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Record Information
Version1.0
Created at2022-09-09 22:23:39 UTC
Updated at2022-09-09 22:23:39 UTC
NP-MRD IDNP0291341
Secondary Accession NumbersNone
Natural Product Identification
Common Name16-(2,4-dihydroxyphenyl)-8-(4-hydroxyphenyl)tetracyclo[7.6.1.0²,⁷.0¹⁰,¹⁵]hexadeca-2,4,6,10,12,14-hexaene-4,6,12,14-tetrol
Description16-(2,4-Dihydroxyphenyl)-8-(4-hydroxyphenyl)tetracyclo[7.6.1.0²,⁷.0¹⁰,¹⁵]Hexadeca-2(7),3,5,10(15),11,13-hexaene-4,6,12,14-tetrol belongs to the class of organic compounds known as aryltetralin lignans. These are lignans with a structure based on the 1-phenyltetralin skeleton. 16-(2,4-dihydroxyphenyl)-8-(4-hydroxyphenyl)tetracyclo[7.6.1.0²,⁷.0¹⁰,¹⁵]hexadeca-2,4,6,10,12,14-hexaene-4,6,12,14-tetrol is found in Gnetum hainanense, Gnetum macrostachyum and Gnetum parvifolium. 16-(2,4-Dihydroxyphenyl)-8-(4-hydroxyphenyl)tetracyclo[7.6.1.0²,⁷.0¹⁰,¹⁵]Hexadeca-2(7),3,5,10(15),11,13-hexaene-4,6,12,14-tetrol is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC28H22O7
Average Mass470.4770 Da
Monoisotopic Mass470.13655 Da
IUPAC Name16-(2,4-dihydroxyphenyl)-8-(4-hydroxyphenyl)tetracyclo[7.6.1.0²,⁷.0¹⁰,¹⁵]hexadeca-2,4,6,10,12,14-hexaene-4,6,12,14-tetrol
Traditional Name16-(2,4-dihydroxyphenyl)-8-(4-hydroxyphenyl)tetracyclo[7.6.1.0²,⁷.0¹⁰,¹⁵]hexadeca-2,4,6,10,12,14-hexaene-4,6,12,14-tetrol
CAS Registry NumberNot Available
SMILES
OC1=CC=C(C=C1)C1C2C(C(C3=C(O)C=C(O)C=C23)C2=CC(O)=CC(O)=C12)C1=CC=C(O)C=C1O
InChI Identifier
InChI=1S/C28H22O7/c29-13-3-1-12(2-4-13)23-24-18(7-15(31)10-21(24)34)28-25-19(8-16(32)11-22(25)35)27(23)26(28)17-6-5-14(30)9-20(17)33/h1-11,23,26-35H
InChI KeyMIPUQOUHHCMZTE-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
Gnetum hainanenseLOTUS Database
Gnetum macrostachyumLOTUS Database
Gnetum parvifoliumLOTUS 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
  • Phenylnaphthalene
  • Dibenzocycloheptene
  • Tetralin
  • Indane
  • Resorcinol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Polyol
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • 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
logP3.37ALOGPS
logP5.01ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)8.96ChemAxon
pKa (Strongest Basic)-5.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area141.61 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity129.92 m³·mol⁻¹ChemAxon
Polarizability48.14 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
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 Compound73817337
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]