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Record Information
Version2.0
Created at2022-09-05 13:17:56 UTC
Updated at2022-09-05 13:17:56 UTC
NP-MRD IDNP0214098
Secondary Accession NumbersNone
Natural Product Identification
Common Name4-({5,25-dihydroxy-14-oxapentacyclo[20.2.2.2¹⁰,¹³.1¹⁵,¹⁹.0²,⁷]nonacosa-1(24),2,4,6,10,12,15(27),16,18,22,25,28-dodecaen-16-yl}oxy)-14-oxapentacyclo[20.2.2.2¹⁰,¹³.1¹⁵,¹⁹.0²,⁷]nonacosa-1(25),2(7),3,5,10,12,15(27),16,18,22(26),23,28-dodecaene-5,16,24-triol
Description4-({5,24-Dihydroxy-14-oxapentacyclo[20.2.2.2¹⁰,¹³.1¹⁵,¹⁹.0²,⁷]Nonacosa-1(24),2,4,6,10,12,15,17,19(27),22,25,28-dodecaen-16-yl}oxy)-14-oxapentacyclo[20.2.2.2¹⁰,¹³.1¹⁵,¹⁹.0²,⁷]Nonacosa-1(24),2,4,6,10,12,15,17,19(27),22,25,28-dodecaene-5,16,24-triol belongs to the class of organic compounds known as lignans, neolignans and related compounds. These are plant products of low molecular weight formed primarily from oxidative coupling of two p-propylphenol moieties. They can also be described as micromolecules with two phenylpropanoid units coupled together. They can be attached in various manners, like C5-C5', C8-C8'. Most known natural lignans are oxidized at C9 and C9´ and, based upon the way in which oxygen is incorporated into the skeleton and on the cyclization patterns, a wide range of lignans of very different structural types can be formed. 4-({5,25-dihydroxy-14-oxapentacyclo[20.2.2.2¹⁰,¹³.1¹⁵,¹⁹.0²,⁷]nonacosa-1(24),2,4,6,10,12,15(27),16,18,22,25,28-dodecaen-16-yl}oxy)-14-oxapentacyclo[20.2.2.2¹⁰,¹³.1¹⁵,¹⁹.0²,⁷]nonacosa-1(25),2(7),3,5,10,12,15(27),16,18,22(26),23,28-dodecaene-5,16,24-triol is found in Blasia pusilla. 4-({5,24-Dihydroxy-14-oxapentacyclo[20.2.2.2¹⁰,¹³.1¹⁵,¹⁹.0²,⁷]Nonacosa-1(24),2,4,6,10,12,15,17,19(27),22,25,28-dodecaen-16-yl}oxy)-14-oxapentacyclo[20.2.2.2¹⁰,¹³.1¹⁵,¹⁹.0²,⁷]Nonacosa-1(24),2,4,6,10,12,15,17,19(27),22,25,28-dodecaene-5,16,24-triol is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC56H46O8
Average Mass846.9760 Da
Monoisotopic Mass846.31927 Da
IUPAC Name4-({5,25-dihydroxy-14-oxapentacyclo[20.2.2.2¹⁰,¹³.1¹⁵,¹⁹.0²,⁷]nonacosa-1(24),2,4,6,10,12,15(27),16,18,22,25,28-dodecaen-16-yl}oxy)-14-oxapentacyclo[20.2.2.2¹⁰,¹³.1¹⁵,¹⁹.0²,⁷]nonacosa-1(25),2(7),3,5,10,12,15(27),16,18,22(26),23,28-dodecaene-5,16,24-triol
Traditional Name4-({5,25-dihydroxy-14-oxapentacyclo[20.2.2.2¹⁰,¹³.1¹⁵,¹⁹.0²,⁷]nonacosa-1(24),2,4,6,10,12,15(27),16,18,22,25,28-dodecaen-16-yl}oxy)-14-oxapentacyclo[20.2.2.2¹⁰,¹³.1¹⁵,¹⁹.0²,⁷]nonacosa-1(25),2(7),3,5,10,12,15(27),16,18,22(26),23,28-dodecaene-5,16,24-triol
CAS Registry NumberNot Available
SMILES
OC1=CC=C2C(CCC3=CC=C(OC4=CC(CCC5=CC=C2C(O)=C5)=CC=C4OC2=CC4=C(CCC5=CC=C(OC6=CC(CCC7=CC=C4C(O)=C7)=CC=C6O)C=C5)C=C2O)C=C3)=C1
InChI Identifier
InChI=1S/C56H46O8/c57-42-17-24-45-40(31-42)15-5-34-9-20-44(21-10-34)63-56-30-39(4-2-36-11-22-46(45)50(59)27-36)14-26-53(56)64-55-33-48-41(32-52(55)61)16-6-35-7-18-43(19-8-35)62-54-29-38(13-25-49(54)58)3-1-37-12-23-47(48)51(60)28-37/h7-14,17-33,57-61H,1-6,15-16H2
InChI KeyWJMHKCQBVUOZSJ-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
Blasia pusillaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as lignans, neolignans and related compounds. These are plant products of low molecular weight formed primarily from oxidative coupling of two p-propylphenol moieties. They can also be described as micromolecules with two phenylpropanoid units coupled together. They can be attached in various manners, like C5-C5', C8-C8'. Most known natural lignans are oxidized at C9 and C9´ and, based upon the way in which oxygen is incorporated into the skeleton and on the cyclization patterns, a wide range of lignans of very different structural types can be formed.
KingdomOrganic compounds
Super ClassLignans, neolignans and related compounds
ClassNot Available
Sub ClassNot Available
Direct ParentLignans, neolignans and related compounds
Alternative Parents
Substituents
  • Oxyneolignan skeleton
  • Diaryl ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen 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
logP8.54ALOGPS
logP14.45ChemAxon
logS-6.9ALOGPS
pKa (Strongest Acidic)8.14ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area128.84 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity250.19 m³·mol⁻¹ChemAxon
Polarizability90.61 ųChemAxon
Number of Rings10ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
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 CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]