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CHEBI:70499 - akuammicine

Default Structure
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 angustifolia (IPNI:76506-1) bark (BTO:0001301) PubMed (17262459) Isolated from stem bark.
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.
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)
Picralima nitida (ncbitaxon:52846) seed (PO:0009010) PubMed (9683021)
Rauvolfia caffra (ncbitaxon:947877) bark (BTO:0001301) PubMed (6471882) Isolated from stem bark.
Tabernaemontana divaricata (ncbitaxon:52861) - PubMed (17253850)
Vinca major (ncbitaxon:185238) leaf (BTO:0000713) PubMed (17402086)
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
(−)-akuammicineKNApSAcK
methyl (19E)-2,16,19,20-tetradehydrocuran-17-oateChemIDplus
Manual XrefsDatabases
AkuammicineWikipedia
C00001680KNApSAcK
C09025KEGG COMPOUND
CPD-21553MetaCyc
Registry NumbersSources
CAS:639-43-0ChemIDplus
CAS:639-43-0KEGG COMPOUND
Citations