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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 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 has been detected, but not quantified in, gingers (Zingiber officinale). This could make [10]-shogaol a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on [10]-Shogaol.
Structure
Data?1563862129
Synonyms
ValueSource
10-ShogaolChEMBL, HMDB
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
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.033 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+194.42530932474
DeepCCS[M-H]-192.06730932474
DeepCCS[M-2H]-224.99430932474
DeepCCS[M+Na]+200.68530932474
AllCCS[M+H]+189.332859911
AllCCS[M+H-H2O]+186.432859911
AllCCS[M+NH4]+192.032859911
AllCCS[M+Na]+192.832859911
AllCCS[M-H]-189.632859911
AllCCS[M+Na-2H]-191.132859911
AllCCS[M+HCOO]-193.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
[10]-ShogaolCCCCCCCCC\C=C\C(=O)CCC1=CC(OC)=C(O)C=C14367.7Standard polar33892256
[10]-ShogaolCCCCCCCCC\C=C\C(=O)CCC1=CC(OC)=C(O)C=C12627.8Standard non polar33892256
[10]-ShogaolCCCCCCCCC\C=C\C(=O)CCC1=CC(OC)=C(O)C=C12699.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
[10]-Shogaol,1TMS,isomer #1CCCCCCCCC/C=C/C(=O)CCC1=CC=C(O[Si](C)(C)C)C(OC)=C12752.7Semi standard non polar33892256
[10]-Shogaol,1TMS,isomer #2CCCCCCCCC/C=C/C(=CCC1=CC=C(O)C(OC)=C1)O[Si](C)(C)C2914.2Semi standard non polar33892256
[10]-Shogaol,2TMS,isomer #1CCCCCCCCC/C=C/C(=CCC1=CC=C(O[Si](C)(C)C)C(OC)=C1)O[Si](C)(C)C2935.8Semi standard non polar33892256
[10]-Shogaol,2TMS,isomer #1CCCCCCCCC/C=C/C(=CCC1=CC=C(O[Si](C)(C)C)C(OC)=C1)O[Si](C)(C)C2728.5Standard non polar33892256
[10]-Shogaol,1TBDMS,isomer #1CCCCCCCCC/C=C/C(=O)CCC1=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C13010.4Semi standard non polar33892256
[10]-Shogaol,1TBDMS,isomer #2CCCCCCCCC/C=C/C(=CCC1=CC=C(O)C(OC)=C1)O[Si](C)(C)C(C)(C)C3161.1Semi standard non polar33892256
[10]-Shogaol,2TBDMS,isomer #1CCCCCCCCC/C=C/C(=CCC1=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C1)O[Si](C)(C)C(C)(C)C3420.4Semi standard non polar33892256
[10]-Shogaol,2TBDMS,isomer #1CCCCCCCCC/C=C/C(=CCC1=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C1)O[Si](C)(C)C(C)(C)C3122.8Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - [10]-Shogaol GC-MS (Non-derivatized) - 70eV, Positivesplash10-003i-9741000000-5c09cfb9fce0b91beea82017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - [10]-Shogaol GC-MS (1 TMS) - 70eV, Positivesplash10-059l-9227000000-0762cda5a71cec833b392017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - [10]-Shogaol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - [10]-Shogaol 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 - [10]-Shogaol , positive-QTOFsplash10-000i-0900000000-c6c789c80c998c1030692017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - [10]-Shogaol , positive-QTOFsplash10-000i-0900000000-3fade94d291eb5f1df992017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - [10]-Shogaol 10V, Positive-QTOFsplash10-001i-0209000000-ae770316cbcb3e8bcdc52016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - [10]-Shogaol 20V, Positive-QTOFsplash10-0f80-2912000000-55363bb62eceba114bb22016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - [10]-Shogaol 40V, Positive-QTOFsplash10-0k9f-9800000000-1af91dbf54b93e916c832016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - [10]-Shogaol 10V, Negative-QTOFsplash10-001i-0209000000-36b605227b6390861cfc2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - [10]-Shogaol 20V, Negative-QTOFsplash10-001i-0906000000-81662b4141472b3b050a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - [10]-Shogaol 40V, Negative-QTOFsplash10-0006-1910000000-d8aaa5082d8a8bfc5db12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - [10]-Shogaol 10V, Negative-QTOFsplash10-001i-0109000000-31c02a6d866f4580f1ec2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - [10]-Shogaol 20V, Negative-QTOFsplash10-000t-0902000000-30ea5157a15b67714edc2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - [10]-Shogaol 40V, Negative-QTOFsplash10-0079-2910000000-0aed8d3a3e7bae66c8762021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - [10]-Shogaol 10V, Positive-QTOFsplash10-001r-0709000000-a5984514dbf40eacd58c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - [10]-Shogaol 20V, Positive-QTOFsplash10-000i-2913000000-756f9efa938c3bbf08062021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - [10]-Shogaol 40V, Positive-QTOFsplash10-0fe0-3900000000-7c5d51c3b88c17b090962021-09-24Wishart 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 IDFDB007721
KNApSAcK IDC00031418
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
MarkerDB IDNot Available
Good Scents IDrw1826861
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.. .