Record Information
Version1.0
Creation date2010-04-08 22:07:46 UTC
Update date2018-01-25 19:38:39 UTC
Primary IDFDB007785
Secondary Accession NumbersNot Available
Chemical Information
FooDB Namecis-[10]-Shogaol
Description[10]-shogaol, also known as 1-(4-hydroxy-3-methoxyphenyl)-4-tetradecen-3-one, is a member of the class of compounds known as shogaols. Shogaols 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 practically insoluble (in water) and a very weakly acidic compound (based on its pKa). [10]-shogaol can be found in ginger, which makes [10]-shogaol a potential biomarker for the consumption of this food product.
CAS NumberNot Available
Structure
Thumb
Synonyms
SynonymSource
10-ShogaolHMDB
1-(4-Hydroxy-3-methoxyphenyl)-4-tetradecen-3-oneHMDB
(10)-ShogaolMeSH
CIS-10-SHOGAOLmanual
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
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC21H32O3
IUPAC name(4E)-1-(4-hydroxy-3-methoxyphenyl)tetradec-4-en-3-one
InChI IdentifierInChI=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
Isomeric SMILESCCCCCCCCC\C=C\C(=O)CCC1=CC(OC)=C(O)C=C1
Average Molecular Weight332.477
Monoisotopic Molecular Weight332.23514489
Classification
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
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-003i-9741000000-5c09cfb9fce0b91beea8View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-059l-9227000000-0762cda5a71cec833b39View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-000i-0900000000-c6c789c80c998c103069View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-000i-0900000000-3fade94d291eb5f1df99View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0209000000-ae770316cbcb3e8bcdc5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f80-2912000000-55363bb62eceba114bb2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0k9f-9800000000-1af91dbf54b93e916c83View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0209000000-36b605227b6390861cfcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0906000000-81662b4141472b3b050aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-1910000000-d8aaa5082d8a8bfc5db1View in MoNA
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDHBF68-C:OPV27-K
EAFUS IDNot Available
Dr. Duke IDCIS-10-SHOGAOL
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).