CHEBI:70505 - picrinine

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ChEBI Name picrinine
ChEBI ID CHEBI:70505
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information No supplier information found for this compound.
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Formula C20H22N2O3
Net Charge 0
Average Mass 338.407
Monoisotopic Mass 338.16304
InChI InChI=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
InChIKey BDXYPHKGNUGUFG-VETGLWQVSA-N
SMILES [H][C@]12C[C@]34[C@H](C(=O)OC)[C@@]5([H])C[C@]([H])(N1C\C5=C\C)[C@]3(NC1=C4C=CC=C1)O2
Metabolite of Species Details
Alstonia sp.tulata (IPNI:76595-1) Found in leaf (BTO:0000713). Extraction of leaves with concentrated EtOH with dilute acids. See: PubMed
Melodinus hemsleyanus (IPNI:80210-1) Found in aerial part (BTO:0001658). See: DOI
Hunteria zeylanica (NCBI:txid1220079) Found in Brush Cell (NCIT:C32236). See: DOI
Alstonia scholaris (NCBI:txid52822) Found in fruit (BTO:0000486). See: PubMed
Alstonia macrophylla (NCBI:txid693366) Found in leaf (BTO:0000713). See: DOI
Roles Classification
Biological Role(s): plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
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.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via alkaloid )
Application(s): 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.
anti-inflammatory agent
Any compound that has anti-inflammatory effects.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 ervincine (CHEBI:194555) has functional parent picrinine (CHEBI:70505)
IUPAC Name
methyl (19E)-2α,5β-1,2-dihydro-2,5-epoxyakuammilan-17-oate
Synonyms Sources
16-de[(acetyloxy)methyl]picraline ChEBI
2α,5α-epoxy-1,2-dihydroakuammilan-17-oic acid methyl ester ChEBI
deacetyldeformopicraline ChEBI
methyl (2α,5α,19E)-1,2-dihydro-2,5-epoxyakuammilan-17-oate ChEBI
picrinine UniProt
Manual Xrefs Databases
C00025196 KNApSAcK
CN101538271 Patent
Picrinine Wikipedia
View more database links
Registry Number Type Source
4684-32-6 CAS Registry Number KNApSAcK
Citations Types Sources
18205369 PubMed citation Europe PMC
19851925 PubMed citation Europe PMC
20189404 PubMed citation Europe PMC
20219658 PubMed citation Europe PMC
20381600 PubMed citation Europe PMC
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31055046 PubMed citation Europe PMC
32387234 PubMed citation Europe PMC
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34325978 PubMed citation Europe PMC
34410141 PubMed citation Europe PMC
35166361 PubMed citation Europe PMC
35888731 PubMed citation Europe PMC
Last Modified
18 April 2023