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Record Information
Version1.0
Created at2021-06-19 18:05:06 UTC
Updated at2021-06-29 23:51:31 UTC
NP-MRD IDNP0026150
Secondary Accession NumbersNone
Natural Product Identification
Common NameGnemonol F
Provided ByJEOL DatabaseJEOL Logo
Description Gnemonol F is found in Gnetum gnemon. It was first documented in 2003 (Iliya, I., et al.). Based on a literature review very few articles have been published on (2S)-2alpha,2'beta-Bis(4-hydroxyphenyl)-3'alpha-(3,5-dihydroxyphenyl)-4,5'-[(S)-2-(2,4-dihydroxyphenyl)ethane-1,2-diyl]-4',6-dihydroxy-2,2',3,3'-tetrahydro-3beta,6'-bibenzofuran.
Structure
Thumb
Synonyms
ValueSource
(2S)-2a,2'b-Bis(4-hydroxyphenyl)-3'a-(3,5-dihydroxyphenyl)-4,5'-[(S)-2-(2,4-dihydroxyphenyl)ethane-1,2-diyl]-4',6-dihydroxy-2,2',3,3'-tetrahydro-3b,6'-bibenzofuranGenerator
(2S)-2Α,2'β-bis(4-hydroxyphenyl)-3'α-(3,5-dihydroxyphenyl)-4,5'-[(S)-2-(2,4-dihydroxyphenyl)ethane-1,2-diyl]-4',6-dihydroxy-2,2',3,3'-tetrahydro-3β,6'-bibenzofuranGenerator
Chemical FormulaC42H32O10
Average Mass696.7080 Da
Monoisotopic Mass696.19955 Da
IUPAC Name(1S,6R,7R,11S,19S)-11-(2,4-dihydroxyphenyl)-7-(3,5-dihydroxyphenyl)-6,19-bis(4-hydroxyphenyl)-5,18-dioxapentacyclo[11.6.1.0^{2,10}.0^{4,8}.0^{17,20}]icosa-2(10),3,8,13,15,17(20)-hexaene-9,15-diol
Traditional Name(1S,6R,7R,11S,19S)-11-(2,4-dihydroxyphenyl)-7-(3,5-dihydroxyphenyl)-6,19-bis(4-hydroxyphenyl)-5,18-dioxapentacyclo[11.6.1.0^{2,10}.0^{4,8}.0^{17,20}]icosa-2(10),3,8,13,15,17(20)-hexaene-9,15-diol
CAS Registry NumberNot Available
SMILES
[H]OC1=C([H])C([H])=C(C([H])=C1[H])[C@]1([H])OC2=C([H])C3=C(C(O[H])=C2[C@@]1([H])C1=C([H])C(O[H])=C([H])C(O[H])=C1[H])[C@]([H])(C1=C([H])C([H])=C(O[H])C([H])=C1O[H])C([H])([H])C1=C([H])C(O[H])=C([H])C2=C1[C@@]3([H])[C@]([H])(O2)C1=C([H])C([H])=C(O[H])C([H])=C1[H]
InChI Identifier
InChI=1S/C42H32O10/c43-23-5-1-19(2-6-23)41-36(21-11-26(46)15-27(47)12-21)39-34(52-41)18-31-37(40(39)50)30(29-10-9-25(45)16-32(29)49)14-22-13-28(48)17-33-35(22)38(31)42(51-33)20-3-7-24(44)8-4-20/h1-13,15-18,30,36,38,41-50H,14H2/t30-,36+,38-,41-,42+/m0/s1
InChI KeyXIHCOJVIUYCWST-SLZRPCNNSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 400 MHz, acetone-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, acetone-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, acetone-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, acetone-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, acetone-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, acetone-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, acetone-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, acetone-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, acetone-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, acetone-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, acetone-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, acetone-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, acetone-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, acetone-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, acetone-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, acetone-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, acetone-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, acetone-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, acetone-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, acetone-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Gnetum gnemonJEOL database
    • Iliya, I., et al, Chem. Pharm. Bull. 51, 85 (2003)
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
Class2-arylbenzofuran flavonoids
Sub ClassNot Available
Direct Parent2-arylbenzofuran flavonoids
Alternative Parents
Substituents
  • 2-arylbenzofuran flavonoid
  • Linear 1,7-diphenylheptane skeleton
  • Neolignan skeleton
  • 1-phenylcoumaran
  • Dibenzocycloheptene
  • Stilbene
  • Coumaran
  • Benzofuran
  • Resorcinol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Oxacycle
  • Organoheterocyclic compound
  • 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
logP5.09ALOGPS
logP7.86ChemAxon
logS-5.6ALOGPS
pKa (Strongest Acidic)8.68ChemAxon
pKa (Strongest Basic)-5.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area180.3 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity192.07 m³·mol⁻¹ChemAxon
Polarizability74.15 ųChemAxon
Number of Rings9ChemAxon
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 Compound101215353
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Iliya, I., et al. (2003). Iliya, I., et al, Chem. Pharm. Bull. 51, 85 (2003). Chem. Pharm. Bull..