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Record Information
Version2.0
Created at2022-09-03 03:16:05 UTC
Updated at2022-09-03 03:16:05 UTC
NP-MRD IDNP0167638
Secondary Accession NumbersNone
Natural Product Identification
Common Name(1r,10s,12s)-4,5,12-trimethoxy-9-azatetracyclo[7.5.2.0¹,¹⁰.0²,⁷]hexadeca-2(7),3,5,13-tetraene
DescriptionO-Methylmaritidine belongs to the class of organic compounds known as phenanthridines and derivatives. These are polycyclic compounds containing a phenanthridine moiety, which is a tricyclic system with two benzene rings joined by a pyridine forming a non-linear skeleton. Hydrogenated derivatives are also included. (1r,10s,12s)-4,5,12-trimethoxy-9-azatetracyclo[7.5.2.0¹,¹⁰.0²,⁷]hexadeca-2(7),3,5,13-tetraene is found in Cyrtanthus falcatus and Narcissus papyraceus. (1r,10s,12s)-4,5,12-trimethoxy-9-azatetracyclo[7.5.2.0¹,¹⁰.0²,⁷]hexadeca-2(7),3,5,13-tetraene was first documented in 2006 (PMID: 16557463). Based on a literature review very few articles have been published on O-Methylmaritidine (PMID: 30784301).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC18H23NO3
Average Mass301.3860 Da
Monoisotopic Mass301.16779 Da
IUPAC Name(1R,10S,12S)-4,5,12-trimethoxy-9-azatetracyclo[7.5.2.0^{1,10}.0^{2,7}]hexadeca-2(7),3,5,13-tetraene
Traditional Name(1R,10S,12S)-4,5,12-trimethoxy-9-azatetracyclo[7.5.2.0^{1,10}.0^{2,7}]hexadeca-2(7),3,5,13-tetraene
CAS Registry NumberNot Available
SMILES
CO[C@H]1C[C@@H]2N3CC[C@@]2(C=C1)C1=C(C3)C=C(OC)C(OC)=C1
InChI Identifier
InChI=1S/C18H23NO3/c1-20-13-4-5-18-6-7-19(17(18)9-13)11-12-8-15(21-2)16(22-3)10-14(12)18/h4-5,8,10,13,17H,6-7,9,11H2,1-3H3/t13-,17+,18+/m1/s1
InChI KeyWFMPBYKDVOTCEI-BVGQSLNGSA-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
Cyrtanthus falcatusLOTUS Database
Narcissus papyraceusLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenanthridines and derivatives. These are polycyclic compounds containing a phenanthridine moiety, which is a tricyclic system with two benzene rings joined by a pyridine forming a non-linear skeleton. Hydrogenated derivatives are also included.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassQuinolines and derivatives
Sub ClassBenzoquinolines
Direct ParentPhenanthridines and derivatives
Alternative Parents
Substituents
  • Phenanthridine
  • Benzazepine
  • Tetrahydroisoquinoline
  • Indole or derivatives
  • Anisole
  • Phenol ether
  • Alkyl aryl ether
  • Azepine
  • Aralkylamine
  • Benzenoid
  • N-alkylpyrrolidine
  • Pyrrolidine
  • Tertiary aliphatic amine
  • Tertiary amine
  • Ether
  • Dialkyl ether
  • Azacycle
  • Amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • 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
logP2.12ALOGPS
logP1.81ChemAxon
logS-3.4ALOGPS
pKa (Strongest Basic)9.03ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area30.93 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity87.06 m³·mol⁻¹ChemAxon
Polarizability33.81 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00024421
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound101711019
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Katoch D, Kumar D, Padwad YS, Singh B, Sharma U: Pseudolycorine N-oxide, a new N-oxide from Narcissus tazetta. Nat Prod Res. 2020 Jul;34(14):2051-2058. doi: 10.1080/14786419.2019.1574785. Epub 2019 Feb 20. [PubMed:30784301 ]
  2. Elgorashi EE, Stafford GI, Jager AK, van Staden J: Inhibition of [3H]citalopram binding to the rat brain serotonin transporter by Amaryllidaceae alkaloids. Planta Med. 2006 Apr;72(5):470-3. doi: 10.1055/s-2005-916251. [PubMed:16557463 ]
  3. LOTUS database [Link]