(+)-Cinchonine - Moligand™,≥98% , CAS No.118-10-5

CAS: 118-10-5 Cat. No.: C106926 Peso molecular: 294.39 Beilstein Registry Number: 89689 Número EC: 204-234-6

GRADE & PURITY Moligand™, ≥98%

Synonyms

(S)-quinolin-4-yl((2R,4S,5R)-5-vinylquinuclidin-2-yl)methanol | GNF-Pf-3189 | NCGC00262542-03 | .alpha.-Quinidine | NSC 6176 | HMS2096J18 | Prestwick3_000608 | LA40221 | (8R,9S)-Cinchonine | UNII-V43X79NZCD | 2-Quinuclidinemethanol, .alpha.-4-quinolyl-5-v

Storage

Store at 2-8°C,Protected from light,Argon charged

Shipped In

Wet ice

Descripción general

Cinchonine is a natural compound present in Cinchona bark with antimalarial, antitumor, anti-inflammatory, anti platelet-aggregation and anti-obesity properties. Cinchonine inhibits cells proliferation and autophagy and induces apoptosis through activation of Caspase-3. Cinchonine activates endoplasmic reticulum stress-induced apoptosis in human liver cancer cells

Specifications

Sinónimos

(S)-quinolin-4-yl((2R, 4S, 5R)-5-vinylquinuclidin-2-yl)methanol | GNF-Pf-3189 | NCGC00262542-03 | .alpha.-Quinidine | NSC 6176 | HMS2096J18 | Prestwick3_000608 | LA40221 | (8R, 9S)-Cinchonine | UNII-V43X79NZCD | 2-Quinuclidinemethanol, .alpha.-4-quinolyl-5-v

Especificaciones y pureza

Moligand™, ≥98%

Condiciones de almacenamiento de almacenamiento

Store at 2-8°C, Protected from light, Argon charged

Enviado en

Wet ice

Este producto requiere envío en cadena de frío. Los servicios terrestres y otros servicios económicos no están disponibles.

Grado

Moligand™

Pureza

≥98%

Nombres e identificadores

• Pubchem Sid: 504756027
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504756027
• Sonrisas canónicas: C=CC1CN2CCC1CC2C(C3=CC=NC4=CC=CC=C34)O
• IUPAC Name: (S)-[(2R,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-quinolin-4-ylmethanol
• InChIKey: KMPWYEUPVWOPIM-QAMTZSDWSA-N
• 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
• Isómeros SMILES: C=C[C@H]1CN2CC[C@H]1C[C@@H]2[C@H](C3=CC=NC4=CC=CC=C34)O
• WGK Alemania: 3
• RTECS: GD3500000
• Peso molecular: 294.39
• Beilstein: 89689
• Reaxy-Rn: 89687
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=89687&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Alkaloids and derivatives
    • Clase Cinchona alkaloids

• Kingdom: Organic compounds
• Superclass: Alkaloids and derivatives
• Clase: Cinchona alkaloids
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Cinchona alkaloids
• Alternative Parents: 4-quinolinemethanols Quinuclidines Aralkylamines Pyridines and derivatives Piperidines Benzenoids Heteroaromatic compounds Trialkylamines Secondary alcohols 1,2-aminoalcohols Azacyclic compounds Organopnictogen compounds Hydrocarbon derivatives Aromatic alcohols
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Cinchonan-skeleton - 4-quinolinemethanol - Quinoline - Quinuclidine - Aralkylamine - Piperidine - Pyridine - Benzenoid - Heteroaromatic compound - 1,2-aminoalcohol - Secondary alcohol - Tertiary aliphatic amine - Tertiary amine - Azacycle - Organoheterocyclic compound - Organic nitrogen compound - Hydrocarbon derivative - Organopnictogen compound - Organooxygen compound - Organonitrogen compound - Organic oxygen compound - Amine - Alcohol - Aromatic alcohol - Aromatic heteropolycyclic compound
• Descripción: This compound belongs to the class of organic compounds known as cinchona alkaloids. These are alkaloids structurally characterized by the presence of the cinchonan skeleton, which consists of a quinoline linked to an azabicyclo[2.2.2]octane moiety.
• External Descriptors: cinchona alkaloid - (8xi)-cinchonan-9-ol

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

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ACHE Tclin Acetylcholinesterase (18204 Activities)

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SLC2A1 Tchem Glucose transporter (14755 Activities)

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CYP2D6 Tclin Cytochrome P450 2D6 (33882 Activities)

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pol Human immunodeficiency virus type 1 reverse transcriptase (18245 Activities)

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Mecanismos de acción

Propiedades químicas y físicas

• Solubilidad: Insoluble in water; Slightly soluble in Alcohol; Very slightly soluble in Ether,Chloroform
• Sensibilidad: Light sensitive.
• Rotación específica [α]: 223 ° (C=0.5, EtOH)
• Punto de fusión (°C): 256-266°C
• Peso molecular: 294.400 g/mol
• XLogP3: 2.700
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 294.173 Da
• Monoisotopic Mass: 294.173 Da
• Topological Polar Surface Area: 36.400 Ų
• Heavy Atom Count: 22
• Formal Charge: 0
• Complexity: 412.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 4
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

Referencias

1. Huan Xue, Hao-Jie Xing, Bin Wang, Chao Fu, Yu-Shan Zhang, Xi Qiao, Chao Guo, Xiao-Li Zhang, Bin Hu, Xin Zhao, Li-Jiao Deng, Xiao-Chan Zhu, Yi Zhang, Yun-Feng Liu.  (2023)  Cinchonine, a Potential Oral Small-Molecule Glucagon-Like Peptide-1 Receptor Agonist, Lowers Blood Glucose and Ameliorates Non-Alcoholic Steatohepatitis.  Drug Design Development and Therapy,      [PMID:37197367] [10.2147/DDDT.S404055]

2. Zhi-Yuan Zhang, Li-Li Rui, Ya-Li Lin, Hui-Dan Zhang, Ji-Ming Ou, Jian-Feng He, Quan-Zhou Wu.  (2021)  Preparation of ordered macroporous molecularly imprinted polymers and their applications in purifying cinchona alkaloids from cinchona extract.  POLYMER INTERNATIONAL,  70  (9): (1344-1355).  [PMID:] [10.1002/pi.6205]

3. Yuan Tan, Lijing Jing, Yonghong Ding, Tianxin Wei.  (2015)  A novel double-layer molecularly imprinted polymer film based surface plasmon resonance for determination of testosterone in aqueous media.  APPLIED SURFACE SCIENCE,      [PMID:] [10.1016/j.apsusc.2015.03.031]

4. Li Liu, Xuecai Tan, Xiaoxue Fang, Yuexin Sun, Fuhou Lei, Zaiyin Huang.  (2012)  Electrochemical Sensor Based on Molecularly Imprinted Polymer Film Prepared with Functional Abietic-Type Acids as Cross-Linker for the Determination of Quinine.  ELECTROANALYSIS,  24  (7): (1647-1654).  [PMID:] [10.1002/elan.201200085]