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Record Information
Version2.0
Created at2022-04-27 22:38:50 UTC
Updated at2022-04-27 22:38:50 UTC
NP-MRD IDNP0051263
Secondary Accession NumbersNone
Natural Product Identification
Common NameAphylline
Description17-Oxosparteine 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. Aphylline is found in Acosmium panamense, Anabasis aphylla, Apis cerana, Argyrolobium frutescens, Argyrolobium lanceolatum, Argyrolobium lunare, Argyrolobium rupestre, Argyrolobium sankeyi, Argyrolobium speciosum, Argyrolobium tomentosum, Argyrolobium velutinum, Cytisus monspessulanus L., Lupinus latifolius, Lupinus hartwegii, Sophora davidii, Sophora griffithii, Virgilia divaricata and Virgilia oroboides. Aphylline was first documented in 2011 (PMID: 22000488). Based on a literature review very few articles have been published on 17-Oxosparteine (PMID: 21760788).
Structure
Thumb
Synonyms
ValueSource
17-Oxosparteine monohydrochloride, (7R-(7alpha,7abeta,14alpha,14aalpha))-isomerMeSH
17-Oxosparteine, (7R-(7alpha,7abeta,14alpha,14aalpha))-isomerMeSH
17-Oxosparteine, 7S-(7alpha,7aalpha,14alpha,14abeta)-isomerMeSH
17-Oxosparteine, 7S-(7alpha,7beta,14alpha,14abeta)-isomerMeSH
Chemical FormulaC15H24N2O
Average Mass248.3700 Da
Monoisotopic Mass248.18886 Da
IUPAC Name(1S,2R,9S,10S)-7,15-diazatetracyclo[7.7.1.0^{2,7}.0^{10,15}]heptadecan-8-one
Traditional Name(1S,2R,9S,10S)-7,15-diazatetracyclo[7.7.1.0^{2,7}.0^{10,15}]heptadecan-8-one
CAS Registry NumberNot Available
SMILES
O=C1[C@H]2C[C@@H](CN3CCCC[C@@H]23)[C@H]2CCCCN12
InChI Identifier
InChI=1S/C15H24N2O/c18-15-12-9-11(13-5-2-4-8-17(13)15)10-16-7-3-1-6-14(12)16/h11-14H,1-10H2/t11-,12-,13+,14-/m0/s1
InChI KeyYQMWQSMYVPLYDI-FQUUOJAGSA-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
Acosmium panamensePlant
Anabasis aphyllaPlant
Apis ceranaLOTUS Database
Argyrolobium frutescensPlant
Argyrolobium lanceolatumPlant
Argyrolobium lunarePlant
Argyrolobium rupestrePlant
Argyrolobium sankeyiPlant
Argyrolobium speciosumPlant
Argyrolobium tomentosumPlant
Argyrolobium velutinumPlant
Cytisus monspessulanus L.Plant
Lupinus latifoliusPlant
Lupinus mexicanusPlant
Sophora davidiiPlant
Sophora griffithiiPlant
Virgilia divaricataPlant
Virgilia oroboidesPlant
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
  • Tertiary aliphatic amine
  • Tertiary amine
  • Amino acid or derivatives
  • Carboxamide group
  • Lactam
  • Organoheterocyclic compound
  • Azacycle
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organooxygen compound
  • Amine
  • Organic nitrogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Organic oxide
  • 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
logP2.5ALOGPS
logP1.37ChemAxon
logS-1.4ALOGPS
pKa (Strongest Basic)8.88ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area23.55 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity71.5 m³·mol⁻¹ChemAxon
Polarizability26.98 ųChemAxon
Number of Rings4ChemAxon
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 IDC00007692
Chemspider ID23327249
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound12306750
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Merghoub N, Benbacer L, El Btaouri H, Ait Benhassou H, Terryn C, Attaleb M, Madoulet C, Benjouad A, El Mzibri M, Morjani H, Amzazi S: In vitro antiproliferative effect and induction of apoptosis by Retama monosperma L. extract in human cervical cancer cells. Cell Mol Biol (Noisy-le-grand). 2011 Oct 15;57 Suppl:OL1581-91. doi: 10.5772/30025. [PubMed:22000488 ]
  2. Jasiewicz B, Wyrzykiewicz E: Mass Spectrometry of Bis-Quinolizidine Alkaloids: FAB-MS of Oxo-Substituted Sparteines. Int J Anal Chem. 2011;2011:652589. doi: 10.1155/2011/652589. Epub 2011 Jun 5. [PubMed:21760788 ]