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Record Information
Version2.0
Created at2022-04-28 11:00:26 UTC
Updated at2022-04-28 11:00:26 UTC
NP-MRD IDNP0066769
Secondary Accession NumbersNone
Natural Product Identification
Common Name1,2-Dihydrogalanthamine
DescriptionLycoramine, also known as (+-)-lycoramine, belongs to the class of organic compounds known as galanthamine-type amaryllidaceae alkaloids. These are amaryllidaceae alkaloids with a structure characterized a tetracyclic skeleton with two ortho aromatic protons in ring A. 1,2-Dihydrogalanthamine is found in Brunsvigia gregaria, Hymenocallis littoralis, Hymenocallis rotata, Lycoris aurea , Lycoris guangxiensis, Lycoris incarnata, Lycoris longituba, Lycoris radiata, Lycoris radiata Herb. , Lycoris sanguinea, Lycoris sanguinea Maxim, Lycoris squamigera, Lycoris traubii, Narcissus papyraceus Kerl-Gawl, Narcissus pseudonarcissus subsp.pseudonarcissus, Narcissus tazetta L. and Pancratium maritimum. 1,2-Dihydrogalanthamine was first documented in 2021 (PMID: 33434626). Based on a literature review a small amount of articles have been published on Lycoramine (PMID: 35483192) (PMID: 34874174) (PMID: 34659286) (PMID: 33200692).
Structure
Thumb
Synonyms
ValueSource
1,2-DihydrogalanthamineKegg
(+-)-LycoramineMeSH
Chemical FormulaC17H23NO3
Average Mass289.3750 Da
Monoisotopic Mass289.16779 Da
IUPAC Name(1R,12S,14S)-9-methoxy-4-methyl-11-oxa-4-azatetracyclo[8.6.1.0^{1,12}.0^{6,17}]heptadeca-6(17),7,9-trien-14-ol
Traditional Name(1R,12S,14S)-9-methoxy-4-methyl-11-oxa-4-azatetracyclo[8.6.1.0^{1,12}.0^{6,17}]heptadeca-6(17),7,9-trien-14-ol
CAS Registry NumberNot Available
SMILES
COC1=C2O[C@H]3C[C@@H](O)CC[C@]33CCN(C)CC(C=C1)=C23
InChI Identifier
InChI=1S/C17H23NO3/c1-18-8-7-17-6-5-12(19)9-14(17)21-16-13(20-2)4-3-11(10-18)15(16)17/h3-4,12,14,19H,5-10H2,1-2H3/t12-,14-,17-/m0/s1
InChI KeyGJRMHIXYLGOZSE-JDFRZJQESA-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
Brunsvigia gregariaPlant
Hymenocallis littoralisLOTUS Database
Hymenocallis rotataLOTUS Database
Lycoris aureaPlant
Lycoris guangxiensisPlant
Lycoris incarnataLOTUS Database
Lycoris longitubaPlant
Lycoris radiataLOTUS Database
Lycoris radiata Herb.Plant
Lycoris sanguineaLOTUS Database
Lycoris sanguinea MaximPlant
Lycoris squamigeraLOTUS Database
Lycoris traubiiLOTUS Database
Narcissus papyraceus Kerl-GawlPlant
Narcissus pseudonarcissus subsp.pseudonarcissusPlant
Narcissus tazettaPlant
Pancratium maritimumLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as galanthamine-type amaryllidaceae alkaloids. These are amaryllidaceae alkaloids with a structure characterized a tetracyclic skeleton with two ortho aromatic protons in ring A.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassAmaryllidaceae alkaloids
Sub ClassGalanthamine-type amaryllidaceae alkaloids
Direct ParentGalanthamine-type amaryllidaceae alkaloids
Alternative Parents
Substituents
  • Galanthamine-type amaryllidaceae alkaloid
  • Benzazepine
  • Coumaran
  • Anisole
  • Alkyl aryl ether
  • Azepine
  • Aralkylamine
  • Benzenoid
  • Cyclic alcohol
  • Secondary alcohol
  • Tertiary amine
  • Tertiary aliphatic amine
  • Ether
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Organic nitrogen compound
  • Alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxygen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
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
logP1.62ALOGPS
logP1.37ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)15.17ChemAxon
pKa (Strongest Basic)8.61ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area41.93 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity81.34 m³·mol⁻¹ChemAxon
Polarizability32.23 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 IDC00024405
Chemspider ID391833
KEGG Compound IDC12233
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound443723
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Aleya F, Xianmin C, Anthony H, Meriel J: Relative expression of putative genes involved in galanthamine and other Amaryllidaceae alkaloids biosynthesis in Narcissus field and in vitro tissues. Gene. 2021 Mar 30;774:145424. doi: 10.1016/j.gene.2021.145424. Epub 2021 Jan 9. [PubMed:33434626 ]
  2. 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 ]
  3. Chang YP, Ma X, Shao H, Zhao YM: Total Syntheses of Galanthamine and Lycoramine via a Palladium-Catalyzed Cascade Cyclization and Late-Stage Reorganization of the Cyclized Skeleton. Org Lett. 2021 Dec 17;23(24):9659-9663. doi: 10.1021/acs.orglett.1c03943. Epub 2021 Dec 7. [PubMed:34874174 ]
  4. Li Q, Xu J, Zheng Y, Zhang Y, Cai Y: Transcriptomic and Metabolomic Analyses Reveals That Exogenous Methyl Jasmonate Regulates Galanthamine Biosynthesis in Lycoris longituba Seedlings. Front Plant Sci. 2021 Sep 30;12:713795. doi: 10.3389/fpls.2021.713795. eCollection 2021. [PubMed:34659286 ]
  5. Kiris I, Basar MK, Sahin B, Gurel B, Coskun J, Mroczek T, Baykal AT: Evaluation of the Therapeutic Effect of Lycoramine on Alzheimer's Disease in Mouse Model. Curr Med Chem. 2021;28(17):3449-3473. doi: 10.2174/0929867327999201116193126. [PubMed:33200692 ]