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Record Information
Version4.0
StatusPredicted
Creation Date2017-09-16 14:28:16 UTC
Update Date2019-11-12 17:21:58 UTC
HMDB IDHMDB0129367
Secondary Accession NumbersNone
Metabolite Identification
Common Name1-(2H-1,3-benzodioxol-5-yl)-3-hydroxy-3-(4-methoxy-1-benzofuran-5-yl)propan-1-one
Description1-(2H-1,3-benzodioxol-5-yl)-3-hydroxy-3-(4-methoxy-1-benzofuran-5-yl)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. 1-(2H-1,3-benzodioxol-5-yl)-3-hydroxy-3-(4-methoxy-1-benzofuran-5-yl)propan-1-one is an extremely weak basic (essentially neutral) compound (based on its pKa). 1-(2h-1,3-benzodioxol-5-yl)-3-hydroxy-3-(4-methoxy-1-benzofuran-5-yl)propan-1-one is a predicted metabolite generated by BioTransformer¹ that is produced by the metabolism of 1-(2h-1,3-benzodioxol-5-yl)-3-(4-methoxy-1-benzofuran-5-yl)propane-1,3-dione. It is generated by cyp2c9 enzyme via a reduction-of-ketone-to-alcohol reaction. This reduction-of-ketone-to-alcohol occurs in humans.
Structure
Data?1563875506
SynonymsNot Available
Chemical FormulaC19H16O6
Average Molecular Weight340.331
Monoisotopic Molecular Weight340.094688235
IUPAC Name1-(2H-1,3-benzodioxol-5-yl)-3-hydroxy-3-(4-methoxy-1-benzofuran-5-yl)propan-1-one
Traditional Name1-(2H-1,3-benzodioxol-5-yl)-3-hydroxy-3-(4-methoxy-1-benzofuran-5-yl)propan-1-one
CAS Registry NumberNot Available
SMILES
COC1=C(C=CC2=C1C=CO2)C(O)CC(=O)C1=CC2=C(OCO2)C=C1
InChI Identifier
InChI=1S/C19H16O6/c1-22-19-12(3-5-16-13(19)6-7-23-16)15(21)9-14(20)11-2-4-17-18(8-11)25-10-24-17/h2-8,15,21H,9-10H2,1H3
InChI KeyGADKVHCGHFDOPM-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
  • Butyrophenone
  • Benzodioxole
  • Benzofuran
  • Anisole
  • Aryl ketone
  • Aryl alkyl ketone
  • Alkyl aryl ether
  • Benzenoid
  • Beta-hydroxy ketone
  • Heteroaromatic compound
  • Furan
  • Secondary alcohol
  • Ketone
  • Oxacycle
  • Organoheterocyclic compound
  • Acetal
  • Ether
  • Organic oxide
  • Organic oxygen compound
  • Aromatic alcohol
  • Hydrocarbon derivative
  • Alcohol
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic 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
logP2.23ALOGPS
logP2.36ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)13.79ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area78.13 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity88.22 m³·mol⁻¹ChemAxon
Polarizability33.69 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-006t-9334000000-da9a5ec9f433be5126eaSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-1901000000-68b57433fa0814addb98Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dm-0409000000-b750952c7c6fc548735aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002b-0901000000-f351fe56dc296fbf0c92Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-0900000000-99a5bf5ef89c43fefe61Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0309000000-4d5b1c8e026a07a52529Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01vt-0903000000-c2ec1e59bb89318a54d9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01ot-1900000000-5b0d808d65630dfd905cSpectrum
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 Compound131835626
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
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 sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of many hormones, neurotransmitters, drugs and xenobiotic compounds. Sulfonation increases the water solubility of most compounds, and therefore their renal excretion, but it can also result in bioactivation to form active metabolites. Sulfates hydroxysteroids like DHEA. Isoform 1 preferentially sulfonates cholesterol, and isoform 2 avidly sulfonates pregnenolone but not cholesterol.
Gene Name:
SULT2B1
Uniprot ID:
O00204
Molecular weight:
39598.595
Reactions
1-(2H-1,3-benzodioxol-5-yl)-3-hydroxy-3-(4-methoxy-1-benzofuran-5-yl)propan-1-one → [3-(2H-1,3-benzodioxol-5-yl)-1-(4-methoxy-1-benzofuran-5-yl)-3-oxopropoxy]sulfonic aciddetails
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
1-(2H-1,3-benzodioxol-5-yl)-3-hydroxy-3-(4-methoxy-1-benzofuran-5-yl)propan-1-one → 6-[3-(2H-1,3-benzodioxol-5-yl)-1-(4-methoxy-1-benzofuran-5-yl)-3-oxopropoxy]-3,4,5-trihydroxyoxane-2-carboxylic aciddetails