Natural Product (NP) Details

General Information of the NP (ID: NP1309)
Name
Cinchonine
Synonyms
cinchonine; (+)-Cinchonine; 118-10-5; D-Cinchonine; Cinchonan-9-ol, (9S)-; (9S)-Cinchonan-9-ol; (8R,9S)-Cinchonine; (+)-Cinconine; TCMDC-123933; cinchonin; UNII-V43X79NZCD; (+)-cinchonin; GNF-Pf-3189; MFCD00064372; V43X79NZCD; CHEBI:27509; (S)-quinolin-4-yl((1S,2R,4S,5R)-5-vinylquinuclidin-2-yl)methanol; (1S)-Quinolin-4-yl((2R,4S,5R)-5-vinylquinuclidin-2-yl)methanol; NSC6176; .alpha.-Quinidine; (S)-Quinolin-4-yl-(5-vinyl-1-aza-bicyclo[2.2.2]oct-2-yl)-methanol; 2-Quinuclidinemethanol, alpha-4-quinolyl-5-vinyl-; NSC-6176; NSC 6176; EINECS 204-234-6; CINCHORINE; PubChem7961; AI3-09058; Prestwick3_000608; 2-Quinuclidinemethanol, .alpha.-4-quinolyl-5-vinyl-; (+)-Cinchonine, 85%; (+)-Cinchonine; >99%; BSPBio_000516; MLS002153907; SCHEMBL158394; 2-Quinuclidinemethanol, alpha-(5-vinyl-2-quinolyl)-; BPBio1_000568; CHEMBL588619; MEGxp0_001905; (S)-Quinolin-4-yl((1S,2R,4S,5S)-5-vinylquinuclidin-2-yl)methanol; DTXSID6045082; ACon0_001352; ACon1_000336; HMS2096J18; HMS2235N18; HY-Y0152; ZINC3881680; (+)-Cinchonine, analytical standard; BDBM50370411; AKOS015895982; EBD2201796; (S)-[(2R,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-quinolin-4-ylmethanol; NCGC00169174-01; NCGC00169174-02; NCGC00262542-03; DS-15267; NCI60_005298; SMR001233256; Cinchonine, crystallized, >=98.0% (NT); AB00374715; CS-0008420; WLN: T66 BNJ EYQ-DT66 A B CNTJ A1U1; Q2972710; BRD-K90268819-001-03-4; 2-Quinuclidinemethanol, .alpha.-(5-vinyl-2-quinolyl)-; NCGC00262542-03_C19H22N2O_(9S)-Cinchonan-9-ol; (S)-4-quinolyl-[(2R,4S,5R)-5-vinylquinuclidin-2-yl]methanol; (S)-quinolin-4-yl((2R,4S,5R)-5-vinylquinuclidin-2-yl)methanol
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Species Origin Cinchona calisaya ...     Click to Show/Hide
Cinchona calisaya
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Gentianales
Family: Rubiaceae
Genus: Cinchona
Species: Cinchona calisaya
Disease Hepatocellular carcinoma [ICD-11: 2C12] Investigative [1]
Structure
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2D MOL

3D MOL

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Formula
C19H22N2O
PubChem CID
90454
Canonical SMILES
C=CC1CN2CCC1CC2C(C3=CC=NC4=CC=CC=C34)O
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/t13-,14-,18+,19-/m0/s1
InChIKey
KMPWYEUPVWOPIM-QAMTZSDWSA-N
CAS Number
CAS 118-10-5
ChEBI ID
CHEBI:27509
Herb ID
HBIN020637
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Drug(s) Whose Efficacy can be Enhanced by This NP
          Doxorubicin      Solid tumour/cancer     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Down-regulation Expression ABCB1  Molecule Info 
Pathway MAP
                    Experimental
                    Result(s)		 A non-cytotoxic concentration of cinchonine (10 microM) increased the sensitivity to doxorubicin of multidrug-resistant P388/DOX cells and significantly enhanced the doxorubicin-induced apoptosis and DNA fragmentation in resistant cells, but had no effect in parent cells.
    β. A List of Drug(s) Whose Resistance can be Reversed by This NP
          Hydrocinchonine + Quinidine     Click to Show/Hide the Molecular Data of This Drug
                 Reversing Drug Resistance     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [3]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Down-regulation Expression ABCB1  Molecule Info 
Pathway MAP
Up-regulation Cleavage CASP3  Molecule Info 
Pathway MAP
Up-regulation Cleavage PARP1  Molecule Info 
Pathway MAP
                    In-vitro Model MES-SA CVCL_1404 Uterine corpus sarcoma Homo sapiens
MES-SA/Dx5 CVCL_2598 Uterine corpus sarcoma Homo sapiens
                    Experimental
                    Result(s)		 Hydrocinchonine exerted MDR reversal activity and synergistic apoptotic effect with TAX in MES-SA/DX5 cells almost comparable with quinidine and cinchonine as a potent MDR-reversal and combined therapy agent with TAX.
Target and Pathway
Target(s) TNF receptor-associated factor 6 (TRAF6)  Molecule Info  [4]
References
Reference 1 Cinchonine activates endoplasmic reticulum stress-induced apoptosis in human liver cancer cells. Exp Ther Med. 2018 Jun;15(6):5046-5050.
Reference 2 Apoptosis induced by doxorubicin and cinchonine in P388 multidrug-resistant cells. J Pharm Pharmacol. 2001 Jul;53(7):1029-39.
Reference 3 Hydrocinchonine, cinchonine, and quinidine potentiate paclitaxel-induced cytotoxicity and apoptosis via multidrug resistance reversal in MES-SA/DX5 uterine sarcoma cells. Environ Toxicol. 2011 Aug;26(4):424-31.
Reference 4 Cinchonine induces apoptosis of HeLa and A549 cells through targeting TRAF6. J Exp Clin Cancer Res. 2017 Feb 23;36(1):35.
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