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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:53:52 UTC

Update Date

2022-03-07 02:53:36 UTC

HMDB ID

HMDB0033125

Secondary Accession Numbers

HMDB33125

Metabolite Identification

Common Name

[8]-Dehydroshogaol

Description

[8]-Dehydroshogaol belongs to the class of organic compounds known as hydroxycinnamic acids and derivatives. Hydroxycinnamic acids and derivatives are compounds containing an cinnamic acid (or a derivative thereof) where the benzene ring is hydroxylated. [8]-Dehydroshogaol has been detected, but not quantified in, herbs and spices. This could make [8]-dehydroshogaol a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on [8]-Dehydroshogaol.

Structure

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

HMDB0033125
     RDKit          3D
[8]-Dehydroshogaol
 48 48  0  0  0  0  0  0  0  0999 V2000
    6.0218    0.2989   -2.4332 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3997   -0.4905   -1.2017 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5015   -0.0111   -0.0571 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0701   -0.2563   -0.4258 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1207    0.1940    0.6545 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3449   -0.5166    1.9656 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3261    0.0181    2.9812 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9662   -0.2871    2.4058 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1164    0.6731    2.1434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2357    0.5056    1.5826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8418    1.5858    1.4320 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7340   -0.7671    1.2569 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9106   -1.0558    0.8305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9990   -0.1902    0.6019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3929    0.9326    1.2662 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4298    1.7191    0.7973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1201    1.4139   -0.3548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1530    2.1977   -0.8218 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7497    0.2914   -1.0398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4362   -0.0291   -2.1986 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0529   -1.1901   -2.9068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7367   -0.4842   -0.5924 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4171    1.2041   -2.1923 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4471   -0.3216   -3.1577 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9969    0.6284   -2.8943 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4452   -0.3291   -0.8928 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2160   -1.5854   -1.3826 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6564    1.0984   -0.0179 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7685   -0.5104    0.8759 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8084    0.2527   -1.3722 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9440   -1.3545   -0.6392 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2745    1.3007    0.7628 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0862    0.0658    0.2842 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3645   -0.4248    2.3362 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1130   -1.5911    1.7938 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4564    1.1053    3.1142 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4658   -0.5686    3.9061 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6857   -1.3065    2.2080 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4851    1.6890    2.3791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9950   -1.6204    1.3891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1094   -2.1647    0.6133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9368    1.1584    2.2143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7313    2.6199    1.3419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6480    1.9569   -1.6702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7837   -1.3291   -3.7259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0310   -2.0850   -2.2530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0058   -1.0752   -3.2969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4651   -1.3655   -1.1531 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
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 10 11  2  0
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  8 38  1  0
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 18 44  1  0
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 21 47  1  0
 22 48  1  0
M  END

  Mrv0541 05061306562D          

 22 22  0  0  0  0            999 V2000
   -7.8592   -0.4125    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
   -7.1447    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    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
   -1.4289    0.0000    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
   -0.7145   -0.4125    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  2  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
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 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>
HMDB0033125

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C19H26O3/c1-3-4-5-6-7-8-9-10-17(20)13-11-16-12-14-18(21)19(15-16)22-2/h9-15,21H,3-8H2,1-2H3/b10-9+,13-11-

> <INCHI_KEY>
WTJRJJFXDZXSLU-LTCRFSFDSA-N

> <FORMULA>
C19H26O3

> <MOLECULAR_WEIGHT>
302.4079

> <EXACT_MASS>
302.188194698

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
36.051031723928915

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1Z,4E)-1-(4-hydroxy-3-methoxyphenyl)dodeca-1,4-dien-3-one

> <ALOGPS_LOGP>
5.73

> <JCHEM_LOGP>
5.814815187000001

> <ALOGPS_LOGS>
-5.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.505000698021625

> <JCHEM_PKA_STRONGEST_BASIC>
-4.320935967860795

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
92.98229999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.50e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1Z,4E)-1-(4-hydroxy-3-methoxyphenyl)dodeca-1,4-dien-3-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0033125
     RDKit          3D
[8]-Dehydroshogaol
 48 48  0  0  0  0  0  0  0  0999 V2000
    6.0218    0.2989   -2.4332 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3997   -0.4905   -1.2017 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5015   -0.0111   -0.0571 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0701   -0.2563   -0.4258 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1207    0.1940    0.6545 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3449   -0.5166    1.9656 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3261    0.0181    2.9812 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9662   -0.2871    2.4058 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1164    0.6731    2.1434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2357    0.5056    1.5826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8418    1.5858    1.4320 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7340   -0.7671    1.2569 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9106   -1.0558    0.8305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9990   -0.1902    0.6019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3929    0.9326    1.2662 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4298    1.7191    0.7973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1201    1.4139   -0.3548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1530    2.1977   -0.8218 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7497    0.2914   -1.0398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4362   -0.0291   -2.1986 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0529   -1.1901   -2.9068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7367   -0.4842   -0.5924 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4171    1.2041   -2.1923 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4471   -0.3216   -3.1577 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9969    0.6284   -2.8943 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4452   -0.3291   -0.8928 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2160   -1.5854   -1.3826 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6564    1.0984   -0.0179 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7685   -0.5104    0.8759 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8084    0.2527   -1.3722 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9440   -1.3545   -0.6392 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2745    1.3007    0.7628 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0862    0.0658    0.2842 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3645   -0.4248    2.3362 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1130   -1.5911    1.7938 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4564    1.1053    3.1142 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4658   -0.5686    3.9061 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6857   -1.3065    2.2080 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4851    1.6890    2.3791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9950   -1.6204    1.3891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1094   -2.1647    0.6133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9368    1.1584    2.2143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7313    2.6199    1.3419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6480    1.9569   -1.6702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7837   -1.3291   -3.7259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0310   -2.0850   -2.2530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0058   -1.0752   -3.2969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4651   -1.3655   -1.1531 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
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  6  7  1  0
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  9 10  1  0
 10 11  2  0
 10 12  1  0
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 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
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  4 30  1  0
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  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
 13 41  1  0
 15 42  1  0
 16 43  1  0
 18 44  1  0
 21 45  1  0
 21 46  1  0
 21 47  1  0
 22 48  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0     -14.671  -0.770   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     -13.337   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -12.003  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -10.669   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -8.002   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.335   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.001  -0.770   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      -2.667   0.000   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      -1.334  -0.770   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    HMDB0033125
HETATM    1  C1  UNL     1       6.022   0.299  -2.433  1.00  0.00           C  
HETATM    2  C2  UNL     1       6.400  -0.490  -1.202  1.00  0.00           C  
HETATM    3  C3  UNL     1       5.502  -0.011  -0.057  1.00  0.00           C  
HETATM    4  C4  UNL     1       4.070  -0.256  -0.426  1.00  0.00           C  
HETATM    5  C5  UNL     1       3.121   0.194   0.655  1.00  0.00           C  
HETATM    6  C6  UNL     1       3.345  -0.517   1.966  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.326   0.018   2.981  1.00  0.00           C  
HETATM    8  C8  UNL     1       0.966  -0.287   2.406  1.00  0.00           C  
HETATM    9  C9  UNL     1       0.116   0.673   2.143  1.00  0.00           C  
HETATM   10  C10 UNL     1      -1.236   0.506   1.583  1.00  0.00           C  
HETATM   11  O1  UNL     1      -1.842   1.586   1.432  1.00  0.00           O  
HETATM   12  C11 UNL     1      -1.734  -0.767   1.257  1.00  0.00           C  
HETATM   13  C12 UNL     1      -2.911  -1.056   0.831  1.00  0.00           C  
HETATM   14  C13 UNL     1      -3.999  -0.190   0.602  1.00  0.00           C  
HETATM   15  C14 UNL     1      -4.393   0.933   1.266  1.00  0.00           C  
HETATM   16  C15 UNL     1      -5.430   1.719   0.797  1.00  0.00           C  
HETATM   17  C16 UNL     1      -6.120   1.414  -0.355  1.00  0.00           C  
HETATM   18  O2  UNL     1      -7.153   2.198  -0.822  1.00  0.00           O  
HETATM   19  C17 UNL     1      -5.750   0.291  -1.040  1.00  0.00           C  
HETATM   20  O3  UNL     1      -6.436  -0.029  -2.199  1.00  0.00           O  
HETATM   21  C18 UNL     1      -6.053  -1.190  -2.907  1.00  0.00           C  
HETATM   22  C19 UNL     1      -4.737  -0.484  -0.592  1.00  0.00           C  
HETATM   23  H1  UNL     1       5.417   1.204  -2.192  1.00  0.00           H  
HETATM   24  H2  UNL     1       5.447  -0.322  -3.158  1.00  0.00           H  
HETATM   25  H3  UNL     1       6.997   0.628  -2.894  1.00  0.00           H  
HETATM   26  H4  UNL     1       7.445  -0.329  -0.893  1.00  0.00           H  
HETATM   27  H5  UNL     1       6.216  -1.585  -1.383  1.00  0.00           H  
HETATM   28  H6  UNL     1       5.656   1.098  -0.018  1.00  0.00           H  
HETATM   29  H7  UNL     1       5.768  -0.510   0.876  1.00  0.00           H  
HETATM   30  H8  UNL     1       3.808   0.253  -1.372  1.00  0.00           H  
HETATM   31  H9  UNL     1       3.944  -1.355  -0.639  1.00  0.00           H  
HETATM   32  H10 UNL     1       3.275   1.301   0.763  1.00  0.00           H  
HETATM   33  H11 UNL     1       2.086   0.066   0.284  1.00  0.00           H  
HETATM   34  H12 UNL     1       4.365  -0.425   2.336  1.00  0.00           H  
HETATM   35  H13 UNL     1       3.113  -1.591   1.794  1.00  0.00           H  
HETATM   36  H14 UNL     1       2.456   1.105   3.114  1.00  0.00           H  
HETATM   37  H15 UNL     1       2.466  -0.569   3.906  1.00  0.00           H  
HETATM   38  H16 UNL     1       0.686  -1.307   2.208  1.00  0.00           H  
HETATM   39  H17 UNL     1       0.485   1.689   2.379  1.00  0.00           H  
HETATM   40  H18 UNL     1      -0.995  -1.620   1.389  1.00  0.00           H  
HETATM   41  H19 UNL     1      -3.109  -2.165   0.613  1.00  0.00           H  
HETATM   42  H20 UNL     1      -3.937   1.158   2.214  1.00  0.00           H  
HETATM   43  H21 UNL     1      -5.731   2.620   1.342  1.00  0.00           H  
HETATM   44  H22 UNL     1      -7.648   1.957  -1.670  1.00  0.00           H  
HETATM   45  H23 UNL     1      -6.784  -1.329  -3.726  1.00  0.00           H  
HETATM   46  H24 UNL     1      -6.031  -2.085  -2.253  1.00  0.00           H  
HETATM   47  H25 UNL     1      -5.006  -1.075  -3.297  1.00  0.00           H  
HETATM   48  H26 UNL     1      -4.465  -1.366  -1.153  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   13   40
CONECT   13   14   41
CONECT   14   15   15   22
CONECT   15   16   42
CONECT   16   17   17   43
CONECT   17   18   19
CONECT   18   44
CONECT   19   20   22   22
CONECT   20   21
CONECT   21   45   46   47
CONECT   22   48
END

HMDB0033125
     RDKit          3D
[8]-Dehydroshogaol
 48 48  0  0  0  0  0  0  0  0999 V2000
    6.0218    0.2989   -2.4332 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3997   -0.4905   -1.2017 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5015   -0.0111   -0.0571 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0701   -0.2563   -0.4258 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1207    0.1940    0.6545 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3449   -0.5166    1.9656 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3261    0.0181    2.9812 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9662   -0.2871    2.4058 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1164    0.6731    2.1434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2357    0.5056    1.5826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8418    1.5858    1.4320 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7340   -0.7671    1.2569 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9106   -1.0558    0.8305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9990   -0.1902    0.6019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3929    0.9326    1.2662 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4298    1.7191    0.7973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1201    1.4139   -0.3548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1530    2.1977   -0.8218 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7497    0.2914   -1.0398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4362   -0.0291   -2.1986 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0529   -1.1901   -2.9068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7367   -0.4842   -0.5924 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4171    1.2041   -2.1923 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4471   -0.3216   -3.1577 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9969    0.6284   -2.8943 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4452   -0.3291   -0.8928 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2160   -1.5854   -1.3826 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6564    1.0984   -0.0179 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7685   -0.5104    0.8759 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8084    0.2527   -1.3722 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9440   -1.3545   -0.6392 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2745    1.3007    0.7628 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0862    0.0658    0.2842 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3645   -0.4248    2.3362 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1130   -1.5911    1.7938 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4564    1.1053    3.1142 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4658   -0.5686    3.9061 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6857   -1.3065    2.2080 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4851    1.6890    2.3791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9950   -1.6204    1.3891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1094   -2.1647    0.6133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9368    1.1584    2.2143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7313    2.6199    1.3419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6480    1.9569   -1.6702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7837   -1.3291   -3.7259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0310   -2.0850   -2.2530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0058   -1.0752   -3.2969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4651   -1.3655   -1.1531 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  2  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
 13 41  1  0
 15 42  1  0
 16 43  1  0
 18 44  1  0
 21 45  1  0
 21 46  1  0
 21 47  1  0
 22 48  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-(4-Hydroxy-3-methoxyphenyl)-1,4-dodecadien-3-one	HMDB
dehydro[8]-Shogaol	HMDB

Chemical Formula

C₁₉H₂₆O₃

Average Molecular Weight

302.4079

Monoisotopic Molecular Weight

302.188194698

IUPAC Name

(1Z,4E)-1-(4-hydroxy-3-methoxyphenyl)dodeca-1,4-dien-3-one

Traditional Name

(1Z,4E)-1-(4-hydroxy-3-methoxyphenyl)dodeca-1,4-dien-3-one

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C19H26O3/c1-3-4-5-6-7-8-9-10-17(20)13-11-16-12-14-18(21)19(15-16)22-2/h9-15,21H,3-8H2,1-2H3/b10-9+,13-11-

InChI Key

WTJRJJFXDZXSLU-LTCRFSFDSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxycinnamic acids and derivatives. Hydroxycinnamic acids and derivatives are compounds containing an cinnamic acid (or a derivative thereof) where the benzene ring is hydroxylated.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Hydroxycinnamic acids and derivatives

Alternative Parents

Substituents

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

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0033125)
Cell membrane (HMDB: HMDB0033125)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033125)

Source

Exogenous

Exogenous (HMDB: HMDB0033125)

Food

Food (HMDB: HMDB0033125)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Plant

Plant (HMDB: HMDB0033125)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0033125)

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	0.0015 g/L	ALOGPS
logP	5.73	ALOGPS
logP	5.81	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	9.51	ChemAxon
pKa (Strongest Basic)	-4.3	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	10	ChemAxon
Refractivity	92.98 m³·mol⁻¹	ChemAxon
Polarizability	36.05 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	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]+	186.875	30932474
DeepCCS	[M-H]-	184.517	30932474
DeepCCS	[M-2H]-	217.403	30932474
DeepCCS	[M+Na]+	192.986	30932474
AllCCS	[M+H]+	178.8	32859911
AllCCS	[M+H-H2O]+	175.5	32859911
AllCCS	[M+NH4]+	181.8	32859911
AllCCS	[M+Na]+	182.7	32859911
AllCCS	[M-H]-	180.1	32859911
AllCCS	[M+Na-2H]-	181.1	32859911
AllCCS	[M+HCOO]-	182.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
[8]-Dehydroshogaol	CCCCCCC\C=C\C(=O)\C=C/C1=CC(OC)=C(O)C=C1	4278.4	Standard polar	33892256
[8]-Dehydroshogaol	CCCCCCC\C=C\C(=O)\C=C/C1=CC(OC)=C(O)C=C1	2540.0	Standard non polar	33892256
[8]-Dehydroshogaol	CCCCCCC\C=C\C(=O)\C=C/C1=CC(OC)=C(O)C=C1	2778.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
[8]-Dehydroshogaol,1TMS,isomer #1	CCCCCCC/C=C/C(=O)/C=C\C1=CC=C(O[Si](C)(C)C)C(OC)=C1	2720.6	Semi standard non polar	33892256
[8]-Dehydroshogaol,1TBDMS,isomer #1	CCCCCCC/C=C/C(=O)/C=C\C1=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C1	2999.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - [8]-Dehydroshogaol GC-MS (Non-derivatized) - 70eV, Positive	splash10-05di-9540000000-cf500fcff2dd76210ba9	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - [8]-Dehydroshogaol GC-MS (1 TMS) - 70eV, Positive	splash10-0a4i-9135000000-7b82338fa79c30f4914c	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - [8]-Dehydroshogaol 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]-Dehydroshogaol 10V, Positive-QTOF	splash10-0udi-0429000000-0ce87b5f84f1360b65b2	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - [8]-Dehydroshogaol 20V, Positive-QTOF	splash10-1171-4921000000-8caace3f0c0287231a29	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - [8]-Dehydroshogaol 40V, Positive-QTOF	splash10-052f-9510000000-5eadaac2c2dd96db3538	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - [8]-Dehydroshogaol 10V, Negative-QTOF	splash10-0udi-0209000000-0b05e29a4eb7af68652d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - [8]-Dehydroshogaol 20V, Negative-QTOF	splash10-0udi-0925000000-4e870230e03dfcd1a60b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - [8]-Dehydroshogaol 40V, Negative-QTOF	splash10-0fc9-0930000000-c179775f5ad2d328a5d0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - [8]-Dehydroshogaol 10V, Positive-QTOF	splash10-0udi-0319000000-5b13daf116d66838d967	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - [8]-Dehydroshogaol 20V, Positive-QTOF	splash10-000i-3921000000-fe800f61dcdc8d2e67d1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - [8]-Dehydroshogaol 40V, Positive-QTOF	splash10-000b-2900000000-c99d97bd454f7eff590f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - [8]-Dehydroshogaol 10V, Negative-QTOF	splash10-0udi-0009000000-cf66b9953a0dfa4646bc	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - [8]-Dehydroshogaol 20V, Negative-QTOF	splash10-0uy0-0903000000-34feb8dfbaa035792d0d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - [8]-Dehydroshogaol 40V, Negative-QTOF	splash10-0012-1920000000-938813e464fc24c44829	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

FDB011125

KNApSAcK ID

Not Available

Chemspider ID

30776975

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131751378

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

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for [8]-Dehydroshogaol (HMDB0033125)

MOL for HMDB0033125 ([8]-Dehydroshogaol)

3D MOL for HMDB0033125 ([8]-Dehydroshogaol)

3D SDF for HMDB0033125 ([8]-Dehydroshogaol)

3D-SDF for HMDB0033125 ([8]-Dehydroshogaol)

PDB for HMDB0033125 ([8]-Dehydroshogaol)

3D PDB for HMDB0033125 ([8]-Dehydroshogaol)

SMILES for HMDB0033125 ([8]-Dehydroshogaol)

INCHI for HMDB0033125 ([8]-Dehydroshogaol)

Structure for HMDB0033125 ([8]-Dehydroshogaol)

3D Structure for HMDB0033125 ([8]-Dehydroshogaol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra