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Record Information
Version2.0
Created at2022-04-28 11:59:55 UTC
Updated at2022-04-28 11:59:55 UTC
NP-MRD IDNP0067334
Secondary Accession NumbersNone
Natural Product Identification
Common Name(+)-Isoeburnamine
Description473-99-4 Belongs to the class of organic compounds known as eburnan-type alkaloids. These are alkaloids with a structure based on the eburnan skeleton, that arises from rearrangement of the aspidospermidine ring system, involving migration of C-21 from C-7 to C-2, fission of the 2,16-bond, and attachment of C-16 to N-1. (+)-Isoeburnamine is found in Comularia camerunensis, Haplophyton cimicidum, Hunteria congolana, Hunteria eburnea, Hunteria elliotii, Hunteria umbellata, Hunteria zeylanica , Kopsia arborea, Kopsia dasyrachis, Kopsia pauciflora, Kopsia profunda and Vinca minor . Based on a literature review very few articles have been published on 473-99-4.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC19H24N2O
Average Mass296.4140 Da
Monoisotopic Mass296.18886 Da
IUPAC Name(15R,17S,19R)-15-ethyl-1,11-diazapentacyclo[9.6.2.0^{2,7}.0^{8,18}.0^{15,19}]nonadeca-2,4,6,8(18)-tetraen-17-ol
Traditional Name(15R,17S,19R)-15-ethyl-1,11-diazapentacyclo[9.6.2.0^{2,7}.0^{8,18}.0^{15,19}]nonadeca-2,4,6,8(18)-tetraen-17-ol
CAS Registry NumberNot Available
SMILES
CC[C@]12CCCN3CCC4=C([C@@H]13)N([C@@H](O)C2)C1=CC=CC=C41
InChI Identifier
InChI=1S/C19H24N2O/c1-2-19-9-5-10-20-11-8-14-13-6-3-4-7-15(13)21(16(22)12-19)17(14)18(19)20/h3-4,6-7,16,18,22H,2,5,8-12H2,1H3/t16-,18-,19+/m0/s1
InChI KeyHONLKDDLTAZVQV-YTQUADARSA-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
Comularia camerunensisPlant
Haplophyton cimicidumPlant
Hunteria congolanaPlant
Hunteria eburneaPlant
Hunteria elliotiiPlant
Hunteria umbellataLOTUS Database
Hunteria zeylanicaPlant
Kopsia arboreaLOTUS Database
Kopsia dasyrachisPlant
Kopsia paucifloraLOTUS Database
Kopsia profundaLOTUS Database
Vinca minorPlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as eburnan-type alkaloids. These are alkaloids with a structure based on the eburnan skeleton, that arises from rearrangement of the aspidospermidine ring system, involving migration of C-21 from C-7 to C-2, fission of the 2,16-bond, and attachment of C-16 to N-1.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassEburnan-type alkaloids
Sub ClassNot Available
Direct ParentEburnan-type alkaloids
Alternative Parents
Substituents
  • Eburna alkaloid
  • Indolo[3,2-1de][1,5]naphthyridine
  • Beta-carboline
  • Pyridoindole
  • Diazanaphthalene
  • Naphthyridine
  • 3-alkylindole
  • Indole
  • Indole or derivatives
  • Aralkylamine
  • Benzenoid
  • Piperidine
  • Pyrrole
  • Heteroaromatic compound
  • Tertiary aliphatic amine
  • Tertiary amine
  • Alkanolamine
  • Azacycle
  • Organoheterocyclic compound
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Amine
  • 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
logP2.84ALOGPS
logP3.23ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)13.32ChemAxon
pKa (Strongest Basic)7.04ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area28.4 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity88.46 m³·mol⁻¹ChemAxon
Polarizability34.74 ųChemAxon
Number of Rings5ChemAxon
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 IDC00001713
Chemspider ID390607
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound442066
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available