CHEBI:6941 - (−)-minovincinine

ChEBI IDCHEBI:6941
ChEBI Name(−)-minovincinine
Stars
ASCII Name(-)-minovincinine
DefinitionA monoterpenoid indole alkaloid that is (−)-vincadifformine which carries a hydroxy group at position 19R. A natural product found in several plant species including Catharanthus roseus and Vinca minor.
Last Modified9 March 2020
DownloadsMolfile
FormulaC21H26N2O3
Net Charge0
Average Mass354.450
Monoisotopic Mass354.19434
SMILES[H][C@]12N3CCC[C@@]1([C@@H](C)O)CC(C(=O)OC)=C1Nc4ccccc4[C@@]12CC3
InChIInChI=1S/C21H26N2O3/c1-13(24)20-8-5-10-23-11-9-21(19(20)23)15-6-3-4-7-16(15)22-17(21)14(12-20)18(25)26-2/h3-4,6-7,13,19,22,24H,5,8-12H2,1-2H3/t13-,19+,20+,21+/m1/s1
InChIKeyBKMGDPNQILJWLI-VLCNGCBASA-N
Species of MetaboliteComponentSourceComments
Vinca minor (ncbitaxon:60093) - PubMed (13943964)
Catharanthus roseus (ncbitaxon:4058) - Article (Kohl, W., Witte, B. and Hofle, G. (1981) Alkaloids from Catharanthus roseus tissue cultures, II. Z. Naturforsch, 86b, 1153-1162.)
Catharanthus trichophyllus (ncbitaxon:319559) - DOI (10.1016/S0031-9422(00)98066-X) Found in hairy root.
Stemmadenia tomentosa (IPNI:244360-2) cell suspension culture (BTO:0000221) Article (Stöckigt, J., Pawelka, K-H., Rother, A. and Deus, B. (1982) Indole alkaloids from cell suspension cultures of Stemmadenia tomentosa and Voacanga africana. Z. Naturforsch, 37c, 857-860.)
Voacanga africana (ncbitaxon:141630) cell suspension culture (BTO:0000221) Article (Stöckigt, J., Pawelka, K-H., Rother, A. and Deus, B. (1982) Indole alkaloids from cell suspension cultures of Stemmadenia tomentosa and Voacanga africana. Z. Naturforsch, 37c, 857-860.)
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)
(−)-minovincinine (CHEBI:6941) has role plant metabolite (CHEBI:76924)
(−)-minovincinine (CHEBI:6941) is a Aspidosperma alkaloid (CHEBI:142772)
(−)-minovincinine (CHEBI:6941) is a alkaloid ester (CHEBI:38481)
(−)-minovincinine (CHEBI:6941) is a methyl ester (CHEBI:25248)
(−)-minovincinine (CHEBI:6941) is a monoterpenoid indole alkaloid (CHEBI:65323)
(−)-minovincinine (CHEBI:6941) is a organic heteropentacyclic compound (CHEBI:38164)
(−)-minovincinine (CHEBI:6941) is a secondary alcohol (CHEBI:35681)
(−)-minovincinine (CHEBI:6941) is a secondary amino compound (CHEBI:50995)
(−)-minovincinine (CHEBI:6941) is a tertiary amino compound (CHEBI:50996)
(−)-minovincinine (CHEBI:6941) is conjugate base of (−)-minovincinine(1+) (CHEBI:144373)
(−)-minovincinine (CHEBI:6941) is enantiomer of (+)-minovincinine (CHEBI:145195)
Incoming Relation(s)
(−)-minovincinine(1+) (CHEBI:144373) is conjugate acid of (−)-minovincinine (CHEBI:6941)
(+)-minovincinine (CHEBI:145195) is enantiomer of (−)-minovincinine (CHEBI:6941)
IUPAC Name 
methyl (20R)-20-hydroxy-5α,12β,19α-2,3-didehydroaspidospermidine-3-carboxylate
Synonyms  Source
minovincinineKEGG COMPOUND
(−)-minovincinineChEBI
19R-hydroxy-(−)-vincadifformineChEBI
(−)-19R-minovincinineChEBI
Manual XrefsDatabases
C11783KEGG COMPOUND
C00024459KNApSAcK
Citations