hasubanonine

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.

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Vinony's link graph records 4 inbound references to hasubanonine, and connects out to digital object identifier, chemical formula and alkaloid.

It sits within the topics Alkaloids, Chembox image size set and Enones.

Vinony links it to 7 Wikipedia language editions.

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 Å²
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)

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Encyclopedic overview

1 sections

Contents

References

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.