CHEBI:70508 - (16R,19E)-isositsirikine

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ChEBI Name (16R,19E)-isositsirikine
ChEBI ID CHEBI:70508
ChEBI ASCII Name (16R,19E)-isositsirikine
Definition An indole alkaloid with formula C21H26N2O3. It is a natural product found in several plant species including Alstonia spatulata and Catharanthus roseus.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information ZINC000066102567
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Formula C21H26N2O3
Net Charge 0
Average Mass 354.450
Monoisotopic Mass 354.19434
InChI InChI=1S/C21H26N2O3/c1-3-13-11-23-9-8-15-14-6-4-5-7-18(14)22-20(15)19(23)10-16(13)17(12-24)21(25)26-2/h3-7,16-17,19,22,24H,8-12H2,1-2H3/b13-3-/t16-,17-,19-/m0/s1
InChIKey RGXKJLTVROJBKZ-LZNZQLKFSA-N
SMILES [H]C12C=3NC=4C=CC=CC4C3CCN2CC(=CC)C([H])(C1)C(C(=O)OC)CO
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
Kopsia pauciflora (NCBI:txid1037435) Found in Leaf (PO:0025034). See: DOI
Kopsia griffithii (NCBI:txid1750996) Found in Leaf (PO:0025034). See: DOI
Rhazya stricta (NCBI:txid396313) Found in leaf (BTO:0000713). See: DOI
Rhazya stricta (NCBI:txid396313) Found in aerial part (BTO:0001658). See: PubMed
Catharanthus roseus (NCBI:txid4058) Found in cell suspension culture (BTO:0000221). See: PubMed
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.
antifungal agent
An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via alkaloid )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing (16R,19E)-isositsirikine (CHEBI:70508) has role antifungal agent (CHEBI:35718)
(16R,19E)-isositsirikine (CHEBI:70508) has role plant metabolite (CHEBI:76924)
(16R,19E)-isositsirikine (CHEBI:70508) is a indole alkaloid (CHEBI:38958)
(16R,19E)-isositsirikine (CHEBI:70508) is a methyl ester (CHEBI:25248)
(16R,19E)-isositsirikine (CHEBI:70508) is a organic heterotetracyclic compound (CHEBI:38163)
(16R,19E)-isositsirikine (CHEBI:70508) is a primary alcohol (CHEBI:15734)
IUPAC Name
methyl (2R)-2-[(2R,3E,12bS)-3-ethylidene-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-2-yl]-3-hydroxypropanoate
Synonyms Sources
(16R)-E-isositsirikine ChEBI
(16R,19E)-isositsirikine UniProt
16(R)-19,20-E-isositsirikine ChEBI
16(R)-E-isositsirikine ChEBI
16R,19E-isositsirikine ChEBI
16R-19,20-E-isositsirikine ChEBI
Manual Xrefs Databases
4941438 ChemSpider
CPD-21555 MetaCyc
View more database links
Registry Number Type Source
6519-27-3 CAS Registry Number ChEBI
Citations
Last Modified
06 February 2025