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CHEBI:70499 - akuammicine

ChEBI IDCHEBI:70499
ChEBI Nameakuammicine
Stars
DefinitionA monoterpenoid indole alkaloid with formula C20H22N2O2, isolated from several plant species including Alstonia spatulata, Catharanthus roseus and Vinca major.
Secondary ChEBI IDCHEBI:2530
Last Modified17 August 2023
DownloadsMolfile
FormulaC20H22N2O2
Net Charge0
Average Mass322.408
Monoisotopic Mass322.16813
SMILES[H][C@@]12C[C@@H]3N(CC[C@]34C(=C1C(=O)OC)Nc1ccccc14)C/C2=C/C
InChIInChI=1S/C20H22N2O2/c1-3-12-11-22-9-8-20-14-6-4-5-7-15(14)21-18(20)17(19(23)24-2)13(12)10-16(20)22/h3-7,13,16,21H,8-11H2,1-2H3/b12-3-/t13-,16-,20+/m0/s1
InChIKeyAGZMFTKKLPHOMT-DUJTVWLASA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Alstonia spatulata (IPNI:76595-1)
bark (BTO:0001301) PubMed (21043460) Isolated from stem bark.
leaf (BTO:0000713) PubMed (21043460)
Catharanthus roseus (ncbitaxon:4058) aerial part (BTO:0001658) PubMed (29152344)
Rauvolfia caffra (ncbitaxon:947877) bark (BTO:0001301) PubMed (6471882) Isolated from stem bark.
Alstonia angustifolia (IPNI:76506-1) bark (BTO:0001301) PubMed (17262459) Isolated from stem bark.
Vinca major (ncbitaxon:185238) leaf (BTO:0000713) PubMed (17402086)
Picralima nitida (ncbitaxon:52846) seed (PO:0009010) PubMed (9683021)
Alstonia scholaris (ncbitaxon:52822) bark (BTO:0001301) Article (Boonchuay, W. and Court, W.E. (1976) Minor alkaloids of Alstonia scholaris root. Phytochemistry, 15, 821.) Isolated from root bark.
Tabernaemontana divaricata (ncbitaxon:52861) - PubMed (17253850)
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Roles:
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)
akuammicine (CHEBI:70499) has role plant metabolite (CHEBI:76924)
akuammicine (CHEBI:70499) is a methyl ester (CHEBI:25248)
akuammicine (CHEBI:70499) is a monoterpenoid indole alkaloid (CHEBI:65323)
akuammicine (CHEBI:70499) is a organic heteropentacyclic compound (CHEBI:38164)
akuammicine (CHEBI:70499) is a tertiary amino compound (CHEBI:50996)
akuammicine (CHEBI:70499) is conjugate base of akuammicine(1+) (CHEBI:142754)
Incoming Relation(s)
akuammicine(1+) (CHEBI:142754) is conjugate acid of akuammicine (CHEBI:70499)
IUPAC Name 
methyl (19E)-2,16-didehydrocur-19-en-17-oate
Synonyms  Source
methyl (19E)-2,16,19,20-tetradehydrocuran-17-oateChemIDplus
(−)-akuammicineKNApSAcK
Manual XrefsDatabases
C09025KEGG COMPOUND
C00001680KNApSAcK
AkuammicineWikipedia
CPD-21553MetaCyc
Registry NumbersSources
CAS:639-43-0KEGG COMPOUND
CAS:639-43-0ChemIDplus
Citations