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Record Information
Version2.0
Created at2022-09-05 21:15:07 UTC
Updated at2022-09-05 21:15:07 UTC
NP-MRD IDNP0220051
Secondary Accession NumbersNone
Natural Product Identification
Common Name[(1s,14r,15z)-15-ethylidene-3-methyl-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraen-13-yl]methanol
DescriptionAffinisine belongs to the class of organic compounds known as macroline alkaloids. These are alkaloids with a structure that is based on the tetracyclic macroline skeleton. The macroline skeleton arises by scission of the C-21 to N-4 bond of the akuammilan skeleton, and mostly occurs in bisindole alkaloids. [(1s,14r,15z)-15-ethylidene-3-methyl-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraen-13-yl]methanol is found in Alstonia angustifolia, Tabernaemontana catharinensis, Tabernaemontana corymbosa, Tabernaemontana cymosa, Tabernaemontana heterophylla, Tabernaemontana hystrix and Tabernaemontana vanheurckii. Based on a literature review very few articles have been published on Affinisine.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC20H24N2O
Average Mass308.4250 Da
Monoisotopic Mass308.18886 Da
IUPAC Name[(1S,14R,15Z)-15-ethylidene-3-methyl-3,17-diazapentacyclo[12.3.1.0^{2,10}.0^{4,9}.0^{12,17}]octadeca-2(10),4,6,8-tetraen-13-yl]methanol
Traditional Name[(1S,14R,15Z)-15-ethylidene-3-methyl-3,17-diazapentacyclo[12.3.1.0^{2,10}.0^{4,9}.0^{12,17}]octadeca-2(10),4,6,8-tetraen-13-yl]methanol
CAS Registry NumberNot Available
SMILES
C\C=C1/CN2C3CC4=C([C@@H]2C[C@@H]1C3CO)N(C)C1=CC=CC=C41
InChI Identifier
InChI=1S/C20H24N2O/c1-3-12-10-22-18-9-15-13-6-4-5-7-17(13)21(2)20(15)19(22)8-14(12)16(18)11-23/h3-7,14,16,18-19,23H,8-11H2,1-2H3/b12-3+/t14-,16?,18?,19-/m0/s1
InChI KeyUVWQYWHKTZABSO-ALCFZQKKSA-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
Alstonia angustifoliaLOTUS Database
Tabernaemontana catharinensisLOTUS Database
Tabernaemontana corymbosaLOTUS Database
Tabernaemontana cymosaLOTUS Database
Tabernaemontana heterophyllaLOTUS Database
Tabernaemontana hystrixLOTUS Database
Tabernaemontana vanheurckiiLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as macroline alkaloids. These are alkaloids with a structure that is based on the tetracyclic macroline skeleton. The macroline skeleton arises by scission of the C-21 to N-4 bond of the akuammilan skeleton, and mostly occurs in bisindole alkaloids.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassMacroline alkaloids
Sub ClassNot Available
Direct ParentMacroline alkaloids
Alternative Parents
Substituents
  • Macroline skeleton
  • Sarpagine-skeleton
  • Vobasan skeleton
  • Beta-carboline
  • Pyridoindole
  • N-alkylindole
  • 3-alkylindole
  • Indole
  • Indole or derivatives
  • Quinuclidine
  • Aralkylamine
  • Benzenoid
  • N-methylpyrrole
  • Piperidine
  • Substituted pyrrole
  • Pyrrole
  • 1,3-aminoalcohol
  • Heteroaromatic compound
  • Tertiary amine
  • Tertiary aliphatic amine
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organic oxygen 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
logP2.43ChemAxon
pKa (Strongest Acidic)15.4ChemAxon
pKa (Strongest Basic)6.64ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area28.4 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity94.22 m³·mol⁻¹ChemAxon
Polarizability36.18 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 IDC00001676
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAffinisine
METLIN IDNot Available
PubChem Compound101286222
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]