Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 06:49:10 UTC

Update Date

2021-09-23 06:49:10 UTC

HMDB ID

HMDB0302125

Secondary Accession Numbers

None

Metabolite Identification

Common Name

[4]-Gingerol

Description

[4]-gingerol is a member of the class of compounds known as gingerols. Gingerols are compounds containing a gingerol moiety, which is structurally characterized by a 4-hydroxy-3-methoxyphenyl group substituted at the C6 carbon atom by a 5-hydroxy-alkane-3-one. [4]-gingerol is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). [4]-gingerol can be found in ginger, which makes [4]-gingerol a potential biomarker for the consumption of this food product.

Structure

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

HMDB0302125
     RDKit          3D
[4]-Gingerol
 41 41  0  0  0  0  0  0  0  0999 V2000
    3.5095    1.8441   -1.0537 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6748    0.9463   -0.9005 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4882   -0.5071   -1.0797 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5759   -1.2391   -0.1792 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6295   -2.6125   -0.5856 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1372   -0.8642   -0.3590 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2674   -1.6547    0.5790 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7225   -2.4530    1.3545 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1925   -1.4101    0.5121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6657   -0.3845    1.5229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1385   -0.2603    1.3237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0031   -1.0528    2.0350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3459   -0.9235    1.8304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8450   -0.0272    0.9376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2139    0.1011    0.7324 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0053    0.8058    0.1857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5624    1.6903   -0.7002 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8446    2.5687   -1.5073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6583    0.6494    0.4169 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0638    2.1618   -0.0643 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9332    2.8435   -1.4265 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7739    1.5796   -1.8139 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4534    1.2651   -1.6634 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1754    1.1836    0.0748 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5352   -0.9574   -1.0346 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2014   -0.7189   -2.1580 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8890   -1.2677    0.8752 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0923   -2.6708   -1.4107 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8796    0.1749   -0.1758 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8457   -1.1218   -1.3871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7056   -2.3858    0.6864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4622   -1.1128   -0.5177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4637   -0.7565    2.5382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2330    0.5995    1.3435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6021   -1.7620    2.7425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0171   -1.5624    2.4061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8463   -0.4857    1.2593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9268    3.5950   -1.0389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7972    2.2805   -1.6604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3630    2.6318   -2.5024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9557    1.2699   -0.1372 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
  4  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 16 19  2  0
 19 11  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  2 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  1
  5 28  1  0
  6 29  1  0
  6 30  1  0
  9 31  1  0
  9 32  1  0
 10 33  1  0
 10 34  1  0
 12 35  1  0
 13 36  1  0
 15 37  1  0
 18 38  1  0
 18 39  1  0
 18 40  1  0
 19 41  1  0
M  END


  Mrv0541 02241212282D          

 19 19  0  0  0  0            999 V2000
   -4.4786    1.8268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1930    1.4143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1930    0.5893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4786    0.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7641    0.5893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7641    1.4143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9075    0.1768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4786   -0.6482    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7641   -1.0607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0496    1.8268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3352    1.4143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6207    1.8268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9062    1.4143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1918    1.8268    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5227    1.4143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2372    1.8268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9517    1.4143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6207    2.6518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1918    2.6518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  3  7  1  0  0  0  0
  4  8  1  0  0  0  0
  8  9  1  0  0  0  0
  6 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 12 18  2  0  0  0  0
 14 19  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0302125

> <DATABASE_NAME>
hmdb

> <SMILES>
CCC[C@H](O)CC(=O)CCC1=CC(OC)=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O4/c1-3-4-12(16)10-13(17)7-5-11-6-8-14(18)15(9-11)19-2/h6,8-9,12,16,18H,3-5,7,10H2,1-2H3/t12-/m0/s1

> <INCHI_KEY>
GDRKZARFCIYVCI-LBPRGKRZSA-N

> <FORMULA>
C15H22O4

> <MOLECULAR_WEIGHT>
266.3328

> <EXACT_MASS>
266.151809192

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
29.701524971542845

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5S)-5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)octan-3-one

> <ALOGPS_LOGP>
2.51

> <JCHEM_LOGP>
2.7273824806666678

> <ALOGPS_LOGS>
-3.18

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.082126244726588

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.945873123461713

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7612567177123992

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
73.9072

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.77e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5S)-5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)octan-3-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0302125
     RDKit          3D
[4]-Gingerol
 41 41  0  0  0  0  0  0  0  0999 V2000
    3.5095    1.8441   -1.0537 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6748    0.9463   -0.9005 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4882   -0.5071   -1.0797 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5759   -1.2391   -0.1792 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6295   -2.6125   -0.5856 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1372   -0.8642   -0.3590 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2674   -1.6547    0.5790 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7225   -2.4530    1.3545 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1925   -1.4101    0.5121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6657   -0.3845    1.5229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1385   -0.2603    1.3237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0031   -1.0528    2.0350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3459   -0.9235    1.8304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8450   -0.0272    0.9376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2139    0.1011    0.7324 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0053    0.8058    0.1857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5624    1.6903   -0.7002 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8446    2.5687   -1.5073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6583    0.6494    0.4169 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0638    2.1618   -0.0643 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9332    2.8435   -1.4265 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7739    1.5796   -1.8139 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4534    1.2651   -1.6634 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1754    1.1836    0.0748 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5352   -0.9574   -1.0346 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2014   -0.7189   -2.1580 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8890   -1.2677    0.8752 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0923   -2.6708   -1.4107 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8796    0.1749   -0.1758 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8457   -1.1218   -1.3871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7056   -2.3858    0.6864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4622   -1.1128   -0.5177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4637   -0.7565    2.5382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2330    0.5995    1.3435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6021   -1.7620    2.7425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0171   -1.5624    2.4061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8463   -0.4857    1.2593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9268    3.5950   -1.0389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7972    2.2805   -1.6604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3630    2.6318   -2.5024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9557    1.2699   -0.1372 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
  4  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 16 19  2  0
 19 11  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  2 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  1
  5 28  1  0
  6 29  1  0
  6 30  1  0
  9 31  1  0
  9 32  1  0
 10 33  1  0
 10 34  1  0
 12 35  1  0
 13 36  1  0
 15 37  1  0
 18 38  1  0
 18 39  1  0
 18 40  1  0
 19 41  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -8.360   3.410   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -9.694   2.640   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -9.694   1.100   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -8.360   0.330   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -7.026   1.100   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -7.026   2.640   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0     -11.027   0.330   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      -8.360  -1.210   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -7.026  -1.980   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.693   3.410   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.359   2.640   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.025   3.410   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.692   2.640   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.358   3.410   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.976   2.640   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.309   3.410   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.643   2.640   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -3.025   4.950   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -0.358   4.950   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    7                                                  
CONECT    4    3    5    8                                                  
CONECT    5    4    6                                                       
CONECT    6    1    5   10                                                  
CONECT    7    3                                                            
CONECT    8    4    9                                                       
CONECT    9    8                                                            
CONECT   10    6   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   18                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16                                                            
CONECT   18   12                                                            
CONECT   19   14                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   38    0
END

COMPND    HMDB0302125
HETATM    1  C1  UNL     1       3.510   1.844  -1.054  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.675   0.946  -0.901  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.488  -0.507  -1.080  1.00  0.00           C  
HETATM    4  C4  UNL     1       3.576  -1.239  -0.179  1.00  0.00           C  
HETATM    5  O1  UNL     1       3.630  -2.612  -0.586  1.00  0.00           O  
HETATM    6  C5  UNL     1       2.137  -0.864  -0.359  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.267  -1.655   0.579  1.00  0.00           C  
HETATM    8  O2  UNL     1       1.723  -2.453   1.354  1.00  0.00           O  
HETATM    9  C7  UNL     1      -0.192  -1.410   0.512  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.666  -0.385   1.523  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.138  -0.260   1.324  1.00  0.00           C  
HETATM   12  C10 UNL     1      -3.003  -1.053   2.035  1.00  0.00           C  
HETATM   13  C11 UNL     1      -4.346  -0.924   1.830  1.00  0.00           C  
HETATM   14  C12 UNL     1      -4.845  -0.027   0.938  1.00  0.00           C  
HETATM   15  O3  UNL     1      -6.214   0.101   0.732  1.00  0.00           O  
HETATM   16  C13 UNL     1      -4.005   0.806   0.186  1.00  0.00           C  
HETATM   17  O4  UNL     1      -4.562   1.690  -0.700  1.00  0.00           O  
HETATM   18  C14 UNL     1      -3.845   2.569  -1.507  1.00  0.00           C  
HETATM   19  C15 UNL     1      -2.658   0.649   0.417  1.00  0.00           C  
HETATM   20  H1  UNL     1       3.064   2.162  -0.064  1.00  0.00           H  
HETATM   21  H2  UNL     1       3.933   2.843  -1.426  1.00  0.00           H  
HETATM   22  H3  UNL     1       2.774   1.580  -1.814  1.00  0.00           H  
HETATM   23  H4  UNL     1       5.453   1.265  -1.663  1.00  0.00           H  
HETATM   24  H5  UNL     1       5.175   1.184   0.075  1.00  0.00           H  
HETATM   25  H6  UNL     1       5.535  -0.957  -1.035  1.00  0.00           H  
HETATM   26  H7  UNL     1       4.201  -0.719  -2.158  1.00  0.00           H  
HETATM   27  H8  UNL     1       3.889  -1.268   0.875  1.00  0.00           H  
HETATM   28  H9  UNL     1       3.092  -2.671  -1.411  1.00  0.00           H  
HETATM   29  H10 UNL     1       1.880   0.175  -0.176  1.00  0.00           H  
HETATM   30  H11 UNL     1       1.846  -1.122  -1.387  1.00  0.00           H  
HETATM   31  H12 UNL     1      -0.706  -2.386   0.686  1.00  0.00           H  
HETATM   32  H13 UNL     1      -0.462  -1.113  -0.518  1.00  0.00           H  
HETATM   33  H14 UNL     1      -0.464  -0.757   2.538  1.00  0.00           H  
HETATM   34  H15 UNL     1      -0.233   0.600   1.343  1.00  0.00           H  
HETATM   35  H16 UNL     1      -2.602  -1.762   2.743  1.00  0.00           H  
HETATM   36  H17 UNL     1      -5.017  -1.562   2.406  1.00  0.00           H  
HETATM   37  H18 UNL     1      -6.846  -0.486   1.259  1.00  0.00           H  
HETATM   38  H19 UNL     1      -3.927   3.595  -1.039  1.00  0.00           H  
HETATM   39  H20 UNL     1      -2.797   2.281  -1.660  1.00  0.00           H  
HETATM   40  H21 UNL     1      -4.363   2.632  -2.502  1.00  0.00           H  
HETATM   41  H22 UNL     1      -1.956   1.270  -0.137  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3   23   24
CONECT    3    4   25   26
CONECT    4    5    6   27
CONECT    5   28
CONECT    6    7   29   30
CONECT    7    8    8    9
CONECT    9   10   31   32
CONECT   10   11   33   34
CONECT   11   12   12   19
CONECT   12   13   35
CONECT   13   14   14   36
CONECT   14   15   16
CONECT   15   37
CONECT   16   17   19   19
CONECT   17   18
CONECT   18   38   39   40
CONECT   19   41
END

HMDB0302125
     RDKit          3D
[4]-Gingerol
 41 41  0  0  0  0  0  0  0  0999 V2000
    3.5095    1.8441   -1.0537 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6748    0.9463   -0.9005 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4882   -0.5071   -1.0797 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5759   -1.2391   -0.1792 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6295   -2.6125   -0.5856 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1372   -0.8642   -0.3590 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2674   -1.6547    0.5790 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7225   -2.4530    1.3545 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1925   -1.4101    0.5121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6657   -0.3845    1.5229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1385   -0.2603    1.3237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0031   -1.0528    2.0350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3459   -0.9235    1.8304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8450   -0.0272    0.9376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2139    0.1011    0.7324 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0053    0.8058    0.1857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5624    1.6903   -0.7002 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8446    2.5687   -1.5073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6583    0.6494    0.4169 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0638    2.1618   -0.0643 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9332    2.8435   -1.4265 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7739    1.5796   -1.8139 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4534    1.2651   -1.6634 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1754    1.1836    0.0748 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5352   -0.9574   -1.0346 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2014   -0.7189   -2.1580 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8890   -1.2677    0.8752 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0923   -2.6708   -1.4107 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8796    0.1749   -0.1758 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8457   -1.1218   -1.3871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7056   -2.3858    0.6864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4622   -1.1128   -0.5177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4637   -0.7565    2.5382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2330    0.5995    1.3435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6021   -1.7620    2.7425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0171   -1.5624    2.4061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8463   -0.4857    1.2593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9268    3.5950   -1.0389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7972    2.2805   -1.6604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3630    2.6318   -2.5024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9557    1.2699   -0.1372 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
  4  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 16 19  2  0
 19 11  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  2 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  1
  5 28  1  0
  6 29  1  0
  6 30  1  0
  9 31  1  0
  9 32  1  0
 10 33  1  0
 10 34  1  0
 12 35  1  0
 13 36  1  0
 15 37  1  0
 18 38  1  0
 18 39  1  0
 18 40  1  0
 19 41  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₅H₂₂O₄

Average Molecular Weight

266.3328

Monoisotopic Molecular Weight

266.151809192

IUPAC Name

(5S)-5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)octan-3-one

Traditional Name

(5S)-5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)octan-3-one

CAS Registry Number

Not Available

SMILES

CCC[C@H](O)CC(=O)CCC1=CC(OC)=C(O)C=C1

InChI Identifier

InChI=1S/C15H22O4/c1-3-4-12(16)10-13(17)7-5-11-6-8-14(18)15(9-11)19-2/h6,8-9,12,16,18H,3-5,7,10H2,1-2H3/t12-/m0/s1

InChI Key

GDRKZARFCIYVCI-LBPRGKRZSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gingerols. Gingerols are compounds containing a gingerol moiety, which is structurally characterized by a 4-hydroxy-3-methoxyphenyl group substituted at the C6 carbon atom by a 5-hydroxy-alkane-3-one.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Gingerol
Fatty alcohol
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Monocyclic benzene moiety
Beta-hydroxy ketone
Fatty acyl
Ketone
Secondary alcohol
Ether
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organic oxygen compound
Alcohol
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Ginger (FooDB: FOOD00206)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	2.51	ALOGPS
logP	2.73	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	9.95	ChemAxon
pKa (Strongest Basic)	-2.8	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	8	ChemAxon
Refractivity	73.91 m³·mol⁻¹	ChemAxon
Polarizability	29.7 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
AllCCS	[M+H]+	166.356	32859911
AllCCS	[M+H-H2O]+	162.861	32859911
AllCCS	[M+Na]+	170.532	32859911
AllCCS	[M+NH4]+	169.599	32859911
AllCCS	[M-H]-	167.8	32859911
AllCCS	[M+Na-2H]-	168.441	32859911
AllCCS	[M+HCOO]-	169.274	32859911
DeepCCS	[M+H]+	169.012	30932474
DeepCCS	[M-H]-	166.654	30932474
DeepCCS	[M-2H]-	199.54	30932474
DeepCCS	[M+Na]+	175.105	30932474

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
[4]-Gingerol,3TMS,isomer #1	CCC[C@@H](CC(=CCC1=CC=C(O[Si](C)(C)C)C(OC)=C1)O[Si](C)(C)C)O[Si](C)(C)C	2436.0	Semi standard non polar	33892256
[4]-Gingerol,3TMS,isomer #1	CCC[C@@H](CC(=CCC1=CC=C(O[Si](C)(C)C)C(OC)=C1)O[Si](C)(C)C)O[Si](C)(C)C	2326.1	Standard non polar	33892256
[4]-Gingerol,3TMS,isomer #1	CCC[C@@H](CC(=CCC1=CC=C(O[Si](C)(C)C)C(OC)=C1)O[Si](C)(C)C)O[Si](C)(C)C	2492.3	Standard polar	33892256
[4]-Gingerol,3TMS,isomer #2	CCC[C@@H](C=C(CCC1=CC=C(O[Si](C)(C)C)C(OC)=C1)O[Si](C)(C)C)O[Si](C)(C)C	2337.2	Semi standard non polar	33892256
[4]-Gingerol,3TMS,isomer #2	CCC[C@@H](C=C(CCC1=CC=C(O[Si](C)(C)C)C(OC)=C1)O[Si](C)(C)C)O[Si](C)(C)C	2263.6	Standard non polar	33892256
[4]-Gingerol,3TMS,isomer #2	CCC[C@@H](C=C(CCC1=CC=C(O[Si](C)(C)C)C(OC)=C1)O[Si](C)(C)C)O[Si](C)(C)C	2431.0	Standard polar	33892256
[4]-Gingerol,3TBDMS,isomer #1	CCC[C@@H](CC(=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	3101.8	Semi standard non polar	33892256
[4]-Gingerol,3TBDMS,isomer #1	CCC[C@@H](CC(=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	2919.9	Standard non polar	33892256
[4]-Gingerol,3TBDMS,isomer #1	CCC[C@@H](CC(=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	2807.9	Standard polar	33892256
[4]-Gingerol,3TBDMS,isomer #2	CCC[C@@H](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	3023.4	Semi standard non polar	33892256
[4]-Gingerol,3TBDMS,isomer #2	CCC[C@@H](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	2831.7	Standard non polar	33892256
[4]-Gingerol,3TBDMS,isomer #2	CCC[C@@H](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	2749.4	Standard polar	33892256

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - [4]-Gingerol 10V, Positive-QTOF	splash10-00kb-1190000000-c77a848de4b3e6a69bbb	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - [4]-Gingerol 20V, Positive-QTOF	splash10-004s-5930000000-700f3a1961754e5593eb	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - [4]-Gingerol 40V, Positive-QTOF	splash10-0f76-9600000000-f3cff2443dd47d66c5a5	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - [4]-Gingerol 10V, Negative-QTOF	splash10-014i-1290000000-8d454e31e1b64f5a7d16	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - [4]-Gingerol 20V, Negative-QTOF	splash10-00mo-5940000000-c4e5d8e529314743e510	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - [4]-Gingerol 40V, Negative-QTOF	splash10-0a6u-7900000000-765fe21b082777199ade	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - [4]-Gingerol 10V, Positive-QTOF	splash10-001s-0390000000-903cc42bc2e5e34486e9	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - [4]-Gingerol 20V, Positive-QTOF	splash10-053j-2950000000-f152bc87b7ce20455d67	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - [4]-Gingerol 40V, Positive-QTOF	splash10-05g0-3900000000-7fc107bb4400f4637845	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - [4]-Gingerol 10V, Negative-QTOF	splash10-014i-2490000000-13aa6767638620580fc3	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - [4]-Gingerol 20V, Negative-QTOF	splash10-08g4-4930000000-a309a6f7f05c4b79bac4	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - [4]-Gingerol 40V, Negative-QTOF	splash10-0abl-8900000000-9015ee81f0f8ed6cf35d	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

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

FDB001886

KNApSAcK ID

Not Available

Chemspider ID

59696289

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

46901319

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

Not Available

Showing metabocard for [4]-Gingerol (HMDB0302125)

MOL for HMDB0302125 ([4]-Gingerol)

3D MOL for HMDB0302125 ([4]-Gingerol)

3D SDF for HMDB0302125 ([4]-Gingerol)

3D-SDF for HMDB0302125 ([4]-Gingerol)

PDB for HMDB0302125 ([4]-Gingerol)

3D PDB for HMDB0302125 ([4]-Gingerol)

SMILES for HMDB0302125 ([4]-Gingerol)

INCHI for HMDB0302125 ([4]-Gingerol)

Structure for HMDB0302125 ([4]-Gingerol)

3D Structure for HMDB0302125 ([4]-Gingerol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

MS/MS Spectra