1. Home
  2. Inhibitor
  3. Cinchonine

Cinchonine

Cinchonine and Cinchonidine are natural products found in Dendrosenecio kilimanjari, Cinchona calisaya, CD Ki BCHE 28+/-4 Micro M Ki ACHE >400 micro M; CN Ki BCHE 4.9 +/- 1.4 microM Ki ACHE 34 +/- 1 microM. Poor inhibitor but lead for new activr compounds

General

Type : Natural,Alkaloid,Derivative of Cinchonine,Quinoline,Azabicyclo

Chemical_Nomenclature : (5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl)-quinolin-4-ylmethanol

Canonical SMILES : C=CC1CN2CCC1CC2C(C3=CC=NC4=CC=CC=C34)O

InChI : InChI=1S\/C19H22N2O\/c1-2-13-12-21-10-8-14(13)11-18(21)19(22)16-7-9-20-17-6-4-3-5-15(16)17\/h2-7,9,13-14,18-19,22H,1,8,10-12H2

InChIKey : KMPWYEUPVWOPIM-UHFFFAOYSA-N

Other name(s) : Cinchonan-9-ol,alpha-Quinidine

MW : 294.4

Formula : C19H22N2O

CAS_number : 118-10-5 || 485-71-2

PubChem : 2757

UniChem : KMPWYEUPVWOPIM-UHFFFAOYSA-N

Target

Families : Cinchonine ligand of proteins in family
BCHE

References (4)

Title : Design and evaluation of selective butyrylcholinesterase inhibitors based on Cinchona alkaloid scaffold - Bosak_2018_PLoS.One_13_e0205193
Author(s) : Bosak A , Ramic A , Smidlehner T , Hrenar T , Primozic I , Kovarik Z
Ref : PLoS ONE , 13 :e0205193 , 2018
Abstract : Bosak_2018_PLoS.One_13_e0205193
ESTHER : Bosak_2018_PLoS.One_13_e0205193
PubMedSearch : Bosak_2018_PLoS.One_13_e0205193
PubMedID: 30289893

Title : New Cinchona Oximes Evaluated as Reactivators of Acetylcholinesterase and Butyrylcholinesterase Inhibited by Organophosphorus Compounds - Katalinic_2017_Molecules_22_
Author(s) : Katalinic M , Zandona A , Ramic A , Zorbaz T , Primozic I , Kovarik Z
Ref : Molecules , 22 : , 2017
Abstract : Katalinic_2017_Molecules_22_
ESTHER : Katalinic_2017_Molecules_22_
PubMedSearch : Katalinic_2017_Molecules_22_
PubMedID: 28737687

Title : Chemical modifications of cinchona alkaloids lead to enhanced inhibition of human butyrylcholinesterase - Karlsson_2014_Nat.Prod.Commun_9_455
Author(s) : Karlsson D , Fallarero A , Shinde P , Anju CP , Busygin I , Leino R , Mohan CG , Vuorela P
Ref : Nat Prod Commun , 9 :455 , 2014
Abstract : Karlsson_2014_Nat.Prod.Commun_9_455
ESTHER : Karlsson_2014_Nat.Prod.Commun_9_455
PubMedSearch : Karlsson_2014_Nat.Prod.Commun_9_455
PubMedID: 24868853

Title : Cation-Pi and Pi-Pi stacking interactions allow selective inhibition of butyrylcholinesterase by modified quinine and cinchonidine alkaloids - Nawaz_2011_Biochem.Biophys.Res.Commun_404_935
Author(s) : Nawaz SA , Ayaz M , Brandt W , Wessjohann LA , Westermann B
Ref : Biochemical & Biophysical Research Communications , 404 :935 , 2011
Abstract : Nawaz_2011_Biochem.Biophys.Res.Commun_404_935
ESTHER : Nawaz_2011_Biochem.Biophys.Res.Commun_404_935
PubMedSearch : Nawaz_2011_Biochem.Biophys.Res.Commun_404_935
PubMedID: 21185266 
Array
(
    [id] => 816
    [inhibitor] => Cinchonine
    [type] => Array
        (
            [0] => Natural
            [1] => Alkaloid
            [2] => Derivative of Cinchonine
            [3] => Quinoline
            [4] => Azabicyclo
        )

    [other_name] => Array
        (
            [0] => Cinchonan-9-ol
            [1] => alpha-Quinidine
        )

    [chemical_nomenclature] => (5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl)-quinolin-4-ylmethanol
    [formula] => C19H22N2O
    [cas_number] => 118-10-5 || 485-71-2
    [mw] => 294.4
    [pick_me_to_call] => display_script
    [kinetic_parameter] => 
    [paper] => Karlsson_2014_Nat.Prod.Commun_9_455 || Bosak_2018_PLoS.One_13_e0205193 || Katalinic_2017_Molecules_22_ || Nawaz_2011_Biochem.Biophys.Res.Commun_404_935
    [comment] => Cinchonine and Cinchonidine are natural products found in Dendrosenecio kilimanjari, Cinchona calisaya,  CD Ki BCHE 28+\/-4 Micro M Ki ACHE >400 micro M\;  CN   Ki BCHE 4.9 +\/- 1.4 microM       Ki ACHE 34 +\/- 1 microM. Poor inhibitor but lead for new activr compounds
    [gene_locus] => 
    [kin_inhibitor] => 
    [cid] => 2757
    [family] => BCHE
    [inchikey] => KMPWYEUPVWOPIM-UHFFFAOYSA-N
    [canonicalsmiles] => C=CC1CN2CCC1CC2C(C3=CC=NC4=CC=CC=C34)O
    [inchi] => InChI=1S\/C19H22N2O\/c1-2-13-12-21-10-8-14(13)11-18(21)19(22)16-7-9-20-17-6-4-3-5-15(16)17\/h2-7,9,13-14,18-19,22H,1,8,10-12H2
    [wikipedia] => 
    [iupharlig] => 
    [structure] => 
    [substrate] => 
    [interact_gene_locus] => 
    [mutation] => 
    [comment2] => 
    [extoxnet] => 
    [news] => 
    [theoretical_model] => 
)