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Record Information
Version1.0
Created at2022-09-12 08:10:00 UTC
Updated at2022-09-12 08:10:01 UTC
NP-MRD IDNP0326528
Secondary Accession NumbersNone
Natural Product Identification
Common Name4,5,14-trimethoxy-9-azatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-2(7),3,5,12-tetraen-15-ol
DescriptionGALANTHINE belongs to the class of organic compounds known as phenanthridines and derivatives. These are polycyclic compounds containing a phenanthridine moiety, which is a tricyclic system with two benzene rings joined by a pyridine forming a non-linear skeleton. Hydrogenated derivatives are also included. 4,5,14-trimethoxy-9-azatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-2(7),3,5,12-tetraen-15-ol is found in Crinum amabile, Galanthus elwesii, Hippeastrum puniceum, Lycoris incarnata, Lycoris sanguinea, Narcissus papyraceus, Habranthus brachyandrus and Zephyranthes citrina. It was first documented in 2013 (PMID: 23513717). Based on a literature review a small amount of articles have been published on GALANTHINE (PMID: 35483192) (PMID: 28808407) (PMID: 25115079) (PMID: 35953692).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC18H23NO4
Average Mass317.3850 Da
Monoisotopic Mass317.16271 Da
IUPAC Name4,5,14-trimethoxy-9-azatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-2(7),3,5,12-tetraen-15-ol
Traditional Name4,5,14-trimethoxy-9-azatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-2(7),3,5,12-tetraen-15-ol
CAS Registry NumberNot Available
SMILES
COC1C=C2CCN3CC4=C(C=C(OC)C(OC)=C4)C(C23)C1O
InChI Identifier
InChI=1S/C18H23NO4/c1-21-13-7-11-9-19-5-4-10-6-15(23-3)18(20)16(17(10)19)12(11)8-14(13)22-2/h6-8,15-18,20H,4-5,9H2,1-3H3
InChI KeyVOIMPDXOQJYVDI-UHFFFAOYSA-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
Crinum amabileLOTUS Database
Galanthus elwesiiLOTUS Database
Hippeastrum puniceumLOTUS Database
Lycoris incarnataLOTUS Database
Lycoris sanguineaLOTUS Database
Narcissus papyraceusLOTUS Database
Zephyranthes brachyandraLOTUS Database
Zephyranthes citrinaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenanthridines and derivatives. These are polycyclic compounds containing a phenanthridine moiety, which is a tricyclic system with two benzene rings joined by a pyridine forming a non-linear skeleton. Hydrogenated derivatives are also included.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassQuinolines and derivatives
Sub ClassBenzoquinolines
Direct ParentPhenanthridines and derivatives
Alternative Parents
Substituents
  • Phenanthridine
  • Tetrahydroisoquinoline
  • Indole or derivatives
  • Anisole
  • Alkyl aryl ether
  • Aralkylamine
  • Benzenoid
  • N-alkylpyrrolidine
  • Pyrrolidine
  • Secondary alcohol
  • Tertiary amine
  • Tertiary aliphatic amine
  • Azacycle
  • Ether
  • Dialkyl ether
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Alcohol
  • Organic nitrogen 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
logP0.87ChemAxon
pKa (Strongest Acidic)13.72ChemAxon
pKa (Strongest Basic)8.11ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area51.16 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity88.09 m³·mol⁻¹ChemAxon
Polarizability35 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 IDC00024390
Chemspider ID87838
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound97315
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Sierra K, de Andrade JP, R Tallini L, Osorio EH, Yanez O, Osorio MI, Oleas NH, Garcia-Beltran O, de S Borges W, Bastida J, Osorio E, Cortes N: In vitro and in silico analysis of galanthine from Zephyranthes carinata as an inhibitor of acetylcholinesterase. Biomed Pharmacother. 2022 Jun;150:113016. doi: 10.1016/j.biopha.2022.113016. Epub 2022 Apr 25. [PubMed:35483192 ]
  2. Gasparini LS, Macedo ND, Pimentel EF, Fronza M, Junior VL, Borges WS, Cole ER, Andrade TU, Endringer DC, Lenz D: In vitro Cell Viability by CellProfiler((R)) Software as Equivalent to MTT Assay. Pharmacogn Mag. 2017 Jul;13(Suppl 2):S365-S369. doi: 10.4103/0973-1296.210176. Epub 2017 Jul 11. [PubMed:28808407 ]
  3. Safratova M, Novak Z, Kulhankova A, Kunes J, Hrabinova M, Jun D, Macakova K, Opletal L, Cahlikova L: Revised NMR data for 9-O-demethylgalanthine: an alkaloid from Zephyranthes robusta (Amaryllidaceae) and its biological activity. Nat Prod Commun. 2014 Jun;9(6):787-8. [PubMed:25115079 ]
  4. Katoch D, Kumar D, Sharma U, Kumar N, Padwad YS, Lal B, Singh B: Zephgrabetaine: a new betaine-type amaryllidaceae alkaloid from Zephyranthes grandiflora. Nat Prod Commun. 2013 Feb;8(2):161-4. [PubMed:23513717 ]
  5. Ptak A, Moranska E, Warchol M, Gurgul A, Skrzypek E, Dziurka M, Laurain-Mattar D, Spina R, Jaglarz A, Simlat M: Endophytic bacteria from in vitro culture of Leucojum aestivum L. a new source of galanthamine and elicitor of alkaloid biosynthesis. Sci Rep. 2022 Aug 11;12(1):13700. doi: 10.1038/s41598-022-17992-5. [PubMed:35953692 ]
  6. LOTUS database [Link]