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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 22:45:15 UTC
Update Date2022-03-07 02:55:22 UTC
HMDB IDHMDB0037503
Secondary Accession Numbers
  • HMDB37503
Metabolite Identification
Common Name3,4',5-Trihydroxy-3',7-dimethoxyflavanone
Description3,4',5-Trihydroxy-3',7-dimethoxyflavanone belongs to the class of organic compounds known as 7-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone. 3,4',5-Trihydroxy-3',7-dimethoxyflavanone has been detected, but not quantified in, several different foods, such as black tea, green tea, herbal tea, red tea, and teas (Camellia sinensis). This could make 3,4',5-trihydroxy-3',7-dimethoxyflavanone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 3,4',5-Trihydroxy-3',7-dimethoxyflavanone.
Structure
Data?1563863041
Synonyms
ValueSource
4',5-Dihydroxy-3',7-dimethoxydihydroflavonolHMDB
Taxifolin 7,3'-dimethyl etherHMDB
Chemical FormulaC17H16O7
Average Molecular Weight332.3047
Monoisotopic Molecular Weight332.089602866
IUPAC Name3,5-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-3,4-dihydro-2H-1-benzopyran-4-one
Traditional Name3,5-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-2,3-dihydro-1-benzopyran-4-one
CAS Registry Number37971-67-8
SMILES
COC1=CC(O)=C2C(=O)C(O)C(OC2=C1)C1=CC(OC)=C(O)C=C1
InChI Identifier
InChI=1S/C17H16O7/c1-22-9-6-11(19)14-13(7-9)24-17(16(21)15(14)20)8-3-4-10(18)12(5-8)23-2/h3-7,16-19,21H,1-2H3
InChI KeyDQZRHRLTSJNVBC-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 7-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassO-methylated flavonoids
Direct Parent7-O-methylated flavonoids
Alternative Parents
Substituents
  • 3p-methoxyflavonoid-skeleton
  • 7-methoxyflavonoid-skeleton
  • Flavanone
  • Flavanonol
  • 3-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • Hydroxyflavonoid
  • Flavan
  • Chromone
  • Methoxyphenol
  • Benzopyran
  • Chromane
  • 1-benzopyran
  • Phenol ether
  • Phenoxy compound
  • Methoxybenzene
  • Anisole
  • Aryl ketone
  • Aryl alkyl ketone
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • 1-hydroxy-4-unsubstituted benzenoid
  • Alkyl aryl ether
  • Benzenoid
  • Monocyclic benzene moiety
  • Vinylogous acid
  • Secondary alcohol
  • Ketone
  • Organoheterocyclic compound
  • Oxacycle
  • Ether
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • 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 Point184 - 186 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility5509 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.42 g/LALOGPS
logP1.95ALOGPS
logP2.11ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)9.53ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area105.45 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity83.57 m³·mol⁻¹ChemAxon
Polarizability32.97 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]+181.0331661259
DarkChem[M-H]-179.90331661259
DeepCCS[M+H]+180.06830932474
DeepCCS[M-H]-177.7130932474
DeepCCS[M-2H]-211.8330932474
DeepCCS[M+Na]+187.05730932474
AllCCS[M+H]+178.232859911
AllCCS[M+H-H2O]+174.832859911
AllCCS[M+NH4]+181.432859911
AllCCS[M+Na]+182.332859911
AllCCS[M-H]-178.432859911
AllCCS[M+Na-2H]-178.132859911
AllCCS[M+HCOO]-177.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3,4',5-Trihydroxy-3',7-dimethoxyflavanoneCOC1=CC(O)=C2C(=O)C(O)C(OC2=C1)C1=CC(OC)=C(O)C=C14400.9Standard polar33892256
3,4',5-Trihydroxy-3',7-dimethoxyflavanoneCOC1=CC(O)=C2C(=O)C(O)C(OC2=C1)C1=CC(OC)=C(O)C=C13021.2Standard non polar33892256
3,4',5-Trihydroxy-3',7-dimethoxyflavanoneCOC1=CC(O)=C2C(=O)C(O)C(OC2=C1)C1=CC(OC)=C(O)C=C12889.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3,4',5-Trihydroxy-3',7-dimethoxyflavanone,1TMS,isomer #1COC1=CC2=C(C(=O)C(O)C(C3=CC=C(O)C(OC)=C3)O2)C(O[Si](C)(C)C)=C13111.7Semi standard non polar33892256
3,4',5-Trihydroxy-3',7-dimethoxyflavanone,1TMS,isomer #2COC1=CC(O)=C2C(=O)C(O[Si](C)(C)C)C(C3=CC=C(O)C(OC)=C3)OC2=C12969.4Semi standard non polar33892256
3,4',5-Trihydroxy-3',7-dimethoxyflavanone,1TMS,isomer #3COC1=CC(O)=C2C(=O)C(O)C(C3=CC=C(O[Si](C)(C)C)C(OC)=C3)OC2=C13070.9Semi standard non polar33892256
3,4',5-Trihydroxy-3',7-dimethoxyflavanone,2TMS,isomer #1COC1=CC2=C(C(=O)C(O[Si](C)(C)C)C(C3=CC=C(O)C(OC)=C3)O2)C(O[Si](C)(C)C)=C12936.0Semi standard non polar33892256
3,4',5-Trihydroxy-3',7-dimethoxyflavanone,2TMS,isomer #2COC1=CC2=C(C(=O)C(O)C(C3=CC=C(O[Si](C)(C)C)C(OC)=C3)O2)C(O[Si](C)(C)C)=C13022.6Semi standard non polar33892256
3,4',5-Trihydroxy-3',7-dimethoxyflavanone,2TMS,isomer #3COC1=CC(O)=C2C(=O)C(O[Si](C)(C)C)C(C3=CC=C(O[Si](C)(C)C)C(OC)=C3)OC2=C12881.5Semi standard non polar33892256
3,4',5-Trihydroxy-3',7-dimethoxyflavanone,3TMS,isomer #1COC1=CC2=C(C(=O)C(O[Si](C)(C)C)C(C3=CC=C(O[Si](C)(C)C)C(OC)=C3)O2)C(O[Si](C)(C)C)=C12890.5Semi standard non polar33892256
3,4',5-Trihydroxy-3',7-dimethoxyflavanone,1TBDMS,isomer #1COC1=CC2=C(C(=O)C(O)C(C3=CC=C(O)C(OC)=C3)O2)C(O[Si](C)(C)C(C)(C)C)=C13360.2Semi standard non polar33892256
3,4',5-Trihydroxy-3',7-dimethoxyflavanone,1TBDMS,isomer #2COC1=CC(O)=C2C(=O)C(O[Si](C)(C)C(C)(C)C)C(C3=CC=C(O)C(OC)=C3)OC2=C13229.0Semi standard non polar33892256
3,4',5-Trihydroxy-3',7-dimethoxyflavanone,1TBDMS,isomer #3COC1=CC(O)=C2C(=O)C(O)C(C3=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C3)OC2=C13332.0Semi standard non polar33892256
3,4',5-Trihydroxy-3',7-dimethoxyflavanone,2TBDMS,isomer #1COC1=CC2=C(C(=O)C(O[Si](C)(C)C(C)(C)C)C(C3=CC=C(O)C(OC)=C3)O2)C(O[Si](C)(C)C(C)(C)C)=C13433.4Semi standard non polar33892256
3,4',5-Trihydroxy-3',7-dimethoxyflavanone,2TBDMS,isomer #2COC1=CC2=C(C(=O)C(O)C(C3=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C3)O2)C(O[Si](C)(C)C(C)(C)C)=C13519.4Semi standard non polar33892256
3,4',5-Trihydroxy-3',7-dimethoxyflavanone,2TBDMS,isomer #3COC1=CC(O)=C2C(=O)C(O[Si](C)(C)C(C)(C)C)C(C3=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C3)OC2=C13390.5Semi standard non polar33892256
3,4',5-Trihydroxy-3',7-dimethoxyflavanone,3TBDMS,isomer #1COC1=CC2=C(C(=O)C(O[Si](C)(C)C(C)(C)C)C(C3=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C3)O2)C(O[Si](C)(C)C(C)(C)C)=C13570.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3,4',5-Trihydroxy-3',7-dimethoxyflavanone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f79-0914000000-6819fe8e67185ef485e42017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,4',5-Trihydroxy-3',7-dimethoxyflavanone GC-MS (3 TMS) - 70eV, Positivesplash10-0059-9480480000-f6a14607fb2117c8be0f2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,4',5-Trihydroxy-3',7-dimethoxyflavanone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,4',5-Trihydroxy-3',7-dimethoxyflavanone 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 - 3,4',5-Trihydroxy-3',7-dimethoxyflavanone 10V, Positive-QTOFsplash10-001i-0109000000-9f55232232020e1850de2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4',5-Trihydroxy-3',7-dimethoxyflavanone 20V, Positive-QTOFsplash10-0uyi-0916000000-b31da878d20bf7d172a02015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4',5-Trihydroxy-3',7-dimethoxyflavanone 40V, Positive-QTOFsplash10-1009-1900000000-ad24031c1b8bdfda800c2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4',5-Trihydroxy-3',7-dimethoxyflavanone 10V, Negative-QTOFsplash10-001i-0209000000-5e1c53366c0f7830e7d32015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4',5-Trihydroxy-3',7-dimethoxyflavanone 20V, Negative-QTOFsplash10-0159-0936000000-095383925509ddf1370b2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4',5-Trihydroxy-3',7-dimethoxyflavanone 40V, Negative-QTOFsplash10-05ts-3930000000-8fd31f954f64642cfbf02015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4',5-Trihydroxy-3',7-dimethoxyflavanone 10V, Negative-QTOFsplash10-001i-0009000000-672be3fb3a916b6e4ef52021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4',5-Trihydroxy-3',7-dimethoxyflavanone 20V, Negative-QTOFsplash10-001i-0309000000-57fff495dfdf8e17fe0c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4',5-Trihydroxy-3',7-dimethoxyflavanone 40V, Negative-QTOFsplash10-0udi-0900000000-3ec5e45792a7fc7947ed2021-09-24Wishart 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 IDFDB016578
KNApSAcK IDC00008581
Chemspider ID35014424
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound14353345
PDB IDNot Available
ChEBI ID175236
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1861601
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.. .