Record Information |
---|
Version | 1.0 |
---|
Created at | 2022-09-12 08:10:00 UTC |
---|
Updated at | 2022-09-12 08:10:01 UTC |
---|
NP-MRD ID | NP0326528 |
---|
Secondary Accession Numbers | None |
---|
Natural Product Identification |
---|
Common Name | 4,5,14-trimethoxy-9-azatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-2(7),3,5,12-tetraen-15-ol |
---|
Description | GALANTHINE 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 | COC1C=C2CCN3CC4=C(C=C(OC)C(OC)=C4)C(C23)C1O 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 |
---|
Synonyms | Not Available |
---|
Chemical Formula | C18H23NO4 |
---|
Average Mass | 317.3850 Da |
---|
Monoisotopic Mass | 317.16271 Da |
---|
IUPAC Name | 4,5,14-trimethoxy-9-azatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-2(7),3,5,12-tetraen-15-ol |
---|
Traditional Name | 4,5,14-trimethoxy-9-azatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-2(7),3,5,12-tetraen-15-ol |
---|
CAS Registry Number | Not 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 Key | VOIMPDXOQJYVDI-UHFFFAOYSA-N |
---|
Experimental Spectra |
---|
|
| Not Available | Predicted Spectra |
---|
|
| Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
---|
1D NMR | 13C NMR Spectrum (1D, 25 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Chemical Shift Submissions |
---|
|
| Not Available | Species |
---|
Species of Origin | |
---|
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. |
---|
Kingdom | Organic compounds |
---|
Super Class | Organoheterocyclic compounds |
---|
Class | Quinolines and derivatives |
---|
Sub Class | Benzoquinolines |
---|
Direct Parent | Phenanthridines 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 Framework | Aromatic heteropolycyclic compounds |
---|
External Descriptors | Not Available |
---|
Physical Properties |
---|
State | Not Available |
---|
Experimental Properties | Property | Value | Reference |
---|
Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
|
---|
Predicted Properties | |
---|
General References | - 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- LOTUS database [Link]
|
---|