Structure via PubChem · Public domain (PubChem)
cnicin
Sign in to saveCnicin is a sesquiterpene lactone, esterified with a substituted acrylic acid, and belonging to the germacranolide class of natural products. It is mainly found in Cnicus (Centaurea--formerly Cnicus--benedictus L. (Asteraceae)), and is present in spotted knapweed plants, where highest and lowest concentrations are found in the leaves (0.86-3.86% cnicin) and stems respectively. Cnicin is used as a bitter tonic and the bitterness value is approximately 1,500.
Chemical data
- Formula
- C20H26O7
- Molecular weight
- 378.4 g/mol
- IUPAC name
- [(3aR,4S,6E,10Z,11aR)-10-(hydroxymethyl)-6-methyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl] (3R)-3,4-dihydroxy-2-methylidenebutanoate
- SMILES
- C/C/1=C\CC/C(=C/[C@@H]2[C@@H]([C@H](C1)OC(=O)C(=C)[C@H](CO)O)C(=C)C(=O)O2)/CO
- InChIKey
- ZTDFZLVUIVPZDU-QGNHJMHWSA-N
- XLogP
- 0.2
- Polar surface area
- 113 Ų
- H-bond donors
- 3
- H-bond acceptors
- 7
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Mass
- 378.167853172
Show 5 more facts
- chemical formula
- C₂₀H₂₆O₇
- isomeric SMILES
- O=C/1O[C@@H]2/C=C(/CC/C=C(/C[C@H](OC(=O)\C(=C)[C@@H](O)CO)[C@H]2C\1=C)C)CO
- canonical SMILES
- O=C(OC1CC(=CCCC(=CC2OC(=O)C(=C)C21)CO)C)C(=C)C(O)CO
- has characteristic
- bitterness
- Commons category
- Cnicin
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
2 sectionsContents
- References
- External links
Cnicin is a sesquiterpene lactone, esterified with a substituted acrylic acid, and belonging to the germacranolide class of natural products. It is mainly found in Cnicus (Centaurea--formerly Cnicus--benedictus L. (Asteraceae)), and is present in spotted knapweed plants, where highest and lowest concentrations are found in the leaves (0.86-3.86% cnicin) and stems respectively. Cnicin is used as a bitter tonic and the bitterness value is approximately 1,500.
==References==
Excerpted from Wikipedia’s “cnicin” article, available under the CC BY-SA 4.0 licence.