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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:53:41 UTC

Update Date

2022-03-07 02:53:35 UTC

HMDB ID

HMDB0033090

Secondary Accession Numbers

HMDB33090

Metabolite Identification

Common Name

[6]-Dehydroshogaol

Description

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

Structure

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

HMDB0033090
     RDKit          3D
[6]-Dehydroshogaol
 42 42  0  0  0  0  0  0  0  0999 V2000
   -5.2995    0.5379   -0.3268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4096   -0.8585   -0.7858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2681   -1.7807   -0.6339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7706   -2.0768    0.7418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2050   -0.9432    1.4998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0090   -0.3347    0.8398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8423   -0.2860    1.4301 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3924    0.2967    0.8523 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4089    0.2365    1.5921 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3599    0.8805   -0.4481 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3633    1.3603   -1.1113 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7102    1.3869   -0.6977 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4567    2.5259   -1.0629 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8077    2.6301   -0.8471 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4925    1.6050   -0.2549 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8602    1.6727   -0.0175 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8080    0.4865    0.1112 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4879   -0.5559    0.7102 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7672   -1.7076    1.0844 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4209    0.3943   -0.1189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2819    0.9604   -0.3586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8903    1.1767   -1.0772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8101    0.7046    0.6590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6432   -0.8307   -1.9017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3513   -1.3156   -0.3619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5485   -2.7314   -1.1794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3845   -1.3994   -1.2148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6721   -2.5052    1.2957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0702   -2.9691    0.7297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9264   -0.1459    1.6899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9263   -1.3254    2.5194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1227    0.0645   -0.1504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8069   -0.7224    2.4376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6379    0.9447   -0.9724 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1021    1.8048   -2.1431 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9713    3.3573   -1.5296 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3752    3.5061   -1.1293 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3495    2.5088   -0.2956 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9413   -1.3538    1.7678 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4164   -2.3363    1.7616 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3939   -2.2861    0.2344 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9909   -0.5765    0.1379 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 17 20  2  0
 20 12  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  7 33  1  0
 10 34  1  0
 11 35  1  0
 13 36  1  0
 14 37  1  0
 16 38  1  0
 19 39  1  0
 19 40  1  0
 19 41  1  0
 20 42  1  0
M  END


  Mrv0541 05061306542D          

 20 20  0  0  0  0            999 V2000
   -6.4302   -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
   -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  2  0  0  0  0
 11  9  2  0  0  0  0
 12 10  2  0  0  0  0
 14  9  1  0  0  0  0
 14 10  1  0  0  0  0
 14 13  2  0  0  0  0
 15  8  1  0  0  0  0
 15 11  1  0  0  0  0
 16 12  1  0  0  0  0
 17 13  1  0  0  0  0
 17 16  2  0  0  0  0
 18 15  2  0  0  0  0
 19 16  1  0  0  0  0
 20  2  1  0  0  0  0
 20 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033090

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C17H22O3/c1-3-4-5-6-7-8-15(18)11-9-14-10-12-16(19)17(13-14)20-2/h7-13,19H,3-6H2,1-2H3/b8-7+,11-9-

> <INCHI_KEY>
JLXKTAQNHHXFHL-OHFYBLQUSA-N

> <FORMULA>
C17H22O3

> <MOLECULAR_WEIGHT>
274.3548

> <EXACT_MASS>
274.15689457

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
31.821499995724224

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
4.78

> <JCHEM_LOGP>
4.925677857000001

> <ALOGPS_LOGS>
-4.62

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.505000698021703

> <JCHEM_PKA_STRONGEST_BASIC>
-4.3209350841267335

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
83.78029999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.51e-03 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0033090
     RDKit          3D
[6]-Dehydroshogaol
 42 42  0  0  0  0  0  0  0  0999 V2000
   -5.2995    0.5379   -0.3268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4096   -0.8585   -0.7858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2681   -1.7807   -0.6339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7706   -2.0768    0.7418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2050   -0.9432    1.4998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0090   -0.3347    0.8398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8423   -0.2860    1.4301 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3924    0.2967    0.8523 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4089    0.2365    1.5921 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3599    0.8805   -0.4481 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3633    1.3603   -1.1113 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7102    1.3869   -0.6977 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4567    2.5259   -1.0629 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8077    2.6301   -0.8471 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4925    1.6050   -0.2549 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8602    1.6727   -0.0175 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8080    0.4865    0.1112 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4879   -0.5559    0.7102 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7672   -1.7076    1.0844 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4209    0.3943   -0.1189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2819    0.9604   -0.3586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8903    1.1767   -1.0772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8101    0.7046    0.6590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6432   -0.8307   -1.9017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3513   -1.3156   -0.3619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5485   -2.7314   -1.1794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3845   -1.3994   -1.2148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6721   -2.5052    1.2957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0702   -2.9691    0.7297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9264   -0.1459    1.6899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9263   -1.3254    2.5194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1227    0.0645   -0.1504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8069   -0.7224    2.4376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6379    0.9447   -0.9724 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1021    1.8048   -2.1431 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9713    3.3573   -1.5296 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3752    3.5061   -1.1293 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3495    2.5088   -0.2956 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9413   -1.3538    1.7678 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4164   -2.3363    1.7616 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3939   -2.2861    0.2344 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9909   -0.5765    0.1379 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 17 20  2  0
 20 12  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  7 33  1  0
 10 34  1  0
 11 35  1  0
 13 36  1  0
 14 37  1  0
 16 38  1  0
 19 39  1  0
 19 40  1  0
 19 41  1  0
 20 42  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     -12.003  -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     -10.669   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -8.002   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.335   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.667   0.000   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      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2   20                                                            
CONECT    3    1    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7   15                                                       
CONECT    9   11   14                                                       
CONECT   10   12   14                                                       
CONECT   11    9   15                                                       
CONECT   12   10   16                                                       
CONECT   13   14   17                                                       
CONECT   14    9   10   13                                                  
CONECT   15    8   11   18                                                  
CONECT   16   12   17   19                                                  
CONECT   17   13   16   20                                                  
CONECT   18   15                                                            
CONECT   19   16                                                            
CONECT   20    2   17                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   40    0
END

COMPND    HMDB0033090
HETATM    1  C1  UNL     1      -5.299   0.538  -0.327  1.00  0.00           C  
HETATM    2  C2  UNL     1      -5.410  -0.858  -0.786  1.00  0.00           C  
HETATM    3  C3  UNL     1      -4.268  -1.781  -0.634  1.00  0.00           C  
HETATM    4  C4  UNL     1      -3.771  -2.077   0.742  1.00  0.00           C  
HETATM    5  C5  UNL     1      -3.205  -0.943   1.500  1.00  0.00           C  
HETATM    6  C6  UNL     1      -2.009  -0.335   0.840  1.00  0.00           C  
HETATM    7  C7  UNL     1      -0.842  -0.286   1.430  1.00  0.00           C  
HETATM    8  C8  UNL     1       0.392   0.297   0.852  1.00  0.00           C  
HETATM    9  O1  UNL     1       1.409   0.236   1.592  1.00  0.00           O  
HETATM   10  C9  UNL     1       0.360   0.881  -0.448  1.00  0.00           C  
HETATM   11  C10 UNL     1       1.363   1.360  -1.111  1.00  0.00           C  
HETATM   12  C11 UNL     1       2.710   1.387  -0.698  1.00  0.00           C  
HETATM   13  C12 UNL     1       3.457   2.526  -1.063  1.00  0.00           C  
HETATM   14  C13 UNL     1       4.808   2.630  -0.847  1.00  0.00           C  
HETATM   15  C14 UNL     1       5.492   1.605  -0.255  1.00  0.00           C  
HETATM   16  O2  UNL     1       6.860   1.673  -0.018  1.00  0.00           O  
HETATM   17  C15 UNL     1       4.808   0.486   0.111  1.00  0.00           C  
HETATM   18  O3  UNL     1       5.488  -0.556   0.710  1.00  0.00           O  
HETATM   19  C16 UNL     1       4.767  -1.708   1.084  1.00  0.00           C  
HETATM   20  C17 UNL     1       3.421   0.394  -0.119  1.00  0.00           C  
HETATM   21  H1  UNL     1      -4.282   0.960  -0.359  1.00  0.00           H  
HETATM   22  H2  UNL     1      -5.890   1.177  -1.077  1.00  0.00           H  
HETATM   23  H3  UNL     1      -5.810   0.705   0.659  1.00  0.00           H  
HETATM   24  H4  UNL     1      -5.643  -0.831  -1.902  1.00  0.00           H  
HETATM   25  H5  UNL     1      -6.351  -1.316  -0.362  1.00  0.00           H  
HETATM   26  H6  UNL     1      -4.548  -2.731  -1.179  1.00  0.00           H  
HETATM   27  H7  UNL     1      -3.385  -1.399  -1.215  1.00  0.00           H  
HETATM   28  H8  UNL     1      -4.672  -2.505   1.296  1.00  0.00           H  
HETATM   29  H9  UNL     1      -3.070  -2.969   0.730  1.00  0.00           H  
HETATM   30  H10 UNL     1      -3.926  -0.146   1.690  1.00  0.00           H  
HETATM   31  H11 UNL     1      -2.926  -1.325   2.519  1.00  0.00           H  
HETATM   32  H12 UNL     1      -2.123   0.064  -0.150  1.00  0.00           H  
HETATM   33  H13 UNL     1      -0.807  -0.722   2.438  1.00  0.00           H  
HETATM   34  H14 UNL     1      -0.638   0.945  -0.972  1.00  0.00           H  
HETATM   35  H15 UNL     1       1.102   1.805  -2.143  1.00  0.00           H  
HETATM   36  H16 UNL     1       2.971   3.357  -1.530  1.00  0.00           H  
HETATM   37  H17 UNL     1       5.375   3.506  -1.129  1.00  0.00           H  
HETATM   38  H18 UNL     1       7.349   2.509  -0.296  1.00  0.00           H  
HETATM   39  H19 UNL     1       3.941  -1.354   1.768  1.00  0.00           H  
HETATM   40  H20 UNL     1       5.416  -2.336   1.762  1.00  0.00           H  
HETATM   41  H21 UNL     1       4.394  -2.286   0.234  1.00  0.00           H  
HETATM   42  H22 UNL     1       2.991  -0.577   0.138  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3   24   25
CONECT    3    4   26   27
CONECT    4    5   28   29
CONECT    5    6   30   31
CONECT    6    7    7   32
CONECT    7    8   33
CONECT    8    9    9   10
CONECT   10   11   11   34
CONECT   11   12   35
CONECT   12   13   13   20
CONECT   13   14   36
CONECT   14   15   15   37
CONECT   15   16   17
CONECT   16   38
CONECT   17   18   20   20
CONECT   18   19
CONECT   19   39   40   41
CONECT   20   42
END

HMDB0033090
     RDKit          3D
[6]-Dehydroshogaol
 42 42  0  0  0  0  0  0  0  0999 V2000
   -5.2995    0.5379   -0.3268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4096   -0.8585   -0.7858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2681   -1.7807   -0.6339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7706   -2.0768    0.7418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2050   -0.9432    1.4998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0090   -0.3347    0.8398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8423   -0.2860    1.4301 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3924    0.2967    0.8523 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4089    0.2365    1.5921 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3599    0.8805   -0.4481 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3633    1.3603   -1.1113 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7102    1.3869   -0.6977 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4567    2.5259   -1.0629 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8077    2.6301   -0.8471 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4925    1.6050   -0.2549 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8602    1.6727   -0.0175 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8080    0.4865    0.1112 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4879   -0.5559    0.7102 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7672   -1.7076    1.0844 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4209    0.3943   -0.1189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2819    0.9604   -0.3586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8903    1.1767   -1.0772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8101    0.7046    0.6590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6432   -0.8307   -1.9017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3513   -1.3156   -0.3619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5485   -2.7314   -1.1794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3845   -1.3994   -1.2148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6721   -2.5052    1.2957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0702   -2.9691    0.7297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9264   -0.1459    1.6899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9263   -1.3254    2.5194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1227    0.0645   -0.1504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8069   -0.7224    2.4376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6379    0.9447   -0.9724 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1021    1.8048   -2.1431 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9713    3.3573   -1.5296 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3752    3.5061   -1.1293 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3495    2.5088   -0.2956 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9413   -1.3538    1.7678 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4164   -2.3363    1.7616 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3939   -2.2861    0.2344 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9909   -0.5765    0.1379 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 17 20  2  0
 20 12  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  7 33  1  0
 10 34  1  0
 11 35  1  0
 13 36  1  0
 14 37  1  0
 16 38  1  0
 19 39  1  0
 19 40  1  0
 19 41  1  0
 20 42  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-(4-Hydroxy-3-methoxyphenyl)-1,4-decadien-3-one	HMDB
[6]Dehydroshogaol	HMDB

Chemical Formula

C₁₇H₂₂O₃

Average Molecular Weight

274.3548

Monoisotopic Molecular Weight

274.15689457

IUPAC Name

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

Traditional Name

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

CAS Registry Number

212137-55-8

SMILES

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

InChI Identifier

InChI=1S/C17H22O3/c1-3-4-5-6-7-8-15(18)11-9-14-10-12-16(19)17(13-14)20-2/h7-13,19H,3-6H2,1-2H3/b8-7+,11-9-

InChI Key

JLXKTAQNHHXFHL-OHFYBLQUSA-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: HMDB0033090)
Cell membrane (HMDB: HMDB0033090)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033090)

Source

Exogenous

Exogenous (HMDB: HMDB0033090)

Food

Food (HMDB: HMDB0033090)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Plant

Plant (HMDB: HMDB0033090)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0033090)

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	5.29 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	0.0065 g/L	ALOGPS
logP	4.78	ALOGPS
logP	4.93	ChemAxon
logS	-4.6	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	8	ChemAxon
Refractivity	83.78 m³·mol⁻¹	ChemAxon
Polarizability	31.82 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]+	177.425	30932474
DeepCCS	[M-H]-	175.067	30932474
DeepCCS	[M-2H]-	207.952	30932474
DeepCCS	[M+Na]+	183.518	30932474
AllCCS	[M+H]+	169.3	32859911
AllCCS	[M+H-H2O]+	165.7	32859911
AllCCS	[M+NH4]+	172.5	32859911
AllCCS	[M+Na]+	173.5	32859911
AllCCS	[M-H]-	171.1	32859911
AllCCS	[M+Na-2H]-	171.8	32859911
AllCCS	[M+HCOO]-	172.6	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	9.18 minutes	32390414
Predicted by Siyang on May 30, 2022	16.6948 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.91 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2616.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	425.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	202.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	225.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	387.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	813.4 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	641.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	109.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1743.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	548.4 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1442.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	513.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	464.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	381.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	416.6 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
[6]-Dehydroshogaol	CCCCC\C=C\C(=O)\C=C/C1=CC(OC)=C(O)C=C1	4030.7	Standard polar	33892256
[6]-Dehydroshogaol	CCCCC\C=C\C(=O)\C=C/C1=CC(OC)=C(O)C=C1	2350.4	Standard non polar	33892256
[6]-Dehydroshogaol	CCCCC\C=C\C(=O)\C=C/C1=CC(OC)=C(O)C=C1	2546.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
[6]-Dehydroshogaol,1TMS,isomer #1	CCCCC/C=C/C(=O)/C=C\C1=CC=C(O[Si](C)(C)C)C(OC)=C1	2522.5	Semi standard non polar	33892256
[6]-Dehydroshogaol,1TBDMS,isomer #1	CCCCC/C=C/C(=O)/C=C\C1=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C1	2804.0	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 - [6]-Dehydroshogaol GC-MS (Non-derivatized) - 70eV, Positive	splash10-004i-9750000000-442ec24245fe40fbaca7	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - [6]-Dehydroshogaol GC-MS (1 TMS) - 70eV, Positive	splash10-05cv-9176000000-072c257a995978e37510	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - [6]-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 - [6]-Dehydroshogaol 10V, Positive-QTOF	splash10-004i-1290000000-4f96d61719e0c96dfe97	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - [6]-Dehydroshogaol 20V, Positive-QTOF	splash10-005j-9750000000-1b677b0391141143e7d8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - [6]-Dehydroshogaol 40V, Positive-QTOF	splash10-052f-9410000000-35068df406e554e428cc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - [6]-Dehydroshogaol 10V, Negative-QTOF	splash10-00di-0190000000-8235e881817e86ce61bb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - [6]-Dehydroshogaol 20V, Negative-QTOF	splash10-00di-2890000000-e8d3712320df614e641a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - [6]-Dehydroshogaol 40V, Negative-QTOF	splash10-053b-4930000000-41e13ccfb6b56ec2d3fb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - [6]-Dehydroshogaol 10V, Negative-QTOF	splash10-00di-0290000000-63f4d8365b58968a3159	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - [6]-Dehydroshogaol 20V, Negative-QTOF	splash10-00di-0920000000-139473a74fefe580816f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - [6]-Dehydroshogaol 40V, Negative-QTOF	splash10-000b-3920000000-dad04e0d8e491e0e27ca	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - [6]-Dehydroshogaol 10V, Positive-QTOF	splash10-004i-0390000000-5c024016bbdac92c0c1a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - [6]-Dehydroshogaol 20V, Positive-QTOF	splash10-05tr-6930000000-d937f259a736463d51dc	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - [6]-Dehydroshogaol 40V, Positive-QTOF	splash10-059m-4900000000-24ee274db2d810053bb0	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

FDB011085

KNApSAcK ID

C00044042

Chemspider ID

30776971

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131751371

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1833251

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]-Dehydroshogaol (HMDB0033090)

MOL for HMDB0033090 ([6]-Dehydroshogaol)

3D MOL for HMDB0033090 ([6]-Dehydroshogaol)

3D SDF for HMDB0033090 ([6]-Dehydroshogaol)

3D-SDF for HMDB0033090 ([6]-Dehydroshogaol)

PDB for HMDB0033090 ([6]-Dehydroshogaol)

3D PDB for HMDB0033090 ([6]-Dehydroshogaol)

SMILES for HMDB0033090 ([6]-Dehydroshogaol)

INCHI for HMDB0033090 ([6]-Dehydroshogaol)

Structure for HMDB0033090 ([6]-Dehydroshogaol)

3D Structure for HMDB0033090 ([6]-Dehydroshogaol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra