Hmdb loader
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:43:29 UTC
Update Date2022-03-07 02:52:59 UTC
HMDB IDHMDB0031463
Secondary Accession Numbers
  • HMDB31463
Metabolite Identification
Common Name[8]-Shogaol
Description[8]-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. [8]-Shogaol is found, on average, in the highest concentration within gingers (Zingiber officinale). [8]-Shogaol has also been detected, but not quantified in, alcoholic beverages and herbs and spices. This could make [8]-shogaol a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on [8]-Shogaol.
Structure
Data?1563862129
Synonyms
ValueSource
1-(4-Hydroxy-3-methoxyphenyl)-4-dodecen-3-one, 9ciHMDB
Chemical FormulaC17H24O3
Average Molecular Weight276.3707
Monoisotopic Molecular Weight276.172544634
IUPAC Name1-(4-hydroxy-3-methoxyphenyl)dec-4-en-3-one
Traditional Nameshogaol
CAS Registry Number36700-45-5
SMILES
CCCCCC=CC(=O)CCC1=CC(OC)=C(O)C=C1
InChI Identifier
InChI=1S/C17H24O3/c1-3-4-5-6-7-8-15(18)11-9-14-10-12-16(19)17(13-14)20-2/h7-8,10,12-13,19H,3-6,9,11H2,1-2H3
InChI KeyOQWKEEOHDMUXEO-UHFFFAOYSA-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 Descriptors
Ontology
Disposition

Source

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.34 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0089 g/LALOGPS
logP4.95ALOGPS
logP4.85ChemAxon
logS-4.5ALOGPS
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 Count9ChemAxon
Refractivity82.69 m³·mol⁻¹ChemAxon
Polarizability32.26 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]+170.56331661259
DarkChem[M-H]-173.30731661259
DeepCCS[M+H]+173.29330932474
DeepCCS[M-H]-170.93530932474
DeepCCS[M-2H]-203.82130932474
DeepCCS[M+Na]+179.38730932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
[8]-ShogaolCCCCCC=CC(=O)CCC1=CC(OC)=C(O)C=C13883.3Standard polar33892256
[8]-ShogaolCCCCCC=CC(=O)CCC1=CC(OC)=C(O)C=C12246.3Standard non polar33892256
[8]-ShogaolCCCCCC=CC(=O)CCC1=CC(OC)=C(O)C=C12273.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
[8]-Shogaol,1TMS,isomer #1CCCCCC=CC(=O)CCC1=CC=C(O[Si](C)(C)C)C(OC)=C12358.3Semi standard non polar33892256
[8]-Shogaol,1TMS,isomer #2CCCCCC=CC(=CCC1=CC=C(O)C(OC)=C1)O[Si](C)(C)C2523.2Semi standard non polar33892256
[8]-Shogaol,2TMS,isomer #1CCCCCC=CC(=CCC1=CC=C(O[Si](C)(C)C)C(OC)=C1)O[Si](C)(C)C2537.9Semi standard non polar33892256
[8]-Shogaol,2TMS,isomer #1CCCCCC=CC(=CCC1=CC=C(O[Si](C)(C)C)C(OC)=C1)O[Si](C)(C)C2375.2Standard non polar33892256
[8]-Shogaol,1TBDMS,isomer #1CCCCCC=CC(=O)CCC1=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C12612.4Semi standard non polar33892256
[8]-Shogaol,1TBDMS,isomer #2CCCCCC=CC(=CCC1=CC=C(O)C(OC)=C1)O[Si](C)(C)C(C)(C)C2772.7Semi standard non polar33892256
[8]-Shogaol,2TBDMS,isomer #1CCCCCC=CC(=CCC1=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C1)O[Si](C)(C)C(C)(C)C3030.0Semi standard non polar33892256
[8]-Shogaol,2TBDMS,isomer #1CCCCCC=CC(=CCC1=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C1)O[Si](C)(C)C(C)(C)C2820.7Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - [8]-Shogaol GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-9620000000-f02bcd9c6283a8cf88fc2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - [8]-Shogaol GC-MS (1 TMS) - 70eV, Positivesplash10-05iu-9154000000-46bfcab1accb3045874c2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - [8]-Shogaol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - [8]-Shogaol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - [8]-Shogaol 10V, Positive-QTOFsplash10-004i-1190000000-06bc9c8afe1085ba26322016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - [8]-Shogaol 20V, Positive-QTOFsplash10-005i-8950000000-03ec6db458ca2af67e592016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - [8]-Shogaol 40V, Positive-QTOFsplash10-0k96-9510000000-caea94c9bbdf4f66b2e62016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - [8]-Shogaol 10V, Negative-QTOFsplash10-004i-0190000000-6ef295bdbca7cf3546e12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - [8]-Shogaol 20V, Negative-QTOFsplash10-004i-2890000000-eebd2ec4aab29e15a6d32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - [8]-Shogaol 40V, Negative-QTOFsplash10-000i-4910000000-cd83ea72d889effd18472016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - [8]-Shogaol 10V, Negative-QTOFsplash10-004i-0190000000-04e9fac4b2d89f8de33c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - [8]-Shogaol 20V, Negative-QTOFsplash10-0079-0910000000-d969ff7bbc61fa67e0902021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - [8]-Shogaol 40V, Negative-QTOFsplash10-01c9-7900000000-f0e945b67230d4f409162021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - [8]-Shogaol 10V, Positive-QTOFsplash10-002r-0940000000-7539d94259bc6d6ea4eb2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - [8]-Shogaol 20V, Positive-QTOFsplash10-052r-5910000000-95c63f7cd49c9953b9a82021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - [8]-Shogaol 40V, Positive-QTOFsplash10-0fy9-4900000000-79cdde4da585ea08da9b2021-09-25Wishart LabView Spectrum
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 IDFDB011861
KNApSAcK IDC00035688
Chemspider ID10679
KEGG Compound IDC10494
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5281794
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1826871
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.. .