secodine (CHEBI:146250)

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ChEBI Name	secodine

ChEBI ID	CHEBI:146250

Definition	A methyl ester that is 1H-indole substituted by a 3-methoxy-3-oxoprop-1-en-2-yl group at position 2 and a 2-(5-ethyl-3,4-dihydropyridin-1(2H)-yl)ethyl groups at position 3. It is a transient intermediate in the synthesis of indole alkaloids such as vindoline and vincadifformine.

Stars	This entity has been manually annotated by the ChEBI Team.

Supplier Information

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Formula

C21H26N2O2

Net Charge

Average Mass

338.451

Monoisotopic Mass

338.19943

InChI

InChI=1S/C21H26N2O2/c1-4-16-8-7-12-23(14-16)13-11-18-17-9-5-6-10-19(17)22-20(18)15(2)21(24)25-3/h5-6,9-10,14,22H,2,4,7-8,11-13H2,1,3H3

InChIKey

YQBZNVRQCVYPFC-UHFFFAOYSA-N

SMILES

C1=CC2=C(C=C1)C(CCN3C=C(CCC3)CC)=C(N2)C(C(OC)=O)=C

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):	metabolite Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites. (via alkaloid )

ChEBI Ontology
Outgoing	secodine (CHEBI:146250) is a enamine (CHEBI:47989) secodine (CHEBI:146250) is a enoate ester (CHEBI:51702) secodine (CHEBI:146250) is a methyl ester (CHEBI:25248) secodine (CHEBI:146250) is a monoterpenoid indole alkaloid (CHEBI:65323) secodine (CHEBI:146250) is a olefinic compound (CHEBI:78840) secodine (CHEBI:146250) is a secondary amino compound (CHEBI:50995) secodine (CHEBI:146250) is a tertiary amino compound (CHEBI:50996) secodine (CHEBI:146250) is a tetrahydropyridine (CHEBI:26921) secodine (CHEBI:146250) is conjugate base of secodine(1+) (CHEBI:146231)

Incoming	secodine(1+) (CHEBI:146231) is conjugate acid of secodine (CHEBI:146250)

IUPAC Name

methyl 2-{3-[2-(5-ethyl-3,4-dihydropyridin-1(2H)-yl)ethyl]-1H-indol-2-yl}prop-2-enoate

Synonym	Source
2-{3-[2-(5-ethyl-3,4-dihydropyridin-1(2H)-yl)ethyl]-1H-indol-2-yl}acrylic acid methyl ester	ChEBI

Last Modified

10 March 2020