8068a61d7c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-[8]-Shogaol 40V, Negative-QTOF	splash10-02t9-1910000000-b22f5a143d260d81210e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-[8]-Shogaol 10V, Negative-QTOF	splash10-0udi-0109000000-d448c016b7a08fc130ee	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-[8]-Shogaol 20V, Negative-QTOF	splash10-0gb9-0902000000-3594da3f85e78a13d8be	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-[8]-Shogaol 40V, Negative-QTOF	splash10-05tr-3900000000-c8d1b81cba78e2a10a9e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-[8]-Shogaol 10V, Positive-QTOF	splash10-0a4i-0329000000-7442e7476f444e4b8c66	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-[8]-Shogaol 20V, Positive-QTOF	splash10-0pbi-3911000000-e151599acc5597ea42f7	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-[8]-Shogaol 40V, Positive-QTOF	splash10-0k9f-9610000000-919607f0cfb79f30b491	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-[8]-Shogaol 10V, Positive-QTOF	splash10-0a4r-0908000000-b442539b4e45c6e98ba3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-[8]-Shogaol 20V, Positive-QTOF	splash10-052r-3911000000-fa105dc063b655e9adad	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-[8]-Shogaol 40V, Positive-QTOF	splash10-0f79-2900000000-04a7e19cb68b1421de23	2021-09-22	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

FDB007772

KNApSAcK ID

C00035035

Chemspider ID

4946630

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6442560

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

(). Duke, James A. (1992) Handbook of phytochemical constituents of GRAS herbs and other economic plants. Boca Raton, FL. CRC Press.. .

Showing metabocard for cis-[8]-Shogaol (HMDB0031464)

MOL for HMDB0031464 (cis-[8]-Shogaol)

3D MOL for HMDB0031464 (cis-[8]-Shogaol)

3D SDF for HMDB0031464 (cis-[8]-Shogaol)

3D-SDF for HMDB0031464 (cis-[8]-Shogaol)

PDB for HMDB0031464 (cis-[8]-Shogaol)

3D PDB for HMDB0031464 (cis-[8]-Shogaol)

SMILES for HMDB0031464 (cis-[8]-Shogaol)

INCHI for HMDB0031464 (cis-[8]-Shogaol)

Structure for HMDB0031464 (cis-[8]-Shogaol)

3D Structure for HMDB0031464 (cis-[8]-Shogaol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra