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Record Information
Version2.0
Created at2022-09-12 09:41:19 UTC
Updated at2022-09-12 09:41:19 UTC
NP-MRD IDNP0327264
Secondary Accession NumbersNone
Natural Product Identification
Common Name9-(2h-1,3-benzodioxol-5-yl)-7,8-dimethoxy-3h-naphtho[2,3-c]furan-1-one
Description9-(2H-1,3-benzodioxol-5-yl)-7,8-dimethoxy-1H,3H-naphtho[2,3-c]furan-1-one belongs to the class of organic compounds known as arylnaphthalene lignans. These are lignans containing the arylnaphthalene skeleton, especially 9-(2H-1,3-benzodioxol-5-yl)-1H,3H-naphtho[2,3-c]furan-1-one or a derivative thereof. Arylnaphthalene lignans occur in nature and exhibit diverse biological activities. 9-(2h-1,3-benzodioxol-5-yl)-7,8-dimethoxy-3h-naphtho[2,3-c]furan-1-one is found in Linum austriacum and Linum perenne. 9-(2H-1,3-benzodioxol-5-yl)-7,8-dimethoxy-1H,3H-naphtho[2,3-c]furan-1-one is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC21H16O6
Average Mass364.3530 Da
Monoisotopic Mass364.09469 Da
IUPAC Name9-(2H-1,3-benzodioxol-5-yl)-7,8-dimethoxy-1H,3H-naphtho[2,3-c]furan-1-one
Traditional Name9-(2H-1,3-benzodioxol-5-yl)-7,8-dimethoxy-3H-naphtho[2,3-c]furan-1-one
CAS Registry NumberNot Available
SMILES
COC1=CC=C2C=C3COC(=O)C3=C(C3=CC=C4OCOC4=C3)C2=C1OC
InChI Identifier
InChI=1S/C21H16O6/c1-23-15-6-4-11-7-13-9-25-21(22)19(13)17(18(11)20(15)24-2)12-3-5-14-16(8-12)27-10-26-14/h3-8H,9-10H2,1-2H3
InChI KeyBBEFSDNXXNECSY-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Linum austriacumLOTUS Database
Linum perenneLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as arylnaphthalene lignans. These are lignans containing the arylnaphthalene skeleton, especially 9-(2H-1,3-benzodioxol-5-yl)-1H,3H-naphtho[2,3-c]furan-1-one or a derivative thereof. Arylnaphthalene lignans occur in nature and exhibit diverse biological activities.
KingdomOrganic compounds
Super ClassLignans, neolignans and related compounds
ClassArylnaphthalene lignans
Sub ClassNot Available
Direct ParentArylnaphthalene lignans
Alternative Parents
Substituents
  • Arylnaphthalene lignan skeleton
  • Lignan lactone
  • Naphthofuran
  • Isobenzofuranone
  • Phthalide
  • Naphthalene
  • Isocoumaran
  • Benzodioxole
  • Anisole
  • Alkyl aryl ether
  • Benzenoid
  • Carboxylic acid ester
  • Lactone
  • Acetal
  • Oxacycle
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Ether
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
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
logP3.53ALOGPS
logP3.47ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)13.61ChemAxon
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area63.22 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity96.92 m³·mol⁻¹ChemAxon
Polarizability36.8 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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 Compound11122050
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]