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Record Information
Version2.0
Created at2022-04-28 14:43:55 UTC
Updated at2022-04-28 14:43:55 UTC
NP-MRD IDNP0069380
Secondary Accession NumbersNone
Natural Product Identification
Common Name(+)-5-Methoxy-9-O-demethylhomolycorine
Description(+)-5-Methoxy-9-O-demethylhomolycorine belongs to the class of organic compounds known as homolycorine-type amaryllidaceae alkaloids. These are amaryllidaceae alkaloids compounds containing the homolycorine skeleton, made up of a [3,4-g]benzopyranone ring due to the oxidation of the hydroxyl group at the C6. They are biogenetically formed through a restructuring of lycorine-type alkaloids. (+)-5-Methoxy-9-O-demethylhomolycorine is found in Galanthus elewesii and Galanthus elwesii. Based on a literature review very few articles have been published on (+)-5-Methoxy-9-O-demethylhomolycorine.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC18H21NO5
Average Mass331.3680 Da
Monoisotopic Mass331.14197 Da
IUPAC Name(1S,10S,11S,17S)-5-hydroxy-4,11-dimethoxy-16-methyl-9-oxa-16-azatetracyclo[8.7.0.0^{2,7}.0^{13,17}]heptadeca-2,4,6,12-tetraen-8-one
Traditional Name(1S,10S,11S,17S)-5-hydroxy-4,11-dimethoxy-16-methyl-9-oxa-16-azatetracyclo[8.7.0.0^{2,7}.0^{13,17}]heptadeca-2,4,6,12-tetraen-8-one
CAS Registry NumberNot Available
SMILES
CO[C@H]1C=C2CCN(C)[C@H]2[C@H]2[C@@H]1OC(=O)C1=CC(O)=C(OC)C=C21
InChI Identifier
InChI=1S/C18H21NO5/c1-19-5-4-9-6-14(23-3)17-15(16(9)19)10-8-13(22-2)12(20)7-11(10)18(21)24-17/h6-8,14-17,20H,4-5H2,1-3H3/t14-,15-,16+,17+/m0/s1
InChI KeyYOFVRVTXKMQUBA-MWDXBVQZSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Galanthus elewesiiPlant
Galanthus elwesiiLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as homolycorine-type amaryllidaceae alkaloids. These are amaryllidaceae alkaloids compounds containing the homolycorine skeleton, made up of a [3,4-g]benzopyranone ring due to the oxidation of the hydroxyl group at the C6. They are biogenetically formed through a restructuring of lycorine-type alkaloids.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassAmaryllidaceae alkaloids
Sub ClassHomolycorine-type amaryllidaceae alkaloids
Direct ParentHomolycorine-type amaryllidaceae alkaloids
Alternative Parents
Substituents
  • Homolycorine skeleton
  • Benzopyran
  • Isochromane
  • 2-benzopyran
  • Indole or derivatives
  • Anisole
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Aralkylamine
  • N-alkylpyrrolidine
  • Benzenoid
  • Pyrrolidine
  • Tertiary aliphatic amine
  • Tertiary amine
  • Amino acid or derivatives
  • Lactone
  • Carboxylic acid ester
  • Azacycle
  • Oxacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Ether
  • Dialkyl ether
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Amine
  • 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
logP1.45ALOGPS
logP0.98ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)9.11ChemAxon
pKa (Strongest Basic)7.87ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area68.23 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity88.82 m³·mol⁻¹ChemAxon
Polarizability34.59 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 Compound15214954
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available