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Record Information
Version2.0
Created at2022-04-27 22:39:19 UTC
Updated at2022-04-27 22:39:19 UTC
NP-MRD IDNP0051274
Secondary Accession NumbersNone
Natural Product Identification
Common Name(+)-13-Hydroxylupanine
Description(1R,2R,9R,10S,12S)-12-hydroxy-7,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]Heptadecan-6-one belongs to the class of organic compounds known as sparteine, lupanine, and related alkaloids. These are alkaloids with a structure based on either sparteine, lupanine, or derivatives thereof. These are tetracyclic compounds made of two fused quinolizidine ring systems. (+)-13-Hydroxylupanine is found in Brongniartia spp., Cadia spp., Calpurnia aurea subsp. aurea , Chamaecyparis absinthioides, Chamaecytisus austriacus , Cytisus scoparius , Genista cinerea, Genista majorica, Lupinus angustifolius cv.Fest , Lupinus exaltatus, Lupinus polyphyllus, Lupinus spp., Lupinus tassilicus, Lupinus wyethii, Priestleya spp., Templetonia biloba and Thermopsis cinerea. Based on a literature review very few articles have been published on (1R,2R,9R,10S,12S)-12-hydroxy-7,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]Heptadecan-6-one.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC15H24N2O2
Average Mass264.3690 Da
Monoisotopic Mass264.18378 Da
IUPAC Name(1R,2R,9R,10S,12S)-12-hydroxy-7,15-diazatetracyclo[7.7.1.0^{2,7}.0^{10,15}]heptadecan-6-one
Traditional Name(1R,2R,9R,10S,12S)-12-hydroxy-7,15-diazatetracyclo[7.7.1.0^{2,7}.0^{10,15}]heptadecan-6-one
CAS Registry NumberNot Available
SMILES
O[C@H]1CCN2C[C@H]3C[C@H](CN4[C@@H]3CCCC4=O)[C@@H]2C1
InChI Identifier
InChI=1S/C15H24N2O2/c18-12-4-5-16-8-10-6-11(14(16)7-12)9-17-13(10)2-1-3-15(17)19/h10-14,18H,1-9H2/t10-,11-,12+,13-,14+/m1/s1
InChI KeyJVYKIBAJVKEZSQ-RGDJUOJXSA-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
Brongniartia spp.Plant
Cadia spp.Plant
Calpurnia aurea subsp. aureaPlant
Chamaecyparis absinthioidesPlant
Chamaecytisus austriacusPlant
Cytisus scopariusPlant
Genista cinereaPlant
Genista majoricaPlant
Lupinus angustifolius cv.FestPlant
Lupinus exaltatusPlant
Lupinus polyphyllusLOTUS Database
Lupinus spp.Plant
Lupinus tassilicusPlant
Lupinus wyethiiPlant
Priestleya spp.Plant
Templetonia bilobaPlant
Thermopsis cinereaPlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as sparteine, lupanine, and related alkaloids. These are alkaloids with a structure based on either sparteine, lupanine, or derivatives thereof. These are tetracyclic compounds made of two fused quinolizidine ring systems.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassLupin alkaloids
Sub ClassSparteine, lupanine, and related alkaloids
Direct ParentSparteine, lupanine, and related alkaloids
Alternative Parents
Substituents
  • Sparteine-lupanine skeleton
  • Quinolizidinone
  • Quinolizidine
  • Delta-lactam
  • Piperidinone
  • Piperidine
  • Tertiary carboxylic acid amide
  • Amino acid or derivatives
  • Carboxamide group
  • Lactam
  • Secondary alcohol
  • Tertiary amine
  • Tertiary aliphatic amine
  • Carboxylic acid derivative
  • Azacycle
  • Organoheterocyclic compound
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Alcohol
  • Carbonyl group
  • 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
logP0.96ALOGPS
logP-0.46ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)15.17ChemAxon
pKa (Strongest Basic)9.23ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area43.78 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity73.03 m³·mol⁻¹ChemAxon
Polarizability29.59 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
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 Compound12310677
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available