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Record Information
Version2.0
Created at2022-04-28 11:08:03 UTC
Updated at2022-04-28 11:08:03 UTC
NP-MRD IDNP0066909
Secondary Accession NumbersNone
Natural Product Identification
Common Name(-)-Leuconolam
Description(12S,19R)-12-ethyl-9,19-dihydroxy-8,16-diazatetracyclo[10.6.1.0²,⁷.0¹⁶,¹⁹]Nonadeca-1(18),2,4,6,8-pentaen-17-one belongs to the class of organic compounds known as rhazinilam alkaloids. These are alkaloids with a structure based on the rhazinilam skeleton, a tetracyclic compound with a complex tetracyclic carbon skeleton containing pyrrole ring embedded in its indolizine core. (-)-Leuconolam is found in Alstonia scholaris , Kopsia griffithii, Kopsia singapurensis, Leuconotis eugenifolius and Leuconotis griffithii. Based on a literature review very few articles have been published on (12S,19R)-12-ethyl-9,19-dihydroxy-8,16-diazatetracyclo[10.6.1.0²,⁷.0¹⁶,¹⁹]Nonadeca-1(18),2,4,6,8-pentaen-17-one.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC19H22N2O3
Average Mass326.3960 Da
Monoisotopic Mass326.16304 Da
IUPAC Name(12S,19R)-12-ethyl-19-hydroxy-8,16-diazatetracyclo[10.6.1.0^{2,7}.0^{16,19}]nonadeca-1(18),2(7),3,5-tetraene-9,17-dione
Traditional Name(12S,19R)-12-ethyl-19-hydroxy-8,16-diazatetracyclo[10.6.1.0^{2,7}.0^{16,19}]nonadeca-1(18),2(7),3,5-tetraene-9,17-dione
CAS Registry NumberNot Available
SMILES
CC[C@]12CCCN3C(=O)C=C(C4=C(NC(=O)CC1)C=CC=C4)[C@]23O
InChI Identifier
InChI=1S/C19H22N2O3/c1-2-18-9-5-11-21-17(23)12-14(19(18,21)24)13-6-3-4-7-15(13)20-16(22)8-10-18/h3-4,6-7,12,24H,2,5,8-11H2,1H3,(H,20,22)/t18-,19-/m0/s1
InChI KeyOXDBJKLQCGAPQX-OALUTQOASA-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
Alstonia Alstonia scholarisPlant
Kopsia griffithiiPlant
Kopsia singapurensisLOTUS Database
Leuconotis eugenifoliusPlant
Leuconotis griffithiiPlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as rhazinilam alkaloids. These are alkaloids with a structure based on the rhazinilam skeleton, a tetracyclic compound with a complex tetracyclic carbon skeleton containing pyrrole ring embedded in its indolizine core.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassRhazinilam alkaloids
Sub ClassNot Available
Direct ParentRhazinilam alkaloids
Alternative Parents
Substituents
  • Rhazinilam skeleton
  • Piperidine
  • Benzenoid
  • Pyrroline
  • Tertiary carboxylic acid amide
  • Cyclic carboximidic acid
  • Carboxamide group
  • Lactam
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboxylic acid derivative
  • Alkanolamine
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • 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
logP1.63ALOGPS
logP2.25ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)12.03ChemAxon
pKa (Strongest Basic)-0.45ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area69.64 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity92.31 m³·mol⁻¹ChemAxon
Polarizability34.42 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 ID114553200
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound154496892
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available