Structure via PubChem · Public domain (PubChem)
Cryogenine
Sign in to saveCryogenine, also known as vertine or (10α)-4,5-dimethoxy-2-hydroxylythran-12-one, is a biphenylquinolizidine lactone alkaloid from the plants Sinicuichi (Heimia salicifolia) and H. myrtifolia. The compound has no psychoactive properties in humans up to 310 mg, but has shown anti-inflammatory activity similar to aspirin.
Chemical data
- Formula
- C26H29NO5
- Molecular weight
- 435.5 g/mol
- IUPAC name
- (1S,13Z,17S,19R)-9-hydroxy-4,5-dimethoxy-16-oxa-24-azapentacyclo[15.7.1.18,12.02,7.019,24]hexacosa-2,4,6,8,10,12(26),13-heptaen-15-one
- SMILES
- COC1=C(C=C2C(=C1)[C@@H]3C[C@H](C[C@@H]4N3CCCC4)OC(=O)/C=C\C5=CC2=C(C=C5)O)OC
- InChIKey
- WCZWUYYJZVBKDZ-VMSBZHFZSA-N
- XLogP
- 4.6
- Polar surface area
- 68.2 Ų
- H-bond donors
- 1
- H-bond acceptors
- 6
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Mass
- 435.204573
Show 4 more facts
- chemical formula
- C₂₆H₂₉NO₅
- canonical SMILES
- COC1=C(C=C2C(=C1)C3CC(CC4N3CCCC4)OC(=O)C=CC5=CC2=C(C=C5)O)OC
- isomeric SMILES
- [H][C@]1([C@H]2N([C@@H]3C4=CC(=C(C=C4C5=C(C=CC(=C5)/C=C\C(=O)O[C@@H](C2)C3)O)OC)OC)CCC1)[H]
- found in taxon
- Heimia salicifolia
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
1 sectionsContents
- References
Cryogenine, also known as vertine or (10α)-4,5-dimethoxy-2-hydroxylythran-12-one, is a biphenylquinolizidine lactone alkaloid from the plants Sinicuichi (Heimia salicifolia) and H. myrtifolia. The compound has no psychoactive properties in humans up to 310 mg, but has shown anti-inflammatory activity similar to aspirin.
The freebase form melts at 250–251 °C and is soluble in moderately polar organic solvents such as chloroform, methylene chloride, benzene, and methanol, but is insoluble in water and petroleum ether.
Excerpted from Wikipedia’s “Cryogenine” article, available under the CC BY-SA 4.0 licence.