CHEBI:70499 - akuammicine

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ChEBI Name akuammicine
ChEBI ID CHEBI:70499
Definition A monoterpenoid indole alkaloid with formula C20H22N2O2, isolated from several plant species including Alstonia spatulata, Catharanthus roseus and Vinca major.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:2530
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Formula C20H22N2O2
Net Charge 0
Average Mass 322.402
Monoisotopic Mass 322.168
InChI InChI=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
InChIKey AGZMFTKKLPHOMT-DUJTVWLASA-N
SMILES C=12[C@@]3([C@H]4N(CC3)C\C(\[C@@](C1C(=O)OC)(C4)[H])=C\C)C5=CC=CC=C5N2
Metabolite of Species Details
Vinca major Found in leaf (BTO:0000713). See: PubMed
Alstonia angustifolia (IPNI:76506-1) Found in bark (BTO:0001301). Isolated from stem bark. See: PubMed
Alstonia sp.tulata (IPNI:76595-1) Found in bark (BTO:0001301). Isolated from stem bark. See: PubMed
Alstonia sp.tulata (IPNI:76595-1) Found in leaf (BTO:0000713). See: PubMed
Catharanthus roseus (NCBI:txid4058) Found in aerial part (BTO:0001658). See: PubMed
Alstonia scholaris (NCBI:txid52822) Found in bark (BTO:0001301). Isolated from root bark. See: Boonchuay, W. and Court, W.E. (1976) Minor alkaloids of Alstonia scholaris root. Phytochemistry, 15, 821.
Picralima nitida (NCBI:txid52846) Found in seed (PO:0009010). See: PubMed
Tabernaemontana divaricata (NCBI:txid52861) See: PubMed
Rauvolfia caffra (NCBI:txid947877) Found in bark (BTO:0001301). Isolated from stem bark. See: PubMed
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
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.
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 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 akuammicine(1+) (CHEBI:142754) is conjugate acid of akuammicine (CHEBI:70499)
IUPAC Name
methyl (19E)-2,16-didehydrocur-19-en-17-oate
Synonyms Sources
(−)-akuammicine KNApSAcK
methyl (19E)-2,16,19,20-tetradehydrocuran-17-oate ChemIDplus
Manual Xrefs Databases
Akuammicine Wikipedia
C00001680 KNApSAcK
C09025 KEGG COMPOUND
CPD-21553 MetaCyc
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Registry Numbers Types Sources
639-43-0 CAS Registry Number KEGG COMPOUND
639-43-0 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
11506556 PubMed citation Europe PMC
11671452 PubMed citation Europe PMC
17253850 PubMed citation Europe PMC
17262459 PubMed citation Europe PMC
17402086 PubMed citation Europe PMC
21753848 PubMed citation Europe PMC
28827772 PubMed citation Europe PMC
29152344 PubMed citation Europe PMC
6471882 PubMed citation Europe PMC
9683021 PubMed citation Europe PMC
Last Modified
06 December 2018