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Record Information
Version2.0
Created at2022-04-27 22:16:01 UTC
Updated at2022-04-27 22:16:02 UTC
NP-MRD IDNP0050858
Secondary Accession NumbersNone
Natural Product Identification
Common NameEburnamonine
DescriptionVinburnine, also known as cervoxan, 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. Eburnamonine is found in Aspidosperma quebracho-blanco, Hunteria congolana, Hunteria eburnea Pichon., Hunteria umbellata, Hunteria zeylanica, Kopsia griffithii, Kopsia officinalis, Kopsia pauciflora, Rauvolfia serpentina, Strempeliopsis strempelioides, Viburnum rhytidophyllum and Vinca minor . Vinburnine is a very strong basic compound (based on its pKa).
Structure
Thumb
Synonyms
ValueSource
CervoxanKegg
(-)-EburnamonineMeSH
Eburnamonine phosphate, (3alpha,16alpha)-isomerMeSH
EburnamonineMeSH
Eburnamonine monohydrochloride, (3alpha,16alpha)-isomerMeSH
Eburnamonine, (3alpha,16alpha)-isomerMeSH
Chemical FormulaC19H22N2O
Average Mass294.3980 Da
Monoisotopic Mass294.17321 Da
IUPAC Name(15S,19S)-15-ethyl-1,11-diazapentacyclo[9.6.2.0²,⁷.0⁸,¹⁸.0¹⁵,¹⁹]nonadeca-2,4,6,8(18)-tetraen-17-one
Traditional Namevinburnine
CAS Registry NumberNot Available
SMILES
[H][C@]12N3CCC[C@@]1(CC)CC(=O)N1C4=CC=CC=C4C(CC3)=C21
InChI Identifier
InChI=1S/C19H22N2O/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/h3-4,6-7,18H,2,5,8-12H2,1H3/t18-,19+/m1/s1
InChI KeyWYJAPUKIYAZSEM-MOPGFXCFSA-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
Aspidosperma quebracho-blancoLOTUS Database
Hunteria congolanaLOTUS Database
Hunteria eburnea Pichon.Plant
Hunteria umbellataLOTUS Database
Hunteria zeylanicaLOTUS Database
Kopsia griffithiiLOTUS Database
Kopsia officinalisLOTUS Database
Kopsia paucifloraLOTUS Database
Rauvolfia serpentinaLOTUS Database
Strempeliopsis strempelioidesLOTUS Database
Viburnum rhytidophyllumLOTUS 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
  • Piperidine
  • Benzenoid
  • Heteroaromatic compound
  • Pyrrole
  • Tertiary amine
  • Lactam
  • Tertiary aliphatic amine
  • Azacycle
  • Organoheterocyclic compound
  • Amine
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
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
logP3.3ALOGPS
logP2.74ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)19.25ChemAxon
pKa (Strongest Basic)6.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area25.24 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity87.05 m³·mol⁻¹ChemAxon
Polarizability33.67 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDDB13793
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00001714
Chemspider IDNot Available
KEGG Compound IDC09149
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkVinburnine
METLIN IDNot Available
PubChem Compound71203
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available