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Record Information
Version2.0
Created at2022-09-08 02:12:04 UTC
Updated at2022-09-08 02:12:04 UTC
NP-MRD IDNP0260129
Secondary Accession NumbersNone
Natural Product Identification
Common Name(1r,9s)-3-hydroxy-4,13-dimethoxy-17-methyl-12-oxo-17-azatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2,4,6,10,13-pentaen-17-ium-17-olate
DescriptionSalutaridine N-oxide belongs to the class of organic compounds known as phenanthrenes and derivatives. These are polycyclic compounds containing a phenanthrene moiety, which is a tricyclic aromatic compound with three non-linearly fused benzene. (1r,9s)-3-hydroxy-4,13-dimethoxy-17-methyl-12-oxo-17-azatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2,4,6,10,13-pentaen-17-ium-17-olate is found in Papaver bracteatum. (1r,9s)-3-hydroxy-4,13-dimethoxy-17-methyl-12-oxo-17-azatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2,4,6,10,13-pentaen-17-ium-17-olate was first documented in 1992 (PMID: 17226487). Based on a literature review very few articles have been published on Salutaridine N-oxide.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC19H21NO5
Average Mass343.3790 Da
Monoisotopic Mass343.14197 Da
IUPAC Name(1R,9S)-3-hydroxy-4,13-dimethoxy-17-methyl-12-oxo-17-azatetracyclo[7.5.3.0^{1,10}.0^{2,7}]heptadeca-2,4,6,10,13-pentaen-17-ium-17-olate
Traditional Name(1R,9S)-3-hydroxy-4,13-dimethoxy-17-methyl-12-oxo-17-azatetracyclo[7.5.3.0^{1,10}.0^{2,7}]heptadeca-2,4,6,10,13-pentaen-17-ium-17-olate
CAS Registry NumberNot Available
SMILES
COC1=CC=C2C[C@H]3C4=CC(=O)C(OC)=C[C@@]4(CC[N+]3(C)[O-])C2=C1O
InChI Identifier
InChI=1S/C19H21NO5/c1-20(23)7-6-19-10-16(25-3)14(21)9-12(19)13(20)8-11-4-5-15(24-2)18(22)17(11)19/h4-5,9-10,13,22H,6-8H2,1-3H3/t13-,19+,20?/m0/s1
InChI KeyPARKYNUHYSJRGG-XIXJEIPKSA-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
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenanthrenes and derivatives. These are polycyclic compounds containing a phenanthrene moiety, which is a tricyclic aromatic compound with three non-linearly fused benzene.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenanthrenes and derivatives
Sub ClassNot Available
Direct ParentPhenanthrenes and derivatives
Alternative Parents
Substituents
  • Phenanthrene
  • Benzazocine
  • Isoquinolone
  • Tetralin
  • Anisole
  • Phenol ether
  • Alkyl aryl ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • Phenol
  • Piperidine
  • Trialkyl amine oxide
  • Ketone
  • Cyclic ketone
  • Organoheterocyclic compound
  • Azacycle
  • Ether
  • Trisubstituted n-oxide
  • N-oxide
  • Organic zwitterion
  • Organic salt
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organic oxide
  • Carbonyl group
  • 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
logP0.51ChemAxon
pKa (Strongest Acidic)9.65ChemAxon
pKa (Strongest Basic)3.68ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area78.82 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity95.79 m³·mol⁻¹ChemAxon
Polarizability35.33 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 Compound101642421
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Sanyar G, Gulgeze HB, Gozler B: Salutaridine N-Oxide from the Capsules of Papaver bracteatum. Planta Med. 1992 Aug;58(4):368-9. doi: 10.1055/s-2006-961487. [PubMed:17226487 ]
  2. LOTUS database [Link]