Lycorine
(right click,save link as to download,it is a temp file,please download as soon as possible, you can also use CTRL+S to save the whole html page)
Basic Info
| Common Name | Lycorine(F05212) |
| 2D Structure | |
| Description | Lycorine is a toxic crystalline alkaloid found in various Amaryllidaceae species, such as the cultivated bush lily (Clivia miniata), surprise lilies (Lycoris), and daffodils (Narcissus). It may be highly poisonous, or even lethal, when ingested in certain quantities. Symptoms of lycorine toxicity are vomiting, diarrhea, and convulsions. Lycorine, definition at mercksource.com Regardless, it is sometimes used medicinally, a reason why some groups may harvest the very popular Clivia miniata. |
| FRCD ID | F05212 |
| CAS Number | 476-28-8 |
| PubChem CID | 72378 |
| Formula | C16H17NO4 |
| IUPAC Name | None |
| InChI Key | XGVJWXAYKUHDOO-DANNLKNASA-N |
| InChI | 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/t11-,14-,15+,16+/m0/s1 |
| Canonical SMILES | C1CN2CC3=CC4=C(C=C3C5C2C1=CC(C5O)O)OCO4 |
| Isomeric SMILES | C1CN2CC3=CC4=C(C=C3[C@H]5[C@H]2C1=C[C@@H]([C@H]5O)O)OCO4 |
| Synonyms |
EINECS 207-503-6
lycorine
Galanthidine
Amarylline
Narcissine
476-28-8
Licorine
(-)-Lycorine
Lycorine hydrochloride
UNII-I9Q105R5BU
|
| Classifies |
Plant Toxin
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Alkaloids and derivatives |
| Class | Amaryllidaceae alkaloids |
| Subclass | Lycorine-type amaryllidaceae alkaloids |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Lycorine-type amaryllidaceae alkaloids |
| Alternative Parents | |
| Molecular Framework | Aromatic heteropolycyclic compounds |
| 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 |
| Description | This compound 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. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 287.315 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 0 |
| Complexity | 481 |
| Monoisotopic Mass | 287.116 |
| Exact Mass | 287.116 |
| XLogP | 0 |
| Formal Charge | 0 |
| Heavy Atom Count | 21 |
| Defined Atom Stereocenter Count | 4 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.7291 |
| Human Intestinal Absorption | HIA+ | 0.7448 |
| Caco-2 Permeability | Caco2+ | 0.5524 |
| P-glycoprotein Substrate | Substrate | 0.7452 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.8491 |
| Non-inhibitor | 0.9901 | |
| Renal Organic Cation Transporter | Inhibitor | 0.5631 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.7532 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.9048 |
| CYP450 2D6 Substrate | Non-substrate | 0.7161 |
| CYP450 3A4 Substrate | Substrate | 0.5875 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.9106 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9071 |
| CYP450 2D6 Inhibitor | Inhibitor | 0.8933 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.9025 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.8309 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.7607 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Strong inhibitor | 0.5139 |
| Non-inhibitor | 0.7248 | |
| AMES Toxicity | Non AMES toxic | 0.7586 |
| Carcinogens | Non-carcinogens | 0.9618 |
| Fish Toxicity | High FHMT | 0.9792 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.8357 |
| Honey Bee Toxicity | Low HBT | 0.5217 |
| Biodegradation | Not ready biodegradable | 0.9080 |
| Acute Oral Toxicity | III | 0.5320 |
| Carcinogenicity (Three-class) | Non-required | 0.5181 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -2.6892 | LogS |
| Caco-2 Permeability | 0.4129 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.8329 | LD50, mol/kg |
| Fish Toxicity | 1.0592 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.4040 | pIGC50, ug/L |
Targets
- General Function:
- Serine hydrolase activity
- Specific Function:
- Terminates signal transduction at the neuromuscular junction by rapid hydrolysis of the acetylcholine released into the synaptic cleft. Role in neuronal apoptosis.
- Gene Name:
- ACHE
- Uniprot ID:
- P22303
- Molecular Weight:
- 67795.525 Da
References
- Wang YH, Zhang ZK, Yang FM, Sun QY, He HP, Di YT, Mu SZ, Lu Y, Chang Y, Zheng QT, Ding M, Dong JH, Hao XJ: Benzylphenethylamine alkaloids from Hosta plantaginea with inhibitory activity against tobacco mosaic virus and acetylcholinesterase. J Nat Prod. 2007 Sep;70(9):1458-61. Epub 2007 Sep 7. [17822295 ]