Ryanodine
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Basic Info
| Common Name | Ryanodine(F05214) |
| 2D Structure | |
| Description | Ryanodine is a poisonous alkaloid found in the South American plant Ryania speciosa (Flacourtiaceae). It was originally used as an insecticide. The compound has extremely high affinity to the open-form ryanodine receptor, a group of calcium channels found in skeletal muscle, smooth muscle, and heart muscle cells. It binds with such high affinity to the receptor that it was used as a label for the first purification of that class of ion channels and gave its name to it. |
| FRCD ID | F05214 |
| CAS Number | 15662-33-6 |
| PubChem CID | 441753 |
| Formula | C25H35NO9 |
| IUPAC Name | None |
| InChI Key | JJSYXNQGLHBRRK-YSOSZROBSA-N |
| InChI | InChI=1S/C25H35NO9/c1-12(2)22(31)17(34-16(28)14-7-6-10-26-14)23(32)18(4)11-21(30)19(22,5)25(23,33)24(35-21)15(27)13(3)8-9-20(18,24)29/h6-7,10,12-13,15,17,26-27,29-33H,8-9,11H2,1-5H3/t13-,15+,17+,18-,19-,20-,21-,22+,23+,24+,25+/m0/s1 |
| Canonical SMILES | CC1CCC2(C3(CC4(C5(C(C(C3(C5(C2(C1O)O4)O)O)OC(=O)C6=CC=CN6)(C(C)C)O)C)O)C)O |
| Isomeric SMILES | C[C@H]1CC[C@@]2([C@@]3(C[C@]4([C@]5([C@]([C@H]([C@@]3([C@]5([C@]2([C@@H]1O)O4)O)O)OC(=O)C6=CC=CN6)(C(C)C)O)C)O)C)O |
| Synonyms |
ryanodine
UNII-37H6ATE4SA
Ryania
37H6ATE4SA
Ryanexel
Ryanicide
Bonide ryatox
Ryania powder
Ryania speciosa
Ryania [ISO]
|
| Classifies |
Plant Toxin
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Lipids and lipid-like molecules |
| Class | Prenol lipids |
| Subclass | Diterpenoids |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Diterpenoids |
| Alternative Parents |
|
| Molecular Framework | Aromatic heteropolycyclic compounds |
| Substituents | Diterpenoid - Ryanodane diterpenoid - Pyrrole-2-carboxylic acid or derivatives - Oxepane - Monosaccharide - Oxane - Substituted pyrrole - Cyclic alcohol - Heteroaromatic compound - Pyrrole - Tetrahydrofuran - Tertiary alcohol - Carboxylic acid ester - Hemiacetal - Secondary alcohol - Polyol - Oxacycle - Monocarboxylic acid or derivatives - Azacycle - Organoheterocyclic compound - Carboxylic acid derivative - Hydrocarbon derivative - Organooxygen compound - Organonitrogen compound - Organic oxide - Organopnictogen compound - Organic oxygen compound - Organic nitrogen compound - Alcohol - Aromatic heteropolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 493.553 |
| Hydrogen Bond Donor Count | 7 |
| Hydrogen Bond Acceptor Count | 9 |
| Rotatable Bond Count | 4 |
| Complexity | 1010 |
| Monoisotopic Mass | 493.231 |
| Exact Mass | 493.231 |
| XLogP | -0.5 |
| Formal Charge | 0 |
| Heavy Atom Count | 35 |
| Defined Atom Stereocenter Count | 11 |
| 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- | 0.6624 |
| Human Intestinal Absorption | HIA+ | 0.9398 |
| Caco-2 Permeability | Caco2- | 0.7391 |
| P-glycoprotein Substrate | Substrate | 0.8417 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.6330 |
| Non-inhibitor | 0.7957 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.9026 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.4290 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8035 |
| CYP450 2D6 Substrate | Non-substrate | 0.7821 |
| CYP450 3A4 Substrate | Substrate | 0.7053 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.9046 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9071 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9329 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.9026 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.8647 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.8748 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9933 |
| Non-inhibitor | 0.7601 | |
| AMES Toxicity | Non AMES toxic | 0.6635 |
| Carcinogens | Non-carcinogens | 0.9714 |
| Fish Toxicity | High FHMT | 0.9954 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9962 |
| Honey Bee Toxicity | High HBT | 0.6267 |
| Biodegradation | Not ready biodegradable | 0.9964 |
| Acute Oral Toxicity | III | 0.7780 |
| Carcinogenicity (Three-class) | Non-required | 0.6031 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -3.8272 | LogS |
| Caco-2 Permeability | -0.0140 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.8492 | LD50, mol/kg |
| Fish Toxicity | 1.1029 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.8482 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Radioligand Recognition of Insecticide Targets. | J Agric Food Chem | 2018 Apr 4 | 29522334 |
| High Concentrations of Chlorantraniliprole Reduce Its Compatibility with a Key Predator, Hippodamia convergens (Coleoptera: Coccinellidae). | J Econ Entomol | 2017 Oct 1 | 28961909 |
| The C-terminal MIR-containing region in the Pmt1 O-mannosyltransferase restrains sporulation and is dispensable for virulence in Beauveria bassiana. | Appl Microbiol Biotechnol | 2017 Feb | 27722917 |
| Caffeine stimulates in vitro pituitary LH secretion in lipopolysaccharide-treated ewes. | Reprod Biol | 2015 Mar | 25726373 |
| Prostaglandin FP receptor inhibitor reduces ischemic brain damage and neurotoxicity. | Neurobiol Dis | 2012 Oct | 22709986 |
| Chronic inhibition of endoplasmic reticulum calcium-release channels and calcium-ATPase lengthens the period of hepatic clock gene Per1. | J Circadian Rhythms | 2011 Jul 8 | 21740569 |
| Trimethyltin chloride induced chloride secretion across rat distal colon. | Cell Biol Int | 2009 Dec 16 | 19947937 |
| Propylene glycol increases cytosolic free calcium in rat cerebrocortical synaptosomes. | Int J Neurosci | 2004 May | 15204065 |
| Effect of short-chain fatty acids on contraction of smooth muscle in the canine colon. | Am J Vet Res | 2002 Feb | 11843133 |
| Selective insect antifeedant and toxic action of ryanoid diterpenes. | J Agric Food Chem | 1999 Oct | 10552828 |
| Alteration of oxytocin-induced calcium oscillations in clone 9 cells by toxin exposure. | Fundam Appl Toxicol | 1996 Oct | 8921340 |
Targets
- General Function:
- Voltage-gated calcium channel activity
- Specific Function:
- Calcium channel that mediates the release of Ca(2+) from the sarcoplasmic reticulum into the cytoplasm and thereby plays a key role in triggering muscle contraction following depolarization of T-tubules. Repeated very high-level exercise increases the open probability of the channel and leads to Ca(2+) leaking into the cytoplasm. Can also mediate the release of Ca(2+) from intracellular stores in neurons, and may thereby promote prolonged Ca(2+) signaling in the brain. Required for normal embryonic development of muscle fibers and skeletal muscle. Required for normal heart morphogenesis, skin development and ossification during embryogenesis (By similarity).
- Gene Name:
- RYR1
- Uniprot ID:
- P21817
- Molecular Weight:
- 565170.715 Da
References
- Ahn KC, Zhao B, Chen J, Cherednichenko G, Sanmarti E, Denison MS, Lasley B, Pessah IN, Kultz D, Chang DP, Gee SJ, Hammock BD: In vitro biologic activities of the antimicrobials triclocarban, its analogs, and triclosan in bioassay screens: receptor-based bioassay screens. Environ Health Perspect. 2008 Sep;116(9):1203-10. doi: 10.1289/ehp.11200. [18795164 ]