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Record Information
Version2.0
Created at2022-05-30 16:47:32 UTC
Updated at2024-09-03 04:20:09 UTC
NP-MRD IDNP0137279
Natural Product DOIhttps://doi.org/10.57994/2001
Secondary Accession NumbersNone
Natural Product Identification
Common NameLycorine
Description5,7-Dioxa-12-azapentacyclo[10.6.1.0²,¹⁰.0⁴,⁸.0¹⁵,¹⁹]Nonadeca-2,4(8),9,15-tetraene-17,18-diol belongs to the class of organic compounds known as lycorine-type amaryllidaceae alkaloids. These are amaryllidaceae alkaloids compounds containing the lycorine skeleton, made up of a pyrrolo[d,e]phenanthridine ring system. Lycorine is found in Crinum amabile, Crinum asiaticum, Crinum bulbispermum, Crinum kirkii, Crinum latifolium, Crinum yemense, Hippeastrum vittatum, Hymenocallis rotata, Imperata cylindrica, Leucojum vernum, Lycoris sanguinea and Zephyranthes candida. 5,7-Dioxa-12-azapentacyclo[10.6.1.0²,¹⁰.0⁴,⁸.0¹⁵,¹⁹]Nonadeca-2,4(8),9,15-tetraene-17,18-diol is a very strong basic compound (based on its pKa).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC16H17NO4
Average Mass287.3150 Da
Monoisotopic Mass287.11576 Da
IUPAC Name5,7-dioxa-12-azapentacyclo[10.6.1.0²,¹⁰.0⁴,⁸.0¹⁵,¹⁹]nonadeca-2,4(8),9,15-tetraene-17,18-diol
Traditional Namelycorine
CAS Registry NumberNot Available
SMILES
OC1C=C2CCN3CC4=CC5=C(OCO5)C=C4C(C23)C1O
InChI Identifier
InChI=1S/C16H17NO4/c18-11-3-8-1-2-17-6-9-4-12-13(21-7-20-12)5-10(9)14(15(8)17)16(11)19/h3-5,11,14-16,18-19H,1-2,6-7H2
InChI KeyXGVJWXAYKUHDOO-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
COSY NMR[1H, 1H] NMR Spectrum (2D, 400 MHz, CDCl3, experimental)luis.guerrero@unige.chUniversity of GenevaLuis Quiros-Guerrero, PhD2024-03-28View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)luis.guerrero@unige.chUniversity of GenevaLuis Quiros-Guerrero, PhD2024-03-28View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, CDCl3, experimental)luis.guerrero@unige.chUniversity of GenevaLuis Quiros-Guerrero, PhD2024-03-28View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)luis.guerrero@unige.chUniversity of GenevaLuis Quiros-Guerrero, PhD2024-03-28View Spectrum
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
Crinum amabileLOTUS Database
Crinum asiaticumLOTUS Database
Crinum bulbispermumLOTUS Database
Crinum erubescens
      Not Available
Crinum kirkiiLOTUS Database
Crinum latifoliumLOTUS Database
Crinum yemenseLOTUS Database
Hippeastrum vittatumLOTUS Database
Hymenocallis rotataLOTUS Database
Imperata cylindricaLOTUS Database
Leucojum vernumLOTUS Database
Lycoris sanguineaLOTUS Database
Zephyranthes candidaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as lycorine-type amaryllidaceae alkaloids. These are amaryllidaceae alkaloids compounds containing the lycorine skeleton, made up of a pyrrolo[d,e]phenanthridine ring system.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassAmaryllidaceae alkaloids
Sub ClassLycorine-type amaryllidaceae alkaloids
Direct ParentLycorine-type amaryllidaceae alkaloids
Alternative Parents
Substituents
  • Lycorine skeleton
  • Benzoquinoline
  • Phenanthridine
  • Quinoline
  • Tetrahydroisoquinoline
  • Benzodioxole
  • Indole or derivatives
  • Aralkylamine
  • Benzenoid
  • N-alkylpyrrolidine
  • Pyrrolidine
  • Tertiary aliphatic amine
  • Tertiary amine
  • Secondary alcohol
  • 1,2-diol
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Acetal
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organooxygen compound
  • Organic nitrogen compound
  • Organic oxygen compound
  • Amine
  • Alcohol
  • Organopnictogen compound
  • 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
logP0.01ALOGPS
logP0.16ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)13.46ChemAxon
pKa (Strongest Basic)7.62ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area62.16 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity76.18 m³·mol⁻¹ChemAxon
Polarizability30.25 ųChemAxon
Number of Rings5ChemAxon
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 Compound3978
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References