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
Click to Show/Hide
|
||||
| Species Origin | Cinchona calisaya ... | Click to Show/Hide | |||
| Cinchona calisaya | |||||
| Disease | Hepatocellular carcinoma [ICD-11: 2C12] | Investigative | [1] | ||
| Structure |
|
Click to Download Mol2D MOL |
|||
| ADMET Property |
Absporption
Caco-2 Permeability
-4.628
MDCK Permeability
-4.786
PAMPA
- - -
HIA
- - -
Distribution
VDss
0.465
PPB
78.3%
BBB
-
Metabolism
CYP1A2 inhibitor
- - -
CYP1A2 substrate
- - -
CYP2C19 inhibitor
- - -
CYP2C19 substrate
+
CYP2C9 inhibitor
- - -
CYP2C9 substrate
- - -
CYP2D6 inhibitor
+++
CYP2D6 substrate
- - -
CYP3A4 inhibitor
- - -
CYP3A4 substrate
- -
CYP2B6 inhibitor
- - -
CYP2B6 substrate
- - -
CYP2C8 inhibitor
- -
HLM Stability
++
Excretion
CLplasma
3.473
T1/2
2.526
Toxicity
DILI
- -
Rat Oral Acute Toxicity
-
FDAMDD
++
Respiratory
+++
Human Hepatotoxicity
+
Ototoxicity
+
Drug-induced Nephrotoxicity
+
Drug-induced Neurotoxicity
++
Hematotoxicity
- -
Genotoxicity
+
Tips: 1. For the classification endpoints, the prediction probability values are transformed into six symbols: 0-0.1 (- - -), 0.1-0.3 (- -), 0.3-0.5 (-), 0.5-0.7 (+), 0.7-0.9 (++), and 0.9-1.0 (+++).
2. Additionally, the corresponding relationships of the three labels are as follows: excellent; medium; poor.
Click to Show/Hide
|
||||
| Click to Show/Hide the Molecular Information and External Link(s) of This Natural Product | |||||
| Formula |
C19H22N2O
|
||||
| PubChem CID | |||||
| 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 | |||||
| Herb ID | |||||
| 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] | |
