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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:43:29 UTC
Update Date2019-07-23 06:08:49 UTC
HMDB IDHMDB0031462
Secondary Accession Numbers
  • HMDB31462
Metabolite Identification
Common Name[10]-Shogaol
Description[10]-Shogaol belongs to the class of organic compounds known as shogaols. These are ginger derivatives containing a shogaol moiety, which consists of a benzene ring bearing a dec-4-en-3-one moiety, a methoxyphenyl group, a hydroxyl group and at positions 1, 3, and 4, respectively. [10]-Shogaol is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, [10]-shogaol has been detected, but not quantified in, gingers. This could make [10]-shogaol a potential biomarker for the consumption of these foods.
Structure
Data?1563862129
Synonyms
ValueSource
10-ShogaolHMDB
1-(4-Hydroxy-3-methoxyphenyl)-4-tetradecen-3-oneHMDB
(10)-ShogaolMeSH
Chemical FormulaC21H32O3
Average Molecular Weight332.477
Monoisotopic Molecular Weight332.23514489
IUPAC Name(4E)-1-(4-hydroxy-3-methoxyphenyl)tetradec-4-en-3-one
Traditional Name(4E)-1-(4-hydroxy-3-methoxyphenyl)tetradec-4-en-3-one
CAS Registry Number36752-54-2
SMILES
CCCCCCCCC\C=C\C(=O)CCC1=CC(OC)=C(O)C=C1
InChI Identifier
InChI=1S/C21H32O3/c1-3-4-5-6-7-8-9-10-11-12-19(22)15-13-18-14-16-20(23)21(17-18)24-2/h11-12,14,16-17,23H,3-10,13,15H2,1-2H3/b12-11+
InChI KeyFADFGCOCHHNRHF-VAWYXSNFSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as shogaols. These are ginger derivatives containing a shogaol moiety, which consists of a benzene ring bearing a dec-4-en-3-one moiety, a methoxyphenyl group, a hydroxyl group and at positions 1, 3, and 4, respectively.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassMethoxyphenols
Direct ParentShogaols
Alternative Parents
Substituents
  • Shogaol
  • Phenoxy compound
  • Anisole
  • Phenol ether
  • Methoxybenzene
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Enone
  • Acryloyl-group
  • Alpha,beta-unsaturated ketone
  • Ketone
  • Ether
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Organic oxide
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00059 g/LALOGPS
logP6.67ALOGPS
logP6.62ChemAxon
logS-5.8ALOGPS
pKa (Strongest Acidic)9.95ChemAxon
pKa (Strongest Basic)-4.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity101.09 m³·mol⁻¹ChemAxon
Polarizability40.6 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-003i-9741000000-5c09cfb9fce0b91beea8Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-059l-9227000000-0762cda5a71cec833b39Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-000i-0900000000-c6c789c80c998c103069Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-000i-0900000000-3fade94d291eb5f1df99Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0209000000-ae770316cbcb3e8bcdc5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f80-2912000000-55363bb62eceba114bb2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0k9f-9800000000-1af91dbf54b93e916c83Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0209000000-36b605227b6390861cfcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0906000000-81662b4141472b3b050aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-1910000000-d8aaa5082d8a8bfc5db1Spectrum
Biological Properties
Cellular Locations
  • Membrane
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 IDFDB007721
KNApSAcK IDC00034994
Chemspider ID4946680
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6442612
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 References
  1. (). Duke, James A. (1992) Handbook of phytochemical constituents of GRAS herbs and other economic plants. Boca Raton, FL. CRC Press.. .