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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 02:44:37 UTC
Update Date2022-03-07 02:56:53 UTC
HMDB IDHMDB0041098
Secondary Accession Numbers
  • HMDB41098
Metabolite Identification
Common Name2-Hydroxy-3-methyl-4H-pyran-4-one O-(6E-cinnamoyl-b-D-glucoside)
Description2-Hydroxy-3-methyl-4H-pyran-4-one O-(6E-cinnamoyl-b-D-glucoside) belongs to the class of organic compounds known as cinnamic acid esters. These are compound containing an ester derivative of cinnamic acid. 2-Hydroxy-3-methyl-4H-pyran-4-one O-(6E-cinnamoyl-b-D-glucoside) has been detected, but not quantified in, green vegetables. This could make 2-hydroxy-3-methyl-4H-pyran-4-one O-(6E-cinnamoyl-b-D-glucoside) a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 2-Hydroxy-3-methyl-4H-pyran-4-one O-(6E-cinnamoyl-b-D-glucoside).
Structure
Data?1563863623
Synonyms
ValueSource
{3,4,5-trihydroxy-6-[(3-methyl-4-oxo-4H-pyran-2-yl)oxy]oxan-2-yl}methyl (2E)-3-phenylprop-2-enoic acidGenerator
Chemical FormulaC21H22O9
Average Molecular Weight418.394
Monoisotopic Molecular Weight418.126382302
IUPAC Name{3,4,5-trihydroxy-6-[(3-methyl-4-oxo-4H-pyran-2-yl)oxy]oxan-2-yl}methyl (2E)-3-phenylprop-2-enoate
Traditional Name{3,4,5-trihydroxy-6-[(3-methyl-4-oxopyran-2-yl)oxy]oxan-2-yl}methyl (2E)-3-phenylprop-2-enoate
CAS Registry Number84888-58-4
SMILES
CC1=C(OC2OC(COC(=O)\C=C\C3=CC=CC=C3)C(O)C(O)C2O)OC=CC1=O
InChI Identifier
InChI=1S/C21H22O9/c1-12-14(22)9-10-27-20(12)30-21-19(26)18(25)17(24)15(29-21)11-28-16(23)8-7-13-5-3-2-4-6-13/h2-10,15,17-19,21,24-26H,11H2,1H3/b8-7+
InChI KeyJRUMXTPQUYPUHC-BQYQJAHWSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cinnamic acid esters. These are compound containing an ester derivative of cinnamic acid.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCinnamic acids and derivatives
Sub ClassCinnamic acid esters
Direct ParentCinnamic acid esters
Alternative Parents
Substituents
  • Cinnamic acid ester
  • Glycosyl compound
  • O-glycosyl compound
  • Styrene
  • Fatty acid ester
  • Pyranone
  • Monocyclic benzene moiety
  • Monosaccharide
  • Oxane
  • Pyran
  • Fatty acyl
  • Benzenoid
  • Vinylogous ester
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Heteroaromatic compound
  • Secondary alcohol
  • Cyclic ketone
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Oxacycle
  • Polyol
  • Acetal
  • Organooxygen compound
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point163 - 163.7 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.75 g/LALOGPS
logP0.89ALOGPS
logP1.86ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)12.2ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area131.75 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity113.55 m³·mol⁻¹ChemAxon
Polarizability41.34 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+191.88330932474
DeepCCS[M-H]-189.52530932474
DeepCCS[M-2H]-223.17230932474
DeepCCS[M+Na]+198.40130932474
AllCCS[M+H]+198.632859911
AllCCS[M+H-H2O]+196.132859911
AllCCS[M+NH4]+200.932859911
AllCCS[M+Na]+201.632859911
AllCCS[M-H]-194.032859911
AllCCS[M+Na-2H]-194.332859911
AllCCS[M+HCOO]-194.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2-Hydroxy-3-methyl-4H-pyran-4-one O-(6E-cinnamoyl-b-D-glucoside)CC1=C(OC2OC(COC(=O)\C=C\C3=CC=CC=C3)C(O)C(O)C2O)OC=CC1=O4870.9Standard polar33892256
2-Hydroxy-3-methyl-4H-pyran-4-one O-(6E-cinnamoyl-b-D-glucoside)CC1=C(OC2OC(COC(=O)\C=C\C3=CC=CC=C3)C(O)C(O)C2O)OC=CC1=O3535.8Standard non polar33892256
2-Hydroxy-3-methyl-4H-pyran-4-one O-(6E-cinnamoyl-b-D-glucoside)CC1=C(OC2OC(COC(=O)\C=C\C3=CC=CC=C3)C(O)C(O)C2O)OC=CC1=O3835.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2-Hydroxy-3-methyl-4H-pyran-4-one O-(6E-cinnamoyl-b-D-glucoside),1TMS,isomer #1CC1=C(OC2OC(COC(=O)/C=C/C3=CC=CC=C3)C(O[Si](C)(C)C)C(O)C2O)OC=CC1=O3594.4Semi standard non polar33892256
2-Hydroxy-3-methyl-4H-pyran-4-one O-(6E-cinnamoyl-b-D-glucoside),1TMS,isomer #2CC1=C(OC2OC(COC(=O)/C=C/C3=CC=CC=C3)C(O)C(O[Si](C)(C)C)C2O)OC=CC1=O3578.1Semi standard non polar33892256
2-Hydroxy-3-methyl-4H-pyran-4-one O-(6E-cinnamoyl-b-D-glucoside),1TMS,isomer #3CC1=C(OC2OC(COC(=O)/C=C/C3=CC=CC=C3)C(O)C(O)C2O[Si](C)(C)C)OC=CC1=O3597.4Semi standard non polar33892256
2-Hydroxy-3-methyl-4H-pyran-4-one O-(6E-cinnamoyl-b-D-glucoside),2TMS,isomer #1CC1=C(OC2OC(COC(=O)/C=C/C3=CC=CC=C3)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C2O)OC=CC1=O3546.6Semi standard non polar33892256
2-Hydroxy-3-methyl-4H-pyran-4-one O-(6E-cinnamoyl-b-D-glucoside),2TMS,isomer #2CC1=C(OC2OC(COC(=O)/C=C/C3=CC=CC=C3)C(O[Si](C)(C)C)C(O)C2O[Si](C)(C)C)OC=CC1=O3552.1Semi standard non polar33892256
2-Hydroxy-3-methyl-4H-pyran-4-one O-(6E-cinnamoyl-b-D-glucoside),2TMS,isomer #3CC1=C(OC2OC(COC(=O)/C=C/C3=CC=CC=C3)C(O)C(O[Si](C)(C)C)C2O[Si](C)(C)C)OC=CC1=O3537.0Semi standard non polar33892256
2-Hydroxy-3-methyl-4H-pyran-4-one O-(6E-cinnamoyl-b-D-glucoside),3TMS,isomer #1CC1=C(OC2OC(COC(=O)/C=C/C3=CC=CC=C3)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C2O[Si](C)(C)C)OC=CC1=O3543.2Semi standard non polar33892256
2-Hydroxy-3-methyl-4H-pyran-4-one O-(6E-cinnamoyl-b-D-glucoside),1TBDMS,isomer #1CC1=C(OC2OC(COC(=O)/C=C/C3=CC=CC=C3)C(O[Si](C)(C)C(C)(C)C)C(O)C2O)OC=CC1=O3863.4Semi standard non polar33892256
2-Hydroxy-3-methyl-4H-pyran-4-one O-(6E-cinnamoyl-b-D-glucoside),1TBDMS,isomer #2CC1=C(OC2OC(COC(=O)/C=C/C3=CC=CC=C3)C(O)C(O[Si](C)(C)C(C)(C)C)C2O)OC=CC1=O3846.0Semi standard non polar33892256
2-Hydroxy-3-methyl-4H-pyran-4-one O-(6E-cinnamoyl-b-D-glucoside),1TBDMS,isomer #3CC1=C(OC2OC(COC(=O)/C=C/C3=CC=CC=C3)C(O)C(O)C2O[Si](C)(C)C(C)(C)C)OC=CC1=O3864.1Semi standard non polar33892256
2-Hydroxy-3-methyl-4H-pyran-4-one O-(6E-cinnamoyl-b-D-glucoside),2TBDMS,isomer #1CC1=C(OC2OC(COC(=O)/C=C/C3=CC=CC=C3)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C2O)OC=CC1=O4045.5Semi standard non polar33892256
2-Hydroxy-3-methyl-4H-pyran-4-one O-(6E-cinnamoyl-b-D-glucoside),2TBDMS,isomer #2CC1=C(OC2OC(COC(=O)/C=C/C3=CC=CC=C3)C(O[Si](C)(C)C(C)(C)C)C(O)C2O[Si](C)(C)C(C)(C)C)OC=CC1=O4046.1Semi standard non polar33892256
2-Hydroxy-3-methyl-4H-pyran-4-one O-(6E-cinnamoyl-b-D-glucoside),2TBDMS,isomer #3CC1=C(OC2OC(COC(=O)/C=C/C3=CC=CC=C3)C(O)C(O[Si](C)(C)C(C)(C)C)C2O[Si](C)(C)C(C)(C)C)OC=CC1=O4045.3Semi standard non polar33892256
2-Hydroxy-3-methyl-4H-pyran-4-one O-(6E-cinnamoyl-b-D-glucoside),3TBDMS,isomer #1CC1=C(OC2OC(COC(=O)/C=C/C3=CC=CC=C3)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)OC=CC1=O4255.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hydroxy-3-methyl-4H-pyran-4-one O-(6E-cinnamoyl-b-D-glucoside) GC-MS (Non-derivatized) - 70eV, Positivesplash10-0kai-5891200000-84fd51c76d33ecab6a4a2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hydroxy-3-methyl-4H-pyran-4-one O-(6E-cinnamoyl-b-D-glucoside) GC-MS (3 TMS) - 70eV, Positivesplash10-00yi-4622449000-96c3aa142159d0592ce42017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hydroxy-3-methyl-4H-pyran-4-one O-(6E-cinnamoyl-b-D-glucoside) GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hydroxy-3-methyl-4H-pyran-4-one O-(6E-cinnamoyl-b-D-glucoside) 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 - 2-Hydroxy-3-methyl-4H-pyran-4-one O-(6E-cinnamoyl-b-D-glucoside) 10V, Positive-QTOFsplash10-004i-0920200000-0c5c9d38f473aa38385b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxy-3-methyl-4H-pyran-4-one O-(6E-cinnamoyl-b-D-glucoside) 20V, Positive-QTOFsplash10-056r-1910000000-5c4d43213d51a64e71742017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxy-3-methyl-4H-pyran-4-one O-(6E-cinnamoyl-b-D-glucoside) 40V, Positive-QTOFsplash10-0a4i-3900000000-a336fc76fba3f03e89c92017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxy-3-methyl-4H-pyran-4-one O-(6E-cinnamoyl-b-D-glucoside) 10V, Negative-QTOFsplash10-004j-1910200000-6df66343fa5bab4b31f32017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxy-3-methyl-4H-pyran-4-one O-(6E-cinnamoyl-b-D-glucoside) 20V, Negative-QTOFsplash10-004j-3900000000-8fff9289de06832c3a4c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxy-3-methyl-4H-pyran-4-one O-(6E-cinnamoyl-b-D-glucoside) 40V, Negative-QTOFsplash10-0f92-7900000000-230e56fe23ed168c364b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxy-3-methyl-4H-pyran-4-one O-(6E-cinnamoyl-b-D-glucoside) 10V, Positive-QTOFsplash10-00lr-1910600000-e476d488c10c1f6f96612021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxy-3-methyl-4H-pyran-4-one O-(6E-cinnamoyl-b-D-glucoside) 20V, Positive-QTOFsplash10-0m31-1910000000-5e417bfa35527801c5d82021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxy-3-methyl-4H-pyran-4-one O-(6E-cinnamoyl-b-D-glucoside) 40V, Positive-QTOFsplash10-0udi-2900000000-e68a18516f49a22464fa2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxy-3-methyl-4H-pyran-4-one O-(6E-cinnamoyl-b-D-glucoside) 10V, Negative-QTOFsplash10-004i-0900000000-5e9301e7eae75f61107e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxy-3-methyl-4H-pyran-4-one O-(6E-cinnamoyl-b-D-glucoside) 20V, Negative-QTOFsplash10-03ed-1900000000-11f4a78fbff30e31b4f02021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxy-3-methyl-4H-pyran-4-one O-(6E-cinnamoyl-b-D-glucoside) 40V, Negative-QTOFsplash10-004i-9300000000-7eb2b91836231810c3722021-09-22Wishart 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 IDFDB020980
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131753026
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents 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.. .