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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 03:18:31 UTC
Update Date2022-03-07 02:57:05 UTC
HMDB IDHMDB0041617
Secondary Accession Numbers
  • HMDB41617
Metabolite Identification
Common NameChavicol O-beta-glucopyranoside
DescriptionChavicol O-beta-glucopyranoside belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose. Chavicol O-beta-glucopyranoside is a sweet tasting compound. Based on a literature review very few articles have been published on Chavicol O-beta-glucopyranoside.
Structure
Data?1563863683
Synonyms
ValueSource
Chavicol O-b-glucopyranosideGenerator
Chavicol O-β-glucopyranosideGenerator
4-(2-Propenyl)phenol, 9ciHMDB
O-b-GlucopyranosideHMDB
Chemical FormulaC15H20O6
Average Molecular Weight296.319
Monoisotopic Molecular Weight296.125988364
IUPAC Name2-(hydroxymethyl)-6-[4-(prop-2-en-1-yl)phenoxy]oxane-3,4,5-triol
Traditional Name2-(hydroxymethyl)-6-[4-(prop-2-en-1-yl)phenoxy]oxane-3,4,5-triol
CAS Registry Number64703-98-6
SMILES
OCC1OC(OC2=CC=C(CC=C)C=C2)C(O)C(O)C1O
InChI Identifier
InChI=1S/C15H20O6/c1-2-3-9-4-6-10(7-5-9)20-15-14(19)13(18)12(17)11(8-16)21-15/h2,4-7,11-19H,1,3,8H2
InChI KeyBGWWYZXBGAKMRB-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentPhenolic glycosides
Alternative Parents
Substituents
  • Phenolic glycoside
  • O-glycosyl compound
  • Phenoxy compound
  • Phenol ether
  • Monocyclic benzene moiety
  • Monosaccharide
  • Benzenoid
  • Oxane
  • Secondary alcohol
  • Acetal
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Alcohol
  • Primary alcohol
  • Hydrocarbon derivative
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point149 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility2214 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility19.3 g/LALOGPS
logP0.29ALOGPS
logP0.5ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)12.2ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area99.38 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity74.47 m³·mol⁻¹ChemAxon
Polarizability30.37 ųChemAxon
Number of Rings2ChemAxon
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]+167.18531661259
DarkChem[M-H]-168.21131661259
DeepCCS[M+H]+166.66230932474
DeepCCS[M-H]-164.30430932474
DeepCCS[M-2H]-197.18930932474
DeepCCS[M+Na]+172.75530932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Chavicol O-beta-glucopyranosideOCC1OC(OC2=CC=C(CC=C)C=C2)C(O)C(O)C1O3173.9Standard polar33892256
Chavicol O-beta-glucopyranosideOCC1OC(OC2=CC=C(CC=C)C=C2)C(O)C(O)C1O2606.9Standard non polar33892256
Chavicol O-beta-glucopyranosideOCC1OC(OC2=CC=C(CC=C)C=C2)C(O)C(O)C1O2590.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Chavicol O-beta-glucopyranoside,1TMS,isomer #1C=CCC1=CC=C(OC2OC(CO[Si](C)(C)C)C(O)C(O)C2O)C=C12529.8Semi standard non polar33892256
Chavicol O-beta-glucopyranoside,1TMS,isomer #2C=CCC1=CC=C(OC2OC(CO)C(O)C(O)C2O[Si](C)(C)C)C=C12514.2Semi standard non polar33892256
Chavicol O-beta-glucopyranoside,1TMS,isomer #3C=CCC1=CC=C(OC2OC(CO)C(O)C(O[Si](C)(C)C)C2O)C=C12514.6Semi standard non polar33892256
Chavicol O-beta-glucopyranoside,1TMS,isomer #4C=CCC1=CC=C(OC2OC(CO)C(O[Si](C)(C)C)C(O)C2O)C=C12520.3Semi standard non polar33892256
Chavicol O-beta-glucopyranoside,2TMS,isomer #1C=CCC1=CC=C(OC2OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O)C2O)C=C12535.6Semi standard non polar33892256
Chavicol O-beta-glucopyranoside,2TMS,isomer #2C=CCC1=CC=C(OC2OC(CO[Si](C)(C)C)C(O)C(O[Si](C)(C)C)C2O)C=C12546.9Semi standard non polar33892256
Chavicol O-beta-glucopyranoside,2TMS,isomer #3C=CCC1=CC=C(OC2OC(CO[Si](C)(C)C)C(O)C(O)C2O[Si](C)(C)C)C=C12536.4Semi standard non polar33892256
Chavicol O-beta-glucopyranoside,2TMS,isomer #4C=CCC1=CC=C(OC2OC(CO)C(O[Si](C)(C)C)C(O)C2O[Si](C)(C)C)C=C12532.3Semi standard non polar33892256
Chavicol O-beta-glucopyranoside,2TMS,isomer #5C=CCC1=CC=C(OC2OC(CO)C(O)C(O[Si](C)(C)C)C2O[Si](C)(C)C)C=C12526.2Semi standard non polar33892256
Chavicol O-beta-glucopyranoside,2TMS,isomer #6C=CCC1=CC=C(OC2OC(CO)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C2O)C=C12522.5Semi standard non polar33892256
Chavicol O-beta-glucopyranoside,3TMS,isomer #1C=CCC1=CC=C(OC2OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C2O)C=C12544.0Semi standard non polar33892256
Chavicol O-beta-glucopyranoside,3TMS,isomer #2C=CCC1=CC=C(OC2OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O)C2O[Si](C)(C)C)C=C12559.4Semi standard non polar33892256
Chavicol O-beta-glucopyranoside,3TMS,isomer #3C=CCC1=CC=C(OC2OC(CO[Si](C)(C)C)C(O)C(O[Si](C)(C)C)C2O[Si](C)(C)C)C=C12532.2Semi standard non polar33892256
Chavicol O-beta-glucopyranoside,3TMS,isomer #4C=CCC1=CC=C(OC2OC(CO)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C2O[Si](C)(C)C)C=C12513.9Semi standard non polar33892256
Chavicol O-beta-glucopyranoside,4TMS,isomer #1C=CCC1=CC=C(OC2OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C2O[Si](C)(C)C)C=C12573.8Semi standard non polar33892256
Chavicol O-beta-glucopyranoside,1TBDMS,isomer #1C=CCC1=CC=C(OC2OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O)C2O)C=C12789.3Semi standard non polar33892256
Chavicol O-beta-glucopyranoside,1TBDMS,isomer #2C=CCC1=CC=C(OC2OC(CO)C(O)C(O)C2O[Si](C)(C)C(C)(C)C)C=C12791.1Semi standard non polar33892256
Chavicol O-beta-glucopyranoside,1TBDMS,isomer #3C=CCC1=CC=C(OC2OC(CO)C(O)C(O[Si](C)(C)C(C)(C)C)C2O)C=C12796.0Semi standard non polar33892256
Chavicol O-beta-glucopyranoside,1TBDMS,isomer #4C=CCC1=CC=C(OC2OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O)C2O)C=C12791.3Semi standard non polar33892256
Chavicol O-beta-glucopyranoside,2TBDMS,isomer #1C=CCC1=CC=C(OC2OC(CO[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O)C2O)C=C13005.6Semi standard non polar33892256
Chavicol O-beta-glucopyranoside,2TBDMS,isomer #2C=CCC1=CC=C(OC2OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O[Si](C)(C)C(C)(C)C)C2O)C=C13009.1Semi standard non polar33892256
Chavicol O-beta-glucopyranoside,2TBDMS,isomer #3C=CCC1=CC=C(OC2OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O)C2O[Si](C)(C)C(C)(C)C)C=C13007.9Semi standard non polar33892256
Chavicol O-beta-glucopyranoside,2TBDMS,isomer #4C=CCC1=CC=C(OC2OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O)C2O[Si](C)(C)C(C)(C)C)C=C13011.6Semi standard non polar33892256
Chavicol O-beta-glucopyranoside,2TBDMS,isomer #5C=CCC1=CC=C(OC2OC(CO)C(O)C(O[Si](C)(C)C(C)(C)C)C2O[Si](C)(C)C(C)(C)C)C=C13011.7Semi standard non polar33892256
Chavicol O-beta-glucopyranoside,2TBDMS,isomer #6C=CCC1=CC=C(OC2OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C2O)C=C13007.3Semi standard non polar33892256
Chavicol O-beta-glucopyranoside,3TBDMS,isomer #1C=CCC1=CC=C(OC2OC(CO[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C2O)C=C13245.5Semi standard non polar33892256
Chavicol O-beta-glucopyranoside,3TBDMS,isomer #2C=CCC1=CC=C(OC2OC(CO[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O)C2O[Si](C)(C)C(C)(C)C)C=C13275.0Semi standard non polar33892256
Chavicol O-beta-glucopyranoside,3TBDMS,isomer #3C=CCC1=CC=C(OC2OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O[Si](C)(C)C(C)(C)C)C2O[Si](C)(C)C(C)(C)C)C=C13236.3Semi standard non polar33892256
Chavicol O-beta-glucopyranoside,3TBDMS,isomer #4C=CCC1=CC=C(OC2OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C2O[Si](C)(C)C(C)(C)C)C=C13222.7Semi standard non polar33892256
Chavicol O-beta-glucopyranoside,4TBDMS,isomer #1C=CCC1=CC=C(OC2OC(CO[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C2O[Si](C)(C)C(C)(C)C)C=C13473.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Chavicol O-beta-glucopyranoside GC-MS (Non-derivatized) - 70eV, Positivesplash10-0pe9-8980000000-7ed20283277969f7df8e2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Chavicol O-beta-glucopyranoside GC-MS (4 TMS) - 70eV, Positivesplash10-00xr-1211390000-8c5eaa7097ea240facbf2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Chavicol O-beta-glucopyranoside 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 - Chavicol O-beta-glucopyranoside 10V, Positive-QTOFsplash10-000j-0960000000-267805db5350347a60672017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chavicol O-beta-glucopyranoside 20V, Positive-QTOFsplash10-000i-0900000000-f4346692bfaf69aba6042017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chavicol O-beta-glucopyranoside 40V, Positive-QTOFsplash10-00ku-5900000000-40aeb7b204f21e9d1fbb2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chavicol O-beta-glucopyranoside 10V, Negative-QTOFsplash10-000t-0890000000-ae5895c67e57ff1b4aa42017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chavicol O-beta-glucopyranoside 20V, Negative-QTOFsplash10-001i-0910000000-f31a0c0998dc7b9061762017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chavicol O-beta-glucopyranoside 40V, Negative-QTOFsplash10-001i-2900000000-bfefc1e972fb52d34e3a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chavicol O-beta-glucopyranoside 10V, Negative-QTOFsplash10-001j-0940000000-1a3eae4df3df2c79268b2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chavicol O-beta-glucopyranoside 20V, Negative-QTOFsplash10-001i-2920000000-c753199fb96c23092b4c2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chavicol O-beta-glucopyranoside 40V, Negative-QTOFsplash10-0a59-2900000000-67d20838782febb89fcb2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chavicol O-beta-glucopyranoside 10V, Positive-QTOFsplash10-0a4j-0910000000-21ceeb779a714aeb07e32021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chavicol O-beta-glucopyranoside 20V, Positive-QTOFsplash10-05r9-2920000000-724d64810f50a8700ab82021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chavicol O-beta-glucopyranoside 40V, Positive-QTOFsplash10-0a4l-8910000000-a269638f2bd9495b30142021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
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 IDFDB021778
KNApSAcK IDC00045259
Chemspider ID23194209
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound44338426
PDB IDNot Available
ChEBI ID174822
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1600531
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.. .