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Record Information
Version1.0
Created at2022-09-09 22:25:39 UTC
Updated at2022-09-09 22:25:39 UTC
NP-MRD IDNP0291365
Secondary Accession NumbersNone
Natural Product Identification
Common Name(s)-[(2r,4s)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl](6-methoxyquinolin-4-yl)methanol
DescriptionDihydroquinidine, also known as LCN-834 or lentoquine, belongs to the class of organic compounds known as cinchona alkaloids. These are alkaloids structurally characterized by the presence of the cinchonan skeleton, which consists of a quinoline linked to an azabicyclo[2.2.2]Octane moiety. (s)-[(2r,4s)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl](6-methoxyquinolin-4-yl)methanol is found in Aspidosperma marcgravianum, Cinchona calisaya and Cinchona pubescens. It was first documented in 2019 (PMID: 31591731). Based on a literature review a significant number of articles have been published on Dihydroquinidine (PMID: 32134169) (PMID: 32123601) (PMID: 32037417) (PMID: 30712817).
Structure
Thumb
Synonyms
ValueSource
LCN-834MeSH
LentoquineMeSH
Hydroquinidine hydrochlorideMeSH
SérécorMeSH
Hydroquinidine monosulfate, (1beta,3alpha,4beta,9S)-isomerMeSH
Hydroquinidine, (1beta,3alpha,4beta,9S)-isomerMeSH
Hydroquinidine, (8alpha,9R)-isomerMeSH
Hydroquinidine, (9R)-isomerMeSH
Hydroquinidine, (9S)-(+-)-isomerMeSH
Hydroquinidine, (+-)-isomerMeSH
Hydroquinidine, (1beta,4beta,9S)-(+-)-isomerMeSH
Hydroquinidine, (8alpha,9S)-isomerMeSH
HydroquinineMeSH
LCN 834MeSH
DihydroquinineMeSH
Hydroquinidine dihydrochloride, (1beta,4beta,3S)-(+-)-isomerMeSH
Hydroquinidine monosulfate, (1beta,3alpha,4beta,8alpha,9R)-isomerMeSH
Hydroquinidine sulfateMeSH
Hydroquinidine sulfate, (9S)-isomerMeSH
Hydroquinidine, (1beta, 3alpha,4beta,8alpha,9R)-isomerMeSH
HydroquinidineMeSH
Hydroquinidine dihydrochloride, (3alpha,9S)-(+-)-isomerMeSH
Hydroquinidine monosulfateMeSH
Hydroquinidine, (3alpha,9S)-(+-)-isomerMeSH
Chemical FormulaC20H26N2O2
Average Mass326.4400 Da
Monoisotopic Mass326.19943 Da
IUPAC Name(S)-[(2R,4S)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl](6-methoxyquinolin-4-yl)methanol
Traditional Name(S)-[(2R,4S)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl](6-methoxyquinolin-4-yl)methanol
CAS Registry NumberNot Available
SMILES
CCC1CN2CC[C@H]1C[C@@H]2[C@@H](O)C1=C2C=C(OC)C=CC2=NC=C1
InChI Identifier
InChI=1S/C20H26N2O2/c1-3-13-12-22-9-7-14(13)10-19(22)20(23)16-6-8-21-18-5-4-15(24-2)11-17(16)18/h4-6,8,11,13-14,19-20,23H,3,7,9-10,12H2,1-2H3/t13?,14-,19+,20-/m0/s1
InChI KeyLJOQGZACKSYWCH-HAOVMRFASA-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
Aspidosperma marcgravianumLOTUS Database
Cinchona calisayaLOTUS Database
Cinchona pubescensLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cinchona alkaloids. These are alkaloids structurally characterized by the presence of the cinchonan skeleton, which consists of a quinoline linked to an azabicyclo[2.2.2]Octane moiety.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassCinchona alkaloids
Sub ClassNot Available
Direct ParentCinchona alkaloids
Alternative Parents
Substituents
  • Cinchonan-skeleton
  • 4-quinolinemethanol
  • Quinoline
  • Anisole
  • Phenol ether
  • Quinuclidine
  • Alkyl aryl ether
  • Aralkylamine
  • Benzenoid
  • Pyridine
  • Piperidine
  • Heteroaromatic compound
  • Tertiary aliphatic amine
  • Tertiary amine
  • Secondary alcohol
  • 1,2-aminoalcohol
  • Organoheterocyclic compound
  • Azacycle
  • Ether
  • Alcohol
  • Organonitrogen compound
  • Organooxygen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Amine
  • Hydrocarbon derivative
  • Aromatic alcohol
  • 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
logP2.82ChemAxon
pKa (Strongest Acidic)13.89ChemAxon
pKa (Strongest Basic)9.18ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area45.59 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity94.65 m³·mol⁻¹ChemAxon
Polarizability36.85 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 ID9820301
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDihydroquinidine
METLIN IDNot Available
PubChem Compound11645562
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Che Z, Yang J, Sun D, Tian Y, Liu S, Lin X, Jiang J, Chen G: Synthesis of Novel (9S)-Acyloxy Derivatives of Quinidine and Dihydroquinidine as Insecticidal Agents. Chem Biodivers. 2020 Apr;17(4):e1900696. doi: 10.1002/cbdv.201900696. Epub 2020 Mar 30. [PubMed:32134169 ]
  2. Xu D, Sanchez-Lopez E, Wang Q, Jiang Z, Marina ML: Determination of l-norvaline and l-tryptophan in dietary supplements by nano-LC using an O-[2-(methacryloyloxy)-ethylcarbamoyl]-10,11-dihydroquinidine-silica hybrid monolithic column. J Pharm Anal. 2020 Feb;10(1):70-77. doi: 10.1016/j.jpha.2019.10.001. Epub 2019 Oct 23. [PubMed:32123601 ]
  3. Zhao MX, Xiang J, Zhao ZQ, Zhao XL, Shi M: Asymmetric synthesis of dihydrocoumarins via catalytic sequential 1,6-addition/transesterification of alpha-isocyanoacetates with para-quinone methides. Org Biomol Chem. 2020 Feb 26;18(8):1637-1646. doi: 10.1039/c9ob02652e. [PubMed:32037417 ]
  4. Liu S, Fu X, Loffler R, Lammerhofer M: In-situ photopolymerized polyhedral oligomeric silsesquioxane-derived monolithic capillary columns with quinidine functionality for enantioseparation by nano-liquid chromatography. Electrophoresis. 2019 Dec;40(23-24):3132-3139. doi: 10.1002/elps.201900316. Epub 2019 Oct 15. [PubMed:31591731 ]
  5. Xu D, Wang Q, Sanchez-Lopez E, Jiang Z, Marina ML: Preparation of an O-[2-(methacryloyloxy)-ethylcarbamoyl]-10,11-dihydroquinidine-silica hybrid monolithic column for the enantioseparation of amino acids by nano-liquid chromatography. J Chromatogr A. 2019 May 24;1593:63-72. doi: 10.1016/j.chroma.2019.01.065. Epub 2019 Jan 24. [PubMed:30712817 ]
  6. LOTUS database [Link]