Structure via PubChem · Public domain (PubChem)
cardenolide
Sign in to saveA cardenolide is a type of steroid. Many plants contain derivatives, collectively known as cardenolides, including many in the form of cardenolide glycosides (cardenolides that contain structural groups derived from sugars). Cardenolide glycosides are often toxic; specifically, they are heart-arresting. Cardenolides are toxic to animals through inhibition of the enzyme Na+/K+-ATPase, which is responsible for maintaining the sodium and potassium ion gradients across the cell membranes.
Chemical data
- Formula
- C23H34O2
- Molecular weight
- 342.5 g/mol
- IUPAC name
- (4R)-4-[(8R,9S,10S,13S,14R,17R)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]oxolan-2-one
- SMILES
- C[C@]12CCCCC1CC[C@@H]3[C@@H]2CC[C@]4([C@@H]3C=C[C@@H]4[C@H]5CC(=O)OC5)C
- InChIKey
- PHLRMGUUVNOKNG-OCYOQFCJSA-N
- XLogP
- 6.5
- Polar surface area
- 26.3 Ų
- H-bond donors
- 0
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Wikidata facts
- Has part
- hydrogen
- Mass
- 342.25588032799993
Show 4 more facts
- isomeric SMILES
- C[C@]12CC[C@H]3[C@@H](CCC4CCCC[C@@]43C)[C@H]1C=C[C@@H]2[C@@H]1COC(=O)C1
- canonical SMILES
- CC12CCCCC1CCC3C2CCC4(C3C=CC4C5CC(=O)OC5)C
- chemical formula
- C₂₃H₃₄O₂
- topic's main category
- Category:Cardenolides
Sources (2)
via Wikidata · CC0
~3 min read
Encyclopedic overview
4 sectionsContents
- Etymology
- Structure
- As defense mechanism
- References
A cardenolide is a type of steroid. Many plants contain derivatives, collectively known as cardenolides, including many in the form of cardenolide glycosides (cardenolides that contain structural groups derived from sugars). Cardenolide glycosides are often toxic; specifically, they are heart-arresting. Cardenolides are toxic to animals through inhibition of the enzyme Na+/K+-ATPase, which is responsible for maintaining the sodium and potassium ion gradients across the cell membranes.
==Etymology== The term derives from card- "heart" (from Greek καρδία kardiā) and the suffix , referring to the lactone ring with double bond at C17. Cardenolides are a class of steroids (or aglycones if viewed as cardiac glycoside constituents), and cardenolides are a subtype of this class (see MeSH D codes list).
Excerpted from Wikipedia’s “cardenolide” article, available under the CC BY-SA 4.0 licence.