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CHEBI:70505 - picrinine

Default Structure
ChEBI IDCHEBI:70505
ChEBI Namepicrinine
Stars
DefinitionA natural product with formula C20H22N2O3 that is the member of the akuammiline family of alkaloids, first isolated in 1965 from the leaves of Alstonia scholaris.
Last Modified18 April 2023
DownloadsMolfile
FormulaC20H22N2O3
Net Charge0
Average Mass338.407
Monoisotopic Mass338.16304
SMILES[H][C@]12C[C@]3([H])N(C/C1=C/C)[C@]1([H])C[C@]4(c5ccccc5N[C@@]43O1)[C@@H]2C(=O)OC
InChIInChI=1S/C20H22N2O3/c1-3-11-10-22-15-8-12(11)17(18(23)24-2)19-9-16(22)25-20(15,19)21-14-7-5-4-6-13(14)19/h3-7,12,15-17,21H,8-10H2,1-2H3/b11-3-/t12-,15-,16-,17-,19-,20-/m0/s1
InChIKeyBDXYPHKGNUGUFG-VETGLWQVSA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Alstonia macrophylla (ncbitaxon:693366) leaf (BTO:0000713) DOI (10.1016/j.bmc.2010.01.077)
Alstonia scholaris (ncbitaxon:52822) fruit (BTO:0000486) PubMed (35888731 )
Alstonia spatulata (IPNI:76595-1) leaf (BTO:0000713) PubMed (21043460) Extraction of leaves with concentrated EtOH with dilute acids.
Hunteria zeylanica (ncbitaxon:1220079) Brush Cell (NCIT:C32236) DOI (10.1016/S0031-9422(00)95285-3)
Melodinus hemsleyanus (IPNI:80210-1) aerial part (BTO:0001658) DOI (10.1016/0031-9422(93)80046-U)
Roles Classification
Biological Roles:
analgesic  An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Applications:
anti-inflammatory agent  Any compound that has anti-inflammatory effects.
antitussive  An agent that suppresses cough. Antitussives have a central or a peripheral action on the cough reflex, or a combination of both. Compare with expectorants, which are considered to increase the volume of secretions in the respiratory tract, so facilitating their removal by ciliary action and coughing, and mucolytics, which decrease the viscosity of mucus, facilitating its removal by ciliary action and expectoration.
anti-asthmatic agent  Any compound that has anti-asthmatic effects.
analgesic  An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.
ChEBI Ontology
Outgoing Relation(s)
picrinine (CHEBI:70505) has role analgesic (CHEBI:35480)
picrinine (CHEBI:70505) has role anti-asthmatic agent (CHEBI:65023)
picrinine (CHEBI:70505) has role anti-inflammatory agent (CHEBI:67079)
picrinine (CHEBI:70505) has role antitussive (CHEBI:51177)
picrinine (CHEBI:70505) has role plant metabolite (CHEBI:76924)
picrinine (CHEBI:70505) is a alkaloid ester (CHEBI:38481)
picrinine (CHEBI:70505) is a indole alkaloid (CHEBI:38958)
picrinine (CHEBI:70505) is a methyl ester (CHEBI:25248)
picrinine (CHEBI:70505) is a organic heteropentacyclic compound (CHEBI:38164)
picrinine (CHEBI:70505) is a polycyclic ether (CHEBI:36468)
Incoming Relation(s)
ervincine (CHEBI:194555) has functional parent picrinine (CHEBI:70505)
IUPAC Name 
methyl (19E)-2α,5β-1,2-dihydro-2,5-epoxyakuammilan-17-oate
Synonyms  Source
16-de[(acetyloxy)methyl]picralineChEBI
2α,5α-epoxy-1,2-dihydroakuammilan-17-oic acid methyl esterChEBI
deacetyldeformopicralineChEBI
methyl (2α,5α,19E)-1,2-dihydro-2,5-epoxyakuammilan-17-oateChEBI
UniProt Name  Source
picrinineUniProt
Manual XrefsDatabases
C00025196KNApSAcK
CN101538271Patent
PicrinineWikipedia
Registry NumbersSources
CAS:4684-32-6KNApSAcK
Citations