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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 02:55:15 UTC

Update Date

2022-03-07 02:56:56 UTC

HMDB ID

HMDB0041249

Secondary Accession Numbers

HMDB41249

Metabolite Identification

Common Name

6-Hydroxyshogaol

Description

6-Hydroxyshogaol 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. 6-Hydroxyshogaol has been detected, but not quantified in, herbs and spices. This could make 6-hydroxyshogaol a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 6-Hydroxyshogaol.

Structure

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

HMDB0041249
     RDKit          3D
6-Hydroxyshogaol
 45 45  0  0  0  0  0  0  0  0999 V2000
    7.5340    0.5885    0.8831 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1441    1.1487    0.6822 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4683    0.5647   -0.5133 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0091    0.8758   -0.6030 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2880    0.1727    0.5120 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6175   -1.2008    0.4208 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7838    0.1861    0.2174 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3717   -0.3653   -0.8894 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0454   -0.4761   -1.4553 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0011   -0.9851   -2.6743 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2218   -0.1192   -0.9505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6265   -1.0811    0.2101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1101   -1.0044    0.3945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8920   -2.2525    0.4382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1970   -2.1836    0.3256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9382   -1.0969    0.1731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2831   -1.0122    0.0869 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2835    0.1595    0.0969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0121    1.1432   -0.1112 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7789    2.1921   -0.3322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8731    0.1060    0.2294 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8248   -0.0880    0.0624 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2289    1.3928    1.0902 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4714   -0.1105    1.7868 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2538    2.2647    0.4278 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5538    1.0969    1.5675 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5850   -0.5924   -0.4451 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9882    0.8045   -1.4749 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6120    0.8708   -1.5888 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9081    2.0272   -0.2938 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5031    0.5480    1.4552 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3225   -1.6175   -0.3976 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0806    0.5742    0.9121 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2352   -0.7342   -1.5675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2138    0.9219   -0.4756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0614   -0.1256   -1.6593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0589   -0.9898    1.0750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4872   -2.1311   -0.2579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2679   -3.0995    0.5077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6863   -3.1985    0.3567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9935   -1.7381    0.1594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8777    2.0936    0.0274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5467    3.2041   -0.0899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1311    2.1641   -1.4600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2896    1.1021    0.2254 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
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 18 21  2  0
 21 13  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  0
  6 32  1  0
  7 33  1  0
  8 34  1  0
 11 35  1  0
 11 36  1  0
 12 37  1  0
 12 38  1  0
 14 39  1  0
 15 40  1  0
 17 41  1  0
 20 42  1  0
 20 43  1  0
 20 44  1  0
 21 45  1  0
M  END


  Mrv0541 05061312302D          

 21 21  0  0  0  0            999 V2000
   -7.1447    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
   -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
   -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
   -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   -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
   -4.2868    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
   -4.2868    0.0000    0.0000 O   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
  8  6  1  0  0  0  0
 10  9  2  0  0  0  0
 11  7  2  0  0  0  0
 13  6  1  0  0  0  0
 13  7  1  0  0  0  0
 13 12  2  0  0  0  0
 14  5  1  0  0  0  0
 14  9  1  0  0  0  0
 15  8  1  0  0  0  0
 15 10  1  0  0  0  0
 16 11  1  0  0  0  0
 17 12  1  0  0  0  0
 17 16  2  0  0  0  0
 18 14  1  0  0  0  0
 19 15  2  0  0  0  0
 20 16  1  0  0  0  0
 21  2  1  0  0  0  0
 21 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0041249

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C17H24O4/c1-3-4-5-14(18)9-10-15(19)8-6-13-7-11-16(20)17(12-13)21-2/h7,9-12,14,18,20H,3-6,8H2,1-2H3/b10-9+

> <INCHI_KEY>
SEWFXECKZBLANJ-MDZDMXLPSA-N

> <FORMULA>
C17H24O4

> <MOLECULAR_WEIGHT>
292.3701

> <EXACT_MASS>
292.167459256

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
33.676006264894895

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4E)-6-hydroxy-1-(4-hydroxy-3-methoxyphenyl)dec-4-en-3-one

> <ALOGPS_LOGP>
3.18

> <JCHEM_LOGP>
3.6143433003333345

> <ALOGPS_LOGS>
-3.47

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.854222162526522

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.945861274450236

> <JCHEM_PKA_STRONGEST_BASIC>
-2.862565572018516

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
84.20249999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.80e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4E)-6-hydroxy-1-(4-hydroxy-3-methoxyphenyl)dec-4-en-3-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0041249
     RDKit          3D
6-Hydroxyshogaol
 45 45  0  0  0  0  0  0  0  0999 V2000
    7.5340    0.5885    0.8831 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1441    1.1487    0.6822 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4683    0.5647   -0.5133 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0091    0.8758   -0.6030 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2880    0.1727    0.5120 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6175   -1.2008    0.4208 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7838    0.1861    0.2174 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3717   -0.3653   -0.8894 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0454   -0.4761   -1.4553 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0011   -0.9851   -2.6743 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2218   -0.1192   -0.9505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6265   -1.0811    0.2101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1101   -1.0044    0.3945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8920   -2.2525    0.4382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1970   -2.1836    0.3256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9382   -1.0969    0.1731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2831   -1.0122    0.0869 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2835    0.1595    0.0969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0121    1.1432   -0.1112 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7789    2.1921   -0.3322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8731    0.1060    0.2294 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8248   -0.0880    0.0624 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2289    1.3928    1.0902 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4714   -0.1105    1.7868 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2538    2.2647    0.4278 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5538    1.0969    1.5675 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5850   -0.5924   -0.4451 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9882    0.8045   -1.4749 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6120    0.8708   -1.5888 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9081    2.0272   -0.2938 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5031    0.5480    1.4552 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3225   -1.6175   -0.3976 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0806    0.5742    0.9121 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2352   -0.7342   -1.5675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2138    0.9219   -0.4756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0614   -0.1256   -1.6593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0589   -0.9898    1.0750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4872   -2.1311   -0.2579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2679   -3.0995    0.5077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6863   -3.1985    0.3567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9935   -1.7381    0.1594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8777    2.0936    0.0274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5467    3.2041   -0.0899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1311    2.1641   -1.4600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2896    1.1021    0.2254 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
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 18 21  2  0
 21 13  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  0
  6 32  1  0
  7 33  1  0
  8 34  1  0
 11 35  1  0
 11 36  1  0
 12 37  1  0
 12 38  1  0
 14 39  1  0
 15 40  1  0
 17 41  1  0
 20 42  1  0
 20 43  1  0
 20 44  1  0
 21 45  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     -13.337   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     -12.003   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -10.669   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -9.336   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.667   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  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -8.002   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -8.002   0.000   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -4.001   3.850   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2   21                                                            
CONECT    3    1    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4   14                                                       
CONECT    6    8   13                                                       
CONECT    7   11   13                                                       
CONECT    8    6   15                                                       
CONECT    9   10   14                                                       
CONECT   10    9   15                                                       
CONECT   11    7   16                                                       
CONECT   12   13   17                                                       
CONECT   13    6    7   12                                                  
CONECT   14    5    9   18                                                  
CONECT   15    8   10   19                                                  
CONECT   16   11   17   20                                                  
CONECT   17   12   16   21                                                  
CONECT   18   14                                                            
CONECT   19   15                                                            
CONECT   20   16                                                            
CONECT   21    2   17                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   42    0
END

COMPND    HMDB0041249
HETATM    1  C1  UNL     1       7.534   0.588   0.883  1.00  0.00           C  
HETATM    2  C2  UNL     1       6.144   1.149   0.682  1.00  0.00           C  
HETATM    3  C3  UNL     1       5.468   0.565  -0.513  1.00  0.00           C  
HETATM    4  C4  UNL     1       4.009   0.876  -0.603  1.00  0.00           C  
HETATM    5  C5  UNL     1       3.288   0.173   0.512  1.00  0.00           C  
HETATM    6  O1  UNL     1       3.617  -1.201   0.421  1.00  0.00           O  
HETATM    7  C6  UNL     1       1.784   0.186   0.217  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.372  -0.365  -0.889  1.00  0.00           C  
HETATM    9  C8  UNL     1       0.045  -0.476  -1.455  1.00  0.00           C  
HETATM   10  O2  UNL     1       0.001  -0.985  -2.674  1.00  0.00           O  
HETATM   11  C9  UNL     1      -1.222  -0.119  -0.951  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.627  -1.081   0.210  1.00  0.00           C  
HETATM   13  C11 UNL     1      -3.110  -1.004   0.395  1.00  0.00           C  
HETATM   14  C12 UNL     1      -3.892  -2.253   0.438  1.00  0.00           C  
HETATM   15  C13 UNL     1      -5.197  -2.184   0.326  1.00  0.00           C  
HETATM   16  C14 UNL     1      -5.938  -1.097   0.173  1.00  0.00           C  
HETATM   17  O3  UNL     1      -7.283  -1.012   0.087  1.00  0.00           O  
HETATM   18  C15 UNL     1      -5.283   0.160   0.097  1.00  0.00           C  
HETATM   19  O4  UNL     1      -6.012   1.143  -0.111  1.00  0.00           O  
HETATM   20  C16 UNL     1      -6.779   2.192  -0.332  1.00  0.00           C  
HETATM   21  C17 UNL     1      -3.873   0.106   0.229  1.00  0.00           C  
HETATM   22  H1  UNL     1       7.825  -0.088   0.062  1.00  0.00           H  
HETATM   23  H2  UNL     1       8.229   1.393   1.090  1.00  0.00           H  
HETATM   24  H3  UNL     1       7.471  -0.110   1.787  1.00  0.00           H  
HETATM   25  H4  UNL     1       6.254   2.265   0.428  1.00  0.00           H  
HETATM   26  H5  UNL     1       5.554   1.097   1.568  1.00  0.00           H  
HETATM   27  H6  UNL     1       5.585  -0.592  -0.445  1.00  0.00           H  
HETATM   28  H7  UNL     1       5.988   0.805  -1.475  1.00  0.00           H  
HETATM   29  H8  UNL     1       3.612   0.871  -1.589  1.00  0.00           H  
HETATM   30  H9  UNL     1       3.908   2.027  -0.294  1.00  0.00           H  
HETATM   31  H10 UNL     1       3.503   0.548   1.455  1.00  0.00           H  
HETATM   32  H11 UNL     1       3.323  -1.618  -0.398  1.00  0.00           H  
HETATM   33  H12 UNL     1       1.081   0.574   0.912  1.00  0.00           H  
HETATM   34  H13 UNL     1       2.235  -0.734  -1.567  1.00  0.00           H  
HETATM   35  H14 UNL     1      -1.214   0.922  -0.476  1.00  0.00           H  
HETATM   36  H15 UNL     1      -2.061  -0.126  -1.659  1.00  0.00           H  
HETATM   37  H16 UNL     1      -1.059  -0.990   1.075  1.00  0.00           H  
HETATM   38  H17 UNL     1      -1.487  -2.131  -0.258  1.00  0.00           H  
HETATM   39  H18 UNL     1      -3.268  -3.099   0.508  1.00  0.00           H  
HETATM   40  H19 UNL     1      -5.686  -3.198   0.357  1.00  0.00           H  
HETATM   41  H20 UNL     1      -7.993  -1.738   0.159  1.00  0.00           H  
HETATM   42  H21 UNL     1      -7.878   2.094   0.027  1.00  0.00           H  
HETATM   43  H22 UNL     1      -6.547   3.204  -0.090  1.00  0.00           H  
HETATM   44  H23 UNL     1      -7.131   2.164  -1.460  1.00  0.00           H  
HETATM   45  H24 UNL     1      -3.290   1.102   0.225  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3   25   26
CONECT    3    4   27   28
CONECT    4    5   29   30
CONECT    5    6    7   31
CONECT    6   32
CONECT    7    8    8   33
CONECT    8    9   34
CONECT    9   10   10   11
CONECT   11   12   35   36
CONECT   12   13   37   38
CONECT   13   14   14   21
CONECT   14   15   39
CONECT   15   16   16   40
CONECT   16   17   18
CONECT   17   41
CONECT   18   19   21   21
CONECT   19   20
CONECT   20   42   43   44
CONECT   21   45
END

HMDB0041249
     RDKit          3D
6-Hydroxyshogaol
 45 45  0  0  0  0  0  0  0  0999 V2000
    7.5340    0.5885    0.8831 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1441    1.1487    0.6822 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4683    0.5647   -0.5133 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0091    0.8758   -0.6030 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2880    0.1727    0.5120 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6175   -1.2008    0.4208 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7838    0.1861    0.2174 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3717   -0.3653   -0.8894 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0454   -0.4761   -1.4553 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0011   -0.9851   -2.6743 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2218   -0.1192   -0.9505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6265   -1.0811    0.2101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1101   -1.0044    0.3945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8920   -2.2525    0.4382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1970   -2.1836    0.3256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9382   -1.0969    0.1731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2831   -1.0122    0.0869 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2835    0.1595    0.0969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0121    1.1432   -0.1112 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7789    2.1921   -0.3322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8731    0.1060    0.2294 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8248   -0.0880    0.0624 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2289    1.3928    1.0902 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4714   -0.1105    1.7868 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2538    2.2647    0.4278 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5538    1.0969    1.5675 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5850   -0.5924   -0.4451 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9882    0.8045   -1.4749 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6120    0.8708   -1.5888 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9081    2.0272   -0.2938 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5031    0.5480    1.4552 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3225   -1.6175   -0.3976 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0806    0.5742    0.9121 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2352   -0.7342   -1.5675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2138    0.9219   -0.4756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0614   -0.1256   -1.6593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0589   -0.9898    1.0750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4872   -2.1311   -0.2579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2679   -3.0995    0.5077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6863   -3.1985    0.3567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9935   -1.7381    0.1594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8777    2.0936    0.0274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5467    3.2041   -0.0899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1311    2.1641   -1.4600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2896    1.1021    0.2254 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
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 18 21  2  0
 21 13  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  0
  6 32  1  0
  7 33  1  0
  8 34  1  0
 11 35  1  0
 11 36  1  0
 12 37  1  0
 12 38  1  0
 14 39  1  0
 15 40  1  0
 17 41  1  0
 20 42  1  0
 20 43  1  0
 20 44  1  0
 21 45  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
6-Hydroxy-1-(4-hydroxy-3-methoxyphenyl)-4-decen-3-one	HMDB

Chemical Formula

C₁₇H₂₄O₄

Average Molecular Weight

292.3701

Monoisotopic Molecular Weight

292.167459256

IUPAC Name

(4E)-6-hydroxy-1-(4-hydroxy-3-methoxyphenyl)dec-4-en-3-one

Traditional Name

(4E)-6-hydroxy-1-(4-hydroxy-3-methoxyphenyl)dec-4-en-3-one

CAS Registry Number

143114-93-6

SMILES

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

InChI Identifier

InChI=1S/C17H24O4/c1-3-4-5-14(18)9-10-15(19)8-6-13-7-11-16(20)17(12-13)21-2/h7,9-12,14,18,20H,3-6,8H2,1-2H3/b10-9+

InChI Key

SEWFXECKZBLANJ-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
Fatty alcohol
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Monocyclic benzene moiety
Fatty acyl
Enone
Acryloyl-group
Alpha,beta-unsaturated ketone
Ketone
Secondary alcohol
Ether
Alcohol
Organooxygen compound
Hydrocarbon derivative
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

Cell membrane (HMDB: HMDB0041249)

Cellular substructure

Membrane (HMDB: HMDB0041249)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0041249)

Source

Exogenous

Food

Food (HMDB: HMDB0041249)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Plant

Plant (HMDB: HMDB0041249)

Not Available

Nutrient (HMDB: HMDB0041249)

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	182.1 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	0.098 g/L	ALOGPS
logP	3.18	ALOGPS
logP	3.61	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	9.95	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	84.2 m³·mol⁻¹	ChemAxon
Polarizability	33.68 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
DeepCCS	[M+H]+	178.771	30932474
DeepCCS	[M-H]-	176.413	30932474
DeepCCS	[M-2H]-	209.299	30932474
DeepCCS	[M+Na]+	184.864	30932474
AllCCS	[M+H]+	174.5	32859911
AllCCS	[M+H-H2O]+	171.2	32859911
AllCCS	[M+NH4]+	177.6	32859911
AllCCS	[M+Na]+	178.5	32859911
AllCCS	[M-H]-	175.2	32859911
AllCCS	[M+Na-2H]-	176.0	32859911
AllCCS	[M+HCOO]-	177.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
6-Hydroxyshogaol	CCCCC(O)\C=C\C(=O)CCC1=CC(OC)=C(O)C=C1	4217.9	Standard polar	33892256
6-Hydroxyshogaol	CCCCC(O)\C=C\C(=O)CCC1=CC(OC)=C(O)C=C1	2398.4	Standard non polar	33892256
6-Hydroxyshogaol	CCCCC(O)\C=C\C(=O)CCC1=CC(OC)=C(O)C=C1	2480.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
6-Hydroxyshogaol,1TMS,isomer #1	CCCCC(/C=C/C(=O)CCC1=CC=C(O)C(OC)=C1)O[Si](C)(C)C	2486.2	Semi standard non polar	33892256
6-Hydroxyshogaol,1TMS,isomer #2	CCCCC(O)/C=C/C(=O)CCC1=CC=C(O[Si](C)(C)C)C(OC)=C1	2518.1	Semi standard non polar	33892256
6-Hydroxyshogaol,1TMS,isomer #3	CCCCC(O)/C=C/C(=CCC1=CC=C(O)C(OC)=C1)O[Si](C)(C)C	2693.4	Semi standard non polar	33892256
6-Hydroxyshogaol,2TMS,isomer #1	CCCCC(/C=C/C(=O)CCC1=CC=C(O[Si](C)(C)C)C(OC)=C1)O[Si](C)(C)C	2495.2	Semi standard non polar	33892256
6-Hydroxyshogaol,2TMS,isomer #2	CCCCC(/C=C/C(=CCC1=CC=C(O)C(OC)=C1)O[Si](C)(C)C)O[Si](C)(C)C	2680.5	Semi standard non polar	33892256
6-Hydroxyshogaol,2TMS,isomer #3	CCCCC(O)/C=C/C(=CCC1=CC=C(O[Si](C)(C)C)C(OC)=C1)O[Si](C)(C)C	2685.8	Semi standard non polar	33892256
6-Hydroxyshogaol,3TMS,isomer #1	CCCCC(/C=C/C(=CCC1=CC=C(O[Si](C)(C)C)C(OC)=C1)O[Si](C)(C)C)O[Si](C)(C)C	2707.5	Semi standard non polar	33892256
6-Hydroxyshogaol,3TMS,isomer #1	CCCCC(/C=C/C(=CCC1=CC=C(O[Si](C)(C)C)C(OC)=C1)O[Si](C)(C)C)O[Si](C)(C)C	2480.5	Standard non polar	33892256
6-Hydroxyshogaol,1TBDMS,isomer #1	CCCCC(/C=C/C(=O)CCC1=CC=C(O)C(OC)=C1)O[Si](C)(C)C(C)(C)C	2743.8	Semi standard non polar	33892256
6-Hydroxyshogaol,1TBDMS,isomer #2	CCCCC(O)/C=C/C(=O)CCC1=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C1	2776.6	Semi standard non polar	33892256
6-Hydroxyshogaol,1TBDMS,isomer #3	CCCCC(O)/C=C/C(=CCC1=CC=C(O)C(OC)=C1)O[Si](C)(C)C(C)(C)C	2957.1	Semi standard non polar	33892256
6-Hydroxyshogaol,2TBDMS,isomer #1	CCCCC(/C=C/C(=O)CCC1=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C1)O[Si](C)(C)C(C)(C)C	2974.1	Semi standard non polar	33892256
6-Hydroxyshogaol,2TBDMS,isomer #2	CCCCC(/C=C/C(=CCC1=CC=C(O)C(OC)=C1)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3175.1	Semi standard non polar	33892256
6-Hydroxyshogaol,2TBDMS,isomer #3	CCCCC(O)/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	3199.0	Semi standard non polar	33892256
6-Hydroxyshogaol,3TBDMS,isomer #1	CCCCC(/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)O[Si](C)(C)C(C)(C)C	3393.4	Semi standard non polar	33892256
6-Hydroxyshogaol,3TBDMS,isomer #1	CCCCC(/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)O[Si](C)(C)C(C)(C)C	3073.1	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 6-Hydroxyshogaol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4l-9650000000-e9a92ffdb0520a57df20	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6-Hydroxyshogaol GC-MS (2 TMS) - 70eV, Positive	splash10-00di-9484700000-13b49ab356704bb7e710	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6-Hydroxyshogaol 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 - 6-Hydroxyshogaol 10V, Positive-QTOF	splash10-004l-0190000000-e5166111300a8cdb74ca	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Hydroxyshogaol 20V, Positive-QTOF	splash10-054x-5950000000-7b2ff27efe4c4521e7ce	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Hydroxyshogaol 40V, Positive-QTOF	splash10-0k9f-9410000000-2169845180ebf09200c0	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Hydroxyshogaol 10V, Negative-QTOF	splash10-0006-0090000000-0d597d8cf9882c53e0c7	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Hydroxyshogaol 20V, Negative-QTOF	splash10-0006-2980000000-db88137d4e80a4c6b9fe	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Hydroxyshogaol 40V, Negative-QTOF	splash10-0udr-5910000000-633749554bf92a2b71e7	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Hydroxyshogaol 10V, Negative-QTOF	splash10-0006-0090000000-979689e66dc132433dec	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Hydroxyshogaol 20V, Negative-QTOF	splash10-000i-1920000000-ebc5a0721a5808010b4f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Hydroxyshogaol 40V, Negative-QTOF	splash10-00tr-4900000000-87e2dc90437f66336961	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Hydroxyshogaol 10V, Positive-QTOF	splash10-004i-0690000000-cbdd16df465fa672bdf3	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Hydroxyshogaol 20V, Positive-QTOF	splash10-000i-0930000000-1732af6865a59a9d22cd	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Hydroxyshogaol 40V, Positive-QTOF	splash10-000i-2900000000-27dbbf2cf38bc4b6d42e	2021-09-24	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

FDB021157

KNApSAcK ID

Not Available

Chemspider ID

9315994

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11140882

PDB ID

Not Available

ChEBI ID

172141

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1890851

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 6-Hydroxyshogaol (HMDB0041249)

MOL for HMDB0041249 (6-Hydroxyshogaol)

3D MOL for HMDB0041249 (6-Hydroxyshogaol)

3D SDF for HMDB0041249 (6-Hydroxyshogaol)

3D-SDF for HMDB0041249 (6-Hydroxyshogaol)

PDB for HMDB0041249 (6-Hydroxyshogaol)

3D PDB for HMDB0041249 (6-Hydroxyshogaol)

SMILES for HMDB0041249 (6-Hydroxyshogaol)

INCHI for HMDB0041249 (6-Hydroxyshogaol)

Structure for HMDB0041249 (6-Hydroxyshogaol)

3D Structure for HMDB0041249 (6-Hydroxyshogaol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra