Cinchonidine - Moligand™, ≥98% , CAS No.485-71-2

CAS: 485-71-2 Cat. No.: C109632 Peso molecular: 294.39 Beilstein Registry Number: 89690 Número EC: 207-622-3

GRADE & PURITY Moligand™, ≥98%

Synonyms

BRD-K17661460-001-04-0 | BRD-K39079086-001-05-0 | IDI1_000501 | AKOS016008633 | HY-N0173 | KBio2_006781 | KBioGR_001805 | PDSP2_000142 | (R)-quinolin-4-yl((1S,2S,4S,5R)-5-vinylquinuclidin-2-yl)methanol | SDCCGMLS-0066969.P001 | Spectrum5_000964 | QUININE

Storage

Protected from light,Room temperature

Shipped In

Normal

Descripción general

application：

It finds its uses as an antimalarial compound. It is a lysosomotropic agent, inhibits Plasmodium falciparum, interferes with ferriprotoporphyrin formation and is a weak SERT inhibitor.

Specifications

Sinónimos

BRD-K17661460-001-04-0 | BRD-K39079086-001-05-0 | IDI1_000501 | AKOS016008633 | HY-N0173 | KBio2_006781 | KBioGR_001805 | PDSP2_000142 | (R)-quinolin-4-yl((1S, 2S, 4S, 5R)-5-vinylquinuclidin-2-yl)methanol | SDCCGMLS-0066969.P001 | Spectrum5_000964 | QUININE

Especificaciones y pureza

Moligand™, ≥98%

Mecanismos bioquímicos y fisiológicos

Quinine analog. Lysosomotropic agent. Inhibits Plasmodium falciparum. Interferes with ferriprotoporphyrin formation. Weak SERT inhibitor. Shows antimalarial effects in vivo. Orally active.

Condiciones de almacenamiento de almacenamiento

Protected from light, Room temperature

Enviado en

Normal

Grado

Moligand™

Nota

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Pureza

≥98%

Nombres e identificadores

• Pubchem Sid: 488187274
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488187274
• Sonrisas canónicas: C=CC1CN2CCC1CC2C(C3=CC=NC4=CC=CC=C34)O
• IUPAC Name: (R)-[(2S,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-quinolin-4-ylmethanol
• InChIKey: KMPWYEUPVWOPIM-KODHJQJWSA-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: GD2975000
• Peso molecular: 294.39
• Beilstein: 89690
• 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

Objetivos asociados (humanos)

ACHE Tclin Acetylcholinesterase (18204 Activities)

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SLC2A1 Tchem Glucose transporter (14755 Activities)

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WI-38 (2654 Activities)

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HepG2 (196354 Activities)

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POLI Tchem DNA polymerase iota (116820 Activities)

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TDP1 Tchem Tyrosyl-DNA phosphodiesterase 1 (345557 Activities)

Discover Target: TDP1

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SLCO1B1 Tchem Solute carrier organic anion transporter family member 1B1 (2672 Activities)

Discover Target: SLCO1B1

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CBX1 Tbio Chromobox protein homolog 1 (92434 Activities)

Discover Target: CBX1

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SLCO1B3 Tchem Solute carrier organic anion transporter family member 1B3 (2517 Activities)

Discover Target: SLCO1B3

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Objetivos asociados (no humanos)

ampC Beta-lactamase AmpC (62480 Activities)

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Hdac6 Histone deacetylase 6 (222 Activities)

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Trypanosoma brucei brucei (13300 Activities)

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Plasmodium falciparum (966862 Activities)

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ht1 Hexose transporter 1 (14071 Activities)

Discover Target: ht1

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rep Replicase polyprotein 1ab (378 Activities)

Discover Target: rep

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BCHE Cholinesterase (8742 Activities)

Discover Target: BCHE

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Leishmania mexicana mexicana (27 Activities)

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SARS-CoV-2 (38078 Activities)

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Mecanismos de acción

Propiedades químicas y físicas

• Solubilidad: Insoluble in water; Soluble in Alcohol,Ether,Chloroform
• Sensibilidad: Light Sensitive
• Rotación específica [α]: -107.5 ° (C=1, EtOH)
• Punto de fusión (°C): 204-206°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]