Structure via PubChem · Public domain (PubChem)
ouabain
Sign in to saveAlso known as 3-(alpha-L-rhamnopyranosyloxy)-1beta,5beta,11alpha,14,19-pentahydroxy-5beta-card-20(22)-enolide, g-strophanthin
Ouabain or (from Somali waabaayo, "arrow poison" through French ouabaïo) also known as g-strophanthin, is a plant derived toxic substance that was traditionally used as an arrow poison in eastern Africa for both hunting and warfare. Ouabain is a cardiac glycoside and, in lower doses, can be used medically to treat hypotension and some arrhythmias. It acts by inhibiting the Na/K-ATPase, also known as the sodium–potassium ion pump. However, adaptations to the alpha-subunit of the -ATPase via amino acid substitutions, have been observed in certain species, namely some herbivore insect species, th
Chemical data
- Formula
- C29H44O12
- Molecular weight
- 584.7 g/mol
- IUPAC name
- 3-[(1R,3S,5S,8R,9S,10R,11R,13R,14S,17R)-1,5,11,14-tetrahydroxy-10-(hydroxymethyl)-13-methyl-3-[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2H-furan-5-one
- SMILES
- C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@H]2C[C@H]([C@@]3([C@@H]4[C@@H](CC[C@@]3(C2)O)[C@]5(CC[C@@H]([C@]5(C[C@H]4O)C)C6=CC(=O)OC6)O)CO)O)O)O)O
- InChIKey
- LPMXVESGRSUGHW-HBYQJFLCSA-N
- XLogP
- -1.7
- Polar surface area
- 207 Ų
- H-bond donors
- 8
- H-bond acceptors
- 12
- Formal charge
- 0
via PubChem
Research
22,695 papers- Ouabain-induced hypertension in rats: Mechanisms, variability and translational implications.Experimental physiology · 2026
- Endogenous ouabain in cardiovascular function and disease.Journal of hypertension · 2009
- Ouabain, a new steroid hormone of adrenal gland and hypothalamus.Experimental and clinical endocrinology & diabetes : official journal, German Society of Endocrinology [and] German Diabetes Association · 2000
- Endogenous ouabain is not ouabain.Hypertension (Dallas, Tex. : 1979) · 2014
- Ouabain alleviates Mycobacterium abscessus-triggered inflammatory responses through dual regulation of NLRP3 inflammasome activity and M1 macrophage polarization.Frontiers in immunology · 2025
via PubMed
Wikidata facts
- Mass
- 584.283
Show 5 more facts
- chemical formula
- C₂₉H₄₄O₁₂
- isomeric SMILES
- C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@H]2C[C@H]([C@@]3([C@@H]4[C@@H](CC[C@@]3(C2)O)[C@]5(CC[C@@H]([C@]5(C[C@H]4O)C)C6=CC(=O)OC6)O)CO)O)O)O)O
- canonical SMILES
- CC1C(C(C(C(O1)OC2CC(C3(C4C(CCC3(C2)O)C5(CCC(C5(CC4O)C)C6=CC(=O)OC6)O)CO)O)O)O)O
- defined daily dose
- 0.25
- Commons category
- Ouabain
Sources (6)
via Wikidata · CC0
~11 min read
Article
15 sectionsContents
- Sources
- Mechanism of action
- Symptoms
- Toxicology
- Biological effects
- Endogenous ouabain
- Medical uses
- Animal use of ouabain
- Synthesis
- History
- Africa
- Europe
- See also
- References
- External links
Ouabain or (from Somali waabaayo, "arrow poison" through French ouabaïo) also known as g-strophanthin, is a plant derived toxic substance that was traditionally used as an arrow poison in eastern Africa for both hunting and warfare. Ouabain is a cardiac glycoside and, in lower doses, can be used medically to treat hypotension and some arrhythmias. It acts by inhibiting the Na/K-ATPase, also known as the sodium–potassium ion pump. However, adaptations to the alpha-subunit of the -ATPase via amino acid substitutions, have been observed in certain species, namely some herbivore insect species, that have resulted in toxin resistance.
It is classified as an extremely hazardous substance in the United States as defined in Section 302 of the U.S. Emergency Planning and Community Right-to-Know Act (42 U.S.C. 11002), and is subject to strict reporting requirements by facilities which produce, store, or use it in significant quantities.