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Record Information
Version2.0
Created at2022-09-04 01:34:05 UTC
Updated at2022-09-04 01:34:05 UTC
NP-MRD IDNP0185932
Secondary Accession NumbersNone
Natural Product Identification
Common Name(4,5-dihydroxy-6-{[8-(4-hydroxy-3,5-dimethoxyphenyl)-6,7-bis(hydroxymethyl)-1,3-dimethoxy-5,6,7,8-tetrahydronaphthalen-2-yl]oxy}-3-{[3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}oxan-2-yl)methyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
Description(4,5-Dihydroxy-6-{[8-(4-hydroxy-3,5-dimethoxyphenyl)-6,7-bis(hydroxymethyl)-1,3-dimethoxy-5,6,7,8-tetrahydronaphthalen-2-yl]oxy}-3-{[3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}oxan-2-yl)methyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate belongs to the class of organic compounds known as lignan glycosides. These are aromatic polycyclic compounds containing a carbohydrate component glycosidically linked to a lignan moiety. (4,5-dihydroxy-6-{[8-(4-hydroxy-3,5-dimethoxyphenyl)-6,7-bis(hydroxymethyl)-1,3-dimethoxy-5,6,7,8-tetrahydronaphthalen-2-yl]oxy}-3-{[3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}oxan-2-yl)methyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate is found in Brucea javanica. They include 1-aryltetralin lactones (4,5-dihydroxy-6-{[8-(4-hydroxy-3,5-dimethoxyphenyl)-6,7-bis(hydroxymethyl)-1,3-dimethoxy-5,6,7,8-tetrahydronaphthalen-2-yl]oxy}-3-{[3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}oxan-2-yl)methyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
Synonyms
ValueSource
(4,5-Dihydroxy-6-{[8-(4-hydroxy-3,5-dimethoxyphenyl)-6,7-bis(hydroxymethyl)-1,3-dimethoxy-5,6,7,8-tetrahydronaphthalen-2-yl]oxy}-3-{[3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}oxan-2-yl)methyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acidGenerator
Chemical FormulaC48H54O19
Average Mass934.9410 Da
Monoisotopic Mass934.32593 Da
IUPAC Name(4,5-dihydroxy-6-{[8-(4-hydroxy-3,5-dimethoxyphenyl)-6,7-bis(hydroxymethyl)-1,3-dimethoxy-5,6,7,8-tetrahydronaphthalen-2-yl]oxy}-3-{[3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}oxan-2-yl)methyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
Traditional Name(4,5-dihydroxy-6-{[8-(4-hydroxy-3,5-dimethoxyphenyl)-6,7-bis(hydroxymethyl)-1,3-dimethoxy-5,6,7,8-tetrahydronaphthalen-2-yl]oxy}-3-{[3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}oxan-2-yl)methyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
CAS Registry NumberNot Available
SMILES
COC1=CC(C=CC(=O)OCC2OC(OC3=C(OC)C=C4CC(CO)C(CO)C(C5=CC(OC)=C(O)C(OC)=C5)C4=C3OC)C(O)C(O)C2OC(=O)C=CC2=CC=C(O)C(OC)=C2)=CC=C1O
InChI Identifier
InChI=1S/C48H54O19/c1-58-32-15-24(7-11-30(32)51)9-13-38(53)64-23-37-45(66-39(54)14-10-25-8-12-31(52)33(16-25)59-2)43(56)44(57)48(65-37)67-46-36(62-5)20-26-17-28(21-49)29(22-50)40(41(26)47(46)63-6)27-18-34(60-3)42(55)35(19-27)61-4/h7-16,18-20,28-29,37,40,43-45,48-52,55-57H,17,21-23H2,1-6H3
InChI KeyMKRYDBNUNQEYOE-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
Brucea javanicaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as lignan glycosides. These are aromatic polycyclic compounds containing a carbohydrate component glycosidically linked to a lignan moiety. They include 1-aryltetralin lactones.
KingdomOrganic compounds
Super ClassLignans, neolignans and related compounds
ClassLignan glycosides
Sub ClassNot Available
Direct ParentLignan glycosides
Alternative Parents
Substituents
  • Lignan glycoside
  • 9,9p-dihydroxyaryltetralin lignan
  • 1-aryltetralin lignan
  • Fatty acyl glycoside of mono- or disaccharide
  • Phenolic glycoside
  • Fatty acyl glycoside
  • Hydroxycinnamic acid or derivatives
  • Cinnamic acid ester
  • Alkyl glycoside
  • Coumaric acid or derivatives
  • Cinnamic acid or derivatives
  • Glycosyl compound
  • O-glycosyl compound
  • Methoxyphenol
  • Tetralin
  • Dimethoxybenzene
  • M-dimethoxybenzene
  • Anisole
  • Phenol ether
  • Styrene
  • Methoxybenzene
  • Phenoxy compound
  • Fatty acid ester
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Fatty acyl
  • Dicarboxylic acid or derivatives
  • Benzenoid
  • Oxane
  • Monosaccharide
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Secondary alcohol
  • Carboxylic acid ester
  • Organoheterocyclic compound
  • Acetal
  • Carboxylic acid derivative
  • Ether
  • Oxacycle
  • Carbonyl group
  • Organooxygen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organic oxide
  • Alcohol
  • 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
logP4.06ALOGPS
logP4.34ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)9.19ChemAxon
pKa (Strongest Basic)-2.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count17ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area268.05 ŲChemAxon
Rotatable Bond Count20ChemAxon
Refractivity238.97 m³·mol⁻¹ChemAxon
Polarizability94.63 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
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 Compound73311306
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]