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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:21:52 UTC
Update Date2022-03-07 02:53:47 UTC
HMDB IDHMDB0033616
Secondary Accession Numbers
  • HMDB33616
Metabolite Identification
Common Name(S)-[10]-Gingerol
Description(S)-[10]-Gingerol belongs to the class of organic compounds known as gingerols. Gingerols are compounds containing a gingerol moiety, which is structurally characterized by a 4-hydroxy-3-methoxyphenyl group substituted at the C6 carbon atom by a 5-hydroxy-alkane-3-one (S)-[10]-Gingerol is a musk and woody tasting compound (S)-[10]-Gingerol has been detected, but not quantified in, gingers (Zingiber officinale) and herbs and spices. This could make (S)-[10]-gingerol a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on (S)-[10]-Gingerol.
Structure
Data?1563862433
Synonyms
ValueSource
(10)-GingerolHMDB
(S)-5-Hydroxy-1-(4-hydroxy-3-methoxyphenyl)-3-tetradecanoneHMDB
[10]-GingerolHMDB
Chemical FormulaC21H34O4
Average Molecular Weight350.4923
Monoisotopic Molecular Weight350.245709576
IUPAC Name5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)tetradecan-3-one
Traditional Name5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)tetradecan-3-one
CAS Registry Number23513-15-7
SMILES
CCCCCCCCCC(O)CC(=O)CCC1=CC(OC)=C(O)C=C1
InChI Identifier
InChI=1S/C21H34O4/c1-3-4-5-6-7-8-9-10-18(22)16-19(23)13-11-17-12-14-20(24)21(15-17)25-2/h12,14-15,18,22,24H,3-11,13,16H2,1-2H3
InChI KeyAIULWNKTYPZYAN-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as gingerols. Gingerols are compounds containing a gingerol moiety, which is structurally characterized by a 4-hydroxy-3-methoxyphenyl group substituted at the C6 carbon atom by a 5-hydroxy-alkane-3-one.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassMethoxyphenols
Direct ParentGingerols
Alternative Parents
Substituents
  • Gingerol
  • Fatty alcohol
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Beta-hydroxy ketone
  • Fatty acyl
  • Ketone
  • Secondary alcohol
  • Ether
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxygen compound
  • Alcohol
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point45 - 46 °CNot Available
Boiling Point498.00 to 500.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility2 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP4.900 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.01 g/LALOGPS
logP5.59ALOGPS
logP5.39ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)9.95ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity101.51 m³·mol⁻¹ChemAxon
Polarizability42.14 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+188.70431661259
DarkChem[M-H]-191.40731661259
DeepCCS[M+H]+196.24230932474
DeepCCS[M-H]-193.87230932474
DeepCCS[M-2H]-226.89530932474
DeepCCS[M+Na]+202.58530932474
AllCCS[M+H]+194.132859911
AllCCS[M+H-H2O]+191.432859911
AllCCS[M+NH4]+196.632859911
AllCCS[M+Na]+197.332859911
AllCCS[M-H]-192.832859911
AllCCS[M+Na-2H]-194.432859911
AllCCS[M+HCOO]-196.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(S)-[10]-GingerolCCCCCCCCCC(O)CC(=O)CCC1=CC(OC)=C(O)C=C14465.5Standard polar33892256
(S)-[10]-GingerolCCCCCCCCCC(O)CC(=O)CCC1=CC(OC)=C(O)C=C12722.5Standard non polar33892256
(S)-[10]-GingerolCCCCCCCCCC(O)CC(=O)CCC1=CC(OC)=C(O)C=C12823.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(S)-[10]-Gingerol,1TMS,isomer #1CCCCCCCCCC(CC(=O)CCC1=CC=C(O)C(OC)=C1)O[Si](C)(C)C2748.5Semi standard non polar33892256
(S)-[10]-Gingerol,1TMS,isomer #2CCCCCCCCCC(O)CC(=O)CCC1=CC=C(O[Si](C)(C)C)C(OC)=C12853.9Semi standard non polar33892256
(S)-[10]-Gingerol,1TMS,isomer #3CCCCCCCCCC(O)CC(=CCC1=CC=C(O)C(OC)=C1)O[Si](C)(C)C2958.3Semi standard non polar33892256
(S)-[10]-Gingerol,1TMS,isomer #4CCCCCCCCCC(O)C=C(CCC1=CC=C(O)C(OC)=C1)O[Si](C)(C)C2887.0Semi standard non polar33892256
(S)-[10]-Gingerol,2TMS,isomer #1CCCCCCCCCC(CC(=O)CCC1=CC=C(O[Si](C)(C)C)C(OC)=C1)O[Si](C)(C)C2770.2Semi standard non polar33892256
(S)-[10]-Gingerol,2TMS,isomer #2CCCCCCCCCC(CC(=CCC1=CC=C(O)C(OC)=C1)O[Si](C)(C)C)O[Si](C)(C)C2905.1Semi standard non polar33892256
(S)-[10]-Gingerol,2TMS,isomer #3CCCCCCCCCC(C=C(CCC1=CC=C(O)C(OC)=C1)O[Si](C)(C)C)O[Si](C)(C)C2849.9Semi standard non polar33892256
(S)-[10]-Gingerol,2TMS,isomer #4CCCCCCCCCC(O)CC(=CCC1=CC=C(O[Si](C)(C)C)C(OC)=C1)O[Si](C)(C)C2973.7Semi standard non polar33892256
(S)-[10]-Gingerol,2TMS,isomer #5CCCCCCCCCC(O)C=C(CCC1=CC=C(O[Si](C)(C)C)C(OC)=C1)O[Si](C)(C)C2883.9Semi standard non polar33892256
(S)-[10]-Gingerol,3TMS,isomer #1CCCCCCCCCC(CC(=CCC1=CC=C(O[Si](C)(C)C)C(OC)=C1)O[Si](C)(C)C)O[Si](C)(C)C2922.8Semi standard non polar33892256
(S)-[10]-Gingerol,3TMS,isomer #1CCCCCCCCCC(CC(=CCC1=CC=C(O[Si](C)(C)C)C(OC)=C1)O[Si](C)(C)C)O[Si](C)(C)C2812.1Standard non polar33892256
(S)-[10]-Gingerol,3TMS,isomer #2CCCCCCCCCC(C=C(CCC1=CC=C(O[Si](C)(C)C)C(OC)=C1)O[Si](C)(C)C)O[Si](C)(C)C2843.5Semi standard non polar33892256
(S)-[10]-Gingerol,3TMS,isomer #2CCCCCCCCCC(C=C(CCC1=CC=C(O[Si](C)(C)C)C(OC)=C1)O[Si](C)(C)C)O[Si](C)(C)C2753.2Standard non polar33892256
(S)-[10]-Gingerol,1TBDMS,isomer #1CCCCCCCCCC(CC(=O)CCC1=CC=C(O)C(OC)=C1)O[Si](C)(C)C(C)(C)C2986.8Semi standard non polar33892256
(S)-[10]-Gingerol,1TBDMS,isomer #2CCCCCCCCCC(O)CC(=O)CCC1=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C13093.8Semi standard non polar33892256
(S)-[10]-Gingerol,1TBDMS,isomer #3CCCCCCCCCC(O)CC(=CCC1=CC=C(O)C(OC)=C1)O[Si](C)(C)C(C)(C)C3200.4Semi standard non polar33892256
(S)-[10]-Gingerol,1TBDMS,isomer #4CCCCCCCCCC(O)C=C(CCC1=CC=C(O)C(OC)=C1)O[Si](C)(C)C(C)(C)C3132.5Semi standard non polar33892256
(S)-[10]-Gingerol,2TBDMS,isomer #1CCCCCCCCCC(CC(=O)CCC1=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C1)O[Si](C)(C)C(C)(C)C3234.1Semi standard non polar33892256
(S)-[10]-Gingerol,2TBDMS,isomer #2CCCCCCCCCC(CC(=CCC1=CC=C(O)C(OC)=C1)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3372.4Semi standard non polar33892256
(S)-[10]-Gingerol,2TBDMS,isomer #3CCCCCCCCCC(C=C(CCC1=CC=C(O)C(OC)=C1)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3331.5Semi standard non polar33892256
(S)-[10]-Gingerol,2TBDMS,isomer #4CCCCCCCCCC(O)CC(=CCC1=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C1)O[Si](C)(C)C(C)(C)C3456.0Semi standard non polar33892256
(S)-[10]-Gingerol,2TBDMS,isomer #5CCCCCCCCCC(O)C=C(CCC1=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C1)O[Si](C)(C)C(C)(C)C3376.7Semi standard non polar33892256
(S)-[10]-Gingerol,3TBDMS,isomer #1CCCCCCCCCC(CC(=CCC1=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C1)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3608.6Semi standard non polar33892256
(S)-[10]-Gingerol,3TBDMS,isomer #1CCCCCCCCCC(CC(=CCC1=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C1)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3319.4Standard non polar33892256
(S)-[10]-Gingerol,3TBDMS,isomer #2CCCCCCCCCC(C=C(CCC1=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C1)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3565.3Semi standard non polar33892256
(S)-[10]-Gingerol,3TBDMS,isomer #2CCCCCCCCCC(C=C(CCC1=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C1)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3255.4Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (S)-[10]-Gingerol GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-3911000000-844d81a34f8dfcd2dd2b2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (S)-[10]-Gingerol GC-MS (2 TMS) - 70eV, Positivesplash10-0fi0-8091300000-527c8ffbf403b8e65b6a2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (S)-[10]-Gingerol 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 - (S)-[10]-Gingerol 10V, Positive-QTOFsplash10-0f89-0209000000-88b2e4785cf94422a2ed2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-[10]-Gingerol 20V, Positive-QTOFsplash10-0fc9-1902000000-d86d9638941b51db00042016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-[10]-Gingerol 40V, Positive-QTOFsplash10-052o-6910000000-17ddae55b3c1387598c42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-[10]-Gingerol 10V, Negative-QTOFsplash10-0002-0309000000-52ab87c2fc758f77177e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-[10]-Gingerol 20V, Negative-QTOFsplash10-002g-0903000000-0fa5a8390ce6dc5835ec2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-[10]-Gingerol 40V, Negative-QTOFsplash10-0a6r-3910000000-015267b6d4db8e8994dd2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-[10]-Gingerol 10V, Positive-QTOFsplash10-0ue9-0209000000-418c91995389483668622021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-[10]-Gingerol 20V, Positive-QTOFsplash10-014r-3958000000-4a4b51b2a2ed27cb0dfa2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-[10]-Gingerol 40V, Positive-QTOFsplash10-0l1c-8900000000-68b2a292051cabc6583b2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-[10]-Gingerol 10V, Negative-QTOFsplash10-001j-0009000000-9668d93711e78669059e2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-[10]-Gingerol 20V, Negative-QTOFsplash10-06rb-4916000000-c040acf5267c3c5844e12021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-[10]-Gingerol 40V, Negative-QTOFsplash10-0abi-6911000000-5bf1e9fc38d4added0032021-09-25Wishart 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 IDFDB011704
KNApSAcK IDC00031474
Chemspider ID4439827
KEGG Compound IDC17496
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5275726
PDB IDNot Available
ChEBI ID175490
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1384661
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.. .