Structure via PubChem · Public domain (PubChem)
hasubanonine
Sign in to saveHasubanonine is a member of the hasubanan family of alkaloids. The alkaloid with an isoquinoline substructure has the molecular formula of C21H27NO5. The enantiomer of the natural product is being studied as a potential painkiller. Hasubanonine is structurally related to the morphinan class of opioid analgesics.
Chemical data
- Formula
- C21H27NO5
- Molecular weight
- 373.4 g/mol
- IUPAC name
- (1S,10S)-3,4,11,12-tetramethoxy-17-methyl-17-azatetracyclo[8.4.3.01,10.02,7]heptadeca-2(7),3,5,11-tetraen-13-one
- SMILES
- CN1CC[C@@]23[C@@]1(CCC4=C2C(=C(C=C4)OC)OC)C(=C(C(=O)C3)OC)OC
- InChIKey
- DXUSNRCTWFHYFS-LEWJYISDSA-N
- XLogP
- 2.1
- Polar surface area
- 57.2 Ų
- H-bond donors
- 0
- H-bond acceptors
- 6
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Mass
- 373.188923
Show 4 more facts
- chemical formula
- C₂₁H₂₇NO₅
- canonical SMILES
- CN1CCC23C1(CCC4=C2C(=C(C=C4)OC)OC)C(=C(C(=O)C3)OC)OC
- isomeric SMILES
- CN1CC[C@@]23[C@@]1(CCC4=C2C(=C(C=C4)OC)OC)C(=C(C(=O)C3)OC)OC
- found in taxon
- Stephania japonica
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
1 sectionsContents
- References
Hasubanonine is a member of the hasubanan family of alkaloids. The alkaloid with an isoquinoline substructure has the molecular formula of C21H27NO5. The enantiomer of the natural product is being studied as a potential painkiller. Hasubanonine is structurally related to the morphinan class of opioid analgesics.
The enantioselective total synthesis of (–)-hasubanonine and related natural products, (−)-runanine, (−)-delavayine, and (+)-periglaucine B were first achieved by Prof. Seth Herzon and co-workers at Yale University in 2011.
Excerpted from Wikipedia’s “hasubanonine” article, available under the CC BY-SA 4.0 licence.