CHEBI:6941 - (−)-minovincinine

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ChEBI Name (−)-minovincinine
ChEBI ID CHEBI:6941
ChEBI ASCII Name (-)-minovincinine
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information ChemicalBook:CB7463387, ChemicalBook:CB0463388, eMolecules:591516, Selleckchem:mirtazapine-remeron-avanza
Download Molfile XML SDF
Formula C21H26N2O3
Net Charge 0
Average Mass 354.450
Monoisotopic Mass 354.19434
InChI InChI=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
InChIKey BKMGDPNQILJWLI-VLCNGCBASA-N
SMILES [C@@]123CCN4[C@]3([C@](CC(=C2NC5=C1C=CC=C5)C(OC)=O)(CCC4)[C@H](O)C)[H]
Metabolite of Species Details
Stemmadenia tomentosa (IPNI:244360-2) Found in cell suspension culture (BTO:0000221). See: 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 (NCBI:txid141630) Found in cell suspension culture (BTO:0000221). See: 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.
Catharanthus trichophyllus (NCBI:txid319559) Found in hairy root. See: DOI
Catharanthus roseus (NCBI:txid4058) See: Kohl, W., Witte, B. and Hofle, G. (1981) Alkaloids from Catharanthus roseus tissue cultures, II. Z. Naturforsch, 86b, 1153-1162.
Vinca minor (NCBI:txid60093) 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 (−)-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 (−)-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 Sources
(−)-19R-minovincinine ChEBI
(−)-minovincinine ChEBI
19R-hydroxy-(−)-vincadifformine ChEBI
minovincinine KEGG COMPOUND
Manual Xrefs Databases
C00024459 KNApSAcK
C11783 KEGG COMPOUND
View more database links
Citations Types Sources
13943964 PubMed citation Europe PMC
28478314 PubMed citation Europe PMC
29131648 PubMed citation Europe PMC
29438577 PubMed citation Europe PMC
30605851 PubMed citation Europe PMC
31009114 PubMed citation Europe PMC
Last Modified
09 March 2020
General Comment
2019-10-24 Evidence for the hydroxy group to be in the R-configuration is found in Fig. S10 of PMID:31009114.