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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 20:37:37 UTC
Update Date2019-07-23 06:19:06 UTC
HMDB IDHMDB0035616
Secondary Accession Numbers
  • HMDB35616
Metabolite Identification
Common Name3,3',4,4'-Tetrahydroxy-2-methoxychalcone
Description3,3',4,4'-Tetrahydroxy-2-methoxychalcone belongs to the class of organic compounds known as retrochalcones. These are a form of normal chalcones that are structurally distinguished by the lack of oxygen functionalities at the C2'- and C6'-positions. Thus, 3,3',4,4'-tetrahydroxy-2-methoxychalcone is considered to be a flavonoid lipid molecule. 3,3',4,4'-Tetrahydroxy-2-methoxychalcone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, 3,3',4,4'-Tetrahydroxy-2-methoxychalcone has been detected, but not quantified in, herbs and spices and tea. This could make 3,3',4,4'-tetrahydroxy-2-methoxychalcone a potential biomarker for the consumption of these foods.
Structure
Data?1563862746
Synonyms
ValueSource
3,4,3',4'-Tetrahydroxy-2-methoxychalconeHMDB
Chemical FormulaC16H14O6
Average Molecular Weight302.2788
Monoisotopic Molecular Weight302.07903818
IUPAC Name(2E)-3-(3,4-dihydroxy-2-methoxyphenyl)-1-(3,4-dihydroxyphenyl)prop-2-en-1-one
Traditional Name(2E)-3-(3,4-dihydroxy-2-methoxyphenyl)-1-(3,4-dihydroxyphenyl)prop-2-en-1-one
CAS Registry Number197227-39-7
SMILES
COC1=C(\C=C\C(=O)C2=CC(O)=C(O)C=C2)C=CC(O)=C1O
InChI Identifier
InChI=1S/C16H14O6/c1-22-16-9(3-7-13(19)15(16)21)2-5-11(17)10-4-6-12(18)14(20)8-10/h2-8,18-21H,1H3/b5-2+
InChI KeyBICPGUILWBQAEY-GORDUTHDSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as retrochalcones. These are a form of normal chalcones that are structurally distinguished by the lack of oxygen functionalities at the C2'- and C6'-positions.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassLinear 1,3-diarylpropanoids
Sub ClassChalcones and dihydrochalcones
Direct ParentRetrochalcones
Alternative Parents
Substituents
  • Retrochalcone
  • Cinnamylphenol
  • Hydroxycinnamic acid or derivatives
  • Methoxyphenol
  • Phenoxy compound
  • Anisole
  • Benzoyl
  • Catechol
  • Methoxybenzene
  • Phenol ether
  • Aryl ketone
  • Styrene
  • Alkyl aryl ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Enone
  • Acryloyl-group
  • Alpha,beta-unsaturated ketone
  • Ketone
  • Ether
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point196 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.06 g/LALOGPS
logP2.78ALOGPS
logP2.52ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)7.96ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area107.22 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity81.26 m³·mol⁻¹ChemAxon
Polarizability30.39 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-0951000000-f2f2cb83c5fb6350685fSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-004i-0000090000-8c0e459bd5da537d30f0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0429000000-789216f41d73f2ac0aceSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f79-0932000000-1f193024d1b4b22926afSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-5910000000-3e2ce8637160fad9d911Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0219000000-962fcb0f40ea03e9610eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0987000000-76b7a5d6ba9ac06af2f3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0abj-2940000000-662279428e4f12e3943fSpectrum
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 IDFDB014320
KNApSAcK IDC00014432
Chemspider ID4979581
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6478421
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH 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.. .