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Record Information
Version4.0
StatusPredicted
Creation Date2017-09-13 05:55:38 UTC
Update Date2019-11-12 17:20:32 UTC
HMDB IDHMDB0126053
Secondary Accession NumbersNone
Metabolite Identification
Common Name3-(3,4-dihydroxy-2-methoxyphenyl)-1-(3-hydroxyphenyl)propan-1-one
Description3-(3,4-dihydroxy-2-methoxyphenyl)-1-(3-hydroxyphenyl)propan-1-one belongs to the class of organic compounds known as retro-dihydrochalcones. These are a form of normal dihydrochalcones that are structurally distinguished by the lack of oxygen functionalities at the C2'- and C6'-positions. 3-(3,4-dihydroxy-2-methoxyphenyl)-1-(3-hydroxyphenyl)propan-1-one is an extremely weak basic (essentially neutral) compound (based on its pKa). This catechol-dehydroxylation-pattern2 occurs in human gut microbiota. 3-(3,4-dihydroxy-2-methoxyphenyl)-1-(3-hydroxyphenyl)propan-1-one is a predicted metabolite generated by BioTransformer¹ that is produced by the metabolism of 3-(3,4-dihydroxy-2-methoxyphenyl)-1-(3,4-dihydroxyphenyl)propan-1-one. It is generated by Dehydroxylase enzyme via a catechol-dehydroxylation-pattern2 reaction.
Structure
Data?1563875060
SynonymsNot Available
Chemical FormulaC16H16O5
Average Molecular Weight288.299
Monoisotopic Molecular Weight288.099773615
IUPAC Name3-(3,4-dihydroxy-2-methoxyphenyl)-1-(3-hydroxyphenyl)propan-1-one
Traditional Name3-(3,4-dihydroxy-2-methoxyphenyl)-1-(3-hydroxyphenyl)propan-1-one
CAS Registry NumberNot Available
SMILES
COC1=C(CCC(=O)C2=CC(O)=CC=C2)C=CC(O)=C1O
InChI Identifier
InChI=1S/C16H16O5/c1-21-16-10(6-8-14(19)15(16)20)5-7-13(18)11-3-2-4-12(17)9-11/h2-4,6,8-9,17,19-20H,5,7H2,1H3
InChI KeyRGTPWQUDZHZTQT-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as retro-dihydrochalcones. These are a form of normal dihydrochalcones 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 ParentRetro-dihydrochalcones
Alternative Parents
Substituents
  • Retro-dihydrochalcone
  • Cinnamylphenol
  • Alkyl-phenylketone
  • Butyrophenone
  • Methoxyphenol
  • Phenylketone
  • Anisole
  • Benzoyl
  • Phenoxy compound
  • Catechol
  • Phenol ether
  • Aryl ketone
  • Aryl alkyl ketone
  • Methoxybenzene
  • Phenol
  • Alkyl aryl ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Monocyclic benzene moiety
  • Ketone
  • Ether
  • Organooxygen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.82ALOGPS
logP2.74ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)8.82ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.99 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity78.19 m³·mol⁻¹ChemAxon
Polarizability29.59 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 (3 TMS) - 70eV, Positivesplash10-000l-1210900000-50643eb35eca56053d38Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-0910000000-bb2a291ad70a57b2cb0eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0190000000-6c5441a0eb2c8047cbe7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0920000000-954db120c58525308b1aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-6900000000-397b3b43073c32234d5cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-a87124d24a2356036060Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0290000000-b6db23620e98f7bcf191Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000f-7890000000-f5651187e5085107ed75Spectrum
Biological Properties
Cellular LocationsNot Available
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 IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131832499
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. Djoumbou Feunang, Yannick (2017). Cheminformatics Tools for Enabling Metabolomics, 2017 (PhD thesis). University of Alberta.

Enzymes

General function:
Involved in magnesium ion binding
Specific function:
Catalyzes the O-methylation, and thereby the inactivation, of catecholamine neurotransmitters and catechol hormones. Also shortens the biological half-lives of certain neuroactive drugs, like L-DOPA, alpha-methyl DOPA and isoproterenol.
Gene Name:
COMT
Uniprot ID:
P21964
Molecular weight:
30036.77
Reactions
3-(3,4-dihydroxy-2-methoxyphenyl)-1-(3-hydroxyphenyl)propan-1-one → 3-(4-hydroxy-2,3-dimethoxyphenyl)-1-(3-hydroxyphenyl)propan-1-onedetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
3-(3,4-dihydroxy-2-methoxyphenyl)-1-(3-hydroxyphenyl)propan-1-one → 3,4,5-trihydroxy-6-{6-hydroxy-3-[3-(3-hydroxyphenyl)-3-oxopropyl]-2-methoxyphenoxy}oxane-2-carboxylic aciddetails
3-(3,4-dihydroxy-2-methoxyphenyl)-1-(3-hydroxyphenyl)propan-1-one → 3,4,5-trihydroxy-6-{2-hydroxy-4-[3-(3-hydroxyphenyl)-3-oxopropyl]-3-methoxyphenoxy}oxane-2-carboxylic aciddetails
3-(3,4-dihydroxy-2-methoxyphenyl)-1-(3-hydroxyphenyl)propan-1-one → 6-{3-[3-(3,4-dihydroxy-2-methoxyphenyl)propanoyl]phenoxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
General function:
sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:
SULT1A3
Uniprot ID:
P0DMM9
Molecular weight:
34195.96
Reactions
3-(3,4-dihydroxy-2-methoxyphenyl)-1-(3-hydroxyphenyl)propan-1-one → {6-hydroxy-3-[3-(3-hydroxyphenyl)-3-oxopropyl]-2-methoxyphenyl}oxidanesulfonic aciddetails
3-(3,4-dihydroxy-2-methoxyphenyl)-1-(3-hydroxyphenyl)propan-1-one → {3-[3-(3,4-dihydroxy-2-methoxyphenyl)propanoyl]phenyl}oxidanesulfonic aciddetails