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Record Information
Version1.0
Created at2022-09-09 08:49:04 UTC
Updated at2022-09-09 08:49:04 UTC
NP-MRD IDNP0282108
Secondary Accession NumbersNone
Natural Product Identification
Common Name4,5,15,16,18-pentamethoxy-10-methyl-19-oxa-10-azatetracyclo[9.8.0.0²,⁷.0¹²,¹⁷]nonadeca-2(7),3,5,12(17),13,15-hexaene
Description4,5,15,16,18-Pentamethoxy-10-methyl-19-oxa-10-azatetracyclo[9.8.0.0²,⁷.0¹²,¹⁷]Nonadeca-2,4,6,12(17),13,15-hexaene belongs to the class of organic compounds known as rhoeadine alkaloids. These are alkaloids with a structure based on rhoeadine. They usually contain a benzazepine system fused with a six-membered hemiacetal or acetal. 4,5,15,16,18-pentamethoxy-10-methyl-19-oxa-10-azatetracyclo[9.8.0.0²,⁷.0¹²,¹⁷]nonadeca-2(7),3,5,12(17),13,15-hexaene is found in Papaver bracteatum, Papaver nudicaule and Papaver tatricum. 4,5,15,16,18-Pentamethoxy-10-methyl-19-oxa-10-azatetracyclo[9.8.0.0²,⁷.0¹²,¹⁷]Nonadeca-2,4,6,12(17),13,15-hexaene is a very strong basic compound (based on its pKa).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC23H29NO6
Average Mass415.4860 Da
Monoisotopic Mass415.19949 Da
IUPAC Name4,5,15,16,18-pentamethoxy-10-methyl-19-oxa-10-azatetracyclo[9.8.0.0²,⁷.0¹²,¹⁷]nonadeca-2,4,6,12,14,16-hexaene
Traditional Name4,5,15,16,18-pentamethoxy-10-methyl-19-oxa-10-azatetracyclo[9.8.0.0²,⁷.0¹²,¹⁷]nonadeca-2,4,6,12,14,16-hexaene
CAS Registry NumberNot Available
SMILES
COC1OC2C(N(C)CCC3=CC(OC)=C(OC)C=C23)C2=CC=C(OC)C(OC)=C12
InChI Identifier
InChI=1S/C23H29NO6/c1-24-10-9-13-11-17(26-3)18(27-4)12-15(13)21-20(24)14-7-8-16(25-2)22(28-5)19(14)23(29-6)30-21/h7-8,11-12,20-21,23H,9-10H2,1-6H3
InChI KeyNGGOLDIRUNJLSH-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
Papaver bracteatumLOTUS Database
Papaver nudicauleLOTUS Database
Papaver tatricumLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as rhoeadine alkaloids. These are alkaloids with a structure based on rhoeadine. They usually contain a benzazepine system fused with a six-membered hemiacetal or acetal.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassRhoeadine alkaloids
Sub ClassNot Available
Direct ParentRhoeadine alkaloids
Alternative Parents
Substituents
  • Rhoeadine-skeleton
  • Benzazepine
  • Benzopyran
  • Isochromane
  • 2-benzopyran
  • Anisole
  • Alkyl aryl ether
  • Azepine
  • Aralkylamine
  • Benzenoid
  • Tertiary aliphatic amine
  • Tertiary amine
  • Ether
  • Organoheterocyclic compound
  • Azacycle
  • Acetal
  • Oxacycle
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Amine
  • Organopnictogen compound
  • 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
logP2.82ALOGPS
logP3.15ChemAxon
logS-3.8ALOGPS
pKa (Strongest Basic)5.95ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area58.62 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity113.1 m³·mol⁻¹ChemAxon
Polarizability45.49 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 Compound606409
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]