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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 02:07:22 UTC
Update Date2022-03-07 02:56:38 UTC
HMDB IDHMDB0040560
Secondary Accession Numbers
  • HMDB40560
Metabolite Identification
Common Name4',5,7-Trihydroxy-3-methoxyflavanone
Description4',5,7-Trihydroxy-3-methoxyflavanone belongs to the class of organic compounds known as 3-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C3 atom of the flavonoid backbone. 4',5,7-Trihydroxy-3-methoxyflavanone has been detected, but not quantified in, european plums (Prunus domestica) and fruits. This could make 4',5,7-trihydroxy-3-methoxyflavanone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 4',5,7-Trihydroxy-3-methoxyflavanone.
Structure
Data?1563863563
Synonyms
ValueSource
Aromadendrin 3-methyl etherHMDB
Chemical FormulaC16H14O6
Average Molecular Weight302.2788
Monoisotopic Molecular Weight302.07903818
IUPAC Name5,7-dihydroxy-2-(4-hydroxyphenyl)-3-methoxy-3,4-dihydro-2H-1-benzopyran-4-one
Traditional Name5,7-dihydroxy-2-(4-hydroxyphenyl)-3-methoxy-2,3-dihydro-1-benzopyran-4-one
CAS Registry Number97231-20-4
SMILES
COC1C(OC2=CC(O)=CC(O)=C2C1=O)C1=CC=C(O)C=C1
InChI Identifier
InChI=1S/C16H14O6/c1-21-16-14(20)13-11(19)6-10(18)7-12(13)22-15(16)8-2-4-9(17)5-3-8/h2-7,15-19H,1H3
InChI KeyJRLDUAGSJUMVDP-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 3-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C3 atom of the flavonoid backbone.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassO-methylated flavonoids
Direct Parent3-O-methylated flavonoids
Alternative Parents
Substituents
  • 3-methoxyflavonoid-skeleton
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Flavanone
  • Flavanonol
  • Hydroxyflavonoid
  • Flavan
  • Chromone
  • Chromane
  • Benzopyran
  • 1-benzopyran
  • Aryl ketone
  • Aryl alkyl ketone
  • Phenol
  • Alkyl aryl ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Monocyclic benzene moiety
  • Vinylogous acid
  • Ketone
  • Organoheterocyclic compound
  • Oxacycle
  • Ether
  • Dialkyl ether
  • Organooxygen compound
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point182 - 184 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.24 g/LALOGPS
logP2.51ALOGPS
logP2.76ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)7.8ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area96.22 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity77.38 m³·mol⁻¹ChemAxon
Polarizability30.13 ųChemAxon
Number of Rings3ChemAxon
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]+171.13431661259
DarkChem[M-H]-172.18331661259
DeepCCS[M+H]+173.79930932474
DeepCCS[M-H]-171.44130932474
DeepCCS[M-2H]-204.55130932474
DeepCCS[M+Na]+179.89330932474
AllCCS[M+H]+170.732859911
AllCCS[M+H-H2O]+167.132859911
AllCCS[M+NH4]+174.132859911
AllCCS[M+Na]+175.132859911
AllCCS[M-H]-170.632859911
AllCCS[M+Na-2H]-170.032859911
AllCCS[M+HCOO]-169.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4',5,7-Trihydroxy-3-methoxyflavanoneCOC1C(OC2=CC(O)=CC(O)=C2C1=O)C1=CC=C(O)C=C14131.2Standard polar33892256
4',5,7-Trihydroxy-3-methoxyflavanoneCOC1C(OC2=CC(O)=CC(O)=C2C1=O)C1=CC=C(O)C=C12862.7Standard non polar33892256
4',5,7-Trihydroxy-3-methoxyflavanoneCOC1C(OC2=CC(O)=CC(O)=C2C1=O)C1=CC=C(O)C=C12914.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4',5,7-Trihydroxy-3-methoxyflavanone,1TMS,isomer #1COC1C(=O)C2=C(O)C=C(O[Si](C)(C)C)C=C2OC1C1=CC=C(O)C=C12787.2Semi standard non polar33892256
4',5,7-Trihydroxy-3-methoxyflavanone,1TMS,isomer #2COC1C(=O)C2=C(C=C(O)C=C2O[Si](C)(C)C)OC1C1=CC=C(O)C=C12841.8Semi standard non polar33892256
4',5,7-Trihydroxy-3-methoxyflavanone,1TMS,isomer #3COC1C(=O)C2=C(O)C=C(O)C=C2OC1C1=CC=C(O[Si](C)(C)C)C=C12817.9Semi standard non polar33892256
4',5,7-Trihydroxy-3-methoxyflavanone,2TMS,isomer #1COC1C(=O)C2=C(C=C(O[Si](C)(C)C)C=C2O[Si](C)(C)C)OC1C1=CC=C(O)C=C12808.8Semi standard non polar33892256
4',5,7-Trihydroxy-3-methoxyflavanone,2TMS,isomer #2COC1C(=O)C2=C(O)C=C(O[Si](C)(C)C)C=C2OC1C1=CC=C(O[Si](C)(C)C)C=C12787.3Semi standard non polar33892256
4',5,7-Trihydroxy-3-methoxyflavanone,2TMS,isomer #3COC1C(=O)C2=C(C=C(O)C=C2O[Si](C)(C)C)OC1C1=CC=C(O[Si](C)(C)C)C=C12822.6Semi standard non polar33892256
4',5,7-Trihydroxy-3-methoxyflavanone,3TMS,isomer #1COC1C(=O)C2=C(C=C(O[Si](C)(C)C)C=C2O[Si](C)(C)C)OC1C1=CC=C(O[Si](C)(C)C)C=C12851.6Semi standard non polar33892256
4',5,7-Trihydroxy-3-methoxyflavanone,1TBDMS,isomer #1COC1C(=O)C2=C(O)C=C(O[Si](C)(C)C(C)(C)C)C=C2OC1C1=CC=C(O)C=C13063.9Semi standard non polar33892256
4',5,7-Trihydroxy-3-methoxyflavanone,1TBDMS,isomer #2COC1C(=O)C2=C(C=C(O)C=C2O[Si](C)(C)C(C)(C)C)OC1C1=CC=C(O)C=C13108.8Semi standard non polar33892256
4',5,7-Trihydroxy-3-methoxyflavanone,1TBDMS,isomer #3COC1C(=O)C2=C(O)C=C(O)C=C2OC1C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C13093.6Semi standard non polar33892256
4',5,7-Trihydroxy-3-methoxyflavanone,2TBDMS,isomer #1COC1C(=O)C2=C(C=C(O[Si](C)(C)C(C)(C)C)C=C2O[Si](C)(C)C(C)(C)C)OC1C1=CC=C(O)C=C13331.6Semi standard non polar33892256
4',5,7-Trihydroxy-3-methoxyflavanone,2TBDMS,isomer #2COC1C(=O)C2=C(O)C=C(O[Si](C)(C)C(C)(C)C)C=C2OC1C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C13298.7Semi standard non polar33892256
4',5,7-Trihydroxy-3-methoxyflavanone,2TBDMS,isomer #3COC1C(=O)C2=C(C=C(O)C=C2O[Si](C)(C)C(C)(C)C)OC1C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C13346.9Semi standard non polar33892256
4',5,7-Trihydroxy-3-methoxyflavanone,3TBDMS,isomer #1COC1C(=O)C2=C(C=C(O[Si](C)(C)C(C)(C)C)C=C2O[Si](C)(C)C(C)(C)C)OC1C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C13505.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 4',5,7-Trihydroxy-3-methoxyflavanone GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-2291000000-67bbfaae5eacca7eb48e2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4',5,7-Trihydroxy-3-methoxyflavanone GC-MS (3 TMS) - 70eV, Positivesplash10-0w2a-3660960000-c80c5e192ab6921ccbfc2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4',5,7-Trihydroxy-3-methoxyflavanone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4',5,7-Trihydroxy-3-methoxyflavanone 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 - 4',5,7-Trihydroxy-3-methoxyflavanone 10V, Positive-QTOFsplash10-0udi-0119000000-48a22238f710ab9b49532017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4',5,7-Trihydroxy-3-methoxyflavanone 20V, Positive-QTOFsplash10-0udi-0943000000-a6da096fdfa945aa7ce32017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4',5,7-Trihydroxy-3-methoxyflavanone 40V, Positive-QTOFsplash10-0pk9-6900000000-7af939d82d115f41339b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4',5,7-Trihydroxy-3-methoxyflavanone 10V, Negative-QTOFsplash10-0udi-0009000000-158f06dd39141607ae6c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4',5,7-Trihydroxy-3-methoxyflavanone 20V, Negative-QTOFsplash10-0udi-1659000000-0e86c8d039c2aedd61d02017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4',5,7-Trihydroxy-3-methoxyflavanone 40V, Negative-QTOFsplash10-054x-3910000000-d81ad711ffd90d0739692017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4',5,7-Trihydroxy-3-methoxyflavanone 10V, Negative-QTOFsplash10-0udi-0009000000-b74362932d87e15c9ce22021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4',5,7-Trihydroxy-3-methoxyflavanone 20V, Negative-QTOFsplash10-0udi-0908000000-a33c540e1e4f32c0752f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4',5,7-Trihydroxy-3-methoxyflavanone 40V, Negative-QTOFsplash10-0002-0900000000-1f1d5f28d6abefdbdb672021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4',5,7-Trihydroxy-3-methoxyflavanone 10V, Positive-QTOFsplash10-0udi-0009000000-768be1604df8995499992021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4',5,7-Trihydroxy-3-methoxyflavanone 20V, Positive-QTOFsplash10-0udi-0904000000-1c4752a08f2208a555cd2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4',5,7-Trihydroxy-3-methoxyflavanone 40V, Positive-QTOFsplash10-0udi-0900000000-28482acef80ed3292a4b2021-09-22Wishart 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 IDFDB020336
KNApSAcK IDC00008554
Chemspider ID35014960
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound14164881
PDB IDNot Available
ChEBI ID174888
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.. .