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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2007-01-22 09:25:58 UTC
Update Date2019-07-23 05:47:00 UTC
HMDB IDHMDB0005783
Secondary Accession Numbers
  • HMDB05783
Metabolite Identification
Common NameGingerol
DescriptionGingerol, 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. When ginger is dried or mildly heated, gingerol undergoes a dehydration reaction forming shogaols, which are about twice as pungent as gingerol. Gingerol is an extremely weak basic (essentially neutral) compound (based on its pKa). Gingerol is a pungent. Outside of the human body, gingerol is found, on average, in the highest concentration in gingers. gingerol has also been detected, but not quantified in, several different foods, such as pepper (spice), cumins, sweet bay, nutmegs, and caraway. This could make gingerol a potential biomarker for the consumption of these foods. While the biosynthesis of 6-gingerol is not fully elucidated, plausible pathways are presented here. It is speculated that some polyketide synthases (PKS) and reductases are involved in final synthesis of 6-Gingerol (10). 4-coumarate:CoA ligase (4CL) is then used to get p-Coumaroyl-CoA (5).
Structure
Data?1563860820
Synonyms
ValueSource
6g [6]-GingerolHMDB
5-Hydroxy-1-(4-hydroxy-3-methoxtphenyl)-3-decanoneHMDB
5-Hydroxy-1-(4-hydroxy-3-methoxycyclohexyl)decan-3-oneHMDB
6-GingerolHMDB
[6]-GingerolHMDB
(6)-GingerolHMDB
10-GingerolHMDB
Chemical FormulaC17H26O4
Average Molecular Weight294.3859
Monoisotopic Molecular Weight294.18310932
IUPAC Name5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)decan-3-one
Traditional Namegingerol
CAS Registry Number58253-27-3
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 KeyNLDDIKRKFXEWBK-UHFFFAOYSA-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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassMethoxyphenols
Direct ParentGingerols
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 FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point30 - 32 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.08 g/LALOGPS
logP3.45ALOGPS
logP3.62ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)9.95ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity83.11 m³·mol⁻¹ChemAxon
Polarizability33.76 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000i-3910000000-3c07be71d662410144abJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000i-3910000000-3c07be71d662410144abJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-6900000000-9e3ae5652d5b17b9016dJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00di-7119300000-fbff188e294cacd919c6JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-004i-0920000000-010ef6242d9f56fa2a72JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-0900000000-36e283e52cb0ba857d0eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-0900000000-35209ecc08a0fcbe3338JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-1900000000-aefaf0623f9721907b4dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00du-6900000000-50259fc38798f2830932JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004j-0290000000-da571dea1713ff08f13bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-4930000000-922f5386fa26a96a1bbcJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9400000000-e27c462b7ff389743a4cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0290000000-d356007500cff17f32acJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002f-3930000000-be6a576d74a0f97fb8fcJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6r-5900000000-31f35b868a26cada9bf5JSpectraViewer
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB001108
KNApSAcK IDC00002748
Chemspider ID3354
KEGG Compound IDC10462
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkGingerol
METLIN IDNot Available
PubChem Compound3473
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available