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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:38:56 UTC
Update Date2019-07-23 06:07:15 UTC
HMDB IDHMDB0030772
Secondary Accession Numbers
  • HMDB30772
Metabolite Identification
Common NameDemethoxyegonol
DescriptionDemethoxyegonol belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety. Demethoxyegonol is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Demethoxyegonol has been detected, but not quantified in, mushrooms. This could make demethoxyegonol a potential biomarker for the consumption of these foods.
Structure
Data?1563862035
Synonyms
ValueSource
5-(3-Hydroxypropyl)-2-(3,4-methylenedioxyphenyl)benzofuranChEBI
2-(1,3-Benzodioxol-5-yl)-5-benzofuranpropanolHMDB
DemethoxyegonolChEBI
Chemical FormulaC18H16O4
Average Molecular Weight296.3172
Monoisotopic Molecular Weight296.104859
IUPAC Name3-[2-(2H-1,3-benzodioxol-5-yl)-1-benzofuran-5-yl]propan-1-ol
Traditional Name3-[2-(2H-1,3-benzodioxol-5-yl)-1-benzofuran-5-yl]propan-1-ol
CAS Registry Number53279-35-9
SMILES
OCCCC1=CC2=C(OC(=C2)C2=CC3=C(OCO3)C=C2)C=C1
InChI Identifier
InChI=1S/C18H16O4/c19-7-1-2-12-3-5-15-14(8-12)10-17(22-15)13-4-6-16-18(9-13)21-11-20-16/h3-6,8-10,19H,1-2,7,11H2
InChI KeyYQEPMZLWYOAQNI-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
Class2-arylbenzofuran flavonoids
Sub ClassNot Available
Direct Parent2-arylbenzofuran flavonoids
Alternative Parents
Substituents
  • 2-arylbenzofuran flavonoid
  • Benzofuran
  • Benzodioxole
  • Benzenoid
  • Heteroaromatic compound
  • Furan
  • Oxacycle
  • Organoheterocyclic compound
  • Acetal
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point124 - 125 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.031 g/LALOGPS
logP3.76ALOGPS
logP3.29ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)15.96ChemAxon
pKa (Strongest Basic)-2.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area51.83 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity81.85 m³·mol⁻¹ChemAxon
Polarizability33.17 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 (Non-derivatized) - 70eV, Positivesplash10-0udi-1090000000-35f7892a0621bae41172Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0uk9-9252000000-7b305db0b466bc367df1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004j-0090000000-7a56e0ba452241c63622Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-1090000000-cfddd6097551d7018be6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-053s-4490000000-04209bf27b64db656a06Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-07e511fd2bcc84e2f052Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0090000000-3246289027b908e0833cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002o-4290000000-c035efc0c942c39391caSpectrum
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 IDFDB002707
KNApSAcK IDC00032893
Chemspider ID8577735
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10402297
PDB IDNot Available
ChEBI ID69557
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.. .

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
Demethoxyegonol → {3-[2-(2H-1,3-benzodioxol-5-yl)-1-benzofuran-5-yl]propoxy}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
Demethoxyegonol → 6-{3-[2-(2H-1,3-benzodioxol-5-yl)-1-benzofuran-5-yl]propoxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
General function:
Involved in zinc ion binding
Specific function:
Could function in retinol oxidation for the synthesis of retinoic acid, a hormone important for cellular differentiation. Medium-chain (octanol) and aromatic (m-nitrobenzaldehyde) compounds are the best substrates. Ethanol is not a good substrate but at the high ethanol concentrations reached in the digestive tract, it plays a role in the ethanol oxidation and contributes to the first pass ethanol metabolism.
Gene Name:
ADH7
Uniprot ID:
P40394
Molecular weight:
41480.985
Reactions
Demethoxyegonol → 3-[2-(2H-1,3-benzodioxol-5-yl)-1-benzofuran-5-yl]propanaldetails