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Record Information
Version1.0
Created at2022-09-05 20:59:35 UTC
Updated at2022-09-05 20:59:35 UTC
NP-MRD IDNP0219859
Secondary Accession NumbersNone
Natural Product Identification
Common Name5-({5-ethoxy-4-[(3,4,5-trimethoxyphenyl)methyl]oxolan-3-yl}methyl)-2h-1,3-benzodioxole
Description5-({5-Ethoxy-4-[(3,4,5-trimethoxyphenyl)methyl]oxolan-3-yl}methyl)-2H-1,3-benzodioxole belongs to the class of organic compounds known as 9,9'-epoxylignans. These are lignans with a structure based on the 9,9'-epoxylignan skeleton, which consists of a tetrahydrofuran that carries two benzyl groups at the 3- and 4-positions. Additionally they are oxygenated at the 2-position to form dibenzylbutyrolactones (oxo group) or a dibenzylbutyrolactols (hydroxyl group). 5-({5-ethoxy-4-[(3,4,5-trimethoxyphenyl)methyl]oxolan-3-yl}methyl)-2h-1,3-benzodioxole is found in Piper cubeba. 5-({5-Ethoxy-4-[(3,4,5-trimethoxyphenyl)methyl]oxolan-3-yl}methyl)-2H-1,3-benzodioxole is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC24H30O7
Average Mass430.4970 Da
Monoisotopic Mass430.19915 Da
IUPAC Name5-({5-ethoxy-4-[(3,4,5-trimethoxyphenyl)methyl]oxolan-3-yl}methyl)-2H-1,3-benzodioxole
Traditional Name5-({5-ethoxy-4-[(3,4,5-trimethoxyphenyl)methyl]oxolan-3-yl}methyl)-2H-1,3-benzodioxole
CAS Registry NumberNot Available
SMILES
CCOC1OCC(CC2=CC=C3OCOC3=C2)C1CC1=CC(OC)=C(OC)C(OC)=C1
InChI Identifier
InChI=1S/C24H30O7/c1-5-28-24-18(9-16-11-21(25-2)23(27-4)22(12-16)26-3)17(13-29-24)8-15-6-7-19-20(10-15)31-14-30-19/h6-7,10-12,17-18,24H,5,8-9,13-14H2,1-4H3
InChI KeyPOCFXRQVXBCARH-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
Piper cubebaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 9,9'-epoxylignans. These are lignans with a structure based on the 9,9'-epoxylignan skeleton, which consists of a tetrahydrofuran that carries two benzyl groups at the 3- and 4-positions. Additionally they are oxygenated at the 2-position to form dibenzylbutyrolactones (oxo group) or a dibenzylbutyrolactols (hydroxyl group).
KingdomOrganic compounds
Super ClassLignans, neolignans and related compounds
ClassFuranoid lignans
Sub ClassTetrahydrofuran lignans
Direct Parent9,9'-epoxylignans
Alternative Parents
Substituents
  • 9,9p-epoxylignan
  • Benzodioxole
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Benzenoid
  • Tetrahydrofuran
  • Organoheterocyclic compound
  • Ether
  • Oxacycle
  • Acetal
  • Organooxygen compound
  • Hydrocarbon derivative
  • 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
logP3.42ALOGPS
logP4.09ChemAxon
logS-5ALOGPS
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area64.61 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity114.63 m³·mol⁻¹ChemAxon
Polarizability45.75 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
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 CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]