Structure via PubChem · Public domain (PubChem)
protopine
Sign in to saveAlso known as Macleyine, Fumarine, Corydinine, 4,6,7,14-Tetrahydro-5-methyl-bis(1,3)benzodioxolo(4,5-c-5',6'-g)azecin-13(5H)-one, 7-methyl-6,8,9,16-tetrahydrobis[1,3]benzodioxolo[4,5-c:5',6'-g]azecin-15(7H)-one, Bis(1,3)benzodioxolo(4,5-c:5',6'-g)azecin-13(5H)-one,4,6,7,14-tetrahydro-5-methyl-, 7,13a-Secoberbin-13a-one, 7-methyl-2,3:9,10-bis(methylenedioxy)-, Biflorine
Protopine is an alkaloid occurring in opium poppy, Corydalis tubers and other plants of the family papaveraceae, like Fumaria officinalis.
Chemical data
- Formula
- C20H19NO5
- Molecular weight
- 353.4 g/mol
- IUPAC name
- 15-methyl-7,9,19,21-tetraoxa-15-azapentacyclo[15.7.0.04,12.06,10.018,22]tetracosa-1(17),4,6(10),11,18(22),23-hexaen-3-one
- SMILES
- CN1CCC2=CC3=C(C=C2C(=O)CC4=C(C1)C5=C(C=C4)OCO5)OCO3
- InChIKey
- GPTFURBXHJWNHR-UHFFFAOYSA-N
- XLogP
- 2.8
- 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
Research
402 papers- Protopine ameliorates OVA-induced asthma through modulatingTLR4/MyD88/NF-κB pathway and NLRP3 inflammasome-mediated pyroptosis.Phytomedicine : international journal of phytotherapy and phytopharmacology · 2024
- Protopine and Allocryptopine Interactions with Plasma Proteins.International journal of molecular sciences · 2024
- Identification and Quantification, Metabolism and Pharmacokinetics, Pharmacological Activities, and Botanical Preparations of Protopine: A Review.Molecules (Basel, Switzerland) · 2021
- Protopine protects chondrocytes from undergoing ferroptosis by activating Nrf2 pathway.Biochemical and biophysical research communications · 2024
- Protopine hydrochloride.Acta crystallographica. Section C, Crystal structure communications · 2001
via PubMed
Wikidata facts
- Has part
- hydrogen
- Mass
- 353.126323
Show 5 more facts
- chemical formula
- C₂₀H₁₉NO₅
- canonical SMILES
- CN1CCC2=CC3=C(C=C2C(=O)CC4=C(C1)C5=C(C=C4)OCO5)OCO3
- found in taxon
- Thalictrum flavum
- subject has role
- H1 antagonist
- Commons category
- Protopine
via Wikidata · CC0
~1 min read
Encyclopedic overview
4 sectionsContents
- Biosynthesis
- Metabolism
- See also
- References
Protopine is an alkaloid occurring in opium poppy, Corydalis tubers and other plants of the family papaveraceae, like Fumaria officinalis.
It has been found to inhibit histamine H1 receptors and platelet aggregation, and acts as an analgesic.
Excerpted from Wikipedia’s “protopine” article, available under the CC BY-SA 4.0 licence.