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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2007-01-22 09:25:58 UTC
Update Date2022-03-07 02:49:28 UTC
HMDB IDHMDB0005783
Secondary Accession Numbers
  • HMDB05783
Metabolite Identification
Common NameGingerol
DescriptionGingerol 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 a pungent tasting compound. Gingerol is found, on average, in the highest concentration within gingers (Zingiber officinale). Gingerol has also been detected, but not quantified in, several different foods, such as sweet bays (Laurus nobilis), star anises (Illicium verum), ceylon cinnamons (Cinnamomum verum), nutmegs (Myristica fragrans), and caraways (Carum carvi). This could make gingerol a potential biomarker for the consumption of these foods. Gingerol is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on Gingerol.
Structure
Data?1582752364
Synonyms
ValueSource
6g [6]-GingerolChEMBL, HMDB
5-Hydroxy-1-(4-hydroxy-3-methoxtphenyl)-3-decanoneHMDB
5-Hydroxy-1-(4-hydroxy-3-methoxycyclohexyl)decan-3-oneHMDB
6-GingerolHMDB
[6]-GingerolHMDB
(6)-GingerolMeSH, HMDB
10-GingerolMeSH, HMDB
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

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point30 - 32 °CNot Available
Boiling Point567.00 to 568.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility97.87 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP6.670 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+173.30431661259
DarkChem[M-H]-176.38431661259
DeepCCS[M+H]+177.94330932474
DeepCCS[M-H]-175.58530932474
DeepCCS[M-2H]-208.47130932474
DeepCCS[M+Na]+184.03630932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
GingerolCCCCCC(O)CC(=O)CCC1=CC=C(O)C(OC)=C13996.1Standard polar33892256
GingerolCCCCCC(O)CC(=O)CCC1=CC=C(O)C(OC)=C12339.3Standard non polar33892256
GingerolCCCCCC(O)CC(=O)CCC1=CC=C(O)C(OC)=C12404.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Gingerol,1TMS,isomer #1CCCCCC(CC(=O)CCC1=CC=C(O)C(OC)=C1)O[Si](C)(C)C2383.0Semi standard non polar33892256
Gingerol,1TMS,isomer #2CCCCCC(O)CC(=O)CCC1=CC=C(O[Si](C)(C)C)C(OC)=C12477.3Semi standard non polar33892256
Gingerol,1TMS,isomer #3CCCCCC(O)CC(=CCC1=CC=C(O)C(OC)=C1)O[Si](C)(C)C2564.8Semi standard non polar33892256
Gingerol,1TMS,isomer #4CCCCCC(O)C=C(CCC1=CC=C(O)C(OC)=C1)O[Si](C)(C)C2507.7Semi standard non polar33892256
Gingerol,2TMS,isomer #1CCCCCC(CC(=O)CCC1=CC=C(O[Si](C)(C)C)C(OC)=C1)O[Si](C)(C)C2416.1Semi standard non polar33892256
Gingerol,2TMS,isomer #2CCCCCC(CC(=CCC1=CC=C(O)C(OC)=C1)O[Si](C)(C)C)O[Si](C)(C)C2546.5Semi standard non polar33892256
Gingerol,2TMS,isomer #3CCCCCC(C=C(CCC1=CC=C(O)C(OC)=C1)O[Si](C)(C)C)O[Si](C)(C)C2493.6Semi standard non polar33892256
Gingerol,2TMS,isomer #4CCCCCC(O)CC(=CCC1=CC=C(O[Si](C)(C)C)C(OC)=C1)O[Si](C)(C)C2596.1Semi standard non polar33892256
Gingerol,2TMS,isomer #5CCCCCC(O)C=C(CCC1=CC=C(O[Si](C)(C)C)C(OC)=C1)O[Si](C)(C)C2514.5Semi standard non polar33892256
Gingerol,3TMS,isomer #1CCCCCC(CC(=CCC1=CC=C(O[Si](C)(C)C)C(OC)=C1)O[Si](C)(C)C)O[Si](C)(C)C2577.7Semi standard non polar33892256
Gingerol,3TMS,isomer #1CCCCCC(CC(=CCC1=CC=C(O[Si](C)(C)C)C(OC)=C1)O[Si](C)(C)C)O[Si](C)(C)C2488.1Standard non polar33892256
Gingerol,3TMS,isomer #1CCCCCC(CC(=CCC1=CC=C(O[Si](C)(C)C)C(OC)=C1)O[Si](C)(C)C)O[Si](C)(C)C2681.0Standard polar33892256
Gingerol,3TMS,isomer #2CCCCCC(C=C(CCC1=CC=C(O[Si](C)(C)C)C(OC)=C1)O[Si](C)(C)C)O[Si](C)(C)C2499.0Semi standard non polar33892256
Gingerol,3TMS,isomer #2CCCCCC(C=C(CCC1=CC=C(O[Si](C)(C)C)C(OC)=C1)O[Si](C)(C)C)O[Si](C)(C)C2432.5Standard non polar33892256
Gingerol,3TMS,isomer #2CCCCCC(C=C(CCC1=CC=C(O[Si](C)(C)C)C(OC)=C1)O[Si](C)(C)C)O[Si](C)(C)C2612.6Standard polar33892256
Gingerol,1TBDMS,isomer #1CCCCCC(CC(=O)CCC1=CC=C(O)C(OC)=C1)O[Si](C)(C)C(C)(C)C2628.3Semi standard non polar33892256
Gingerol,1TBDMS,isomer #2CCCCCC(O)CC(=O)CCC1=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C12711.4Semi standard non polar33892256
Gingerol,1TBDMS,isomer #3CCCCCC(O)CC(=CCC1=CC=C(O)C(OC)=C1)O[Si](C)(C)C(C)(C)C2796.5Semi standard non polar33892256
Gingerol,1TBDMS,isomer #4CCCCCC(O)C=C(CCC1=CC=C(O)C(OC)=C1)O[Si](C)(C)C(C)(C)C2751.8Semi standard non polar33892256
Gingerol,2TBDMS,isomer #1CCCCCC(CC(=O)CCC1=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C1)O[Si](C)(C)C(C)(C)C2881.6Semi standard non polar33892256
Gingerol,2TBDMS,isomer #2CCCCCC(CC(=CCC1=CC=C(O)C(OC)=C1)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2998.2Semi standard non polar33892256
Gingerol,2TBDMS,isomer #3CCCCCC(C=C(CCC1=CC=C(O)C(OC)=C1)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2964.6Semi standard non polar33892256
Gingerol,2TBDMS,isomer #4CCCCCC(O)CC(=CCC1=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C1)O[Si](C)(C)C(C)(C)C3059.1Semi standard non polar33892256
Gingerol,2TBDMS,isomer #5CCCCCC(O)C=C(CCC1=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C1)O[Si](C)(C)C(C)(C)C2986.4Semi standard non polar33892256
Gingerol,3TBDMS,isomer #1CCCCCC(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)C3254.9Semi standard non polar33892256
Gingerol,3TBDMS,isomer #1CCCCCC(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)C3049.6Standard non polar33892256
Gingerol,3TBDMS,isomer #1CCCCCC(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)C2960.5Standard polar33892256
Gingerol,3TBDMS,isomer #2CCCCCC(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)C3193.7Semi standard non polar33892256
Gingerol,3TBDMS,isomer #2CCCCCC(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)C2978.8Standard non polar33892256
Gingerol,3TBDMS,isomer #2CCCCCC(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)C2897.5Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Gingerol EI-B (Non-derivatized)splash10-000i-3910000000-3c07be71d662410144ab2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Gingerol EI-B (Non-derivatized)splash10-000i-3910000000-3c07be71d662410144ab2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Gingerol GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-6900000000-9e3ae5652d5b17b9016d2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Gingerol GC-MS (2 TMS) - 70eV, Positivesplash10-00di-7119300000-fbff188e294cacd919c62017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Gingerol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Gingerol LC-ESI-QTOF , positive-QTOFsplash10-004i-0920000000-010ef6242d9f56fa2a722017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Gingerol LC-ESI-QTOF , positive-QTOFsplash10-000i-0900000000-36e283e52cb0ba857d0e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Gingerol LC-ESI-QTOF , positive-QTOFsplash10-000i-0900000000-35209ecc08a0fcbe33382017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Gingerol LC-ESI-QTOF , positive-QTOFsplash10-000i-1900000000-aefaf0623f9721907b4d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Gingerol LC-ESI-QTOF , positive-QTOFsplash10-00du-6900000000-50259fc38798f28309322017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Gingerol 30V, Positive-QTOFsplash10-000i-0900000000-35209ecc08a0fcbe33382021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Gingerol 40V, Positive-QTOFsplash10-000i-1900000000-aefaf0623f9721907b4d2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Gingerol 20V, Positive-QTOFsplash10-000i-0900000000-36e283e52cb0ba857d0e2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Gingerol 10V, Positive-QTOFsplash10-004i-0920000000-010ef6242d9f56fa2a722021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Gingerol 50V, Positive-QTOFsplash10-00du-6900000000-50259fc38798f28309322021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gingerol 10V, Positive-QTOFsplash10-004j-0290000000-da571dea1713ff08f13b2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gingerol 20V, Positive-QTOFsplash10-004i-4930000000-922f5386fa26a96a1bbc2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gingerol 40V, Positive-QTOFsplash10-0a4l-9400000000-e27c462b7ff389743a4c2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gingerol 10V, Negative-QTOFsplash10-0006-0290000000-d356007500cff17f32ac2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gingerol 20V, Negative-QTOFsplash10-002f-3930000000-be6a576d74a0f97fb8fc2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gingerol 40V, Negative-QTOFsplash10-0a6r-5900000000-31f35b868a26cada9bf52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gingerol 10V, Positive-QTOFsplash10-0551-0590000000-d52178d2e2ff78317f7b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gingerol 20V, Positive-QTOFsplash10-052k-2940000000-060d47dec6b201c1d70d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gingerol 40V, Positive-QTOFsplash10-000i-3900000000-2ea673e61b75d0b2bbe92021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gingerol 10V, Negative-QTOFsplash10-0a4l-4590000000-b65edb04dc7fdd19e6e32021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gingerol 20V, Negative-QTOFsplash10-0a4i-6890000000-9e209efe1855c3c2ace72021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gingerol 40V, Negative-QTOFsplash10-0a4r-9700000000-cd27d9c02d1d0d56a9542021-09-23Wishart LabView Spectrum
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
FooDB 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
MarkerDB IDNot Available
Good Scents IDrw1384631
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available