Oleandrin
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Basic Info
| Common Name | Oleandrin(F04806) |
| 2D Structure | |
| Description | Oleandrin is a plant toxin found in Oleander (Nerium oleander). It causes both gastrointestinal and cardiac effects. (L1253) |
| FRCD ID | F04806 |
| CAS Number | 465-16-7 |
| PubChem CID | 261943 |
| Formula | C32H48O9 |
| IUPAC Name | [(3S,5R,8R,9S,10S,13R,14S,16S,17R)-14-hydroxy-3-(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy-10,13-dimethyl-17-(5-oxo-2H-furan-3-yl)-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-16-yl] acetate |
| InChI Key | JLPDBLFIVFSOCC-UJQZKUKMSA-N |
| InChI | InChI=1S/C32H48O9/c1-17-29(35)24(37-5)14-27(39-17)41-21-8-10-30(3)20(13-21)6-7-23-22(30)9-11-31(4)28(19-12-26(34)38-16-19)25(40-18(2)33)15-32(23,31)36/h12,17,20-25,27-29,35-36H,6-11,13-16H2,1-5H3/t17?,20-,21+,22+,23-,24?,25+,27?,28+,29?,30+,31-,32+/m1/s1 |
| Canonical SMILES | CC1C(C(CC(O1)OC2CCC3(C(C2)CCC4C3CCC5(C4(CC(C5C6=CC(=O)OC6)OC(=O)C)O)C)C)OC)O |
| Isomeric SMILES | CC1C(C(CC(O1)O[C@H]2CC[C@]3([C@@H](C2)CC[C@@H]4[C@@H]3CC[C@]5([C@@]4(C[C@@H]([C@@H]5C6=CC(=O)OC6)OC(=O)C)O)C)C)OC)O |
| Synonyms |
[(3S,5R,8R,9S,10S,13R,14S,16S,17R)-14-hydroxy-3-(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy-10,13-dimethyl-17-(5-oxo-2H-furan-3-yl)-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-16-yl] acetate
Corrigen
NSC692219
465-16-7
AC1L66E8
NSC95089
NSC-95089
NSC-692219
Card-20(22)-enolide,6-dideoxy-3-O-methyl-.alpha.-L-arabino-hexopyranosyl)oxy]-14-hydroxy-, (3.beta.,5.beta.,16.beta.)-
|
| Classifies |
Plant Toxin
|
| Update Date | Nov 13, 2018 17:07 |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 576.727 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 9 |
| Rotatable Bond Count | 6 |
| Complexity | 1080 |
| Monoisotopic Mass | 576.33 |
| Exact Mass | 576.33 |
| XLogP | 2.4 |
| Formal Charge | 0 |
| Heavy Atom Count | 41 |
| Defined Atom Stereocenter Count | 9 |
| Undefined Atom Stereocenter Count | 4 |
| 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- | 0.5815 |
| Human Intestinal Absorption | HIA+ | 0.9608 |
| Caco-2 Permeability | Caco2- | 0.7708 |
| P-glycoprotein Substrate | Substrate | 0.8360 |
| P-glycoprotein Inhibitor | Inhibitor | 0.7363 |
| Inhibitor | 0.8246 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8110 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.8454 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8724 |
| CYP450 2D6 Substrate | Non-substrate | 0.9142 |
| CYP450 3A4 Substrate | Substrate | 0.7490 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.9087 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9043 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9540 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.9471 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.8309 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9394 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9794 |
| Inhibitor | 0.5770 | |
| AMES Toxicity | Non AMES toxic | 0.8790 |
| Carcinogens | Non-carcinogens | 0.9644 |
| Fish Toxicity | High FHMT | 0.9762 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9974 |
| Honey Bee Toxicity | High HBT | 0.8112 |
| Biodegradation | Not ready biodegradable | 0.9710 |
| Acute Oral Toxicity | I | 0.8422 |
| Carcinogenicity (Three-class) | Non-required | 0.4628 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -4.7343 | LogS |
| Caco-2 Permeability | 0.7515 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 4.8867 | LD50, mol/kg |
| Fish Toxicity | 0.6761 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 1.0675 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Unexpectedly dangerous escargot stew: oleandrin poisoning through the alimentary chain. | J Anal Toxicol | 2006 Nov-Dec | 17137529 |
| Toxic potential of oleander derived compost and vegetables grown with oleander soil amendments. | Vet Hum Toxicol | 2003 Aug | 12882497 |
| Multiresidue screen for cardiotoxins by two-dimensional thin-layer chromatography. | J Agric Food Chem | 2000 Jan | 10637052 |
| Diagnosis of oleander poisoning in livestock. | J Vet Diagn Invest | 1996 Jul | 8844581 |
Targets
- General Function:
- Transporter activity
- Specific Function:
- May be involved in forming the receptor site for cardiac glycoside binding or may modulate the transport function of the sodium ATPase.
- Gene Name:
- FXYD2
- Uniprot ID:
- P54710
- Molecular Weight:
- 7283.265 Da
- Mechanism of Action:
- Oleandrin likely exerts its toxic effects by inhibiting Na+,K+-ATPase.
References
- Jortani SA, Helm RA, Valdes R Jr: Inhibition of Na,K-ATPase by oleandrin and oleandrigenin, and their detection by digoxin immunoassays. Clin Chem. 1996 Oct;42(10):1654-8. [8855150 ]
- General Function:
- Steroid hormone binding
- Specific Function:
- This is the catalytic component of the active enzyme, which catalyzes the hydrolysis of ATP coupled with the exchange of sodium and potassium ions across the plasma membrane. This action creates the electrochemical gradient of sodium and potassium, providing the energy for active transport of various nutrients.
- Gene Name:
- ATP1A2
- Uniprot ID:
- P50993
- Molecular Weight:
- 112264.385 Da
- Mechanism of Action:
- Oleandrin likely exerts its toxic effects by inhibiting Na+,K+-ATPase.
References
- Jortani SA, Helm RA, Valdes R Jr: Inhibition of Na,K-ATPase by oleandrin and oleandrigenin, and their detection by digoxin immunoassays. Clin Chem. 1996 Oct;42(10):1654-8. [8855150 ]
- General Function:
- Steroid hormone binding
- Specific Function:
- This is the catalytic component of the active enzyme, which catalyzes the hydrolysis of ATP coupled with the exchange of sodium and potassium ions across the plasma membrane. This action creates the electrochemical gradient of sodium and potassium ions, providing the energy for active transport of various nutrients.
- Gene Name:
- ATP1A3
- Uniprot ID:
- P13637
- Molecular Weight:
- 111747.51 Da
- Mechanism of Action:
- Oleandrin likely exerts its toxic effects by inhibiting Na+,K+-ATPase.
References
- Jortani SA, Helm RA, Valdes R Jr: Inhibition of Na,K-ATPase by oleandrin and oleandrigenin, and their detection by digoxin immunoassays. Clin Chem. 1996 Oct;42(10):1654-8. [8855150 ]
- General Function:
- Sodium:potassium-exchanging atpase activity
- Specific Function:
- This is the non-catalytic component of the active enzyme, which catalyzes the hydrolysis of ATP coupled with the exchange of Na(+) and K(+) ions across the plasma membrane. The beta subunit regulates, through assembly of alpha/beta heterodimers, the number of sodium pumps transported to the plasma membrane.Involved in cell adhesion and establishing epithelial cell polarity.
- Gene Name:
- ATP1B1
- Uniprot ID:
- P05026
- Molecular Weight:
- 35061.07 Da
- Mechanism of Action:
- Oleandrin likely exerts its toxic effects by inhibiting Na+,K+-ATPase.
References
- Jortani SA, Helm RA, Valdes R Jr: Inhibition of Na,K-ATPase by oleandrin and oleandrigenin, and their detection by digoxin immunoassays. Clin Chem. 1996 Oct;42(10):1654-8. [8855150 ]
- General Function:
- Sodium:potassium-exchanging atpase activity
- Specific Function:
- This is the non-catalytic component of the active enzyme, which catalyzes the hydrolysis of ATP coupled with the exchange of Na(+) and K(+) ions across the plasma membrane. The exact function of the beta-2 subunit is not known.Mediates cell adhesion of neurons and astrocytes, and promotes neurite outgrowth.
- Gene Name:
- ATP1B2
- Uniprot ID:
- P14415
- Molecular Weight:
- 33366.925 Da
- Mechanism of Action:
- Oleandrin likely exerts its toxic effects by inhibiting Na+,K+-ATPase.
References
- Jortani SA, Helm RA, Valdes R Jr: Inhibition of Na,K-ATPase by oleandrin and oleandrigenin, and their detection by digoxin immunoassays. Clin Chem. 1996 Oct;42(10):1654-8. [8855150 ]
- General Function:
- Sodium:potassium-exchanging atpase activity
- Specific Function:
- This is the non-catalytic component of the active enzyme, which catalyzes the hydrolysis of ATP coupled with the exchange of Na(+) and K(+) ions across the plasma membrane. The exact function of the beta-3 subunit is not known.
- Gene Name:
- ATP1B3
- Uniprot ID:
- P54709
- Molecular Weight:
- 31512.34 Da
- Mechanism of Action:
- Oleandrin likely exerts its toxic effects by inhibiting Na+,K+-ATPase.
References
- Jortani SA, Helm RA, Valdes R Jr: Inhibition of Na,K-ATPase by oleandrin and oleandrigenin, and their detection by digoxin immunoassays. Clin Chem. 1996 Oct;42(10):1654-8. [8855150 ]
- General Function:
- Steroid hormone binding
- Specific Function:
- This is the catalytic component of the active enzyme, which catalyzes the hydrolysis of ATP coupled with the exchange of sodium and potassium ions across the plasma membrane. This action creates the electrochemical gradient of sodium and potassium ions, providing the energy for active transport of various nutrients.
- Gene Name:
- ATP1A1
- Uniprot ID:
- P05023
- Molecular Weight:
- 112895.01 Da
- Mechanism of Action:
- Oleandrin likely exerts its toxic effects by inhibiting Na+,K+-ATPase.
References
- Jortani SA, Helm RA, Valdes R Jr: Inhibition of Na,K-ATPase by oleandrin and oleandrigenin, and their detection by digoxin immunoassays. Clin Chem. 1996 Oct;42(10):1654-8. [8855150 ]
- General Function:
- Sodium:potassium-exchanging atpase activity
- Specific Function:
- This is the catalytic component of the active enzyme, which catalyzes the hydrolysis of ATP coupled with the exchange of sodium and potassium ions across the plasma membrane. This action creates the electrochemical gradient of sodium and potassium ions, providing the energy for active transport of various nutrients. Plays a role in sperm motility.
- Gene Name:
- ATP1A4
- Uniprot ID:
- Q13733
- Molecular Weight:
- 114165.44 Da
- Mechanism of Action:
- Oleandrin likely exerts its toxic effects by inhibiting Na+,K+-ATPase.
References
- Jortani SA, Helm RA, Valdes R Jr: Inhibition of Na,K-ATPase by oleandrin and oleandrigenin, and their detection by digoxin immunoassays. Clin Chem. 1996 Oct;42(10):1654-8. [8855150 ]
- General Function:
- Temperature-gated cation channel activity
- Specific Function:
- Receptor-activated non-selective cation channel involved in detection of pain and possibly also in cold perception and inner ear function (PubMed:25389312, PubMed:25855297). Has a central role in the pain response to endogenous inflammatory mediators and to a diverse array of volatile irritants, such as mustard oil, cinnamaldehyde, garlic and acrolein, an irritant from tears gas and vehicule exhaust fumes (PubMed:25389312, PubMed:20547126). Is also activated by menthol (in vitro)(PubMed:25389312). Acts also as a ionotropic cannabinoid receptor by being activated by delta(9)-tetrahydrocannabinol (THC), the psychoactive component of marijuana (PubMed:25389312). May be a component for the mechanosensitive transduction channel of hair cells in inner ear, thereby participating in the perception of sounds. Probably operated by a phosphatidylinositol second messenger system (By similarity).
- Gene Name:
- TRPA1
- Uniprot ID:
- O75762
- Molecular Weight:
- 127499.88 Da
References
- Nilius B, Prenen J, Owsianik G: Irritating channels: the case of TRPA1. J Physiol. 2011 Apr 1;589(Pt 7):1543-9. doi: 10.1113/jphysiol.2010.200717. Epub 2010 Nov 15. [21078588 ]