NP-MRD: Showing NP-Card for gingerol (NP0183895)

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Record Information

Version

2.0

Created at

2022-09-03 22:53:15 UTC

Updated at

2022-09-03 22:53:15 UTC

NP-MRD ID

NP0183895

Secondary Accession Numbers

None

Natural Product Identification

Common Name

gingerol

Description

Gingerol, also known as 6G [6]-gingerol or (6)-gingerol, 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. Gingerol is an extremely weak basic (essentially neutral) compound (based on its pKa). Gingerol is a pungent tasting compound. Outside of the human body, Gingerol is found, on average, in the highest concentration within gingers. Gingerol has also been detected, but not quantified in, several different foods, such as herbs and spices, nutmegs, cumins, cloves, and pepper (spice). This could make gingerol a potential biomarker for the consumption of these foods. It is normally found as a pungent yellow oil, but also can form a low-melting crystalline solid. Gingerol, a plant polyphenol, is the active constituent of fresh ginger. gingerol is found in Aframomum melegueta and Zingiber officinale. Chemically, gingerol is a relative of capsaicin, the compound that gives chile peppers their spiciness.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 47 47  0  0  0  0  0  0  0  0999 V2000
   -7.3549    0.5692    0.9540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8487    0.6683    0.7401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1677    0.3065    2.0071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6865    0.3432    2.0131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0789    1.6654    1.7068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5742    1.6115    1.7400 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1766    1.2157    3.0372 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9834    0.6236    0.7891 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5024    0.6644    0.9181 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0194    1.4202    1.7081 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3706   -0.2217    0.0820 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8409    0.0014    0.4377 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7100   -0.8768   -0.3822 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0948   -2.1393   -0.0207 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8892   -2.9512   -0.7673 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3556   -2.4895   -1.9874 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1728   -3.2911   -2.7855 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9897   -1.2044   -2.4006 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4786   -0.7987   -3.6129 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2733    0.4193   -4.2552 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1881   -0.4187   -1.6190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7286   -0.3799    0.5131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8898    1.4543    0.5672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5641    0.5276    2.0413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5874   -0.0156   -0.0942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6464    1.6963    0.3876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4968   -0.7363    2.2732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5939    0.9427    2.8355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2796   -0.4693    1.3558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3629    0.0462    3.0511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4192    2.0394    0.7170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3783    2.3716    2.5340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1242    2.6049    1.5678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9257    1.3765    3.6549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2790    0.7935   -0.2671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2631   -0.4121    1.1429 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2226   -0.0284   -0.9875 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1191   -1.2668    0.3441 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0157   -0.2962    1.4993 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0844    1.0699    0.2769 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7073   -2.4776    0.9537 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1346   -3.9242   -0.3944 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4876   -2.9045   -3.6690 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9656    1.1818   -3.7992 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6125    0.3070   -5.3182 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2616    0.8238   -4.1549 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9133    0.5580   -1.9368 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  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
  5 32  1  0
  6 33  1  6
  7 34  1  0
  8 35  1  0
  8 36  1  0
 11 37  1  0
 11 38  1  0
 12 39  1  0
 12 40  1  0
 14 41  1  0
 15 42  1  0
 17 43  1  0
 20 44  1  0
 20 45  1  0
 20 46  1  0
 21 47  1  0
M  END


  Mrv0541 02231220292D          

 21 21  0  0  0  0            999 V2000
   15.0982  -18.0898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5107  -17.3752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3356  -17.3752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7481  -16.6607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5731  -16.6607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9855  -15.9461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5731  -15.2316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9855  -14.5170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8104  -14.5170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.5731  -13.8031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7481  -13.8031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3356  -13.0885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7481  -12.3740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3356  -11.6595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5107  -11.6595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0982  -12.3740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5107  -13.0885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2733  -12.3740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8608  -13.0885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0982  -10.9449    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.8104  -15.9461    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6 21  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 17  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 20  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0183895

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C17H26O4/c1-3-4-5-6-14(18)12-15(19)9-7-13-8-10-16(20)17(11-13)21-2/h8,10-11,14,18,20H,3-7,9,12H2,1-2H3

> <INCHI_KEY>
NLDDIKRKFXEWBK-UHFFFAOYSA-N

> <FORMULA>
C17H26O4

> <MOLECULAR_WEIGHT>
294.3859

> <EXACT_MASS>
294.18310932

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
33.75644949558624

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.45

> <JCHEM_LOGP>
3.6165198106666674

> <ALOGPS_LOGS>
-3.57

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.081610040240694

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.945873119687446

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7614721709918255

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
83.10920000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.96e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
gingerol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      28.183 -33.768   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      28.953 -32.434   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      30.493 -32.434   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      31.263 -31.100   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      32.803 -31.100   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      33.573 -29.766   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      32.803 -28.432   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      33.573 -27.098   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      35.113 -27.098   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      32.803 -25.766   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      31.263 -25.766   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      30.493 -24.432   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      31.263 -23.098   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      30.493 -21.764   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      28.953 -21.764   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      28.183 -23.098   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      28.953 -24.432   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      26.643 -23.098   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      25.873 -24.432   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      28.183 -20.430   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      35.113 -29.766   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   21                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   20                                                  
CONECT   16   15   17   18                                                  
CONECT   17   12   16                                                       
CONECT   18   16   19                                                       
CONECT   19   18                                                            
CONECT   20   15                                                            
CONECT   21    6                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   42    0
END

View in JSmol

Synonyms

Value	Source
6g [6]-Gingerol	HMDB
5-Hydroxy-1-(4-hydroxy-3-methoxtphenyl)-3-decanone	HMDB
5-Hydroxy-1-(4-hydroxy-3-methoxycyclohexyl)decan-3-one	HMDB
6-Gingerol	HMDB
[6]-Gingerol	HMDB
(6)-Gingerol	HMDB
10-Gingerol	HMDB

Chemical Formula

C₁₇H₂₆O₄

Average Mass

294.3859 Da

Monoisotopic Mass

294.18311 Da

IUPAC Name

5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)decan-3-one

Traditional Name

gingerol

CAS Registry Number

Not Available

SMILES

CCCCCC(O)CC(=O)CCC1=CC=C(O)C(OC)=C1

InChI Identifier

InChI=1S/C17H26O4/c1-3-4-5-6-14(18)12-15(19)9-7-13-8-10-16(20)17(11-13)21-2/h8,10-11,14,18,20H,3-7,9,12H2,1-2H3

InChI Key

NLDDIKRKFXEWBK-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Aframomum melegueta	LOTUS Database	35616633
Zingiber officinale	LOTUS Database	35616633

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

a phenylpropanoid (CPD-13494 )

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source
logP	3.45	ALOGPS
logP	3.62	ChemAxon
logS	-3.6	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	10	ChemAxon
Refractivity	83.11 m³·mol⁻¹	ChemAxon
Polarizability	33.76 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