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Record Information
Version2.0
Created at2021-06-21 00:04:03 UTC
Updated at2021-06-30 00:17:26 UTC
NP-MRD IDNP0042390
Secondary Accession NumbersNone
Natural Product Identification
Common Name5R,8R-O-acetylfawcettiine
Provided ByJEOL DatabaseJEOL Logo
Description(1R,2R,10S,11R,13S,14R,15S)-14-(acetyloxy)-15-methyl-6-azatetracyclo[8.6.0.0¹,⁶.0²,¹³]Hexadecan-11-yl acetate belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. 5R,8R-O-acetylfawcettiine is found in Austrolycopodium magellanicum, Diphasiastrum alpinum, Lycopodium clavatum , Lycopodium contiguum, Lycopodium fawcettii, Lycopodium magellanicum, Lycopodium thyoides, Lycopodium saururus and Lycopodium annotinum. 5R,8R-O-acetylfawcettiine was first documented in 2013 (Halldorsdottir, E. S., et al.). Based on a literature review very few articles have been published on (1R,2R,10S,11R,13S,14R,15S)-14-(acetyloxy)-15-methyl-6-azatetracyclo[8.6.0.0¹,⁶.0²,¹³]Hexadecan-11-yl acetate.
Structure
Thumb
Synonyms
ValueSource
(1R,2R,10S,11R,13S,14R,15S)-14-(Acetyloxy)-15-methyl-6-azatetracyclo[8.6.0.0,.0,]hexadecan-11-yl acetic acidGenerator
Chemical FormulaC20H31NO4
Average Mass349.4710 Da
Monoisotopic Mass349.22531 Da
IUPAC Name(1R,2R,10S,11R,13S,14R,15S)-14-(acetyloxy)-15-methyl-6-azatetracyclo[8.6.0.0^{1,6}.0^{2,13}]hexadecan-11-yl acetate
Traditional Name(1R,2R,10S,11R,13S,14R,15S)-14-(acetyloxy)-15-methyl-6-azatetracyclo[8.6.0.0^{1,6}.0^{2,13}]hexadecan-11-yl acetate
CAS Registry NumberNot Available
SMILES
[H]C([H])([H])C(=O)O[C@]1([H])C([H])([H])[C@]2([H])[C@]([H])(OC(=O)C([H])([H])[H])[C@@]([H])(C([H])([H])[H])C([H])([H])[C@]34N(C([H])([H])C([H])([H])C([H])([H])[C@]13[H])C([H])([H])C([H])([H])C([H])([H])[C@]24[H]
InChI Identifier
InChI=1S/C20H31NO4/c1-12-11-20-16-6-4-8-21(20)9-5-7-17(20)18(24-13(2)22)10-15(16)19(12)25-14(3)23/h12,15-19H,4-11H2,1-3H3/t12-,15-,16+,17+,18+,19+,20+/m0/s1
InChI KeyDTMAAKPCEFYPNL-SNVZJSGSSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 400 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 100 MHz, chcl3, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 125 MHz, chcl3, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 150 MHz, chcl3, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 175 MHz, chcl3, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, chcl3, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 225 MHz, chcl3, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 25 MHz, chcl3, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 250 MHz, chcl3, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, chcl3, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, chcl3, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, chcl3, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, chcl3, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, chcl3, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, chcl3, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, chcl3, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, chcl3, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, chcl3, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, chcl3, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, chcl3, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, chcl3, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Austrolycopodium magellanicumLOTUS Database
Diphasiastrum alpinumJEOL database
    • Halldorsdottir, E. S., et al, Phytochem. Lett. 6, 355 (2013)
Lycopodium clavatumPlant
Lycopodium contiguumPlant
Lycopodium fawcettiiPlant
Lycopodium magellanicumPlant
Lycopodium thyoidesPlant
Phlegmariurus saururusPlant
Spinulum annotinumPlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentSesquiterpenoids
Alternative Parents
Substituents
  • Sesquiterpenoid
  • Azaspirodecane
  • Quinolizidine
  • Quinolidine
  • Dicarboxylic acid or derivatives
  • Piperidine
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Tertiary aliphatic amine
  • Tertiary amine
  • Carboxylic acid derivative
  • Azacycle
  • Organoheterocyclic compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Amine
  • Organic nitrogen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic 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
logP2.56ALOGPS
logP1.88ChemAxon
logS-3.4ALOGPS
pKa (Strongest Basic)8.52ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area55.84 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity93.53 m³·mol⁻¹ChemAxon
Polarizability38.48 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 IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound46197932
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Halldorsdottir, E. S., et al. (2013). Halldorsdottir, E. S., et al, Phytochem. Lett. 6, 355 (2013). Phytochem..