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Record Information
Version1.0
Created at2022-09-10 10:38:43 UTC
Updated at2022-09-10 10:38:43 UTC
NP-MRD IDNP0299039
Secondary Accession NumbersNone
Natural Product Identification
Common Name4,13-dihydroxy-17-(hydroxymethyl)-3,5,12,14-tetramethoxytetracyclo[7.7.1.0²,⁷.0¹¹,¹⁶]heptadeca-2,4,6,11(16),12,14-hexaen-8-one
Description4,13-Dihydroxy-17-(hydroxymethyl)-3,5,12,14-tetramethoxytetracyclo[7.7.1.0²,⁷.0¹¹,¹⁶]Heptadeca-2,4,6,11,13,15-hexaen-8-one belongs to the class of organic compounds known as aryltetralin lignans. These are lignans with a structure based on the 1-phenyltetralin skeleton. 4,13-dihydroxy-17-(hydroxymethyl)-3,5,12,14-tetramethoxytetracyclo[7.7.1.0²,⁷.0¹¹,¹⁶]heptadeca-2,4,6,11(16),12,14-hexaen-8-one is found in Liriodendron tulipifera. 4,13-Dihydroxy-17-(hydroxymethyl)-3,5,12,14-tetramethoxytetracyclo[7.7.1.0²,⁷.0¹¹,¹⁶]Heptadeca-2,4,6,11,13,15-hexaen-8-one is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC22H24O8
Average Mass416.4260 Da
Monoisotopic Mass416.14712 Da
IUPAC Name4,13-dihydroxy-17-(hydroxymethyl)-3,5,12,14-tetramethoxytetracyclo[7.7.1.0²,⁷.0¹¹,¹⁶]heptadeca-2,4,6,11(16),12,14-hexaen-8-one
Traditional Name4,13-dihydroxy-17-(hydroxymethyl)-3,5,12,14-tetramethoxytetracyclo[7.7.1.0²,⁷.0¹¹,¹⁶]heptadeca-2,4,6,11(16),12,14-hexaen-8-one
CAS Registry NumberNot Available
SMILES
COC1=CC2=C(CC3C(CO)C2C2=C(OC)C(O)=C(OC)C=C2C3=O)C(OC)=C1O
InChI Identifier
InChI=1S/C22H24O8/c1-27-14-6-9-11(21(29-3)19(14)25)5-10-13(8-23)16(9)17-12(18(10)24)7-15(28-2)20(26)22(17)30-4/h6-7,10,13,16,23,25-26H,5,8H2,1-4H3
InChI KeyDWQAZCRWFAOKDV-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
Liriodendron tulipiferaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as aryltetralin lignans. These are lignans with a structure based on the 1-phenyltetralin skeleton.
KingdomOrganic compounds
Super ClassLignans, neolignans and related compounds
ClassAryltetralin lignans
Sub ClassNot Available
Direct ParentAryltetralin lignans
Alternative Parents
Substituents
  • 1-aryltetralin lignan
  • Tetralin
  • Anisole
  • Aryl alkyl ketone
  • Aryl ketone
  • Phenol ether
  • Alkyl aryl ether
  • Phenol
  • Benzenoid
  • Ketone
  • Ether
  • Organooxygen compound
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxide
  • Organic oxygen compound
  • Primary alcohol
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic 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
logP1.78ALOGPS
logP1.54ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)7.61ChemAxon
pKa (Strongest Basic)-2.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area114.68 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity108.4 m³·mol⁻¹ChemAxon
Polarizability42.03 ųChemAxon
Number of Rings4ChemAxon
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 Compound90474712
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]