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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-12 02:55:15 UTC
Update Date2019-07-23 06:34:02 UTC
HMDB IDHMDB0041249
Secondary Accession Numbers
  • HMDB41249
Metabolite Identification
Common Name6-Hydroxyshogaol
Description6-Hydroxyshogaol 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. 6-Hydroxyshogaol is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 6-Hydroxyshogaol has been detected, but not quantified in, herbs and spices. This could make 6-hydroxyshogaol a potential biomarker for the consumption of these foods.
Structure
Data?1563863642
Synonyms
ValueSource
6-Hydroxy-1-(4-hydroxy-3-methoxyphenyl)-4-decen-3-oneHMDB
Chemical FormulaC17H24O4
Average Molecular Weight292.3701
Monoisotopic Molecular Weight292.167459256
IUPAC Name(4E)-6-hydroxy-1-(4-hydroxy-3-methoxyphenyl)dec-4-en-3-one
Traditional Name(4E)-6-hydroxy-1-(4-hydroxy-3-methoxyphenyl)dec-4-en-3-one
CAS Registry Number143114-93-6
SMILES
CCCCC(O)\C=C\C(=O)CCC1=CC(OC)=C(O)C=C1
InChI Identifier
InChI=1S/C17H24O4/c1-3-4-5-14(18)9-10-15(19)8-6-13-7-11-16(20)17(12-13)21-2/h7,9-12,14,18,20H,3-6,8H2,1-2H3/b10-9+
InChI KeySEWFXECKZBLANJ-MDZDMXLPSA-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
  • Fatty alcohol
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Fatty acyl
  • Enone
  • Acryloyl-group
  • Alpha,beta-unsaturated ketone
  • Ketone
  • Secondary alcohol
  • Ether
  • Alcohol
  • Organooxygen compound
  • Hydrocarbon derivative
  • 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:

Role

Biological role:

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 Solubility0.098 g/LALOGPS
logP3.18ALOGPS
logP3.61ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)9.95ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity84.2 m³·mol⁻¹ChemAxon
Polarizability33.68 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4l-9650000000-e9a92ffdb0520a57df20Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00di-9484700000-13b49ab356704bb7e710Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004l-0190000000-e5166111300a8cdb74caSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-054x-5950000000-7b2ff27efe4c4521e7ceSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0k9f-9410000000-2169845180ebf09200c0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0090000000-0d597d8cf9882c53e0c7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-2980000000-db88137d4e80a4c6b9feSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udr-5910000000-633749554bf92a2b71e7Spectrum
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
FooDB IDFDB021157
KNApSAcK IDNot Available
Chemspider ID9315994
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11140882
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. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .