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

Default Structure
ChEBI IDCHEBI:70508
ChEBI Name(16R,19E)-isositsirikine
Stars
ASCII Name(16R,19E)-isositsirikine
DefinitionAn indole alkaloid with formula C21H26N2O3. It is a natural product found in several plant species including Alstonia spatulata and Catharanthus roseus.
Last Modified6 February 2025
DownloadsMolfile
FormulaC21H26N2O3
Net Charge0
Average Mass354.450
Monoisotopic Mass354.19434
SMILES[H][C@]1([C@H](CO)C(=O)OC)C[C@@]2([H])c3nc4ccccc4c3CCN2C/C1=C/C
InChIInChI=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
InChIKeyRGXKJLTVROJBKZ-LZNZQLKFSA-N
Species of MetaboliteComponentSourceComments
Alstonia spatulata (IPNI:76595-1) leaf (BTO:0000713) PubMed (21043460) Extraction of leaves with concentrated EtOH with dilute acids
Catharanthus roseus (ncbitaxon:4058) cell suspension culture (BTO:0000221) PubMed (17340304)
Kopsia griffithii (ncbitaxon:1750996) Leaf (PO:0025034) DOI (10.1016/s0031-9422(97)00513-x)
Kopsia pauciflora (ncbitaxon:1037435) Leaf (PO:0025034) DOI (10.1016/j.phytochem.2014.09.014)
Rhazya stricta (ncbitaxon:396313)
leaf (BTO:0000713) DOI (10.1016/j.sajb.2020.10.020)
aerial part (BTO:0001658) PubMed (33477682)
Roles Classification
Biological Roles:
antifungal agent  An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
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.
ChEBI Ontology
Outgoing Relation(s)
(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  Source
16R-19,20-E-isositsirikineChEBI
16(R)-19,20-E-isositsirikineChEBI
16R,19E-isositsirikineChEBI
(16R)-E-isositsirikineChEBI
16(R)-E-isositsirikineChEBI
UniProt Name  Source
(16R,19E)-isositsirikineUniProt
Manual XrefsDatabases
4941438ChemSpider
CPD-21555MetaCyc
Registry NumbersSources
CAS:6519-27-3ChEBI
Citations