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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:38:56 UTC
Update Date2022-03-07 02:52:41 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 a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review very few articles have been published on Demethoxyegonol.
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
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point124 - 125 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility6.88 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+170.00231661259
DarkChem[M-H]-172.66931661259
DeepCCS[M+H]+172.70230932474
DeepCCS[M-H]-170.34430932474
DeepCCS[M-2H]-203.74930932474
DeepCCS[M+Na]+179.13130932474
AllCCS[M+H]+171.332859911
AllCCS[M+H-H2O]+167.732859911
AllCCS[M+NH4]+174.632859911
AllCCS[M+Na]+175.632859911
AllCCS[M-H]-175.432859911
AllCCS[M+Na-2H]-174.832859911
AllCCS[M+HCOO]-174.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
DemethoxyegonolOCCCC1=CC2=C(OC(=C2)C2=CC3=C(OCO3)C=C2)C=C13567.2Standard polar33892256
DemethoxyegonolOCCCC1=CC2=C(OC(=C2)C2=CC3=C(OCO3)C=C2)C=C12620.6Standard non polar33892256
DemethoxyegonolOCCCC1=CC2=C(OC(=C2)C2=CC3=C(OCO3)C=C2)C=C12811.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Demethoxyegonol,1TMS,isomer #1C[Si](C)(C)OCCCC1=CC=C2OC(C3=CC=C4OCOC4=C3)=CC2=C12912.3Semi standard non polar33892256
Demethoxyegonol,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCCCC1=CC=C2OC(C3=CC=C4OCOC4=C3)=CC2=C13179.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Demethoxyegonol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-1090000000-35f7892a0621bae411722017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Demethoxyegonol GC-MS (1 TMS) - 70eV, Positivesplash10-0uk9-9252000000-7b305db0b466bc367df12017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Demethoxyegonol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Demethoxyegonol 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 - Demethoxyegonol 10V, Positive-QTOFsplash10-004j-0090000000-7a56e0ba452241c636222016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Demethoxyegonol 20V, Positive-QTOFsplash10-004i-1090000000-cfddd6097551d7018be62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Demethoxyegonol 40V, Positive-QTOFsplash10-053s-4490000000-04209bf27b64db656a062016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Demethoxyegonol 10V, Negative-QTOFsplash10-0002-0090000000-07e511fd2bcc84e2f0522016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Demethoxyegonol 20V, Negative-QTOFsplash10-0002-0090000000-3246289027b908e0833c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Demethoxyegonol 40V, Negative-QTOFsplash10-002o-4290000000-c035efc0c942c39391ca2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Demethoxyegonol 10V, Negative-QTOFsplash10-0002-0090000000-bf4049e7bc52824533e32021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Demethoxyegonol 20V, Negative-QTOFsplash10-014i-0090000000-a8454a3bda9e3732235e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Demethoxyegonol 40V, Negative-QTOFsplash10-0f72-1190000000-98a086da493bae7090952021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Demethoxyegonol 10V, Positive-QTOFsplash10-002b-0090000000-36d7e0140149fd1f06f12021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Demethoxyegonol 20V, Positive-QTOFsplash10-0f92-0090000000-da5994b5fcaf2cf1f1af2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Demethoxyegonol 40V, Positive-QTOFsplash10-0udi-0090000000-a378a9c61d37e24a35da2021-09-22Wishart LabView Spectrum
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
MarkerDB IDNot Available
Good Scents IDrw1822641
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