Structure via PubChem · Public domain (PubChem)
(S)-scoulerine
Sign in to saveAlso known as (13as)-5, 8,13,13a-tetrahydro-3,10-dimethoxy-6H-dibenzo[a,g]quinolizine-2,9-diol, Aequaline, discretamine, Skoulerine, 3,10-Dimethoxy-13a-alpha-berbine-2,9-diol, (-)-scoulerine
Scoulerine, also known as discretamine and aequaline, is a benzylisoquinoline alkaloid (BIA) that is derived directly from (S)-reticuline through the action of berberine bridge enzyme. It is a precursor of other BIAs, notably berberine, noscapine, (S)-tetrahydropalmatine, and (S)-stylopine, as well as the alkaloids protopine, and sanguinarine. It is found in many plants, including opium poppy, Croton flavens, and certain plants in the genus Erythrina.
In the Vinony graph
Vinony's link graph records 29 inbound references to (S)-scoulerine, and connects out to digital object identifier, chemical formula and Papaver somniferum.
Vinony files it under Catechol ethers, Hydroxyarenes and Isoquinolinoisoquinolines.
Vinony links it to 7 Wikipedia language editions.
Chemical data
- Formula
- C19H21NO4
- Molecular weight
- 327.4 g/mol
- IUPAC name
- (13aS)-3,10-dimethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinoline-2,9-diol
- SMILES
- COC1=C(C2=C(C[C@H]3C4=CC(=C(C=C4CCN3C2)OC)O)C=C1)O
- InChIKey
- KNWVMRVOBAFFMH-HNNXBMFYSA-N
- XLogP
- 2.6
- Polar surface area
- 62.2 Ų
- H-bond donors
- 2
- H-bond acceptors
- 5
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Mass
- 327.147
Show 4 more facts
- chemical formula
- C₁₉H₂₁NO₄
- found in taxon
- Thalictrum flavum
- isomeric SMILES
- COC1=C(C2=C(C[C@H]3C4=CC(=C(C=C4CCN3C2)OC)O)C=C1)O
- canonical SMILES
- COC1=C(C2=C(CC3C4=CC(=C(C=C4CCN3C2)OC)O)C=C1)O
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
2 sectionsContents
- Biosynthesis
- References
Scoulerine, also known as discretamine and aequaline, is a benzylisoquinoline alkaloid (BIA) that is derived directly from (S)-reticuline through the action of berberine bridge enzyme. It is a precursor of other BIAs, notably berberine, noscapine, (S)-tetrahydropalmatine, and (S)-stylopine, as well as the alkaloids protopine, and sanguinarine. It is found in many plants, including opium poppy, Croton flavens, and certain plants in the genus Erythrina.
Studies show that scoulerine is an antagonist in vitro at the α2-adrenoceptor, α1D-adrenoceptor and 5-HT receptor. It has also been found to be a GABAA receptor agonist in vitro.
Excerpted from Wikipedia’s “(S)-scoulerine” article, available under the CC BY-SA 4.0 licence.